Phthalate esters in main source water and drinking water of Zhejiang Province (China): Distribution and health risks.

PubMed

Wang, Xiaofeng; Lou, Xiaoming; Zhang, Nianhua; Ding, Gangqiang; Chen, Zhijian; Xu, Peiwei; Wu, Lizhi; Cai, Jianmin; Han, Jianlong; Qiu, Xueting

2015-10-01

To evaluate the distributions and health risks of phthalate esters in the main source water and corresponding drinking water of Zhejiang Province, the concentrations of 16 phthalate esters in water samples from 19 sites were measured from samples taken in the dry season and wet season. The concentration of the total phthalate ester congeners in source water ranged from 1.07 μg/L to 7.12 μg/L in the wet season, from 0.01 μg/L to 1.58 μg/L in the dry season, from 1.18 μg/L to 15.28 μg/L from drinking water in the wet season, and from 0.16 μg/L to 1.86 μg/L from drinking water in the dry season. Of the 16 phthalate esters, dimethyl phthalate, dibutyl phthalate, di-(2-ethyl-hexyl) phthalate, di-iso-butyl phthalate, bis-2-n-butoxyethyl phthalate, and dicyclohexyl phthalate were present in the samples analyzed, dominated by di-iso-butyl phthalate and di-(2-ethyl-hexyl) phthalate. The concentrations of phthalate esters in the wet season were all relatively higher than those in the dry season, and the drinking water had higher concentrations of phthalate esters than source water. The phthalate ester congeners studied pose little health risk to nearby citizens. Environ Toxicol Chem 2015;34:2205-2212. © 2015 SETAC. © 2015 SETAC.

40 CFR 721.3085 - Brominated phthalate ester.

Code of Federal Regulations, 2014 CFR

2014-07-01

... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Brominated phthalate ester. 721.3085... Substances § 721.3085 Brominated phthalate ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as brominated phthalate ester (PMN P-90-581) is...

40 CFR 721.3085 - Brominated phthalate ester.

Code of Federal Regulations, 2011 CFR

2011-07-01

... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Brominated phthalate ester. 721.3085... Substances § 721.3085 Brominated phthalate ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as brominated phthalate ester (PMN P-90-581) is...

40 CFR 721.3085 - Brominated phthalate ester.

Code of Federal Regulations, 2012 CFR

2012-07-01

... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Brominated phthalate ester. 721.3085... Substances § 721.3085 Brominated phthalate ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance identified generically as brominated phthalate ester (PMN P-90-581) is...

Establishing the Biological Relevance of Dipentyl Phthalate Reductions in Fetal Rat Testosterone Production and Plasma and Testis Testosterone Levels

EPA Science Inventory

Phthalate esters (PEs) constitute a large class of compounds that are used for many consumer product applications. Many of the C2-C7 di-ortho PEs reduce fetal testicular hormone and gene expression levels in rats resulting in adverse effects seen later in life but it appears that...

Determination of phthalate esters from environmental water samples by micro-solid-phase extraction using TiO2 nanotube arrays before high-performance liquid chromatography.

PubMed

Zhou, Qingxiang; Fang, Zhi; Liao, Xiangkun

2015-07-01

We describe a highly sensitive micro-solid-phase extraction method for the pre-concentration of six phthalate esters utilizing a TiO2 nanotube array coupled to high-performance liquid chromatography with a variable-wavelength ultraviolet visible detector. The selected phthalate esters included dimethyl phthalate, diethyl phthalate, dibutyl phthalate, butyl benzyl phthalate, bis(2-ethylhexyl)phthalate and dioctyl phthalate. The factors that would affect the enrichment, such as desorption solvent, sample pH, salting-out effect, extraction time and desorption time, were optimized. Under the optimum conditions, the linear range of the proposed method was 0.3-200 μg/L. The limits of detection were 0.04-0.2 μg/L (S/N = 3). The proposed method was successfully applied to the determination of six phthalate esters in water samples and satisfied spiked recoveries were achieved. These results indicated that the proposed method was appropriate for the determination of trace phthalate esters in environmental water samples. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Semi-volatile organic compounds in heating, ventilation, and air-conditioning filter dust in retail stores.

PubMed

Xu, Y; Liang, Y; Urquidi, J R; Siegel, J A

2015-02-01

Retail stores contain a wide range of products that can emit a variety of indoor pollutants. Among these chemicals, phthalate esters and polybrominated diphenyl ethers (PBDEs) are two important categories of semi-volatile organic compounds (SVOCs). Filters in heating, ventilation, and air-conditioning (HVAC) system collect particles from large volumes of air and thus potentially provide spatially and temporally integrated SVOC concentrations. This study measured six phthalate and 14 PBDE compounds in HVAC filter dust in 14 retail stores in Texas and Pennsylvania, United States. Phthalates and PBDEs were widely found in the HVAC filter dust in retail environment, indicating that they are ubiquitous indoor pollutants. The potential co-occurrence of phthalates and PBDEs was not strong, suggesting that their indoor sources are diverse. The levels of phthalates and PBDEs measured in HVAC filter dust are comparable to concentrations found in previous investigations of settled dust in residential buildings. Significant correlations between indoor air and filter dust concentrations were found for diethyl phthalate, di-n-butyl phthalate, and benzyl butyl phthalate. Reasonable agreement between measurements and an equilibrium model to describe SVOC partitioning between dust and gas-phase is achieved. © 2014 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd.

Organophosphate esters and phthalate esters in human hair from rural and urban areas, Chongqing, China: Concentrations, composition profiles and sources in comparison to street dust.

PubMed

He, Ming-Jing; Lu, Jun-Feng; Ma, Jing-Ye; Wang, Huan; Du, Xiao-Fan

2018-06-01

Human hair and street dust from rural and urban areas in Chongqing were collected to analyze Organophosphate esters (OPEs) and phthalate esters (PAEs). Concentrations of OPEs in urban hair were significantly higher than those in rural hair, whereas PAEs concentrations in rural hair were significantly higher than those in urban hair. Different composition patterns of OPEs were observed in rural and urban hair, where tris (2-chloroisopropyl) phosphate (TCIPP), tris (butyl) phosphate (TNBP) and triphenyl phosphate (TPHP) were the dominating analogues in rural hair, accounting for 62.1% of the OPEs burden, and tris (methylphenyl) phosphate (TMPP) exhibited a high contribution in urban hair, responsible for 51.3% of total OPEs, which differed from the composition profiles in corresponding street dust. Analogous composition patterns of PAEs were found in hair of both areas. Di-(2-ethylhexyl) phthalate (DEHP), dibutyl phthalate (DNBP), diisobutyl phthalate (DIBP) and diethyl phthalate (DEP) were the most abundant analogues in hair samples, while DEHP was the predominant analogue in dust samples. No clear tendency was obtained between the increasing ages and the concentrations of both compounds. Most OPEs and PAEs congeners showed significantly positive correlation with one another in rural hair. On the contrary, different correlation patterns were observed in urban hair for OPEs and PAEs, indicating multiple or additional sources existed in urban areas. Significant correlations of OPEs and PAEs were found between hair and corresponding street dust samples, but poor correlations of OPEs and PAEs were observed between rural hair and rural indoor dust, suggesting that street dust may be a predominant exogenous source for human exposure to OPEs and PAEs in this area. Copyright © 2018 Elsevier Ltd. All rights reserved.

Fabrication of magnetic microsphere-confined graphene for the preconcentration of some phthalate esters from environmental water and soybean milk samples followed by their determination by HPLC.

PubMed

Wang, Weina; Ma, Ruiyang; Wu, Qiuhua; Wang, Chun; Wang, Zhi

2013-05-15

In this study, a magnetic microsphere-confined graphene (Fe3O4@SiO2-G) was prepared as a novel adsorbent for the preconcentration of some phthalate esters in environmental water and soybean milk samples prior to high performance liquid chromatography analysis. The properties and morphology of the Fe3O4@SiO2-G were characterized by transmission electron microscopy and X-ray diffraction. This novel graphene-based magnetic nanocomposite showed great adsorptive ability toward the analytes. The method, which takes the advantages of both the high adsorption capacity of G and easy phase separation of the magnetic adsorbent from the sample solution, could avoid the time-consuming experimental procedures related to the traditional solid phase extraction. Various experimental parameters that could affect the extraction efficiencies, such as the amount of Fe3O4@SiO2-G, the extraction time, the pH of sample solution and the desorption conditions, were investigated. Under the optimum conditions, the limits of detection (S/N=3) of the method for the compounds were between 0.07 and 0.10 ng mL(-1) in water samples, and between 0.15 and 0.30 ng mL(-1) in soybean milk samples. The relative standard deviations (RSDs) varied from 2.7% to 6.1% (n=5). The recoveries of the method were in the range between 87.2% and 109.0% for environmental water and soybean milk samples. The method is suitable to determine the five phthalate esters (diallyl phthalate, di-n-propyl-phthalate, benzyl butyl phthalate, dicyclohexyl-phthalate and diethyl-hexyl-phthalate) in environmental water and soybean milk samples. Copyright © 2013 Elsevier B.V. All rights reserved.

AN ASSESSMENT OF THE TOXICITY OF PHTHALATE ESTERS TO FRESHWATER BENTHOS. 1. AQUEOUS EXPOSURES

EPA Science Inventory

Tests were performed with the freshwater invertebrates, Hyalella azteca, Chironomus tentans, and Lumbriculus variegatus to determine the acute toxicity of six phthalate esters, including dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DBP), butylbenzyl ph...

Simultaneous determination of 22 phthalate esters in polystyrene food-contact materials by ultra performance convergence chromatography with tandem mass spectrometry.

PubMed

Fan, Ying-Li; Ma, Ming; Cui, He-Zhen; Liu, Shu; Yang, Min-Li; Hou, Xiu-Feng

2018-05-29

A method for the determination of 22 phthalate esters in polystyrene food-contact materials has been established using ultra performance convergence chromatography with tandem mass spectrometry. In this method, 22 phthalate esters were analyzed in less than 3.5 min on an ACQUITY Tours 1-AA column by gradient elution. The mobile phase, the compensation solvent, the flow rate of mobile phase, column temperature and automatic back pressure regulator pressure were optimized, respectively. There was a good linearity of 20 phthalate esters with a range of 0.05-10 mg/L, diisodecyl phthalate and diisononyl phthalate were 0.25-10 mg/L, and the correlation coefficients of all phthalates were higher than 0.99 and those of 16 phthalates were higher than 0.999. The limits of detection and the limits of quantification of 15 phthalates were 0.02 and 0.05 mg/kg, meanwhile diallyl phthalate, diisobutyl phthalate, dimethyl phthalate, di-n-butyl phthalate and di(2-ethylhexyl) phthalate were 0.05 and 0.10 mg/kg, diisodecyl phthalate and diisononyl phthalate were 0.10 and 0.25 mg/kg. The spiked recoveries were 76.26-107.76%, and the relative standard deviations were 1.78-12.10%. Results support this method as an efficient alternative to apply for the simultaneous determination of 22 phthalate esters in common polystyrene food-contact materials. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

Identification of phthalate esters in the serum of young Puerto Rican girls with premature breast development.

PubMed Central

Colón, I; Caro, D; Bourdony, C J; Rosario, O

2000-01-01

Premature breast development (thelarche) is the growth of mammary tissue in girls younger than 8 years of age without other manifestations of puberty. Puerto Rico has the highest known incidence of premature thelarche ever reported. In the last two decades since this serious public health anomaly has been observed, no explanation for this phenomenon has been found. Some organic pollutants, including pesticides and some plasticizers, can disrupt normal sexual development in wildlife, and many of these have been widely used in Puerto Rico. This investigation was designed to identify pollutants in the serum of Puerto Rican girls with premature thelarche. A method for blood serum analysis was optimized and validated using pesticides and phthalate esters as model compounds of endocrine-disrupting chemicals. Recovery was > 80% for all compounds. We performed final detection by gas chromatography/mass spectrometry. We analyzed 41 serum samples from thelarche patients and 35 control samples. No pesticides or their metabolite residues were detected in the serum of the study or control subjects. Significantly high levels of phthalates [dimethyl, diethyl, dibutyl, and di-(2-ethylhexyl)] and its major metabolite mono-(2-ethylhexyl) phthalate were identified in 28 (68%) samples from thelarche patients. Of the control samples analyzed, only one showed significant levels of di-isooctyl phthalate. The phthalates that we identified have been classified as endocrine disruptors. This study suggests a possible association between plasticizers with known estrogenic and antiandrogenic activity and the cause of premature breast development in a human female population. PMID:11017896

A study on emission of phthalate esters from plastic materials using a passive flux sampler

NASA Astrophysics Data System (ADS)

Fujii, M.; Shinohara, N.; Lim, A.; Otake, T.; Kumagai, K.; Yanagisawa, Y.

Phthalate esters are used as plasticizer in many plastics, and several studies have shown their toxicity. Phthalate esters are gradually emitted over time, and so it is conceivable that they pose a significant health risk. This study aims to investigate the temperature dependence of the emissions of various phthalate esters and to estimate the health risks of these emissions at various temperatures. A passive-type sampler was developed to measure the flux of phthalate esters from the surface of plastic materials. With this sampler, we examined three widely used plastic materials: synthetic leather, wallpaper and vinyl flooring. The observed maximum emissions of diethyl phthalate, dibutyl phthalate, and diethylhexyl phthalate (DEHP) from these materials at 20°C were 0.89, 0.77, and 14 μg m -2 h -1, respectively. Emissions at 80°C were 2.8, 4.5×10 2, and 1.5×10 3 μg m -2 h -1, respectively. The results showed this temperature dependence is determined primarily by the type of phthalate ester and less so by the type of material. The estimation from the results of temperature dependence indicated the concentration of DEHP in a vehicle left out in the sunshine during the day can exceed the recommended levels of Japan Ministry of Health, Labour and Welfare.

Request from the Phthalate Esters Panel of the American Chemistry Council for correction of EPA's Action Plan for Phthalate Esters

EPA Pesticide Factsheets

The Phthalate Esters Panel (Panel) of the American Chemistry Council submits this Request for Correction to EPA under the Guidelines for Ensuring and Maximizing the Quality, Objectivity, Utility, and Integrity, of Information Disseminated by the Environmental Protection Agency

Toxic effects of several phthalate esters on the embryos and larvae of abalone Haliotis diversicolor supertexta

NASA Astrophysics Data System (ADS)

Yang, Zhihui; Zhang, Xiangjing; Cai, Zhonghua

2009-05-01

As the most widely used plasticizers in the world, phthalate esters (PAEs) are potential endocrine disruption compounds (EDCs). In the present study, the toxicity of dimethyl phthalate (DMP), diethyl phthalate (DEP), dibutyl phthalate (DBP), di (2-ethylhexyl) phthalate (DEHP) on embryogenesis and larvae development of the marine univalve Haliotis diversicolor supertexta was examined in laboratory. The results show that the malformation of embryos appeared during the experiment, such as embryos died or lysed, small transparent flocculent rings studded on the periphery of the embryo, and the larvae could failed to hatch. In embryo toxic test, embryos incubated at the highest concentration of DMP, DEP and DBP solutions showed significantly high abnormal rate compared with the control, while DEHP solutions displayed no significant difference. In larval toxic test, in all concentrations of DMP, DEP and DBP solutions, larval settlement rates were low significantly than that of the control. Similarly, DEHP solutions show nearly no effect on the larval settlement. The order of toxicity on embryos and larvae is DBP>DEP>DMP>DEHP. Being a simple and easy stimulation to indoor spawn, sensitive to environmental factors, and short culture time, the embryos of H. diversicolor supertexta can be used to indicate toxicity of the PAEs.

Determination of phthalates released from paper packaging materials by solid-phase extraction-high-performance liquid chromatography.

PubMed

Gao, Xin; Yang, Bofeng; Tang, Zhixu; Luo, Xin; Wang, Fengmei; Xu, Hui; Cai, Xue

2014-01-01

A solid phase extraction (SPE) high-performance liquid chromatography (HPLC) method was developed for the simultaneous determination of 10 phthalic acid esters (dimethyl phthalate, diethyl phthalate, dipropyl phthalate, benzylbutyl phthalate, diisobutyl phthalate, dicyclohexyl phthalate, diamyl phthalate, di-n-hexyl phthalate, di-n-octyl phthalate and di-2-ethylhexyl phthalate) released from food paper packaging materials. The use of distilled water, 3% acetic acid (w/v), 10% ethanol (v/v) and 95% ethanol (v/v) instead of the different types of food simulated the migration of 10 phthalic acid esters from food paper packaging materials; the phthalic acid esters in four food simulants were enriched and purified by a C18 SPE column and nitrogen blowing, and quantified by HPLC with a diode array detector. The chromatographic conditions and extraction conditions were optimized and all 10 of the phthalate acid esters had a maximum absorbance at 224 nm. The method showed limitations of detection in the range of 6.0-23.8 ng/mL the correlation coefficients were greater than 0.9999 in all cases, recovery values ranged between 71.27 and 106.97% at spiking levels of 30, 60 and 90 ng/mL and relative standard deviation values ranged from 0.86 to 8.00%. The method was considered to be simple, fast and reliable for a study on the migration of these 10 phthalic acid esters from food paper packaging materials into food.

Validation of an automated counting procedure for phthalate-induced testicular multinucleated germ cells.

PubMed

Spade, Daniel J; Bai, Cathy Yue; Lambright, Christy; Conley, Justin M; Boekelheide, Kim; Gray, L Earl

2018-06-15

In utero exposure to certain phthalate esters results in testicular toxicity, characterized at the tissue level by induction of multinucleated germ cells (MNGs) in rat, mouse, and human fetal testis. Phthalate exposures also result in a decrease in testicular testosterone in rats. The anti-androgenic effects of phthalates have been more thoroughly quantified than testicular pathology due to the significant time requirement associated with manual counting of MNGs on histological sections. An automated counting method was developed in ImageJ to quantify MNGs in digital images of hematoxylin-stained rat fetal testis tissue sections. Timed pregnant Sprague Dawley rats were exposed by daily oral gavage from gestation day 17 to 21 with one of eight phthalate test compounds or corn oil vehicle. Both the manual counting method and the automated image analysis method identified di-n-butyl phthalate, butyl benzyl phthalate, dipentyl phthalate, and di-(2-ethylhexyl) phthalate as positive for induction of MNGs. Dimethyl phthalate, diethyl phthalate, the brominated phthalate di-(2-ethylhexyl) tetrabromophthalate, and dioctyl terephthalate were negative. The correlation between automated and manual scoring metrics was high (r = 0.923). Results of MNG analysis were consistent with these compounds' anti-androgenic activities, which were confirmed in an ex vivo testosterone production assay. In conclusion, we have developed a reliable image analysis method that can be used to facilitate dose-response studies for the reproducible induction of MNGs by in utero phthalate exposure. Copyright © 2018 Elsevier B.V. All rights reserved.

Impact of three phthalate esters on the sexual reproduction of the Monogonont rotifer, Brachionus calyciflorus.

PubMed

Cruciani, V; Iovine, C; Thomé, J-P; Joaquim-Justo, C

2016-01-01

Phthalate esters are widespread contaminants that can cause endocrine disruption in vertebrates. Studies showed that molecules with hormonal activities in vertebrates and invertebrates can affect asexual and sexual reproduction in rotifers. We investigated the impact of di-hexylethyl phthalate (DEHP), di-butyl phthalate (DBP) and butylbenzyl phthalate (BBP), on the asexual and sexual reproduction of the freshwater monogonont rotifer Brachionus calyciflorus in order to determine a potential environmental risk for sexual reproduction. We observed that DEHP has no significant impact on both asexual and sexual reproduction up to 2 mg/L. DBP has a positive effect on asexual reproduction at concentrations from 0.05 to 1 mg/L, but depresses it at 2 mg/L. Sexual reproduction is only affected at 2 mg/L and the impact observed is negative. BBP displayed a negative impact on both asexual and sexual reproduction at 1 and 2 mg/L. However we showed that the impacts of BBP on mixis and fertilization rates observed are due to the decrease in population growth rates at these concentrations and not to a direct impact of BBP on the mixis and the fertilization processes. Our results show that sexual reproduction in B. calyciflorus is not more sensitive than asexual reproduction to any of the substances tested which indicates the mode of action of these molecules is related to general toxicity and not to an interference with potential endocrine regulation of sexual reproduction. Comparison of effect concentrations and surface water contamination by phthalate esters suggests these compounds do not constitute a risk for primary consumers in these environments.

Presence of phthalate derivatives in the essential oils of a medicinal plant Achillea tenuifolia.

PubMed

Manayi, Azadeh; Kurepaz-Mahmoodabadi, Mahdieh; Gohari, Ahmad R; Ajani, Yousef; Saeidnia, Soodabeh

2014-11-28

Phthalate, esters of phthalic acid, are mainly applied as plasticizers and cause several human health and environment hazards. The essential oils of Achillea species have attracted a great concern, since several biological activities have been reported from varieties of these medicinal species. On the other side, due to the problems regarding the waste disposal in developing countries, phthalate derivatives can easily release from waste disposal to the water and soil resulting in probable absorption and accumulation by medicinal and dietary plants. As a matter of fact, although the toxicity of phthalate derivatives in human is well-known, food crops and medicinal plants have been exposing to phthalates that can be detected in their extracts and essential oils. Achillea tenuifolia (Compositea) is one of these herbaceous plants with traditional applications which widely growing in Iran. The plant root was subjected to hydro-distillation for 4 h using Clevenger type apparatus to obtain its essential oil before and after acid treatment. Both of the hydro-distilled essential oils were analysed by GC-MS method resulted in recognition of their constituent. Phthalate contamination as (1, 2-benzenedicarboxylic acid, bis (2-methylpropyl) ester (5.4%) and phthalic acid (4.5%), were identified in the first and second extracted oils, respectively. As a warning, due to the potential role of phthalates to cause reproductive toxicity, disturb of endocrine system and causing cancers, medicinal plants have to be considered through quality control for detection of these compounds.

An unusual strategy for the anoxic biodegradation of phthalate.

PubMed

Ebenau-Jehle, Christa; Mergelsberg, Mario; Fischer, Stefanie; Brüls, Thomas; Jehmlich, Nico; von Bergen, Martin; Boll, Matthias

2017-01-01

In the past two decades, the study of oxygen-independent degradation of widely abundant aromatic compounds in anaerobic bacteria has revealed numerous unprecedented enzymatic principles. Surprisingly, the organisms, metabolites and enzymes involved in the degradation of o-phthalate (1,2-dicarboxybenzene), mainly derived from phthalate esters that are annually produced at the million ton scale, are sparsely known. Here, we demonstrate a previously unknown capacity of complete phthalate degradation in established aromatic compound-degrading, denitrifying model organisms of the genera Thauera, Azoarcus and 'Aromatoleum'. Differential proteome analyses revealed phthalate-induced gene clusters involved in uptake and conversion of phthalate to the central intermediate benzoyl-CoA. Enzyme assays provided in vitro evidence for the formation of phthaloyl-CoA by a succinyl-CoA- and phthalate-specific CoA transferase, which is essential for the subsequent oxygen-sensitive decarboxylation to benzoyl-CoA. The extreme instability of the phthaloyl-CoA intermediate requires highly balanced CoA transferase and decarboxylase activities to avoid its cellular accumulation. Phylogenetic analysis revealed phthaloyl-CoA decarboxylase as a novel member of the UbiD-like, (de)carboxylase enzyme family. Homologs of the encoding gene form a phylogenetic cluster and are found in soil, freshwater and marine bacteria; an ongoing global distribution of a possibly only recently evolved degradation pathway is suggested.

An unusual strategy for the anoxic biodegradation of phthalate

PubMed Central

Ebenau-Jehle, Christa; Mergelsberg, Mario; Fischer, Stefanie; Brüls, Thomas; Jehmlich, Nico; von Bergen, Martin; Boll, Matthias

2017-01-01

In the past two decades, the study of oxygen-independent degradation of widely abundant aromatic compounds in anaerobic bacteria has revealed numerous unprecedented enzymatic principles. Surprisingly, the organisms, metabolites and enzymes involved in the degradation of o-phthalate (1,2-dicarboxybenzene), mainly derived from phthalate esters that are annually produced at the million ton scale, are sparsely known. Here, we demonstrate a previously unknown capacity of complete phthalate degradation in established aromatic compound-degrading, denitrifying model organisms of the genera Thauera, Azoarcus and ‘Aromatoleum'. Differential proteome analyses revealed phthalate-induced gene clusters involved in uptake and conversion of phthalate to the central intermediate benzoyl-CoA. Enzyme assays provided in vitro evidence for the formation of phthaloyl-CoA by a succinyl-CoA- and phthalate-specific CoA transferase, which is essential for the subsequent oxygen-sensitive decarboxylation to benzoyl-CoA. The extreme instability of the phthaloyl-CoA intermediate requires highly balanced CoA transferase and decarboxylase activities to avoid its cellular accumulation. Phylogenetic analysis revealed phthaloyl-CoA decarboxylase as a novel member of the UbiD-like, (de)carboxylase enzyme family. Homologs of the encoding gene form a phylogenetic cluster and are found in soil, freshwater and marine bacteria; an ongoing global distribution of a possibly only recently evolved degradation pathway is suggested. PMID:27392087

Phthalate Esters and Reproductive Toxicity** Presentation requested by State of Mass Use Reductions Committee-TURI

EPA Science Inventory

Phthalate esters and reproductive toxicity the presentation described the uses of phthalates, the toxicity to mammals with a focus on reproductive toxicity and the potency of these chemicals to disrupt mammalian reproductive development in utero

Perilous plastics - are phthalate esters a risk for human reproductive health?

EPA Science Inventory

Phthalate diesters are high-production volume chemicals used to impart flexibility to polyvinyl chloride plastic (e.g. children’s toys and medical tubing) and are also found in other products (e.g. health and beauty products). Certain phthalate esters inhibit reproductive develop...

Perilous plasticizers - are phthalate esters a risk for human reproductive health?

EPA Science Inventory

Phthalate diesters are high-production volume chemicals used to impart flexibility to polyvinyl chloride plastic (e.g. children’s toys and medical tubing) as well as other products (e.g. health and beauty products). Certain phthalate esters inhibit reproductive development in la...

Phthalate esters in water and surface sediments of the Pearl River Estuary: distribution, ecological, and human health risks.

PubMed

Li, Xiaohui; Yin, Pinghe; Zhao, Ling

2016-10-01

The Pearl River Estuary (PRE) is vulnerable due to the increasingly serious environmental pollution, such as phthalate esters (PAEs) contaminants, from the Pearl River Delta (PRD). The concentrations of six US Environmental Protection Agency (USEPA) priority PAEs in water and surface sediments collected from the PRD's six main estuaries in spring, summer, and winter 2013 were measured by GC-MS. Total PAEs (∑6PAEs) concentrations were from 0.5 to 28.1 μg/L and from 0.88 to 13.6 μg/g (dry weight (DW)) in water and surface sediments, respectively. The highest concentration was detected in summer. Higher concentrations of PAEs were found in Yamen (YM) and Humen (HM) areas than the other areas. Bis(2-ethylhexyl)phthalate (DEHP) and dibutyl phthalate (DBP) were the dominant PAEs in the investigated areas, contributing between 61 and 95 % of the PAEs in water and from 85 to 98 % in surface sediments. Based on risk quotients (RQs), DEHP posed greater ecological risks to the studied aquatic environments than other measured compounds. Little human health risk from the target PAEs was identified.

URINARY METABOLITES OF DI-N-OCTYL PHTHALATE IN RATS

EPA Science Inventory

Di-n-octyl phthalate (DnOP) is a plasticizer used in polyvinyl chloride plastics, cellulose esters, and polystyrene resins. The metabolism of DnOP results in the hydrolysis of one ester linkage to produce mono-n-octyl phthalate (MnOP), which subsequently metabolizes to form oxida...

Phthalate esters (PAEs) in indoor PM10/PM2.5 and human exposure to PAEs via inhalation of indoor air in Tianjin, China

NASA Astrophysics Data System (ADS)

Zhang, Leibo; Wang, Fumei; Ji, Yaqin; Jiao, Jiao; Zou, Dekun; Liu, Lingling; Shan, Chunyan; Bai, Zhipeng; Sun, Zengrong

2014-03-01

In this study, filter samples of six Phthalate esters (PAEs) in indoor PM10 and PM2.5 were collected from thirteen homes in Tianjin, China. The results showed that the concentrations of Σ6PAEs in indoor PM10 and PM2.5 were in the range of 13.878-1591.277 ng m-3 and 7.266-1244.178 ng m-3, respectively. Dibutyl phthalate (DBP) was the most abundant compounds followed by di-2-ethylhexyl phthalate (DEHP) in indoor PM10 and PM2.5. Whereas DBP and dimethyl phthalate (DMP) were the predominant compounds in indoor air (gas-phase + particle-phase), the median values were 573.467 and 368.364 ng m-3 respectively. The earlier construction time, the lesser indoor area, the old decoration, the very crowded items coated with plastic and a lower frequency of dusting may lead to a higher level of PAEs in indoor environment. The six PAEs in indoor PM10 and PM2.5 were higher in summer than those in winter. The daily intake (DI) of six PAEs for five age groups through air inhalation in indoor air in Tianjin was estimated. The results indicated that the highest exposure dose was DBP in every age group, and infants experienced the highest total DIs (median: 664.332 ng kg-bw-1 day-1) to ∑6PAEs, whereas adults experienced the lowest total DIs (median: 155.850 ng kg-bw-1 day-1) to ∑6PAEs. So, more attention should be paid on infants in the aspect of indoor inhalation exposure to PAEs.

Pretreatment of industrial wastewater containing phthalate esters by centrifugation

DOE Office of Scientific and Technical Information (OSTI.GOV)

Petrosky, C.J.; Vidic, R.D.

1996-11-01

In this study, a full-scale commercial centrifuge was used to treat, on a continuous basis, the entire wastewater stream generated by a chemical manufacturing facility which produces a variety of phthalate, adipate, maleate, and trimellitate esters. The wastewater from this facility is comprised of process water, equipment was water, and rain water runoff containing varying concentrations of bis(2-ethylhexyl) phthalate (BEHP), di-n-octyl phthalate (DNOP), and di-n-butyl phthalate (DNBP) esters in addition to mono-ester salts and alcohols. The wastewater is discharged to the local Publicly Owned Treatment Works (POTW) under pretreatment regulations which specify an effluent limitation of 5.0 mg/L on themore » total toxic organic (TTO) concentration which can be placed on the combined BEHP, DNOP, and DNBP ester concentration. Various esters and long chain alcohols present in the wastewater have very low water solubilities and are considered immiscible. They form a dispersed phase in the wastewater that has a specific gravity in the range of 0.88 to 0.93. Separation of the dispersed phase containing the regulated esters from the heavier water phase to consistently below 5.0 mg/L poses a challenge due to the stability of this colloidal suspension. The objective of this study was to evaluate the effectiveness of centrifugation in meeting the 5.0 mg/L effluent limit on the total BEHP, DNOP, and DNBP ester concentration.« less

Fungal biodegradation of dibutyl phthalate and toxicity of its breakdown products on the basis of fungal and bacterial growth.

PubMed

Ahuactzin-Pérez, M; Torres, J L; Rodríguez-Pastrana, B R; Soriano-Santos, J; Díaz-Godínez, G; Díaz, R; Tlecuitl-Beristain, S; Sánchez, C

2014-11-01

Phthalates are esters of phthalic acid that give flexibility to polyvinyl chloride. Diverse studies have reported that these compounds might be carcinogenic, mutagenic and/or teratogenic. Radial growth rate, biomass, hyphal thickness of Neurospora sitophyla, Trichoderma harzianum and Aspergillus niger, grown in two different concentrations of dibutyl phthalate (DBP) (500 and 1,000 mg/l) in agar and in submerged fermentation were studied. The inhibitory concentration (IC50) and the constant of biodegradation of dibutyl phthalate in Escherichia coli cultures were used to evaluate toxicity. The radial growth rate and thickness of the hypha were positively correlated with the concentration of phthalate. The pH of the cultures decreased as the fermentation proceeded. It is shown that these fungi are able to degrade DBP to non-toxic compounds and that these can be used as sole carbon and energy sources by this bacterium. It is demonstrated that the biodegradation of the DBP is directly correlated with the IC50. This is the first study that reports a method to determine the biodegradation of DBP on the basis of the IC50 and fungal growth, and the effect of this phthalate on the growth and thickness of hyphae of filamentous fungi in agar and in submerged fermentation.

Direct sample introduction gas chromatography and mass spectrometry for the determination of phthalate esters in cleaning products.

PubMed

Cacho, J I; Campillo, N; Viñas, P; Hernández-Córdoba, M

2015-02-06

A method using direct sample introduction (DSI) coupled to gas chromatography-mass spectrometry (GC-MS) is developed for the determination of six phthalate esters (dimethyl, diethyl, dibutyl, butylbenzyl, diethylhexyl and dioctyl phthalate) in cleaning products. The different variables involved in the DSI step, including venting time and temperature, vaporisation time and temperature, injector heating temperature and gas flow rate and pressure, were evaluated and optimised using Taguchi orthogonal arrays. The proposed method, using calibration against methanolic standards, showed good linearity in the 0.05-15 μg g(-1) range and good repeatability, with RSD values ranging from 3.5% to 5.7%. Quantification limits between 0.010 and 0.041 μg g(-1), depending on the compound, were attained, while recovery assays provided values from 83% to 115%. Twenty-seven cleaning products were analysed using the DSI-GC-MS method, being four phthalates (dimethyl, diethyl, dibutyl and diethylhexyl phthalate) found in fourteen of them at concentration levels in the 0.1-21 μg g(-1) range. Compared with the most common GC injection technique, which uses the split/splitless injector, the proposed DSI procedure provided larger peak areas and lower detection limits, as result of the greater injected volume and reduction in noise. Copyright © 2014 Elsevier B.V. All rights reserved.

In utero exposure to di(n)butyl phthalate reduces testicular testosterone and testis size in a dose-dependent manner in Harlan Sprague Dawley fetal rats

EPA Science Inventory

Phthalate esters are widely used to impart flexibility to plastics (e.g. plastic medical devices and children’s toys) as well as other uses in health and beauty products and some pharmaceuticals. Certain phthalate esters cause reproductive malformations and decrease androgen-dep...

Studies into the transfer and migration of phthalate esters from aluminium foil-paper laminates to butter and margarine.

PubMed

Page, B D; Lacroix, G M

1992-01-01

Retail samples of Canadian butter and margarine wrapped in aluminium foil-paper laminate were found to contain dibutyl, butyl benzyl and/or di-2-ethylhexyl phthalate (DBP, BBP, DEHP) as packaging migrants at levels up to 10.6, 47.8 and 11.9 micrograms/g, respectively. These phthalates were determined by capillary gas chromatography with flame ionization detection (GC-FID) after clean-up of the separated oil by sweep co-distillation. The phthalate esters found in the contacted butter or margarine were also found in the contacting wrappers. They were determined in wrapper extracts by liquid chromatography with diode array detection or by GC-FID. Analysis of unused wrappers showed 76-88% of the total DBP and DEHP to be present on the foil (outer) surface as a component of the protective coating (washcoat). The remainder of the DBP and DEHP was found on the food-contacting paper surface, presumably by transfer from the outer to inner surface during storage in tightly wound rolls, although transfer of phthalate esters, if present in the paper-foil adhesive, cannot be ruled out. Food-contacting surface concentrations of DBP and DEHP were found to be 2.4 to 4.7 and 2.8 to 3.6 micrograms/cm2, respectively. Samples of each packaging component: paper, foil, adhesive, washcoat and inks were analysed for phthalate esters and only the washcoat was found to contain phthalate esters.

Partitioning of phthalates among the gas phase, airborne particles and settled dust in indoor environments

NASA Astrophysics Data System (ADS)

Weschler, Charles J.; Salthammer, Tunga; Fromme, Hermann

A critical evaluation of human exposure to phthalate esters in indoor environments requires the determination of their distribution among the gas phase, airborne particles and settled dust. If sorption from the gas phase is the dominant mechanism whereby a given phthalate is associated with both airborne particles and settled dust, there should be a predictable relationship between its particle and dust concentrations. The present paper tests this for six phthalate esters (DMP, DEP, DnBP, DiBP, BBzP and DEHP) that have been measured in both the air and the settled dust of 30 Berlin apartments. The particle concentration, CParticle, of a given phthalate was calculated from its total airborne concentration and the concentration of airborne particles (PM 4). This required knowledge of the particle-gas partition coefficient, Kp, which was estimated from either the saturation vapor pressure ( ps) or the octanol/air partition coefficient ( KOA). For each phthalate in each apartment, the ratio of its particle concentration to its dust concentration ( CParticle/ CDust) was calculated. The median values of this ratio were within an order of magnitude of one another for five of the phthalate esters despite the fact that their vapor pressures span four orders of magnitude. This indicates that measurements of phthalate ester concentrations in settled dust can provide an estimate of their concentration in airborne particles. When the latter information is coupled with measurements of airborne particle concentrations, the gas-phase concentrations of phthalates can also be estimated and, subsequently, the contribution of each of these compartments to indoor phthalate exposures.

A monograph on the remediation of hazardous phthalates.

PubMed

Benjamin, Sailas; Pradeep, Selvanesan; Josh, Moolakkariyil Sarath; Kumar, Sunil; Masai, Eiji

2015-11-15

Phthalates or phthalic acid esters are a group of xenobiotic and hazardous compounds blended in plastics to enhance their plasticity and versatility. Enormous quantities of phthalates are produced globally for the production of plastic goods, whose disposal and leaching out into the surroundings cause serious concerns to the environment, biota and human health. Though in silico computational, in vitro mechanistic, pre-clinical animal and clinical human studies showed endocrine disruption, hepatotoxic, teratogenic and carcinogenic properties, usage of phthalates continues due to their cuteness, attractive chemical properties, low production cost and lack of suitable alternatives. Studies revealed that microbes isolated from phthalate-contaminated environmental niches efficiently bioremediate various phthalates. Based upon this background, this review addresses the enumeration of major phthalates used in industry, routes of environmental contamination, evidences for health hazards, routes for in situ and ex situ microbial degradation, bacterial pathways involved in the degradation, major enzymes involved in the degradation process, half-lives of phthalates in environments, etc. Briefly, this handy module would enable the readers, environmentalists and policy makers to understand the impact of phthalates on the environment and the biota, coupled with the concerted microbial efforts to alleviate the burden of ever increasing load posed by phthalates. Copyright © 2015 Elsevier B.V. All rights reserved.

Dose addition predicts the effects of a mixture of five phthalate esters to inhibit fetal testosterone production and gene expression, and postnatal reproductive development in the Sprague Dawley rat

EPA Science Inventory

Exposure to some phthalate esters (PE) during sexual differentiation induces reproductive malformations in male and female rats. In the fetal male, these lesions result from phthalate-induced reductions in testicular testosterone (T) production and insulin-like hormone 3 (insl3) ...

Pollution characteristics of volatile organic compounds, polycyclic aromatic hydrocarbons and phthalate esters emitted from plastic wastes recycling granulation plants in Xingtan Town, South China

NASA Astrophysics Data System (ADS)

Huang, De-Yin; Zhou, Shun-Gui; Hong, Wei; Feng, Wei-Feng; Tao, Liang

2013-06-01

With the aim to investigate the main pollution characteristics of exhaust gases emitted from plastic waste recycling granulation plants, mainly volatile organic compounds (VOCs), polycyclic aromatic hydrocarbons (PAHs) and phthalate esters (PAEs) were analyzed in Xingtan Town, the largest distribution center of plastic waste recycling in China. Both inside and outside the plants, the total concentrations of volatile monocyclic aromatic hydrocarbons (MAHs), PAHs and PAEs ranged from 2000 to 3000 μg m-3, 450 to 1200 ng m-3, and 200 to 1200 ng m-3, respectively. Their concentration levels inside the plants were higher than those outside the plants, and PAHs and PAEs were mainly distributed in the gas-phase. Notably, highly toxic benzo[a]pyrene (BaP) could be detected inside the plants, and harmful PAEs could be detected not only inside but also outside the plants, although PAEs are non-volatile. The exhaust gas composition and concentration were related to the plastic feedstock and granulation temperature.

Treatment of phthalic acid esters by electrocoagulation with stainless steel electrodes using dimethyl phthalate as a model compound.

PubMed

Kabdaşli, Işik; Keleş, Asuman; Olmez-Hanci, Tuğba; Tünay, Olcay; Arslan-Alaton, Idil

2009-11-15

In this study, treatment of phthalates by electrocoagulation employing stainless steel electrodes was investigated using dimethyl phthalate (DMP) as a model compound. DMP was completely destructed within 30 min up to the high initial concentration of 100mg/L while total mineralization was also obtained within a couple of hours. The applied current density of 22.5 mA/cm(2) and electrolyte (NaCl) concentrations varying between 1000 and 1500 mg/L as chloride resulted in the highest treatment performance. The initial solution pH (2-6) had practically no effect on the process efficiency. Desorption experiments and the reaction rates obtained for DMP, COD and TOC abatements appeared to be a strong evidence of an oxidative removal mechanism. DMP removal fitted first order kinetics. COD and TOC removals began after the total DMP removal and also fitted first order kinetics. Activated sludge inhibition experiments revealed that toxicity could be significantly reduced by electrocoagulation application.

Occurrence of phthalate esters in over-the-counter medicines from China and its implications for human exposure.

PubMed

Jia, Lu-Lu; Lou, Xiang-Ying; Guo, Ying; Leung, Kelvin Sze-Yin; Zeng, Eddy Y

2017-01-01

Food, air, personal care products and indoor dust have been recognized as the main routes of exposure to phthalates in Chinese population, but other sources may have been overlooked, e.g., medicines. To fill the knowledge gap, phthalate esters were measured in 96 over-the-counter medicines made in China, including selected 71 Chinese patented medicines and 25 western medicines. It was found that none of the medicines was free of phthalates. The mean concentrations of individual phthalates ranged from 0.001μg/g (dicyclohexyl phthalate) to 5.85μg/g (diethyl phthalate). Among 9 targeted phthalates, di-n-butyl phthalate was the dominant congener, accounting for >65% of the total phthalates in all medicine samples, followed by di-(2-ethylhexyl) phthalate and diethyl phthalate. Phthalates in medicines appeared to derive from gastroresistant film coatings, plastic packing materials or phthalate contaminated rural herbal plants (especially for Chinese patented medicines). Daily human exposure to phthalates was estimated for local patients for one treatment cycle (e.g., one week) based on suggested consumption dosage and phthalate concentrations. Almost all exposure levels were below the guidelines suggested by the United States Environmental Protection Agency or European Food Safety Authority, indicating low health risk with phthalates from consumption of the medicines. In addition, concentration levels of phthalates in patients would increase upon administration but are expected to decrease to the same values as those in patients before they took medicines in several days. Because the number of medicine samples was limited and the concentrations of phthalates varied in a large range, further investigations are needed to acquire more data for better assessment of human health effects for Chinese population. Capsule: Distribution of phthalate esters in over-the-counter medicines and related exposure for Chinese population are examined. Copyright © 2016 Elsevier Ltd. All rights reserved.

REPRODUCTIVE TOXICITY OF PHTHALATE ESTERS

EPA Science Inventory

Phthalate esters display several modes of toxicity in mammalian species. In the rat, in utero exposure at relatively low dosage levels disrupts development of the reproductive system of the male rat by altering fetal testis hormone production. This presentation is a review of t...

Effects of phthalic acid esters (PAEs) on the neonate and aspects of teratogenic actions.

PubMed Central

Thomas, J A; Wienckowski, D B; Gillies, B A; Thomas, M J; Youkilis, E J

1986-01-01

A review of the literature reveals that several different phthalic acid esters (PAEs) are capable of causing testicular damage. Phthalate-induced zinc deficiency is consistent with germinal epithelial damage. Among experimental animals, mice perhaps show the greatest sensitivity to phthalate-induced terata, but high doses/exposure are required. Little toxicologic information is available with regard to phthalate-induced effects upon the neonate. PMID:3709448

Presence of phthalate esters in intravenous solution evaluated using gas chromatography-mass spectrometry method.

PubMed

Strac, Ivona Vidić; Pušić, Maja; Gajski, Goran; Garaj-Vrhovac, Vera

2013-03-01

Di-(2-ethylhexyl) phthalate (DEHP) is a plasticizer widely used in the production of poly-(vinyl) chloride (PVC) materials. It is a reproductive and developmental toxicant in animals and a suspected endocrine modulator in humans. DEHP is not covalently bound within the PVC molecule, which is why migration into a suitable medium can be expected. Since application of infusion solutions is one of the most common medical treatments, the objective of this study was to determine the migration of phthalates from softened PVC storage bags into infusion solution in different time periods within one year from date of production using a gas chromatography-mass spectrometry method. The measured values of DEHP ranged between 0.22 and 14.00 µg l(-1) , but the unexpected presence of other phthalate esters was also detected. It was concluded that values obtained in infusion solutions match the reference data and represent a minor risk for the patient. The presence of other phthalate esters leads to the conclusion that the pharmacopeic requirement for polymer cleanness was not fully met. Since phthalate esters are among the most extensively used industrial chemicals and are widely distributed in the environment, special precautions and further monitoring should be conducted to minimize any possible health risks. Copyright © 2011 John Wiley & Sons, Ltd.

Magnetic covalent triazine framework for rapid extraction of phthalate esters in plastic packaging materials followed by gas chromatography-flame ionization detection.

PubMed

Yan, Zijun; He, Man; Chen, Beibei; Gui, Bo; Wang, Cheng; Hu, Bin

2017-11-24

Covalent triazine frameworks (CTFs), featuring with high surface area, good thermal, chemical and mechanical stability, are good adsorbents in sample pretreatment. Herein, magnetic CTFs/Ni composite was prepared by in situ reduction of nickel ions on CTFs matrix with a solvothermal method. The prepared CTFs/Ni composite exhibited good preparation reproducibility, high chemical stability, and high extraction efficiency for targeted phthalate esters (PAEs) due to π-π interaction and hydrophobic effect. The porous structure of CTFs/Ni composite benefited the fast transfer of target PAEs from aqueous solution to the adsorbents, and the integrated magnetism contributed to the rapid separation of adsorbents from sample and elution solution. Based on it, a novel method of magnetic solid phase extraction (MSPE) combined with gas chromatography-flame ionization detector (GC-FID) was developed for the analysis of PAEs including dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DBP), benzyl butyl phthalate (BBP), di-2-ethylhexl phthalate (DEHP), and di-n-octyl phthalate (DNOP) in plastic packaging materials. Under the optimal experimental conditions, the limits of detection (LODs, S/N=3) for six PAEs were found to be in the range of 0.024-0.085mg/kg. The linear range was 0.32-16mg/kg for DMP, DEP, 0.08-80mg/kg for DBP, 0.16-32mg/kg for BBP, DEHP, and 0.32-32mg/kg for DNOP, respectively. The enrichment factors ranged from 59 to 88-fold (theoretical enrichment factor was 133-fold). The proposed method was successfully applied to the analysis of PAEs in various plastic packaging materials with recoveries in the range of 70.6-119% for the spiked samples. This method is characterized with short operation time, high sensitivity, low consumption of harmful organic solvents and can be extended to the analysis of other trace aromatic compounds. Copyright © 2017 Elsevier B.V. All rights reserved.

Association of phthalate esters with endometriosis in Indian women.

PubMed

Reddy, B S; Rozati, R; Reddy, B V R; Raman, N V V S S

2006-05-01

To evaluate the possible association between phthalate esters (PEs) and the occurrence of endometriosis. Case-control study. Department of Reproductive Medicine, Bhagawan Mahavir Medical Research Centre, Maternal Health and Reproductive Institute and Department of Analytical R&D, Hetero Research Foundation, Hyderabad, Andhra Pradesh, India. Blood samples were collected from 49 infertile women with endometriosis (study group); 38 age-matched women without endometriosis (control group I) but with infertility related to tubal defects, fibroids, polycystic ovaries, idiopathic infertility and pelvic inflammatory diseases diagnosed by laparoscopy and a further group of 21 age-matched women (control group II) with proven fertility and no evidence of endometriosis and other gynaecological disorders during laparoscopic sterilisation. Concentrations of PEs were measured using gas chromatography. Evaluation of PEs concentrations in women with endometriosis compared with women free from the disease. Women with endometriosis showed significantly higher concentrations of di-n-butyl phthalate (DnBP), butyl benzyl phthalate (BBP), di-n-octyl phthalate (DnOP) and diethyl hexyl phthalate (DEHP) (mean 0.44 [SD 0.41]; 0.66 [SD 0.61]; 3.32 [SD 2.17]; 2.44 [SD 2.17] micrograms/ml) compared with control group I (mean 0.08 [SD 0.14]; 0.12 [SD 0.20]; 0; 0.50 [SD 0.80] micrograms/ml) and control group II (mean 0.15 [SD 0.21]; 0.11 [SD 0.22]; 0; 0.45 [SD 0.68] micrograms/ml). The correlation between the concentrations of PEs and different severity of endometriosis was strong and statistically significant at P < 0.05 for all four compounds (DnBP: r=+0.73, P < 0.0001; BBP: r=+0.78, P < 0.0001; DnOP: r=+0.57, P < 0.0001 and DEHP: r=+0.44, P < 0.0014). This study suggests that PEs may have an aetiological association with endometriosis.

Electrochemical impedance spectroscopy based MEMS sensors for phthalates detection in water and juices

NASA Astrophysics Data System (ADS)

Zia, Asif I.; Mohd Syaifudin, A. R.; Mukhopadhyay, S. C.; Yu, P. L.; Al-Bahadly, I. H.; Gooneratne, Chinthaka P.; Kosel, Jǘrgen; Liao, Tai-Shan

2013-06-01

Phthalate esters are ubiquitous environmental and food pollutants well known as endocrine disrupting compounds (EDCs). These developmental and reproductive toxicants pose a grave risk to the human health due to their unlimited use in consumer plastic industry. Detection of phthalates is strictly laboratory based time consuming and expensive process and requires expertise of highly qualified and skilled professionals. We present a real time, non-invasive, label free rapid detection technique to quantify phthalates' presence in deionized water and fruit juices. Electrochemical impedance spectroscopy (EIS) technique applied to a novel planar inter-digital (ID) capacitive sensor plays a vital role to explore the presence of phthalate esters in bulk fluid media. The ID sensor with multiple sensing gold electrodes was fabricated on silicon substrate using micro-electromechanical system (MEMS) device fabrication technology. A thin film of parylene C polymer was coated as a passivation layer to enhance the capacitive sensing capabilities of the sensor and to reduce the magnitude of Faradic current flowing through the sensor. Various concentrations, 0.002ppm through to 2ppm of di (2-ethylhexyl) phthalate (DEHP) in deionized water, were exposed to the sensing system by dip testing method. Impedance spectra obtained was analysed to determine sample conductance which led to consequent evaluation of its dielectric properties. Electro-chemical impedance spectrum analyser algorithm was employed to model the experimentally obtained impedance spectra. Curve fitting technique was applied to deduce constant phase element (CPE) equivalent circuit based on Randle's equivalent circuit model. The sensing system was tested to detect different concentrations of DEHP in orange juice as a real world application. The result analysis indicated that our rapid testing technique is able to detect the presence of DEHP in all test samples distinctively.

The Human Health Assessment to Phthalate Acid Esters (PAEs) and Potential Probability Prediction by Chromophoric Dissolved Organic Matter EEM-FRI Fluorescence in Erlong Lake.

PubMed

Ji, Meichen; Li, Sijia; Zhang, Jiquan; Di, Hui; Li, Fengxu; Feng, Tianji

2018-05-29

Phthalate acid esters (PAEs) are suspected to cause wide environmental pollution and have adverse effects on human health. Three priority control phthalates, namely dimethyl phthalate (DMP), diethyl phthalate (DEP), and dibutyl phthalate (DBP), were determined in 45 water samples from the largest drinking water source in Jilin Province. Chromophoric-dissolved organic matter (CDOM), which are composed of complex compounds and are a proxy for water quality, can be monitored using a fluorometer. This study attempted to understand the correlations of the CDOM fluorescence regional integration (FRI) components with PAEs and CDOM characteristics under seasonal and spatial variations in the Erlong Lake. The characteristics of the CDOM absorption parameters in different water samples showed a higher aromatic content and molecular weight in October because of increased terrestrial inputs. The Σ3PAEs concentrations ranged from 0.231 mg L -1 to 0.435 mg L -1 in water, and DEP contributed to more than 90% of the Σ3PAEs. The FRI method identified five fluorescence components: one tyrosine-like (R1), one tryptophan-like (R2), one fulvic-like (R3), one microbial protein-like (R4), and one humic-like (R5) component. However, significant relationships exist between DEP and R3 ( R ² = 0.78, p < 0.001), R4 ( R² = 0.77, p < 0.001), and R5 ( R ² = 0.58, p < 0.001). Quantifying the relationship between CDOM and PAEs was highly significant, because the results will simplify the componential analysis of pollutants from a spatiotemporal perspective as compared to traditional chemical measurements. The human health risk assessment results revealed no human health risk ( HQ < 1) in the Erlong Lake basin.

Photocatalytic degradation properties of α-Fe2O3 nanoparticles for dibutyl phthalate in aqueous solution system

NASA Astrophysics Data System (ADS)

Liu, Yue; Sun, Nan; Hu, Jianshe; Li, Song; Qin, Gaowu

2018-04-01

The phthalate ester compounds in industrial wastewater, as kinds of environmental toxic organic pollutants, may interfere with the body's endocrine system, resulting in great harm to humans. In this work, the photocatalytic degradation properties of dibutyl phthalate (DBP) were investigated using α-Fe2O3 nanoparticles and H2O2 in aqueous solution system. The optimal parameters and mechanism of degradation were discussed by changing the morphology and usage amount of catalysts, the dosage of H2O2, pH value and the initial concentration of DBP. Hollow α-Fe2O3 nanoparticles showed the highest degradation efficiency when 30 mg of catalyst and 50 µl of H2O2 were used in the DBP solution with the initial concentration of 13 mg l-1 at pH = 6.5. When the reaction time was 90 min, DBP was degraded 93% for the above optimal parameters. The photocatalytic degradation mechanism of DBP was studied by the gas chromatography-mass spectrometry technique. The result showed that the main degradation intermediates of DBP were ortho-phthalate monobutyl ester, methyl benzoic acid, benzoic acid, benzaldehyde, and heptyl aldehyde when the reaction time was 2 h. DBP and its intermediates were almost completely degraded to CO2 and H2O in 12 h in the α-Fe2O3/ H2O2/UV system.

Thyroid hormone disrupting activities associated with phthalate esters in water sources from Yangtze River Delta.

PubMed

Shi, Wei; Zhang, Feng-Xian; Hu, Guan-Jiu; Hao, Ying-Qun; Zhang, Xiao-Wei; Liu, Hong-Ling; Wei, Si; Wang, Xin-Ru; Giesy, John P; Yu, Hong-Xia

2012-07-01

Thyroid hormone disrupting compounds in water sources is a concern. Thyroid hormone (TH) agonist and antagonist activities of water sources from the Yangtze River, Huaihe River, Taihu Lake and ground water in the Yangtze River Delta region were evaluated by use of a TH reporter gene assay based on the green monkey kidney fibroblast (CV-1). While weak TH receptor (TR) agonist potency was observed in only one of 15 water sources, antagonist potency was present in most of the water sources. TR antagonist equivalents could be explained by the presence of dibutyl phthalate (DBP), with concentrations ranging from 2.8×10(1) to 1.6×10(3) μg DBP /L (ATR-EQ(50)s). None of the ground waters exhibited TH agonist potencies while all of the samples from Taihu Lake displayed notable TR antagonist potencies. To identify the responsible thyroid active compounds, instrumental analysis was conducted to measure a list of potential thyroid-disrupting chemicals, including organochlorine (OC) pesticides and phthalate esters. Combining the results of the instrumental analysis with those of the bioassay, DBP was determined to account for 17% to 144% of ATR-EQ(50)s in water sources. Furthermore, ATR-EQ(20-80) ranges for TR antagonist activities indicated that samples from locations WX-1 and WX-2 posed the greatest health concern and the associated uncertainty may warrant further investigation. Copyright © 2011 Elsevier Ltd. All rights reserved.

AN ASSESSMENT OF PHTHALATE ESTER TOXICITY TO FRESHWATER BENTHOS: 2. SEDIMENT EXPOSURES

EPA Science Inventory

Seven phthalate esters were evaluated for their stability and 10-d acute toxicity to the freshwater invertebrates Hyalella azteca and Chironomus tentans following incorporation into sediment. The chemicals were diethyl (DEP), di-n-butyl (DBP), di-n-hyxyl (DHP), di-[2-ethylhexyl] ...

Concentration and risk assessment of phthalates present in indoor air from newly decorated apartments

NASA Astrophysics Data System (ADS)

Pei, X. Q.; Song, M.; Guo, M.; Mo, F. F.; Shen, X. Y.

2013-04-01

Phthalate esters (PAEs) are ubiquitous in the indoor environment, owing to their use in consumer products. People spend a considerable amount of time indoors. As a result, human exposure to indoor contaminants is of great concern. People are exposed to phthalates through inhalation and dermal absorption of indoor air. In this study, the concentrations, characteristics and carcinogenic risks of gas-phase and particle-phase phthalates in indoor air from bedroom, living room and study room of 10 newly decorated apartments in Hangzhou, China were first investigated. The mean concentration of phthalates (gas-phase and particle-phase) present in household air was 12 096.4 ng m-3, of which diethyl phthalate (DEP), butylbenzyl phthalate (BBP) and di(2-ethylhexyl) phthalate (DEHP) were the most abundant compounds with concentrations of 2290 ng m-3, 3975 ng m-3 and 2437 ng m-3, respectively, totally accounting for 72.0% of ∑6PAEs. Contamination levels of phthalates varied in different compartments. The concentration of phthalates was the highest 17 363.7 ng m-3 in living room, followed with 11 389.5 ng m-3 in study room, and the lowest 9739.1 ng m-3 in bedroom. It was also found that phthalates mainly accumulated in gaseous form in household air. DEHP posed the greatest health risk to children aged 1-2. Carcinogenic risk of DEHP was evaluated to be 3.912 × 10-5, and was 39 times higher than the limit set by the U.S. EPA.

Organophosphate and phthalate esters in indoor air: a comparison between multi-storey buildings with high and low prevalence of sick building symptoms.

PubMed

Bergh, Caroline; Magnus Åberg, K; Svartengren, Magnus; Emenius, Gunnel; Östman, Conny

2011-07-01

An extensive study has been conducted on the prevalence of organophosphorous flame retardants/plasticizers and phthalate ester plasticizers in indoor air. The targeted substances were measured in 45 multi-storey apartment buildings in Stockholm, Sweden. The apartment buildings were classified as high or low risk with regard to the reporting of sick building symptoms (SBS) within the project Healthy Sustainable Houses in Stockholm (3H). Air samples were taken from two to four apartments per building (in total 169 apartments) to facilitate comparison within and between buildings. Association with building characteristics has been examined as well as association with specific sources by combining chemical analysis and exploratory uni- and multivariate data analysis. The study contributes to the overall perspective of levels of organophosphate and phthalate ester in indoor air enabling comparison with other studies. The results indicated little or no difference in the concentrations of the target substances between the two risk classifications of the buildings. The differences between the apartments sampled within (intra) buildings were greater than the differences between (inter) buildings. The concentrations measured in air ranged up to 1200 ng m(-3) for organophosphate esters and up to 11 000 ng m(-3) for phthalate esters. Results in terms of sources were discerned e.g. PVC flooring is a major source of benzylbutyl phthalate in indoor air.

CUMULATIVE EFFECTS OF DIBUTYL PHTHALATE AND DIETHYLHEXYL PHTHALATE ON MALE RAT REPRODUCTIVE TRACT DEVELOPMENT: ALTERED FETAL STEROID HORMONES AND GENES.

EPA Science Inventory

Exposure to the plasticizers diethylhexyl phthalate (DEHP) and di(n-butyl) phthalate (DBP) during sexual differentiation causes male reproductive tract malformations in rats and rabbits. In the fetal male rat, these two phthalate esters decrease testosterone (T) production and i...

In vitro assessment of phthalate acid esters-trypsin complex formation.

PubMed

Chi, Zhenxing; Zhao, Jing; Li, Weiguo; Araghi, Arash; Tan, Songwen

2017-10-01

In this work, interactions of three phthalate acid esters (PAEs), including dimethyl phthalate (DMP), diethyl phthalate (DEP) and dibutyl phthalate (DBP), with trypsin have been studied in vitro, under simulated physiological conditions using multi-spectroscopic techniques and molecular modeling. The results show that these PAEs can bind to the trypsin, forming trypsin-PAEs complexes, mainly via hydrophobic interactions, with the affinity order of DMP > DEP > DBP. Binding to the PAEs is found to result in molecular deformation of trypsin. The modeling results suggest that only DBP can bind with the amino acid residues of the catalytic triad and S1 binding pocket of trypsin, leading to potential competitive enzyme inhibition. Copyright © 2017 Elsevier Ltd. All rights reserved.

Effects of six priority controlled phthalate esters with long-term low-dose integrated exposure on male reproductive toxicity in rats.

PubMed

Gao, Hai-Tao; Xu, Run; Cao, Wei-Xin; Qian, Liang-Liang; Wang, Min; Lu, Lingeng; Xu, Qian; Yu, Shu-Qin

2017-03-01

Human beings are inevitably exposed to ubiquitous phthalate esters (PEs) surroundings. The purposes of this study were to investigate the effects of long-term low-dose exposure to the mixture of six priority controlled phthalate esters (MIXPs): dimethyl phthalate (DMP), diethyl phthalate (DEP), di(n-butyl) phthalate (DBP), butyl benzyl phthalate (BBP), di(2-ethyhexyl) phthalate (DEHP) and di-n-octyl phthalate (DNOP), on male rat reproductive system and further to explore the underlying mechanisms of the reproductive toxicity. The male rats were orally exposed to either sodium carboxymethyl cellulose as controls or MIXPs at three different low-doses by gavage for 15 weeks. Testosterone and luteinizing hormone (LH) in serum were analyzed, and pathological examinations were performed for toxicity evaluation. Steroidogenic proteins (StAR, P450scc, CYP17A1 and 17β-HSD), cell cycle and apoptosis-related proteins (p53, Chk1, Cdc2, CDK6, Bcl-2 and Bax) were measured for mechanisms exploration. MIXPs with long-term low-dose exposure could cause male reproductive toxicity to the rats, including the decrease of both serum and testicular testosterone, and the constructional damage of testis. These effects were related to down-regulated steroidogenic proteins, arresting cell cycle progression and promoting apoptosis in rat testicular cells. The results indicate that MIXPs with long-term low-dose exposure may pose male reproductive toxicity in human. Copyright © 2017 Elsevier Ltd. All rights reserved.

Dummy molecularly imprinted microbeads as solid-phase extraction material for selective determination of phthalate esters in water.

PubMed

Özer, Elif Tümay; Osman, Bilgen; Yazıcı, Tuğçe

2017-06-02

The aim of this study was to investigate the usability of newly synthesized dummy molecularly imprinted microbeads (DMIMs) as a solid phase extraction (SPE) material to determine six phthalate esters (PEs) in water by GC-MS analysis. Diethyl phthalate (DEP) was used as a dummy template to prepare poly(ethylene glycol dimethacrylate N-methacryloyl-l-tryptophan methyl ester) [PEMATrp)] DMIMs by using suspension polymerization. The PEMATrp DMIMs were characterized by using Fourier transform infrared spectroscopy (FTIR), X-ray photoelectron spectroscopy (XPS) and scanning electron microscopy (SEM). Firstly, the adsorption capacities of the DMIMs prepared in different template molecule (DEP) to functional monomer (MATrp) ratios were investigated by using DEP solutions in the concentration range of 1-500mg/L at pH 3.0. Styrene and vanillic acid were used to evaluate the selectivity of the prepared DMIMs towards the template molecule (DEP). Then, the best analytical conditions were investigated for the simultaneous determination of dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DBP), benzylbutyl phthalate (BBP), di-(2-ethylhexyl) phthalate (DEHP) and di-n-octyl phthalate (DnOP) in aqueous media by using the PEMATrp DMIMs as SPE material. Validation experiments showed that the PEMATrp DMIMs-SPE method had good linearity at 12.5-250.0μg/L (0.988-0.999), good precision (1.2-5.9%), and limits of detection in a range of 0.31-0.41μg/L. Copyright © 2017 Elsevier B.V. All rights reserved.

COMBINATION DOSE OF TWO PHTHALATES ADDITIVELY DEPRESSES TESTOSTERONE PRODUCTION AND INSL3 GENE EXPRESSION IN MALE RAT FETUSES

EPA Science Inventory

Diethylhexyl phthalate (DEHP) and di(n-butyl) phthalate (DBP) are phthalate esters used to modify plastic and polymer textures. Individually,DEHP and DBP reduce testosterone production, inhibit reproductive tract development, andinduce reproductive organ malformationsin male rats...

75 FR 20785 - Polyglyceryl Phthalate Ester of Coconut Oil Fatty Acids; Exemption from the Requirement of a...

Federal Register 2010, 2011, 2012, 2013, 2014

2010-04-21

...EPA issued a final rule in the Federal Register of July 8, 2009, concerning polyglyceryl phthalate ester of coconut oil fatty acids; exemption from the requirement of a tolerance. This document is being issued to correct the inert ingredient name and CAS numbers.

STRUCTURE ACTIVITY RELATIONSHIP OF PHTHALATE ESTERS TO INHIBITED FETAL TESTICULAR TESTOSTERONE PRODUCTION IN THE SPRAGUE DAWLEY RAT

EPA Science Inventory

Several of the phthalate esters (widely used as plasticizers of polyvinyl chloride and other applications) have been shown to inhibit fetal testicular testosterone (T) production and Insl3 mRNA in the laboratory rat. The current study was designed to define the dose response of 7...

Determination of phthalic acid esters in different baby food samples by gas chromatography tandem mass spectrometry.

PubMed

Socas-Rodríguez, Bárbara; González-Sálamo, Javier; Herrera-Herrera, Antonio V; Santana-Mayor, Álvaro; Hernández-Borges, Javier

2018-03-09

In this work, a new method has been developed for the determination of 14 phthalic acid esters (i.e., benzylbutyl phthalate (BBP), bis-2-n-butoxyethyl phthalate (DBEP), dibutyl phthalate (DBP), dicyclohexyl phthalate (DCHP), bis-2-ethoxyethyl phthalate (DEEP), diethyl phthalate (DEP), diisodecyl phthalate (DIDP), diisononyl phthalate (DINP), bis-isopentyl phthalate (DIPP), bis (2-methoxyethyl) phthalate (DMEP), dimethyl phthalate (DMP), di-n-octyl phthalate (DNOP), bis-n-pentyl phthalate (DNPP), dipropyl phthalate (DPP)) and one adipate (bis (2-ethylhexyl) adipate (DEHA)) in different baby foods. Separation was carried out by gas chromatography triple quadrupole tandem mass spectrometry while the previous extraction of the samples was carried out using the QuEChERS method. The methodology was validated for four baby food samples (two fruit compotes of different compositions and two meat and fish purees with vegetables) using dibutyl phthalate-3,4,5,6-d 4 (DBP-d 4 ) as internal standard. Determination coefficients (R 2 ) of matrix-matched calibration curves were above 0.9922 in all cases while relative recovery values ranged between 70 and 120%, with relative standard deviation values below 19%. The limits of quantification of the method ranged between 0.03 and 1.11 μg/kg. Finally, the analysis of commercially available samples was carried out finding the presence of BBP, DEHA, DEP, DIDP, and DPP in some of the studied samples.

COMBINATION DOSE OF TWO PHTHALATES ADDITIVELY DEPRESSES TESTOSTERONE PRODUCTION AND INSL3 GENE EXPRESSION IN MALE RAT FETUSES

EPA Science Inventory

Diethylhexyl phthalate (DEHP) and di(n-butyl) phthalate (DBP) are phthalate esters used to modify plastic and polymer textures. Individually,in uteroexposure to DEHP and DBP inhibit reproductive tract development,induce reproductive organ malformations, and reduce testosterone (T...

Photocatalytic degradation properties of α-Fe2O3 nanoparticles for dibutyl phthalate in aqueous solution system

PubMed Central

Liu, Yue; Sun, Nan; Hu, Jianshe; Li, Song; Qin, Gaowu

2018-01-01

The phthalate ester compounds in industrial wastewater, as kinds of environmental toxic organic pollutants, may interfere with the body's endocrine system, resulting in great harm to humans. In this work, the photocatalytic degradation properties of dibutyl phthalate (DBP) were investigated using α-Fe2O3 nanoparticles and H2O2 in aqueous solution system. The optimal parameters and mechanism of degradation were discussed by changing the morphology and usage amount of catalysts, the dosage of H2O2, pH value and the initial concentration of DBP. Hollow α-Fe2O3 nanoparticles showed the highest degradation efficiency when 30 mg of catalyst and 50 µl of H2O2 were used in the DBP solution with the initial concentration of 13 mg l−1 at pH = 6.5. When the reaction time was 90 min, DBP was degraded 93% for the above optimal parameters. The photocatalytic degradation mechanism of DBP was studied by the gas chromatography–mass spectrometry technique. The result showed that the main degradation intermediates of DBP were ortho-phthalate monobutyl ester, methyl benzoic acid, benzoic acid, benzaldehyde, and heptyl aldehyde when the reaction time was 2 h. DBP and its intermediates were almost completely degraded to CO2 and H2O in 12 h in the α-Fe2O3/ H2O2/UV system. PMID:29765674

Photocatalytic degradation properties of α-Fe2O3 nanoparticles for dibutyl phthalate in aqueous solution system.

PubMed

Liu, Yue; Sun, Nan; Hu, Jianshe; Li, Song; Qin, Gaowu

2018-04-01

The phthalate ester compounds in industrial wastewater, as kinds of environmental toxic organic pollutants, may interfere with the body's endocrine system, resulting in great harm to humans. In this work, the photocatalytic degradation properties of dibutyl phthalate (DBP) were investigated using α-Fe 2 O 3 nanoparticles and H 2 O 2 in aqueous solution system. The optimal parameters and mechanism of degradation were discussed by changing the morphology and usage amount of catalysts, the dosage of H 2 O 2 , pH value and the initial concentration of DBP. Hollow α-Fe 2 O 3 nanoparticles showed the highest degradation efficiency when 30 mg of catalyst and 50 µl of H 2 O 2 were used in the DBP solution with the initial concentration of 13 mg l -1 at pH = 6.5. When the reaction time was 90 min, DBP was degraded 93% for the above optimal parameters. The photocatalytic degradation mechanism of DBP was studied by the gas chromatography-mass spectrometry technique. The result showed that the main degradation intermediates of DBP were ortho -phthalate monobutyl ester, methyl benzoic acid, benzoic acid, benzaldehyde, and heptyl aldehyde when the reaction time was 2 h. DBP and its intermediates were almost completely degraded to CO 2 and H 2 O in 12 h in the α-Fe 2 O 3 / H 2 O 2 /UV system.

[Toxicity effects of phthalate substitute plasticizers used in toys].

PubMed

Hirata-Koizumi, Mutsuko; Takahashi, Mika; Matsumoto, Mariko; Kawamura, Tomoko; Ono, Atsushi; Hirose, Akihiko

2012-01-01

Phthalate esters are widely used as plasticizers in polyvinyl chloride products. Because of human health concerns, regulatory authorities in Japan, US, Europe and other countries control the use of di(2-ethylhexyl) phthalate, diisononyl phthalate, di-n-butyl phthalate, butylbenzyl phthalate, diisodecyl phthalate and di-n-octyl phthalate for the toys that can be put directly in infants' mouths. While these regulatory actions will likely reduce the usage of phthalate esters, there is concern that other plasticizers that have not been sufficiently evaluated for safety will be used more frequently. We therefore collected and evaluated the toxicological information on di(2-ethylhexyl) terephthalate (DEHT), 1,2-cyclohexanedicarboxylic acid, diisononyl ester (DINCH), diisononyl adipate (DINA), 2,2,4-trimetyl-1,3-pentanediol diisobutyrate (TXIB), tri-n-butyl citrate (TBC) and acetyl tri-n-butyl citrate (ATBC) which were detected at a relatively high frequency in toys. The collected data have shown that chronic exposure to DEHT affects the eye and nasal turbinate, and DINCH exerts effects on the thyroid and kidney in rats. DINA and TXIB have been reported to have hepatic and renal effects in dogs or rats, and ATBC slightly affected the liver in rats. The NOAELs for repeated dose toxicity are relatively low for DINCH (40 mg/kg bw/day) and TXIB (30 mg/kg bw/day) compared with DEHT, DINA and ATBC. DEHT, TXIB and ATBC have been reported to have reproductive/developmental effects at relatively high doses in rats. For DINA and TBC, available data are insufficient for assessing the hazards, and therefore, adequate toxicity studies should be conducted. In the present review, the toxicity information on 6 alternatives to phthalate plasticizers is summarized, focusing on the effects after oral exposure, which is the route of most concern.

PHTHALATE ESTER-INDUCED MALFORMATIONS ARE ASSOCIATED WITH CHANGES IN GENE EXPRESSION AND STEROID HORMONE PRODUCTION IN THE FETAL RAT TESTIS DURING SEXUAL DIFFERENTIATION

EPA Science Inventory

Phthalate ester-induced gubernacular ligament lesions are associated with reduced Insl3 gene expression in the fetal rat testis during sexual differentiation.
Vickie S Wilson, Christy Lambright, Johnathan Furr, Joseph Ostby, Carmen Wood, Gary Held, L.Earl Gray Jr.
U.S. EPA,...

PHTHALATE ESTER-INDUCED GUBERNACULAR LIGAMENT LESIONS ARE ASSOCIATED WITH REDUCED INSL3 GENE EXPRESSION IN THE FETAL RAT TESTIS DURING SEXUAL DIFFERENTIATION

EPA Science Inventory

Phthalate ester-induced gubernacular ligament lesions are associated with reduced Insl3 gene expression in the fetal rat testis during sexual differentiation.
Vickie S Wilson, Christy Lambright, Johnathan Furr, Joseph Ostby, Carmen Wood, Gary Held, L.Earl Gray Jr.
U.S. EPA,...

PHTHALATE ESTER-INDUCED GUBERNACULAR LESIONS ARE ASSOCIATED WITH REDUCED INSL-3 GENE EXPRESSION IN THE FETAL RAT TESTIS

EPA Science Inventory

Phthalate ester-induced gubernacular ligament lesions are associated with reduced Insl3 gene expression in the fetal rat testis during sexual differentiation.
VS Wilson, C Lambright, J Furr, J Ostby, C Wood, G Held, LE Gray Jr.
U.S. EPA, ORD, NHEERL, Reproductive Toxicology...

USE OF LINEAR FREE ENERGY RELATIONSHIPS AND AN EVALUATIVE MODEL TO ASSESS THE FATE AND TRANSPORT OF PHTHALATE ESTERS IN THE AQUATIC ENVIRONMENT

EPA Science Inventory

Linear free energy relationships for selected phthalate esters were used to estimate the rate constants for hydrolysis, biolysis, sediment-water partition coefficients, and biosorption required for modeling. The fate and transport behavior of dimethyl, diethyl, di-n-butyl, di-n-o...

Slow-injection ultrasound-assisted emulsification-microextraction for determination of phthalate esters in water.

PubMed

Li, Songqing; Li, Tong; Gao, Peng; Lu, Runhua; Zhou, Wenfeng; Gao, Haixiang

2014-10-01

A type of ultrasound-assisted emulsification-microextraction (USAEME) was applied for the extraction and determination of four phthalate esters (e.g., dimethyl phthalate, diethyl phthalate, dibutyl phthalate and benzyl butyl phthalate) in aqueous samples prior to quantification using HPLC-UV. The simultaneous injection of the extraction solvent and ultrasonication of the mixture results in an efficient extraction with the extractant well-dispersed in the sample. The parameters affecting the experimental results were analyzed and optimized through the design of the experiment. Using a central composite face-centered design, the results of 28 experimental data points were analyzed and validated. An optimal set of operating conditions was obtained using 40 μL of 1,1,2,2-tetrachloroethane and 1% NaCl subjected to 2.0 min of ultrasonication under natural pH. Under optimized conditions, the extractions resulted in analyte recoveries of 75-87% and high enrichment factors of 356-415. The calibration curves were linear, and the correlation coefficients ranged from 0.9992 to 0.9997 at concentrations of 5 to 300 μg L(-1). The RSDs (n = 5) were 5.6-7.9%. The limits of detection for the four phthalate esters ranged from 0.26 to 1.46 μg L(-1). © The Author [2013]. Published by Oxford University Press. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

OCTANOL/WATER PARTITION COEFFICIENTS AND WATER SOLUBILITIES OF PHTHALATE ESTERS

EPA Science Inventory

Measurements of the octanol/water partition coefficients (K-ow) and water solubilities of di-n-octyl phthalate (DnOP) and di-n-decyl phthalate (DnDP) by the slow-stirring method are reported. The water solubility was also measured for di-n-hexyl phthalate (DnHP). The log K-ow val...

Occurrence and environmental risk assessment of PAEs in Weihe River near Xi'an City, China.

PubMed

Guo, Xiaofeng; Wang, Lei; Wang, Xudong; Liu, Hanli

2013-01-01

The occurrence and distribution of phthalate acid esters (PAEs) in surface water of the Weihe River basin (eight mainstream sampling points and 15 tributary sampling points) in the Shaanxi section were investigated during the dry season, level period (spring), wet season and level period (autumn). The PAEs tested for were diethyl phthalate (DEP), di-n-butyl phthalate (DBP), dicyclohexyl phthalate (DCHP) and di-(2-ethylhexyl) phthalate (DEHP). The testing proceeded by millipore filtration, then solid phase extraction and then gas chromatography-mass spectrometry determination for all examined PAEs. The monitoring results indicated that, in terms of seasonal changes, concentration of the PAEs in the mainstream is: Dry season > Level period (spring) > Wet season ≈ Level period (autumn). An environmental risk assessment was then performed on PAE pollution levels of the Weihe River basin. This paper employed a risk assessment methodology to evaluate the potential adverse health effects of the individual PAE compounds according to their carcinogenicities. For DEP, DBP and DEHP, a low Risk Index (all of them were lower than the specified level of 1.0) reveals that small non-carcinogenic risks exist resulting from the presence of trace concentrations in the surface water of the Weihe River basin.

In utero treatment with the herbicide linuron produces male rat reproductive malformations similar to the phthalate esters but through a different mechanism of action.

EPA Science Inventory

Although linuron has been reported to act as an androgen receptor (AR) antagonist, the suite of malformations observed in male rat offspring after in utero exposure differs from that of other AR antagonists and more closely resembles that produced by phthalate esters (PE) such as...

A mixture of five phthalate esters inhibits fetal testicular testosterone production in a cummulative manner consistent with their predicted reproductive toxicity in the Sprague Dawley rat

EPA Science Inventory

Phthalate diesters are plasticizers to which humans are ubiquitously exposed. Exposure to certain phthalates during sexual differentiation causes reproductive tract malformations in male rats. In the fetal rat, exposure to the phthalates benzylbutyl (BBP), di(n)butyl (DBP), and...

27 CFR 21.106 - Diethyl phthalate.

Code of Federal Regulations, 2011 CFR

2011-04-01

... 27 Alcohol, Tobacco Products and Firearms 1 2011-04-01 2011-04-01 false Diethyl phthalate. 21.106....106 Diethyl phthalate. (a) Refractive index at 25 °C. 1.497 to 1.502. (b) Color. Colorless. (c) Odor... °/25 °C. 1.115 to 1.118. (f) Ester content (as diethyl phthalate). Not less than 99 percent by weight...

27 CFR 21.106 - Diethyl phthalate.

Code of Federal Regulations, 2014 CFR

2014-04-01

... 27 Alcohol, Tobacco Products and Firearms 1 2014-04-01 2014-04-01 false Diethyl phthalate. 21.106....106 Diethyl phthalate. (a) Refractive index at 25 °C. 1.497 to 1.502. (b) Color. Colorless. (c) Odor... °/25 °C. 1.115 to 1.118. (f) Ester content (as diethyl phthalate). Not less than 99 percent by weight...

27 CFR 21.106 - Diethyl phthalate.

Code of Federal Regulations, 2010 CFR

2010-04-01

... 27 Alcohol, Tobacco Products and Firearms 1 2010-04-01 2010-04-01 false Diethyl phthalate. 21.106....106 Diethyl phthalate. (a) Refractive index at 25 °C. 1.497 to 1.502. (b) Color. Colorless. (c) Odor... °/25 °C. 1.115 to 1.118. (f) Ester content (as diethyl phthalate). Not less than 99 percent by weight...

27 CFR 21.106 - Diethyl phthalate.

Code of Federal Regulations, 2012 CFR

2012-04-01

... 27 Alcohol, Tobacco Products and Firearms 1 2012-04-01 2012-04-01 false Diethyl phthalate. 21.106....106 Diethyl phthalate. (a) Refractive index at 25 °C. 1.497 to 1.502. (b) Color. Colorless. (c) Odor... °/25 °C. 1.115 to 1.118. (f) Ester content (as diethyl phthalate). Not less than 99 percent by weight...

Soil contamination by phthalate esters in Chinese intensive vegetable production systems with different modes of use of plastic film.

PubMed

Wang, Jun; Luo, Yongming; Teng, Ying; Ma, Wenting; Christie, Peter; Li, Zhengao

2013-09-01

The concentrations of six priority phthalic acid esters (PAEs) in intensively managed suburban vegetable soils in Nanjing, east China, were analyzed using gas chromatography-mass spectrometry (GC-MS). The total PAE concentrations in the soils ranged widely from 0.15 to 9.68 mg kg(-1) with a median value of 1.70 mg kg(-1), and di-n-butyl phthalate (DnBP), bis-(2-ethylhexyl) phthalate (DEHP) and di-n-octyl phthalate (DnOP) were the most abundant phthalate esters. Soil PAE concentrations depended on the mode of use of plastic film in which PAEs were incorporated as plasticizing agents and both the plastic film and poultry manure appeared to be important sources of soil PAEs. Vegetables in rotation with flooded rice led to lower concentrations of PAEs in soil. The results indicate that agricultural plastic film can be an important source of soil PAE contamination and further research is required to fully elucidate the mechanisms of PAE contamination of intensive agricultural soils with different use modes of use of plastic film. Crown Copyright © 2013. Published by Elsevier Ltd. All rights reserved.

Performance, kinetic, and biodegradation pathway evaluation of anaerobic fixed film fixed bed reactor in removing phthalic acid esters from wastewater

NASA Astrophysics Data System (ADS)

Ahmadi, Ehsan; Yousefzadeh, Samira; Ansari, Mohsen; Ghaffari, Hamid Reza; Azari, Ali; Miri, Mohammad; Mesdaghinia, Alireza; Nabizadeh, Ramin; Kakavandi, Babak; Ahmadi, Peyman; Badi, Mojtaba Yegane; Gholami, Mitra; Sharafi, Kiomars; Karimaei, Mostafa; Ghoochani, Mahboobeh; Brahmand, Masoud Binesh; Mohseni, Seyed Mohsen; Sarkhosh, Maryam; Rezaei, Soheila; Asgharnia, Hosseinali; Dehghanifard, Emad; Jafari, Behdad; Mortezapour, Alireza; Moghaddam, Vahid Kazemi; Mahmoudi, Mohammad Molla; Taghipour, Nader

2017-02-01

Emerging and hazardous environmental pollutants like phthalic acid esters (PAEs) are one of the recent concerns worldwide. PAEs are considered to have diverse endocrine disrupting effects on human health. Industrial wastewater has been reported as an important environment with high concentrations of PAEs. In the present study, four short-chain PAEs including diallyl phthalate (DAP), diethyl phthalate (DEP), dimethyl phthalate (DMP), and phthalic acid (PA) were selected as a substrate for anaerobic fixed film fixed bed reactor (AnFFFBR). The process performances of AnFFFBR, and also its kinetic behavior, were evaluated to find the best eco-friendly phthalate from the biodegradability point of view. According to the results and kinetic coefficients, removing and mineralizing of DMP occurred at a higher rate than other phthalates. In optimum conditions 92.5, 84.41, and 80.39% of DMP, COD, and TOC were removed. DAP was found as the most bio-refractory phthalate. The second-order (Grau) model was selected as the best model for describing phthalates removal.

Performance, kinetic, and biodegradation pathway evaluation of anaerobic fixed film fixed bed reactor in removing phthalic acid esters from wastewater.

PubMed

Ahmadi, Ehsan; Yousefzadeh, Samira; Ansari, Mohsen; Ghaffari, Hamid Reza; Azari, Ali; Miri, Mohammad; Mesdaghinia, Alireza; Nabizadeh, Ramin; Kakavandi, Babak; Ahmadi, Peyman; Badi, Mojtaba Yegane; Gholami, Mitra; Sharafi, Kiomars; Karimaei, Mostafa; Ghoochani, Mahboobeh; Brahmand, Masoud Binesh; Mohseni, Seyed Mohsen; Sarkhosh, Maryam; Rezaei, Soheila; Asgharnia, Hosseinali; Dehghanifard, Emad; Jafari, Behdad; Mortezapour, Alireza; Moghaddam, Vahid Kazemi; Mahmoudi, Mohammad Molla; Taghipour, Nader

2017-02-20

Emerging and hazardous environmental pollutants like phthalic acid esters (PAEs) are one of the recent concerns worldwide. PAEs are considered to have diverse endocrine disrupting effects on human health. Industrial wastewater has been reported as an important environment with high concentrations of PAEs. In the present study, four short-chain PAEs including diallyl phthalate (DAP), diethyl phthalate (DEP), dimethyl phthalate (DMP), and phthalic acid (PA) were selected as a substrate for anaerobic fixed film fixed bed reactor (AnFFFBR). The process performances of AnFFFBR, and also its kinetic behavior, were evaluated to find the best eco-friendly phthalate from the biodegradability point of view. According to the results and kinetic coefficients, removing and mineralizing of DMP occurred at a higher rate than other phthalates. In optimum conditions 92.5, 84.41, and 80.39% of DMP, COD, and TOC were removed. DAP was found as the most bio-refractory phthalate. The second-order (Grau) model was selected as the best model for describing phthalates removal.

Performance, kinetic, and biodegradation pathway evaluation of anaerobic fixed film fixed bed reactor in removing phthalic acid esters from wastewater

PubMed Central

Ahmadi, Ehsan; Yousefzadeh, Samira; Ansari, Mohsen; Ghaffari, Hamid Reza; Azari, Ali; Miri, Mohammad; Mesdaghinia, Alireza; Nabizadeh, Ramin; Kakavandi, Babak; Ahmadi, Peyman; Badi, Mojtaba Yegane; Gholami, Mitra; Sharafi, Kiomars; Karimaei, Mostafa; Ghoochani, Mahboobeh; Brahmand, Masoud Binesh; Mohseni, Seyed Mohsen; Sarkhosh, Maryam; Rezaei, Soheila; Asgharnia, Hosseinali; Dehghanifard, Emad; Jafari, Behdad; Mortezapour, Alireza; Moghaddam, Vahid Kazemi; Mahmoudi, Mohammad Molla; Taghipour, Nader

2017-01-01

Emerging and hazardous environmental pollutants like phthalic acid esters (PAEs) are one of the recent concerns worldwide. PAEs are considered to have diverse endocrine disrupting effects on human health. Industrial wastewater has been reported as an important environment with high concentrations of PAEs. In the present study, four short-chain PAEs including diallyl phthalate (DAP), diethyl phthalate (DEP), dimethyl phthalate (DMP), and phthalic acid (PA) were selected as a substrate for anaerobic fixed film fixed bed reactor (AnFFFBR). The process performances of AnFFFBR, and also its kinetic behavior, were evaluated to find the best eco-friendly phthalate from the biodegradability point of view. According to the results and kinetic coefficients, removing and mineralizing of DMP occurred at a higher rate than other phthalates. In optimum conditions 92.5, 84.41, and 80.39% of DMP, COD, and TOC were removed. DAP was found as the most bio-refractory phthalate. The second-order (Grau) model was selected as the best model for describing phthalates removal. PMID:28216654

Validation of an automated counting procedure for phthalate-induced testicular multinucleated germ cells

EPA Science Inventory

In utero exposure to certain phthalate esters results in testicular toxicity, characterized at the tissue level by induction of multinucleated germ cells (MNGs) in rat, mouse, and human fetal testis. Phthalate exposures also result in a decrease in testicular testosterone in rats...

Barium alginate caged Fe3O4@C18 magnetic nanoparticles for the pre-concentration of polycyclic aromatic hydrocarbons and phthalate esters from environmental water samples.

PubMed

Zhang, Shengxiao; Niu, Hongyun; Cai, Yaqi; Shi, Yali

2010-04-30

The hydrophobic octadecyl (C(18)) functionalized Fe(3)O(4) magnetic nanoparticles (Fe(3)O(4)@C(18)) were caged into hydrophilic barium alginate (Ba(2+)-ALG) polymers to obtain a novel type of solid-phase extraction (SPE) sorbents, and the sorbents were applied to the pre-concentration of polycyclic aromatic hydrocarbons (PAHs) and phthalate esters (PAEs) pollutants from environmental water samples. The hydrophilicity of the Ba(2+)-ALG cage enhances the dispersibility of sorbents in water samples, and the superparamagnetism of the Fe(3)O(4) core facilitates magnetic separation. With the magnetic SPE technique based on the Fe(3)O(4)@C(18)@Ba(2+)-ALG sorbents, it requires only 30 min to extract trace levels of analytes from 500 mL water samples. After the eluate is condensed to 0.5 mL, concentration factors for both phenanthrene and di-n-propyl-phthalate are over 500, while for other analytes are about 1000. The recoveries of target compounds are independent of salinity and solution pH under testing conditions. Under optimized conditions, the detection limits for phenanthrene, pyrene, benzo[a]anthracene, and benzo[a]pyrene are 5, 5, 3, and 2 ng L(-1), and for di-n-propyl-phthalate, di-n-butyl-phthalate, di-cyclohexyl-phthalate, and di-n-octyl-phthalate are 36, 59, 19, and 36 ng L(-1), respectively. The spiked recoveries of several real water samples for PAHs and PAEs are in the range of 72-108% with relative standard deviations varying from 1% to 9%, showing good accuracy of the method. The advantages of the new SPE method include high extraction efficiency, short analysis time and convenient extraction procedure. To the best of our knowledge, it is unprecedented that hydrophilic Ba(2+)-ALG polymer caged Fe(3)O(4)@C(18) magnetic nanomaterial is used to extract organic pollutants from large volumes of water samples. Copyright 2010 Elsevier B.V. All rights reserved.

Simultaneous determination of 11 phthalate esters in bottled beverages by graphene oxide coated hollow fiber membrane extraction coupled with supercritical fluid chromatography.

PubMed

Lou, Chaoyan; Guo, Dandan; Zhang, Kai; Wu, Can; Zhang, Peimin; Zhu, Yan

2018-05-12

Phthalate esters (PAEs) are a group of serious environmental pollutants, which lead to carcinogenicity or tumorigenicity in human body. In this study, a rapid, sensitive and green method by graphene oxide coated hollow fiber membrane extraction (GO-HFME) coupled with supercritical fluid chromatography (SFC) was proposed for the determination of 11 phthalate esters in bottled beverages. Graphene oxide (GO) was prepared and coated onto a porous hollow fiber membrane (HFM) to reinforce the efficiency of membrane extraction. The modified hollow fiber membrane was employed for the extraction of phthalate esters from bottled beverages prior to the determination by the supercritical fluid chromatography with UV detection. To achieve the maximum extraction efficiency, several parameters were investigated including GO concentration, extraction time, desorption solution and desorption time. SFC variables including stationary phase, modifier composition and percentage, column temperature, flow rate and backpressure were studied to improve the separation conditions. Under these optimized conditions, all the studied 11 phthalate esters were well separated and simultaneously determined in 7 min by SFC. The performance of the developed method was evaluated. Good linearity was observed (R ≥ 0.999) in the range of 0.02-10.0 μg/mL with limit of detection (LOD, S/N = 3) ranging from 1.5 to 3.0 ng/mL. Recoveries of all the PAEs for the spiked samples were between 92.1% and 99.3% with satisfactory relative standard deviations (RSD) less than 5.9%. The proposed method is time-saving, green, simple and robust, which will be an alternative way to the analysis of PAEs in real samples. Copyright © 2018 Elsevier B.V. All rights reserved.

Study of solvent sublation for concentration of trace phthalate esters in plastic beverage packaging and analysis by gas chromatography-mass spectrometry.

PubMed

Chang, Lin; Bi, Pengyu; Li, Xiaochen; Wei, Yun

2015-06-15

A novel trace analytical method based on solvent sublation (SS) and gas chromatography-mass spectrometry (GC-MS) was developed for the trace determination of twenty-two phthalate esters (PAEs) from plastic beverage packaging. In the solvent sublation section, the effects of solution pH, NaCl concentration, nitrogen flow rate, and sublation time on the sublation efficiency were investigated in detail, and the optimal conditions were obtained. The trace PAEs migrated from plastic beverage packaging to food simulants were separated and concentrated by solvent sublation, and then the trace target compounds in the concentrated solution were analyzed by GC-MS. According to the European Union Regulation, the food simulants including distilled water for the normal beverages and acetic acid solution (3%) for the acetic beverage of yogurt were prepared for migration tests. The trace analysis method showed good linearity, low limits of detection (LODs) of 1.6-183.5 ng/L, and satisfied recoveries (67.3-113.7%). Copyright © 2015 Elsevier Ltd. All rights reserved.

The concentrations of phthalates in settled dust in Bulgarian homes in relation to building characteristic and cleaning habits in the family

NASA Astrophysics Data System (ADS)

Kolarik, Barbara; Bornehag, Carl-Gustaf; Naydenov, Kiril; Sundell, Jan; Stavova, Petra; Nielsen, Ole Faurskov

Phthalate esters are chemical compounds with a broad range of applications. Recently, we have shown that significantly higher dust concentration of di(2-ethylhexyl) phthalate (DEHP) was found in Bulgarian homes of children with asthma or allergies compared to healthy children. The concentration of DEHP was found to be significantly associated with wheezing in the last 12 months as reported by parents. The objective of the current study was to examine the associations between concentrations of phthalates in settled dust collected in Bulgarian homes and building characteristics and cleaning habits. Dust samples from the child's bedroom were collected in 177 homes and analysed for the content of dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DnBP), butyl benzyl phthalate (BBzP), di- n-octyl phthalate (DnOP) and DEHP. Information on building characteristics and family habits were collected from parental reports in questionnaires and from inspectors' observations in the homes. Significantly higher concentrations of BBzP, DEHP and DnOP in indoor dust were found in homes where polishing agents were used, compared to homes where such products were not used. The highest concentrations of DEHP, BBzP and DnOP were found in homes with the combination of a low frequency of dusting and the use of polish. There was no difference in phthalate concentrations between inspector-observed balatum flooring (PVC or linoleum) and wood flooring as well as between PVC, as determined by Raman spectra, and wood flooring. However, in a sub-group of homes with no use of polish, the concentration of DEHP was higher in homes with inspector-observed balatum compared with wood flooring but the difference was not significant may be due to a too small sample size.

Mechanism of action and cumulative effects of phthalate esters to alter male reproductive development in the rat.

EPA Science Inventory

Phthalate diesters are high-produciton volume chemicals used to impart flexibility to polyvinyl plastic (e.g. children's toys and medical tubing) as well as other products (e.g. health and beauty products). Humans are ubiquitously exposed to these chemicals. Certain phthalate est...

Determination of the Composition and Quantity of Phthalate Ester Additives in PVC Children's Toys. Greenpeace Research Laboratories Technical Note 06/97.

ERIC Educational Resources Information Center

Stringer, Ruth; Labounskaia, Irina; Santillo, David; Johnston, Paul; Siddorn, John; Stephenson, Angela

Polyvinyl chloride (vinyl or PVC) is widely used in toys and other children's products. This study, conducted by Greenpeace, examined the composition and quantity of phthalate ester additives in children's PVC toys, used to give the toys added flexibility. Drawn from 17 countries, a total of 71 toys designed to be chewed by babies and young…

Magnetic N-doped mesoporous carbon as an adsorbent for the magnetic solid-phase extraction of phthalate esters from soft drinks.

PubMed

Li, Menghua; Jiao, Caina; Yang, Xiumin; Wang, Chun; Wu, Qiuhua; Wang, Zhi

2017-04-01

A new kind of magnetic N-doped mesoporous carbon was prepared by the one-step carbonization of a hybrid precursor (glucose, melamine, and iron chloride) in a N 2 atmosphere with a eutectic salt (KCl/ZnCl 2 ) as the porogen. The obtained magnetic N-doped mesoporous carbon showed excellent characteristics, such as strong magnetic response, high surface area, large pore volume, and abundant π-electron system, which endow it with a great potential as a magnetic solid-phase extraction adsorbent. To evaluate its adsorption performance, the magnetic N-doped mesoporous carbon was used for the extraction of three phthalate esters from soft drink samples followed by high-performance liquid chromatographic analysis. Under the optimum conditions, the developed method showed a good linearity (1.0-120.0 ng/mL), low limit of detection (0.1-0.3 ng/mL, S/N = 3), and good recoveries (83.2-119.0%) in soft drink samples. The results indicated that the magnetic N-doped mesoporous carbon has an excellent adsorption capacity for phthalate esters and the present method is simple, accurate, and highly efficient for the extraction and determination of phthalate esters in complex matrix samples. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Synthesis of molecularly imprinted polymers by atom transfer radical polymerization for the solid-phase extraction of phthalate esters in edible oil.

PubMed

Chen, Ningning; He, Juan; Wu, Chaojun; Li, Yuanyuan; Suo, An; Wei, Hongliang; He, Lijun; Zhang, Shusheng

2017-03-01

Novel molecularly imprinted polymers of phthalate esters were prepared by atom transfer radical polymerization using methyl methacrylate as functional monomer, cyclohexanone as solvent, cuprous chloride as catalyst, 1-chlorine-1-ethyl benzene as initiator and 2,2-bipyridyl as cross-linker in the mixture of methanol and water (1:1, v/v). The effect of reaction conditions such as monomer ratio and template on the adsorption properties was investigated. The optimum condition was obtained by an orthogonal experiment. The obtained polymers were characterized using scanning electron microscopy. The binding property was studied with both static and dynamic methods. Results showed that the polymers exhibited excellent recognition capacity and outstanding selectivity for ten phthalate esters. Factors affecting the extraction efficiency of the molecularly imprinted solid-phase extraction were systematically investigated. An analytical method based on the molecularly imprinted coupled with gas chromatography and flame ionization detection was successfully developed for the simultaneous determination of ten phthalate esters from edible oil. The method detection limits were 0.10-0.25 μg/mL, and the recoveries of spiked samples were 82.5-101.4% with relative standard deviations of 1.24-5.37% (n = 6). © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Assessing human exposure to phthalic acid and phthalate esters from mineral water stored in polyethylene terephthalate and glass bottles.

PubMed

Montuori, P; Jover, E; Morgantini, M; Bayona, J M; Triassi, M

2008-04-01

Phthalic acid and phthalate esters are of growing interest due to their significant usage and potential toxicity. Polyethylene terephthalate (PET) and glass are both widely used materials for bottled drinking water. In this study, phthalic acid (PhA), bis(2-ethylhexyl) phthalate (DEHP), dimethyl phthalate (DMP), diethyl phthalate (DEP), diisobutyl phthalate (DiisoBP) and dibutyl phthalate (DBP) were analysed in a large number of Italian bottled water samples. These samples showed different concentrations of phthalates are nearly 20 times higher in samples bottled in PET than those from glass bottles with total levels of phthalates of 3.52 and 0.19 microg l(-1), respectively. However, the observed levels do not represent a significant exposure pathway when considering the US Environmental Protection Agency (USEPA) reference dose (an estimate of a daily oral exposure to the human population, including sensitive subgroups, that is likely to be without an appreciable risk of deleterious effects during a lifetime). In addition, no significant correlation was found between the phthalate concentrations and the physicochemical properties of the different water samples, apart from the still/sparkling water parameter for the PET samples. In this instance, slightly higher concentrations were observed for the PET bottled still water samples than for the sparkling water samples, although no explanation has been found yet.

Prenatal Exposure to Phthalate Esters and Behavioral Syndromes in Children at 8 Years of Age: Taiwan Maternal and Infant Cohort Study

PubMed Central

Lien, Yin-Ju; Ku, Hsiu-Ying; Su, Pen-Hua; Chen, Suh-Jen; Chen, Hsiao-Yen; Liao, Pao-Chi; Chen, Wei-J.

2014-01-01

Background: Few studies have shown an association between prenatal phthalate exposure and adverse effects on neurodevelopment and behavior in young children. Objectives: We aimed to assess the relationship between prenatal exposure to phthalate esters and behavior syndromes in children at 8 years of age. Methods: A total of 122 mother–child pairs from the general population in central Taiwan were studied from 2000 to 2009. Mono-methyl phthalate (MMP), mono-ethyl phthalate (MEP), mono-butyl phthalate (MBP), mono-benzyl phthalate (MBzP), and three di-(2-ethylhexyl) phthalate (DEHP) metabolites—mono-2-ethylhexyl, mono-2-ethyl-5-hydroxyhexyl, and mono-2-ethyl-5-oxohexyl phthalates (MEHP, MEHHP, and MEOHP)—were measured in maternal urine collected during the third trimester of pregnancy using liquid chromatography–electrospray ionization–tandem mass spectrometry. Behavioral syndromes of children at 8 years of age were evaluated using the Child Behavior Checklist (CBCL). Associations between log10-transformed creatinine-corrected phthalate concentrations and standardized scores of the CBCL were estimated using linear regression models or multinomial logistic regressions with adjustments for potential confounders. Results: Externalizing problem scores were significantly higher in association with a 1-unit increase in log10-transformed creatinine-corrected concentrations of maternal MBP (β = 4.29; 95% CI: 0.59, 7.99), MEOHP (β = 3.74; 95% CI: 1.33, 6.15), and MEHP (β = 4.28 ; 95% CI: 0.03, 8.26) after adjusting for the child’s sex, intelligence, and family income. Meanwhile, MBP and MEOHP were significantly associated with Delinquent Behavior and Aggressive Behavior scores. The same pattern was found for borderline and/or clinical ranges. Conclusions: Our findings suggest positive associations between maternal DEHP and dibutyl phthalate (DBP) exposure and externalizing domain behavior problems in 8-year-old children. Citation: Lien YJ, Ku HY, Su PH, Chen SJ, Chen HY, Liao PC, Chen WJ, Wang SL. 2015. Prenatal exposure to phthalate esters and behavioral syndromes in children at 8 years of age: Taiwan Maternal and Infant Cohort Study. Environ Health Perspect 123:95–100; http://dx.doi.org/10.1289/ehp.1307154 PMID:25280125

Effects of clay minerals on diethyl phthalate degradation in Fenton reactions.

PubMed

Chen, Ning; Fang, Guodong; Zhou, Dongmei; Gao, Juan

2016-12-01

Phthalate esters are a group of plasticizers, which are commonly detected in China's soils and surface water. Fenton reactions are naturally occurring and widely applied in the degradation of contaminants. However, limited research was considered the effects of clay minerals on contaminants degradation with OH oxidation. In this study, batch experiments were conducted to investigate the degradation of diethyl phthalate (DEP) in Fenton reactions in the presence of clay minerals, and the effects of clay type, Fe content in clay structure. The results showed the clay adsorption inhibited total degradation of DEP, and Fe content in clay structure played an important role in DEP degradation, including in solution and adsorbed in clay minerals. Clay minerals with less Fe content (<3%) quenched OH radical, while nontronite with Fe content 19.2% improved OH radical generation and accelerated DEP degradation in solution. The degradation of clay-adsorbed DEP was much slower than DEP in solution. Six main products of DEP degradation were identified, including monoethyl phthalate, phthalate acid, hydroxyl diethyl phthalate, etc. This study implied that phthalate ester's degradation would be much slower in natural water than expected in the presence of clay minerals. Copyright © 2016 Elsevier Ltd. All rights reserved.

CLONING AND CHARACTERIZATION OF THE PHTHALATE CATABOLISM REGION OF PRE1 OF ARTHROBACTER KEYSERI 12B

EPA Science Inventory

o-Phthalate (benzene-1,2-dicarboxylate) is a central intermediate in the bacterial degradation of phthalate ester plasticizers as well as of a number of fused-ring polycyclic aromatic hydrocarbons found in fossil fuels. In Arthrobacter keyseri 12B, the genes encoding catabolism o...

Occurrence of phthalic acid esters in source waters: a nationwide survey in China during the period of 2009-2012.

PubMed

Liu, Xiaowei; Shi, Jianghong; Bo, Ting; Zhang, Hui; Wu, Wei; Chen, Qingcai; Zhan, Xinmin

2014-01-01

The first nationwide survey of six phthalic acid esters (PAEs) (diethyl phthalate (DEP); dimethyl phthalate (DMP); di-n-butyl phthalate (DBP); butyl benzyl phthalate (BBP); bis(2-ethylhexyl) phthalate (DEHP); di-n-octyl phthalate (DnOP)) in source waters was conducted in China. The results showed these PAEs were ubiquitous in source waters. DBP and DEHP were the most frequently detected with high concentrations ranging nd-1.52 μg/L and nd-6.35 μg/L, respectively. These PAEs concentrations (except DBP) in surface water (rivers, lakes and reservoirs) were generally higher than those in groundwater; DBP had high concentrations in groundwater in Northeast China (Liao River Basin) and North China (Hai River Basin). Their concentrations in the northern regions were generally higher than those in the southern and eastern regions; particularly, in North China. Three short-chain PAEs (DMP, DEP and DBP) were detected with high concentrations in Hai River Basin, Pearl River Basin and Yellow River Basin. Copyright © 2013 Elsevier Ltd. All rights reserved.

Fetal and Childhood Exposure to Phthalate Diesters and Cognitive Function in Children Up to 12 Years of Age: Taiwanese Maternal and Infant Cohort Study

PubMed Central

Huang, Han-Bin; Chen, Hsin-Yi; Su, Pen-Hua; Huang, Po-Chin; Sun, Chien-Wen; Wang, Chien-Jen; Chen, Hsiao-Yen

2015-01-01

Few studies have examined the association between environmental phthalate exposure and children’s neurocognitive development. This longitudinal study examined cognitive function in relation to pre-and postnatal phthalate exposure in children 2–12 years old. We recruited 430 pregnant women in their third trimester in Taichung, Taiwan from 2001–2002. A total of 110, 79, 76, and 73 children were followed up at ages 2, 5, 8, and 11, respectively. We evaluated the children’s cognitive function at four different time points using the Bayley and Wechsler tests for assessing neurocognitive functions and intelligence (IQ). Urine samples were collected from mothers during pregnancy and from children at each follow-up visit. They were analyzed for seven metabolite concentrations of widely used phthalate esters. These esters included monomethyl phthalate, monoethyl phthalate, mono-butyl phthalate, mono-benzyl phthalate, and three metabolites of di(2-ethylhexyl) phthalate, namely, mono-2-ethylhexyl phthalate, mono(2-ethyl-5-hydroxyhexyl) phthalate, and mono(2-ethyl-5-oxohexyl) phthalate. We constructed a linear mixed model to examine the relationships between the phthalate metabolite concentrations and the Bayley and IQ scores. We found significant inverse associations between the children’s levels of urinary mono(2-ethyl-5-oxohexyl) phthalate and the sum of the three metabolites of di(2-ethylhexyl) phthalate and their IQ scores (β = -1.818; 95% CI: -3.061, -0.574, p = 0.004 for mono(2-ethyl-5-oxohexyl) phthalate; β = -1.575; 95% CI: -3.037, -0.113, p = 0.035 for the sum of the three metabolites) after controlling for maternal phthalate levels and potential confounders. We did not observe significant associations between maternal phthalate exposure and the children’s IQ scores. Children’s but not prenatal phthalate exposure was associated with decreased cognitive development in the young children. Large-scale prospective cohort studies are needed to confirm these findings in the future. PMID:26121592

Biodegradation of phthalate esters by newly isolated Rhizobium sp. LMB-1 and its biochemical pathway of di-n-butyl phthalate.

PubMed

Tang, W-J; Zhang, L-S; Fang, Y; Zhou, Y; Ye, B-C

2016-07-01

To isolate a novel strain that could degrade many kinds PAEs efficiently and investigate the DBP-degrading pathway in this strain. Based on its 16S rRNA gene sequence, the strain was identified as Rhizobium sp. This strain, named LMB-1, can also utilize phthalates, such as DEHP, DMP, DBP and DEP. During the degradation of DBP, six possible metabolites, diethyl phthalate, mono-ethyl phthalate, di-methyl phthalate, mono-methyl phthalate, phthalic acid and tartaric acid, were identified by gas chromatography-mass spectrometry (GC-MS) analysis, and the degradation pathway of DBP was also identified in this study. In summary, strain LMB-1, identified as Rhizobium sp., was found to be capable of efficiently degrading PAEs, and it was determined that the strain degraded DMP completely within 45 h. DEP, DMP, MEP, MMP, PA and tartaric acid were detected during the course of DBP degradation by LMB-1. We propose that this strain could completely degrade DBP or other PAEs. Our results offer a novel and potential candidate, Rhizobium sp. LMB-1, for use in the bioremediation of cultivated soil contaminated by PAEs. This is the first report concerning the complete degradation of phthalate esters by Rhizobium sp. © 2016 The Society for Applied Microbiology.

Screening of phthalate esters in 47 branded perfumes.

PubMed

Al-Saleh, Iman; Elkhatib, Rola

2016-01-01

In the last few years, the use of phthalates in perfumes has gained attention because these chemicals are sometimes added intentionally as a solvent and a fixative. Five phthalate esters, dimethyl phthalate (DMP), diethyl phthalate (DEP), dibutyl phthalate (DBP), benzyl butyl phthalate (BBP), and diethyl hexyl phthalate (DEHP), were measured in 47 branded perfumes using headspace solid phase microextraction (SPME) followed by gas chromatography-mass spectrometry (GC-MS). The results revealed considerable amounts of phthalate in all 47 brands with detection frequencies > limit of quantitation in the following order: DEP (47/47) > DMP (47/47) > BBP (47/47) > DEHP (46/47) > DBP (23/45). Of the 47 brands, 68.1, 72.3, 85.1, 36.2, and 6.7 % had DEP, DMP, BBP, DEHP, and DBP levels, respectively, above their reported threshold limits. Of these phthalates, DEP was found to have the highest mean value (1621.625 ppm) and a maximum of 23,649.247 ppm. The use of DEP in the perfume industry is not restricted because it does not pose any known health risks for humans. DMP had the second highest level detected in the perfumes, with a mean value of 30.202 ppm and a maximum of 405.235 ppm. Although DMP may have some uses in cosmetics, it is not as commonly used as DEP, and again, there are no restrictions on its use. The levels of BBP were also high, with a mean value of 8.446 ppm and a maximum of 186.770 ppm. Although the EU banned the use of BBP in cosmetics, 27 of the tested perfumes had BBP levels above the threshold limit of 0.1 ppm. The mean value of DEHP found in this study was 5.962 ppm, and a maximum was 147.536 ppm. In spite of its prohibition by the EU, 7/28 perfumes manufactured in European countries had DEHP levels above the threshold limit of 1 ppm. The DBP levels were generally low, with a mean value of 0.0305 ppm and a maximum value of 0.594 ppm. The EU banned the use of DBP in cosmetics; however, we found three brands that were above the threshold limit of 0.1 ppm, and all were manufactured in European countries. The results of this study are alarming and definitely need to be brought to the attention of the public and health regulators. Although some phthalate compounds are still used in cosmetics, many scientists and environmental activists have argued that phthalates are endocrine-disrupting chemicals that have not been yet proven to be safe for any use, including cosmetics. Phthalates may also have different degrees of estrogenic modes of action. Furthermore, we should not dismiss the widespread use of phthalates in everyday products and exposure to these chemicals from sources such as food, medications, and other personal care products.

Response to Request for Correction 10001

EPA Pesticide Factsheets

Reponse to the Phthalate Esters Panel of the American Chemistry Council, in which the EPA concludes that the underlying information and conclusions presented in the Phthalates Action Plan are objective and of high quality.

Phthalate esters (PAEs): emerging organic contaminants in agricultural soils in peri-urban areas around Guangzhou, China.

PubMed

Zeng, Feng; Cui, Kunyan; Xie, Zhiyong; Wu, Lina; Liu, Min; Sun, Guoquan; Lin, Yujun; Luo, Danling; Zeng, Zunxiang

2008-11-01

This study reports the first data on the concentrations and distribution of phthalate esters (PAEs) in the agricultural soils from the peri-urban areas of Guangzhou city. Sigma(16)PAEs concentrations ranged from 0.195 to 33.6 microg g(-1)-dry weight (dw). Elevated levels of PAEs were recorded in the vegetable fields located next to the urban districts, and a decreasing trend exists following the distance away from the urban center. Diisobutyl phthalate (DiBP), Di-n-butyl phthalate (DnBP), and Di(2-ethylhexyl) phthalate (DEHP) dominated the PAEs in the agricultural soils. Significant relationship (correlation coefficient R(2)=0.85, p<0.01, n=40) was present between the accumulation of PAEs and total organic carbons in agricultural soils. In addition, both pH and texture of soils are found to be important factors affecting the level of PAEs. This study shows that the agricultural soils in the peri-urban area of Guangzhou city were moderately polluted by PAEs.

Study of the repartition of phthalate esters during distillation of wine for spirit production.

PubMed

Montevecchi, Giuseppe; Masino, Francesca; Di Pascale, Nicolas; Vasile Simone, Giuseppe; Antonelli, Andrea

2017-12-15

Due to health concerns and legal matters, an investigation to limit phthalates esters (PEAs) in spirits is necessary. A lab still was used to perform pilot distillations according to the official method for brandy production in order to explore the repartition into the distilled fractions of each PAE. The process was divided in two steps: a première chauffe and a bonne chauffe. The former step included the cut into heads, heart and tails, while the latter into heads, brandy, secondes, and tails. The behaviour of each PAE during distillation was affected by its own chemical nature. Dibutyl phthalate (DBP) was entirely carried over into the distillate, while bis(2-ethylhexyl) phthalate (DEHP) only partially, and diisononyl phthalate (DINP) accumulated in the stillage. During the bonne chauffe, DBP and DEHP accumulated in the secondes more than in the brandy. A rectification step of the secondes was demonstrated to considerably reduce PAEs concentration. Copyright © 2017. Published by Elsevier Ltd.

Analysis of 16 phthalic acid esters in food simulants from plastic food contact materials by LC-ESI-MS/MS.

PubMed

Li, Xiaojing; Xiong, Wenming; Lin, Hua; Zhuo, Liyang; Lv, Shuiyuan; Tang, Xi; Chen, Minshi; Zou, Zhexiang; Lin, Zhenyu; Qiu, Bin; Chen, Guonan

2013-02-01

An RP LC-ESI-MS/MS method for the determination of the migration of 16 primary phthalic acid esters from plastic samples has been developed using distilled water, 3% acetic acid, 10% alcohol, and olive oil as food simulants. Detection limits were 1.6-18.5 μg/kg in distilled water, 1.4-17.3 μg/kg in 3% acetic acid, 1.4-19.2 μg/kg in 10% alcohol, and 31.9-390.8 μg/kg in olive oil. The RSDs were in the range of 0.07-11.28%. The real plastic products inspection showed that only few analyzed samples were phthalates contaminated. Bis-2-ethylhexyl ester and dibutyl phthalate were the common items migrated from the plastic products into food and feeds, but the migration concentrations were far below the limits set by European Union (1.5 mg/kg for bis-2-ethylhexyl ester and 0.3 mg/kg for dibutyl phthalate). © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Fate and transport modeling of phthalate esters from biosolid amended soil under corn cultivation.

PubMed

Sayyad, G; Price, G W; Sharifi, M; Khosravi, K

2017-02-05

Phthalate esters (PAEs) are prevalent in the environment due to the broad range of industrial, agriculture and domestic applications. The ubiquitous use of PAEs has resulted in their potential to reach groundwater sources through application of agri-chemicals and municipal biosolids. A study was conducted to monitor the fate and transport of seven commonly detected PAEs in the environment including: dimethyl phthalate (DMP), diethyl phthalate (DEP), benzyl butyl phthalate (BBP), bis(di-ethyl hexyl) phthalate (DEHP), di-n-octyl phthalate (DnOP), dipentyl phthalate (DPP), and di-n-butyl phthalate (DnBP). Biosolids sourced from the Halifax Regional Municipality were applied at three rates on field-based lysimeter cells which were cropped to corn (Zea mays) for one growing season. In the present study, breakthrough curves (BTCs) were established for phthalates leaching from a corn-cultivated agricultural soil profile. The HYDRUS-1D model and a two-site sorption model were applied to predict transport parameters of PAEs using an inverse solution approach. Results of our research revealed that higher PAE adsorption was observed based on increasing carbon chain number. In addition, higher values of F (i.e. the fraction of type-1 sorption sites assumed to be in equilibrium with the solution phase) and lower values of D (i.e. dispersion coefficient) were observed for PAEs with large carbon chains which was validated both through the empirical dataset and the model simulations. Copyright © 2016. Published by Elsevier B.V.

Assessment of phthalate-induced changes in fetal rat testis gene expression using an rt-PCR array

EPA Science Inventory

Lambright, CS’, Sampson, H2, Furr, i1, Evans, N’, Hannas, B’, Gray, LE, Jr.’, VS Wilson1. 1USEPA, NHEERL, RTP, NC, 2USEPA, NHEERL, RTP, NC, ORISE Fellow. Phthalate esters (PE) such as diethyl hexyl phthalate (DEHP) produce reproductive malformations in male rodents by reduction o...

HEPATOCYTE EXPRESION OF TUMOR ASSOCIATED ALDEHYDE DEHYDROGENASE (ALDH-3) AND P21 RAS FOLLOWING DIETHYLNITROSAMINE (DEN) INITIATION AND CHRONIC EXPOSURE TO DI(2-ETHYLHEXYL) PHTHALATE (DHEP)

EPA Science Inventory

Phthalate esters such as di(2-ethylhexyl)phthalate (DEHP)either promote or inhibit rat liver tumorigenesis depending on the carcinogenesis protocol. In this study, we examined the expression of two histochemical markers, the tumor associated isozyme of aldehyde dehydrogenase (ALD...

FETAL TESTOSTERONE LEVELS ARE DIFFERENTIALLY AFFECTED IN MALE SPRAGUE DAWLEY AND WISTAR RATS AFTER IN UTERO EXPOSURE TO DIETHYLHEXYL PHTHALATE: A DOSE RESPONSE STUDY.

EPA Science Inventory

Exposure to phthalate esters during sexual differentiation disrupts testosterone resulting in malformations of androgen-dependent tissues. We have found that gubernacular lesions are more prevalent in in utero diethylhexyl phthalate (DEHP)-treated Wistar male than in the SD rat o...

Determination of phthalate esters in soil using a quick, easy, cheap, effective, rugged, and safe method followed by GC-MS.

PubMed

Liu, Qianjun; Chen, Di; Wu, Jiyuan; Yin, Guangcai; Lin, Qintie; Zhang, Min; Hu, Huawen

2018-04-01

A quick, easy, cheap, effective, rugged, and safe procedure was designed to extract pesticide residues from fruits and vegetables with a high percentage of water. It has not been used extensively for the extraction of phthalate esters from sediments, soils, and sludges. In this work, this procedure was combined with gas chromatography with mass spectrometry to determine 16 selected phthalate esters in soil. The extraction efficiency of the samples was improved by ultrasonic extraction and dissolution of the soil samples in ultra-pure water, which promoted the dispersion of the samples. Furthermore, we have simplified the extraction step and reduced the risk of organic solvent contamination by minimizing the use of organic solvents. Different extraction solvents and clean-up adsorbents were compared to optimize the procedure. Dichloromethane/n-hexane (1:1, v/v) and n-hexane/acetone (1:1, v/v) were selected as the extractants from the six extraction solvents tested. C18/primary secondary amine (1:1, m/m) was selected as the sorbent from the five clean-up adsorbents tested. The recoveries from the spiked soils ranged from 70.00 to 117.90% with relative standard deviation values of 0.67-4.62%. The proposed approach was satisfactorily applied for the determination of phthalate esters in 12 contaminated soil samples. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Occurrences of organophosphorus esters and phthalates in the microplastics from the coastal beaches in north China.

PubMed

Zhang, Haibo; Zhou, Qian; Xie, Zhiyong; Zhou, Yang; Tu, Chen; Fu, Chuancheng; Mi, Wenying; Ebinghaus, Ralf; Christie, Peter; Luo, Yongming

2018-03-01

Chemical pollution in the microplastics has been concerned worldwide as pollutants might potentially transfer from the environment to living organisms via plastics. Here, we investigate organophosphorus esters (OPEs) and phthalic acid esters (PAEs) in the beached microplastics collected from 28 coastal beaches of the Bohai and Yellow Sea in north China. The analyzed microplastics included polyethylene (PE) pellets and fragments, polypropylene (PP) flakes and fragments and polystyrene (PS) foams. The tris-(2-chloroethyl)-phosphate (TCEP), tris (1-chloro-2-propyl) phosphate (TCPP) and di-(2-ethylhexyl) phthalate (DEHP) were the three predominant compounds found overall. The maximum Σ4 OPEs concentration was 84,595.9ngg -1 , almost three orders of magnitude higher than the maximum Σ9 PAEs concentration. The PP flakes and PS foams contained the highest concentrations of the additives in contrast to the PE pellets which contained the lowest. The high concentration level of carcinogenic chlorinated OPEs and DEHP with endocrine disrupting effects implied the suggested potential hazards to coastal organisms. Spatial differences and compositional variation of the additives among the different microplastics suggests different origins and residence times in the coastal environment. This indicates that the characteristics of chemical additives might be a useful approach when tracing sources of microplastics in the environment. Copyright © 2017 Elsevier B.V. All rights reserved.

Simultaneous determination of seven phthalic acid esters in beverages using ultrasound and vortex-assisted dispersive liquid-liquid microextraction followed by high-performance liquid chromatography.

PubMed

Yılmaz, Pelin Köseoğlu; Ertaş, Abdulselam; Kolak, Ufuk

2014-08-01

A sensitive, rapid, and simple high-performance liquid chromatography with UV detection method was developed for the simultaneous determination of seven phthalic acid esters (dimethyl phthalate, dipropyl phthalate, di-n-butyl phthalate, benzyl butyl phthalate, dicyclohexyl phthalate, di-(2-ethylhexyl) phthalate, and di-n-octyl phthalate) in several kinds of beverage samples. Ultrasound and vortex-assisted dispersive liquid-liquid microextraction method was used. The separation was performed using an Intersil ODS-3 column (C18 , 250 × 4.6 mm, 5.0 μm) and a gradient elution with a mobile phase consisting of MeOH/ACN (50:50) and 0.2 M KH2 PO4 buffer. Analytes were detected by a UV detector at 230 nm. The developed method was validated in terms of linearity, limit of detection, limit of quantification, repeatability, accuracy, and recovery. Calibration equations and correlation coefficients (> 0.99) were calculated by least squares method with weighting factor. The limit of detection and quantification were in the range of 0.019-0.208 and 0.072-0.483 μg/L. The repeatability and intermediate precision were determined in terms of relative standard deviation to be within 0.03-3.93 and 0.02-4.74%, respectively. The accuracy was found to be in the range of -14.55 to 15.57% in terms of relative error. Seventeen different beverage samples in plastic bottles were successfully analyzed, and ten of them were found to be contaminated by different phthalic acid esters. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

[Research on source profile of aerosol organic compounds in leather plant].

PubMed

Wang, Bo-Guang; Zhou, Yan; Feng, Zhi-Cheng; Liu, Hui-Xuan

2009-04-15

Through investigating current air pollution condition for PM10 in every factories of different style leather plants in Pearl River Delta, characteristic profile of semi-volatile organic compounds in PM10 emitted from leather factories and their contents were researched by using ultrasonic and gas chromatography and mass spectrum technology. The 6 types of organic compounds containing 46 species in total were found in the collected samples, including phenyl compounds, alcohols, PAHs, acids, esters and amides. The concentrations of PM10 in leather tanning plant, leather dying plant and man-made leather plant were 678.5, 454.5, 498.6 microgm x m(-3) respectively, and concentration of organic compounds in PM10 were 10.04, 6.89, 14.21 microg x m(-3) in sequence. The more important type of pollutants in each leather plants had higher contribution to total organic mass as follows, esters and amides in tanning plants profile account for 43.47% and 36.51% respectively; esters and alcohols in dying plants profiles account for 52.52% and 16.16% respectively; esters and amide in man-made leather plant have the highest content and account for 57.07% and 24.17% respectively. In the aerosol organic source profiles of tested leather plants, 9-octadecenamide was the abundant important species with the weight of 26.15% in tanning plant, and Bis(2-ethylhexyl) phthalate was up to 44.19% in the dying plant, and Bis(2-ethylhexyl) maleate and 1-hydroxy-piperidine had obviously higher weight in man-made plant than the other two plants.

Widespread occurrence of phthalic acid esters in raw oilseeds in China used for edible vegetable oil production.

PubMed

Hu, Ai-Peng; Liu, Yu-Lan; Shi, Long-Kai

2016-09-01

Seven different phthalic acid esters (PAEs) were quantified in 124 samples of 16 types of oilseeds from China using a simplified GC-MS method. Di-2-ethylhexyl phthalate and di-n-butyl phthalate were found in all tested oilseed samples. Each made a high contribution to the summed total PAEs. Total PAE concentrations in 124 oilseeds ranged from 0.14 to 3.05 mg kg(-1), and the mean was 0.99 mg kg(-1). Mandulapalka (Cyperus esculentus) samples were the most severely contaminated among all the tested specimens; maize germ samples were least contaminated. Di-n-octyl phthalate and butylbenzyl phthalate were not detected in 12 and five types of oilseeds, respectively. Only eight samples contained all seven analytes. No difference was observed between woody oil-bearing plant and herbaceous oil-bearing plant in terms of PAEs content.

Disruption of Retinol (Vitamin A) Signaling by Phthalate Esters: SAR and Mechanism Studies.

PubMed

Chen, Yanling; Reese, David H

2016-01-01

A spectrum of reproductive system anomalies (cryptorchidism, hypospadias, dysgenesis of Wolffian duct-derived tissues and prostate, and reduced sperm production) in male rats exposed in utero to phthalate esters (PEs) are thought to be caused by PE inhibition of fetal testosterone production. Recently, dibutyl and dipentyl phthalate (DBuP, DPnP) were shown to disrupt the retinol signaling pathway (RSP) in mouse pluripotent P19 embryonal carcinoma cells in vitro. The RSP regulates the synthesis and cellular levels of retinoic acid (RA), the active metabolite of retinol (vitamin A). In this new study, a total of 26 di- and mono-esters were screened to identify additional phthalate structures that disrupt the RSP and explore their mechanisms of action. The most potent PEs, those causing > 50% inhibition, contained aryl and cycloalkane groups or C4-C6 alkyl ester chains and were the same PEs reported to cause malformations in utero. They shared similar lipid solubility; logP values were between 4 and 6 and, except for PEs with butyl and phenyl groups, were stable for prolonged periods in culture. Mono- and cognate di-esters varied in ability to disrupt the RSP; e.g., DEHP was inactive but its monoester was active while DBuP was active yet its monoester was inactive. DBuP and dibenzyl phthalate both disrupted the synthesis of RA from retinol but not the ability of RA to activate gene transcription. Both PEs also disrupted the RSP in C3H10T1/2 multipotent mesenchymal stem cells. Based on this in vitro study showing that some PEs disrupt retinol signaling and previous in vivo studies that vitamin A/RA deficiency and PEs both cause strikingly similar anomalies in the male rat reproductive system, we propose that PE-mediated inhibition of testosterone and RA synthesis in utero are both causes of malformations in male rat offspring.

Profiles and risk assessment of phthalate acid esters (PAEs) in drinking water sources and treatment plants, East China.

PubMed

Kong, Yanli; Shen, Jimin; Chen, Zhonglin; Kang, Jing; Li, Taiping; Wu, Xiaofei; Kong, XiangZhen; Fan, Leitao

2017-10-01

This study is the first report describing the occurrence of 15 phthalate acid esters (PAEs) in the three typical water sources of YiXing City, Taihu Upper-River Basin, East China. The fate of target PAEs in the Jiubin drinking water treatment plant (JTP) was also analyzed. The amounts of Σ 15 PAE in the Hengshan (HS), Youche (YC), and Xijiu (XJ) water sources were relatively moderate, with mean values of 360, 357, and 697 ng L -1 , respectively. Bis(2-ethylhexyl) phthalate (DEHP) dominated the PAE concentration, making up 80% of the 15 total PAEs. The highest levels of Σ 15 PAE were found in HS, YC, and XJ in March 2015, January 2015, and July 2014, respectively. The occurrence and concentrations of these compounds were spatially dependent, and the mean concentrations of Σ 15 PAE in HS, YC, and XJ samples increased from the surface layer to the bottom layer with varied percentage increases. The removal efficiency of the PAEs in the finished water varied markedly, and the removal of PAEs by the JTP ranged from 12.8 to 64.5%. The potential ecosystem risk assessment indicated that the risk of PAEs was relatively low in these three water sources. However, risks posed by PAEs due to drinking water still exist; therefore, special attention should be paid to source control in the JTP, and advanced treatment processes for drinking water supplies should be implemented.

Transient receptor potential ankyrin 1 activation enhances hapten sensitization in a T-helper type 2-driven fluorescein isothiocyanate-induced contact hypersensitivity mouse model

DOE Office of Scientific and Technical Information (OSTI.GOV)

Shiba, Takahiro; Tamai, Takuma; Sahara, Yurina

2012-11-01

Some chemicals contribute to the development of allergies by increasing the immunogenicity of other allergens. We have demonstrated that several phthalate esters, including dibutyl phthalate (DBP), enhance skin sensitization to fluorescein isothiocyanate (FITC) in a mouse contact hypersensitivity model, in which the T-helper type 2 (Th2) response is essential. On the other hand, some phthalate esters were found to activate transient receptor potential ankyrin 1 (TRPA1) cation channels on sensory neurons. We then found a positive correlation between the enhancing effects of several types of phthalate esters on skin sensitization to FITC and their ability to activate TRPA1. Here wemore » examined the involvement of TRPA1 in sensitization to FITC by using TRPA1 agonists other than phthalate esters. During skin sensitization to FITC, the TRPA1 agonists (menthol, carvacrol, cinnamaldehyde and DBP) augmented the ear-swelling response as well as trafficking of FITC-presenting dendritic cells to draining lymph nodes. We confirmed that these TRPA1 agonists induced calcium influx into TRPA1-expressing Chinese hamster ovary (CHO) cells. We also found that TRPA1 antagonist HC-030031 inhibited DBP-induced calcium influx into TRPA1-expressing CHO cells. After pretreatment with this antagonist upon skin sensitization to FITC, the enhancing effect of DBP on sensitization was suppressed. These results suggest that TRPA1 activation will become a useful marker to find chemicals that facilitate sensitization in combination with other immunogenic haptens. -- Highlights: ► Role of TRPA1 activation was revealed in a mouse model of skin sensitization to FITC. ► TRPA1 agonists enhanced skin sensitization as well as dendritic cell trafficking. ► Dibutyl phthalate (DBP) has been shown to enhance skin sensitization to FITC. ► TRPA1 activation by DBP was inhibited by a selective antagonist, HC-030031. ► HC-030031 inhibited the enhancing effect of DBP on skin sensitization to FITC.« less

Correlation of phthalate exposures with semen quality

DOE Office of Scientific and Technical Information (OSTI.GOV)

Pant, Niraj; Shukla, Manju; Kumar Patel, Devendra

2008-08-15

Phthalates are widely used man-made chemical released in the environment and human exposure is mainly through diet. As the phthalate plasticizers are not covalently bound to PVC, they can leach, migrate or evaporate into the environment and as a result have become ubiquitously contaminants. The present study investigates the correlation, if any, between the phthalate esters (DEP, DEHP, DBP, DMP, DOP) and sperm mitochondrial status, ROS, LPO, SCSA, and sperm quality. The study was conducted in the urban/rural population of Lucknow visiting Obstetrics and Gynecology Department, CSMMU, Lucknow. Semen analysis was performed according to the WHO guidelines while phthalate analysismore » by HPLC and LPO by spectrophotometer and the sperm mitochondrial status, ROS, SCSA using flow cytometry. The questionnaire data showed no significant difference in the demographic characteristics among the groups. In general, urban population was found to have statistically significant higher levels of phthalate esters than the rural. Further, infertile men showed statistically significant (p < 0.05) higher levels of pollutants in the semen than fertile men. A negative correlation between semen phthalate level viz DEHP and sperm quality and positive association with depolarized mitochondria, elevation in ROS production and LPO, DNA fragmentation was established. The findings are suggestive that phthalates might be one among the contributing factors associated with the deterioration in semen quality and these adverse effects might be ROS, LPO and mitochondrial dysfunction mediated.« less

A Short-term In vivo Screen using Fetal Testosterone Production, a Key Event in the Phthalate Adverse Outcome Pathway, to Predict Disruption of Sexual Differentiation.

EPA Science Inventory

This study was designed to develop and validate a short-term in vivo protocol termed the Fetal Phthalate Screen (FPS) to detect phthalate esters (PEs) and other chemicals that disrupt fetal testosterone synthesis and testis gene expression in rats. We propose that the FPS can be ...

Analysis of Chemical Signatures of Alkaliphiles using Fatty Acid Methyl Ester Analysis

PubMed Central

Sreenivasulu, Basha; Paramageetham, Chinthala; Sreenivasulu, Dasari; Suman, Bukke; Umamahesh, Katike; Babu, Gundala Prasada

2017-01-01

Background: Fatty acids occur in nearly all living organisms as the important predominant constituents of lipids. While all fatty acids have essentially the same chemical nature, they are an extremely diverse group of compounds. Materials and Methods: To test the hypothesis, fatty acids of alkaliphiles isolates, Bacillus subtilis SVUNM4, Bacillus licheniformis SVUNM8, Bacillus methylotrohicus SVUNM9, and Paenibacillus dendritiformis SVUNM11, were characterized compared using gas chromatography-mass spectrometry (GC-MS) analysis. Results: The content of investigated ten fatty acids, 1, 2-benzenedicarboxylic acid butyl 2-methylpropyl ester, phthalic acid, isobutyl 2-pentyl ester, dibutyl phthalate, cyclotrisiloxane, hexamethyl, cyclotetrasiloxane, octamethyl, dodecamethyl, heptasiloxane 1,1,3,3,5,5,7,7,9,9,11,11,13,13-etradecamethyl, 7,15-dihydroxydehydroabietic acid, methyl ester, di (trimethylsilyl) ether, hentriacontane, 2-thiopheneacetic acid, undec-2-enyl ester, obviously varied among four species, suggesting each species has its own fatty acid pattern. Conclusions: These findings demonstrated that GC-MS-based fatty acid profiling analysis provides the reliable platform to classify these four species, which is helpful for ensuring their biotechnological interest and novel chemotaxonomic. PMID:28717333

Determination of phthalate esters in cleaning and personal care products by dispersive liquid-liquid microextraction and liquid chromatography-tandem mass spectrometry.

PubMed

Viñas, Pilar; Campillo, Natalia; Pastor-Belda, Marta; Oller, Ainhoa; Hernández-Córdoba, Manuel

2015-01-09

Phthalic acid esters (PEs) were preconcentrated from cleaning products, detergents and cosmetics using ultrasound assisted extraction (UAE) in the presence of acetonitrile, and then submitted to dispersive liquid-liquid microextraction (DLLME). For DLLME, 3mL of acetonitrile extract, 150μL carbon tetrachloride and 10mL aqueous solution were used. The enriched organic phase was evaporated, reconstituted with 25μL acetonitrile and injected into a liquid chromatograph with a mobile phase (acetonitrile:10mM ammonium acetate, pH 4) under gradient elution. Detection was carried out using both diode-array (DAD) and electrospray-ion trap-tandem mass spectrometry (ESI-IT-MS/MS) in the multiple reaction monitoring mode (MRM) of the positive fragment ions. Quantification was carried out using matrix-matched standards. Detection limits were in the range 0.04-0.45ngmL(-1) for the six PEs considered. The recoveries obtained were in the 84-124% range, with RSDs lower than 10%. Thirty three different cleaning products were analyzed. The most frequently found compound was diethyl phthalate. Copyright © 2014 Elsevier B.V. All rights reserved.

[Survey of plasticizers in polyvinyl chloride toys].

PubMed

Abe, Yutaka; Yamaguchi, Miku; Mutsuga, Motoh; Hirahara, Yoshichika; Kawamura, Yoko

2012-01-01

Plasticizers in 101 samples of polyvinyl chloride (PVC) toys on the Japanese market were surveyed. No phthalates were detected in designated toys, though bis(2-ethylhexyl)phthalate, diisononyl phthalate, diisobutyl phthalate, dibutyl phthalate, diisodecyl phthalate and benzyl butyl phthalate were detected in more than half of other toys. 2,2,4-Tributyl-1,3-pentanediol diisobutylate, o-acetyl tributyl citrate, adipates and diacetyl lauroyl glycerol, which are alternative plasticizers to phthalates, were detected. The results of structural analysis confirmed the presence of di(2-ethylhexyl)terephthalate, tributyl citrate, diisononyl 1,2-cyclohexanedicarboxylate and neopentyl glycol esters; these have not previonsly been reported in Japan. There appears to be a shift in plasticizers used for designated toys from phthalates to new plasticizers, and the number of different plasticizers is increasing.

Phthalate Esters in Indoor Window Films in a Northeastern Chinese Urban Center: Film Growth and Implications for Human Exposure.

PubMed

Huo, Chun-Yan; Liu, Li-Yan; Zhang, Zi-Feng; Ma, Wan-Li; Song, Wei-Wei; Li, Hai-Ling; Li, Wen-Long; Kannan, Kurunthachalam; Wu, Yong-Kai; Han, Ya-Meng; Peng, Zhi-Xiang; Li, Yi-Fan

2016-07-19

Indoor window film samples were collected in buildings during 2014-2015 for the determination of six phthalate diesters (PAEs). Linear regression analysis suggested that the film mass was positively and significantly correlated with the duration of film growth (from 7 to 77 days). PAEs were detected in all window film samples (n = 64). For all the samples with growth days ranged from 7 to 77 days, the median concentrations of total six PAEs (∑6PAEs) in winter and summer window film samples were 9900 ng/m(2) film (2000 μg/g film) and 4700 ng/m(2) film (650 μg/g film), respectively. Among PAEs analyzed, di-2-ethyl-hexyl phthalate (DEHP) was the major compound (71 ± 9.7%), followed by di-n-butyl phthalate (DBP; 20 ± 7.4%) and diisobutyl phthalate (DiBP; 5.1 ± 2.2%). Positive correlations among PAEs suggested their common sources in the window film samples. Room temperature and relative humidity were negatively and significantly correlated with PAEs concentations (in ng/m(2)). Poor ventilation in cold winter in Noreastern China significantly influenced the concentrations of PAEs in window film which suggested higher inhalation exposure dose in winter. The median hazard quotient (HQ) values from PAEs exposure were below 1, suggesting that the intake of PAEs via three exposure pathways was considered as acceptable.

Ortho-phthalic acid esters in lipophilic extract from the cell culture of Aconitum baicalense Turcz ex Rapaics 1907.

PubMed

Semenov, A A; Enikeev, A G; Snetkova, L V; Permyakov, A V; Sokolova, N A; Dudareva, L V

2016-11-01

Optically active bis-2R(-)ethylhexyl o-phthalate was obtained with 0.18% yield from dry cultured cells of Aconitum baicalense Turcz ex Rapaics 1907 by extraction with petroleum ether followed by silica gel column chromatography. Its structure was confirmed by the analysis of 13 C and 1 H NMR spectra. Seasonal fluctuations of quantitative phthalate content in A. baicalense cells were identified. The tests were performed under conditions excluding the presence of phthalates in reagents, materials, and laboratory dishes. The same substance was shown to be produced by cultivated cells of other plants. Biosynthesis of esters of ortho-phthalic acid by cultivated plant cells was discovered for the first time.

Development of an Analytical Method for Dibutyl Phthalate Determination Using Surrogate Analyte Approach

PubMed Central

Farzanehfar, Vahid; Faizi, Mehrdad; Naderi, Nima; Kobarfard, Farzad

2017-01-01

Dibutyl phthalate (DBP) is a phthalic acid ester and is widely used in polymeric products to make them more flexible. DBP is found in almost every plastic material and is believed to be persistent in the environment. Various analytical methods have been used to measure DBP in different matrices. Considering the ubiquitous nature of DBP, the most important challenge in DBP analyses is the contamination of even analytical grade organic solvents with this compound and lack of availability of a true blank matrix to construct the calibration line. Standard addition method or using artificial matrices reduce the precision and accuracy of the results. In this study a surrogate analyte approach that is based on using deuterium labeled analyte (DBP-d4) to construct the calibration line was applied to determine DBP in hexane samples. PMID:28496469

Determination of phthalic acid esters in water samples using core-shell poly(dopamine) magnetic nanoparticles and gas chromatography tandem mass spectrometry.

PubMed

González-Sálamo, Javier; Socas-Rodríguez, Bárbara; Hernández-Borges, Javier; Rodríguez-Delgado, Miguel Ángel

2017-12-29

In this work, the first application of core-shell poly(dopamine) magnetic nanoparticles as sorbent for the extraction of a group of eleven phthalic acid esters of interest (i.e. diethyl phthalate (DEP), dipropyl phthalate (DPP), dibutyl phthalate (DBP), bis-isopentyl phthalate (DIPP), bis-n-pentyl phthalate (DNPP), benzylbutyl phthalate (BBP), dicyclohexyl phthalate (DCHP), di-(2-ethylhexyl) phthalate (DEHP), di-n-octyl phthalate (DNOP), diisononyl phthalate (DINP) and diisodecyl phthalate (DIDP)) and one adipate (bis (2-ethylhexyl) adipate, DEHA) from different water samples (Milli-Q, mineral, tap, pond and waste water) is proposed. Analysis were carried out by gas chromatography triple quadrupole tandem mass spectrometry. Parameters that affect the extraction performance were optimized following a step by step approach, being the optimum conditions the extraction of water at pH 6, with 60mg of sorbent and the elution with 6mL of dichloromethane. The methodology was validated for the five selected water samples using DBP-d 4 as internal standard. Determination coefficients of matrix-matched calibration curves were above 0.9904 in all cases while relative recovery values ranged between 71 and 120%, with relative standard deviation values below 19%. The limits of quantification of the method ranged between 9 and 20ng/L. Matrix effects were found for most analytes and water samples. Real water samples were also analyzed, finding DEP and DBP at concentrations below 4.20 and 1.23μg/L, respectively, in mineral, tap and waste water. DCHP, DEHP and BBP were also found in some of the samples at concentrations below the LOQs of the method. Copyright © 2017 Elsevier B.V. All rights reserved.

PHTHALATE-INDUCED LEYDIG CELL HYPERPLASIA IS ASSOCIATED WITH MULTIPLE ENDOCRINE DISTURBANCES

EPA Science Inventory

The possibility that exposures to environmental agents are associated with reproductive disorders in human populations has generated much public interest recently. Phthalate esters are used most commonly as plasticizers in the food and construction industry, and DEHP is the most ...

Indoor phthalate concentration and exposure in residential and office buildings in Xi'an, China

NASA Astrophysics Data System (ADS)

Wang, Xinke; Tao, Wei; Xu, Ying; Feng, Jiangtao; Wang, Fenghao

2014-04-01

Indoor phthalate levels were investigated in 28 buildings, including 14 office and 14 residential buildings in Xi'an, China. Phthalate esters in the gas-, particle-, and dust- phase were measured separately. Four phthalates including dimethyl phthalate (DMP), diisobutyl phthalate (DiBP), di-n-butyl phthalate (DnBP) and di(2-ethylhexyl) phthalate (DEHP) were detected. The detection frequency of DnBP and DEHP was more than 90%. The concentrations of total phthalate esters ranged from 0.20 to 8.29 μg m-3 for the gas- phase, from 0.09 to 14.77 μg m-3 for the particle- phase and from 123 to 9504 μg g-1 for the dust- phase. The individual phthalate with the highest concentrations of 6.17 μg m-3, 7.97 μg m-3 and 7228 μg g-1 respectively for gas-, particle- and dust- phase in all investigated rooms is all DiBP. The median concentration of the gas- and particle-phase DiBP (0.52 and 0.72 μg m-3) and dust-phase DEHP (582 μg g-1) were the highest. It was also found that the average concentrations of individual phthalates in residential buildings were often higher than in office buildings, and correlation analysis indicated that DiBP, DnBP and DEHP might come from the same sources. Based on the gas- and particle-phase concentrations measured, the particle-air partition coefficients of phthalates were estimated, and their logarithm values were found to be linearly correlated with the logarithm values of their octanol-air partition coefficients. Finally, the total daily exposure to indoor phthalates in air and dust was calculated, and ranged from 2.6 μg kg-1 day-1 (for adults) to 7.4 μg kg-1 day-1 (for toddlers).

[Application of Stir Bar Sorptive Extraction and Gas Chromatograph Mass Spectrometer to the Phthalic Acid Esters Analysis in Seawater].

PubMed

Gao, Chen-chen; Li, Feng-min; Lu, Lun; Sun, Yue

2015-10-01

For the determination of trace amounts of phthalic acid esters (PAEs) in complex seawater matrix, a stir bar sorptive extraction gas chromatography mass spectrometry (SBSE-GC-MS) method was established. Dimethyl phthalate (DMP), diethyl phthalate (DEP), dibutyl phthalate (DBP), butyl benzyl phthalate (BBP), dibutyl phthalate (2-ethylhexyl) phthalate (DEHP) and dioctyl phthalate (DOP) were selected as study objects. The effects of extraction time, amount of methanol, amount of sodium chloride, desorption time and desorption solvent were optimized. The method of SBSE-GC-MS was validated through recoveries and relative standard deviation. The optimal extraction time was 2 h. The optimal methanol content was 10%. The optimal sodium chloride content was 5% . The optimal desorption time was 50 min. The optimal desorption solvent was the mixture of methanol to acetonitrile (4:1, volume: volume). The linear relationship between the peak area and the concentration of PAEs was relevant. The correlation coefficients were greater than 0.997. The detection limits were between 0.25 and 174.42 ng x L(-1). The recoveries of different concentrations were between 56.97% and 124.22% . The relative standard deviations were between 0.41% and 14.39%. On the basis of the method, several estuaries water sample of Jiaozhou Bay were detected. DEP was detected in all samples, and the concentration of BBP, DEHP and DOP were much higher than the rest.

Concentrations of phthalates and DINCH metabolites in pooled urine from Queensland, Australia.

PubMed

Gomez Ramos, M J; Heffernan, A L; Toms, L M L; Calafat, A M; Ye, X; Hobson, P; Broomhall, S; Mueller, J F

2016-03-01

Dialkyl phthalate esters (phthalates) are ubiquitous chemicals used extensively as plasticizers, solvents and adhesives in a range of industrial and consumer products. 1,2-Cyclohexane dicarboxylic acid, diisononyl ester (DINCH) is a phthalate alternative introduced due to a more favourable toxicological profile, but exposure is largely uncharacterised. The aim of this study was to provide the first assessment of exposure to phthalates and DINCH in the general Australian population. De-identified urine specimens stratified by age and sex were obtained from a community-based pathology laboratory and pooled (n=24 pools of 100). Concentrations of free and total species were measured using online solid phase extraction isotope dilution high performance liquid chromatography tandem mass spectrometry. Concentrations ranged from 2.4 to 71.9ng/mL for metabolites of di(2-ethylhexyl)phthalate, and from <0.5 to 775ng/mL for all other metabolites. Our data suggest that phthalate metabolites concentrations in Australia were at least two times higher than in the United States and Germany; and may be related to legislative differences among countries. DINCH metabolite concentrations were comparatively low and consistent with the limited data available. Ongoing biomonitoring among the general Australian population may help assess temporal trends in exposure and assess the effectiveness of actions aimed at reducing exposures. Copyright © 2015 Elsevier Ltd. All rights reserved.

Distribution of phthalate esters in agricultural soil with plastic film mulching in Shandong Peninsula, East China.

PubMed

Li, Kankan; Ma, Dong; Wu, Juan; Chai, Chao; Shi, Yanxi

2016-12-01

The content of phthalate esters (PAEs) was investigated in 36 vegetable fields with plastic film mulching in Shandong Peninsula, East China. Soils at depths of 0-10 cm, 10-20 cm, and 20-40 cm were collected, and 16 PAEs were analyzed by gas chromatography-mass spectrometry. PAEs were detected in all the analyzed samples. The total contents of the 16 PAEs (Σ 16 PAEs) ranged from 1.374 to 18.810 mg/kg, with an average of 6.470 mg/kg. Among the four areas of Shandong Peninsula, including Qingdao, Weihai, Weifang, and Yantai, the highest Σ 16 PAE in the soil was observed in Weifang district (9.786 mg/kg), which is famous for large-scale vegetable production. Despite the significant differences among the Σ 16 PAEs, the PAE compositions in soils with plastic film mulching in Shandong Peninsula were comparable. Diethyl phthalate (DEP), diisobutyl phthalate, and di(4-methyl-2-pentyl) phthalate were present in all the samples, whereas di-n-hexyl phthalate was detected only in Qingdao (∼1%) and dicyclohexyl phthalate was observed only in Weifang (5.7-8.2%) in low proportions. The ratios of dimethyl phthalate, DEP, and di-n-butyl phthalate, which exceeded allowable concentrations, were 63.9-100% at different soil depths, indicating high PAE pollution. The concentration of butyl benzyl phthalate detected only in Weifang exceeded the recommended allowable soil concentration. Overall, the high PAE content in the soil with plastic film mulching in Shandong Peninsula is an issue of concern because of the large amounts of plastic film used. Copyright © 2016 Elsevier Ltd. All rights reserved.

Levels of phthalate esters in settled house dust from urban dwellings with young children in Nanjing, China

NASA Astrophysics Data System (ADS)

Zhang, Qi; Lu, Xiao-Mei; Zhang, Xiao-Ling; Sun, Yong-Gang; Zhu, Dong-Mei; Wang, Bing-Ling; Zhao, Ren-Zheng; Zhang, Zheng-Dong

2013-04-01

To investigate the levels and possible determinants of phthalate esters (PEs) in settled house dust from urban dwellings with young children, dust was collected from 215 urban houses in Nanjing, China, and 145 outdoor settled dust samples were collected nearby. Six PEs were measured by gas chromatography/mass spectrometry. All PEs were detected in the dust from approximately 90% of the houses, with the exception of dioctyl phthalate (DOP), which had only a 59% detection rate. Di-2-ethylhexyl phthalate (DEHP) and di-n-butyl phthalate (DBP) were the most abundant PEs, with geometric means of 110 and 16.4 μg g-1, respectively, and maximal concentrations 9950 and 2150 μg g-1. Factor analysis showed that DBP, DEHP and benzyl butyl phthalate (BBP) might come from the same source and were significantly influenced by the use of solid-wood floor wax. High BBP, DEHP, DOP and total PE levels were associated with indices of dampness, and high DOP was associated with humidifier use. In conclusion, six PEs are ubiquitous in urban settled house dust in Nanjing, China, and both plastic materials and cosmetic and personal care products are important sources. Flooring material, dampness and humidifier use potentially influence house dust PE levels.

Di-isoheptyl Phthalate (DIHP) in utero exposure reduces testicular testosterone (T) production in fetal Sprague Dawley (SD) rats

EPA Science Inventory

Exposure to DIHP, a commercial phthalate ester plasticizer used in flooring manufacturing, during the fetal period of sexual differentiation disrupts male reproductive development resulting in reproductive malformations and reduced androgen-dependent reproductive tissue weights i...

The effects of simvastatin and dipentyl phthalate on fetal cholesterol and testosterone production

EPA Science Inventory

Sex differentiation of the male reproductive tract in mammals is driven, in part, by fetal androgen production. In utero, some phthalate esters (PEs) alter fetal Leydig cell differentiation, reducing the expression of genes associated with steroid synthesis/transport, and conseq...

[Analysis of phthalates in aromatic and deodorant aerosol products and evaluation of exposure risk].

PubMed

Sato, Yoshiki; Sugaya, Naeko; Nakagawa, Tomoo; Morita, Masatoshi

2015-01-01

We established an analytical method for the detection of seven phthalates, dimethyl phthalate, diethyl phthalate (DEP), benzyl butyl phthalate, di-i-butyl phthalate, dibutyl phthalate (DBP), diethylhexyl phthalate (DEHP), and di-n-octhyl phthalate, using an ultra high performance liquid chromatograph equipped with a photodiode array detector. This method is quick, with minimal contamination, and was applied to the analysis of aromatic and deodorant aerosol products. Phthalates were detected in 15 of 52 samples purchased from 1999 to 2012 in Yokohama. Three types of phthalate (DEP, DBP, DEHP) were detected, and their concentrations ranged from 0.0085-0.23% DEP in nine samples, 0.012-0.045% DBP in four samples, and 0.012-0.033% DEHP in four samples. No other phthalate esters were detected. Furthermore, we estimated phthalate exposure via breathing in commonly used aromatic and deodorant aerosol products, then evaluated the associated risk. The estimated levels of phthalate exposure were lower than the tolerated daily limit, but the results indicated that aromatic and deodorant aerosol products could be a significant source of phthalate exposure.

The role of phthalate esters in autism development: A systematic review.

PubMed

Jeddi, Maryam Zare; Janani, Leila; Memari, Amir Hossein; Akhondzadeh, Shahin; Yunesian, Masud

2016-11-01

Available evidence implicates environmental factors in the pathogenesis of autism spectrum disorders (ASD). However, the role of specific environmental chemicals such as phthalate esters that influence ASD risk remains elusive. This paper systematically reviews published evidences on association between prenatal and/or childhood exposure to phthalate and ASD. Studies pertaining to systematic literature search from Scopus, PubMed, PsycInfo and Web of Science prior to December 2015 were identified. The authors included studies which assessed the effect of exposure to phthalates on occurrence of ASD. This comprehensive bibliographic search identified five independent studies. Each eligible paper was summarized with respect to its methods and results with particular attention to study design and exposure assessment. Because of the heterogeneity in the type of included studies, different methods of assessing exposure to phthalates and the use of different statistics for summarizing the results, meta-analysis could not be used to combine the results of included studies. The results of this systematic review have revealed the limited number of studies conducted and assessed phthalate exposure. Seven studies were regarded as relevant to the objectives of this review. Two of them did not measure phthalate exposure directly and did not result in quantitative results. Out of the five studies in which phthalate exposure was mainly measured by the examining biomarkers in biological samples, two were cohort studies (one with positive results and another one with not clear association). Among the three case control studies, two of them showed a significant relation between exposure to phthalate and ASD and the last case control study had negative results. Indeed, this case control studies showed a compromised phthalate metabolite glucuronidation pathway, as a probable explanation of mechanism of the relation between phthalate exposure and ASD. This review reveals evidence showing a connection between exposure to phthalates and ASD. Nevertheless, further research is needed with appropriate attention to exposure assessment and relevant pre and post-natal cofounders. Copyright © 2016 Elsevier Inc. All rights reserved.

Investigation of the mechanism for phthalate-induced toxicity during male sexual differentiation in the rat

EPA Science Inventory

Male rats exposed to phthalate esters during sexual differentiation (GDI4-GDI8) display various developmental abnormalities of the reproductive tract that are manifested later in adult life. Induction of these malformations is associated with declines in fetal testicular testoste...

Di(n)butyl phthalate reduces testicular weight, testosterone and associated gene expression in fetal Harlan Sprague Dawley rats.

EPA Science Inventory

Certain phthalate esters (PE) cause reproductive malformations in male rats when exposure occurs during sexual differentiation in utero. Reductions in fetal testosterone levels are causally linked to the induction of these malformations. While reproductive development studies on ...

Investigation of the mechanism for phthalate-induced toxicity during male sexual differentiation in the rat.

EPA Science Inventory

Male rats exposed to phthalate esters during sexual differentiation (GDI4-GDI8) display various reproductive developmental abnormalities later in adult life which are associated with declines in fetal testicular testosterone (T) production and insulin-like three hormone (lnsl-3...

In utero phthalate effects in the female rat: a model for MRKH syndrome##

EPA Science Inventory

Mayer-Rokitansky-Kuster-Hauser (MRKH) syndrome is characterized by uterine and vaginal canal aplasia in normal karyotype human females and is a syndrome with poorly defined etiology. Reproductive toxicity of phthalate esters (PEs) occurs in rat offspring exposed in utero, a phen...

ONTOGENY OF CHANGES IN FETAL TESTIS GENE EXPRESSION INDUCED IN MALE OFFSPRING AFTER MATERNAL TREATMENT WITH DEHP (DIETHYLHEXYL PHTHALATE)

EPA Science Inventory

Phthalate esters are high production volume, ubiquitous environmental chemicals some of which induce reproductive malformations in rats when administered during sexual differentiation. Recently we have shown that malformations in gubernacular ligament development induced by DEHP...

Study on the Mechanism of Interaction between Phthalate Acid Esters and Bovine Hemoglobin.

PubMed

Chi, Zhenxing; Zhao, Jing; You, Hong; Wang, Mingjing

2016-08-03

Phthalate acid esters (PAEs) are widely used in plastic products as a series of chemical softeners. However, PAEs, which now exist in many environmental media such as the atmosphere, water, and soil, have been shown to be environmental endocrine disruptors. Hemoglobin is a functional protein that carries oxygen in the red blood cells of animals. This study aims at revealing the interactions between bovine hemoglobin (BHb) and PAEs using spectroscopic and molecular modeling methods. The results indicate that the selected representative PAEs-dimethyl phthalate (DMP), diethyl phthalate (DEP), and dibutyl phthalate (DBP)-can interact with BHb to form BHb-PAE complexes with one binding site, mainly relying on hydrophobic forces, with the affinity order DMP > DEP > DBP, opposite to the order of side-chain length. The binding of PAEs can cause conformational and micro-environmental changes in BHb, which may affect the physiological functions of Hb. Furthermore, molecular docking was applied to define the specific binding sites, the results of which show that all the three PAEs can bind into the central cavity of BHb. The study contributes to expound the toxic mechanism of PAEs in vivo from the point of hematological toxicology.

Solid-phase microextraction of phthalate esters by a new coating based on a thermally stable polypyrrole/graphene oxide composite.

PubMed

Jafari, Mostafa; Ebrahimzadeh, Homeira; Banitaba, Mohammad Hossein; Davarani, Saied Saeed Hosseiny

2014-11-01

A novel polypyrole/graphene oxide coating was made by the electrochemical polymerization of pyrrole in the presence of sodium dodecyl sulfate and graphene oxide on a platinum wire. The prepared fiber has shown a good thermal stability up to 300°C. The fiber was applied to the direct solid-phase microextraction and gas chromatographic analysis of four phthalate esters. The effect of four parameters on gas chromatography peak area including extraction temperature, extraction time, injection temperature, and ionic strength were investigated. Under the optimized conditions, the detection limits were between 0.042 and 0.26 μg/L. The intraday and interday relative standard deviations obtained at 55 μg/L, using a single fiber, were 8.2-16% and 17.3-25.6%, respectively. The method was successfully applied to the analysis of phthalate esters in two real samples of boiling water in cheap disposable clear plastic drinking cups showing recoveries from 83 to 120%. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Determination of phthalate ester plasticizers in the aquatic environment using hollow fibre supported liquid membranes

NASA Astrophysics Data System (ADS)

Mtibe, A.; Msagati, Titus A. M.; Mishra, Ajay K.; Mamba, Bhekie B.

Phthalates are known to be carcinogenic, teratogenic as well as endocrine disruptors. The potential risk to human and animals health generated from them has drawn great attention all over the world. Hollow fibre supported liquid membrane (HFSLM) online with high pressure liquid chromatography (HPLC) was used to determine benzyl butyl phthalate (BBP), dibutyl phthalate (DBP) and Diethylhexyl phthalate (DEHP) in wastewater. Toluene, di-n-hexyl ether and undecane were used as liquid barriers separating both donor (sample) and acceptor phase. Toluene performed much better than undecane and was used in sample preparation. The presence of toluene showed the potential for the enrichment and removal of phthalates to the concentrations ranges from 0 to 1.7 mg L-1.

Occurrence and risk assessment of phthalate esters (PAEs) in vegetables and soils of suburban plastic film greenhouses.

PubMed

Wang, Jun; Chen, Gangcai; Christie, Peter; Zhang, Manyun; Luo, Yongming; Teng, Ying

2015-08-01

Phthalate esters (PAEs) are suspected of having adverse effects on human health and have been frequently detected in soils and vegetables. The present study investigated their occurrence and composition in plastic film greenhouse soil-vegetable systems and assessed their potential health risks to farmers exposed to these widespread pollutants. Six priority control phthalates, namely dimethyl phthalate (DMP), diethyl phthalate (DEP), di-n-butyl phthalate (DnBP), butyl benzyl phthalate (BBP), di-(2-ethylhexyl) phthalate (DEHP) and di-n-octyl phthalate (DnOP), were determined in 44 plastic film greenhouse vegetables and corresponding soils. Total PAEs ranged from 0.51 to 7.16mgkg(-1) in vegetables and 0.40 to 6.20mgkg(-1) in soils with average concentrations of 2.56 and 2.23mgkg(-1), respectively. DnBP, DEHP and DnOP contributed more than 90% of the total PAEs in both vegetables and soils but the proportions of DnBP and DnOP in vegetables were significantly (p<0.05) higher than in soils. The average concentrations of PAEs in pot herb mustard, celery and lettuce were >3.00mgkg(-1) but were <2.50mgkg(-1) in the corresponding soils. Stem and leaf vegetables accumulated more PAEs. There were no clear relationships between vegetable and soil PAEs. Risk assessment indicates that DnBP, DEHP and DnOP exhibited elevated non-cancer risk with values of 0.039, 0.338 and 0.038, respectively. The carcinogenic risk of DEHP was about 3.94×10(-5) to farmers working in plastic film greenhouses. Health risks were mainly by exposure through vegetable consumption and soil ingestion. Copyright © 2015 Elsevier B.V. All rights reserved.

GC/MS screening method for phthalate esters in children's toys.

PubMed

Ting, Keh-Chuh; Gill, Modan; Garbin, Orlando

2009-01-01

Phthalate esters are commonly added into polyvinyl chloride (PVC) as softeners to make the plastic material flexible. Phthalates are suspected cancer-causing agents and possible teratogens; they have been linked to liver and kidney damage, as well as the underdevelopment of reproductive organs in humans and animals. Public safety concerns about human exposure to phthalates are on the rise because they do not chemically bond to PVC and leach from the material over time. Following the lead of the European Union and Japan in restricting the use of certain phthalates, a legal limit of 0.1% in children's toys was established by the California State Legislature (AB-1108). In addition to its mission to protect public health and the environment from toxic harm, the California Department of Toxic Substances Control (DTSC) has been delegated the role of lead agency for consumer product safety. To support DTSC's Green Chemistry activities, the Environmental Chemistry Laboratory Mobile Laboratory Team has developed an on-site screening method to monitor phthalates in children's toys. This method is simple, fast, and effective, with ample sensitivity to quantify the 6 restricted phthalates in children's toys at 100 ppm (limit of quantitation = 100 microg/g) which is 10 times lower than the legal allowable level of 0.1%. Additionally, the method has a high throughput capability and enables testing of approximately 6-10 samples per day, depending on the complexity of the sample matrix and concentration. This method is designed to survey the 6 phthalates in children's toys and other consumer products for compliance with the threshold of 0.1% (1000 ppm).

Differential expression of the phthalate syndrome in male Sprague-Dawley and Wistar rats after in utero DEHP exposure

EPA Science Inventory

Exposure to phthalate esters during sexual differentiation disrupts testosterone and insulin-like three hormones resulting in malformations of androgen- and insulin-like three-dependent tissues. The current study was designed to test the hypothesis that gubernacular lesions would...

A FETAL RAT TESTIS ENDOCRINE AND GENOMIC "SIGNATURE"ACCURATELY PREDICTS THE PHTHALATE SYNDROME OF MALFORMATIONS.

EPA Science Inventory

ABSTRACT BODY: Phthalate esters (PE) vary greatly in their potency to induce malformations during sexual differentiation in the male rat. Since in vitro assay batteries are currently unable to generate useful information on the potential of chemicals within this class to disrupt ...

The Plasticizer Diethylhexyl Phthalate Induces Malformations by Decreasing Fetal Testosterone Synthesis Durin Sexual Differentiation in the Male Rat

EPA Science Inventory

Phthalate esters (PE) like DEHP are high production volume plasticizers used in vinyl floors, food wraps, cosmetics, medical products and toys. In spite of their widespread and long-term use, most PEs have not been adequately tested for transgenerational reproductive toxicity. ...

Inhibitory mechanism of phthalate esters on Karenia brevis.

PubMed

Liu, Ning; Wen, Fuling; Li, Fengmin; Zheng, Xiang; Liang, Zhi; Zheng, Hao

2016-07-01

The occurrence of phthalate esters (PAEs), a class of widely used and environmentally prevalent chemicals, raises concern to environmental and human health globally. The PAEs have been demonstrated to inhibit algae growth, but the underlying mechanisms remain unclear. In this research, diethyl ortho-phthalate (DEP), diallyl phthalate (DAP), di-n-butyl ortho-phthalate (DBP), di-iso-butyl ortho-phthalate, and benzyl-n-butyl ortho-phthalate (BBP) were screened from 11 species of PAEs to study their inhibitory effects on Karenia brevis and determine their target sites on algae. With increasing the alkyl chains of these five PAEs, the values of EC50,96h decreased. The content of malondialdehyde increased with the continuous accumulation of reactive oxygen species (ROS) in the algae cells. Moreover, the superoxide dismutase and catalase contents were first activated and then inhibited. The ultrastructures of Karenia brevis cells were detected by transmission electron microscopy, and cells treated with PAEs exhibiting distorted shapes and large vacuoles. Thus, the algae were damaged by ROS accumulation, resulting in lipid oxidation and algal growth inhibition. The inhibitors of the electron transport chain showed that the sites of ROS production and accumulation in K. brevis cells under DEP and BBP were the mitochondria and chloroplast, respectively. Moreover, the target sites of DAP and DBP were both the chloroplast and mitochondria. These results are useful for controlling PAEs contamination in and revealing the fate of PAEs in aquatic ecosystem. Copyright © 2016 Elsevier Ltd. All rights reserved.

Concentration and source identification of polycyclic aromatic hydrocarbons and phthalic acid esters in the surface water of the Yangtze River Delta, China.

PubMed

Zhang, Lifei; Dong, Liang; Ren, Lijun; Shi, Shuangxin; Zhou, Li; Zhang, Ting; Huang, Yeru

2012-01-01

The pollution from polycyclic aromatic hydrocarbons (PAHs) and phthalic acid esters (PAEs) in the surface water of the rapidly urbanized Yangtze River Delta region was investigated. Fourteen surface water samples were collected in June 2010. Water samples were liquid-liquid extracted using methylene chloride and analyzed by gas chromatography-mass spectrometry. Concentrations of PAHs and PAEs ranged 12.9-638.1 ng/L and 61-28550 ng/L, respectively. Fluoranthene, naphthalene, pyrene, phenanthrene, di-2-ethylhexyl phthalate, and di-n-butyl phthalate were the most abundant compounds in the samples. The water samples were moderately polluted with benzo[a]pyrene according to China's environmental quality standard for surface water. The two highest concentrations of PAHs and PAEs occurred in samples from Taihu Lake, Wuxi City and the western section of Yangchenghu Lake. Potential sources of pollution at S7 were petroleum combustion and the plastics industry, and at Yangchenghu Lake were petroleum combustion and domestic waste. Pollution in samples from the Beijing-Hangzhou Grand Canal originated from diesel engines. There were no obvious sources of pollution for the other water samples. These results can be used as reference levels for future monitoring programs of pollution from PAHs and PAEs.

Contamination of phthalate esters, organochlorine pesticides and polybrominated diphenyl ethers in agricultural soils from the Yangtze River Delta of China.

PubMed

Sun, Jianteng; Pan, Lili; Zhan, Yu; Lu, Hainan; Tsang, Daniel C W; Liu, Wenxin; Wang, Xilong; Li, Xiangdong; Zhu, Lizhong

2016-02-15

To reveal the pollution status associated with rapid urbanization and economic growth, extensive areas of agricultural soils (approximately 45,800 km(2)) in the Yangtze River Delta of China were investigated with respect to selected endocrine disruptor compounds (EDCs), including phthalate esters (PAEs), organochlorine pesticides (OCPs) and polybrominated diphenyl ethers (PBDEs). The residues of sum of 15 PAEs, sum of 15 OCPs and sum of 13 PBDEs were in the range of 167-9370 ng/g, 1.0-3520 ng/g, and <1.0-382 ng/g, respectively. The OCPs residuals originated from both historical usage and recent input. Agricultural plastic film was considered to be an important source of PAEs. Discharge from furniture industry was potential major source of PBDEs in this region. The selected pollutants showed quite different spatial distributions within the studied region. It is worth noting that much higher concentrations of the EDCs were found on the borders between Shanghai and the two neighboring provinces, where agriculture and industry developed rapidly in recent years. Contaminants from both agricultural and industrial activities made this area a pollution hotspot, which should arouse more stringent regulation to safeguard the environment and food security. Copyright © 2015 Elsevier B.V. All rights reserved.

Monitoring and removal of residual phthalate esters and pharmaceuticals in the drinking water of Kaohsiung City, Taiwan.

PubMed

Yang, Gordon C C; Yen, Chia-Heng; Wang, Chih-Lung

2014-07-30

This study monitored the occurrence and removal efficiencies of 8 phthalate esters (PAEs) and 13 pharmaceuticals present in the drinking water of Kaohsiung City, Taiwan. The simultaneous electrocoagulation and electrofiltration (EC/EF) process was used to remove the contaminants. To this end, a monitoring program was conducted and a novel laboratory-prepared tubular carbon nanofiber/carbon/alumina composite membrane (TCCACM) was incorporated into the EC/EF treatment module (collectively designated as "TCCACM-EC/EF treatment module") to remove the abovementioned compounds from water samples. The monitoring results showed that the concentrations of PAEs were lower in water samples from drinking fountains as compared with tap water samples. No significant differences were found between the concentrations of pharmaceuticals in the two types of water samples. Under optimal operating conditions, the TCCACM-EC/EF treatment module yielded the lowest residual concentrations, ranging from not detected (ND) to 52ng/L for PAEs and pharmaceuticals of concern in the tap water samples. Moreover, the performance of the TCCACM-EC/EF treatment module is comparable with a series of treatment units employed for the drinking fountain water treatment system. The relevant removal mechanisms involved in the TCCACM-EC/EF treatment module were also discussed in this work. Copyright © 2014 Elsevier B.V. All rights reserved.

Novel double-confined polymeric ionic liquids as sorbents for solid-phase microextraction with enhanced stability and durability in high-ionic-strength solution.

PubMed

Feng, Juanjuan; Sun, Min; Xu, Lili; Wang, Shuai; Liu, Xia; Jiang, Shengxiang

2012-12-14

Because of the occurrence of ion exchange between high-ionic-strength solution and anions of polymeric ionic liquids (PILs), PILs based solid-phase microextraction (SPME) fibers were rarely used in direct immersion mode to high-salt-added samples. In this work, a novel double-confined PIL sorbent was prepared by co-polymerization of cation and anion of 1-vinyl-3-octylimidzaolium p-styrenesulfonate (VOIm(+)SS(-)). The poly(VOIm(+)-SS(-)) was chemically bonded onto functionalized stainless steel wire via surface radical chain-transfer reaction. Stability of poly(VOIm(+)-SS(-)) in high-ionic-strength solution was investigated and compared with that of poly(1-vinyl-3-octylimidzaolium benzenesulfonate) (poly(VOIm(+)BS(-))) by elemental analysis of sulfur element, and results turned out that the poly(VOIm(+)-SS(-)) was more stable. Coupled to gas chromatography (GC), the poly(VOIm(+)-SS(-)) fiber was used to extract three sorts of compounds including anilines, phenols and phthalate esters in aqueous solution. The as-established method showed good linearity, low detection limits, and acceptable repeatability. The direct immersion SPME-GC method was applied to determine the model phthalate esters in bottled mineral water. The determination results were satisfactory. Copyright © 2012 Elsevier B.V. All rights reserved.

Evaluating the potential genotoxicity of phthalates esters (PAEs) in perfumes using in vitro assays.

PubMed

Al-Saleh, Iman; Al-Rajudi, Tahreer; Al-Qudaihi, Ghofran; Manogaran, Pulicat

2017-10-01

We previously reported high levels of phthalate esters (PAEs) added as solvents or fixatives in 47 brands of perfumes. Diethyl phthalate was the most abundant compound (0.232-23,649 ppm), and 83.3% of the perfumes had levels >1 ppm, the threshold limit cited by a Greenpeace investigation. All samples had dimethyl phthalate levels higher than its threshold limit of 0.1 ppm, and 88, 38, and 7% of the perfumes had benzyl butyl phthalate, di(2-ethylhexyl) phthalate, and dibutyl phthalate levels, respectively, above their threshold limits. The role of PAEs as endocrine disruptors has been well documented, but their effect on genotoxic behavior has received little attention. We used in vitro single-cell gel electrophoresis (comet) and micronucleus (MN) assays with human lymphoblastoid TK6 cells to evaluate the genotoxic potency of 42 of the same perfumes and to determine its association with PAEs. All perfumes induced more DNA damage than a negative control (NEG), ≥ 90% of the samples caused more damage than cells treated with the vehicles possibly used in perfume's preparations such as methanol (ME) and ethanol (ET), and 11.6% of the perfumes caused more DNA damage than a positive control (hydrogen peroxide). Chromosome breakage expressed as MN frequency was higher in cells treated with 71.4, 64.3, 57.1, and 4.8% of the perfumes than in NEG, cells treated with ME or ET, and another positive control (x-rays), respectively. The genotoxic responses in the comet and MN assays were not correlated. The comet assay indicated that the damage in TK6 cells treated with five PAEs at concentrations of 0.05 and 0.2 ppm either individually or as a mixture did not differ significantly from the damage in cells treated with the perfumes. Unlike the comet assay, the sensitivity of the MN assay to PAEs was weak at both low and high concentrations, and MN frequencies were generally low. This study demonstrates for the first time the possible contribution of PAEs in perfumes to DNA damage and suggests that their use as solvents or fixatives should be regulated. Other ingredients with mutagenic/genotoxic properties, however, may also have contributed to the DNA damage. Future studies should focus on applying a series of assays that use different cellular models with various endpoints to identify the spectrum of genotoxic mechanisms involved.

Comparison of fetal testosterone production in various tissues of the male sprague dawley rat dosed in utero with dipentyl phthalate during the critical window of sexual differentiation

EPA Science Inventory

Phthalate esters are high-production volume chemicals used in the manufacture of numerous plastics and consumer products, which generates major concern for potential human exposure and environmental contamination. Several studies have demonstrated adverse effects associated with ...

Dose additive effects of simvastatin and dipentyl phthalate on testosterone production in the fetal testis: A cummulative risk perspective

EPA Science Inventory

Sex differentiation of the mammalian reproductive tract is a highly regulated process that is driven, in part, by fetal testosterone (T) production. In utero exposure to phthalate esters (PE) during sex differentiation can cause reproductive tract malformations in rats. PE alter ...

Simvastatin and dipentyl phthalate lower testosterone production and exhibit dose additive effects on the fetal testis via distinct mechanistic pathways

EPA Science Inventory

Sex differentiation of the mammalian reproductive tract is a highly regulated process that is driven, in part, by fetal testosterone (T) production. In utero exposure to phthalate esters (PE) during sex differentiation can result in reproductive tract malformations in rats. PE al...

Genomic biomarkers of phthalate-induced male reproductive developmental toxicity: A targeted rtPCR array approach for defining relative potency

EPA Science Inventory

Male rat fetuses exposed to certain phthalate esters (PEs) during sexual differentiation display reproductive tract malformations due to reductions in testosterone (T) production and the expression of steroidogenesis-and INSL3-related genes. In the current study} we used a 96well...

Evaluation of genomic biomarkers and relative potency of phthalate-induced male reproductive developmental toxicity using a targeted rtPCR array approach**

EPA Science Inventory

Exposure to certain phthalate esters (PEs) during sexual differentiation induces reproductive tract malformations in male rats due to reductions in fetal testicular testosterone (T) production and expression of steroidogenesis-and insl3-related genes. In the current study, we use...

Decreased serum free testosterone in workers exposed to high levels of di-n-butyl phthalate (DBP) and di-2-ethylhexyl phthalate (DEHP): a cross-sectional study in China.

PubMed

Pan, Guowei; Hanaoka, Tomoyuki; Yoshimura, Mariko; Zhang, Shujuan; Wang, Ping; Tsukino, Hiromasa; Inoue, Koichi; Nakazawa, Hiroyuki; Tsugane, Shoichiro; Takahashi, Ken

2006-11-01

Observations of adverse developmental and reproductive effects in laboratory animals and wildlife have fueled increasing public concern regarding the potential for various chemicals to impair human fertility. Our objective in this study was to assess the effect of occupational exposure to high levels of phthalate esters on the balance of gonadotropin and gonadal hormones including luteinizing hormone, follicle-stimulating hormone, free testosterone (fT), and estradiol. We examined urine and blood samples of 74 male workers at a factory producing unfoamed polyvinyl chloride flooring exposed to di-n-butyl phthalate (DBP) and di-2-ethylhexyl phthalate (DEHP) and compared them with samples from 63 male workers from a construction company, group matched for age and smoking status. Compared to the unexposed workers, the exposed workers had substantially and significantly elevated concentrations of mono-n-butyl phthalate (MBP; 644.3 vs. 129.6 microg/g creatinine, p < 0.001) and mono-2-ethylhexyl phthalate (MEHP; 565.7 vs. 5.7 microg/g creatinine, p < 0.001). fT was significantly lower (8.4 vs. 9.7 microg/g creatinine, p = 0.019) in exposed workers than in unexposed workers. fT was negatively correlated to MBP (r = -0.25, p = 0.03) and MEHP (r = -0.19, p = 0.095) in the exposed worker group. Regression analyses revealed that fT decreases significantly with increasing total phthalate ester score (the sum of quartiles of MBP and MEHP; r = -0.26, p = 0.002). We observed a modest and significant reduction of serum fT in workers with higher levels of urinary MBP and MEHP compared with unexposed workers.

Decreased Serum Free Testosterone in Workers Exposed to High Levels of Di-n-butyl Phthalate (DBP) and Di-2-ethylhexyl Phthalate (DEHP): A Cross-Sectional Study in China

PubMed Central

Pan, Guowei; Hanaoka, Tomoyuki; Yoshimura, Mariko; Zhang, Shujuan; Wang, Ping; Tsukino, Hiromasa; Inoue, Koichi; Nakazawa, Hiroyuki; Tsugane, Shoichiro; Takahashi, Ken

2006-01-01

Background Observations of adverse developmental and reproductive effects in laboratory animals and wildlife have fueled increasing public concern regarding the potential for various chemicals to impair human fertility. Objective Our objective in this study was to assess the effect of occupational exposure to high levels of phthalate esters on the balance of gonadotropin and gonadal hormones including luteinizing hormone, follicle-stimulating hormone, free testosterone (fT), and estradiol. Methods We examined urine and blood samples of 74 male workers at a factory producing unfoamed polyvinyl chloride flooring exposed to di-n-butyl phthalate (DBP) and di-2-ethylhexyl phthalate (DEHP) and compared them with samples from 63 male workers from a construction company, group matched for age and smoking status. Results Compared to the unexposed workers, the exposed workers had substantially and significantly elevated concentrations of mono-n-butyl phthalate (MBP; 644.3 vs. 129.6 μg/g creatinine, p < 0.001) and mono-2-ethylhexyl phthalate (MEHP; 565.7 vs. 5.7 μg/g creatinine, p < 0.001). fT was significantly lower (8.4 vs. 9.7 μg/g creatinine, p = 0.019) in exposed workers than in unexposed workers. fT was negatively correlated to MBP (r = −0.25, p = 0.03) and MEHP (r = −0.19, p = 0.095) in the exposed worker group. Regression analyses revealed that fT decreases significantly with increasing total phthalate ester score (the sum of quartiles of MBP and MEHP; r = −0.26, p = 0.002). Conclusion We observed a modest and significant reduction of serum fT in workers with higher levels of urinary MBP and MEHP compared with unexposed workers. PMID:17107847

Human Elimination of Phthalate Compounds: Blood, Urine, and Sweat (BUS) Study

PubMed Central

Genuis, Stephen J.; Beesoon, Sanjay; Lobo, Rebecca A.; Birkholz, Detlef

2012-01-01

Background. Individual members of the phthalate family of chemical compounds are components of innumerable everyday consumer products, resulting in a high exposure scenario for some individuals and population groups. Multiple epidemiological studies have demonstrated statistically significant exposure-disease relationships involving phthalates and toxicological studies have shown estrogenic effects in vitro. Data is lacking in the medical literature, however, on effective means to facilitate phthalate excretion. Methods. Blood, urine, and sweat were collected from 20 individuals (10 healthy participants and 10 participants with assorted health problems) and analyzed for parent phthalate compounds as well as phthalate metabolites using high performance liquid chromatography-tandem mass spectrometry. Results. Some parent phthalates as well as their metabolites were excreted into sweat. All patients had MEHP (mono(2-ethylhexyl) phthalate) in their blood, sweat, and urine samples, suggesting widespread phthalate exposure. In several individuals, DEHP (di (2-ethylhexl) phthalate) was found in sweat but not in serum, suggesting the possibility of phthalate retention and bioaccumulation. On average, MEHP concentration in sweat was more than twice as high as urine levels. Conclusions. Induced perspiration may be useful to facilitate elimination of some potentially toxic phthalate compounds including DEHP and MEHP. Sweat analysis may be helpful in establishing the existence of accrued DEHP in the human body. PMID:23213291

Comparison of Fetal Testosterone Production in Various Tissues of the Male Sprague Dawley Rat dosed In Utero with Dipentyl Phthalate during the Critical Window of Sexual Differentiation###

EPA Science Inventory

Phthalate esters are high-production volume chemicals used in the manufacture of numerci plastics and consumer products, which generates major concern for potential human exposure and environmental contamination. Several studies have demonstrated adverse effects associated with p...

Are anti-androgenic effects of phthalates on the fetal testis mediated via a peroxisome proliferator activated receptor-α (PPAR-α) associated molecular initiating event?

EPA Science Inventory

In utero exposure to certain phthalate esters (PE) during the critical window of male sex differentiation reduces both fetal testis testosterone (T) production and expression of steroid transport and synthesis genes, resulting in reproductive tract malformations in adult male rod...

Simvastatin and Dipentyl Phthalate Display Different Mechanisms of Action but Exhibit Dose Additive Effects on Fetal Testicular Testosterone Production in Sprague Dawley Rats

EPA Science Inventory

Sex differentiation of the male reproductive tract in mammals is driven, in part, by fetal androgen production. In utero exposure to some phthalate esters (PEs) alters fetal Leydig cell differentiation, reducing the expression of several genes associated with steroid synthesis/tr...

Removal of phthalate esters from aqueous solutions by chitosan bead.

PubMed

Chen, Chih-Yu; Chung, Ying-Chien

2006-01-01

Removal of phthalate esters (PAEs) by chitosan bead in aqueous solution was studied. The adsorption isotherms of PAEs by chitosan bead were well described by Freundlich isotherm equations. Results of kinetic experiments indicated that diheptyl phthalate (DHpP) had the highest adsorption capacity (1.52 mg/g) among six PAEs in our research. PAE adsorption efficiency by chitosan bead was examined in both batch and continuous systems, and DHpP attained 74.9% recovery efficiency from chitosan bead by shaking with an equal volume mixture of methanol and water. The recovered chitosan bead was reusable as an adsorbent. The influences of temperature, pH, Ca+2, and NaCl on PAE adsorption were also evaluated to determine performance in different water environments (e.g., groundwater, surface water, and sea water). The results showed that PAE adsorption decreased as temperature increased. From pH experiments it appeared that pH 8.0 was optimal for adsorption. The effect of Ca+2 showed that adsorption efficiency did not change by increasing the concentrations of Ca+2 until 400 mg/L. NaCl coexistence showed an insignificant effect on PAE adsorption. Furthermore, the chitosan bead was also applied to treating the discharge of a plastics plant, and the treatment results resembled those of a laboratory continuous system. This is the first report to use chitosan bead as an adsorbent to adsorb phthalate esters from aqueous solution. These results indicate that the application of chitosan bead is feasible in the aqueous environments of Taiwan.

Phthalic acid esters in soils from vegetable greenhouses in Shandong Peninsula, East China.

PubMed

Chai, Chao; Cheng, Hongzhen; Ge, Wei; Ma, Dong; Shi, Yanxi

2014-01-01

Soils at depths of 0 cm to 10 cm, 10 cm to 20 cm, and 20 cm to 40 cm from 37 vegetable greenhouses in Shandong Peninsula, East China, were collected, and 16 phthalic acid esters (PAEs) were detected using gas chromatography-mass spectrometry (GC-MS). All 16 PAEs could be detected in soils from vegetable greenhouses. The total of 16 PAEs (Σ16PAEs) ranged from 1.939 mg/kg to 35.442 mg/kg, with an average of 6.748 mg/kg. Among four areas, including Qingdao, Weihai, Weifang, and Yantai, the average and maximum concentrations of Σ16PAEs in soils at depths of 0 cm to 10 cm appeared in Weifang, which has a long history of vegetable production and is famous for extensive greenhouse cultivation. Despite the different concentrations of Σ16PAEs, the PAE compositions were comparable. Among the 16 PAEs, di(2-ethylhexyl) phthalate (DEHP), di-n-octyl phthalate (DnOP), di-n-butyl phthalate (DnBP), and diisobutyl phthalate (DiBP) were the most abundant. Compared with the results on agricultural soils in China, soils that are being used or were used for vegetable greenhouses had higher PAE concentrations. Among PAEs, dimethyl phthalate (DMP), diethyl phthalate (DEP) and DnBP exceeded soil allowable concentrations (in US) in more than 90% of the samples, and DnOP in more than 20%. Shandong Peninsula has the highest PAE contents, which suggests that this area is severely contaminated by PAEs.

Phthalic Acid Esters in Soils from Vegetable Greenhouses in Shandong Peninsula, East China

PubMed Central

Chai, Chao; Cheng, Hongzhen; Ge, Wei; Ma, Dong; Shi, Yanxi

2014-01-01

Soils at depths of 0 cm to 10 cm, 10 cm to 20 cm, and 20 cm to 40 cm from 37 vegetable greenhouses in Shandong Peninsula, East China, were collected, and 16 phthalic acid esters (PAEs) were detected using gas chromatography-mass spectrometry (GC-MS). All 16 PAEs could be detected in soils from vegetable greenhouses. The total of 16 PAEs (Σ16PAEs) ranged from 1.939 mg/kg to 35.442 mg/kg, with an average of 6.748 mg/kg. Among four areas, including Qingdao, Weihai, Weifang, and Yantai, the average and maximum concentrations of Σ16PAEs in soils at depths of 0 cm to 10 cm appeared in Weifang, which has a long history of vegetable production and is famous for extensive greenhouse cultivation. Despite the different concentrations of Σ16PAEs, the PAE compositions were comparable. Among the 16 PAEs, di(2-ethylhexyl) phthalate (DEHP), di-n-octyl phthalate (DnOP), di-n-butyl phthalate (DnBP), and diisobutyl phthalate (DiBP) were the most abundant. Compared with the results on agricultural soils in China, soils that are being used or were used for vegetable greenhouses had higher PAE concentrations. Among PAEs, dimethyl phthalate (DMP), diethyl phthalate (DEP) and DnBP exceeded soil allowable concentrations (in US) in more than 90% of the samples, and DnOP in more than 20%. Shandong Peninsula has the highest PAE contents, which suggests that this area is severely contaminated by PAEs. PMID:24747982

Biodegradation of phthalic acid esters by a newly isolated Mycobacterium sp. YC-RL4 and the bioprocess with environmental samples.

PubMed

Ren, Lei; Jia, Yang; Ruth, Nahurira; Qiao, Cheng; Wang, Junhuan; Zhao, Baisuo; Yan, Yanchun

2016-08-01

Bacterial strain YC-RL4, capable of utilizing phthalic acid esters (PAEs) as the sole carbon source for growth, was isolated from petroleum-contaminated soil. Strain YC-RL4 was identified as Mycobacterium sp. by 16S rRNA gene analysis and Biolog tests. Mycobacterium sp. YC-RL4 could rapidly degrade dibutyl phthalate (DBP), diethyl phthalate (DEP), dimethyl phthalate (DMP), dicyclohexyl phthalate (DCHP), and di-(2-ethylhexyl) phthalate (DEHP) under both individual and mixed conditions, and all the degradation rates were above 85.0 % within 5 days. The effects of environmental factors which might affect the degrading process were optimized as 30 °C and pH 8.0. The DEHP metabolites were detected by HPLC-MS and the degradation pathway was deduced tentatively. DEHP was transformed into phthalic acid (PA) via mono (2-ethylhexyl) phthalate (MEHP) and PA was further utilized for growth via benzoic acid (BA) degradation pathway. Cell surface hydrophobicity (CSH) assays illuminated that the strain YC-RL4 was of higher hydrophobicity while grown on DEHP and CSH increased with the higher DEHP concentration. The degradation rates of DEHP by strain YC-RL4 in different environmental samples was around 62.0 to 83.3 % and strain YC-RL4 survived well in the soil sample. These results suggested that the strain YC-RL4 could be used as a potential and efficient PAE degrader for the bioremediation of contaminated sites.

Ionization of EPA Contaminants in Direct and Dopant-Assisted Atmospheric Pressure Photoionization and Atmospheric Pressure Laser Ionization

NASA Astrophysics Data System (ADS)

Kauppila, Tiina J.; Kersten, Hendrik; Benter, Thorsten

2015-06-01

Seventy-seven EPA priority environmental pollutants were analyzed using gas chromatography-mass spectrometry (GC-MS) equipped with an optimized atmospheric pressure photoionization (APPI) and an atmospheric pressure laser ionization (APLI) interface with and without dopants. The analyzed compounds included e.g., polycyclic aromatic hydrocarbons (PAHs), nitro compounds, halogenated compounds, aromatic compounds with phenolic, acidic, alcohol, and amino groups, phthalate and adipatic esters, and aliphatic ethers. Toluene, anisole, chlorobenzene, and acetone were tested as dopants. The widest range of analytes was ionized using direct APPI (66/77 compounds). The introduction of dopants decreased the amount of compounds ionized in APPI (e.g., 54/77 with toluene), but in many cases the ionization efficiency increased. While in direct APPI the formation of molecular ions via photoionization was the main ionization reaction, dopant-assisted (DA) APPI promoted ionization reactions, such as charge exchange and proton transfer. Direct APLI ionized a much smaller amount of compounds than APPI (41/77 compounds), showing selectivity towards compounds with low ionization energies (IEs) and long-lived resonantly excited intermediate states. DA-APLI, however, was able to ionize a higher amount of compounds (e.g. 51/77 with toluene), as the ionization took place entirely through dopant-assisted ion/molecule reactions similar to those in DA-APPI. Best ionization efficiency in APPI and APLI (both direct and DA) was obtained for PAHs and aromatics with O- and N-functionalities, whereas nitro compounds and aliphatic ethers were the most difficult to ionize. Halogenated aromatics and esters were (mainly) ionized in APPI, but not in APLI.

Recent progress in safety evaluation studies on plasticizers and plastics and their controlled use in Japan.

PubMed Central

Omori, Y

1976-01-01

Recent experimental studies in Japan on the evaluation of potential health hazards from phthalate esters used in manufacturing poly (vinyl chloride) as well as several plastics for medical devices and for food containers and packages were introduced. Development of pulmonary granuloma formation after intravenous injection of diethylhexyl phthalate was assumed to be dependent on the particle size of the phthalate in vehicle used. Dietary administration of large amount of diethylhexyl phthalate and dibutyl phthalate produced renal cysts in mothers and in descendants in reproduction studies in mice. Cytotoxicity and mutagenicity of the phthalates and several plastics and resins were also examined by in vivo and in vitro studies. Hematological parameters examined in rabbits after repeated intravenous injection of diethylhexyl phthalate and after implantation of plastics in aorta for 3--6 months did not show any significant change. A slow decrease of radioactivity was observed in adipose tissue of rats following oral administration of 14C-labeled diethylhexyl phthalate. tthe administrative action on phthalates by the Japanese Ministry of Health and Welfare is briefly reviewed. PMID:1026406

Simvastatin and Dipentyl Phthalate Lower Ex vivo Testicular Testosterone Production and Exhibit Additive Effects on Testicular Testosterone and Gene Expression Via Distinct Mechanistic Pathways in the Fetal Rat

EPA Science Inventory

Sex differentiation of the male reproductive tract in mammals is driven, in part, by fetal androgen production. In utero, some phthalate esters (PEs) alter fetal Leydig cell differentiation, reducing the expression of several genes associated with steroid synthesis/transport, and...

Status of phthalate esters contamination in agricultural soils across China and associated health risks.

PubMed

Niu, Lili; Xu, Yang; Xu, Chao; Yun, Lingxiang; Liu, Weiping

2014-12-01

The extensive utilization of phthalate-containing products has lead to ubiquitous contamination of phthalate esters (PAEs) in various matrices. However, comprehensive knowledge of their pollution in Chinese farmland and associated risks is still limited. In this study, 15 PAEs were determined in soils from agricultural fields throughout the Mainland China. The concentrations of Σ15PAEs were in the range of 75.0-6369 μg kg(-1). Three provinces (i.e., Fujian, Guangdong and Xinjiang, China) showed the highest loadings of PAEs. Bis(2-Ethylhexyl) phthalate (DEHP) was found as the most abundant component and contributed 71.5% to the ∑15PAEs. The major source of PAEs in arable soils was associated with the application of agricultural plastic films, followed by the activities for soil fertility. Furthermore, the non-cancer and carcinogenic risks of target PAEs were estimated. The hazard indexes (HIs) of PAEs in all samples were below 1 and the carcinogenic risk levels were all within 10(-4). Results from this study will provide valuable information for Chinese agricultural soil management and risk avoidance. Copyright © 2014 Elsevier Ltd. All rights reserved.

Pollution characteristics and health risk assessment of phthalate esters in urban soil in the typical semi-arid city of Xi'an, Northwest China.

PubMed

Wang, Lijun; Liu, Mengmei; Tao, Wendong; Zhang, Wenjuan; Wang, Li; Shi, Xingmin; Lu, Xinwei; Li, Xiaoping

2018-01-01

A total of 62 urban soil samples were collected in the city of Xi'an in Northwest China, and analyzed for six U.S. Environmental Protection Agency priority phthalate esters (PAEs). Unlike earlier studies on PAEs in agricultural soil as well as urban soil in humid climates, this paper for the first time comprehensively assessed pollution characteristics and health risks of human exposure to PAEs in urban soil in a typical semi-arid climate. The total concentrations of the six PAEs (Σ6PAEs) in the urban soil varied between 193.0 and 19146.4 μg kg -1 with a mean of 1369.3 μg kg -1 . The PAEs were dominated by di-n-butyl phthalate and di(2-ethylhexyl) phthalate. Magnetic susceptibility and soil texture were controlling factors influencing the concentrations of PAEs in the urban soil. The concentrations of benzyl butyl phthalate, di(2-ethylhexyl) phthalate, and Σ6PAEs increased from the first to third ring roads, while the concentrations of di-n-octyl phthalate decreased. Relatively higher levels of PAEs were observed in industrial, traffic, and residential areas. The PAEs in the urban soil originated mainly from the application of plasticizers or additives, use of cosmetics and personal care products, emissions of construction materials and home furnishings, industrial processes, and atmospheric deposition. The concentrations of some PAEs in the urban soil exceeded soil allowable concentrations and environmental risk levels. The non-cancer and carcinogenic risks of human exposure to the PAEs were relatively low. Copyright © 2017 Elsevier Ltd. All rights reserved.

Seasonal fate and gas/particle partitioning of semi-volatile organic compounds in indoor and outdoor air

NASA Astrophysics Data System (ADS)

Moreau-Guigon, Elodie; Alliot, Fabrice; Gaspéri, Johnny; Blanchard, Martine; Teil, Marie-Jeanne; Mandin, Corinne; Chevreuil, Marc

2016-12-01

Fifty-eight semi-volatile organic compounds (SVOCs) were investigated simultaneously in three indoor (apartment, nursery and office building) and one outdoor environment in the centre of Paris (France). All of these compounds except tetrabromobisphenol A were quantified in the gaseous and particulate phases in all three environments, and at a frequency of 100% for the predominant compounds of each SVOC class. Phthalic acid esters (PAEs) were the most abundant group (di-iso-butyl phthalate: 29-661 ng m-3, diethyl phthalate: 15-542 ng m-3), followed by 4-nonylphenol (1.4-81 ng m-3), parabens (methylparaben: 0.03-2.5 ng m-3), hexachlorobenzene (HCB) (0.002-0.26 ng m-3) and pentachlorobenzene (PeCB) (0.001-0.23 ng m-3). Polycyclic aromatic hydrocarbons (as ∑8PAHs) ranged from 0.17 to 5.40 ng m-3, polychlorinated biphenyls (as ∑7PCBi) from 0.06 to 4.70 ng.m3 and polybromodiphenyl ethers (as ∑8PBDEs) from 0.002 to 0.40 ng m-3. For most pollutants, significantly higher concentrations were observed in the nursery compared to the apartment and office. Overall, the indoor air concentrations were up to ten times higher than outdoor air concentrations. Seasonal variations were observed for PAEs, PCBs and PAHs. SVOCs were predominantly identified in the gaseous phase (>90%), except for some high-molecular-weight PAEs, PAHs and PCBs.

Determining Phthalic Acid Esters Using Terahertz Time Domain Spectroscopy

NASA Astrophysics Data System (ADS)

Liu, L.; Shen, L.; Yang, F.; Han, F.; Hu, P.; Song, M.

2016-09-01

In this report terahertz time domain spectroscopy (THz-TDS) is applied for determining phthalic acid esters (PAEs) in standard materials. We reported the THz transmission spectrum in the frequency range of 0.2 to 2.0 THz for three PAEs: di-n-butyl phthalate (DBP), di-isononyl phthalate (DINP), and di-2-ethylhexyl phthalate ester (DEHP). The study provided the refractive indices and absorption features of these materials. The absorption spectra of three PAEs were simulated by using Gaussian software with Density Functional Theory (DFT) methods. For pure standard PAEs, the values of the refractive indices changed between 1.50 and 1.60. At 1.0 THz, the refractive indices were 1.524, 1.535, and 1.563 for DINP, DEHP, and DBP, respectively. In this experiment different concentrations of DBP were investigated using THz-TDS. Changes were measured in the low THz frequency range for refractive indices and characteristic absorption. The results indicated that THz-TDS is promising as a new method in determining PAEs in many materials. The results of this study could be used to support the practical application of THz-TDS in quality detection and food monitoring. In particular, this new technique could be used in detecting hazardous materials and other substances present in wine or foods.

Health risk assessment of phthalate esters (PAEs) in drinking water sources of China.

PubMed

Wang, Wen-Long; Wu, Qian-Yuan; Wang, Chao; He, Tao; Hu, Hong-Ying

2015-03-01

Phthalate esters (PAEs) with endocrine disruption effects and carcinogenicity are widely detected in water environment. Occurrences of PAEs in source water and removal efficiencies of PAEs by drinking water treatment plants (DWTPs) in China were surveyed from publications in the last 10 years. Concentration of diethylhexyl phthalate (DEHP) in source water with median value of 1.3 μg/L was higher than that of dimethyl phthalate (DMP), diethyl phthalate (DEP), and di-n-butyl phthalate (DnBP). If the removal efficiencies of DEHP and DnBP reached 60 and 90 %, respectively, the calculated PAE concentration in drinking water can generally meet Standards for Drinking Water Quality in China. The health risks of PAEs, including non-carcinogenic and carcinogenic risks via the "water source-DWTP-oral ingestion/dermal permeation" pathway, were evaluated with Monte Carlo simulation and sensitivity analysis under certain removal efficiencies from 0 to 95 %. The carcinogenic risk of DEHP was lower than the upper acceptable carcinogenic risk level (10(-4)), while the probability of DEHP's carcinogenic risk between lower (10(-6)) and upper (10(-4)) acceptable carcinogenic risk level decreased from about 21.2 to 0.4 % through increasing DEHP removal efficiency from 0 to 95 %. The non-carcinogenic risk of DEHP was higher than that of DEP and DnBP. In all cases, the total non-carcinogenic risk of DEP, DnBP, and DEHP was lower than 1, indicating that there would be unlikely incremental non-carcinogenic risk to humans. Both carcinogenic risk and non-carcinogenic risk of PAEs in drinking water to female were a little higher than those to male.

Cumulative Effects of In Utero Administration of Mixtures of Reproductive Toxicants that Disrupt Common Target Tissues via Diverse Mechanisms of Toxicity

PubMed Central

Rider, Cynthia V.; Furr, Johnathan R.; Wilson, Vickie S.; Gray, L. Earl

2010-01-01

Although risk assessments are typically conducted on a chemical-by-chemical basis, the 1996 Food Quality Protection Act required the US Environmental Protection Agency to consider cumulative risk of chemicals that act via a common mechanism of toxicity. To this end, we are conducting studies with mixtures of chemicals to elucidate mechanisms of joint action at the systemic level with the end goal of providing a framework for assessing the cumulative effects of reproductive toxicants. Previous mixture studies conducted with antiandrogenic chemicals are reviewed briefly and two new studies are described in detail. In all binary mixture studies, rats were dosed during pregnancy with chemicals, singly or in pairs at dosage levels equivalent to approximately one half of the ED50 for hypospadias or epididymal agenesis. The binary mixtures included: androgen receptor (AR) antagonists (vinclozolin plus procymidone), phthalate esters (DBP plus BBP and DEHP plus DBP), a phthalate ester plus an AR antagonist (DBP plus procymidone), a mixed mechanism androgen signaling disruptor (linuron) plus BBP, and two chemicals which disrupt epididymal differentiation through entirely different toxicity pathways: DBP (AR pathway) plus 2,3,7,8 TCDD (AhR pathway). We also conducted multi-component mixture studies combining several “antiandrogens” together. In the first study, seven chemicals (four pesticides and three phthalates) that elicit antiandrogenic effects at two different sites in the androgen signaling pathway (i.e. AR antagonist or inhibition of androgen synthesis) were combined. In the second study, three additional phthalates were added to make a ten chemical mixture. In both the binary mixture studies and the multi-component mixture studies, chemicals that targeted male reproductive tract development displayed cumulative effects that exceeded predictions based upon a response addition model and most often were in accordance with predictions based upon dose addition models. In summary, our results indicate that compounds that act by disparate mechanisms of toxicity to disrupt the dynamic interactions among the interconnected signaling pathways in differentiating tissues produce cumulative dose-additive effects, regardless of the mechanism or mode of action of the individual mixture component. PMID:20487044

Various causes behind the desorption hysteresis of carboxylic acids on mudstones.

PubMed

Rasamimanana, S; Lefèvre, G; Dagnelie, R V H

2017-02-01

Adsorption desorption is a key factor for leaching, migration and (bio)degradation of organic pollutants in soils and sediments. Desorption hysteresis of apolar organic compounds is known to be correlated with adsorption/diffusion into soil organic matter. This work focuses on the desorption hysteresis of polar organic compounds on a natural mudstone sample. Acetic, citric and ortho-phthalic acids displayed adsorption-desorption hysteresis on Callovo-Oxfordian mudstone. The non-reversible behaviours resulted from three different mechanisms. Adsorption and desorption kinetics were evaluated using 14C- and 3H-labelled tracers and an isotopic exchange method. The solid-liquid distribution ratio of acetate decreased using a NaN 3 bactericide, indicating a rapid bacterial consumption compared with negligible adsorption. The desorption hysteresis of phthalate was apparent and suppressed by the equilibration of renewal pore water with mudstone. This confirms the significant and reversible adsorption of phthalate. Finally, persistent desorption hysteresis was evidenced for citrate. In this case, a third mechanism should be considered, such as the incorporation of citrate in the solid or a chemical perturbation, leading to strong desorption resilience. The results highlighted the different pathways that polar organic pollutants might encounter in a similar environment. Data on phthalic acid is useful to predict the retarded transport of phthalate esters and amines degradation products in sediments. The behaviour of citric acid is representative of polydentate chelating agents used in ore and remediation industries. The impact of irreversible adsorption on solid/solution partitioning and transport deserves further investigation. Copyright © 2016 Elsevier Ltd. All rights reserved.

Determination of vapor pressures for nonpolar and semipolar organic compounds from gas chromatographic retention data

USGS Publications Warehouse

Hinckley, D.A.; Bidleman, T.F.; Foreman, W.T.; Tuschall, J.R.

1990-01-01

Vapor pressures for nonpolar and moderately polar organochlorine, pyrethroid, and organophosphate insecticides, phthalate esters, and organophosphate flame retardants were determined by capillary gas chromatography (GC). Organochlorines and polycyclic aromatic hydrocarbons with known liquid-phase vapor pressures (P??L) (standard compounds) were chromatographed along with two reference compounds n-C20 (elcosane) and p,p???-DDT on a 1.0-m-long poly(dimethylsiloxane) bonded-phase (BP-1) column to determine their vapor pressures by GC (P??GC). A plot of log P??L vs log P??GC for standard compounds was made to establish a correlation between measured and literature values, and this correlation was then used to compute P??L of test compounds from their measured P??GC. P??L of seven major components of technical chlordane, endosulfan and its metabolites, ??-hexachlorocyclohexane, mirex, and two components of technical toxaphene were determined by GC. This method provides vapor pressures within a factor of 2 of average literature values for nonpolar compounds, similar to reported interlaboratory precisions of vapor pressure determinations. GC tends to overestimate vapor pressures of moderately polar compounds. ?? 1990 American Chemical Society.

Phthalate esters in soil, plastic film, and vegetable from greenhouse vegetable production bases in Beijing, China: Concentrations, sources, and risk assessment.

PubMed

Li, Cheng; Chen, Jiayi; Wang, Jihua; Han, Ping; Luan, Yunxia; Ma, Xupu; Lu, Anxiang

2016-10-15

The increased use of plastic film in greenhouse vegetable production (GVP) could result in phthalate ester (PAE) contamination in vegetables. However, limited information is currently available on their occurrence and associated potential risks in GVP systems. The present study documents the occurrence and composition of 15 PAEs in soil, plastic film, and vegetable samples from eight large-scale GVP bases in Beijing, China. Results showed that PAEs are ubiquitous contaminants in these GVP bases. Total PAE concentrations ranged from 0.14 to 2.13mg/kg (mean 0.99mg/kg) in soils and from 0.15 to 6.94mg/kg (mean 1.49mg/kg) in vegetables. Di (2-ethylhexyl) phthalate, di-n-butyl phthalate, and diisobutyl phthalate were the most abundant components, which accounted for >90% of the total PAEs. This investigation also indicated that the widespread application of plastic film in GVP systems may be the primary source of these PAEs. The non-cancer and carcinogenic risks of target PAEs were estimated based on the exposures of vegetable intake. The hazard quotients of PAE in all vegetable samples were lower than 1 and the carcinogenic risks were also at acceptable levels for consumers. The data in this study can provide valuable information to understand the status of potential pollutants, specifically PAEs, in GVP systems. Copyright © 2016 Elsevier B.V. All rights reserved.

Contamination of Phthalate Esters (PAEs) in Typical Wastewater-Irrigated Agricultural Soils in Hebei, North China.

PubMed

Zhang, Yuan; Liang, Qiong; Gao, Rutai; Hou, Haobo; Tan, Wenbing; He, Xiaosong; Zhang, Hui; Yu, Minda; Ma, Lina; Xi, Beidou; Wang, Xiaowei

2015-01-01

The Wangyang River (WYR) basin is a typical wastewater irrigation area in Hebei Province, North China. This study investigated the concentration and distribution of six priority phthalate esters (PAEs) in the agricultural soils in this area. Thirty-nine soil samples (0-20 cm) were collected along the WYR to assess the PAE residues in soils. Results showed that PAEs are ubiquitous environmental contaminants in the topsoil obtained from the irrigation area. The concentrations of Σ6PAEs range from 0.191 μg g-1 dw to 0.457 μg g-1 dw with an average value of 0.294 μg g-1 dw. Di(2-ethylhexyl) phthalate (DEHP) and di-n-butyl phthalate (DnBP) are the dominant PAE species in the agricultural soils. Among the DEHP concentrations, the highest DEHP concentration was found at the sites close to the villages; this result suggested that dense anthropogenic activities and random garbage disposal in the rural area are possible sources of PAEs. The PAE concentrations were weakly and positively correlated with soil organic carbon and soil enzyme activities; thus, these factors can affect the distribution of PAEs. This study further showed that only dimethyl phthalate (DMP) concentrations exceeded the recommended allowable concentrations; no remediation measures are necessary to control the PAEs in the WYR area. However, the PAEs in the topsoil may pose a potential risk to the ecosystem and human health in this area. Therefore, the exacerbating PAE pollution should be addressed.

Contamination of Phthalate Esters (PAEs) in Typical Wastewater-Irrigated Agricultural Soils in Hebei, North China

PubMed Central

Zhang, Yuan; Liang, Qiong; Gao, Rutai; Hou, Haobo; Tan, Wenbing; He, Xiaosong; Zhang, Hui; Yu, Minda; Ma, Lina; Xi, Beidou; Wang, Xiaowei

2015-01-01

The Wangyang River (WYR) basin is a typical wastewater irrigation area in Hebei Province, North China. This study investigated the concentration and distribution of six priority phthalate esters (PAEs) in the agricultural soils in this area. Thirty-nine soil samples (0–20 cm) were collected along the WYR to assess the PAE residues in soils. Results showed that PAEs are ubiquitous environmental contaminants in the topsoil obtained from the irrigation area. The concentrations of Σ6PAEs range from 0.191 μg g−1 dw to 0.457 μg g−1 dw with an average value of 0.294 μg g−1 dw. Di(2-ethylhexyl) phthalate (DEHP) and di-n-butyl phthalate (DnBP) are the dominant PAE species in the agricultural soils. Among the DEHP concentrations, the highest DEHP concentration was found at the sites close to the villages; this result suggested that dense anthropogenic activities and random garbage disposal in the rural area are possible sources of PAEs. The PAE concentrations were weakly and positively correlated with soil organic carbon and soil enzyme activities; thus, these factors can affect the distribution of PAEs. This study further showed that only dimethyl phthalate (DMP) concentrations exceeded the recommended allowable concentrations; no remediation measures are necessary to control the PAEs in the WYR area. However, the PAEs in the topsoil may pose a potential risk to the ecosystem and human health in this area. Therefore, the exacerbating PAE pollution should be addressed. PMID:26360905

Endocrine disruption: In silico interactions between phthalate plasticizers and corticosteroid binding globulin.

PubMed

Sheikh, Ishfaq A; Beg, Mohd A

2017-12-01

Endocrine disruption is a phenomenon when a man-made or natural compound interferes with normal hormone function in human or animal body systems. Endocrine-disrupting compounds (EDCs) have assumed considerable importance as a result of industrial activity, mass production of synthetic chemicals and environmental pollution. Phthalate plasticizers are a group of chemicals used widely and diversely in industry especially in the plastic industry, and many of the phthalate compounds have endocrine-disrupting properties. Increasing evidence indicates that steroid nuclear receptors and steroid binding proteins are the main targets of endocrine disruption. Corticosteroid-binding globulin (CBG) is a steroid binding protein that binds and transports cortisol in the blood circulation and is a potential target for endocrine disruption. An imbalance of cortisol in the body leads to many health problems. Induced fit docking of nine important and environmentally relevant phthalate plasticizers (DMP, BBP, DBP, DIBP, DnHP, DEHP, DINP, DnOP, DIDP) showed interactions with 10-19 amino acid residues of CBG. Comparison of the interacting residues of CBG with phthalate ligands and cortisol showed an overlapping of the majority (53-82%) of residues for each phthalate. Five of nine phthalate compounds and cortisol shared a hydrogen bonding interaction with the Arg-252 residue of CBG. Long-chain phthalates, such as DEHP, DINP, DnOP and DIDP displayed a higher binding affinity and formed a number of interactions with CBG in comparison to short-chain phthalates. The similarity in structural binding characteristics of phthalate compounds and native ligand cortisol suggested potential competitive conflicts in CBG-cortisol binding function and possible disruption of cortisol and progesterone homeostasis. Copyright © 2017 John Wiley & Sons, Ltd.

The influence of facility agriculture production on phthalate esters distribution in black soils of northeast China.

PubMed

Zhang, Ying; Wang, Pengjie; Wang, Lei; Sun, Guoqiang; Zhao, Jiaying; Zhang, Hui; Du, Na

2015-02-15

The current study investigates the existence of 15 phthalate esters (PAEs) in surface soils (27 samples) collected from 9 different facility agriculture sites in the black soil region of northeast China, during the process of agricultural production (comprising only three seasons spring, summer and autumn). Concentrations of the 15 PAEs detected significantly varied from spring to autumn and their values ranged from 1.37 to 4.90 mg/kg-dw, with a median value of 2.83 mg/kg-dw. The highest concentration of the 15 PAEs (4.90 mg/kg-dw) was determined in summer when mulching film was used in the greenhouses. Probably an increase in environmental temperature was a major reason for PAE transfer from the mulching film into the soil and coupled with the increased usage of chemical fertilizers in greenhouses. Results showed that of the 15 PAEs, di(2-ethylhexyl) phthalate(DEHP), di-n-butyl phthalate (DBP), diethyl phthalate (DEP) and dimethyl phthalate (DMP) were in abundance with the mean value of 1.12 ± 0.22, 0.46 ± 0.05, 0.36 ± 0.04, and 0.17 ± 0.01 mg/kg-dw, respectively; and their average contributions in spring, summer, and autumn ranged between 64.08 and 90.51% among the 15 PAEs. The results of Principal Component Analysis (PCA) indicated the concentration of these four main PAEs significantly differed among the facility agricultures investigated, during the process of agricultural production. In comparison with foreign and domestic results of previous researches, it is proved that the black soils of facility agriculture in northeast China show higher pollution situation comparing with non-facility agriculture soils. Copyright © 2014 Elsevier B.V. All rights reserved.

Phthalate esters and childhood asthma: A systematic review and congener-specific meta-analysis.

PubMed

Li, Ming-Chieh; Chen, Chi-Hsien; Guo, Yue Leon

2017-10-01

Exposure to phthalate esters (PAEs) has been associated with childhood asthma, but the congener-specific effects of PAEs on childhood asthma were unclear. We aimed to systematically review and meta-analyze observational studies on the associations between specific effects of PAEs and the risk of childhood asthma. Relevant studies were identified by searching three databases up to October 20, 2016. The reference lists of the retrieved articles were also reviewed. We included observational studies that reported risk estimates with 95% confidence intervals (CIs) for the associations between phthalate exposure and the risk of childhood asthma. Fixed-effects models were generally applied to calculate pooled risk estimates. When heterogeneity was present, random-effects models were applied. A total of nine studies featuring 43 data points were included in our final meta-analyses. Results indicated that the benzyl butyl phthalate (BBzP) exposure had a significant association with the risk of childhood asthma. The Odd Ratios (ORs) were from 1.39 to 1.41 for different combination strategies. Subgroup analyses by different exposure period or samples used showed that prenatal exposure to BBzP had a stronger association with the risk of childhood asthma (OR = 1.38, 95% CI = 1.09-1.75), compared to those with postnatal exposure. Besides, the association was evident when the phthalate exposure was measured from dust samples. The OR for the associations between di-2-ethylhexyl phthalate (DEHP) in dust and childhood asthma was 2.71 (95% CI = 1.39-5.28), and 2.08 (95% CI = 1.10-3.92) for BBzP. Our study suggested a positive association between DEHP and BBzP exposure and childhood asthma. Future studies are warranted to identify the underlying mechanisms of the association. Copyright © 2017 Elsevier Ltd. All rights reserved.

Occurrence and Removal Characteristics of Phthalate Esters from Typical Water Sources in Northeast China

PubMed Central

Liu, Yu; Chen, Zhonglin; Shen, Jimin

2013-01-01

The presence of phthalate esters (PAEs) in the environment has gained a considerable attention due to their potential impacts on public health. This study reports the first data on the occurrence of 15 PAEs in the water near the Mopanshan Reservoir—the new and important water source of Harbin city in Northeast China. As drinking water is a major source for human exposure to PAEs, the fate of target PAEs in the two waterworks (Mopanshan Waterworks and Seven Waterworks) was also analyzed. The results demonstrated that the total concentrations of 15 PAEs in the water near the Mopanshan Reservoir were relatively moderate, ranging from 355.8 to 9226.5 ng/L, with the mean value of 2943.1 ng/L. DBP and DEHP dominated the PAE concentrations, which ranged from 52.5 to 4498.2 ng/L and 128.9 to 6570.9 ng/L, respectively. The occurrence and concentrations of these compounds were heavily spatially dependent. Meanwhile, the results on the waterworks samples suggested no significant differences in PAE levels with the input of the raw waters. Without effective and stable removal of PAEs after the conventional drinking water treatment in the waterworks (25.8% to 76.5%), the risks posed by PAEs through drinking water ingestion were still existing, which should be paid special attention to the source control in the Mopanshan Reservoir and some advanced treatment processes for drinking water supplies. PMID:23577281

Magnetic solid-phase extraction of phthalate esters (PAEs) in apparel textile by core-shell structured Fe3O4@silica@triblock-copolymer magnetic microspheres.

PubMed

Xu, Mei; Liu, Minhua; Sun, Meirong; Chen, Kun; Cao, Xiujun; Hu, Yaoming

2016-04-01

In this paper, novel core-shell structured magnetic Fe3O4/silica nanocomposites with triblock-copolymer grafted on their surface (Fe3O4@SiO2@MDN) were successfully fabricated by combining a sol-gel method with a seeded aqueous-phase radical copolymerization approach. Owing to the excellent characteristics of the strong magnetic responsivity, outstanding hydrophilicity and abundant π-electron system, the obtained core-shell structured microspheres showed great potential as a magnetic solid phase extraction (MSPE) adsorbent. Several kinds of phthalate esters (PAEs) were selected as model analytes to systematically evaluate the applicability of adsorbents for extraction followed by gas chromatography-mass spectrometry (GC-MS) analyses. Various parameters, including adsorbents amounts, adsorption time, species of eluent, and desorption time were optimized. Under the optimized conditions, Validation experiments such as recovery, reproducibility, and limit of detection were carried on and showed satisfactory results. The analysis method showed excellent linearity with a wide range of 0.2-10mg/kg (R(2)>0.9974) and low limits of detection (LOD) of 0.02-0.09 mg/kg (S/N=3). Ultimately, the novel magnetic adsorbents were successfully employed to detect the PAEs in apparel textile samples. And the results indicated that this novel approach brought forward in the present work offered an attractive alternative for rapid, efficient and sensitive MSPE for PAEs compounds. Copyright © 2015 Elsevier B.V. All rights reserved.

The classic EDCs, phthalate esters and organochlorines, in relation to abnormal sperm quality: a systematic review with meta-analysis.

PubMed

Wang, Chao; Yang, Lu; Wang, Shu; Zhang, Zhan; Yu, Yongquan; Wang, Meilin; Cromie, Meghan; Gao, Weimin; Wang, Shou-Lin

2016-01-25

The association between endocrine disrupting chemicals (EDCs) and human sperm quality is controversial due to the inconsistent literature findings, therefore, a systematic review with meta-analysis was performed. Through the literature search and selection based on inclusion criteria, a total of 9 studies (7 cross-sectional, 1 case-control, and 1 pilot study) were analyzed for classic EDCs (5 studies for phthalate esters and 4 studies for organochlorines). Funnel plots revealed a symmetrical distribution with no evidence of publication bias (Begg's test: intercept = 0.40; p = 0.692). The summary odds ratios (OR) of human sperm quality associated with the classic EDCs was 1.67 (95% CI: 1.31-2.02). After stratification by specific chemical class, consistent increases in the risk of abnormal sperm quality were found in phthalate ester group (OR = 1.52; 95% CI: 1.09-1.95) and organochlorine group (OR = 1.98; 95% CI: 1.34-2.62). Additionally, identification of official data, and a comprehensive review of the mechanisms were performed, and better elucidated the increased risk of these classic EDCs on abnormal sperm quality. The present systematic review and meta-analysis helps to identify the impact of classic EDCs on human sperm quality. However, it still highlights the need for additional epidemiological studies in a larger variety of geographic locations.

The classic EDCs, phthalate esters and organochlorines, in relation to abnormal sperm quality: a systematic review with meta-analysis

NASA Astrophysics Data System (ADS)

Wang, Chao; Yang, Lu; Wang, Shu; Zhang, Zhan; Yu, Yongquan; Wang, Meilin; Cromie, Meghan; Gao, Weimin; Wang, Shou-Lin

2016-01-01

The association between endocrine disrupting chemicals (EDCs) and human sperm quality is controversial due to the inconsistent literature findings, therefore, a systematic review with meta-analysis was performed. Through the literature search and selection based on inclusion criteria, a total of 9 studies (7 cross-sectional, 1 case-control, and 1 pilot study) were analyzed for classic EDCs (5 studies for phthalate esters and 4 studies for organochlorines). Funnel plots revealed a symmetrical distribution with no evidence of publication bias (Begg’s test: intercept = 0.40 p = 0.692). The summary odds ratios (OR) of human sperm quality associated with the classic EDCs was 1.67 (95% CI: 1.31-2.02). After stratification by specific chemical class, consistent increases in the risk of abnormal sperm quality were found in phthalate ester group (OR = 1.52 95% CI: 1.09-1.95) and organochlorine group (OR = 1.98 95% CI: 1.34-2.62). Additionally, identification of official data, and a comprehensive review of the mechanisms were performed, and better elucidated the increased risk of these classic EDCs on abnormal sperm quality. The present systematic review and meta-analysis helps to identify the impact of classic EDCs on human sperm quality. However, it still highlights the need for additional epidemiological studies in a larger variety of geographic locations.

Analysis of phthalate esters in soils near an electronics manufacturing facility and from a non-industrialized area by gas purge microsyringe extraction and gas chromatography.

PubMed

Wu, Wei; Hu, Jia; Wang, Jinqi; Chen, Xuerong; Yao, Na; Tao, Jing; Zhou, Yi-Kai

2015-03-01

Here, a novel technique is described for the extraction and quantitative determination of six phthalate esters (PAEs) from soils by gas purge microsyringe extraction and gas chromatography. Recovery of PAEs ranged from 81.4% to 120.3%, and the relative standard deviation (n=6) ranged from 5.3% to 10.5%. Soil samples were collected from roadsides, farmlands, residential areas, and non-cultivated areas in a non-industrialized region, and from the same land-use types within 1 km of an electronics manufacturing facility (n=142). Total PAEs varied from 2.21 to 157.62 mg kg(-1) in non-industrialized areas and from 8.63 to 171.64 mg kg(-1) in the electronics manufacturing area. PAE concentrations in the non-industrialized area were highest in farmland, followed (in decreasing order) by roadsides, residential areas, and non-cultivated soil. In the electronics manufacturing area, PAE concentrations were highest in roadside soils, followed by residential areas, farmland, and non-cultivated soils. Concentrations of dimethyl phthalate (DMP), diethyl phthalate (DEP), and di-n-butyl phthalate (DnBP) differed significantly (P<0.01) between the industrial and non-industrialized areas. Principal component analysis indicated that the strongest explanatory factor was related to DMP and DnBP in non-industrialized soils and to butyl benzyl phthalate (BBP) and DMP in soils near the electronics manufacturing facility. Congener-specific analysis confirmed that diethylhexyl phthalate (DEHP) was a predictive indication both in the non-industrialized area (r(2)=0.944, P<0.01) and the industrialized area (r(2)=0.860, P<0.01). The higher PAE contents in soils near the electronics manufacturing facility are of concern, considering the large quantities of electronic wastes generated with ongoing industrialization. Copyright © 2014 Elsevier B.V. All rights reserved.

Equilibrium and heat of adsorption of diethyl phthalate on heterogeneous adsorbents.

PubMed

Zhang, Weiming; Xu, Zhengwen; Pan, Bingcai; Hong, Changhong; Jia, Kun; Jiang, Peijuan; Zhang, Qingjian; Pan, Bingjun

2008-09-01

Removal of phthalate esters from water has been of considerable concern recently. In the present study, the adsorptive removal performance of diethyl phthalate (DEP) from water was investigated with the aminated polystyrene resin (NDA-101) and oxidized polystyrene resin (NDA-702). In addition, the commercial homogeneous polystyrene resin (XAD-4) and acrylic ester resin (Amberlite XAD-7) as well as coal-based granular activated carbon (AC-750) were chosen for comparison. The corresponding equilibrium isotherms are well described by the Freundlich equation and the adsorption capacities for DEP followed the order NDA-702 > NDA-101 > AC-750 > XAD-4 > XAD-7. Analysis of adsorption mechanisms suggested that these adsorbents spontaneously adsorb DEP molecules driven mainly by enthalpy change, and the adsorption process was derived by multiple adsorbent-adsorbate interactions such as hydrogen bonding, pi-pi stacking, and micropore filling. The information related to the adsorbent surface heterogeneity and the adsorbate-adsorbate interaction was obtained by Do's model. All the results indicate that heterogeneous resins NDA-702 and NDA-101 have excellent potential as an adsorption material for the removal of DEP from the contaminated water.

Semivolatile organic compounds in residential air along the Arizona - Mexico border

USGS Publications Warehouse

Gale, R.W.; Cranor, W.L.; Alvarez, D.A.; Huckins, J.N.; Petty, J.D.; Robertson, G.L.

2009-01-01

Concerns about indoor air quality and the potential effects on people living in these environments are increasing as more reports about the toxicities and the potential indoor air exposure levels of household-use chemicals and chemicals fromhousingandfurnishingmanufactureinairarebeingassessed. Gas chromatography/mass spectrometry was used to confirm numerous airborne contaminants obtained from the analysis of semipermeable membrane devices deployed inside of 52 homes situated along the border between Arizona and Mexico. We also describe nontarget analytes in the organochlorine pesticide fractions of 12 of these homes; this fraction is also the most likelytocontainthebroadestscopeofbioconcentratablechemicals accumulated from the indoor air. Approximately 400 individual components were identified, ranging from pesticides to a wide array of hydrocarbons, fragrances such as the musk xylenes, flavors relating to spices, aldehydes, alcohols, esters and phthalate esters, and other miscellaneous types of chemicals. The results presented in this study demonstrate unequivocally that the mixture of airborne chemicals present indoors is far more complex than previously demonstrated. ?? 2009 American Chemical Society.

Biodegradation of phthalic acid esters (PAEs) and in silico structural characterization of mono-2-ethylhexyl phthalate (MEHP) hydrolase on the basis of close structural homolog.

PubMed

Singh, Neha; Dalal, Vikram; Mahto, Jai Krishna; Kumar, Pravindra

2017-09-15

Three bacterial strains capable of degrading phthalates namely Pseudomonas sp. PKDM2, Pseudomonas sp. PKDE1 and Pseudomonas sp. PKDE2 were isolated and characterized for their degradative potential. These strains efficiently degraded 77.4%-84.4% of DMP, 75.0%-75.7% of DEP and 71.7%-74.7% of DEHP, initial amount of each phthalate is 500mgL -1 of each phthalate, after 44h of incubation. GC-MS results reveal the tentative DEHP degradation pathway, where hydrolases mediate the breakdown of DEHP to phthalic acid (PA) via an intermediate MEHP. MEHP hydrolase is a serine hydrolase which is involved in the reduction of the MEHP to PA. The predicted 3D model of MEHP hydrolase from Pseudomonas mosselii was docked with phthalate monoesters (PMEs) such as MEHP, mono-n-hexyl phthalate (MHP), mono-n-butyl phthalate (MBP) and mono-n-ethyl phthalate (MEP), respectively. Docking results show the distance between the carbonyl carbon of respective phthalate monoester and the hydroxyl group of catalytic serine lies in the range of 2.9 to 3.3Å, which is similar to the ES complex of other serine hydrolases. This structural study highlights the interaction and the role of catalytic residues of MEHP hydrolase involved in the biodegradation of PMEs to phthalate. Copyright © 2017 Elsevier B.V. All rights reserved.

Atmospheric deposition of phthalate esters in a subtropical city

NASA Astrophysics Data System (ADS)

Zeng, Feng; Lin, Yujun; Cui, Kunyan; Wen, Jiaxin; Ma, Yongqin; Chen, Hongli; Zhu, Fang; Ma, Zhiling; Zeng, Zunxiang

2010-02-01

In Chinese cities, air pollution has become a serious and aggravating environmental problem undermining the sustainability of urban ecosystems and the quality of urban life. Bulk atmospheric deposition samples were collected two-weekly, from February 2007 to January 2008, at three representative areas, one suburban and two urbanized, in the subtropical city, Guangzhou, China, to assess the deposition fluxes and seasonal variations of phthalate esters (PAEs). Sixteen PAE congeners in bulk deposition samples were measured and the depositional fluxes of ∑ 16PAEs ranged from 3.41 to 190 μg m -2 day -1, and were highly affected by local anthropogenic activities. The significant relationship between PAEs and particulate depositional fluxes (correlation coefficient R2 = 0.72, P < 0.001) showed PAEs are associated primarily with particles. Temporal flux variations of PAEs were influenced by seasonal changes in meteorological parameters, and the deposition fluxes of PAEs were obviously higher in wet season than in dry season. Diisobutyl phthalate (D iBP), Di- n-butyl phthalate (D nBP), and Di(2-ethylhexyl) phthalate (DEHP) dominated the PAE pattern in bulk depositions, which is consistent with a high consumption of the plasticizer market in China. PAE profiles in bulk deposition showed similarities exhibited in both time and space, and a weak increase of high molecular weight PAE (HMW PAE) contribution in the wet season compared to those in the dry season. Average atmospheric deposition fluxes of PAEs in the present study were significantly higher than those from other studies, reflecting strong anthropogenic inputs as a consequence of rapid industrial and urban development in the region.

Role of Oxidative Stress in Male Reproductive Dysfunctions with Reference to Phthalate Compounds.

PubMed

Sedha, Sapna; Kumar, Sunil; Shukla, Shruti

2015-11-14

A wide variety of environmental chemicals/xenobiotics including phthalates have been shown to cause oxidative stress targeting the endocrine system and cause reproductive anomalies. The present review describes various issues by oxidative stress causing male reproductive dysfunctions. Here in this review, the importance and role of phthalate compounds in male reproductive dysfunction has been well documented. One class of environmental endocrine disruptors is phthalates. Phthalate compounds are mostly used as plasticizers, which increase the flexibility, durability, longevity, and etc. of the plastics. Large-scale use of plastic products in our daily life as well as thousands of workers engaged in the manufacture of plastic and plastic products and recycling plastic industry are potentially exposed to these chemicals. Further, general population as well as vulnerable groups i.e. children and pregnant women are also exposed to these chemicals. Phthalates are among wide variety of environmental toxicants capable of compromising male fertility by inducing a state of oxidative stress in the testes. They may also generate reactive oxygen species (ROS) that may affect various physiological and reproductive functions. The available data points out that phthalate compounds may also induce oxidative stress in the male reproductive organs mainly testis and epididymis. They impair spermatogenic process by inducing oxidative stress and apoptosis in germ cells or target sertoli cells and thereby hamper spermatogenesis. They also impair the Leydig cell function by inducing ROS, thereby decreasing the levels of steroidogenic enzymes. Thus in utero and postnatal exposure to phthalate compounds might lead to decreased sperm count and various other reproductive anomalies in the young male.

Cummulative effects of a 9 phthalate mixture using DEHP, DiHP, DiBP, DBP, BBP, DCHP, D(hexyl)P,D(heptyl)P and DPeP on Charles River-Sprague Dawley (CR-SD) fetal rat testis testosterone(T) production and gene expression

EPA Science Inventory

In utero exposure to mixtures of 2 to 5 phthalate esters (PE) with similar modes of action have been shown to inhibit male reproductive development in a dose-additive fashion. Further when PE were administered to pregnant dams during the period of sexual differentiation, when rep...

Gas Chromatographic Determination of Enrivonmentally Significant Pesticides.

ERIC Educational Resources Information Center

Rudzinski, Walter E.; Beu, Steve

1982-01-01

A chromatographic procedure for analyzing organophosphorus pesticides (such as PCB's, nitrosamines, and phthalate esters) in orange juice is described, including a summary of the method, instrumentation, methodology, results/discussion, and calculations. (JN)

Pesticide and plasticizer residues in bergamot essential oils from Calabria (Italy).

PubMed

Di Bella, Giuseppa; Saitta, Marcello; La Pera, Lara; Alfa, Maria; Dugo, Giacomo

2004-08-01

Organophosphorus and organochlorine pesticides, phosphorated plasticizers, chloroparaffins and phthalate esters contamination in bergamot essential oils produced in Calabria in the crop years 1999-2000 was studied by HRGC in connection with detectors FPD, ECD, MS. Residues of dicofol and tetradifon were found in oils from both crop years. The mean dicofol concentration was 0.26 mg/l in samples from 1999 and 0.20 mg/l in those from 2000; the mean tetradifon content was 0.06 mg/l for both the crop years. Among plasticizers, residues of diisobutyl phthalate, di-n-butyl phthalate, and bis(2-ethylhexyl) phthalate were found in samples from crop years 1999 and 2000, the mean content were 1.22 and 1.23 mg/l, 1.51 and 1.65 mg/l, 1.38 and 1.42 mg/l respectively.

Cytochrome P450-inhibitory activity of parabens and phthalates used in consumer products.

PubMed

Ozaki, Hitomi; Sugihara, Kazumi; Watanabe, Yoko; Ohta, Shigeru; Kitamura, Shigeyuki

2016-01-01

The in vitro cytochrome P450 (CYP)-inhibitory effects of 11 parabens and 7 phthalates used in consumer products, as well as their hydrolytic metabolites, were investigated, using rat liver microsomes as an enzyme source. The effects on individual CYP isozymes were evaluated by assaying inhibition of activities towards specific substrates, i.e., ethoxyresorufin O-dealkylase (EROD), methoxyresorufin O-dealkylase (MROD), pentoxyresorufin O-dealkylase (PROD), 7-benzyloxy-4-trifluoromethylcoumarin dealkylase (BFCD), 7-methoxy-4-trifluoromethylcoumarin dealkylase (MFCD) and 7-ethoxy-4-trifluoromethylcoumarin dealkylase (EFCD) activities. These activities were dose-dependently inhibited, most potently by medium-side-chain parabens (C6-9) and phthalates (C4-6), and less potently by shorter- and longer-side-chain esters. The hydrolytic product of parabens, 4-hydroxybenzoic acid, was not inhibitory, while those of phthalates, phthalic acid monoesters, showed lower inhibitory activity than the parent phthalates. Parabens showed relatively potent inhibition of MFCD activity, considered to be mainly due to CYP2C, and phthalates showed relatively potent inhibition of PROD activity, considered to be mainly due to CYP2B.

The identification of trends in outgassing technology

NASA Technical Reports Server (NTRS)

Colony, J. A.

1980-01-01

A large amount of chemical analysis data involving identification of outgassing products from spacecraft, experiment modules, and support equipment accumulated at the Goddard Space Flight Center over the past ten years were reduced to a computer compatible format and subjected to a variety of relevant program operations. From these data a list of the most troublesome outgassing species were compiled and several useful and interesting materials' correlations were developed. The frequency of occurrence totals show that in aerospace program, di(2-ethyl hexyl) phthalate (DEHP) is the most often found individual species in outgassing samples and that esters are the leading generic class of compounds. The effectiveness of this data bank was demonstrated by the good correlations between materials and their outgassing products for solar panel bakeouts and cable bakeouts. However, trends in frequency of occurrence of many compounds were demonstrated where no correlation could be established. In the case of the class of compounds called aliphatic hydrocarbons, it is shown that the number of instances of significant outgassing due to these materials is increasing.

Effect of cooking at home on the levels of eight phthalates in foods.

PubMed

Fierens, T; Vanermen, G; Van Holderbeke, M; De Henauw, S; Sioen, I

2012-12-01

Food products can be contaminated with toxic compounds via the environment. Another possibility of food contamination is that toxicants are generated in foods or that chemicals migrate from food contact materials into foods during processing. In this study, the effect of cooking at home on the levels of phthalates - world's most used group of plasticisers - in various food types (starchy products, vegetables and meat and fish) was examined. Eight compounds were considered, namely dimethyl phthalate (DMP), diethyl phthalate (DEP), diisobutyl phthalate (DiBP), di-n-butyl phthalate (DnBP), benzylbutyl phthalate (BBP), di(2-ethylhexyl) phthalate (DEHP), dicyclohexyl phthalate (DCHP) and di-n-octyl phthalate (DnOP). Food products were analysed before as well as after cooking (boiling, steaming, (deep-)frying or grilling). In general, phthalate concentrations in foods declined after cooking, except in vegetables, where almost no effect was seen. Several factors influenced the degree of this decline (e.g. weight difference, fat uptake, etc.). Of all phthalates, DEHP, DiBP and BBP were affected the most. In conclusion, cooking at home definitely affected phthalate concentrations in foods and thus needs to be considered in order to correctly assess humans' dietary exposure to these contaminants. Copyright © 2012 Elsevier Ltd. All rights reserved.

Biosynthesis of mercapturic acids from allyl alcohol, allyl esters and acrolein

PubMed Central

Kaye, Clive M.

1973-01-01

1. 3-Hydroxypropylmercapturic acid, i.e. N-acetyl-S-(3-hydroxypropyl)-l-cysteine, was isolated, as its dicyclohexylammonium salt, from the urine of rats after the subcutaneous injection of each of the following compounds: allyl alcohol, allyl formate, allyl propionate, allyl nitrate, acrolein and S-(3-hydroxypropyl)-l-cysteine. 2. Allylmercapturic acid, i.e. N-acetyl-S-allyl-l-cysteine, was isolated from the urine of rats after the subcutaneous injection of each of the following compounds: triallyl phosphate, sodium allyl sulphate and allyl nitrate. The sulphoxide of allylmercapturic acid was detected in the urine excreted by these rats. 3. 3-Hydroxypropylmercapturic acid was identified by g.l.c. as a metabolite of allyl acetate, allyl stearate, allyl benzoate, diallyl phthalate, allyl nitrite, triallyl phosphate and sodium allyl sulphate. 4. S-(3-Hydroxypropyl)-l-cysteine was detected in the bile of a rat dosed with allyl acetate. PMID:4762754

Predictors and long-term reproducibility of urinary phthalate metabolites in middle-aged men and women living in urban Shanghai

PubMed Central

Starling, Anne P.; Engel, Lawrence S.; Calafat, Antonia M.; Koutros, Stella; Satagopan, Jaya M.; Yang, Gong; Matthews, Charles E.; Cai, Qiuyin; Buckley, Jessie P.; Ji, Bu-Tian; Cai, Hui; Chow, Wong-Ho; Zheng, Wei; Gao, Yu-Tang; Rothman, Nathaniel; Xiang, Yong-Bing; Shu, Xiao-Ou

2015-01-01

Phthalate esters are man-made chemicals commonly used as plasticizers and solvents, and humans may be exposed through ingestion, inhalation, and dermal absorption. Little is known about predictors of phthalate exposure, particularly in Asian countries. Because phthalates are rapidly metabolized and excreted from the body following exposure, it is important to evaluate whether phthalate metabolites measured at a single point in time can reliably rank exposures to phthalates over a period of time. We examined the concentrations and predictors of phthalate metabolite concentrations among 50 middle-aged women and 50 men from two Shanghai cohorts, enrolled in 1997-2000 and 2002-2006, respectively. We assessed the reproducibility of urinary concentrations of phthalate metabolites in three spot samples per participant taken several years apart (mean interval between first and third sample was 7.5 years [women] or 2.9 years [men]), using Spearman's rank correlation coefficients and intra-class correlation coefficients. We detected ten phthalate metabolites in at least 50% of individuals for two or more samples. Participant sex, age, menopausal status, education, income, body mass index, consumption of bottled water, recent intake of medication, and time of day of collection of the urine sample were associated with concentrations of certain phthalate metabolites. The reproducibility of an individual's urinary concentration of phthalate metabolites across several years was low, with all intra-class correlation coefficients and most Spearman rank correlation coefficients ≤ 0.3. Only mono(2-ethylhexyl) phthalate, a metabolite of di(2-ethylhexyl)phthalate, had a Spearman rank correlation coefficient ≥ 0.4 among men, suggesting moderate reproducibility. These findings suggest that a single spot urine sample is not sufficient to rank exposures to phthalates over several years in an adult urban Chinese population. PMID:26255822

The occurrence and ecological risk assessment of phthalate esters (PAEs) in urban aquatic environments of China.

PubMed

Zhang, Lulu; Liu, Jingling; Liu, Huayong; Wan, Guisheng; Zhang, Shaowei

2015-07-01

Phthalate esters (PAEs) are widely used in the manufacturing of plastics, and the demand for PAEs has grown rapidly, especially in China. This trend will lead to much more environmental PAE contamination. PAEs are listed as priority substances in the European Union and are therefore subject to ecological risk assessments. This paper reviews the literature concerning the pollution status of PAEs and their ecological risk to aquatic environments. Risk quotients (RQs) based on the predicted no effect concentration and PAE concentrations in aquatic environments demonstrated significant (10 ≤ RQ < 100) or expected (RQ ≥ 100) potential adverse effects for algae, Daphnia, and fish in aquatic environments near PAE-based industrial and urban areas. Thus, the ecological risk of PAEs in Chinese aquatic environments should be considered, especially in areas where commercial plastics are produced.

A solid-phase microextraction fiber with carbon nanoparticles as sorbent material prepared by a simple flame-based preparation process.

PubMed

Sun, Min; Feng, Juanjuan; Qiu, Huamin; Fan, Lulu; Li, Leilei; Luo, Chuannan

2013-07-26

A novel carbon nanoparticles-coated solid-phase microextraction (SPME) fiber was prepared via a simple and low-cost flame-based preparation process, with stainless steel wire as support. Surface characteristic of the fiber was studied with scanning electron microscope. A nano-scaled brushy structure was observed. Coupled to gas chromatography (GC), the fiber was used to extract phthalate esters (PAEs) and polycyclic aromatic hydrocarbons (PAHs) in aqueous samples. Analytical performances of the proposed method were investigated under the optimum extraction conditions (extraction temperature, 40°C; content of KCl, 30% (w/v); extraction time, 50min for PAEs and 40min for PAHs) and compared with other reports for the same analytes. Calibration ranges were 0.06-500μgL(-1) for di-n-butyl phthalate (DBP), and 0.1-300μgL(-1) for di-cyclohexyl phthalate (DCHP) and di-(2-ethyl-hexyl) phthalate (DEHP). For the eight PAHs, good linearity was obtained ranging from 0.01 to 150μgL(-1). Limits of detection were 0.005μgL(-1) for three PAEs and 0.001-0.003μgL(-1) for eight PAHs. The fiber exhibited excellent stability. It can be used for 100 times with RSDs of extraction efficiency less than 22.4%. The as-established SPME-GC method was applied to determine PAEs in food-wrap and PAHs in cigarette ash and snow water, and satisfactory results were obtained. The carbon nanoparticles-coated SPME fiber was efficient for sampling of organic compounds from aqueous samples. Copyright © 2013 Elsevier B.V. All rights reserved.

A yeast bioassay for direct measurement of thyroid hormone disrupting effects in water without sample extraction, concentration, or sterilization.

PubMed

Li, Jian; Ren, Shujuan; Han, Shaolun; Li, Na

2014-04-01

The present study introduces an improved yeast bioassay for rapid yet sensitive evaluation of thyroid hormone disruption at the level of thyroid receptor (TR) in environmental water samples. This assay does not require water sample preparation and thus requires very little hands-on time. Based on different β-galactosidase substrates, two modified bioassays, a colorimetric bioassay and a chemiluminescent bioassay, were developed. The compounds tested included the known thyroid hormone 3,3',5-triiodo-l-thyronine (T3), the specific TR antagonist amiodarone hydrochloride (AH) and phthalate esters (PAEs), which potentially disrupt thyroid hormone signaling. The EC50 values for T3 were similar to those previously obtained using a 96-well plate bioassay. TR antagonism by AH was studied in the presence of 2.5 × 10(-7)M T3, and the concentration producing 20% of the maximum effect (RIC20) for AH was 3.1 × 10(-7)M and 7.8 × 10(-9)M for the colorimetric bioassay and chemiluminescent bioassay, respectively. None of the tested PAEs induced β-galactosidase expression, but diethylhexyl phthalate, benzyl butyl phthalate and dibutyl phthalate demonstrated TR antagonism. Furthermore, water samples collected from Guanting reservoir in Beijing were evaluated. Although TR agonism was not observed, antagonism was detected in all water samples and is expressed as AH equivalents. The toxicology equivalent quantity values obtained by the chemiluminescent bioassay ranged from 21.2 ± 1.6 to 313.9 ± 28.8 μg L(-1) AH, and similar values were obtained for the colorimetric bioassay. The present study shows that the modified yeast bioassay can be used as a valuable tool for quantification of thyroid hormone disrupting effects in environmental water samples. Copyright © 2013 Elsevier Ltd. All rights reserved.

Fast microextraction of phthalate acid esters from beverage, environmental water and perfume samples by magnetic multi-walled carbon nanotubes.

PubMed

Luo, Yan-Bo; Yu, Qiong-Wei; Yuan, Bi-Feng; Feng, Yu-Qi

2012-02-15

In this work, magnetic carbon nanotubes (CNTs) were prepared by mixing the magnetic particles and multi-walled carbon nanotubes dispersed solutions. Due to their excellent adsorption capability towards hydrophobic compounds, the magnetic CNTs were used as adsorbent of magnetic solid-phase extraction (MSPE) to extract phthalate acid esters (PAEs), which are widely used in many consumable products with potential carcinogenic properties. By coupling MSPE with gas chromatography/mass spectrometry (GC/MS), a rapid, sensitive and cost-effective method for the analysis of PAEs was established. Our results showed that the limits of detection (LODs) of 16 PAEs ranged from 4.9 to 38 ng L(-1), which are much lower compared to the previously reported methods. And good linearities of the detection method were obtained with correlation coefficients (R(2)) between 0.9821 and 0.9993. In addition, a satisfying reproducibility was achieved by evaluating the intra- and inter-day precisions with relative standard deviations (RSDs) less than 11.7% and 14.6%, respectively. Finally, the established MSPE-GC/MS method was successfully applied to the determination of PAEs from bottled beverages, tap water and perfume samples. The recoveries of the 16 PAEs from the real samples ranged from 64.6% to 125.6% with the RSDs less than 16.5%. Taken together, the MSPE-GC/MS method developed in current study provides a new option for the detection of PAEs from real samples with complex matrices. Copyright © 2012 Elsevier B.V. All rights reserved.

Electrochemical preparation of polyaniline-polypyrrole solid-phase microextraction coating and its application in the GC determination of several esters.

PubMed

Zhao, Shasha; Wu, Mian; Zhao, Faqiong; Zeng, Baizhao

2013-12-15

A novel polyaniline-polypyrrole (PANI-PPY) composite film coated stainless steel wire was prepared by cyclic voltammetry. Firstly, PANI was electrodeposited on a stainless steel wire from a solution containing 0.1 M aniline and 1M HNO3, after the PANI coating was dried in air PPY was electrodeposited on it from a solution containing 0.1 M pyrrole and 0.1 M p-methylbenzene sulfonic acid. The resulting PANI-PPY fiber showed reticulate structure and had large specific surface area. When it was used for the headspace solid-phase microextraction of several esters (i.e. methyl anthranilate, ethyl-o-aminobenzoate, dimethyl phthalate, methyl laurate, and diethyl phthalate), followed by gas chromatographic determination, it presented higher extraction capability in comparison with PPY and PANI coatings. Under the optimized conditions, the linear ranges were 0.07-300 μg L(-1) and the detection limits were 0.05-0.38 μg L(-1) for different esters. The PANI-PPY fiber also showed high durability, after being used for about 160 times its extraction capacity only changed a little. The proposed method was successfully applied to the determination of these esters in real samples and the recoveries were 90-102%. © 2013 Elsevier B.V. All rights reserved.

Estrogenic effects in the influents and effluents of the drinking water treatment plants.

PubMed

Gou, Yan-You; Lin, Susana; Que, Danielle E; Tayo, Lemmuel L; Lin, Ding-Yan; Chen, Kuan-Chung; Chen, Fu-An; Chiang, Pen-Chi; Wang, Gen-Shuh; Hsu, Yi-Chyuan; Chuang, Kuo Pin; Chuang, Chun-Yu; Tsou, Tsui-Chun; Chao, How-Ran

2016-05-01

Estrogen-like endocrine disrupting compounds (EEDC) such as bisphenol A, nonylphenol, and phthalic acid esters are toxic compounds that may occur in both raw- and drinking water. The aim of this study was to combine chemical- and bioassay to evaluate the risk of EEDCs in the drinking water treatment plants (DWTPs). Fifty-six samples were collected from seven DWTPs located in northern-, central-, and southern Taiwan from 2011 to 2012 and subjected to chemical analyses and two bioassay methods for total estrogenic activity (E-Screen and T47D-KBluc assay). Among of the considered EEDCs, only dibutyl phthalate (DBP) and di (2-ethylhexyl) phthalate (DEHP) were detected in both drinking and raw water samples. DBP levels in drinking water ranged from

Urinary phthalate and phthalate alternative metabolites and isoprostane among couples undergoing fertility treatment.

PubMed

Wu, Haotian; Olmsted, Alexandra; Cantonwine, David E; Shahsavari, Shahin; Rahil, Tayyab; Sites, Cynthia; Pilsner, J Richard

2017-02-01

Epidemiological data suggest associations between phthalate exposures to a variety of adverse reproductive outcomes including reduced sperm quality and reproductive success. While mechanisms of these associations are not fully elucidated, oxidative stress has been implicated as a potential mediator. We examined associations of urinary metabolites of phthalates and phthalate alternative plasticizers with oxidative stress among couples seeking fertility treatment. Seventeen urinary plasticizer metabolites and 15-F2t isoprostane, a biomarker of oxidative stress, were quantified in spot samples from 50 couples seeking fertility treatment who enrolled in the Sperm Environmental Epigenetics and Development Study during 2014-2015. In multivariable analyses, percent change in isoprostane was positively associated with interquartile range increases for the oxidative metabolites of di-2-ethylhexyl phthalate, [mono-2-ethyl-5-hydroxyhexyl phthalate (MEHHP; 20.0%, p=0.02), mono-2-ethyl-5-oxohexyl phthalate (MEOHP; 24.1%, p=0.01), and mono-2-ethyl-5-carboxypentyl phthalate (MECPP; 24.1%, p=0.004)], mono-isobutyl phthalate (MiBP; 17.8%, p=0.02), mono-hydroxyisobutyl phthalate (MHiBP; 27.5%, p=0.003), and cyclohexane-1,2-dicarboxylic acid mono-hydroxy-isononyl ester (MHINCH; 32.3%, p=0.002). Stratification of participants by sex revealed that isoprostane was positively associated with MHiBP (41.4%, p=0.01) and monocarboxy-isononyl phthalate (MCNP; 26.0%, p=0.02) among females and MEOHP (35.8%, p=0.03), MiBP (29.2%, p=0.01), MHiBP (34.7%, p=0.007) and MHINCH (49.0%, p=0.002) among males. Our results suggest that exposure to phthalates and phthalate replacements are associated with higher levels of oxidative stress in a sex-specific manner. Additional studies are needed to replicate our findings and to examine the potential health implications of the use of phthalates and alternative phthalates in consumer end products. Copyright © 2016 Elsevier Inc. All rights reserved.

Current exposure of 200 pregnant Danish women to phthalates, parabens and phenols.

PubMed

Tefre de Renzy-Martin, Katrine; Frederiksen, Hanne; Christensen, Jeppe Schultz; Boye Kyhl, Henriette; Andersson, Anna-Maria; Husby, Steffen; Barington, Torben; Main, Katharina M; Jensen, Tina Kold

2014-01-01

Many phthalates, parabens and phenols are suspected to have endocrine-disrupting properties in humans. They are found in consumer products, including food wrapping, cosmetics and building materials. The foetus is particularly vulnerable and exposure to these chemicals therefore is of concern for pregnant women. We investigated current exposure to several commonly used phthalates, parabens and phenols in healthy, pregnant Danish women. A total of 200 spot urine samples were collected between 8 and 30 weeks of gestation and analysed for metabolites of ten phenols, seven parabens and 16 phthalate by liquid chromatography-tandem mass spectrometry representing 26 non-persistent compounds. The majority of analytes were present in the urine sample collected from most women who participated. Thus, in 174 of the 200 women, metabolites of more than 13 (>50%) of 26 compounds were detected simultaneously. The number of compounds detected per woman (either as the parent compound or its metabolite(s)) ranged from 7 to 21 with a median of 16. The majority of compounds correlated positively with each other within and between chemical groups, suggesting combined exposure sources. Estimated daily intakes (DIs) of phthalates and bisphenol A (BPA) were below their individual tolerable DI (TDI) and with hazard quotients below 1. In conclusion, we found detectable levels of phthalate metabolites, parabens and phenols in almost all pregnant women, suggesting combined multiple exposures. Although the estimated DI of phthalates and BPA for an individual was below TDI, our results still raise concern, as current toxicological risk assessments in humans do not take into account simultaneous exposure. The true cumulative risk for the foetus may therefore be underestimated.

Rapid detection of hazardous chemicals in textiles by direct analysis in real-time mass spectrometry (DART-MS).

PubMed

Antal, Borbála; Kuki, Ákos; Nagy, Lajos; Nagy, Tibor; Zsuga, Miklós; Kéki, Sándor

2016-07-01

Residues of chemicals on clothing products were examined by direct analysis in real-time (DART) mass spectrometry. Our experiments have revealed the presence of more than 40 chemicals in 15 different clothing items. The identification was confirmed by DART tandem mass spectrometry (MS/MS) experiments for 14 compounds. The most commonly detected hazardous substances were nonylphenol ethoxylates (NPEs), phthalic acid esters (phthalates), amines released by azo dyes, and quinoline derivates. DART-MS was able to detect NPEs on the skin of the person wearing the clothing item contaminated by NPE residuals. Automated data acquisition and processing method was developed and tested for the recognition of NPE residues thereby reducing the analysis time.

Determining Source Strength of Semivolatile Organic Compounds using Measured Concentrations in Indoor Dust

PubMed Central

Shin, Hyeong-Moo; McKone, Thomas E.; Nishioka, Marcia G.; Fallin, M. Daniele; Croen, Lisa A.; Hertz-Picciotto, Irva; Newschaffer, Craig J.; Bennett, Deborah H.

2014-01-01

Consumer products and building materials emit a number of semivolatile organic compounds (SVOCs) in the indoor environment. Because indoor SVOCs accumulate in dust, we explore the use of dust to determine source strength and report here on analysis of dust samples collected in 30 U.S. homes for six phthalates, four personal care product ingredients, and five flame retardants. We then use a fugacity-based indoor mass-balance model to estimate the whole house emission rates of SVOCs that would account for the measured dust concentrations. Di-2-ethylhexyl phthalate (DEHP) and di-iso-nonyl phthalate (DiNP) were the most abundant compounds in these dust samples. On the other hand, the estimated emission rate of diethyl phthalate (DEP) is the largest among phthalates, although its dust concentration is over two orders of magnitude smaller than DEHP and DiNP. The magnitude of the estimated emission rate that corresponds to the measured dust concentration is found to be inversely correlated with the vapor pressure of the compound, indicating that dust concentrations alone cannot be used to determine which compounds have the greatest emission rates. The combined dust-assay modeling approach shows promise for estimating indoor emission rates for SVOCs. PMID:24118221

Occurrence and risk assessment of phthalate esters (PAEs) in agricultural soils of the Sanjiang Plain, northeast China.

PubMed

Wang, He; Liang, Hong; Gao, Da-Wen

2017-08-01

This study looks at the pollution status of six priority control phthalate esters (PAEs) under different cultivation of agricultural soils in the Sanjiang Plain, northeast China. Results show the total concentration of PAEs ranged from 162.9 to 946.9 μg kg -1 with an average value of 369.5 μg kg -1 . PAE concentrations in three types of cultivated soils exhibited decreasing order paddy field (532.1 ± 198.1 μg kg -1 ) > vegetable field (308.2 ± 87.5 μg kg -1 ) > bean field (268.2 ± 48.3 μg kg -1 ). Di-(2-ethylhexyl) phthalate (DEHP) and di-n-butyl phthalate (DnBP) were the most abundant PAEs congeners. Compared with previous studies, agricultural soils in the Sanjiang Plain showed relatively low contamination levels. Anthropogenic activities such as cultivation practices and industrial emissions were associated with the distribution pattern of PAEs. Furthermore, human health risks of PAEs were estimated and the non-cancer risk shown negligible but carcinogenic risk of DEHP exceeded the threshold limits value. PAE contaminants originated from cultivation practices and intense anthropogenic activities result in placing the agricultural soils under a potential risk to human health and also to ecosystems in the Sanjiang Plain. Therefore, the contamination status of PAEs in agricultural soil and potential impacts on human health should attract considerable attention.

Study on the leaching of phthalates from polyethylene terephthalate bottles into mineral water.

PubMed

Keresztes, Szilvia; Tatár, Enikő; Czégény, Zsuzsanna; Záray, Gyula; Mihucz, Victor G

2013-08-01

Carbonated and non-carbonated mineral water samples bottled in 0.5-L, 1.5-L and 2.0-L polyethylene terephthalate (PET) containers belonging to three different water brands commercialized in Hungary were studied in order to determine their phthalate content by gas chromatography-mass spectrometry. Among the six investigated phthalates, diisobutyl phthalate, di-n-butyl-phthalate, benzyl-butyl phthalate and di(2-ethyl-hexyl) phthalate (DEHP) were determined in non-carbonated samples as follows: <3.0 ng L(-1)-0.2 μg L(-1), <6.6 ng L(-1)-0.8 μg L(-1), <6.0 ng L(-1)-0.1 μg L(-1) and <16.0 ng L(-1)-1.7 μg L(-1), respectively. Any of the above-mentioned phthalate esters could be detected in carbonated mineral water samples. DEHP was the most abundant phthalate in the investigated samples. It could be detected after 44 days of storage at 22 °C and its leaching was the most pronounced when samples were stored over 1200 days. Mineral water purchased in PET bottles of 0.5L had the highest phthalate concentrations compared to those obtained for waters of the identical brand bottled in 1.5-L or 2.0-L PET containers due to the higher surface/volume ratio. No clear trend could be established for phthalate leaching when water samples were kept at higher temperatures (max. 60 °C) showing improper storage conditions. Phthalate determination by pyrolysis-gas chromatography/mass spectrometric measurements in the plastic material as well as in the aqueous phase proved the importance of the quality of PET raw material used for the production of the pre-form (virgin vs. polymer containing recycled PET). Copyright © 2013 Elsevier B.V. All rights reserved.

Adsorptive removal of phthalate ester (Di-ethyl phthalate) from aqueous phase by activated carbon: a kinetic study.

PubMed

Venkata Mohan, S; Shailaja, S; Rama Krishna, M; Sarma, P N

2007-07-19

Adsorptive studies were carried out on Di-ethyl phthalate (DEP) removal from aqueous phase onto activated carbon. Batch sorption studies were performed and the results revealed that activated carbon demonstrated ability to adsorb DEP. Influence of varying experimental conditions such as DEP concentration, pH of aqueous solution, and dosage of adsorbent were investigated on the adsorption process. Sorption interaction of DEP onto activated carbon obeyed the pseudo second order rate equation. Experimental data showed good fit with both the Langmuir and Freundlich adsorption isotherm models. DEP sorption was found to be dependent on the aqueous phase pH and the uptake was observed to be greater at acidic pH.

In vitro effects of phthalate esters in human myometrial and leiomyoma cells and increased urinary level of phthalate metabolite in women with uterine leiomyoma.

PubMed

Kim, Jin Hee; Kim, Sung Hoon; Oh, Young Sang; Ihm, Hyo Jin; Chae, Hee Dong; Kim, Chung-Hoon; Kang, Byung Moon

2017-04-01

To investigate the possible role of phthalate, a ubiquitous chemical used in consumer products, in the pathogenesis of uterine leiomyoma. Experimental and prospective case-control study using human samples. University hospital. Fifty-three women with histologic evidence of uterine leiomyoma and 33 surgical controls without leiomyoma. Human myometrial and leiomyoma cells were treated with di-(2-thylhexyl)-phthalate (DEHP). Cell viability assay and Western blot analyses after in vitro DEHP treatment; high-performance liquid chromatography electrospray ionization tandem mass spectrometry in cases and controls. In vitro treatment with DEHP led to an increased viability and increased expressions of proliferating cell nuclear antigen, B-cell lymphoma 2 protein, and type I collagen in myometrial and leiomyoma cells. The urinary concentration of mono-(2-ethyl-5-carboxypentyl) phthalate was higher in women with leiomyoma compared with controls. These findings suggest that exposure to phthalate may play a role in the pathogenesis of uterine leiomyoma by enhancing proliferative activity, exerting an antiapoptotic effect, and increasing collagen contents in myometrial and leiomyoma cells. Copyright © 2017 American Society for Reproductive Medicine. Published by Elsevier Inc. All rights reserved.

Simultaneous extraction and determination of phthalate esters in aqueous solution by yolk-shell magnetic mesoporous carbon-molecularly imprinted composites based on solid-phase extraction coupled with gas chromatography-mass spectrometry.

PubMed

Yang, Rui; Liu, Yuxin; Yan, Xiangyang; Liu, Shaomin

2016-12-01

A rapid, sensitive and accurate method for the simultaneous extraction and determination of five types of trace phthalate esters (PAEs) in environmental water and beverage samples using magnetic molecularly imprinted solid-phase extraction (MMIP-SPE) coupled with gas chromatography-mass spectrometry (GC-MS) was developed. A novel type of molecularly imprinted polymers on the surface of yolk-shell magnetic mesoporous carbon (Fe 3 O 4 @void@C-MIPs) was used as an efficient adsorbent for selective adsorption of phthalate esters based on magnetic solid-phase extraction (MSPE). The real samples were first preconcentrated by Fe 3 O 4 @void@C-MIPs, subsequently extracted by eluent and finally determined by GC-MS after magnetic separation. Several variables affecting the extraction efficiency of the analytes, including the type and volume of the elution solvent, amount of adsorbent, extraction time, desorption time and pH of the sample solution, were investigated and optimized. Validation experiments indicated that the developed method presented good linearity (R 2 >0.9961), satisfactory precision (RSD<6.7%), and high recovery (86.1-103.1%). The limits of detection ranged from 1.6ng/L to 5.2ng/L and the enrichment factor was in the range of 822-1423. The results indicated that the novel method had the advantages of convenience, good sensitivity, and high efficiency, and it could also be successfully applied to the analysis of PAEs in real samples. Copyright © 2016. Published by Elsevier B.V.

Using exposure prediction tools to link exposure and dosimetry for risk-based decisions: A case study with phthalates

EPA Science Inventory

A few different exposure prediction tools were evaluated for use in the new in vitro-based safety assessment paradigm using di-2-ethylhexyl phthalate (DEHP) and dibutyl phthalate (DnBP) as case compounds. Daily intake of each phthalate was estimated using both high-throughput (HT...

Manmade organic compounds in the surface waters of the United States: a review of current understanding

USGS Publications Warehouse

Smith, James A.; Witkowski, Patrick J.; Fusillo, Thomas V.

1987-01-01

This report reviews the occurrence and distribution of manmade organic compounds in the surface waters of the United States. On the basis of their aqueous solubilities, nonionic organic compounds partition themselves between water, dissolved organic matter, particulate organic matter, and the lipid reservoirs of aquatic organisms. Ionized organic compounds can be absorbed to sediments, thereby reducing their aqueous concentrations. Transformation processes of photolysis, hydrolysis, biodegradation, and volatilization can attenuate organic compounds, and attenuation rate commonly follow a first-order kinetic process. Eight groups of manmade organic compounds are discussed: 1. Polychlorinated biphenyls and organochlorine insecticides, 2. Carbamate and organophosphorus insecticides, 3. Herbicides, 4. Phenols, 5. Halogenated aliphatic and monocyclic aromatic hydrocarbons, 6. Phthalate esters, 7. Polychlorinated dibenzo-p-dioxins, and 8. Polycyclic aromatic hydrocarbons. For each compound group, data pertaining to use, production, and properties are presented and discussed. Processes that influence that the environmental fate of each group, as determined primarily through laboratory studies, are reviewed, and important fate processes are identified. Environmental concentrations of compounds from each group in water, biota, and sediment are given to demonstrate representative values for comparison to concentrations determined during ongoing research. Finally, where sufficient data exist, regional and temporal contamination trends in the United States are discussed.

Manmade organic compounds in the surface waters of the United States; a review of current understanding

USGS Publications Warehouse

Smith, James A.; Witkowski, P.J.; Fusillo, Thomas V.

1988-01-01

This report reviews the occurrence and distribution of manmade organic compounds in the surface waters of the United States. On the basis of their aqueous solubilities, nonionic organic compounds partition themselves among water, dissolved organic matter, particulate organic matter, and the lipid reservoirs of aquatic organisms. Ionized organic compounds can be adsorbed to sediments, thereby reducing their aqueous concentrations. Transformation processes of photolysis, hydrolysis, biodegradation, and volatilization can attenuate organic compounds, and attenuation rates commonly follow a first-order kinetic process. Eight groups of manmade organic compounds are discussed: 1. Polychlorinated biphenyls and organochlorine insecticides, 2. Carbamate and organophosphorus insecticides, 3. Herbicides, 4. Phenols, 5. Halogenated aliphatic and monocyclic aromatic hydrocarbons, 6. Phthalate esters, 7. Polychlorinated dibenzo-p-dioxins, and 8. Polycyclic aromatic hydrocarbons. For each compound group, data pertaining to use, production, and properties are presented and discussed. Processes that influence the environmental fate of each group, as determined primarily through laboratory studies, are reviewed, and important fate processes are identified. Environmental concentrations of compounds from each group in water, biota, and sediment are given to demonstrate representative values for comparison with concentrations determined during ongoing research. Finally, where data are sufficient, regional and temporal contamination trends in the United States are discussed.

Semivolatile organic compounds in residential air along the Arizona-Mexico border.

PubMed

Gale, Robert W; Cranor, Walter L; Alvarez, David A; Huckins, James N; Petty, Jimmie D; Robertson, Gary L

2009-05-01

Concerns about indoor air quality and the potential effects on people living in these environments are increasing as more reports about the toxicities and the potential indoor air exposure levels of household-use chemicals and chemicals from housing and fumishing manufacture in air are being assessed. Gas chromatography/mass spectromery was used to confirm numerous airborne contaminants obtained from the analysis of semipermeable membrane devices deployed inside of 52 homes situated along the border between Arizona and Mexico. We also describe nontarget analytes in the organochlorine pesticide fractions of 12 of these homes; this fraction is also the most likely to contain the broadest scope of bioconcentratable chemicals accumulated from the indoor air. Approximately 400 individual components were identified, ranging from pesticides to a wide array of hydrocarbons, fragrances such as the musk xylenes, flavors relating to spices, aldehydes, alcohols, esters and phthalate esters, and other miscellaneous types of chemicals. The results presented in this study demonstrate unequivocally that the mixture of airborne chemicals present indoors is far more complex than previously demonstrated.

Effect of torrefaction pretreatment on the pyrolysis of rubber wood sawdust analyzed by Py-GC/MS.

PubMed

Chen, Wei-Hsin; Wang, Chao-Wen; Kumar, Gopalakrishnan; Rousset, Patrick; Hsieh, Tzu-Hsien

2018-07-01

The aim of this study was to investigate the effect of torrefaction on the pyrolysis of rubber wood sawdust (RWS) using pyrolysis-gas chromatography/mass spectrometry (Py-GC/MS). Three typical torrefaction temperatures (200, 250, and 300 °C) and pyrolysis temperatures (450, 500, and 550 °C) were considered. The results suggested that only diethyl phthalate, belonging to esters, was detected at the torrefaction temperatures of 200 and 250 °C, revealing hemicellulose degradation. With the torrefaction temperature of 300 °C, esters, aldehydes, and phenols were detected, suggesting the predominant decomposition of hemicellulose and lignin. The double-shot pyrolysis indicated that the contents of oxy-compounds such as acids and aldehydes in pyrolysis bio-oil decreased with rising torrefaction temperature, implying that increasing torrefaction severity abated oxygen content in the bio-oil. With the torrefaction temperature of 300 °C, relatively more cellulose was retained in the biomass because the carbohydrate content in the pyrolysis bio-oil increased significantly. Copyright © 2018 Elsevier Ltd. All rights reserved.

Adjuvant effect of short chain triacylglycerol tributyrin on a mouse contact hypersensitivity model.

PubMed

Sekiguchi, Kota; Ogawa, Erina; Kurohane, Kohta; Konishi, Hideyuki; Mochizuki, Narumi; Manabe, Kei; Imai, Yasuyuki

2018-03-01

Little attention has been paid to chemicals that can enhance hypersensitivity caused by other chemicals. We have demonstrated that phthalate esters with short chain alcohols enhance fluorescein isothiocyanate (FITC)-induced contact hypersensitivity (CHS) in a mouse model. Furthermore, phthalate esters with such an enhancing effect were found to activate transient receptor potential ankyrin 1 (TRPA1) cation channels, which are expressed on a part of sensory neurons, using a TRPA1-expressing cell line. In this study, we examined these activities of esters comprising glycerol and a short chain fatty acid, i.e. dibutyrin and tributyrin. We carried out chemical synthesis of dibutyrin isomers. Each dibutyrin isomer weakly activated TRPA1 and slightly enhanced skin sensitization to FITC. Unexpectedly, TRPA1 activation and enhancement of FITC-CHS were much more evident in the presence of tributyrin. Mechanistically, tributyrin induced increased dendritic cell trafficking from the skin to draining lymph nodes. Tributyrin enhanced interferon-γ (IFN-γ) production by draining lymph nodes, while its effect on interleukin-4 (IL-4) production was relatively less prominent. These results suggested that tributyrin concomitantly caused TRPA1 activation and an adjuvant effect on FITC-CHS. Copyright © 2017 Elsevier B.V. All rights reserved.

Phthalate esters contamination in soils and vegetables of plastic film greenhouses of suburb Nanjing, China and the potential human health risk.

PubMed

Ma, Ting Ting; Wu, Long Hua; Chen, Like; Zhang, Hai Bo; Teng, Ying; Luo, Yong Ming

2015-08-01

The contamination of phthalate esters (PAEs) has become a potential threat to the environment and human health because they could be easily released as plasticizers from the daily supply products, especially in polyethylene films. Concentration levels of total six PAEs, nominated as priority pollutants by the US Environmental Protection Agency (USEPA), were investigated in soils and vegetables from four greenhouse areas in suburbs of Nanjing, East China. Total PAEs concentration ranged from 930 ± 840 to 2,450 ± 710 μg kg(-1) (dry weight (DW)) in soil and from 790 ± 630 to 3,010 ± 2,130 μg kg(-1) in vegetables. Higher concentrations of PAEs were found in soils except in Suo Shi (SS) area and in vegetables, especially in potherb mustard and purple tsai-tai samples. Risk assessment mainly based on the exposures of soil ingestion and daily vegetable intake indicated that bis(2-ethylhexyl) phthalate (DEHP) in the samples from Gu Li (GL) and Hu Shu (HS) exhibited the highest hazard to children less than 6-year old. Therefore, the human health risk of the PAEs contamination in soils and vegetables should greatly be of a concern, especially for their environmental estrogen analog effects.

Gas chromatography with mass spectrometry for the determination of phthalates preconcentrated by microextraction based on an ionic liquid.

PubMed

Cacho, Juan Ignacio; Campillo, Natalia; Viñas, Pilar; Hernández-Córdoba, Manuel

2017-03-01

A new procedure is proposed for the analysis of migration test solutions obtained from plastic bottles used in the packaging of edible oils. Ultrasound-assisted emulsification microextraction with ionic liquids was applied for the preconcentration of six phthalate esters: dimethylphthalate, diethylphthalate, di-n-butylphthalate, n-butylbenzylphthalate, di-2-ethylhexylphthalate, and di-n-octylphthalate. The enriched ionic liquid was directly analyzed by gas chromatography and mass spectrometry using direct insert microvial thermal desorption. The different factors affecting the microextraction efficiency, such as volume of the extracting phase (30 μL of the ionic liquid) and ultrasound application time (25 s), and the thermal desorption step, such as desorption temperature and time, and gas flow rate, were studied. Under the selected conditions, detection limits for the analytes were in the 0.012-0.18 μg/L range, while recovery assays provided values ranging from 80 to 112%. The use of butyl benzoate as internal standard increased the reproducibility of the analytical procedure. When the release of the six phthalate esters from the tested plastic bottles to liquid simulants was monitored using the optimized procedure, analyte concentrations of between 1.0 and 273 μg/L were detected. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Bis(trifluoromethanesulfonyl)imide-based ionic liquids grafted on graphene oxide-coated solid-phase microextraction fiber for extraction and enrichment of polycyclic aromatic hydrocarbons in potatoes and phthalate esters in food-wrap.

PubMed

Hou, Xiudan; Guo, Yong; Liang, Xiaojing; Wang, Xusheng; Wang, Lei; Wang, Licheng; Liu, Xia

2016-06-01

A class of novel, environmental friendly ionic liquids (ILs) were synthesized by on-fiber preparation strategy and modified on graphene oxide (GO)-coated stainless steel wire, which was used as a solid-phase microextraction (SPME) fiber for efficient enrichment of polycyclic aromatic hydrocarbons (PAHs) and phthalate esters (PAEs). Surface characteristic of the ILs and polymeric-ILs (PILs) fibers with the wave-structure were inspected by scanning electron microscope. The successfully synthesis of bis(trifluoromethanesulfonyl)imide (NTf2(-))-based ILs were also characterized by energy dispersive spectrometer analysis. Through the chromatograms of the proposed two ILs (1-aminoethyl-3-methylimidazolium bromide (C2NH2MIm(+)Br(-)), C2NH2MIm(+)NTf2(-)) and two PILs (polymeric 1-vinyl-3-hexylimidazolium bromide (poly(VHIm(+)Br(-))), poly(VHIm(+)NTf2(-)))-GO-coated fibers for the extraction of analytes, NTf2(-)-based PIL demonstrated higher extraction capacity for hydrophobic compounds than other as-prepared ILs. Analytical performances of the proposed fibers were investigated under the optimized extraction and desorption conditions coupled with gas chromatography (GC). Compared with the poly(VHIm(+)Br(-))-GO fiber, the poly(VHIm(+)NTf2(-))-GO SPME fiber brought wider linear ranges for analytes with correlation coefficient in the range of 0.9852-0.9989 and lower limits of detection ranging from 0.015-0.025μgL(-1). The obtained results indicated that the newly prepared PILs-GO coating was a feasible, selective and green microextraction medium, which could be suitable for extraction and determination of PAHs and PAEs in potatoes and food-wrap sample, respectively. Copyright © 2016 Elsevier B.V. All rights reserved.

Determination of alkylphenols and phthalate esters in vegetables and migration studies from their packages by means of stir bar sorptive extraction coupled to gas chromatography-mass spectrometry.

PubMed

Cacho, J I; Campillo, N; Viñas, P; Hernández-Córdoba, M

2012-06-08

This paper describes a method for the determination of three alkylphenols (APs), 4-tert-octylphenol (tOP), 4-n-octylphenol (OP) and 4-nonylphenol (NP), and six phthalate esters (PEs), dimethylphthalate (DMP), diethylphthalate (DEP), di-n-butylphthalate (DBP), n-butylbenzylphthalate (BBP), di-2-ethylhexylphthalate (DEHP) and di-n-octylphthalate (DOP), in vegetables using stir bar sorptive extraction (SBSE) in combination with thermal desorption-gas chromatography-mass spectrometry (TD-GC-MS). Ultrasonic radiation was used to extract the analytes from the solid food matrix, and the extract obtained was preconcentrated by SBSE. The different parameters affecting both stages were carefully optimized. The method was applied to analyze commercial vegetables, in the form of plastic packed salads and canned greens, as well as the corresponding filling liquids of the canned food. Quantification of the samples was carried out against aqueous standards using an internal standard (anthracene). The analysis of a 2 g vegetable sample provided detection limits between 12.7 and 105.8 pg g⁻¹ for OP and DEHP, respectively. Migration studies from the plastic packages of the vegetables samples analyzed were carried out. DEP, DBP and DEHP were found to have migrated from the bags to the simulant and the same compounds were quantified in lettuce, corn salad, arugula, parsley and chard, at concentration levels in the 8-51 ng g⁻¹ range. However, OP and NP were found in only two vegetable samples and one filling liquid, but neither was detected in any package. The proposed method provided recoveries of 83-118%. Copyright © 2012 Elsevier B.V. All rights reserved.

Inhibition of UDP-glucuronosyltransferases (UGTs) by phthalate monoesters.

PubMed

Du, Zuo; Cao, Yun-Feng; Li, Sai-Nan; Hu, Cui-Min; Fu, Zhi-Wei; Huang, Chun-Ting; Sun, Xiao-Yu; Liu, Yong-Zhe; Yang, Kun; Fang, Zhong-Ze

2018-04-01

Phthalate monoesters are important metabolites of phthalate esters (PAEs) which have been extensively utilized in industry. This study aims to investigate the inhibition of phthalate monoesters on the activity of various isoforms of UDP-glucuronosyltransferases (UGTs), trying to elucidate the toxicity mechanism of environmental endocrine disruptors from the new perspectives. In vitro recombinant UGTs-catalyzed glucuronidation of 4-methylumbelliferone (4-MU) was employed to evaluate 8 kinds of phthalate monoesters on 11 sorts of main human UGT isoforms. 100 μM phthalate monoesters exhibited negligible inhibition towards the activity of UGT1A1, UGT1A3, UGT1A6, UGT1A8, UGT1A10, UGT2B4, UGT2B7, UGT2B15 and UGT2B17. The activity of UGT1A7 was strongly inhibited by monoethylhexyl phthalate (MEHP), but slightly inhibited by all the other phthalate monoesters. UGT1A9 was broadly inhibited by monobenzyl phthalate (MBZP), monocyclohexyl phthalate (MCHP), MEHP, monohexyl phthalate (MHP) and monooctyl phthalate (MOP), respectively. MEHP exhibited competitive inhibition towards UGT1A7, and MBZP, MCHP, MEHP, MHP and MOP showed competitive inhibition towards UGT1A9. The inhibition kinetic parameters (K i ) were calculated to be 11.25 μM for MEHP-UGT1A7, and 2.13, 0.09, 1.17, 7.47, 0.16 μM for MBZP-UGT1A9, MCHP-UGT1A9, MEHP-UGT1A9, MHP-UGT1A9, MOP-UGT1A9, respectively. Molecular docking indicated that both hydrogen bonds formation and hydrophobic interactions significantly contributed to the interaction between phthalate monoesters and UGT isoforms. All these information will be beneficial for understanding the adverse effects of PAEs. Copyright © 2018 Elsevier Ltd. All rights reserved.

New Cholinesterase Inhibitory Constituents from Lonicera quinquelocularis

PubMed Central

Khan, Dilfaraz; Khan, Hidayat Ullah; Khan, Farmanullah; Khan, Shafiullah; Badshah, Syed; Khan, Abdul Samad; Samad, Abdul; Ali, Farman; Khan, Ihsanullah; Muhammad, Nawshad

2014-01-01

A phytochemical investigation on the ethyl acetate soluble fraction of Lonicera quinquelocularis (whole plant) led to the first time isolation of one new phthalate; bis(7-acetoxy-2-ethyl-5-methylheptyl) phthalate (3) and two new benzoates; neopentyl-4-ethoxy-3, 5-bis (3-methyl-2-butenyl benzoate (4) and neopentyl-4-hydroxy-3, 5-bis (3-methyl-2-butenyl benzoate (5) along with two known compounds bis (2-ethylhexyl phthalate (1) and dioctyl phthalate (2). Their structures were established on the basis of spectroscopic analysis and by comparison with available data in the literature. All the compounds (1–5) were tested for their acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities in dose dependent manner. The IC50 (50% inhibitory effect) values of compounds 3 and 5 against AChE were 1.65 and 3.43 µM while the values obtained against BChE were 5.98 and 9.84 µM respectively. Compounds 2 and 4 showed weak inhibition profile. PMID:24733024

Characterization and Genomic Analysis of a Highly Efficient Dibutyl Phthalate-Degrading Bacterium Gordonia sp. Strain QH-12.

PubMed

Jin, Decai; Kong, Xiao; Liu, Huijun; Wang, Xinxin; Deng, Ye; Jia, Minghong; Yu, Xiangyang

2016-06-25

A bacterial strain QH-12 isolated from activated sludge was identified as Gordonia sp. based on analysis of 16S rRNA gene sequence and was found to be capable of utilizing dibutyl phthalate (DBP) and other common phthalate esters (PAEs) as the sole carbon and energy source. The degradation kinetics of DBP under different concentrations by the strain QH-12 fit well with the modified Gompertz model (R² > 0.98). However, strain QH-12 could not utilize the major intermediate product phthalate (phthalic acid; PA) as the sole carbon and energy source, and only a little amount of PA was detected. The QH-12 genome analysis revealed the presence of putative hydrolase/esterase genes involved in PAEs-degradation but no phthalic acid catabolic gene cluster was found, suggesting that a novel degradation pathway of PAEs was present in Gordonia sp. QH-12. This information will be valuable for obtaining a more holistic understanding on diverse genetic mechanisms of PAEs-degrading Gordonia sp. strains.

ADVERSE EFFECTS OF ENVIRONMENTAL ANTIANDROGENS AND ANDROGENS ON REPRODUCTIVE DEVELOPMENT IN MAMMALS

EPA Science Inventory

Within the last decade, several classes of chemicals have been shown in laboratory studies to disrupt reproductive development by acting as androgen receptor (AR) antagonists and/or inhibitors of fetal Leydig cell testosterone production. Some phthalate esters alter gubernacular...

Cathepsin B inhibitory activities of three new phthalate derivatives isolated from seahorse, Hippocampus Kuda Bleeler.

PubMed

Li, Yong; Qian, Zhong-Ji; Kim, Se-Kwon

2008-12-01

Three new phthalate acid derivatives, 2,12-diethyl-11-methylhexadecyl 2-ethyl-11-methylhexadecyl phthalate (1), 2-ethyldecyl 2-ethylundecyl phthalate (2), and bis(2-ethyldodecyl) phthalate (3), were isolated from seahorse, Hippocampus Kuda Bleeler, together with a known natural analog bis(2-ethylheptyl) phthalate (4). The structures of these compounds were elucidated mainly by means of the comprehensive analysis of their NMR spectroscopic data. The four phthalate derivatives showed dose-dependent cathepsin B inhibitions activities with IC(50) values of 0.13 mM (1), 0.21 mM (2), 0.18 mM (3), and 0.29 mM (4), respectively.

[Characteristics of Phthalic Acid Esters in Agricultural Soils and Products in Areas of Zhongshan City, South China].

PubMed

Li, Bin; Wu, Shan; Liang, Jin-ming; Liang, Wen-li; Chen, Gui-xian; Li, Yong-jun; Yang, Guo-yi

2015-06-01

In order to investigate and assess the pollution level of phthalic acid esters (PAEs) in farm soils and products from typical agricultural fields in areas of Zhongshan City, Guangdong Province, South China, 65 topsoil and 37 agricultural product samples were collected and contents of 6 PAEs compounds that classified by the U. S. Environmental Protection Agency (EPA) as priority pollutants were determined by the GC-FID. The results indicated that total contents of the PAEs (∑ PAEs) in soils ranged from 0. 14 to 1. 14 mg x kg(-1), and the mean value was 0.43 mg x kg(-1), with the detected ratio of 100%. Various concentrations of PAEs differed in three land-use types were ordered by vegetable soil > orchard soil > paddy soil. Comparing with six U.S. EPA priority pollutants of PAEs, the contents of Di-n-butyl phthalate (DBP) and Dimethyl phthalate ( DMP) in soils exceeded the control limits of PAEs in the American soil by 93.85% and 27.69% respectively, but the rest four PAEs compounds were lower than the control limits. Generally, the pollution level of soils contaminated by PAEs in agricultural fields of Zhongshan City was relatively low. The contents of 3 PAEs in agricultural products ranged from 0.15 to 3.15 mg x kg(-1) with the average of 1.12 mg x kg(-1), which was lower than the suggested standards in USA and Europe and with low health risk. Meanwhile, ∑ PAEs concentrations in vegetables were higher than those both in rice and fruits. DBP and DEHP were the main components of PAEs both in agricultural soils and products, with higher percentage contents and detected ratio. ∑ PAEs and DBP contents in various agricultural products-soils had a significantly positive correlation, with Pearson coefficients (r) in vegetables-vegetable soils were 0.81 (P = 0.000), 0.75 (P = 0.000), and corresponding r among rice-paddy soil and fruits-fruit soils were 0.74 (P = 0.036), 0.65 (P = 0.041) and 0.66 (P = 0.029), 0.78 (P = 0.045), respectively. Although there existed a significant difference for single PAEs compound accumulated by agricultural products, the ∑ PAEs bioconcentration factors of all agricultural products were above 1. Therefore, the accumulation characteristics of PAEs should be fully concerned when farm soil quality assessment is taken.

Current status and historical variations of phthalate ester (PAE) contamination in the sediments from a large Chinese lake (Lake Chaohu).

PubMed

Kang, Lei; Wang, Qing-Mei; He, Qi-Shuang; He, Wei; Liu, Wen-Xiu; Kong, Xiang-Zhen; Yang, Bin; Yang, Chen; Jiang, Yu-Jiao; Xu, Fu-Liu

2016-06-01

The residual levels of phthalate esters (PAEs) in the surface and two core sediments from Lake Chaohu were measured with a gas chromatograph-mass spectrometer (GC-MS). The temporal-spatial distributions, compositions of PAEs, and their effecting factors were investigated. The results indicated that di-n-butyl phthalate (DnBP), diisobutyl phthalate (DIBP), and di(2-ethylhexyl) phthalate (DEHP) were three dominant PAE components in both the surface and core sediments. The residual level of total detected PAEs (∑PAEs) in the surface sediments (2.146 ± 2.255 μg/g dw) was lower than that in the western core sediments (10.615 ± 9.733 μg/g) and in the eastern core sediments (5.109 ± 4.741 μg/g). The average content of ∑PAEs in the surface sediments from the inflow rivers (4.128 ± 1.738 μg/g dw) was an order of magnitude higher than those from the lake (0.323 ± 0.093 μg/g dw), and there were similar PAE compositions between the lake and inflow rivers. This finding means that there were important effects of PAE input from the inflow rivers on the compositions and distributions of PAEs in the surface sediments. An increasing trend was found for the residual levels of ΣPAEs, DnBP, and DIBP from the bottom to the surface in both the western and eastern core sediments. Increasing PAE usage with the population growth, urbanization, and industrial and agricultural development in Lake Chaohu watershed would result in the increasing production of PAEs and their resulting presence in the sediments. The significant positive relationships were also found between the PAE contents and the percentage of sand particles, as well as TOC contents in the sediment cores.

Simultaneous determination of phthalates, their metabolites, alkylphenols and bisphenol A using GC-MS in urine of men with fertility problems.

PubMed

Kranvogl, Roman; Knez, Jure; Miuc, Alen; Vončina, Ernest; Vončina, Darinka Brodnjak; Vlaisavljević, Veljko

2014-01-01

A GC-MS method was successfully applied to measure simultaneously the concentrations of endocrine disrupting compounds (5 dialkyl phthalates, 9 phthalate monoesters, 3 alkylphenols and bisphenol A) in 136 male urine samples. In the present study the method was validated and concentrations of EDCs were determined. The results were compared with results from other studies. Correlations between endocrine disrupting compounds and also correlations of endocrine disrupting compounds with two semen quality parameters are presented and evaluated. Significant positive correlations were found between almost all the endocrine disrupting compounds. The parameter sum of DEHP (SUM DEHP) was positively correlated to all the endocrine disrupting compounds but negatively to two semen quality parameters. Negative correlations between the endocrine disrupting compounds and the semen quality parameters could indicate that endocrine disrupting compounds could cause reproductive problems by decreasing the semen count and quality. This research will have helped to evaluate human exposure to endocrine disrupting compounds.

Effects of Prenatal Exposure to Phthalates

ERIC Educational Resources Information Center

Johnson, Laurie A.

2012-01-01

The purpose of this review of literature is to examine the association of phthalate exposure with development. Phthalates are chemical compounds used in poly-vinyl chloride, PVC; vinyl flooring, cosmetics, shampoo, air fresheners, soft plastic items, intravenous tubing, food packaging and wraps, textiles, paints, cleaning products and detergents.…

40 CFR 721.3085 - Brominated phthalate ester.

Code of Federal Regulations, 2010 CFR

2010-07-01

... information, and any information on methods for protecting against such risk, into a MSDS as described in... Section 721.3085 Protection of Environment ENVIRONMENTAL PROTECTION AGENCY (CONTINUED) TOXIC SUBSTANCES... substance is any manner or method of manufacture, import, or processing associated with any use of these...

Occurrence and Residue Pattern of Phthalate Esters in Fresh Tea Leaves and during Tea Manufacturing and Brewing.

PubMed

Liu, Pingxiang; Chen, Hongping; Gao, Guanwei; Hao, Zhenxia; Wang, Chen; Ma, Guicen; Chai, Yunfeng; Zhang, Lin; Liu, Xin

2016-11-23

The residues of 16 phthalate esters (PAEs) in fresh tea leaves and made tea were determined via gas chromatography-tandem mass spectrometry to study their distribution and degradation characteristics during tea planting and processing. Five PAEs were detected in all fresh tea leaves, and higher concentrations were detected in mature leaves. The distribution of PAEs in fresh tea leaves ranged from 69.7 to 2244.0 μg/kg. The degradative percentages of ∑ 5 PAEs during green tea manufacturing ranged from 61 to 63% and were significantly influenced by the drying process. The transfer rates of PAEs-D 4 ranged from 5.2 to 100.6%. PAEs with a high water solubility showed the highest transfer coefficient in the range of 91.8-100.6%, whereas PAEs with a high log K ow showed a low leaching efficiency below 11.9%. These results benefit the risk evaluation and establishment of a maximum residue limit for PAEs in tea.

Indoor phthalate concentration in residential apartments in Chongqing, China: Implications for preschool children's exposure and risk assessment

NASA Astrophysics Data System (ADS)

Bu, Zhongming; Zhang, Yinping; Mmereki, Daniel; Yu, Wei; Li, Baizhan

2016-02-01

Six phthalates - dimethyl phthalate (DMP), diethyl phthalate (DEP), di(isobutyl) phthalate (DiBP), di(n-butyl) phthalate (DnBP), butyl benzyl phthalate (BBzP) and di(2-ethylhexyl) phthalate (DEHP) - in indoor gas-phase and dust samples were measured in thirty residential apartments for the first time in Chongqing, China. Monte-Carlo simulation was used to estimate preschool children's exposure via inhalation, non-dietary ingestion and dermal absorption based on gas-phase and dust concentrations. Risk assessment was evaluated by comparing the modeled exposure doses with child-specific benchmarks specified in California's Proposition 65. The detection frequency for all the targeted phthalates was more than 80% except for BBzP. DMP was the most predominant compound in the gas-phase (median = 0.91 μg/m3 and 0.82 μg/m3 in living rooms and bedrooms, respectively), and DEHP was the most predominant compound in the dust samples (median = 1543 μg/g and 1450 μg/g in living rooms and bedrooms, respectively). Correlation analysis suggests that indoor DiBP and DnBP might come from the same emission sources. The simulations showed that the median DEHP daily intake was 3.18-4.28 μg/day/kg-bw in all age groups, suggesting that it was the greatest of the targeted phthalates. The risk assessment indicated that the exposure doses of DnBP and DEHP exceeded the child-specific benchmarks in more than 90% of preschool children in Chongqing. Therefore, from a children's health perspective, efforts should focus on controlling indoor phthalate concentrations and exposures.

Phthalate and PAH concentrations in dust collected from Danish homes and daycare centers

NASA Astrophysics Data System (ADS)

Langer, Sarka; Weschler, Charles J.; Fischer, Andreas; Bekö, Gabriel; Toftum, Jørn; Clausen, Geo

2010-06-01

As part of the Danish Indoor Environment and Children's Health (IECH) study, dust samples were collected from 500 bedrooms and 151 daycare centers of children (ages 3 to 5) living on the island of Fyn. The present paper reports results from the analyses of these samples for five phthalate esters (diethyl phthalate (DEP), di(n-butyl) phthalate (DnBP), di(isobutyl) phthalate (DiBP), butyl benzyl phthalate (BBzP), di(2-ethylhexyl) phthalate (DEHP)) and three PAHs (pyrene, benz[a]anthracene (B[a]A) and benzo[a]pyrene (B[a]P)). The three PAHs and DEHP were detected in dust samples from all sites, while DEP, DnBP, DiBP and BBzP were detected in more than 75% of the bedrooms and more than 90% of the daycare centers. The dust mass-fractions of both phthalates and PAHs were log-normally distributed. With the exception of DEP, the mass-fractions of phthalates in dust were higher in daycare centers than homes; PAH mass-fractions in dust were similar in the two locations. There was no correlation among the different phthalates in either homes or daycare centers. In contrast, the PAH were correlated with one another - more strongly so in homes ( R2 = 0.80-0.90) than in daycare centers ( R2 = 0.28-0.45). The dust levels of several phthalates (BBzP, DnBP and DEHP) were substantially lower than those measured in a comparable study conducted 6-7 years earlier in Sweden. Although usage patterns in Denmark differ from those in Sweden, the current results may also reflect a change in the plasticizers that are used in common products including toys. PAH levels were roughly an order of magnitude lower than those measured in Berlin and Cape Cod residences, suggesting that the Danish sites are less impacted by motor vehicle emissions.

In Utero Phthalate Effects in the Female Rat: A Model for MRKH Syndrome

EPA Science Inventory

Mayer-Rokitansky-Kuster-Hauser (MRKH) syndrome is characterized by uterine and vaginal canal aplasia in normal karyotype human females and is a syndrome with poorly define etiology. Reproductive toxicity of phthlate esters (PEs) occurs in rat offspring exposed in utero. a phenome...

Reliable quantification of phthalates in environmental matrices (air, water, sludge, sediment and soil): a review.

PubMed

Net, Sopheak; Delmont, Anne; Sempéré, Richard; Paluselli, Andrea; Ouddane, Baghdad

2015-05-15

Because of their widespread application, phthalates or phthalic acid esters (PAEs) are ubiquitous in the environment. Their presence has attracted considerable attention due to their potential impacts on ecosystem functioning and on public health, so their quantification has become a necessity. Various extraction procedures as well as gas/liquid chromatography and mass spectrometry detection techniques are found as suitable for reliable detection of such compounds. However, PAEs are ubiquitous in the laboratory environment including ambient air, reagents, sampling equipment, and various analytical devices, that induces difficult analysis of real samples with a low PAE background. Therefore, accurate PAE analysis in environmental matrices is a challenging task. This paper reviews the extensive literature data on the techniques for PAE quantification in natural media. Sampling, sample extraction/pretreatment and detection for quantifying PAEs in different environmental matrices (air, water, sludge, sediment and soil) have been reviewed and compared. The concept of "green analytical chemistry" for PAE determination is also discussed. Moreover useful information about the material preparation and the procedures of quality control and quality assurance are presented to overcome the problem of sample contamination and these encountered due to matrix effects in order to avoid overestimating PAE concentrations in the environment. Copyright © 2015 Elsevier B.V. All rights reserved.

BISPHENOL-A AND PHTHALATE ESTERS: POTENTIAL SOURCES OF RESIN COMPONENTS IN THE EVERYDAY ENVIRONMENTS OF PRESCHOOL CHILDREN

EPA Science Inventory

The Children's Total Exposure to Persistent Pesticides and Other Persistent Organic Pollutants (CTEPP) study examined the aggregate exposures of 257 preschool children to pollutants commonly found in their everyday environments. A primary objective of the CTEPP study was to ide...

The herbicide linuron reduces testosterone production from the fetal rat testis both in utero and in vitro

EPA Science Inventory

In utero exposure to linuron, an urea-based herbicide, results in a pattern of malformations of androgen-dependent tissues in adult male rat offspring resembling that produced by some phthalate esters which are known to decrease fetal testosterone production. This study investiga...

Investigation of the primary plasticisers present in polyvinyl chloride (PVC) products currently authorised as food contact materials.

PubMed

Carlos, Katherine S; de Jager, Lowri S; Begley, Timothy H

2018-03-15

PVC is a common food contact material that is usually plasticised to increase its flexibility. Phthalates are one class of chemical compounds that are often used as plasticisers in PVC in a wide range of industries. They may be used in packaging materials for foods and can also be found in components of certain food processing equipment such as conveyor belts and tubing. Transfer of plasticisers from packaging to foods can occur. In recent years, there has been increased interest in understanding the health effects of phthalates, as well as the possible human exposure levels. However, there is limited information available about the routes of exposure to phthalates. In July 2014, the Chronic Hazard Advisory Panel (CHAP) produced a report for the U.S. Consumer Product Safety Commission detailing the potential health hazards of phthalates and phthalate alternatives. This report listed diet as one factor contributing greater than or equal to 10% of total phthalate exposure. As a result of this report, the U.S. Food and Drug Administration (FDA) is interested in determining the types of the primary plasticiser present in food packaging and processing materials as well as their concentrations. An investigation was conducted of 56 different samples of PVC food packaging and food processing materials available in the US market using a solvent extraction and GC-MS analysis. Nine different plasticisers including three phthalates, di(2-ethylhexyl) phthalate, diisononyl phthalate and diisodecyl phthalate, were identified in the products tested. The plasticiser concentrations ranged from 1 to 53% depending on the types of food contact materials and the type of plasticiser. Overall, it appears that manufacturers are switching away from phthalates as their primary plasticiser to alternate compounds such as ESBO, ATBC, DEHT, DINCH, DEHA and DINA.

Urinary concentrations of cyclohexane-1,2-dicarboxylic acid monohydroxy isononyl ester, a metabolite of the non-phthalate plasticizer di(isononyl)cyclohexane-1,2-dicarboxylate (DINCH), and markers of ovarian response among women attending a fertility center

DOE Office of Scientific and Technical Information (OSTI.GOV)

Mínguez-Alarcón, Lidia, E-mail: lminguez@hsph.harv

Di(isononyl)cyclohexane-1,2-dicarboxylate (DINCH), a non-phthalate plasticizer, was introduced commercially in 2002 as an alternative to ortho-phthalate esters because of its favorable toxicological profile. However, the potential health effects from DINCH exposure remain largely unknown. We explored the associations between urinary concentrations of metabolites of DINCH on markers of ovarian response among women undergoing in vitro fertilization (IVF) treatments. Between 2011 and 2015, 113 women enrolled a prospective cohort study at the Massachusetts General Hospital Fertility Center and provided up to two urine samples prior to oocyte retrieval. The urinary concentrations of two DINCH metabolites, cyclohexane-1,2-dicarboxylic acid monohydroxy isononyl ester (MHiNCH) andmore » cyclohexane-1,2-dicarboxylic acid monocarboxyisooctyl ester (MCOCH), were quantified by isotope dilution tandem mass spectrometry. We used generalized linear mixed models to evaluate the association between urinary metabolite concentrations and markers of ovarian response, accounting for multiple IVF cycles per woman via random intercepts. On average, women with detectable urinary MHiNCH concentrations, as compared to those below LOD, had a lower estradiol levels (−325 pmol/l, p=0.09) and number of retrieved oocytes (−1.8, p=0.08), with a stronger association among older women. However, urinary MHiNCH concentrations were unrelated to mature oocyte yield and endometrial wall thickness. In conclusion, we found suggestive negative associations between urinary MHiNCH concentrations and peak estradiol levels and number of total oocyte yields. This is the first study evaluating the effect of DINCH exposure on human reproductive health and raises the need for further experimental and epidemiological studies to better understand the potential effects of this chemical on health. - Highlights: • Women with detectable urinary MHiNCH concentrations had a lower estradiol levels and number of retrieved oocytes. • The negative association between urinary MHiNCH concentrations and total oocyte yield was stronger in older women. • Urinary MHiNCH concentrations were unrelated to mature oocyte yield and endometrial wall thickness.« less

Kinetic evaluation and process performance of a fixed film bioreactor removing phthalic acid and dimethyl phthalate.

PubMed

Pirsaheb, Meghdad; Mesdaghinia, Ali-Reza; Shahtaheri, Seyed Jamaleddin; Zinatizadeh, Ali Akbar

2009-08-15

Phthalate esters are toxic organic contaminants which can enter into the environment through various industrial processes. In this study, a 6-liter fixed film bioreactor was used to examine biodegradation of phthalic acid (PA) and dimethyl phthalate (DMP) in synthetic wastewater. Effect on the process of two operating factors, namely hydraulic retention time (HRT) (at four levels ranging between 6 and 48 h) and initial phthalate concentrations (at six levels ranging from 10mg to 500 mg/l), was investigated. The process was stable at all operating conditions, except for the condition with influent PA and DMP of 500 mg/l and HRT of 6h. More than 95% removal efficiency was achieved for the conditions with HRT longer than 10h. Remarkable amount of DMP (398 mg/kg of sludge) was adsorbed on the biomass due to its higher hydrophobicity compared to PA (171 mg/kg). The kinetic parameters (mu(m,)K(s), Y and K(d)) were determined and compared for both substrates, PA and DMP.

Simple and rapid analysis of endocrine disruptors in liquid medicines and intravenous injection solutions by automated in-tube solid-phase microextraction/high performance liquid chromatography.

PubMed

Mitani, Kurie; Narimatsu, Shizuo; Izushi, Fumio; Kataoka, Hiroyuki

2003-07-14

A simple and rapid method was developed for analyzing contamination of endocrine disruptors in liquid medicines and intravenous injection solutions. Endocrine disrupting compounds such as bisphenol A (BPA), alkylphenols and phthalates were quantitated by on-line in-tube solid-phase microextraction coupled with high performance liquid chromatography (in-tube SPME/HPLC) with UV detection. The liquid medicines and intravenous injection solutions could be used directly without any pretreatment, and the BPA, alkylphenols and phthalates in these solutions were automatically analyzed. The limits of quantification for these compounds were 1-10 ng/ml. Recoveries of these compounds spiked to the intravenous injection solutions was over 80%, except for some phthalates. Di-n-butyl phthalate (DBP) was detected at a concentration of 7-60 ng/ml in most intravenous injection solutions in plastic containers, but it was not detected in solutions in glass bottles. Diethyl phthalate, di-n-propyl phthalate, DBP and di-2-ethylhexyl phthalate (DEHP) were also detected in syrup, lotion and eye drops in plastic containers. On the other hand, BPA and alkylphenols were not detected at all in these solutions. DEHP contamination from an administration set increased when total vitamin formulation was added to the infusion solution. DEHP was easily leached from polyvinyl chloride tubing by polysorbate 80. The in-tube SPME/HPLC method is simple, rapid and automatic, and it provides a useful tool for the screening and determination of endocrine disruptor contamination in liquid medicines and intravenous injection solutions.

Highly sensitive surface enhanced Raman scattering substrates based on Ag decorated Si nanocone arrays and their application in trace dimethyl phthalate detection

NASA Astrophysics Data System (ADS)

Zuo, Zewen; Zhu, Kai; Ning, Lixin; Cui, Guanglei; Qu, Jun; Cheng, Ying; Wang, Junzhuan; Shi, Yi; Xu, Dongsheng; Xin, Yu

2015-01-01

Wafer-scale three-dimensional (3D) surface enhancement Raman scattering (SERS) substrates were prepared using the plasma etching and ion sputtering methods that are completely compatible with well-established silicon device technologies. The substrates are highly sensitive with excellent uniformity and reproducibility, exhibiting an enhancement factor up to 1012 with a very low relative standard deviation (RSD) around 5%. These are attributed mainly to the uniform-distributed, multiple-type high-density hot spots originating from the structural characteristics of Ag nanoparticles (NPs) decorated Si nanocone (NC) arrays. We demonstrate that the trace dimethyl phthalate (DMP) at a concentration of 10-7 M can be well detected using this SERS substrate, showing that the AgNPs-decorated SiNC arrays can serve as efficient SERS substrates for phthalate acid esters (PAEs) detection with high sensitivity.

Parental contributions to early embryo development: influences of urinary phthalate and phthalate alternatives among couples undergoing IVF treatment.

PubMed

Wu, Haotian; Ashcraft, Lisa; Whitcomb, Brian W; Rahil, Tayyab; Tougias, Ellen; Sites, Cynthia K; Pilsner, J Richard

2017-01-01

Are preconception urinary concentrations of phthalates and phthalate alternatives associated with diminished early stage embryo quality in couples undergoing IVF? Male, but not female, urinary concentrations of select metabolites of phthalates and phthalate alternatives are associated with diminished blastocyst quality. Although phthalates are endocrine disrupting compounds associated with adverse reproductive health, they are in widespread use across the world. Male and female preconception exposures to select phthalates have been previously associated with adverse reproductive outcomes in both the general population and in those undergoing IVF. This prospective cohort included 50 subfertile couples undergoing IVF in western Massachusetts. This study includes the first 50 couples recruited from the Baystate Medical Center's Fertility Center in Springfield, MA, as part of the Sperm Environmental Epigenetics and Development Study (SEEDS). Relevant data from both partners, including embryo quality at the cleavage (Day 3) and blastocyst (Day 5) stages, were collected by clinic personnel during the normal course of an IVF cycle. A spot urine sample was collected from both male and female partners on the same day as semen sample procurement and oocyte retrieval. Concentrations of 17 urinary metabolite were quantified by liquid chromatography mass spectrometry and normalized via specific gravity. Generalized estimating equations were used to estimate odds ratios (OR) and 95% CI, with urinary phthalates and phthalate alternatives fitted as continuous variables and embryo quality as a binary variable. The 50 couples contributed 761 oocytes, of which 423 progressed to the cleavage stage, 261 were high-quality cleavage stage embryos, 137 were transferrable quality blastocysts and 47 were high-quality blastocysts. At the cleavage stage, male urinary monoethyl phthalate concentrations were positively associated with high-quality cleavage stage embryos (OR = 1.20, 95% CI 1.01-1.43, P = 0.04); no other significant associations were observed at this stage. At the blastocyst stage, male urinary concentrations of monobenzyl phthalate (OR = 0.55, 95% CI 0.36-0.84, P = 0.01), mono-3-hydroxybutyl phthalate (OR = 0.37, 95% CI 0.18-0.76, P = 0.01), mono-n-butyl phthalate (OR = 0.55, 95% CI 0.42-0.73, P < 0.01) and monomethyl phthalate (OR = 0.39, 95% CI 0.26-0.60, P < 0.01) were inversely associated with high-quality blastocysts. A borderline statistically significant relationship was observed for male concentrations of mono(2-ethylhexyl) phthalate (OR = 0.52, 95% CI 0.27-1.00, P = 0.05) and cyclohexane-1,2-dicarboxylic acid-monocarboxy isooctyl ester (OR = 0.21, 95% CI 0.04-1.03, P = 0.05) at the blastocyst stage. Similar inverse associations were observed between male urinary phthalate metabolite concentrations and likelihood of transferrable quality blastocysts. For female partners, select metabolites were positively associated with odds of high or transferrable blastocyst quality, but the observed associations were not consistent across blastocyst quality measures or between sex-specific and couples-level models. All models were adjusted for age of both partners, urinary metabolite concentrations of female partners and male infertility status, while models of blastocysts were additionally adjusted for embryo quality at cleavage stage. Our modest sample included only 50 couples contributing one cycle each. In addition, non-differential misclassification of exposure remains a concern given the single-spot urine collection and the short half-life of phthalates. Our results suggest an inverse association between male preconception concentrations of select phthalate metabolites and blastocyst quality, likely occurring after genomic activation. If corroborated with other studies, such findings will have public health and clinical significance for both the general population and those undergoing IVF. This work was generously supported by grant K22-ES023085 from the National Institute of Environmental Health Sciences. The authors declare no competing interests. N/A. © The Author 2016. Published by Oxford University Press on behalf of the European Society of Human Reproduction and Embryology. All rights reserved. For Permissions, please email: journals.permissions@oup.com.

Survey of phthalates, alkylphenols, bisphenol A and herbicides in Spanish source waters intended for bottling.

PubMed

Bono-Blay, Francisco; Guart, Albert; de la Fuente, Boris; Pedemonte, Marta; Pastor, Maria Cinta; Borrell, Antonio; Lacorte, Silvia

2012-09-01

Groundwaters and source waters are exposed to environmental pollution due to agricultural and industrial activities that can enhance the leaching of organic contaminants. Pesticides are among the most widely studied compounds in groundwater, but little information is available on the presence of phthalates, alkylphenols and bisphenol A. These compounds are used in pesticide formulations and represent an emerging family of contaminants due to their widespread environmental presence and endocrine-disrupting properties. Knowledge on the occurrence of contaminants in source waters intended for bottling is important for sanitary and regulatory purposes. So the aim of the present study was to evaluate the presence of phthalates, alkylphenols, triazines, chloroacetamides and bisphenol A throughout 131 Spanish water sources intended for bottling. Waters studied were spring waters and boreholes which have a protection diameter to minimize environmental contamination. Waters were solid-phase extracted (SPE) and analysed by gas chromatography coupled to mass spectrometry (GC-MS). Quality control analysis comprising recovery studies, blank analysis and limits of detection were performed. Using SPE and GC-MS, the 21 target compounds were satisfactorily recovered (77-124 %) and limits of quantification were between 0.0004 and 0.029 μg/L for pesticides, while for alkylphenols, bisphenol A and phthalates the limits of quantification were from 0.0018 μg/L for octylphenol to 0.970 μg/L for bis(2-ethylhexyl) phthalate. Among the 21 compounds analysed, only 9 were detected at levels between 0.002 and 1.115 μg/L. Compounds identified were triazine herbicides, alkylphenols, bisphenol A and two phthalates. Spring waters or shallow boreholes were the sites more vulnerable to contaminants. Eighty-five percent of the samples did not contain any of the target compounds. Target compounds were detected in a very low concentration and only in very few samples. This indicates the good quality of source waters intended for bottling and the effectiveness of the protection measures adopted in Spain. None of the samples analysed exceeded the maximum legislated levels for drinking water both in Spain and in the European Union.

Occurrence of phthalates in aquatic environment and their removal during wastewater treatment processes: a review.

PubMed

Gani, Khalid Muzamil; Tyagi, Vinay Kumar; Kazmi, Absar Ahmad

2017-07-01

Phthalates are plasticizers and are concerned environmental endocrine-disrupting compounds. Due to their extensive usage in plastic manufacturing and personal care products as well as the potential to leach out from these products, phthalates have been detected in various aquatic environments including drinking water, groundwater, surface water, and wastewater. The primary source of their environmental occurrence is the discharge of phthalate-laden wastewater and sludge. This review focuses on recent knowledge on the occurrence of phthalate in different aquatic environments and their fate in conventional and advanced wastewater treatment processes. This review also summarizes recent advances in biological removal and degradation mechanisms of phthalates, identifies knowledge gaps, and suggests future research directions.

Endocrine Disruptors and Asthma-Associated Chemicals in Consumer Products

PubMed Central

Nishioka, Marcia; Standley, Laurel J.; Perovich, Laura J.; Brody, Julia Green; Rudel, Ruthann A.

2012-01-01

Background: Laboratory and human studies raise concerns about endocrine disruption and asthma resulting from exposure to chemicals in consumer products. Limited labeling or testing information is available to evaluate products as exposure sources. Objectives: We analytically quantified endocrine disruptors and asthma-related chemicals in a range of cosmetics, personal care products, cleaners, sunscreens, and vinyl products. We also evaluated whether product labels provide information that can be used to select products without these chemicals. Methods: We selected 213 commercial products representing 50 product types. We tested 42 composited samples of high-market-share products, and we tested 43 alternative products identified using criteria expected to minimize target compounds. Analytes included parabens, phthalates, bisphenol A (BPA), triclosan, ethanolamines, alkylphenols, fragrances, glycol ethers, cyclosiloxanes, and ultraviolet (UV) filters. Results: We detected 55 compounds, indicating a wide range of exposures from common products. Vinyl products contained > 10% bis(2-ethylhexyl) phthalate (DEHP) and could be an important source of DEHP in homes. In other products, the highest concentrations and numbers of detects were in the fragranced products (e.g., perfume, air fresheners, and dryer sheets) and in sunscreens. Some products that did not contain the well-known endocrine-disrupting phthalates contained other less-studied phthalates (dicyclohexyl phthalate, diisononyl phthalate, and di-n-propyl phthalate; also endocrine-disrupting compounds), suggesting a substitution. Many detected chemicals were not listed on product labels. Conclusions: Common products contain complex mixtures of EDCs and asthma-related compounds. Toxicological studies of these mixtures are needed to understand their biological activity. Regarding epidemiology, our findings raise concern about potential confounding from co-occurring chemicals and misclassification due to variability in product composition. Consumers should be able to avoid some target chemicals—synthetic fragrances, BPA, and regulated active ingredients—using purchasing criteria. More complete product labeling would enable consumers to avoid the rest of the target chemicals. PMID:22398195

Assessing the concentration of phthalate esters (PAEs) and bisphenol A (BPA) and the genotoxic potential of treated wastewater (final effluent) in Saudi Arabia.

PubMed

Al-Saleh, Iman; Elkhatib, Rola; Al-Rajoudi, Tahreer; Al-Qudaihi, Ghofran

2017-02-01

Plasticizers such as phthalate esters (PAEs) and bisphenol A (BPA) are highly persistent organic pollutants that tend to bio-accumulate in humans through the soil-plant-animal food chain. Some studies have reported the potential carcinogenic and teratogenic effects in addition to their estrogenic activities. Water resources are scarce in Saudi Arabia, and several wastewater treatment plants (WTPs) have been constructed for agricultural and industrial use. This study was designed to: (1) measure the concentrations of BPA and six PAEs, dimethyl phthalate (DMP), diethyl phthalate (DEP), dibutyl phthalate (DBP), butyl benzyl phthalate (BBP), bis (2-ethylhexyl) phthalate (DEHP) and dioctyl phthalate (DOP), in secondary- and tertiary-treated wastewater collected from five WTPs in three Saudi cities for four to five weeks and (2) test their potential genotoxicity. Three genotoxicological parameters were used: % tail DNA (%T), tail moment (TM) and percentage micronuclei (%MN). Both DBP and DEHP were detected in all treated wastewater samples. DMP, DEP, BBP, DOP, and BPA were found in 83.3, 84.2, 79, 73.7 and 97.4% of the samples, respectively. The levels of DMP (p<0.001), DOP (p<0.001) and BPA (p=0.001) were higher in tertiary- treated wastewater than secondary-treated wastewater, perhaps due to the influence of the molecular weight and polarity of the chemicals. Both weekly sampling frequency and WTP locations significantly affected the variability in our data. Treated wastewater from Wadi Al-Araj was able to induce DNA damage (%T and TM) in human lymphoblastoid TK6 cells that was statistically higher than wastewater from all other WTPs and in untreated TK6 cells (negative control). %MN in samples from both Wadi Al-Araj and Manfouah did not differ statistically but was significantly higher than in the untreated TK6 cells. This study also showed that the samples of tertiary-treated wastewater had a higher genotoxicological potential to induce DNA damage than the samples of secondary-treated wastewater. BPA and some PAEs in the treated wastewater might have the potential to induce genetic damage, despite their low levels. Genotoxicity, however, may also have been due to the presence of other contaminants. Our preliminary findings should be of concern to Saudi agriculture because long-term irrigation with treated wastewater could lead to the accumulation of PAEs and BPA in the soil and ultimately reach the human and animal food chain. WTPs need to remove pollutants more efficiently. Until then, a cautious use of treated wastewater for irrigation is recommended to avoid serious health impacts on local populations. Copyright © 2016 Elsevier B.V. All rights reserved.

Biodegradation of di-n-butyl phthalate (DBP) by a novel endophytic Bacillus megaterium strain YJB3.

PubMed

Feng, Nai-Xian; Yu, Jiao; Mo, Ce-Hui; Zhao, Hai-Ming; Li, Yan-Wen; Wu, Bing-Xiao; Cai, Quan-Ying; Li, Hui; Zhou, Dong-Mei; Wong, Ming-Hung

2018-03-01

Phthalic acid esters (PAEs) are a group of recalcitrant and hazardous organic compounds that pose a great threat to both ecosystem and human beings. A novel endophytic strain YJB3 that could utilize a wide range of PAEs as the sole carbon and energy sources for cell growth was isolated from Canna indica root tissue. It was identified as Bacillus megaterium based on morphological characteristics and 16S rDNA sequence homology analysis. The degradation capability of the strain YJB3 was investigated by incubation in mineral salt medium containing di-n-butyl-phthalate (DBP), one of important PAEs under different environmental conditions, showing 82.5% of the DBP removal in 5days of incubation under the optimum conditions (acetate 1.2g·L -1 , inocula 1.8%, and temperature 34.2°C) achieved by two-step sequential optimization technologies. The DBP metabolites including mono-butyl phthalate (MBP), phthalic acid (PA), protocatechuic acid (PCA), etc. were determined by GC-MS. The PCA catabolic genes responsible for the aromatic ring cleavage of PCA in the strain YJB3 were excavated by whole-genome sequencing. Thus, a degradation pathway of DBP by the strain YJB3 was proposed that MBP was formed, followed by PA, and then the intermediates were further utilized till complete degradation. To our knowledge, this is the first study to show the biodegradation of PAEs using endophyte. The results in the present study suggest that the strain YJB3 is greatly promising to act as a competent inoculum in removal of PAEs in both soils and crops. Copyright © 2017 Elsevier B.V. All rights reserved.

Iron-based magnetic molecular imprinted polymers and their application in removal and determination of di-n-pentyl phthalate in aqueous media

PubMed Central

Zhou, Qingxiang; Yuan, Yongyong; Wu, Yalin

2017-01-01

Iron-based magnetic molecular imprinted polymers (Fe@SiO2@MIP) were synthesized for highly selective removal and recognition of di-n-pentyl phthalate (DnPP) from water. Well-defined core-shell Fe@SiO2 nanoparticles (less than 70 nm) were decorated on MIPs reticular layers to endow DnPP-MIPs with magnetic property for the first time. Five other phthalic acid esters including dimethyl phthalate, diethyl phthalate, dipropyl phthalate, di-n-butyl phthalate and di-iso-octyl phthalate were used to investigate the adsorptive selectivity to DnPP. The designed experiments were carried out to explore the adsorption kinetics, isotherms and thermodynamics and the results demonstrated that the adsorption was a spontaneous, exothermal and physical adsorption process. The materials were proved to be excellent adsorbents in removal of DnPP with an adsorption capacity as high as 194.15 mg g−1 in optimal condition. Furthermore, a magnetic solid phase extraction with Fe@SiO2@MIP coupled to high-performance liquid chromatography method was successfully developed for the determination of DnPP, and the proposed method achieved a good linear range of 0.5–250 µg l−1 with a correlation coefficient (R2) of 0.999 and low limit of detection (LOD) of 0.31 µg l−1. These materials exhibited excellent capacity in removal and highly sensitive identification of DnPP from aqueous environment samples, and opened a valuable direction for developing new adsorbents for the removal and enrichment of important pollutants. PMID:28879009

Iron-based magnetic molecular imprinted polymers and their application in removal and determination of di-n-pentyl phthalate in aqueous media.

PubMed

Li, Jing; Zhou, Qingxiang; Yuan, Yongyong; Wu, Yalin

2017-08-01

Iron-based magnetic molecular imprinted polymers (Fe@SiO 2 @MIP) were synthesized for highly selective removal and recognition of di- n -pentyl phthalate (DnPP) from water. Well-defined core-shell Fe@SiO 2 nanoparticles (less than 70 nm) were decorated on MIPs reticular layers to endow DnPP-MIPs with magnetic property for the first time. Five other phthalic acid esters including dimethyl phthalate, diethyl phthalate, dipropyl phthalate, di- n -butyl phthalate and di-iso-octyl phthalate were used to investigate the adsorptive selectivity to DnPP. The designed experiments were carried out to explore the adsorption kinetics, isotherms and thermodynamics and the results demonstrated that the adsorption was a spontaneous, exothermal and physical adsorption process. The materials were proved to be excellent adsorbents in removal of DnPP with an adsorption capacity as high as 194.15 mg g -1 in optimal condition. Furthermore, a magnetic solid phase extraction with Fe@SiO 2 @MIP coupled to high-performance liquid chromatography method was successfully developed for the determination of DnPP, and the proposed method achieved a good linear range of 0.5-250 µg l -1 with a correlation coefficient ( R 2 ) of 0.999 and low limit of detection (LOD) of 0.31 µg l -1 . These materials exhibited excellent capacity in removal and highly sensitive identification of DnPP from aqueous environment samples, and opened a valuable direction for developing new adsorbents for the removal and enrichment of important pollutants.

Phthalate induced toxicity in prostate cancer cell lines and effects of alpha lipoic acid.

PubMed

Kismali, G; Yurdakok-Dikmen, B; Kuzukiran, O; Arslan, P; Filazi, A

2017-01-01

The effects of dimethyl phthalate, diethyl phthalate, diisobutyl phthalate, di-n-butyl phthalate, benzylbutyl phthalate, di-2-ethylhexyl phthalate were investigated on human prostate cancer cell lines DU145 and PC3 in vitro. Standards of dimethyl phthalate, diethyl phthalate, di-isobutyl phthalate, dibutyl phthalate, benzyl butyl phthalate, and di-ethyl hexyl phthalate were used. Alpha lipoic acid was used as antioxidant compound. DU145 and PC3 human prostate carcinoma cells were used. MTT assay were used for cytotoxicity assay. A low dose proliferative effect of phthalates in vitro was observed. With the hypothesis of the inhibition of aerobic glycolysis activity in cancer treatment, α-lipoic acid was applied to cells; where as a contrary to previous studies, no change in the cell proliferation was observed. In combination with ALA, at IC50 and lower doses, an increase of the cytotoxic effect was found for DIBP, DBP and BBP; while for DMP, DEP and DEHP, a decrease was observed for DU145 cells. In PC3 cells, a decrease was observed for DMP, DEP and DBPs; while no significant difference were observed for DEHP, DIBP and BBP. The present study demonstrates preliminary information regarding the low dose proliferative effects of phthalates in prostate cancer in vitro (Tab. 2, Fig. 2, Ref. 65).

Ultra-trace analysis of hormones, pharmaceutical substances, alkylphenols and phthalates in two French natural mineral waters.

PubMed

Dévier, Marie-Hélène; Le Menach, Karyn; Viglino, Liza; Di Gioia, Lodovico; Lachassagne, Patrick; Budzinski, Hélène

2013-01-15

The aim of this work was to investigate the potential presence of a broad range of organic compounds, such as hormones, alkylphenols, bisphenol A and phthalates, as well as pharmaceutical substances in two brands of bottled natural mineral waters (Evian and Volvic, Danone). The phthalates were determined by solid-phase microextraction coupled to gas chromatography-mass spectrometry (SPME-GC-MS) and the other compounds by liquid chromatography-tandem mass spectrometry (LC-MS/MS) or gas chromatography-mass spectrometry (GC-MS) after solid-phase extraction. The potential migration of alkylphenols, bisphenol A and phthalates from polyethylene terephthalate (PET) bottles was also investigated under standardized test conditions. Evian and Volvic natural mineral waters contain none of the around 120 targeted organic compounds. Traces of 3 pharmaceuticals (ketoprofen, salicylic acid, and caffeine), 3 alkylphenols (4-nonylphenol, 4-t-octylphenol, and 4-nonylphenol diethoxylate), and some phthalates including di(2-ethylhexyl)phthalate (DEHP) were detected in the samples, but they were also present in the procedural blanks at similar levels. The additional test procedures demonstrated that the few detected compounds originated from the background laboratory contamination. Analytical procedures have been designed both in the bottling factory and in the laboratory in order to investigate the sources of DEHP and to minimize to the maximum this unavoidable laboratory contamination. It was evidenced that no migration of the targeted compounds from bottles occurred under the test conditions. The results obtained in this study underline the complexity of reaching a reliable measure to qualify the contamination of a sample at ultra-trace level, in the field of very pure matrices. The analytical procedures involving glassware, equipment, hoods, and rooms specifically dedicated to trace analysis allowed us to reach reliable procedural limits of quantification at the ng/L level, by lowering the background laboratory contamination. Copyright © 2012 Elsevier B.V. All rights reserved.

Survey on plasticizers currently found in PVC toys on the Swiss market: Banned phthalates are only a minor concern.

PubMed

McCombie, Gregor; Biedermann, Sandra; Suter, Gaby; Biedermann, Maurus

2017-04-16

Plasticizers in toys are a recurring source of criticism and concern, as consumers feel they may endanger the health of their children. Most of the information available in literature concerns the presence or absence of certain phthalic acid ester plasticizers. Very little information can be found in the public domain with respect to the actually used plasticizers at a given time and place. In this paper, we present the plasticizer composition of 118 samples from 88 polyvinyl chloride toys found on the Swiss market in autumn 2015. Bis(2-ethylhexyl) terephthalate (DEHT) was by far the most frequent main plasticizer in the analyzed samples, which is a change when compared to the plasticizers found in toys and child care articles in 2007. Furthermore, the data show that the banned phthalates in toys are only a minor concern. The occurrence, however, is not evenly distributed between importers. If a toy is not designed to be sold on the European market by the manufacturer, it seems to be more likely to contain a banned phthalic acid ester.

Ashwagandha leaf derived withanone protects normal human cells against the toxicity of methoxyacetic acid, a major industrial metabolite.

PubMed

Priyandoko, Didik; Ishii, Tetsuro; Kaul, Sunil C; Wadhwa, Renu

2011-05-04

The present day lifestyle heavily depends on industrial chemicals in the form of agriculture, cosmetics, textiles and medical products. Since the toxicity of the industrial chemicals has been a concern to human health, the need for alternative non-toxic natural products or adjuvants that serve as antidotes are in high demand. We have investigated the effects of Ayurvedic herb Ashwagandha (Withania somnifera) leaf extract on methoxyacetic acid (MAA) induced toxicity. MAA is a major metabolite of ester phthalates that are commonly used in industry as gelling, viscosity and stabilizer reagents. We report that the MAA cause premature senescence of normal human cells by mechanisms that involve ROS generation, DNA and mitochondrial damage. Withanone protects cells from MAA-induced toxicity by suppressing the ROS levels, DNA and mitochondrial damage, and induction of cell defense signaling pathways including Nrf2 and proteasomal degradation. These findings warrant further basic and clinical studies that may promote the use of withanone as a health adjuvant in a variety of consumer products where the toxicity has been a concern because of the use of ester phthalates.

Determination of phthalate esters in distillates by ultrasound-vortex-assisted dispersive liquid-liquid micro-extraction (USVADLLME) coupled with gas chromatography/mass spectrometry.

PubMed

Montevecchi, Giuseppe; Masino, Francesca; Zanasi, Luca; Antonelli, Andrea

2017-04-15

A method for the extraction of phthalate esters (PAEs) by Ultrasound-Vortex-Assisted Dispersive Liquid-Liquid Micro-Extraction (USVADLLME) approach was optimised and applied for the first time to a historical series of brandies. These contaminants are widely spread in the environment as a consequence of about half century of use in different fields of applications. The concern about these substances and the recent legal restrictions of China in distillates import need a quick and sensitive method for their quantification. The proposed method, moreover, is environmentally oriented due to the disposal of micro-quantities of solvent required. In fact, sub-ppm-limits of detection were achieved with a solvent volume as low as 160μL. The analysed samples were within the legal limits, except for some very ancient brandies whose contamination was probably due to a PAEs concentration effect as a consequence of long ageing and for the use of plastic pipelines no more operative. Copyright © 2016 Elsevier Ltd. All rights reserved.

Chemical-quality reconnaissance of the water and surficial bed material in the Delaware River estuary and adjacent New Jersey tributaries, 1980-81

USGS Publications Warehouse

Hochreiter, Joseph J.

1982-01-01

This report presents chemical-quality data collected from May 1980 to January 1981 at several locations within the Delaware River estuary and selected New Jersey tributaries. Samples of surface water were analyzed Environmental Protection Agency ' priority pollutants, ' including acid extractable, base/neutral extractable and volatile organic compounds, in addition to selected dissolved inorganic constituents. Surficial bed material at selected locations was examined for trace metals, insecticides, polychlorinated biphenyls, and base/neutral extractable organic compounds. Trace levels (1-50 micrograms per liter) of purgeable organic compounds, particularly those associated with the occurrence of hydrocarbons, were found in about 60% of the water samples taken. DDT, DDD, DDE, PCB 's and chlordane are present in most surficial bed material samples. Diazinon was the only organophosphorous insecticide detected in the study (1.6 micrograms per kilogram at one location). High values for select trace metals in bed material were discovered at two locations. Of the 10 sites sampled, the surficial bed material containing the most contamination was found along one cross section of Raccoon Creek at Bridgeport. An additional analysis of Raccoon Creek revealed bed material containing toluene, oil and grease, and trace quantities of 15 base/neutral extractable organic compounds, including polynuclear aromatic hydrocarbons, phthalate esters, and chlorinated benzenes.

Protection of ornamental gold fish Carassius auratus against Aeromonas hydrophila by treating Ixora coccinea active principles.

PubMed

Anusha, Paulraj; Thangaviji, Vijayaragavan; Velmurugan, Subramanian; Michaelbabu, Mariavincent; Citarasu, Thavasimuthu

2014-02-01

Herbals such as Ixora coccinea, Daemia extensa and Tridax procumbens were selected to screen in vitro antibacterial and immunostimulant activity against the freshwater fish pathogen Aeromonas hydrophila using different organic polar and non-polar solvents. Initial screening results revealed that, ethyl acetate extracts and its purified fraction of I. coccinea was able to suppress the A. hydrophila strains at more than 15 mm of zone of inhibition and positive immunostimulant activity. The purified active fraction, which eluted from H40: EA60 mobile phase was structurally characterized by GC-MS analysis. Two compounds such as Diethyl Phthalate (1,2-Benzene dicarboxylic acid, monobutyl ester) and Dibutyl Phthalate were characterized using NIST database search. In order to study the in vivo immunostimulant influence of the compounds, the crude extracts (ICE) and purified fractions (ICF) were incorporated to the artificial diets at the concentration of 400 mg kg⁻¹ and fed to the ornamental gold fish Carassius auratus for 30 days. After termination of feeding experiment, they were challenged with highly virulent A. hydrophila AHV-1 which was isolated from infected gold fish and studied the survival, specific bacterial load reduction, serum biochemistry, haematology, immunology and histological parameters. The control diet fed fishes succumbed to death within five days at 100% mortality whereas ICE and ICF fed groups survived 60 and 80% respectively after 10 days. The diets also helped to decrease the Aeromonas load after challenge and significantly (P ≤ 0.01) improved the serum albumin, globulin and protein. The diets also helped to increase the RBC and haemoglobin level significantly (P ≤ 0.05) from the control group. Surprisingly the immunological parameters like phagocytic activity, serum bactericidal activity and lysozyme activity were significantly increased (P ≤ 0.001) in the experimental diets. Macrophages and erythrocytes were abundantly expressed in the treated groups and the present work concluded that, the Phthalate derivatives from I. coccinea helps to stimulate the immune system against A. hydrophila challenge in C. auratus. Copyright © 2013 Elsevier Ltd. All rights reserved.

Assessment of toxic metals and phthalates in children's toys and clays.

PubMed

Korfali, Samira I; Sabra, Rayan; Jurdi, Mey; Taleb, Robin I

2013-10-01

Toxic metals and phthalates are introduced in the manufacturing of plastic toys and modeling clays. In Lebanon, inexpensive plastic toys and modeling clays (sold in dollar stores) are affordable and popular, and there is no legislation to monitor or regulate such toys. This study aimed to assess the quality of inexpensive plastic toys and modeling clays imported in Lebanon. Metal concentrations in toys, namely, zinc [not detectable (ND) to 3,708 μg/g], copper (ND to 140), chromium (ND to 75 μg/g), tin (ND to 39 μg/g), and cadmium (Cd) (ND to 20 μg/g), were lower than the European Union (EU) Directive limits, whereas lead (ND to 258 μg/g) in 10% of samples and antimony (Sb) (ND to 195 μg/g) in 5% of samples were greater than the EU limits. In modeling clays, most of the metals were lower than the EU Directive limits except for Cd and arsenic (As). Cd was detected in 83% of samples, with a mean level of 9.1 μg/g, which is far greater than the EU Directive limit (1.9 μg/g). The As mean level of 4.5 μg/g was greater than the EU limit (4.0 μg/g) and was detected in 9% of samples. Phthalic acid esters (PAEs) were found in 60% of children's toys and 77% of modeling clays. Phthalic acid butyl ester had the highest-level PAE encountered and was ≤59.1 % in one type of clay. However, among children's toys, di(4-octyl) ester terephthalic acid was the highest encountered phthalate at a concentration of 25.7%. The community survey indicated that 82% of households purchase their toys from inexpensive shops and that only 17% of parents were aware of the health hazard of such toys. Consequently, an intervention plan was proposed for the provision of safe toys to children.

Occurrence of phthalate esters in water and sediment of urban lakes in a subtropical city, Guangzhou, South China.

PubMed

Zeng, Feng; Cui, Kunyan; Xie, Zhiyong; Liu, Min; Li, Yangjie; Lin, Yujun; Zeng, Zunxiang; Li, Fangbai

2008-04-01

Extensive use of phthalate esters (PAEs) in both industrial processes and consumer products has resulted in the ubiquitous presence of these chemicals in the environment. This study reports the first data on the concentrations of 16 phthalate esters (PAEs) in water and sediments of the urban lakes in Guangzhou City. PAEs were detected in all samples analyzed, mainly originating from urban stormwater runoff, atmospheric deposition, as well as untreated discharge of industrial wastewater and municipal sewage. The Sigma(16)PAEs concentrations in water and sediments ranged from 1.69 to 4.72 microg L(-1) and 2.27 to 74.94 microg g(-1)-dry weight (dw), with the mean concentrations of 2.91 microg L(-1) and 20.85 microg g(-1)-dw, respectively, which indicates that sediment is a significant sink for PAEs. Variability of the Sigma 16PAEs concentrations in water and sediment in the urban lakes was almost consistent. The spatial distribution of PAEs was site-specific. Of the 16 PAEs, DMP, DEP, DnBP, DiBP, DMPP, and DEHP were present in all water and sediment samples. DnBP was abundant in water (53.0-81.2%), while no single dominant congener was found in sediments. The abundances of DiBP were similar to those of DEHP, and DiBP and DEHP collectively accounted for 77.2-97.6% of the Sigma 16PAEs concentrations. Congener specific analysis confirmed that DnBP was a predictive indicator for the dissolved summation operator16 PAEs concentration (correlation coefficient r=0.968, p<0.01), and that DiBP was a predictive indicator for the sediment summation operator16 PAEs concentration (r=0.975, p<0.01). As compared to the results for other studies, the urban lakes of Guangzhou were moderately polluted by PAEs.

Association of PAEs with Precocious Puberty in Children: A Systematic Review and Meta-Analysis.

PubMed

Wen, Yi; Liu, Shu-Dan; Lei, Xun; Ling, Yu-Shuang; Luo, Yan; Liu, Qin

2015-12-01

Precocious puberty (PP) currently affects 1 in 5000 children and is 10 times more common in girls. Existing studies have tried to detect an association between phathalic acid esters (PAEs) and PP, but the results did not reach a consensus. To estimate the association between PAEs and children with PP based on current evidence. Databases including PubMed (1978 to March 2015), OVID (1946 to March 2015), Web of Science (1970 to March 2015), EBSCO (1976 to March 2015), CNKI (1979 to March 2015), WANFANG DATA (1987 to March 2015), CBM (1978 to March 2015) and CQVIP (1989 to March 2015) were searched to identify all case-control studies that determined the exposure and concentration of PAEs and their metabolites in children with PP. Meta-analysis of the pooled standard mean difference (SMD) and odds ratio (OR) with 95% confidence intervals (CI) were calculated. A total of 14 studies involving 2223 subjects were finally included. The pooled estimates showed that PP was associated with di-(2-ethylhexyl)-phthalate (DEHP) exposure (OR: 3.90, 95% CI: 2.77 to 5.49). Besides, the concentration of DEHP (SMD: 1.73, 95% CI: 0.54 to 2.91) and di-n-butyl phthalate (DBP) (SMD: 4.31, 95% CI: 2.67 to 5.95) in the PP group were significantly higher than those in the control group, respectively, while no difference was detected between case and control groups in either serum or urinary concentration of mono-(2-ethylhexyl)-phthalate (MEHP), monobutyl phthalate (MBP), mono(2-ethyl-5-oxohexyl) phthalate(MEOHP), mono-(2-ethyl-5-carboxypentyl) phthalate (MECPP), monomethyl phthalate (MMP), monobenzyl phthalate (MBzP) or monoethyl phthalate (MEP). Exposure of DEHP and DBP might be associated with PP risk for girls, however, there is no evidence to show an association between the exposure to most PAE metabolites and PP. Given the moderate strength of the results, well-designed cohort studies with large sample size should be performed in future.

Analytical study of endocrine-disrupting chemicals in leachate treatment process of municipal solid waste (MSW) landfill sites.

PubMed

Asakura, Hiroshi; Matsuto, Toshihiko; Tanaka, Nobutoshi

2007-01-01

Influent and processed water were sampled at different points in the leachate treatment facilities of five municipal solid waste (MSW) landfill sites. Then, the concentrations of endocrine-disrupting chemicals (EDCs), namely, alkylphenols (APs), bisphenol A (BPA), phthalic acid esters (PAEs) and organotin compounds (OTs), in the treated leachate samples were determined and the behavior of the EDCs in the treatment processes was discussed. The concentrations of APs were as low as those in surface waters, and no OTs were detected (detection limit: 0.01 microg/L). Meanwhile, diethylhexyl phthalate (DEHP), which was the most abundant of the four substances measured as PAEs, and BPA were found in all of the influent samples. BPA was considerably degraded by aeration, except when the water temperature was low and the total organic carbon (TOC) was high. By contrast, aeration, biological treatment, and coagulation/sedimentation removed only a small amount of DEHP.

An etiological study of phthalate self-contamination of spacecraft and contamination from their earthly environs

NASA Technical Reports Server (NTRS)

Gross, F. C.; Colony, J. A.

1972-01-01

Phthalates are very objectionable contaminants in space experiments because of their strong absorption in the UV and IR regions of the spectrum. Thus, even minute amounts of these compounds migrating to optical equipment, in test or space flight conditions, can seriously compromise the results of experiments by altering the sensitivity of the functional equipment. Volatility data of the phthalates and other plasticizers are presented in addition to UV spectra of ultrathin films of these same types of compounds. Sources of plasticizer contamination are revealed with special recognition given to di-2-ethylhexyl phthalate (DEHP), the single most ubiquitous plasticizer in use. A surprisingly large percentage of the outgassing condensates from vacuum testing of spacecraft contain DEHP as well as other plasticizers. IR and gas chromatography/mass spectroscopy methods were used to analyze samples from spacecraft. Methods for successful reduction of plasticizers and other contaminants are mentioned.

Toxicity effects of di-(2-ethylhexyl) phthalate to Eisenia fetida at enzyme, cellular and genetic levels

PubMed Central

Chen, Li’ke; Wu, Longhua; Christie, Peter; Zhang, Haibo; Luo, Yongming

2017-01-01

Di-(2-ethylhexyl) phthalate (DEHP) is a dominant phthalic acid ester (PAE) that has aroused public concern due to its resistance to degradation and its toxicity as an endocrine-disrupting compound. Effects of different concentrations of DEHP on Eisenia fetida in spiked natural soil have been studied in the body of the earthworm by means of soil cultivation tests 7, 14, 21 and 28 days after exposure. The results indicated that, in general, superoxide dismutase (SOD) activity, malondialdehyde (MDA) content, metallothionein (MT) content, the expression of heat shock protein 70 (HSP 70) and all the tested geno-toxicity parameters are promoted as time elapses and with increasing concentration of DEHP. However, peroxidase (POD) activity, neutral red retention time (NRRT) and mitochondrial membrane potential difference values were found to decrease even at a low concentration of DEHP of 1 mg kg-1 soil (p<0.05). Clear toxic effects of DEHP on E. fetida have been generally recognized by means of the disturbance of antioxidant enzyme activity/content and critical proteins, cell membrane and organelle disorder and DNA damage estimated by length of tail, tail DNA ratio, and tail moment parameters. A concentration of DEHP of 3 mg kg-1 may be recommended as a precaution against the potential risk of PAEs in soils and for indicating suitable threshold values for other soil animals and soil micro-organisms. PMID:28319143

Toxicity effects of di-(2-ethylhexyl) phthalate to Eisenia fetida at enzyme, cellular and genetic levels.

PubMed

Ma, Tingting; Zhou, Wei; Chen, Li'ke; Wu, Longhua; Christie, Peter; Zhang, Haibo; Luo, Yongming

2017-01-01

Di-(2-ethylhexyl) phthalate (DEHP) is a dominant phthalic acid ester (PAE) that has aroused public concern due to its resistance to degradation and its toxicity as an endocrine-disrupting compound. Effects of different concentrations of DEHP on Eisenia fetida in spiked natural soil have been studied in the body of the earthworm by means of soil cultivation tests 7, 14, 21 and 28 days after exposure. The results indicated that, in general, superoxide dismutase (SOD) activity, malondialdehyde (MDA) content, metallothionein (MT) content, the expression of heat shock protein 70 (HSP 70) and all the tested geno-toxicity parameters are promoted as time elapses and with increasing concentration of DEHP. However, peroxidase (POD) activity, neutral red retention time (NRRT) and mitochondrial membrane potential difference values were found to decrease even at a low concentration of DEHP of 1 mg kg-1 soil (p<0.05). Clear toxic effects of DEHP on E. fetida have been generally recognized by means of the disturbance of antioxidant enzyme activity/content and critical proteins, cell membrane and organelle disorder and DNA damage estimated by length of tail, tail DNA ratio, and tail moment parameters. A concentration of DEHP of 3 mg kg-1 may be recommended as a precaution against the potential risk of PAEs in soils and for indicating suitable threshold values for other soil animals and soil micro-organisms.

Qualitative Analysis of Additives in Plastic Marine Debris and Its New Products.

PubMed

Rani, Manviri; Shim, Won Joon; Han, Gi Myung; Jang, Mi; Al-Odaini, Najat Ahmed; Song, Young Kyong; Hong, Sang Hee

2015-10-01

Due to their formulation and/or processing, plastics contain additives and impurities that may leach out under conditions of use and accumulate in the environment. To evaluate their role as vectors of chemical contaminants in marine environment, plastic debris (n = 19) collected from coastal beaches along with new plastics (n = 25; same or same brand) bought from local markets were screened by gas chromatography-mass spectrometry in full scan mode. Detected peaks were identified using NIST library in different polymers (polypropylene (PP) > polyethylene (PE) > PP + PE > polyethyl terephthalate > poly(acylene:styrene) with different use (food, fishery, and general use). A database on the presence of 231 different chemicals were grouped into hydrocarbons, ultra-violet (UV)-stabilizers, antioxidants, plasticizers, lubricants, intermediates, compounds for dyes and inks, flame retardants, etc. The UV326, UV327, UV328, UV320, UvinualMC80, irganox 1076, DEHP, antioxidant no 33, di-n-octylisophthalate, diisooctyl phthalate, hexanoic acid 2-ethyl-hexadecyl ester, and hydrocarbons were most frequently detected. Finding of toxic phthalates and UV stabilizers in those products having moisture contact (like bottles with short use) raised concern to humans and indicated their irregular use. The comparison between new and debris plastics clearly indicated the leaching and absorption of chemicals and supports our assumption of plastic as media for transferring these additives in marine environment.

Phthalates and perfluorinated alkylated substances in Atlantic bluefin tuna (Thunnus thynnus) specimens from Mediterranean Sea (Sardinia, Italy): Levels and risks for human consumption.

PubMed

Guerranti, Cristiana; Cau, Alessandro; Renzi, Monia; Badini, Simone; Grazioli, Eleonora; Perra, Guido; Focardi, Silvano Ettore

2016-10-02

Atlantic blue fin tuna (Thunnus thynnus) is a species of great importance for Mediterranean Sea area, from both ecological and commercial points of view. The scientific literature reports few data on the contamination of this fish by emerging organic compounds such as perfluorinated alkylated substances(PFASs) and phthalates, being the latter never been studied in tuna. This study therefore investigated the presence of the PFASs perfluorooctane sulphonate (PFOS) and perfluoroctanoic acid (PFOA) and the phthalate di-2-ethylhexyl phthalate (DEHP), also monitored by its metabolite mono-2-ethylhexyl phthalate(MEHP), to assess both the state of contamination of Atlantic bluefin tuna specimen and the risk due to the toxicity of these compounds for human consumption. While PFOA was never found, detectable levels of PFOS (0.4-1.88 ng/g), DEHP (9-14.62 ng/g) and MEHP (1.5-6.30 ng/g) were found. The results were elaborated relating the accumulation to the size and age of the individuals and showed a correlation between the levels of different pollutants investigated.

Man is not a big rat: concerns with traditional human risk assessment of phthalates based on their anti-androgenic effects observed in the rat foetus.

PubMed

Habert, René; Livera, Gabriel; Rouiller-Fabre, Virginie

2014-01-01

Phthalates provide one of the most documented example evidencing how much we must be cautious when using the traditional paradigm based on extrapolation of experimental data from rodent studies for human health risk assessment of endocrine disruptors (EDs). Since foetal testis is known as one of the most sensitive targets of EDs, phthalate risk assessment is routinely based on the capacity of such compounds to decrease testosterone production by the testis or to impair masculinization in the rat during foetal life. In this paper, the well-established inhibiting effects of phthalates of the foetal Leydig cells function in the rat are briefly reviewed. Then, data obtained in humans and other species are carefully analysed. Already in January 2009, using the organotypic culture system named Fetal Testis Assay (FeTA) that we developed, we reported that phthalates might not affect testosterone production in human foetal testes. Several recent experimental studies using xenografts confirm the absence of detectable anti-androgenic effect of phthalates in the human foetal testes. Epidemiological studies led to contradictory results. Altogether, these findings suggest that phthalates effects on foetal Leydig cells are largely species-specific. Consequently, the phthalate threshold doses that disturb foetal steroidogenesis in rat testes and that are presently used to define the acceptable daily intake levels for human health protection must be questioned. This does not mean that phthalates are safe because these compounds have many deleterious effects upon germ cell development that may be common to the different studied species including human. More generally, the identification of common molecular, cellular or/and phenotypic targets in rat and human testes should precede the choice of the toxicological endpoint in rat to accurately assess the safety threshold of any ED in humans.

Removal of phthalates and pharmaceuticals from municipal wastewater by graphene adsorption process.

PubMed

Yang, Gordon C C; Tang, Pei-Ling

2016-01-01

In this work graphene was used for evaluation of its adsorption behavior and performance in removing phthalate esters and pharmaceuticals in municipal wastewater. Di-n-butyl phthalate (DnBP), di-(2-ethylhexyl) phthalate (DEHP), acetaminophen (ACE), caffeine (CAF), cephalexin (CLX), and sulfamethoxazole (SMX) were emerging contaminants (ECs) with detection frequencies over 92% in a one-year monitoring of the occurrence of ECs in influent samples of a sewage treatment plant in Taiwan. Thus, these ECs were selected as the target contaminants for removal by graphene adsorption process. Experimental results showed that the adsorption isotherm data were fitted well to Langmuir model equation. It was also found that the adsorption process obeyed the pseudo-second-order kinetics. A graphene dosage of 0.1 g/L and adsorption time of 12 h were found to be the optimal operating conditions for the ECs of concern in model solutions in a preliminary study. By using the determined optimal operating conditions for removal of such ECs in actual municipal wastewater, removal efficiencies for various ECs were obtained and given as follows: (1) DnBP, 89%, (2) DEHP, 86%, (3) ACE, 43%, (4) CAF, 84%, (5) CLX, 81%, and (6) SMX, 34%.

Plasmid-Encoded Phthalate Catabolic Pathway in Arthrobacter keyseri 12B†

PubMed Central

Eaton, Richard W.

2001-01-01

Several 2-substituted benzoates (including 2-trifluoromethyl-, 2-chloro-, 2-bromo-, 2-iodo-, 2-nitro-, 2-methoxy-, and 2-acetyl-benzoates) were converted by phthalate-grown Arthrobacter keyseri (formerly Micrococcus sp.) 12B to the corresponding 2-substituted 3,4-dihydroxybenzoates (protocatechuates). Because these products lack a carboxyl group at the 2 position, they were not substrates for the next enzyme of the phthalate catabolic pathway, 3,4-dihydroxyphthalate 2-decarboxylase, and accumulated. When these incubations were carried out in iron-containing minimal medium, the products formed colored chelates. This chromogenic response was subsequently used to identify recombinant Escherichia coli strains carrying genes encoding the responsible enzymes, phthalate 3,4-dioxygenase and 3,4-dihydroxy-3,4-dihydrophthalate dehydrogenase, from the 130-kbp plasmid pRE1 of strain 12B. Beginning with the initially cloned 8.14-kbp PstI fragment of pRE824 as a probe to identify recombinant plasmids carrying overlapping fragments, a DNA segment of 33.5 kbp was cloned from pRE1 on several plasmids and mapped using restriction endonucleases. From these plasmids, the sequence of 26,274 contiguous bp was determined. Sequenced DNA included several genetic units: tnpR, pcm operon, ptr genes, pehA, norA fragment, and pht operon, encoding a transposon resolvase, catabolism of protocatechuate (3,4-dihydroxybenzoate), a putative ATP-binding cassette transporter, a possible phthalate ester hydrolase, a fragment of a norfloxacin resistance-like transporter, and the conversion of phthalate to protocatechuate, respectively. Activities of the eight enzymes involved in the catabolism of phthalate through protocatechuate to pyruvate and oxaloacetate were demonstrated in cells or cell extracts of recombinant E. coli strains. PMID:11371533

Fate of four phthalate plasticizers under various wastewater treatment processes.

PubMed

Armstrong, Dana L; Rice, Clifford P; Ramirez, Mark; Torrents, Alba

2018-05-18

The fate of four phthalate plasticizers during wastewater treatment processes at six different wastewater treatment plants (WWTPs) was investigated. Concentrations of benzyl butyl phthalate (BBP), di(2-ethylhexyl) phthalate (DEHP), diisononyl phthalate (DiNP), and diisodecyl phthalate (DiDP) were determined prior to either aerobic or anaerobic (conventional and advanced) treatment, after treatment, and in final, dewatered solids. Despite their elevated use worldwide, the fate of DiNP and DiDP during wastewater treatment have not been well characterized. DEHP was readily degraded during aerobic treatments while anaerobic digestion resulted in either no significant change in concentrations or an increase in concentration, in the case of more advanced anaerobic processes (thermal hydrolysis pretreatment and a two-phase acid/gas process). Impacts of the various treatment systems on DiNP, DiDP, and BBP concentrations were more varied - anaerobic digestion led to significant decreases, increases, or no significant change for these compounds, depending on the treatment facility, while aerobic treatment was generally effective at degrading the compounds. Additionally, thermal hydrolysis pretreatment of sludge prior to anaerobic digestion resulted in increases in DiNP, DiDP, and BBP concentrations. The predicted environmental concentrations for all four compounds in soils after a single biosolids application were calculated and the risk quotients for DEHP in soils were determined. The estimated toxicity risk for DEHP in soils treated with a single application of sludge from any of the six studied WWTPs is lower than the level of concern for acute and chronic risk, as defined by the US EPA.

CHANGES IN FETAL TESTIS GENE EXPRESSION AND STEROID HORMONE SYNTHESIS INDUCED IN MALE OFFSPRING AFTER MATERNAL TREATMENT WITH PHTHALATE ESTERS

EPA Science Inventory

Targeted inactivation of the insulin-like hormone 3 (insl3) gene in male mice results in altered gubernacular development, disrupted testis decent, and cryptorchidism. Cryptorchidism is a fairly common human malformation, being displayed in 1-3% of males at birth. Since only a s...

Biodegradation of di-n-butyl phthalate by bacterial consortium LV-1 enriched from river sludge

PubMed Central

Li, Fangfang; Ruan, Xinling; Song, Jian; Lv, Lv; Chai, Liyuan; Yang, Zhihui; Luo, Lin

2017-01-01

A stable bacterial consortium (LV-1) capable of degrading di-n-butyl phthalate (DBP) was enriched from river sludge. Community analysis revealed that the main families of LV-1 are Brucellaceae (62.78%) and Sinobacteraceae (14.83%), and the main genera of LV-1 are Brucella spp. (62.78%) and Sinobacter spp. (14.83%). The optimal pH and temperature for LV-1 to degrade DBP were pH 6.0 and 30°C, respectively. Inoculum size influenced the degradation ratio when the incubation time was < 24 h. The initial concentration of DBP also influenced the degradation rates of DBP by LV-1, and the degradation rates ranged from 69.0–775.0 mg/l/d in the first 24 h. Degradation of DBP was best fitted by first-order kinetics when the initial concentration was < 300 mg/l. In addition, Cd2+, Cr6+, and Zn2+ inhibited DBP degradation by LV-1 at all considered concentrations, but low concentrations of Pb2+, Cu2+, and Mn2+ enhanced DBP degradation. The main intermediates (mono-ethyl phthalate [MEP], mono-butyl phthalate [MBP], and phthalic acid [PA]) were identified in the DBP degradation process, thus a new biochemical pathway of DBP degradation is proposed. Furthermore, LV-1 also degraded other phthalates with shorter ester chains (DMP, DEP, and PA). PMID:28542471

Migration of phthalates on culture plates - an important challenge to consider for in vitro studies.

PubMed

Frohnert Hansen, Juliana; Boas, Malene; Møller Brorson, Marianne; Frederiksen, Hanne; Hartoft-Nielsen, Marie-Louise; Krogh Rasmussen, Åse; Main, Katharina M; Feldt-Rasmussen, Ulla

2016-01-01

Phthalates are endocrine disruptors of the reproductive system and suspected to influence many other organ and hormone systems. They are also semi-volatile organic compounds present in the gas phase in the environment. Their mode of action has been investigated in numerous in vitro studies. Multi-well culture plates are typically used to study phthalates in cell cultures. In a pilot study, we observed evidence of phthalate migration in 24-well culture plates. As this has not previously been described, we investigated the phenomenon in more detail. Primary human thyroid epithelial cell cultures (n = 8 cultures) were exposed to either di-ethyl phthalate (DEP), di-n-butyl phthalate (DnBP), mono-n-butyl phthalate (MnBP) or di-(2-ethylhexyl) phthalate (DEHP). Measurement of phthalate metabolites by mass spectrometry demonstrated that the short-branched DEP was able to migrate to adjacent wells when added to cell culture plates. DnBP also seemed to be able to migrate, unlike the long-branched DEHP or the monoester MnBP which did not seem to have this ability. High background levels of phthalate metabolites were also observed, which might compromise results from low dose phthalate studies. In conclusion, the migration of phthalates which is probably caused by their volatile properties might lead to false interpretation of study results.

Emergent contaminants in the wastewater effluents of two highly populated tropical cities.

PubMed

Soler-Llavina, Sheila M; Ortiz-Zayas, Jorge R

2017-10-01

Exposure to the anthropogenic chemicals known as endocrine disrupting compounds (EDCs) may result in negative biological effects. Low levels of EDCs in the environment aggravate the problem as exposure is constant. Urban areas concentrate pollution as greater volumes are released from human activities. Water for public supply is particularly vulnerable as the sewage treatment facilities may not eliminate EDCs. The goal was to assess estrogenicity and effectiveness of removal of phthalates in primary and tertiary wastewater treatment facilities in urban cities in the tropical island of Puerto Rico. A yeast bioassay used to measure estrogenicity showed higher removal with tertiary treatment. However, results in the picomolar range suggest low doses of estrogenic compounds were being released to receiving waters. For the phthalates, solid phase extraction and gas chromatography-mass spectrometry analyses revealed removals ranging from 42.9% to 92.4% with tertiary treatment. More than 90% removal was achieved for benzylbutyl phthalate, dibutyl phthalate and bis-2-ethylhexyl phthalate. However, concentrations ranging from 0.86 to 1.29 ppm for the phthalates in the outflow were detected even at the tertiary waste water treatment plant effluent implying failure of EDC removal. These results can assist managers in evaluating pollution control technologies to ameliorate the impacts of EDCs in the tropics.

Exposure to phthalic acid, phthalate diesters and phthalate monoesters from foodstuffs: UK total diet study results.

PubMed

Bradley, Emma L; Burden, Richard A; Bentayeb, Karim; Driffield, Malcolm; Harmer, Nick; Mortimer, David N; Speck, Dennis R; Ticha, Jana; Castle, Laurence

2013-01-01

Phthalates are ubiquitous in the environment and thus exposure to these compounds can occur in various forms. Foods are one source of such exposure. There are only a limited number of studies that describe the levels of phthalates (diesters, monoesters and phthalic acid) in foods and assess the exposure from this source. In this study the levels of selected phthalate diesters, phthalate monoesters and phthalic acid in total diet study (TDS) samples are determined and the resulting exposure estimated. The methodology for the determination of phthalic acid and nine phthalate monoesters (mono-isopropyl phthalate, mono-n-butyl phthalate, mono-isobutyl phthalate, mono-benzyl phthalate, mono-cyclohexyl phthalate, mono-n-pentyl phthalate, mono-(2-ethylhexyl) phthalate, mono-n-octyl phthalate and mono-isononyl phthalate) in foods is described. In this method phthalate monoesters and phthalic acid are extracted from the foodstuffs with a mixture of acidified acetonitrile and dichloromethane. The method uses isotope-labelled phthalic acid and phthalate monoester internal standards and is appropriate for quantitative determination in the concentration range of 5-100 µg kg⁻¹. The method was validated in-house and its broad applicability demonstrated by the analysis of high-fat, high-carbohydrate and high-protein foodstuffs as well as combinations of all three major food constituents. The methodology used for 15 major phthalate diesters has been reported elsewhere. Phthalic acid was the most prevalent phthalate, being detected in 17 food groups. The highest concentration measured was di-(2-ethylhexyl) phthalate in fish (789 µg kg⁻¹). Low levels of mono-n-butyl phthalate and mono-(2-ethylhexyl) phthalate were detected in several of the TDS animal-based food groups and the highest concentrations measured corresponded with the most abundant diesters (di-n-butyl phthalate and di-(2-ethylhexyl) phthalate). The UK Committee on Toxicity of Chemicals in Food, Consumer Products and the Environment (COT) considered the levels found and concluded that they did not indicate a risk to human health from dietary exposure alone.

Phthalate metabolites in the European eel (Anguilla anguilla) from Mediterranean coastal lagoons.

PubMed

Fourgous, C; Chevreuil, M; Alliot, F; Amilhat, E; Faliex, E; Paris-Palacios, S; Teil, M J; Goutte, A

2016-11-01

The levels and fate of phthalate metabolites have been poorly evaluated in fish, despite their potential ecotoxicological impacts. The present study aims to characterize the levels of phthalate metabolites in muscle tissue of yellow eels (Anguilla anguilla) from two coastal Mediterranean lagoons, during three sampling periods. Nine phthalate metabolites were detected in >70% of the samples. Slightly higher levels of phthalate metabolites were detected in March and June compared to October, suggesting possible seasonal variations in environmental release and/or phthalate metabolization process by eels. The large sample size (N=117) made it possible to explore correlations between phthalate metabolites' levels and individual parameters, such as body length, age, body condition and hepatic histo-pathologies. Body length and estimated age poorly correlated with phthalate metabolites, suggesting that eels did not accumulate phthalates during growth, contrary to persistent compounds. Eels presented different grades of hepatic fibrosis and lipidosis. A negative correlation was found between the severity of these pathologies in the liver and the sum of phthalate metabolites levels, supporting the hypothesis that eels with damaged liver are less able to metabolize xenobiotics. Copyright © 2016 Elsevier B.V. All rights reserved.

Analysis of organic compounds' degradation and electricity generation in anaerobic fluidized bed microbial fuel cell for coking wastewater treatment.

PubMed

Liu, Xinmin; Wu, Jianjun; Guo, Qingjie

2017-12-01

A single-chambered packing-type anaerobic fluidized microbial fuel cell (AFBMFC) with coking wastewater (CWW) as fuel was built to treat CWW, which not only has high treating efficiency, but also can convert organic matter in wastewater into electricity. AFBMFC was constructed by using anaerobic sludge that was domesticated as inoculation sludge, which was used to biochemically treat CWW. The organic compounds in CWW were extracted by liquid-liquid extraction step by step every day. The extraction phase was concentrated by a rotary evaporator and a nitrogen sweeping device and was analyzed by GC-MS. And the electricity-generation performances of AFBMFC were investigated. The results show that the composition of CWW was complicated, which mainly contains hydrocarbons, phenols, nitrogenous organic compounds, alcohols and aldehydes, esters and acids and so on. After a cycle of anaerobic biochemical treatment, the content of organic compounds in the effluent decreased significantly. After the treatment of AFBMFC, 99.9% phenols, 98.4% alcohol and aldehydes and 95.3% nitrogenous compounds were biodegraded. In the effluent, some new compounds (such as tricosane and dibutyl phthalate) were produced. The chemical oxygen demand (COD) of CWW decreased from 3372 to 559 mg/L in the closed-circuit microbial fuel cell, and the COD removal was 83.4 ± 1.0%. The maximum power density of AFBMFC was 2.13 ± 0.01 mW m -2 .

Structural characteristics of biochar-graphene nanosheet composites and their adsorption performance for phthalic acid esters

NASA Astrophysics Data System (ADS)

Ghaffar, Abdul; Zhu, Xiaoying; Chen, Baoliang

2017-04-01

The nonuniform and unhomogenous structure of biochar including defects could affect the adsorption performance of biochars. Biochar and graphene nanosheet (GNS) composites (BG) were prepared by simple dip coating method following thermal route of bamboo wood biomass at three different temperatures (300, 500, 700°C), in addition to biochars. The morphology and structural composition of biochars and BG composites were examined by scanning electron microscopy, transmission electron microscopy, Brunauer-Emmet-Teller surface area with N2 and CO2, Raman spectroscopy, Fourier Transformed Infrared spectroscopy, X-ray Photoelectron spectroscopy, Thermogravimetric analysis and CHN elemental analysis. It was found that GNS ( 1µm, 0.1% mass) provided higher thermal stability, porous structure, and relatively higher surface area (N2 and CO2), to BG composites. BG composites portrayed the existence of GNS bearing cavities and evidently increased the graphitic structure. The adsorption capabilities of biochars and BG composites towards dimethyl phthalate (DMP), diethyl phthalate (DEP), and dibutyl phthalate (DBP) as model phthalic acid esters (PAEs) were examined by batch sorption technique. The BG composites exhibited the increased adsorption capacity comparatively to biochars. The aromatic sheets of biochars and GNS on biochars dominated the π-π EDA (electron donor-acceptor) interaction for ring structure of DMP molecule in addition to pore-diffusion mechanism, whereas adsorption of DBP was attributed to hydrophobicity. Our results suggest that surface composition and morphology of biochars can be regulated with GNS and may enhance their adsorption capacity, thus could be considered for effective environmental remediation of various organic contaminants.

Effects of Potamogeton crispus L.-bacteria interactions on the removal of phthalate acid esters from surface water.

PubMed

Chi, Jie; Gao, Jing

2015-01-01

To investigate the mechanism of submerged macrophyte-bacteria interactions on the removal of phthalic acid esters from surface water, experiments with and without Potamogeton crispus L. were performed. A two-compartment (i.e., water and plant) kinetic model was developed. The model adequately described the variation of dibutyl phthalate (DBP) and di-2-ethylhexyl phthalate (DEHP) in the plant-water system by providing the first-order rate constants of plant uptake (k1) and release (k2), microbial degradation in water (k3) and plant degradation (k4). During 10-d incubation, the presence of P. crispus enhanced the removal of DBP and DEHP from water by 6.3% and 22.4%. Compared with the experiment without P. crispus, biodegradation of DBP in water with P. crispus decreased by 8.3% because of plant uptake even though k3 increased by 30%. 21.4% of DBP transferred from water to plants, of which only small amount (5.1%) retained in the plant and the rest (94.9%) was degraded. Different from DBP, biodegradation of DEHP in water with P. crispus was a slightly higher than that without P. crispus. 25.5% of DEHP transferred from water to plants, of which a large portion (73.3%) retained in the plant and the rest (26.7%) was degraded. This finding reveals that the enhancement of DBP removal from surface water is mainly related to faster degradation in the plant, whereas it is mainly related to higher plant accumulation for DEHP. Copyright © 2014 Elsevier Ltd. All rights reserved.

Food Emulsifier Glycerin Monostearate Increases Internal Exposure Levels of Six Priority Controlled Phthalate Esters and Exacerbates Their Male Reproductive Toxicities in Rats.

PubMed

Gao, Hai-Tao; Xu, Run; Cao, Wei-Xin; Zhou, Xu; Yan, Ye-Hui-Mei; Lu, Lingeng; Xu, Qian; Shen, Yang

2016-01-01

Human beings are inevitably exposed to ubiquitous phthalate esters (PAEs). Processed, packaged foods are popular nowadays, in which emulsifiers are frequently added as food additives. It is unclear how emulsifiers affect the bioavailability of ingested PAEs contaminants and their toxicities. The purposes of our study were to explore whether food emulsifier Glycerin Monostearate (GMS) could increase the internal exposure levels of six priority controlled PAEs and affect their reproductive toxicities when male rats are exposed to PAEs mixture (MIXPs). The male rats were exposed to MIXPs by gavage for thirty days in combination with or without given GMS. Phthalate monoesters (MPAEs), primary metabolites of PAEs, in rat urine were used as biomarkers to predict the internal exposure levels of the six PAEs, and their concentrations were determined using UPLC-MS. The reproductive toxicity was evaluated using serum testosterone levels test and histopathology of testes. Results showed that compared to PAEs exposure alone, the internal exposure levels of PAEs increased by 30%-49% in the presence of GMS. PAEs exposure led to the reduction of testosterone level by 23.4%-42.1% in the presence and absence of GMS, respectively, compared to the baseline. Testosterone levels in MIXPs+GMS and DEHP+GMS group were decreased by 9.1% and 13.6%, respectively, compared with MIXPs and DEHP group. Histopathology showed that injuries of testis (deciduous spermatids) were observed, and GMS exacerbated the injuries. The results indicated food emulsifiers chronically taken up might increase safety risks of food PAEs contaminants.

Phthalate esters contamination in soil and plants on agricultural land near an electronic waste recycling site.

PubMed

Ma, Ting Ting; Christie, Peter; Luo, Yong Ming; Teng, Ying

2013-08-01

The accumulation of phthalic acid esters (PAEs) in soil and plants in agricultural land near an electronic waste recycling site in east China has become a great threat to the neighboring environmental quality and human health. Soil and plant samples collected from land under different utilization, including fallow plots, vegetable plots, plots with alfalfa (Medicago sativa L.) as green manure, fallow plots under long-term flooding and fallow plots under alternating wet and dry periods, together with plant samples from relative plots were analyzed for six PAE compounds nominated as prior pollutants by USEPA. In the determined samples, the concentrations of six target PAE pollutants ranged from 0.31-2.39 mg/kg in soil to 1.81-5.77 mg/kg in various plants (dry weight/DW), and their bioconcentration factors (BCFs) ranged from 5.8 to 17.9. Health risk assessments were conducted on target PAEs, known as typical environmental estrogen analogs, based on their accumulation in the edible parts of vegetables. Preliminary risk assessment to human health from soil and daily vegetable intake indicated that DEHP may present a high-exposure risk on all ages of the population in the area by soil ingestion or vegetable consumption. The potential damage that the target PAE compounds may pose to human health should be taken into account in further comprehensive risk assessments in e-waste recycling sites areas. Moreover, alfalfa removed substantial amounts of PAEs from the soil, and its use can be considered a good strategy for in situ remediation of PAEs.

Ashwagandha Leaf Derived Withanone Protects Normal Human Cells Against the Toxicity of Methoxyacetic Acid, a Major Industrial Metabolite

PubMed Central

Priyandoko, Didik; Ishii, Tetsuro; Kaul, Sunil C.; Wadhwa, Renu

2011-01-01

The present day lifestyle heavily depends on industrial chemicals in the form of agriculture, cosmetics, textiles and medical products. Since the toxicity of the industrial chemicals has been a concern to human health, the need for alternative non-toxic natural products or adjuvants that serve as antidotes are in high demand. We have investigated the effects of Ayurvedic herb Ashwagandha (Withania somnifera) leaf extract on methoxyacetic acid (MAA) induced toxicity. MAA is a major metabolite of ester phthalates that are commonly used in industry as gelling, viscosity and stabilizer reagents. We report that the MAA cause premature senescence of normal human cells by mechanisms that involve ROS generation, DNA and mitochondrial damage. Withanone protects cells from MAA-induced toxicity by suppressing the ROS levels, DNA and mitochondrial damage, and induction of cell defense signaling pathways including Nrf2 and proteasomal degradation. These findings warrant further basic and clinical studies that may promote the use of withanone as a health adjuvant in a variety of consumer products where the toxicity has been a concern because of the use of ester phthalates. PMID:21573189

Determination of phthalic acid esters in water samples by hollow fiber liquid-phase microextraction prior to gas chromatography tandem mass spectrometry.

PubMed

González-Sálamo, Javier; González-Curbelo, Miguel Ángel; Socas-Rodríguez, Bárbara; Hernández-Borges, Javier; Rodríguez-Delgado, Miguel Ángel

2018-06-01

A new hollow fiber liquid-phase microextraction (HF-LPME) method has been developed for the extraction of a group of phthalic acid esters (PAEs) of interest from different water samples prior to gas chromatography tandem mass spectrometry analysis. HF-LPME was carried out using 1-octanol as extraction solvent followed by a back extraction step with cyclohexane. The different parameters that affect HF-LPME such as sample pH, ionic strength, extraction time, stirring rate, extraction temperature and back extraction conditions were investigated. The optimized conditions involved the extraction of 10 mL of sample without pH adjustment or addition of salt during 75 min under a stirring of 850 rpm at 60 °C and subsequent desorption with 200 μL of cyclohexane for 10 min in an ultrasonic bath. The method was validated in terms of calibration and recovery studies using dibutyl phthalate-d 4 as internal standard. The developed procedure gave satisfactory recovery (74-120%) and relative standard deviation values (<20%) for the studied PAEs in mineral, tap, pond and waste water samples. Copyright © 2018 Elsevier Ltd. All rights reserved.

Effects of push/pull perfusion and ultrasonication on the extraction efficiencies of phthalate esters in sports drink samples using on-line hollow-fiber liquid-phase microextraction.

PubMed

Chao, Yu-Ying; Lee, Chien-Hung; Chien, Tzu-Yang; Shih, Yu-Hsuan; Lu, Yin-An; Kuo, Ting-Hsuan; Huang, Yeou-Lih

2013-08-28

In previous studies, we developed a process, on-line ultrasound-assisted push/pull perfusion hollow-fiber liquid-phase microextraction (UA-PPP-HF-LPME), combining the techniques of push/pull perfusion (PPP) and ultrasonication with hollow-fiber liquid-phase microextraction (HF-LPME), to achieve rapid extraction of acidic phenols from water samples. In this present study, we further evaluated three more-advanced and novel effects of PPP and ultrasonication on the extraction efficiencies of neutral high-molecular-weight phthalate esters (HPAEs) in sports drinks. First, we found that inner-fiber fluid leakage occurs only in push-only perfusion-based and pull-only perfusion-based HF-LPME, but not in the PPP mode. Second, we identified a significant negative interaction between ultrasonication and temperature. Third, we found that the extraction time of the newly proposed system could be shortened by more than 93%. From an investigation of the factors affecting UA-PPP-HF-LPME, we established optimal extraction conditions and achieved acceptable on-line enrichment factors of 92-146 for HPAEs with a sampling time of just 2 min.

Monitoring of PAEMs and beta-agonists in urine for a small group of experimental subjects and PAEs and beta-agonists in drinking water consumed by the same subjects.

PubMed

Liou, Saou-Hsing; Yang, Gordon C C; Wang, Chih-Lung; Chiu, Yu-Han

2014-07-30

This 5-month study contains two parts: (1) to monitor the concentrations of 11 phthalate esters metabolites (PAEMs) and two beta-agonists in human urine samples collected from a small group of consented participants including 16 females and five males; and (2) to analyze the residues of phthalate esters (PAEs) and beta-agonists in various categories of drinking water consumed by the same group of subjects. Each category of human urine and drinking water had 183 samples of its own. The analytical results showed that nine PAEMs were detected in human urine and eight PAEs were detected in drinking water samples. It was found that average concentrations of PAEMs increased as the age increased, but no significant difference between sexes. Further, using the principal component analysis, the loadings of age effect were found to be two times greater than that of gender effect in terms of four DEHP metabolites. Regarding beta-agonists of concern (i.e., ractopamine and salbutamol), they were neither detected in human urine nor drinking water samples in this study. Copyright © 2014 Elsevier B.V. All rights reserved.

Organic molecular compositions and temporal variations of summertime mountain aerosols over Mt. Tai, North China Plain

NASA Astrophysics Data System (ADS)

Fu, Pingqing; Kawamura, Kimitaka; Okuzawa, Kazuhiro; Aggarwal, Shankar Gopala; Wang, Gehui; Kanaya, Yugo; Wang, Zifa

2008-10-01

Total suspended particles (TSP) were collected at the summit of Mt. Tai (1534 m above sea level) on a daytime and nighttime basis during a summertime campaign (May-June 2006) and were characterized for organic molecular compositions using solvent extraction/derivatization and gas chromatography/mass spectrometry technique. The n-Alkanes, fatty acids, fatty alcohols, sugars, glycerol and polyacids, and phthalate esters were found as major organic compound classes, whereas lignin and resin products, sterols, aromatic acids, hopanes, and polycyclic aromatic hydrocarbons (PAHs) were detected as minor classes. Sugars (49.8-2115 ng m-3, average 640 ng m-3 in daytime; 18.1-4348 ng m-3, 799 ng m-3 in nighttime) were found to be the dominant compound class. Levoglucosan, a specific cellulose pyrolysis product, was detected as the most abundant single compound, followed by C28 fatty alcohol, diisobutyl and di-n-butyl phthalates, C29n-alkane, C16 and C28 fatty acids, and malic acid. By grouping organic compounds based on their sources, we found that emission of terrestrial plant waxes was the most significant source (30-34%) of the TSP, followed by biomass burning products (25-27%) (e.g., levoglucosan and lignin and resin products), soil resuspension (15-18%) due to agricultural activities, secondary oxidation products (8-10%), plastic emission (3-10%), marine/microbial sources (6%), and urban/industrial emissions from fossil fuel use (4%). However, low molecular weight dicarboxylic acids (such as oxalic acid) of photochemical origin were not included in this study. Malic acid was found to be much higher than those reported in the ground level, suggesting an enhanced photochemical production in the free troposphere over mountain areas. Temporal variations of biomass burning tracers (e.g., levoglucosan, galactosan, mannosan) and some higher plant wax derived compound classes suggested that there were two major (E1 and E2) and one minor (E3) biomass-burning events during this campaign. Most of the compound classes showed higher concentrations in nighttime samples when organic aerosols can be long-range transported from different source regions to the summit of Mt. Tai above the planetary boundary layer (PBL). This study also demonstrates that the free troposphere over Mt. Tai is heavily influenced by field burning of agricultural wastes such as wheat straws in the North China Plain during the harvest season in early summer.

Phthalates in plastic bottled non-alcoholic beverages from China and estimated dietary exposure in adults.

PubMed

Yang, Ji-Feng; Yang, Li-Ming; Zheng, Li-Ying; Ying, Guang-Guo; Liu, Cheng-Bin; Luo, Sheng-Lian

2017-03-01

Concentrations of six phthalates were determined in 69 plastic bottled non-alcoholic beverages collected from marketplaces in China. Di-n-butyl phthalate (DBP) and di-(2-ethylhexyl)-phthalate (DEHP) were the most detected compounds with frequencies of 100%. Dimethyl phthalate was found less, with a mean frequency of almost 34%. The samples were divided into seven groups. The frequencies of phthalates in these groups ranged from 6.67% to 100%, which indicated that different types of beverages were differently contaminated by phthalates. DEHP contained the highest mean and median concentrations (1.60 ng g -1 and 0.62 ng g -1 ), followed by DBP (1.34 ng g -1 and 0.27 ng g -1 ). For DBP, the highest phthalate concentration of 14.3 ng g -1 was measured. The results of estimated daily intake (EDI) showed that the risk of Chinese adults exposed to these 6 phthalates in beverages examined was lower than the reference doses as suggested by the United States Environmental Protection Agency. The range of EDI values was between 1.77 × 10 - 4 μg kg-bw -1 day -1 and 0.478 μg kg-bw -1 day -1 .

Analytical method for the identification and assay of 12 phthalates in cosmetic products: application of the ISO 12787 international standard "Cosmetics-Analytical methods-Validation criteria for analytical results using chromatographic techniques".

PubMed

Gimeno, Pascal; Maggio, Annie-Françoise; Bousquet, Claudine; Quoirez, Audrey; Civade, Corinne; Bonnet, Pierre-Antoine

2012-08-31

Esters of phthalic acid, more commonly named phthalates, may be present in cosmetic products as ingredients or contaminants. Their presence as contaminant can be due to the manufacturing process, to raw materials used or to the migration of phthalates from packaging when plastic (polyvinyl chloride--PVC) is used. 8 phthalates (DBP, DEHP, BBP, DMEP, DnPP, DiPP, DPP, and DiBP), classified H360 or H361, are forbidden in cosmetics according to the European regulation on cosmetics 1223/2009. A GC/MS method was developed for the assay of 12 phthalates in cosmetics, including the 8 phthalates regulated. Analyses are carried out on a GC/MS system with electron impact ionization mode (EI). The separation of phthalates is obtained on a cross-linked 5%-phenyl/95%-dimethylpolysiloxane capillary column 30 m × 0.25 mm (i.d.) × 0.25 mm film thickness using a temperature gradient. Phthalate quantification is performed by external calibration using an internal standard. Validation elements obtained on standard solutions, highlight a satisfactory system conformity (resolution>1.5), a common quantification limit at 0.25 ng injected, an acceptable linearity between 0.5 μg mL⁻¹ and 5.0 μg mL⁻¹ as well as a precision and an accuracy in agreement with in-house specifications. Cosmetic samples ready for analytical injection are analyzed after a dilution in ethanol whereas more complex cosmetic matrices, like milks and creams, are assayed after a liquid/liquid extraction using ter-butyl methyl ether (TBME). Depending on the type of cosmetics analyzed, the common limits of quantification for the 12 phthalates were set at 0.5 or 2.5 μg g⁻¹. All samples were assayed using the analytical approach described in the ISO 12787 international standard "Cosmetics-Analytical methods-Validation criteria for analytical results using chromatographic techniques". This analytical protocol is particularly adapted when it is not possible to make reconstituted sample matrices. Copyright © 2012 Elsevier B.V. All rights reserved.

Methods of making organic compounds by metathesis

DOEpatents

Abraham, Timothy W.; Kaido, Hiroki; Lee, Choon Woo; Pederson, Richard L.; Schrodi, Yann; Tupy, Michael John

2015-09-01

Described are methods of making organic compounds by metathesis chemistry. The methods of the invention are particularly useful for making industrially-important organic compounds beginning with starting compositions derived from renewable feedstocks, such as natural oils. The methods make use of a cross-metathesis step with an olefin compound to produce functionalized alkene intermediates having a pre-determined double bond position. Once isolated, the functionalized alkene intermediate can be self-metathesized or cross-metathesized (e.g., with a second functionalized alkene) to produce the desired organic compound or a precursor thereto. The method may be used to make bifunctional organic compounds, such as diacids, diesters, dicarboxylate salts, acid/esters, acid/amines, acid/alcohols, acid/aldehydes, acid/ketones, acid/halides, acid/nitriles, ester/amines, ester/alcohols, ester/aldehydes, ester/ketones, ester/halides, ester/nitriles, and the like.

[Monograph on di-2-propylheptyl phthalate (DPHP) - human biomonitoring (HBM) values for the sum of metabolites oxo-mono-propylheptyl phthalate (oxo-MPHP) and hydroxy-mono-propylheptyl phthalate (OH MPHP) in adult and child urine. Opinion of the Commission "Human Biomonitoring" of the Federal Environment Agency, Germany].

PubMed

2015-07-01

1,2-benzenedicarboxylic acid, bis(2-propylheptyl)ester (bis(2-propylheptyl)phthalate, DPHP) is used as plasticizer for the manufacture of plastics, i.e. mainly polyvinylchloride (PVC). A subchronic feeding study with rats revealed a NOAEL (no observed adverse effect level) of 40 mg/(kg bw · d), which can be used as a point of departure (POD) for the derivation of an HBM-I value. Application of a total assessment factor of 200 leads to an estimation of 200 µg/kg bw as a tolerable daily intake of DPHP. On the basis of the results of metabolism studies with humans it is possible to calculate from the tolerable daily intake of DPHP to the tolerable concentration of specific metabolites in urine. Thus an HBM-I value of 1 mg/L morning urine for children and 1.5 mg/L morning urine for adults was derived for the sum of the oxidized monoesters oxo-MPHP and OH-MPHP, which were identified as robust and conclusive biomarkers for DPHP.

Studies on performance evaluation of a green plasticizer made by enzymatic esterification of furfuryl alcohol and castor oil fatty acid.

PubMed

Mukherjee, Sohini; Ghosh, Mahua

2017-02-10

The esterification of furfuryl alcohol (FA) and castor oil fatty acid (COFA) at 3:1 molar ratio, by immobilized Candida antarctica Lipase B (NS 435 from Novozyme) in a solvent free system gave a maximum yield of 88.64% (%w/w) at 5h. Performance of the FA-COFA ester plasticized Ethyl Cellulose (EC) films were evaluated by surface morphologies, XRD analysis, mechanical properties,thermal properties, water vapor permeability and migration stability test. It was an effective plasticizer with better mechanical properties and thermal stability at the increasing concentration of FA-COFA ester (15-25%) containing EC film, than the traditional plasticizer, i.e; dibutyl phthalate (DBP) in producing good quality films. Chemical structure and the intermolecular interactions between FA-COFA ester and ethyl cellulose chains were the causative agents of these outstanding performances. Therefore, this FA-COFA ester, with significant plasticizing property, at a certain concentration, can be a substitute of DBP. Copyright © 2016 Elsevier Ltd. All rights reserved.

Expressing urine from a gel disposable diaper for biomonitoring using phthalates as an example.

PubMed

Liu, Liangpo; Xia, Tongwei; Guo, Lihua; Cao, Lanyu; Zhao, Benhua; Zhang, Jie; Dong, Sijun; Shen, Heqing

2012-11-01

The urinary metabolites of phthalates are well-accepted exposure biomarkers for adults and children older than 6 years but are not commonly used for infants owing to non-convenient sampling. In the light of this situation, a novel sampling method based on monitoring the urine expressed from the gel diaper was developed. The urine was expressed from the gel absorbent after mixing the absorbent with CaCl(2) and then collected by a laboratory-made device; the urinary phthalate metabolites were extracted and cleaned using a solid-phase extraction (SPE) column and analyzed with high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry / mass spectrometry. To evaluate the method's feasibility, the following factors were investigated: the proportion of CaCl(2) to gel absorbent, the urination volume variation and the target compounds' deposition bias in the diaper, the matrix blank of the different diaper brands, the storage stabilities and the recoveries of creatinine and phthalate metabolites in the expressed urine. Mono-methyl phthalate, mono-ethyl phthalate, mono-butyl phthalate, mono-benzyl phthalate, mono-2-ethylhexyl phthalate and mono-2-ethyl-5-oxohexyl phthalate were involved. 70-80% of the urine can be expressed from the diaper, and the expressed spiking recoveries and the limit of detection of mono-phthalates ranged from 88.5-115% and 0.21-0.50 ng/ml. The method was applied to measure phthalate metabolites in 65 gel diaper samples from 15 infants, and the pilot data suggests the infants are commonly exposed to phthalates. In summary, the method for monitoring of infant exposure to phthalates is sound and validated, and the potential health effects from the vulnerable infants' exposure to phthalates should be concerned.

Organic contaminants associated with suspended sediment collected during five cruises of the Mississippi River and its principal tributaries, May 1988 to June 1990

USGS Publications Warehouse

Rostad, Colleen E.; Bishop, LaDonna M.; Ellis, Geoffrey S.; Leiker, Thomas J.; Monsterleet, Stephanie G.; Pereira, Wilfred E.

2004-01-01

Suspended-sediment samples were obtained from sites along the Mississippi River and its principal tributaries to determine the presence of halogenated hydrophobic organic compounds on the suspended sediment smaller than 63 micrometers. Sample collection involved pumping discharge-weighted volumes of river water along a cross section of the river into a continuous-flow centrifuge to isolate the suspended sediment. The suspended sediment was analyzed by gas chromatography/mass spectrometry for pentachlorobenzene, hexachlorobenzene, pentachloroanisole, chlorothalonil, pentachlorophenol, dachthal, chlordane, nonachlor, and penta-, hexa-, hepta-, and octachlorobiphenyls. Samples collected during June 1989 and February-March 1990 also were analyzed for U.S. Environmental Protection Agency priority pollutants, including polycyclic aromatic hydrocarbons, phthalate esters, and triazines. Samples were collected at sites on the Mississippi River from above St. Louis, Missouri to below New Orleans, Louisiana, and on the Illinois, Missouri, Ohio, Wabash, Cumberland, Tennessee, White, Arkansas, and Yazoo Rivers. Masses of selected halogenated hydrophobic organic compounds associated with the suspended sediment at each site are presented in this report in tabular format, along with suspended-sediment concentration, water discharge, and organic-carbon content.

Using fetal endocrine and genomic signatures to predict the relative potency of phthalate esters and their effects on postnatal development of the male rat reproductive tract

EPA Science Inventory

The first part of this presentation will address concerns expressed by some scientist that the screening and testing protocols for endocrine disrupting chemicals (EDCs) are 1) unable to adequately detect the low dose effects of EDCs, 2) they are unable to define the shape of the ...

Advanced Fast Curing Adhesives for Adverse Conditions

DTIC Science & Technology

2007-07-01

experimentation. The catalyst is composed of 50% phthalate esters and 50% trivalent organic chromium complexes (15). 2.3 Aluminum Lap Plates...adhesives (2). Tape adhesives never provide weld - strength bonds and often have low tackiness when used underwater. Ultraviolet and visible light curable...diisocyanate and diphenylmethane-4, 4 diisocyanate (MDI) (12). The low viscosity ethyl cyanoacrylate Scotch- Weld CA40 was obtained from 3M of St

Effect of Naphthalene, Butylated Hydroxytoluene, Dioctyl Phthalate, and Adipic Dioctyl Ester, Chemicals Found in the Nests of the Formosan Subterranean Termite (Isoptera: Rhinotermitidae) on a Saprophytic Mucor sp.

USDA-ARS?s Scientific Manuscript database

Fungi are commonly found associated with termites and their nests. Four chemicals that have been isolated from the nests of the Formosan subterranean termite, Coptotermes formosanus Shiraki, were evaluated to determine their effect on a common nest fungus, a saprophytic Mucor sp. Butylated hydroxyto...

Removal of the endocrine disrupter butyl benzyl phthalate from the environment

PubMed Central

Karlovsky, Petr

2010-01-01

Butyl benzyl phthalate (BBP), an aryl alkyl ester of 1,2-benzene dicarboxylic acid, is extensively used in vinyl tiles and as a plasticizer in PVC in many commonly used products. BBP, which readily leaches from these products, is one of the most important environmental contaminants, and the increased awareness of its adverse effects on human health has led to a dramatic increase in research aimed at removing BBP from the environment via bioremediation. This review highlights recent progress in the degradation of BBP by pure and mixed bacterial cultures, fungi, and in sludge, sediment, and wastewater. Sonochemical degradation, a unique abiotic remediation technique, and photocatalytic degradation are also discussed. The degradation pathways for BBP are described, and future research directions are considered. PMID:20396882

Association between fetal exposure to phthalate endocrine disruptor and genome-wide DNA methylation at birth.

PubMed

Chen, Chung-Hsing; Jiang, Shih Sheng; Chang, I-Shou; Wen, Hui-Ju; Sun, Chien-Wen; Wang, Shu-Li

2018-04-01

Phthalic acid esters are ubiquitous and antiandrogenic, and may cause systemic effects in humans, particularly with in utero exposure. Epigenetic modification, such as DNA methylation, has been hypothesized to be an important mechanism that mediates certain biological processes and pathogenic effects of in utero phthalate exposure. The aim of this study was to examine the association between genome-wide DNA methylation at birth and prenatal exposure to phthalate. We studied 64 infant-mother pairs included in TMICS (Taiwan Maternal and Infant Cohort Study), a long-term follow-up birth cohort from the general population. DNA methylation levels at more than 450,000 CpG sites were measured in cord blood samples using Illumina Infinium HumanMethylation450 BeadChips. The concentrations of three metabolites of di-(2-ethylhexyl) phthalate (DEHP) were measured using liquid chromatography tandem-mass spectrometry (LC-MS/MS) in urine samples collected from the pregnant women during 28-36 weeks gestation. We identified 25 CpG sites whose methylation levels in cord blood were significantly correlated with prenatal DEHP exposure using a false discovery rate (FDR) of 5% (q-value < 0.05). Via gene-set enrichment analysis (GSEA), we also found that there was significant enrichment of genes involved in the androgen response, estrogen response, and spermatogenesis within those genes showing DNA methylation changes in response to exposure. Specifically, PA2G4, HMGCR, and XRCC6 genes were involved in genes in response to androgen. Phthalate exposure in utero may cause significant alterations in the DNA methylation in cord blood. These changes in DNA methylation might serve as biomarkers of maternal exposure to phthalate in infancy and potential candidates for studying mechanisms via which phthalate may impact on health in later life. Future investigations are warranted. Copyright © 2018 Elsevier Inc. All rights reserved.

Organic compounds in produced waters from shale gas wells.

PubMed

Maguire-Boyle, Samuel J; Barron, Andrew R

2014-01-01

A detailed analysis is reported of the organic composition of produced water samples from typical shale gas wells in the Marcellus (PA), Eagle Ford (TX), and Barnett (NM) formations. The quality of shale gas produced (and frac flowback) waters is a current environmental concern and disposal problem for producers. Re-use of produced water for hydraulic fracturing is being encouraged; however, knowledge of the organic impurities is important in determining the method of treatment. The metal content was determined by inductively coupled plasma optical emission spectrometry (ICP-OES). Mineral elements are expected depending on the reservoir geology and salts used in hydraulic fracturing; however, significant levels of other transition metals and heavier main group elements are observed. The presence of scaling elements (Ca and Ba) is related to the pH of the water rather than total dissolved solids (TDS). Using gas chromatography mass spectrometry (GC/MS) analysis of the chloroform extracts of the produced water samples, a plethora of organic compounds were identified. In each water sample, the majority of organics are saturated (aliphatic), and only a small fraction comes under aromatic, resin, and asphaltene categories. Unlike coalbed methane produced water it appears that shale oil/gas produced water does not contain significant quantities of polyaromatic hydrocarbons reducing the potential health hazard. Marcellus and Barnett produced waters contain predominantly C6-C16 hydrocarbons, while the Eagle Ford produced water shows the highest concentration in the C17-C30 range. The structures of the saturated hydrocarbons identified generally follows the trend of linear > branched > cyclic. Heterocyclic compounds are identified with the largest fraction being fatty alcohols, esters, and ethers. However, the presence of various fatty acid phthalate esters in the Barnett and Marcellus produced waters can be related to their use in drilling fluids and breaker additives rather than their presence in connate fluids. Halogen containing compounds are found in each of the water samples, and although the fluorocarbon compounds identified are used as tracers, the presence of chlorocarbons and organobromides formed as a consequence of using chlorine containing oxidants (to remove bacteria from source water), suggests that industry should concentrate on non-chemical treatments of frac and produced waters.

Development of magnetic micro-solid phase extraction for analysis of phthalate esters in packaged food.

PubMed

Makkliang, Fonthip; Kanatharana, Proespichaya; Thavarungkul, Panote; Thammakhet, Chongdee

2015-01-01

A novel, simple and low cost magnetic multi-walled carbon nanotubes-poly (vinyl alcohol) cryogel-micro-solid phase extraction (magnetic-MWCNTs-PVA cryogel-μ-SPE) sorbent was synthesized by incorporating magnetic particles and MWCNTs into a PVA cryogel. The magnetic-MWCNTs-PVA cryogel-μ-SPE sorbent developed, with a large surface area and macro-porous structure, provided good sorbent-to-sorbent reproducibility (%RSD<8) and each sorbent could be used up to 30 times (%RSD<6). This sorbent was applied for the extraction of dibutyl phthalate (DBP) and di-2-(ethylhexyl) phthalate (DEHP) in packaged food prior to analysis by gas chromatograph coupled with flame ionisation detector (GC-FID). The concentration of DBP and DEHP in hot-water samples from plastic bags were found in the range 0.04-0.15 μg mL(-1) and 0.03-0.20 μg mL(-1), respectively, but only DEHP was found in clear chicken soup samples in the range 0.02-0.07 μg mL(-1). Copyright © 2014 Elsevier Ltd. All rights reserved.

Hexamoll DINCH plasticised PVC containers for the storage of platelets

PubMed Central

Nair, C. S. Bhaskaran; Vidya, R.; Ashalatha, P. M.

2011-01-01

Introduction: Containers for the storage of platelets are made using polyvinyl chloride plasticised with di, (2-ethyl hexyl) phthalate, n-butyryl, tri (n-hexyl) citrate and tri (2-ethyl hexyl) mellitate or using special poly olefins without plasticiser. Of these, the first two have disadvantages such as plasticiser leaching and impairment of platelet function. Polyolefin bags cannot be HF welded or steam sterilized. Mellitate plasticised bags can store platelets well for five days but they are not completely phthalate free. Research and Development: We have developed a new generation of containers made of PVC plasticised with the non DEHP, non aromatic plasticiser,1,2- Cyclohexanedicarboxylic acid, diisononyl ester (Hexamoll DINCH) which can store platelets without loss of function for at least six days. Observation: The present studies show that DINCH plasticised PVC bags (TPL-167) are well suited for the storage of platelet concentrates for more than five days. Conclusion: The present studies show that the PVC plasticised with the non phthalate, non aromatic, non toxic plasticiser DINCH is a viable alternative to other existing containers for the storage of platelets for more than five days. PMID:21572709

Pregnancy urinary phthalate metabolite concentrations and gestational diabetes risk factors.

PubMed

James-Todd, Tamarra M; Meeker, John D; Huang, Tianyi; Hauser, Russ; Ferguson, Kelly K; Rich-Edwards, Janet W; McElrath, Thomas F; Seely, Ellen W

2016-11-01

Epidemiologic studies suggest phthalate metabolite concentrations are associated with type 2 diabetes. GDM is a strong risk factor for type 2 diabetes. Little is known about phthalates and GDM risk factors (i.e. 1st trimester body mass index (BMI), gestational weight gain (GWG), and 2nd trimester glucose levels). A total of 350 women participating in Lifecodes pregnancy cohort (Boston, MA), delivered at term and had pregnancy urinary phthalate metabolite concentrations. Nine specific gravity-adjusted urinary phthalate metabolites were evaluated. General linear regression was used to assess associations between quartiles of phthalate metabolites and continuous 1st trimester BMI and late 2nd trimester blood glucose. Linear mixed models were used for total GWG. Multivariable logistic regression was used for phthalate concentrations and categorized GWG and impaired glucose tolerance defined as glucose≥140mg/dL based on a 50-gram glucose load test. Models were adjusted for potential confounders. There were no associations between 1st trimester urinary phthalate metabolite concentrations and 1st trimester BMI. Mono-ethyl phthalate concentrations averaged across pregnancy were associated with a 2.17 increased odds of excessive GWG (95% CI: 0.98, 4.79). Second trimester mono-ethyl phthalate was associated with increased odds of impaired glucose tolerance (adj. OR: 7.18; 95% CI: 1.97, 26.15). A summary measure of di-2-ethylhexyl phthalate metabolite concentrations were inversely associated with impaired glucose tolerance (adj. OR: 0.25; adj. 95% CI: 0.08, 0.85). Higher exposure to mono-ethyl phthalate, a metabolite of the parent compound of di-ethyl phthalate, may be associated with excessive GWG and impaired glucose tolerance; higher di-2-ethylhexyl phthalate was associated with reduced odds of impaired glucose tolerance. Copyright © 2016 Elsevier Ltd. All rights reserved.

Semivolatile Endocrine-Disrupting Compounds in Paired Indoor and Outdoor Air in Two Northern California Communities

PubMed Central

2010-01-01

Interest in the health effects of potential endocrine-disrupting compounds (EDCs) that are high production volume chemicals used in consumer products has made exposure assessment and source identification a priority. We collected paired indoor and outdoor air samples in 40 nonsmoking homes in urban, industrial Richmond, CA, and 10 in rural Bolinas, CA. Samples were analyzed by GC-MS for 104 analytes, including phthalates (11), alkylphenols (3), parabens (3), polybrominated diphenyl ether (PBDE) flame retardants (3), polychlorinated biphenyls (PCBs) (3), polycyclic aromatic hydrocarbons (PAHs) (24), pesticides (38), and phenolic compounds (19). We detected 39 analytes in outdoor air and 63 in indoor air. For many of the phenolic compounds, alkylphenols, phthalates, and PBDEs, these represent some of the first outdoor measures and the first analysis of the relative importance of indoor and outdoor sources in paired samples. Data demonstrate higher indoor concentrations for 32 analytes, suggesting primarily indoor sources, as compared with only 2 that were higher outdoors. Outdoor air concentrations were higher in Richmond than Bolinas for 3 phthalates, 10 PAHs, and o-phenylphenol, while indoor air levels were more similar between communities, except that differences observed outdoors were also seen indoors. Indoor concentrations of the most ubiquitous chemicals were generally correlated with each other (4-t-butylphenol, o-phenylphenol, nonylphenol, several phthalates, and methyl phenanthrenes; Kendall correlation coefficients 0.2−0.6, p < 0.05), indicating possible shared sources and highlighting the importance of considering mixtures in health studies. PMID:20681565

Accuracy investigation of phthalate metabolite standards.

PubMed

Langlois, Éric; Leblanc, Alain; Simard, Yves; Thellen, Claude

2012-05-01

Phthalates are ubiquitous compounds whose metabolites are usually determined in urine for biomonitoring studies. Following suspect and unexplained results from our laboratory in an external quality-assessment scheme, we investigated the accuracy of all phthalate metabolite standards in our possession by comparing them with those of several suppliers. Our findings suggest that commercial phthalate metabolite certified solutions are not always accurate and that lot-to-lot discrepancies significantly affect the accuracy of the results obtained with several of these standards. These observations indicate that the reliability of the results obtained from different lots of standards is not equal, which reduces the possibility of intra-laboratory and inter-laboratory comparisons of results. However, agreements of accuracy have been observed for a majority of neat standards obtained from different suppliers, which indicates that a solution to this issue is available. Data accuracy of phthalate metabolites should be of concern for laboratories performing phthalate metabolite analysis because of the standards used. The results of our investigation are presented from the perspective that laboratories performing phthalate metabolite analysis can obtain accurate and comparable results in the future. Our findings will contribute to improving the quality of future phthalate metabolite analyses and will affect the interpretation of past results.

Semi-volatile organic compounds in the particulate phase in dwellings: A nationwide survey in France

NASA Astrophysics Data System (ADS)

Mandin, Corinne; Mercier, Fabien; Ramalho, Olivier; Lucas, Jean-Paul; Gilles, Erwann; Blanchard, Olivier; Bonvallot, Nathalie; Glorennec, Philippe; Le Bot, Barbara

2016-07-01

Sixty-six semi-volatile organic compounds (SVOCs)-phthalates, polybrominated diphenyl ethers (PBDEs), polychlorinated biphenyls (PCBs), polycyclic aromatic hydrocarbons (PAHs), one pyrethroid, organochlorine and organophosphorous pesticides, alkylphenols, synthetic musks, tri-n-butylphosphate and triclosan-were measured on PM10 filters collected over 7 days during a nationwide survey of 285 French dwellings, representative of nearly 25 million housing units. Thirty-five compounds were detected in more than half of the dwellings. PAHs, phthalates and triclosan were the major particle-bound SVOCs, with a median concentration greater than 1 ng m-3 for butylbenzyl phthalate (BBP) (median: 1.6 ng m-3), di(2-ethylhexyl) phthalate (DEHP) (46 ng m-3) and di-iso-nonyl phthalate (DiNP) (7.9 ng m-3), and greater than 0.1 ng m-3 for triclosan (114 pg m-3), benzo(a)pyrene (138 pg m-3), benzo(b)fluoranthene (306 pg m-3), benzo(g,h,i)perylene (229 pg m-3), and indeno(1,2,3-c,d)pyrene (178 pg m-3). For most of the SVOCs, higher concentrations were found in the dwellings of smokers and during the heating season. The concentrations of banned SVOCs-namely, PCBs and organochlorine pesticides-were correlated. Permethrin, 4-tert-butylphenol and bisphenol-A showed no correlation with the other SVOCs and seemed to have their own specific sources. Most SVOCs were positively associated with PM10 concentration, suggesting that any factor that raises the mass of indoor airborne particles also increases the exposure to SVOCs through inhalation.

Analysis of phthalic acid diesters, monoester, and other plasticizers in polyvinyl chloride household products in Japan.

PubMed

Kawakami, Tsuyoshi; Isama, Kazuo; Matsuoka, Atsuko

2011-01-01

The aim of this study was to determine the concentrations of six phthalic acid diesters (PAEs) [di(2-ethylhexyl) phthalate (DEHP), di-n-butyl phthalate (DBP), butyl benzyl phthalate (BBP), diisononyl phthalate (DINP), di-n-octyl phthalate (DNOP), and diisodecyl phthalate (DIDP)], two non-phthalic plasticizers [di(2-ethylhexyl) adipate (DEHA), 2,2,4-trimethyl-1,3-pentanediol diisobutylate (TMPDIB)], and mono 2-ethylhexyl phthalate(MEHP) in polyvinyl chloride (PVC) household products that children often places in their mouths and/or contact with their skin (41 products, 47 samples) in Japan. The detection frequencies of the studied compounds were as follows: DEHP (79 %), DINP-2 (13 %), DINP-1 (11 %), DBP (8.5 %), DEHA (8.5 %), DIDP (4.3 %), and DNOP (2.1 %). Concentrations of these compounds ranged from 0.021 % to 48 %. BBP and TMPDIB were not detected in the all samples. Most samples contained DEHP and DINP at high concentrations over 0.1 %. High concentrations of PAEs were detected in PVC household products that appear appealing to children and can possibly be licked and chewed by them. Di(2-ethylhexyl) terephtalete, diisononyl 1,2-cyclohexanedicarboxylic acid, acetyl tributyl citrate, and di(2-ethylhexyl) 4-cyclohexene-1,2-dicarboxylate used as substitute plasticizers were also detected in several samples. MEHP was present in 70 % of the samples, with concentrations ranging from trace amounts to 140 μg/g. The ratios of MEHP against DEHP were 6.2 × 10(-4) to 1.6 × 10(-1) %. MEHP in the household products investigated in this study was most probably an impurity in DEHP. The high concentrations of PAEs detected in products that children often place in their mouth reveal the importance of replacing plasticizers in common household products, and not just children's toys, with safer alternatives.

Data from one test "Semi-Volatile Organic Compound Small Chamber for bis (2-Ethylhexyl) phthalate in Vinyl Flooring Test 2"

EPA Science Inventory

This data was generated from a small chamber bis(2-ethylhexyl) phthalate (DEHP) emission test. It was to participate an interaboratory study of DEHP emissions from vinyl flooring in a SVOC emission chamber organized by Virginia Polytechnic Institute and State University (VT).

Contamination level of four priority phthalates in North Indian wastewater treatment plants and their fate in sequencing batch reactor systems.

PubMed

Gani, Khalid Muzamil; Rajpal, Ankur; Kazmi, Absar Ahmad

2016-03-01

The contamination level of four phthalates in untreated and treated wastewater of fifteen wastewater treatment plants (WWTPs) and their fate in a full scale sequencing batch reactor (SBR) based WWTP was evaluated in this study. The four phthalates were diethyl phthalate (DEP), dibutyl phthalate (DBP), benzylbutyl phthalate (BBP) and diethylhexyl phthalate (DEHP). All compounds were present in untreated wastewater with DEHP being present in the highest mean concentration of 28.4 ± 5.3 μg L(-1). The concentration was in the range of 7.3 μg L(-1) (BBP) to 28.4 μg L(-1) (DEHP) in untreated wastewater and 1.3 μg L(-1) (DBP) to 2.6 μg L(-1) (DEHP) in treated wastewater. The nutrient removal process and advance tertiary treatment based WWTPs showed the highest phthalate removal efficiencies of 87% and 93%, respectively. The correlation between phthalate removal and conventional performance of WWTPs was positive. Fate analysis of these phthalates in a SBR based WWTP showed that total removal of the sum of phthalates in a primary settling tank and SBR was 84% out of which 55% is removed by biodegradation and 29% was removed by sorption to primary and secondary sludge. The percentage removal of four phthalates in primary settling tanks was 18%. Comparison of the diluted effluent DEHP concentration with its environmental quality standards showed that the dilution in an effluent receiving water body can reduce the DEHP emissions to acceptable values.

Pyrotechnic filled molding powder

DOEpatents

Hartzel, Lawrence W.; Kettling, George E.

1978-01-01

The disclosure relates to thermosetting molding compounds and more particularly to a pyrotechnic filled thermosetting compound comprising a blend of unfilled diallyl phthalate molding powder and a pyrotechnic mixture.

Flow of sewage sludge-borne phthalate esters (PAEs) from human release to human intake: implication for risk assessment of sludge applied to soil.

PubMed

Meng, Xiang-Zhou; Wang, Ying; Xiang, Nan; Chen, Ling; Liu, Zhigang; Wu, Bing; Dai, Xiaohu; Zhang, Yun-Hui; Xie, Zhiyong; Ebinghaus, Ralf

2014-04-01

The wide production and use of phthalate esters (PAEs) in both industry and commercial products lead to their ubiquitous existence in the environment. However, understanding flow and pathway of human exposure to PAEs from sources to receptors is necessary and challenging. In this study, we selected final sewage sludge, an inevitable byproduct of wastewater treatment plants (WWTP), as one type of important carrier/sources of PAEs to clarify the flow of PAEs between human and the environment, e.g. the release by human to sludge and in turn ingestion by human after these sludges were disposed as soil amendment. Twenty-five sludge samples were collected from 25 wastewater treatment plants (WWTPs) in Shanghai, East China. Of all 16 PAE congeners, di(2-ethylhexyl) phthalate (DEHP) and dibutyl phthalate (DnBP) were predominant with mean concentrations of 97.4 and 22.4 μg/g dw, respectively, both locating at the high end of the global range. WWTP treating industrial waster generally contained higher PAEs compared to those treating domestic wastewater, but no positive relationship was found between PAE levels with the percentage of industrial wastewater. Principal component analysis (PCA) showed that similar PAE sources for all WWTPs in Shanghai with three exceptions, in which specific PAE products were made. The annual mass loadings via sludge of DEHP, DnBP, and Σ16PAEs were 31.4, 7.44, and 39.6 tons in Shanghai and 1042, 247, and 1314 tons in China, respectively, only accounting for 0.09% of the total consumption of PAEs in China. If this sludge is applied in soil, human will take 16.4 and 3.8 μg/kg bw for DEHP and DnBP every day, respectively, via dietary and soil ingestion, which were lower than the toxicological safety parameters. To the best of our knowledge, this is the first report to analyze the flow of sludge-borne PAEs from human release to human intake. Copyright © 2014 Elsevier B.V. All rights reserved.

Evaluation of cytotoxicity and oxidative DNA damaging effects of di(2-ethylhexyl)-phthalate (DEHP) and mono(2-ethylhexyl)-phthalate (MEHP) on MA-10 Leydig cells and protection by selenium

DOE Office of Scientific and Technical Information (OSTI.GOV)

Erkekoglu, Pinar; Hacettepe University, Faculty of Pharmacy, Department of Toxicology, 06100 Ankara; Rachidi, Walid

2010-10-01

Di(2-ethylhexyl)-phthalate (DEHP) is the most abundantly used phthalate derivative, inevitable environmental exposure of which is suspected to contribute to the increasing incidence of testicular dysgenesis syndrome in humans. Oxidative stress and mitochondrial dysfunction in germ cells are suggested to contribute to phthalate-induced disruption of spermatogenesis in rodents, and Leydig cells are one of the main targets of phthalates' testicular toxicity. Selenium is known to be involved in the modulation of intracellular redox equilibrium, and plays a critical role in testis, sperm, and reproduction. This study was aimed to investigate the oxidative stress potential of DEHP and its consequences in testicularmore » cells, and examine the possible protective effects of selenium using the MA-10 mouse Leydig tumor cell line as a model. In the presence and absence of selenium compounds [30 nM sodium selenite (SS), and 10 {mu}M selenomethionine (SM)], the effects of exposure to DEHP and its main metabolite mono(2-ethylhexyl)-phthalate (MEHP) on the cell viability, enzymatic and non-enzymatic antioxidant status, ROS production, p53 expression, and DNA damage by alkaline Comet assay were investigated. The overall results of this study demonstrated the cytotoxicity and genotoxicity potential of DEHP, where MEHP was found to be more potent than the parent compound. SS and SM produced almost the same level of protection against antioxidant status modifying effects, ROS and p53 inducing potentials, and DNA damaging effects of the two phthalate derivatives. It was thus shown that DEHP produced oxidative stress in MA-10 cells, and selenium supplementation appeared to be an effective redox regulator in the experimental conditions used in this study, emphasizing the critical importance of the appropriate selenium status.« less

Simultaneous determination of trace migration of phthalate esters in honey and royal jelly by GC-MS.

PubMed

Zhou, Jinhui; Qi, Yitao; Wu, Hongmei; Diao, Qingyun; Tian, Feifei; Li, Yi

2014-03-01

A simple, rapid, and reliable liquid-liquid extraction coupled to GC-MS method was developed and validated for the quantification of 22 phthalate esters (PAEs) in honey and royal jelly. Instrument parameters for GC-MS were tested to obtain the satisfactory separation between 22 PAEs with high sensitivity. The extraction procedure was optimized in order to achieve the best recovery. The following criteria were used to validate the developed method: linearity, LOD, lower LOQ, precision, accuracy, matrix effect and carry-over. Correlation coefficients were >0.999 by applying the linear regression model based on the least-squares method with a weighting factor (1/x). The intra- and interday precision were within 12.7% in terms of RSD, and the accuracy was within -11.8% in terms of relative error. The mean extraction recoveries ranged between 80.1 and 110.9% for honey and royal jelly. No significant matrix effect and carry-over for PAEs were observed for the analysis of honey and royal jelly samples. A total of 20 real samples were analyzed for a mini-survey using the developed method. Seven PAEs in honey samples and five PAEs in royal jelly samples were found, indicating potential contamination with several PAEs. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

[Anaerobic biodegradation of phthalic acid esters (Paes) in municipal sludge].

PubMed

Liang, Zhi-Feng; Zhou, Wen; Lin, Qing-Qi; Yang, Xiu-Hong; Wang, Shi-Zhong; Cai, Xin-De; Qiu, Rong-Liang

2014-04-01

Phthalic acid esters (PAEs), a class of organic pollutants with potent endocrine-disrupting properties, are widely present in municipal sludge. Study of PAEs biodegradation under different anaerobic biological treatment processes of sludge is, therefore, essential for a safe use of sludge in agricultural practice. In this study, we selected two major sludge PAEs, i.e. di-n-butyl phthalate (DBP) and di-(2-enthylhexyl) phthalate (DEHP), to investigate their biodegradation behaviors in an anaerobic sludge digestion system and a fermentative hydrogen production system. The possible factors influencing PAEs biodegradation in relation to changes of sludge properties were also discussed. The results showed that the biodegradation of DBP reached 99.6% within 6 days, while that of DEHP was 46.1% during a 14-day incubation period in the anaerobic digestion system. By comparison, only 19.5% of DBP was degraded within 14 days in the fermentative hydrogen production system, while no degradation was detected for DEHP. The strong inhibition of the degradation of both PAEs in the fermentative hydrogen production system was ascribed to the decreases in microbial biomass and ratios of gram-positive bacteria/gram-negative bacteria and fungi/ bacteria, and the increase of concentrations of volatile fatty acids (e. g. acetic acid, propionic acid and butyric acid) during the fermentative hydrogen-producing process.

[Analysis of phthalate esters in plastic-packaging bags on-line sample stacking-microemulsion electrokinetic chromatography].

PubMed

Xiao, Jia; Huang, Ying; Wang, Minyi; Chen, Guonan

2012-09-01

Two convenient, effective, and reproducible methods using microemulsion electrokinetic chromatography (MEEKC)-normal stacking mode (NSM) and reversed electrode polarity stacking mode (REPSM) were developed for the on-line sample stacking of phthalate esters (PAEs). REPSM coupled with MEEKC increased the sensitivity of 937.5 to 7,143 times for four PAEs compared to the conventional MEEKC. The separating conditions in the MEEKC method were studied, and many factors influencing the two sample stacking processes were investigated in detail. The optimum sample matrices for the two stacking methods were as follows: 30 mmol/L sodium cholate (SC) and 30.0 mmol/L borate (pH 8.5). Additionally, sample injections as large as 3.45 kPa x 40 s and 3.45 kPa x 90 s were applied for NSM-MEEKC and REPSM-MEEKC, respectively. The linear relationship and reproducibility were also examined. Under the optimum conditions, the detection limits (S/N = 3) of the PAEs were in the ranges of 0.021 - 0.33 mg/L and 0.7 - 4 microg/L for NSM-MEEKC and REPSM-MEEKC, respectively. The proposed REPSM-MEEKC has been successfully applied to determine PAEs in plastic-packaging bags, and the spiked recoveries were in the range of 89.1% - 105.6% with satisfactory results.

Analytical methods for the quantification of bisphenol A, alkylphenols, phthalate esters, and perfluoronated chemicals in biological samples.

PubMed

Nakazawa, Hiroyuki; Iwasaki, Yusuke; Ito, Rie

2014-01-01

Our modern society has created a large number of chemicals that are used for the production of everyday commodities including toys, food packaging, cosmetic products, and building materials. We enjoy a comfortable and convenient lifestyle with access to these items. In addition, in specialized areas, such as experimental science and various medical fields, laboratory equipment and devices that are manufactured using a wide range of chemical substances are also extensively employed. The association between human exposure to trace hazardous chemicals and an increased incidence of endocrine disease has been recognized. However, the evaluation of human exposure to such endocrine disrupting chemicals is therefore imperative, and the determination of exposure levels requires the analysis of human biological materials, such as blood and urine. To obtain as much information as possible from limited sample sizes, highly sensitive and reliable analytical methods are also required for exposure assessments. The present review focuses on effective analytical methods for the quantification of bisphenol A (BPA), alkylphenols (APs), phthalate esters (PEs), and perfluoronated chemicals (PFCs), which are chemicals used in the production of everyday commodities. Using data obtained from liquid chromatography/mass spectrometry (LC/MS) and LC/MS/MS analyses, assessments of the risks to humans were also presented based on the estimated levels of exposure to PFCs.

Evaluation of a Screening System for Obesogenic Compounds: Screening of Endocrine Disrupting Compounds and Evaluation of the PPAR Dependency of the Effect

PubMed Central

Pereira-Fernandes, Anna; Demaegdt, Heidi; Vandermeiren, Karine; Hectors, Tine L. M.; Jorens, Philippe G.; Blust, Ronny; Vanparys, Caroline

2013-01-01

Recently the environmental obesogen hypothesis has been formulated, proposing a role for endocrine disrupting compounds (EDCs) in the development of obesity. To evaluate this hypothesis, a screening system for obesogenic compounds is urgently needed. In this study, we suggest a standardised protocol for obesogen screening based on the 3T3-L1 cell line, a well-characterised adipogenesis model, and direct fluorescent measurement using Nile red lipid staining technique. In a first phase, we characterised the assay using the acknowledged obesogens rosiglitazone and tributyltin. Based on the obtained dose-response curves for these model compounds, a lipid accumulation threshold value was calculated to ensure the biological relevance and reliability of statistically significant effects. This threshold based method was combined with the well described strictly standardized mean difference (SSMD) method for classification of non-, weak- or strong obesogenic compounds. In the next step, a range of EDCs, used in personal and household care products (parabens, musks, phthalates and alkylphenol compounds), were tested to further evaluate the obesogenicity screening assay for its discriminative power and sensitivity. Additionally, the peroxisome proliferator activated receptor γ (PPARγ) dependency of the positive compounds was evaluated using PPARγ activation and antagonist experiments. Our results showed the adipogenic potential of all tested parabens, several musks and phthalate compounds and bisphenol A (BPA). PPARγ activation was associated with adipogenesis for parabens, phthalates and BPA, however not required for obesogenic effects induced by Tonalide, indicating the role of other obesogenic mechanisms for this compound. PMID:24155963

Growth and antioxidant defense responses of wheat seedlings to di-n-butyl phthalate and di (2-ethylhexyl) phthalate stress.

PubMed

Gao, Minling; Dong, Youming; Zhang, Ze; Song, Wenhua; Qi, Yun

2017-04-01

Phthalate acid esters (PAEs) are vital environmental hormone-like chemicals that are noxious to plants, animals, and human beings. In this study, the influences of di-n-butyl phthalate (DBP) and di (2-ethylhexyl) phthalate (DEHP) on the seed germination, root morphology, and various physiological changes of wheat seedlings were investigated by analyzing superoxide anion (O 2 - ) accumulation, antioxidant enzyme activity, and lipid peroxidation. DBP and DEHP were found to obviously inhibit germination only at high concentrations, but significantly affected root morphology even at lower concentrations. Their toxic effects were the most severe on root elongation, followed by shoot elongation, and were the least severe on germination rate, indicating that root elongation was the best index for evaluating DBP and DEHP eco-toxicity. DBP and DEHP also enhanced O 2 - and malondialdehyde levels and membrane permeability, as well as produced changes in the antioxidant status and PAE content in the stem and leaf (combined tissues, hereafter shoot) and root tissues. The activities of superoxide dismutase, catalase, and peroxidase increased at low and medium DBP and DEHP concentrations, but declined at high PAE concentrations. These results indicated that PAEs could exert oxidative damage in the early development stage of wheat, particularly at higher concentrations. DBP and DEHP accumulation was higher in the roots than in the shoot tissues, and their levels in these tissues increased with increasing PAE concentrations, supporting their more-serious toxic effects on roots than those on shoots. Further, the physicochemical properties of DBP rendered it more harmful than DEHP. Copyright © 2017 Elsevier Ltd. All rights reserved.

Urinary arsenic, pesticides, heavy metals, phthalates, polyaromatic hydrocarbons, and polyfluoroalkyl compounds are associated with sleep troubles in adults: USA NHANES, 2005-2006.

PubMed

Shiue, Ivy

2017-01-01

Links between environmental chemicals and human health have emerged, but the effects on sleep health were less studied. Therefore, the aim of the present study was to investigate the relationships of different sets of environmental chemicals and common sleep troubles in a national and population-based setting. Data were retrieved from the United States National Health and Nutrition Examination Surveys, 2005-2006 including demographics, serum measurements, lifestyle factors, self-reported sleep troubles, and urinary environmental chemical concentrations. Statistical analyses including descriptive statistics, t-test, chi-square test, and survey-weighted logistic regression models were performed. Of all 5563 Americans aged 18-85, 2331 (42.0%) had wake-up at night, 2914 (52.5%) felt unrested during the day, 740 (13.4%) had leg jerks while sleeping, and 1059 (19.1%) had leg cramps for 2+ times a month. Higher levels of urinary arsenic, phthalates, and polyfluoroalkyl compounds were associated with wake-up at night. Higher levels of urinary 4-tert-octylphenol and polyfluoroalkyl compounds were associated with being unrested during the day. Higher levels of urinary arsenic, polyaromatic hydrocarbons, and polyfluoroalkyl compounds were associated with leg jerks while sleeping. Higher levels of urinary pesticides, heavy metals, phthalates, and polyaromatic hydrocarbons were associated with leg cramps while sleeping. However, there were no significant associations with other environmental chemicals such as parabens, bisphenol A, benzophenone-3, triclosan, perchlorate, nitrate, or thiocyanate. Eliminating arsenic, heavy metals, phthalate, pesticides, polyaromatic hydrocarbons, and polyfluoroalkyl compounds to improve sleep health might be considered while understanding the biological pathway with a longitudinal or experimental approach in future research would be suggested.

Indoor air quality in hairdressing salons in Taipei.

PubMed

Chang, C-J; Cheng, S-F; Chang, P-T; Tsai, S-W

2018-01-01

To improve indoor air quality and to protect public health, Taiwan has enacted the "Indoor Air Quality Act (IAQ Act)" in 2012. For the general public, the indoor air quality in hair salons is important because it is a popular location that people will often visit for hair treatments. However, only a few exposure assessments regarding air pollutants have previously been performed in hair salons. To assess the air quality of hairdressing environments in Taipei, ten hairdressing salons were included for a walk-through survey in this study. In addition, the airborne concentrations of formaldehyde, volatile organic compounds (VOCs), CO 2 , and phthalate esters were also determined in 5 salons. Charcoal, XAD-2, and OVS-Tenax tubes were used for the air sampling, while the samples were analyzed with gas chromatography/mass spectrometer. It was found that the products used in hair salons contained various chemicals. In fact, from the walk-through survey, a total of 387 different ingredients were found on 129 hair product labels. The hair salons were not well ventilated, with CO 2 levels of 600 to 3576 ppm. The formaldehyde concentrations determined in this study ranged from 12.40 to 1.04 × 10 3  μg m -3 , and the maximum level was above the permissible exposure limit (PEL) of US Occupational Safety and Health Administration (US OSHA). Additionally, 83% of the samples were with levels higher than the standard regulated by Taiwan's IAQ Act. The concentrations of VOCs and phthalate esters were below the occupational exposure limits (OELs), but higher than what was found in general residential environments. The hair products were considered as the major source of air pollutants because significantly higher concentrations were found around the working areas. The number of perming treatments, the number of workers, and the frequency of using formaldehyde releasing products, were found to be associated with the levels of formaldehyde. This study indicates that efforts are needed to improve the indoor air quality in hairdressing salons in Taipei. © 2017 John Wiley & Sons A/S. Published by John Wiley & Sons Ltd.

In vitro functional screening as a means to identify new plasticizers devoid of reproductive toxicity

DOE Office of Scientific and Technical Information (OSTI.GOV)

Boisvert, Annie; Jones, Steven; Issop, Leeyah

Plasticizers are indispensable additives providing flexibility and malleability to plastics. Among them, several phthalates, including di (2-ethylhexyl) phthalate (DEHP), have emerged as endocrine disruptors, leading to their restriction in consumer products and creating a need for new, safer plasticizers. The goal of this project was to use in vitro functional screening tools to select novel non-toxic plasticizers suitable for further in vivo evaluation. A panel of novel compounds with satisfactory plasticizer properties and biodegradability were tested, along with several commercial plasticizers, such as diisononyl-cyclohexane-1,2-dicarboxylate (DINCH®). MEHP, the monoester metabolite of DEHP was also included as reference compound. Because phthalates targetmore » mainly testicular function, including androgen production and spermatogenesis, we used the mouse MA-10 Leydig and C18-4 spermatogonial cell lines as surrogates to examine cell survival, proliferation, steroidogenesis and mitochondrial integrity. The most promising compounds were further assessed on organ cultures of rat fetal and neonatal testes, corresponding to sensitive developmental windows. Dose-response studies revealed the toxicity of most maleates and fumarates, while identifying several dibenzoate and succinate plasticizers as innocuous on Leydig and germ cells. Interestingly, DINCH®, a plasticizer marketed as a safe alternative to phthalates, exerted a biphasic effect on steroid production in MA-10 and fetal Leydig cells. MEHP was the only plasticizer inducing the formation of multinucleated germ cells (MNG) in organ culture. Overall, organ cultures corroborated the cell line data, identifying one dibenzoate and one succinate as the most promising candidates. The adoption of such collaborative approaches for developing new chemicals should help prevent the development of compounds potentially harmful to human health. - Highlights: • Phthalate plasticizers exert toxic effects on male reproduction. • Reproductive toxicity of new plasticizers was assessed by functional assays. • Mouse Leydig and germ cell lines, and rat perinatal testis cultures were used. • Survival, proliferation, steroidogenesis, abnormal germ cell formation were examined. • Reproductive toxic and innocuous plasticizer candidates were identified.« less

Biodegradation of dimethyl phthalate by Sphingomonas sp. isolated from phthalic-acid-degrading aerobic granules.

PubMed

Zeng, Ping; Moy, Benjamin Yan-Pui; Song, Yong-Hui; Tay, Joo-Hwa

2008-10-01

Phthalic acid esters (PAEs) contamination in water, air, and soil is one of the major environmental concerns in many countries. Besides the PAE biodegradation process, the PAE degrading bacteria have become one of the focuses of study. This study reports the successful isolation of one kind of indigenous bacterium PA-02 from phthalic acid (PA)-degrading aerobic granules. Based on its 16S ribosomal DNA sequence, isolate PA-02 was identified as Sphingomonas genus with 100% similarity to Sphingomonas sp. strain D84532. Strain PA-02 was a Gram-negative, rod-shaped bacterium with strong auto-aggregation ability. In particular, the strain PA-02 possessed PAE-degrading ability without acclimation. Results of growth tests showed that strain PA-02 could degrade dimethyl phthalate (DMP), dibutyl phthalate, and diethylhexyl phthalate. The specific degradation rates of DMP and PA were concentration-dependent with maximum values of 0.4 g-DMP g(-1) biomass h(-1) and 1.3 g-PA g(-1) biomass h(-1), respectively. Kinetic studies also revealed that PA-02 was robust under high concentrations of DMP and PA. Even when the PA concentration was increased to 1,000.0 mg l(-1), the specific PA degradation rate was about 0.25 g-PA g(-1) biomass h(-1). The corresponding value for DMP was 0.067 g-DMP g(-1) biomass h(-1) at 1,000 mg l(-1).

An enhanced procedure for measuring organic acids and methyl esters in PM2.5

NASA Astrophysics Data System (ADS)

Liu, F.; Duan, F. K.; He, K. B.; Ma, Y. L.; Rahn, K. A.; Zhang, Q.

2015-11-01

A solid-phase extraction (SPE) pretreatment procedure allowing organic acids to be separated from methyl esters in fine aerosol has been developed. The procedure first separates the organic acids from fatty acid methyl esters (FAMEs) and other nonacid organic compounds by aminopropyl-based SPE cartridge and then quantifies them by gas chromatography/mass spectrometry. The procedure prevents the fatty acids and dimethyl phthalate from being overestimated, and so allows us to accurately quantify the C4-C11 dicarboxylic acids (DCAs) and the C8-C30 monocarboxylic acids (MCAs). Results for the extraction of DCAs, MCAs, and AMAs in eluate and FAMEs in effluate by SAX and NH2 SPE cartridges exhibited that the NH2 SPE cartridge gave higher extraction efficiency than the SAX cartridge. The recoveries of analytes ranged from 67.5 to 111.3 %, and the RSD ranged from 0.7 to 10.9 %. The resulting correlations between the aliphatic acids and FAMEs suggest that the FAMEs had sources similar to those of the carboxylic acids, or were formed by esterifying carboxylic acids, or that aliphatic acids were formed by hydrolyzing FAMEs. Through extraction and cleanup using this procedure, 17 aromatic acids in eluate were identified and quantified by gas chromatography/tandem mass spectrometry, including five polycyclic aromatic hydrocarbon (PAH): acids 2-naphthoic, biphenyl-4-carboxylic, 9-oxo-9H-fluorene-1-carboxylic, biphenyl-4,4´-dicarboxylic, and phenanthrene-1-carboxylic acid, plus 1,8-naphthalic anhydride. Correlations between the PAH acids and the dicarboxylic and aromatic acids suggested that the first three acids and 1,8-naphthalic anhydride were secondary atmospheric photochemistry products and the last two mainly primary.

Supramolecular hydrogen-bonding networks in bis(adeninium) phthalate phthalic acid 1.45-hydrate.

PubMed

Sridhar, Balasubramanian; Ravikumar, Krishnan

2007-04-01

In the title compound, 2C(5)H(6)N(5)(+).C(8)H(4)O(4)(2-).C(8)H(6)O(4).1.45H(2)O, the asymmetric unit comprises two adeninium cations, two half phthalate anions with crystallographic C(2) symmetry, one neutral phthalic acid molecule, and one fully occupied and one partially occupied site (0.45) for water molecules. The adeninium cations form N-H...O hydrogen bonds with the phthalate anions. The cations also form infinite one-dimensional polymeric ribbons via N-H...N interactions. In the crystal packing, hydrogen-bonded columns of cations, anions and phthalate anions extend parallel to the c axis. The water molecules crosslink adjacent columns into hydrogen-bonded layers.

Identification of intentionally and non-intentionally added substances in plastic packaging materials and their migration into food products.

PubMed

García Ibarra, Verónica; Rodríguez Bernaldo de Quirós, Ana; Paseiro Losada, Perfecto; Sendón, Raquel

2018-05-07

Plastic materials are widely used in food packaging applications; however, there is increased concern because of the possible release of undesirable components into foodstuffs. Migration of plastic constituents not only has the potential to affect product quality but also constitutes a risk to consumer health. In order to check the safety of food contact materials, analytical methodologies to identify potential migrants are required. In the first part of this work, a GC/MS screening method was developed for the identification of components from plastic packaging materials including intentionally and "non-intentionally added substances" (NIAS) as potential migrants. In the second part of this study, the presence of seven compounds (bis (2-ethylhexyl) phthalate (DEHP), diethyl phthalate (DEP), diisobutyl phthalate (DIBP), dibutyl phthalate (DBP), butylated hydroxytoluene (BHT), acetyl tributyl citrate (ATBC), benzophenone (BP)) previously identified in packaging materials were investigated in food products (corn and potatoes snacks, cookies, and cakes). For this purpose, a suitable extraction method was developed and quantification was performed using GC-MS. The developed method was validated in terms of linearity, recovery, repeatability, and limits of detection and quantification. The spiked recoveries varied between 82.7 and 116.1%, and relative standard deviation (RSD) was in the range of 2.22-15.9%. The plasticizer ATBC was the most detected compound (94% samples), followed by DEP (65%), DEHP (47%), BP (44%), DBP (35%), DIBP (21%), and BHT (12%). Regarding phthalates, DEP and DEHP were the most frequently detected compounds in concentrations up to 1.44 μg g -1 . In some samples, only DBP exceeded the European SML of 0.3 mg kg -1 established in Regulation 10/2011. Graphical abstract Chemical migration from plastic packaging into food.

Pregnancy urinary phthalate metabolite concentrations and gestational diabetes risk factors

PubMed Central

James-Todd, TM; Meeker, JD; Huang, T; Hauser, R; Ferguson, KK; Rich-Edwards, JW; McElrath, TF; Seely, EW

2016-01-01

Background Epidemiologic studies suggest phthalate metabolite concentrations are associated with type 2 diabetes. GDM is a strong risk factor for type 2 diabetes. Little is known about phthalates and GDM risk factors (i.e. 1st trimester body mass index (BMI), gestational weight gain (GWG), and 2nd trimester glucose levels). Methods A total of 350 women participating in Lifecodes pregnancy cohort (Boston, MA), delivered at term and had pregnancy urinary phthalate metabolite concentrations. Nine specific gravity-adjusted urinary phthalate metabolites were evaluated. General linear regression was used to assess associations between quartiles of phthalate metabolites and continuous 1st trimester BMI and late 2nd trimester blood glucose. Linear mixed models were used for total GWG. Multivariable logistic regression was used for phthalate concentrations and categorized GWG and impaired glucose tolerance defined as glucose ≥ 140mg/dL based on a 50-gram glucose load test. Models were adjusted for potential confounders. Results There were no associations between 1st trimester urinary phthalate metabolite concentrations and 1st trimester BMI. Mono-ethyl phthalate (MEP) concentrations averaged across pregnancy were associated with a 2.17 increased odds of excessive GWG (95% CI: 0.98, 4.79). Second trimester MEP was associated with an increased odds of impaired glucose tolerance (adj. OR: 7.18; 95% CI: 1.97, 26.15). Di-2-ethylhexyl phthalate metabolite concentrations were inversely associated with impaired glucose tolerance (adj. OR: 0.25; adj. 95% CI: 0.08, 0.85). Conclusions Higher exposure to di-ethyl phthalate, the parent compound of MEP, may be associated with excessive GWG and impaired glucose tolerance; higher di-2-ethylhexyl phthalate was associated with reduced odds of impaired glucose tolerance. PMID:27649471

Characterization of PM2.5 in Guangzhou, China: uses of organic markers for supporting source apportionment.

PubMed

Wang, Jingzhi; Ho, Steven Sai Hang; Ma, Shexia; Cao, Junji; Dai, Wenting; Liu, Suixin; Shen, Zhenxing; Huang, Rujin; Wang, Gehui; Han, Yongming

2016-04-15

Organic carbon (OC), elemental carbon (EC), and non-polar organic compounds including n-alkanes (n-C14-n-C40), polycyclic aromatic hydrocarbons (PAHs), phthalate esters (PAEs) and hopanes were quantified in fine particulate (PM2.5), which were collected in urban area of Guangzhou, China in winter and summer in 2012/2013. The pollutants levels were well comparable with the data obtained in previous studies in Pearl River Delta (PRD) region but much lower than most northern Chinese megacities. The contribution of EC to PM2.5 and OC/EC ratio suggest that the pollution sources were relatively consistent in GZ between the two seasons. Benzo[a]pyrene (BaP) was the most abundant PAHs, which were 4.9 and 1.0ng/m(3) on average, accounting for 10.7% and 9.1% to the total quantified PAHs in winter and summer, respectively. The total concentrations of PAEs ranged from 289.1 to 2435ng/m(3) and from 102.4 to 1437ng/m(3), respectively, in winter and summer. Di-n-butyl phthalate (DBP) was the most dominant PAEs. The ambient levels of PAEs could be partly attributed to the widespread uses of the household products, municipal garbage compressing, sewage, and external painting material on the building. Source apportionment for OC with chemical mass balance (CMB) model demonstrated coal combustion, vehicle emission, cooking, and secondary organic compounds (SOC) formation were the four major pollution sources. Both of the indices of n-alkanes and diagnostic PAHs ratios support that anthropogenic sources such as vehicle emission and coal combustion were the significant pollution sources with some extents from epicuticular waxes by terrestrial plants. The ratio of hopanes to EC proved the influences from vehicle emission, and displayed a certain degree of the air aging in the Guangzhou ambient air. Copyright © 2016 Elsevier B.V. All rights reserved.

Trends in Exposure to Chemicals in Personal Care and Consumer Products.

PubMed

Calafat, Antonia M; Valentin-Blasini, Liza; Ye, Xiaoyun

2015-12-01

Synthetic organic chemicals can be used in personal care and consumer products. Data on potential human health effects of these chemicals are limited-sometimes even contradictory-but because several of these chemicals are toxic in experimental animals, alternative compounds are entering consumer markets. Nevertheless, limited information exists on consequent exposure trends to both the original chemicals and their replacements. Biomonitoring (measuring concentrations of chemicals or their metabolites in people) provides invaluable information for exposure assessment. We use phthalates and bisphenol A-known industrial chemicals-and organophosphate insecticides as case studies to show exposure trends to these chemicals and their replacements (e.g., other phthalates, non-phthalate plasticizers, various bisphenols, pyrethroid insecticides) among the US general population. We compare US trends to national trends from Canada and Germany. Exposure to the original compounds is still prevalent among these general populations, but exposures to alternative chemicals may be increasing.

A multi-residue method for characterization of endocrine disruptors in gaseous and particulate phases of ambient air

NASA Astrophysics Data System (ADS)

Alliot, Fabrice; Moreau-Guigon, Elodie; Bourges, Catherine; Desportes, Annie; Teil, Marie-Jeanne; Blanchard, Martine; Chevreuil, Marc

2014-08-01

A number of semi-volatile compounds occur in indoor air most of them being considered as potent endocrine disruptors and thus, exerting a possible impact upon health. To assess their concentration levels in indoor air, we developed and validated a method for sampling and multi-residue analysis of 58 compounds including phthalates, polycyclic aromatic hydrocarbons (PAHs), polybromodiphenylethers (PBDEs), polychlorobiphenyls (PCBs), parabens, bisphenol A (BPA) and tetrabromobisphenol A (TBBPA) in gaseous and particulate phases of air. We validated each step of procedures from extraction until analysis. Matrice spiking were performed at extraction, fractionation and purification stages. The more volatile compounds were analyzed with a gas chromatography system coupled with a mass spectrometer (GC/MS) or with a tandem mass spectrometer (GC/MS/MS). The less volatile compounds were analyzed with a liquid chromatography system coupled with a tandem mass spectrometer (LC/MS/MS). Labeled internal standard method was used ensuring high quantification accuracy. The instrumental detection limits were under 1 pg for all compounds and therefore, a limit of quantification averaging 1 pg m-3 for the gaseous and the particulate phases and a volume of 150 m3, except for phthalates, phenol compounds and BDE-209. Satisfactory recoveries were found except for phenol compounds. That method was successfully applied to several indoor air samples (office, apartment and day nursery) and most of the targeted compounds were quantified, mainly occurring in the gaseous phase. The most abundant were phthalates (up to 918 ng m-3 in total air), followed by PCBs > parabens > BPA > PAHs > PBDEs.

Effects of mixtures of phthalates and other toxicants on sexual differentiaion in rats: A risk assessment framework based upon disruption of common developing systems

EPA Science Inventory

PE are a large family of compounds used in a wide array of consumer, industrial and medical products. Studies have shown that in utero treatment with PE such as diethyl hexyl phthalate (DEHP) during the critical period of fetal reproductive development produced male reproductive ...

Effects of In Utero Exposure to Di-n-Butyl Phthalate on Testicular Development in Rat

PubMed Central

Ma, Tan; Yin, Xiaoqin; Han, Ruitong; Ding, Jie; Zhang, Huan; Han, Xiaodong

2017-01-01

Humans are inevitably exposed to ubiquitous phthalate esters (PAEs). In utero exposure to di-n-butyl phthalate (DBP) induces abnormal development of the testis and reproductive tract in male offspring, which correspond closely with the human condition of testicular dysgenesis syndrome (TDS)-like syndrome. However, the underlying mechanisms have not been elucidated in detail. In this study, pregnant rats were orally exposed to either corn oil (controls) or DBP at three different doses by gavage during Gestational Days 12.5–21.5. Pathological examinations were performed for toxicity evaluation. Proliferation and apoptosis related proteins (ras related dexamethasone induced 1 (Rasd1), mitogen-activated protein kinase kinases1/2 (MEK1/2), Bcl-2, and Bax) were measured for mechanisms exploration. The results showed that different doses of DBP caused male developmental and reproductive toxicity in rats, including the decrease of anogenital distance (AGD), the histological damage of testis, and apoptosis of seminiferous tubule cells. Our data suggested that DBP played chronic and continuous toxic roles on male reproductive system by disrupting expression of Rasd1 and MEK1/2 as well as Bcl-2/Bax ratio. Further research is warranted. PMID:29064414

Research on the degradation mechanism of dimethyl phthalate in drinking water by strong ionization discharge

NASA Astrophysics Data System (ADS)

Hong, ZHAO; Chengwu, YI; Rongjie, YI; Huijuan, WANG; Lanlan, YIN; I, N. MUHAMMAD; Zhongfei, MA

2018-03-01

The degradation mechanism of dimethyl phthalate (DMP) in the drinking water was investigated using strong ionization discharge technology in this study. Under the optimized condition, the degradation efficiency of DMP in drinking water was up to 93% in 60 min. A series of analytical techniques including high-performance liquid chromatography, liquid chromatography mass spectrometry, total organic carbon analyzer and ultraviolet-visible spectroscopy were used in the study. It was found that a high concentration of ozone (O3) produced by dielectric barrier discharge reactor was up to 74.4 mg l-1 within 60 min. Tert-butanol, isopropyl alcohol, carbonate ions ({{{{CO}}}3}2-) and bicarbonate ions ({{{{HCO}}}3}-) was added to the sample solution to indirectly prove the presence and effect of hydroxyl radicals (·OH). These analytical findings indicate that mono-methyl phthalate, phthalic acid (PA) and methyl ester PA were detected as the major intermediates in the process of DMP degradation. Finally, DMP and all products were mineralized into carbon dioxide (CO2) and water (H2O) ultimately. Based on these analysis results, the degradation pathway of DMP by strong ionization discharge technology were proposed.

Impacts of dimethyl phthalate on the bacterial community and functions in black soils

PubMed Central

Wang, Zhi-Gang; Hu, Yun-Long; Xu, Wei-Hui; Liu, Shuai; Hu, Ying; Zhang, Ying

2015-01-01

Dimethyl phthalate (DMP), a known endocrine disruptor and one of the phthalate esters (PAEs), is a ubiquitous pollutant. Its impacts on living organisms have aroused great concern. In this study, the impacts of DMP contamination on bacterial communities and functions were tested by using microcosm model in black soils. The results showed that the operational taxonomic unit (OTUs) richness and bacterial diversity were reduced by DMP contamination. The relative percentages of some genera associated with nitrogen metabolism were increased by DMP contamination, while the relative percentages of some other genera that were extremely beneficial to soil health were decreased by DMP contamination. Further, the relative percentages of some genera that possessed the capability to degrade DMP were increased by the DMP treatment at low concentrations (5, 10, and 20 mg/kg), but were decreased by the high concentration DMP treatment (40 mg/kg). Clearly, DMP contamination changed the bacterial community structure and disturbed the metabolic activity and functional diversity of the microbes in black soils. Our results suggest that DMP pollution can alter the metabolism and biodiversity of black soil microorganisms, thereby directly impact fertility and ecosystem functions. PMID:25999932

Dibutyl Phthalate (DBP)-Induced Apoptosis and Neurotoxicity are Mediated via the Aryl Hydrocarbon Receptor (AhR) but not by Estrogen Receptor Alpha (ERα), Estrogen Receptor Beta (ERβ), or Peroxisome Proliferator-Activated Receptor Gamma (PPARγ) in Mouse Cortical Neurons.

PubMed

Wójtowicz, Anna K; Szychowski, Konrad A; Wnuk, Agnieszka; Kajta, Małgorzata

2017-01-01

Dibutyl phthalate (di-n-butyl phthalate, DBP) is one of the most commonly used phthalate esters. DBP is widely used as a plasticizer in a variety of household industries and consumer products. Because phthalates are not chemically bound to products, they can easily leak out to enter the environment. DBP can pass through the placental and blood-brain barriers due to its chemical structure, but little is known about its mechanism of action in neuronal cells. This study demonstrated the toxic and apoptotic effects of DBP in mouse neocortical neurons in primary cultures. DBP stimulated caspase-3 and LDH activities as well as ROS formation in a concentration (10 nM-100 µM) and time-dependent (3-48 h) manner. DBP induced ROS formation at nanomolar concentrations, while it activated caspase-3 and LDH activities at micromolar concentrations. The biochemical effects of DBP were accompanied by decreased cell viability and induction of apoptotic bodies. Exposure to DBP reduced Erα and Pparγ mRNA expression levels, which were inversely correlated with protein expression of the receptors. Treatment with DBP enhanced Ahr mRNA expression, which was reflected by the increased AhR protein level observed at 3 h after exposure. ERα, ERβ, and PPARγ antagonists stimulated DBP-induced caspase-3 and LDH activities. AhR silencing demonstrated that DBP-induced apoptosis and neurotoxicity are mediated by AhR, which is consistent with the results from DBP-induced enhancement of AhR mRNA and protein expression. Our study showed that AhR is involved in DBP-induced apoptosis and neurotoxicity, while the ERs and PPARγ signaling pathways are impaired by the phthalate.

Unraveling the Relative Importance of Oral and Dermal Contaminant Exposure in Reptiles: Insights from Studies Using the Western Fence Lizard (Sceloporus occidentalis)

PubMed Central

Weir, Scott M.; Talent, Larry G.; Anderson, Todd A.; Salice, Christopher J.

2014-01-01

Despite widespread recognition of significant data deficiencies, reptiles remain a relatively understudied taxon in ecotoxicology. To conduct ecological risk assessments on reptiles frequently requires using surrogate taxa such as birds, but recent research suggests that reptiles have significantly different exposure profiles and toxicant sensitivity. We exposed western fence lizards, Sceloporus occidentalis, to the same quantities of three model chemicals via oral (gavage) and dermal (ventral skin application) exposure for either 24 or 48 hours. Three phthalate esters (di-methyl phthalate [DMP], di-iso-butyl phthalate [DIBP], and di-n-octyl phthalate [DNOP]) were chosen as model chemicals because they represent a gradient of lipophilicity but are otherwise structurally similar. Overall, the more lipophilic phthalates (DIBP and DNOP) were found to have higher concentrations in tissues than the less lipophilic DMP. Significant differences in tissue concentrations between DIBP and DNOP were tissue-dependent, suggesting that delivery to a site of action following exposure is not only a simple function of lipophilicity. In dermal treatments, DMP usually had fewer detections (except in ventral skin samples), suggesting that lipophilicity (log Kow>2) is a requirement for uptake across the skin. In general, tissue residues were greater in oral treatments than dermal treatments (significant in adipose and liver tissue), but differences were driven strongly by differences in DMP which did not appear to be absorbed well across skin. When differences in tissue residue concentrations between oral and dermal exposure did occur, the difference was not drastic. Taken together these results suggest that dermal exposure should be considered in risk assessments for reptilian receptors. Dermal exposure may be an especially important route for reptiles as their ectothermic physiology translates to lower energetic demands and dietary exposure compared to birds and mammals. PMID:24941063

Di-(2-ethylhexyl) phthalate and mono-(2-ethylhexyl) phthalate inhibit growth and reduce estradiol levels of antral follicles in vitro

DOE Office of Scientific and Technical Information (OSTI.GOV)

Gupta, Rupesh K., E-mail: drrupesh@illinois.ed; Singh, Jeffery M., E-mail: jsingh20@illinois.ed; Leslie, Tracie C., E-mail: tleslie2@illinois.ed

2010-01-15

Any insult that affects survival of ovarian antral follicles can cause abnormal estradiol production and fertility problems. Phthalate esters (PEs) are plasticizers used in a wide range of consumer and industrial products. Exposure to these chemicals has been linked to reduced fertility in humans and animal models. Di-(2-ethylhexyl) phthalate (DEHP) and mono-(2-ethylhexyl) phthalate (MEHP) decrease serum estradiol levels and aromatase (Arom) expression, prolong estrous cycles, and cause anovulation in animal and culture models. These observations suggest PEs directly target antral follicles. We therefore tested the hypothesis that DEHP (1-100 mug/ml) and MEHP (0.1-10 mug/ml) directly inhibit antral follicular growth andmore » estradiol production. Antral follicles from adult mice were cultured with DEHP or MEHP, and/or estradiol for 96 h. During culture, follicle size was measured every 24 h as a measurement of follicle growth. After culture, media were collected for measurement of estradiol levels and follicles were subjected to measurement of cylin-D-2 (Ccnd2), cyclin-dependant-kinase-4 (Cdk4), and Arom. We found that DEHP and MEHP inhibited growth of follicles and decreased estradiol production compared to controls at the highest doses. DEHP and MEHP also decreased mRNA expression of Ccnd2, Cdk4, and Arom at the highest dose. Addition of estradiol to the culture medium prevented the follicles from DEHP- and MEHP-induced inhibition of growth, reduction in estradiol levels, and decreased Ccnd2 and Cdk4 expression. Collectively, our results indicate that DEHP and MEHP may directly inhibit antral follicle growth via a mechanism that partially includes reduction in levels of estradiol production and decreased expression of cell cycle regulators.« less

Endocrine Disruptors and Childhood Social Impairment

PubMed Central

Miodovnik, Amir; Engel, Stephanie M.; Zhu, Chenbo; Ye, Xiaoyun; Soorya, Latha V.; Silva, Manori J.; Calafat, Antonia M.; Wolff, Mary S.

2011-01-01

Prenatal exposure to endocrine disruptors has the potential to impact early brain development. Neurodevelopmental toxicity in utero may manifest as psychosocial deficits later in childhood. This study investigates prenatal exposure to two ubiquitous endocrine disruptors, the phthalate esters and bisphenol A (BPA), and social behavior in a sample of adolescent inner-city children. Third trimester urines of women enrolled in the Mount Sinai Children's Environmental Health Study between 1998 and 2002 (n = 404) were analyzed for phthalate metabolites and BPA. Mother-child pairs were asked to return for a follow-up assessment when the child was between the ages of 7 to 9 years. At this visit, mothers completed the Social Responsiveness Scale (SRS) (n = 137), a quantitative scale for measuring the severity of social impairment related to Autistic Spectrum Disorders (ASD) in the general population. In adjusted general linear models increasing log-transformed low molecular weight phthalate (LMW) metabolite concentrations were associated with greater social deficits (β = 1.53, 95% CI 0.25-2.8). Among the subscales, LMWP were also associated with poorer Social Cognition (β = 1.40, 95% CI 0.1-2.7); Social Communication (β = 1.86, 95% CI 0.5-3.2) and Social Awareness (β = 1.25, 95% CI 0.1-2.4), but not for Autistic Mannerisms or Social Motivation. No significant association with BPA was found (β = 1.18, 95% CI: -0.75, 3.11). Prenatal phthalate exposure was associated with childhood social impairment in a multiethnic urban population. Even mild degrees of impaired social functioning in otherwise healthy individuals can have very important adverse effects over a child's lifetime. These results extend our previous finding of atypical neonatal and early childhood behaviors in relation to prenatal phthalate exposure. PMID:21182865

Unraveling the relative importance of oral and dermal contaminant exposure in reptiles: insights from studies using the western fence lizard (Sceloporus occidentalis).

PubMed

Weir, Scott M; Talent, Larry G; Anderson, Todd A; Salice, Christopher J

2014-01-01

Despite widespread recognition of significant data deficiencies, reptiles remain a relatively understudied taxon in ecotoxicology. To conduct ecological risk assessments on reptiles frequently requires using surrogate taxa such as birds, but recent research suggests that reptiles have significantly different exposure profiles and toxicant sensitivity. We exposed western fence lizards, Sceloporus occidentalis, to the same quantities of three model chemicals via oral (gavage) and dermal (ventral skin application) exposure for either 24 or 48 hours. Three phthalate esters (di-methyl phthalate [DMP], di-iso-butyl phthalate [DIBP], and di-n-octyl phthalate [DNOP]) were chosen as model chemicals because they represent a gradient of lipophilicity but are otherwise structurally similar. Overall, the more lipophilic phthalates (DIBP and DNOP) were found to have higher concentrations in tissues than the less lipophilic DMP. Significant differences in tissue concentrations between DIBP and DNOP were tissue-dependent, suggesting that delivery to a site of action following exposure is not only a simple function of lipophilicity. In dermal treatments, DMP usually had fewer detections (except in ventral skin samples), suggesting that lipophilicity (log Kow>2) is a requirement for uptake across the skin. In general, tissue residues were greater in oral treatments than dermal treatments (significant in adipose and liver tissue), but differences were driven strongly by differences in DMP which did not appear to be absorbed well across skin. When differences in tissue residue concentrations between oral and dermal exposure did occur, the difference was not drastic. Taken together these results suggest that dermal exposure should be considered in risk assessments for reptilian receptors. Dermal exposure may be an especially important route for reptiles as their ectothermic physiology translates to lower energetic demands and dietary exposure compared to birds and mammals.

Phthalate metabolites in Norwegian mothers and children: Levels, diurnal variation and use of personal care products.

PubMed

Sakhi, Amrit Kaur; Sabaredzovic, Azemira; Cequier, Enrique; Thomsen, Cathrine

2017-12-01

Exposure to phthalates has been associated with reproductive and developmental toxicity. Data on levels of these compounds in the Norwegian population is limited. In this study, urine samples were collected from 48 mothers and their children in two counties in Norway. Eleven different phthalate metabolites originating from six commonly used phthalates in consumer products were determined. Concentrations of phthalate metabolites were significantly higher in children compared to mothers except for mono-ethyl phthalate (MEP). The mothers provided several urine samples during 24hours (h) and diurnal variation showed that the concentrations in the morning urine samples (24-8h) were significantly higher than at other time-periods for most of the phthalate metabolites. Intraclass correlation coefficients (ICCs) for 24-hour time-period were in the range of 0.49-0.81. These moderate to high ICCs indicate that one spot urine sample can be used to estimate the exposure to phthalates. Since a significant effect of time of day was observed, it is still advisable to standardize the collection time point to reduce the variation. For the mothers, the use of personal care products (PCPs) were less associated with morning urine samples than early day (8-12h) and evening (16-24h) urine samples. The use of perfume and hair products were positively associated with the urinary concentrations of low molecular weight phthalates. Use of shower soap and shampoo were positively associated with urinary concentration of di(2-ethylhexyl) phthalate (DEHP) metabolites. For children, face cream use was positively associated with phthalate metabolites in the morning samples, and hand soap use was negatively associated with concentration of urinary DEHP metabolites in afternoon/evening samples. Since different PCPs were associated with the urinary phthalate metabolites in different time-periods during a day, more than one spot urine sample might be required to study associations between urinary phthalate metabolites and the use of PCPs. Copyright © 2017 Elsevier B.V. All rights reserved.

Potential grape-derived contributions to volatile ester concentrations in wine.

PubMed

Boss, Paul K; Pearce, Anthony D; Zhao, Yanjia; Nicholson, Emily L; Dennis, Eric G; Jeffery, David W

2015-04-29

Grape composition affects wine flavour and aroma not only through varietal compounds, but also by influencing the production of volatile compounds by yeast. C9 and C12 compounds that potentially influence ethyl ester synthesis during fermentation were studied using a model grape juice medium. It was shown that the addition of free fatty acids, their methyl esters or acyl-carnitine and acyl-amino acid conjugates can increase ethyl ester production in fermentations. The stimulation of ethyl ester production above that of the control was apparent when lower concentrations of the C9 compounds were added to the model musts compared to the C12 compounds. Four amino acids, which are involved in CoA biosynthesis, were also added to model grape juice medium in the absence of pantothenate to test their ability to influence ethyl and acetate ester production. β-Alanine was the only one shown to increase the production of ethyl esters, free fatty acids and acetate esters. The addition of 1 mg∙L(-1) β-alanine was enough to stimulate production of these compounds and addition of up to 100 mg∙L(-1) β-alanine had no greater effect. The endogenous concentrations of β-alanine in fifty Cabernet Sauvignon grape samples exceeded the 1 mg∙L(-1) required for the stimulatory effect on ethyl and acetate ester production observed in this study.

Solution for blank and matrix difficulties encountered during phthalate analysis of edible oils by high performance liquid chromatography coupled with tandem mass spectrometry.

PubMed

Vavrouš, Adam; Pavloušková, Jana; Ševčík, Václav; Vrbík, Karel; Čabala, Radomír

2016-07-22

Worldwide production of phthalates has led to their undesirable presence in the food chain. Particularly edible oils have become an area of growing concern owing to numerous reported occurrences of phthalates. The analytical methods used in this field face difficulties associated mainly with matrix complexity or phthalate contamination which this study has aimed to describe and resolve. The proposed procedure consisting of liquid-liquid extraction, solid phase extraction and high performance liquid chromatography coupled with tandem mass spectrometry allowed us to analyze simultaneously 6 individual phthalates and 2 phthalate isomeric mixtures. DSC-18 SPE phase was selected for cleanup owing to the most efficient co-extract removal (assessed using high resolution mass spectrometry). Several sources of phthalate contamination were identified, however, the mobile phase was the most serious. The key improvement was achieved by equipping a contamination trap, a 50-mm reverse phase HPLC column, generating a delay between target and mobile phase peaks of the same compounds. RSDs ranging between 2.4 and 16 % confirm good precision and LOQs between 5.5 and 110μgkg(-1) reflect satisfactory blank management. With up to 19 occurrences in 25 analyzed edible oil samples and levels up to 33mgkg(-1), bis(2-ethylhexyl), diisononyl and diisodecyl phthalates were the most important contaminants. Copyright © 2016 Elsevier B.V. All rights reserved.

Synthesis of Amide and Ester Derivatives of Cinnamic Acid and Its Analogs: Evaluation of Their Free Radical Scavenging and Monoamine Oxidase and Cholinesterase Inhibitory Activities.

PubMed

Takao, Koichi; Toda, Kazuhiro; Saito, Takayuki; Sugita, Yoshiaki

2017-01-01

A series of cinnamic acid derivatives, amides (1-12) and esters (13-22), were synthesized, and structure-activity relationships for antioxidant activity, and monoamine oxidases (MAO) A and B, acetylcholinesterase, and butyrylcholinesterase (BChE) inhibitory activities were analyzed. Among the synthesized compounds, compounds 1-10, 12-18, and rosmarinic acid (23), which contained catechol, o-methoxyphenol or 5-hydroxyindole moieties, showed potent 1,1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity. Compounds 9-11, 15, 17-22 showed potent and selective MAO-B inhibitory activity. Compound 20 was the most potent inhibitor of MAO-B. Compounds 18 and 21 showed moderate BChE inhibitory activity. In addition, compound 18 showed potent antioxidant activity and MAO-B inhibitory activity. In a comparison of the cinnamic acid amides and esters, the amides exhibited more potent DPPH free radical scavenging activity, while the esters showed stronger inhibitory activities against MAO-B and BChE. These results suggested that cinnamic acid derivatives such as compound 18, p-coumaric acid 3,4-dihydroxyphenethyl ester, and compound 20, p-coumaric acid phenethyl ester, may serve as lead compounds for the development of novel MAO-B inhibitors and candidate lead compounds for the prevention or treatment of Alzheimer's disease.

Semivolatile Organic Compounds in Homes: Strategies for Efficient and Systematic Exposure Measurement Based on Empirical and Theoretical Factors

PubMed Central

2014-01-01

Residential exposure can dominate total exposure for commercial chemicals of health concern; however, despite the importance of consumer exposures, methods for estimating household exposures remain limited. We collected house dust and indoor air samples in 49 California homes and analyzed for 76 semivolatile organic compounds (SVOCs)—phthalates, polybrominated diphenyl ethers (PBDEs), polychlorinated biphenyls (PCBs), polycyclic aromatic hydrocarbons (PAHs), and pesticides. Sixty chemicals were detected in either dust or air and here we report 58 SVOCs detected in dust for the first time. In dust, phthalates (bis(2-ethylhexyl) phthalate, benzyl butyl phthalate, di-n-butyl phthalate) and flame retardants (PBDE 99, PBDE 47) were detected at the highest concentrations relative to other chemicals at the 95th percentile, while phthalates were highest at the median. Because SVOCs are found in both gas and condensed phases and redistribute from their original source over time, partitioning models can clarify their fate indoors. We use empirical data to validate air-dust partitioning models and use these results, combined with experience in SVOC exposure assessment, to recommend residential exposure measurement strategies. We can predict dust concentrations reasonably well from measured air concentrations (R2 = 0.80). Partitioning models and knowledge of chemical Koa elucidate exposure pathways and suggest priorities for chemical regulation. These findings also inform study design by allowing researchers to select sampling approaches optimized for their chemicals of interest and study goals. While surface wipes are commonly used in epidemiology studies because of ease of implementation, passive air sampling may be more standardized between homes and also relatively simple to deploy. Validation of passive air sampling methods for SVOCs is a priority. PMID:25488487

Potential toxicity of phthalic acid esters plasticizer: interaction of dimethyl phthalate with trypsin in vitro.

PubMed

Wang, Yaping; Zhang, Guowen; Wang, Langhong

2015-01-14

Dimethyl phthalate (DMP) is widely used as a plasticizer in industrial processes and has been reported to possess potential toxicity to the human body. In this study, the interaction between DMP and trypsin in vitro was investigated. The results of fluorescence, UV–vis, circular dichroism, and Fourier transform infrared spectra along with cyclic voltammetric measurements indicated that the remarkable fluorescence quenching and conformational changes of trypsin resulted from the formation of a DMP–trypsin complex, which was driven mainly by hydrophobic interactions. The molecular docking and trypsin activity assay showed that DMP primarily interacted with the catalytic triad of trypsin and led to the inhibition of trypsin activity. The dimensions of the individual trypsin molecules were found to become larger after binding with DMP by atomic force microscopy imaging. This study offers a comprehensive picture of DMP–trypsin interaction, which is expected to provide insights into the toxicological effect of DMP.

Acute bioassays and hazard evaluation of representative contaminants detected in Great Lakes fish

USGS Publications Warehouse

Passino, Dora R. May; Smith, Stephen B.

1987-01-01

We have provided a hazard ranking for 19 classes of compounds representing many of the nearly 500 organic compounds identified by gas chromatography-mass spectrometry in lake trout (Salvelinus namaycush) and walleye (Stizostedion vitreum vitreum) from the Great Lakes and Lake St. Clair. We initially made a provisional hazard ranking based on available published and unpublished information on aquatic toxicity, bioaccumulation, occurrence and sources. Acute toxicity tests with Daphnia pulex at 17A°C in reconstituted hard water were performed with 30 compounds representative of the 19 classes that were highest in the provisional ranking. The resulting toxicity data, along with information on the compounds' occurrence in Great Lakes fish and their sources, were ranked and weighted and then used in calculating the revised hazard ranking. The 10 most hazardous classes, in descending order, are as follows (values shown are mean 48-h EC50s, in μ/ml): arene halides (e.g., polychlorinated biphenyls, DDT), 0.0011; phthalate esters, 0.133; chlorinated camphenes (toxaphene), 0.0082; polyaromatic hydrocarbons (PAHs; e.g., dimethylnaphthalene) and reduced derivatives, 1.01; chlorinated fused polycyclics (e.g., trans-nonachlor), 0.022; nitrogen-containing compounds (e.g., O-methylhydroxyl-amine), 1.35; alkyl halides (e.g., (bromomethyl)cyclohexene), 10.1; cyclic alkanes (e.g., cyclododecane), 20.9; silicon-containing compounds (e.g., dimethyldiethoxy silane), 1.25; and heterocyclic nitrogen compounds (e.g., nicotine), 2.48. We recommend that chronic bioassays be conducted with fish and invertebrates to determine the sublethal effects of the following classes of compounds, for which few toxicity data are available: PAHs, heterocyclic nitrogen compounds, other nitrogen-containing compounds, alkyl halides, cyclic alkanes and silicon-containing compounds. Information from these types of studies will aid researchers in determining the possible causal role these contaminants play in the decline and reproductive impairment of Great Lakes fish.

Cat serum contamination by phthalates, PCBs, and PBDEs versus food and indoor air.

PubMed

Braouezec, Clélie; Enriquez, Brigitte; Blanchard, Martine; Chevreuil, Marc; Teil, Marie-Jeanne

2016-05-01

A wide variety of endocrine disrupting compounds (EDCs) with semi-volatile properties are emitted to indoor air and, thus, humans might get exposed to these compounds. Pet cats spend the major part of their lifetime at home and might integrate indoor contamination so that they could mirror the human exposure. Three classes of EDCs, polybromodiphenyl ethers (PBDEs), polychlorinated biphenyls (PCBs), and phthalates (PAEs), were simultaneously considered and quantified in the serum of cats (Felis silvestris catus) living in the Paris area (France). The main compound concentrations by decreasing importance order were as follows: for PAEs, di-n-butyl phthalate (79,900 ng L(-1)) next di-iso-butyl phthalate (53,200 ng L(-1)), di-iso-nonyl phthalate (43,800 ng L(-1)), and di-ethylhexyl phthalate (32,830 ng L(-1)); for PCBs, CB153 (1378 ng L(-1)) next CB52 (509 ng L(-1)), CB101 (355 ng L(-1)), CB110 (264 ng L(-1)), and CB118 (165 ng L(-1)); and for PBDEs, BDE 153/154 (35 ng L(-1)) next BDE47 (10.7 ng L(-1)). Total serum concentrations as mean ± standard deviation were 107 ± 98 μg L(-1) for ∑9PAEs, 2799 ± 944 ng L(-1) for ∑19PCBs, and 56 ± 21 ng L(-1) for ∑9BDEs. The three chemical groups were found in cat food: 0.088 ng g(-1) for ∑9BDEs, 1.7 ng g(-1) for ∑19PCBs, and 2292 ng g(-1) for ∑9PAEs and in indoor air: 0.063 ng m(-3) for ∑9BDEs, 1.5 ng m(-3) for ∑19PCBs, and 848 ng m(-3) for ∑9PAEs. Contaminant intake by food ingestion was approximately 100-fold higher than that by indoor air inhalation.

Fate of phthalate esters in municipal wastewater treatment plant and their environmental impact.

PubMed

Kong, Minghao; Song, Yonghui; Zhang, Yizhang; Liu, Ruixia; Wei, Jian; Zheng, Lei

2016-01-01

The fate and distribution of six phthalate esters (PAEs) in a municipal wastewater treatment plant (WWTP) employing an anaerobic/anoxic/oxic (A(2)/O) process were investigated. The process achieved relatively high removal efficiencies of PAEs in the range 55-97%. It illustrated that biotransformation and sludge-adsorption were major elimination pathways by analyzing the mass balance and flux of PAEs. About 83% of ∑PAEs was entirely removed by A(2)/O bioreactors indicating biotransformation is the dominant removal mechanism. PAEs with shorter alkyl chain length and higher water solubility were more biodegradable. Less than 6% of ∑PAEs were removed by excess sludge adsorption. The sludge-adsorption capacity of PAE depends on its hydrophobicity. The levels and fluxes of PAEs were analyzed by monitoring different sites of the receiving river of the WWTP effluent to clarify the potential impact of discharge. Daily flux of PAEs upstream and downstream of the discharging point were 113 kg·d(-1) and 205 kg·d(-1), respectively, which were higher than the effluent devotion value of 6.67 kg·d(-1). It suggested that the emissions from the WWTP appeared to be less than those from the other possible sources, such as potential untreated discharge and surface runoff. Improvement of wastewater collection efficiencies is necessary to eliminate the PAE load in the urban river.

Di (2-ethylhexyl) phthalate exposure during pregnancy disturbs temporal sex determination regulation in mice offspring.

PubMed

Wang, Yongan; Liu, Wei; Yang, Qing; Yu, Mingxi; Zhang, Zhou

2015-10-02

Animal researches and clinical studies have supported the relevance between phthalates exposure and testicular dysgenesis syndrome (TDS). These disorders may comprise common origin in fetal life, especially during sex determination and differentiation, where the mechanism remains unclear. The present study evaluated the disturbances in gene regulatory networks of sex determination in fetal mouse by in utero Di (2-ethylhexyl) phthalate (DEHP) exposure. Temporal expression of key sex determination genes were examined during the critical narrow time window, using whole-mount in situ hybridization and quantitative-PCR. DEHP exposure resulted in significant reduction in mRNA of Sry during sex determination from gestation day (GD) 11.0 to 11.5 in male fetal mice, and the increasing of Sry expression to threshold level on GD 11.5 was delayed. Meanwhile, Gadd45g and Gata4, the upstream genes of Sry, and downstream gene Sox9 were also significantly downregulated in expression. In fetal females, the expression of Wnt4 and beta-catenin were up-regulated by DEHP exposure. Taken together, the results suggest that the potential mechanism of gonadal development disorder by DEHP may origin from repression of important male sex determination signaling pathway, involving Gadd45g → Gata4 → Sry → Sox9. The results would promote a better understanding of the association between phthalate esters (PAEs) exposure and the reductive disorder. Copyright © 2015 Elsevier Ireland Ltd. All rights reserved.

ESTIMATION OF HYDROLYSIS RATE CONSTANTS OF CARBOXYLIC ACID ESTER AND PHOSPHATE ESTER COMPOUNDS IN AQUEOUS SYSTEMS FROM MOLECULAR STRUCTURE BY SPARC

EPA Science Inventory

SPARC (SPARC Performs Automated Reasoning in Chemistry) chemical reactivity models were extended to calculate hydrolysis rate constants for carboxylic acid ester and phosphate ester compounds in aqueous non- aqueous and systems strictly from molecular structure. The energy diffe...

Natural Organochlorines as Precursors of 3-Monochloropropanediol Esters in Vegetable Oils.

PubMed

Tiong, Soon Huat; Saparin, Norliza; Teh, Huey Fang; Ng, Theresa Lee Mei; Md Zain, Mohd Zairey Bin; Neoh, Bee Keat; Md Noor, Ahmadilfitri; Tan, Chin Ping; Lai, Oi Ming; Appleton, David Ross

2018-01-31

During high-temperature refining of vegetable oils, 3-monochloropropanediol (3-MCPD) esters, possible carcinogens, are formed from acylglycerol in the presence of a chlorine source. To investigate organochlorine compounds in vegetable oils as possible precursors for 3-MCPD esters, we tested crude palm, soybean, rapeseed, sunflower, corn, coconut, and olive oils for the presence of organochlorine compounds. Having found them in all vegetable oils tested, we focused subsequent study on oil palm products. Analysis of the chlorine isotope mass pattern exhibited in high-resolution mass spectrometry enabled organochlorine compound identification in crude palm oils as constituents of wax esters, fatty acid, diacylglycerols, and sphingolipids, which are produced endogenously in oil palm mesocarp throughout ripening. Analysis of thermal decomposition and changes during refining suggested that these naturally present organochlorine compounds in palm oils and perhaps in other vegetable oils are precursors of 3-MCPD esters. Enrichment and dose-response showed a linear relationship to 3-MCPD ester formation and indicated that the sphingolipid-based organochlorine compounds are the most active precursors of 3-MCPD esters.

Correlation of Spatio-Temporal Contaminant Distribution, Land Use, and Hydrogeological Factors in the Karst Aquifers of Northern Puerto Rico

NASA Astrophysics Data System (ADS)

Torres Torres, N. I.; Padilla, I. Y.

2015-12-01

Karst aquifers are characterized by caves, springs, and sinkholes, and typified by interconnected fissures, fractures and conduits. These characteristics make these aquifers highly productive, and vulnerable to contamination. Previous studies in the northern karst aquifers of Puerto Rico have shown significant distribution of contaminants, including volatile organic compounds, phthalates and other contaminants of emerging concern, beyond demarked sources of contamination. This study develops spatial-temporal distributions of phthalate contaminants in the karst system of northern Puerto Rico and assesses statistical correlations between hydrogeologic factors and groundwater contamination with phthalates. Geographic Information Systems (GIS) tools and technologies, and statistical models are applied to attain these objectives. Results show that there is an extensive contamination with phthalates that varies with time. Contamination is present in the confined and shallow aquifers. Di-(2-ethylhexyl) phthalate (DEHP) is the most detected contaminant (20.6% of the sites). Diethyl phthalate and and dibutyl phthalate are also detected in 6.7% and 8.24% of the sites, respectively. Phthalates detected as mixtures components are significantly detected in areas of high urban and industrial development. They are also detected in areas within 5 miles of superfund sites and landfills. The results indicate that phthalate contamination is highly related to land use. Statistical models show that the hydraulic conductivity of the aquifers, sinkholes density, and time are significantly related to the presence of phthalates in groundwater. The extensive spatio-temporal contamination suggests that contaminants can persist in the environment for long periods of time, and that land use and hydrogeological factors are important factors contributing to the presence of emerging contaminants in karst systems.

Isolation and Characterization of Esters of Indole-3-Acetic Acid from the Liquid Endosperm of the Horse Chestnut (Aesculus species) 1

PubMed Central

Domagalski, Wojciech; Schulze, Aga; Bandurski, Robert S.

1987-01-01

Esters of indole-3-acetic acid were extracted and purified from the liquid endosperm of immature fruits of various species of the horse chestnut (Aesculus parviflora, A. baumanni, A.pavia rubra, and A. pavia humulis). The liquid endosperm contained, at least 12 chromatographically distinct esters. One of these compounds was purified and characterized as an ester of indole-3-acetic acid and myo-inositol. A second compound was found to be an ester of indole-3-acetic acid and the disaccharide rutinose (glucosyl-rhamnose). A third compound was partially characterized as an ester of indole-3-acetic acid and a desoxyaminohexose. PMID:11539676

Isolation and characterization of esters of indole-3-acetic acid from the liquid endosperm of the horse chestnut (Aesculus species)

NASA Technical Reports Server (NTRS)

Domagalski, W.; Schulze, A.; Bandurski, R. S.

1987-01-01

Esters of indole-3-acetic acid were extracted and purified from the liquid endosperm of immature fruits of various species of the horse chestnut (Aesculus parviflora, A. baumanni, A. pavia rubra, and A. pavia humulis). The liquid endosperm contained, at least 12 chromatographically distinct esters. One of these compounds was purified and characterized as an ester of indole-3-acetic acid and myo-inositol. A second compound was found to be an ester of indole-3-acetic acid and the disaccharide rutinose (glucosyl-rhamnose). A third compound was partially characterized as an ester of indole-3-acetic acid and a desoxyaminohexose.

Degradation of phthalate esters and acetaminophen in river sediments using the electrokinetic process integrated with a novel Fenton-like process catalyzed by nanoscale schwertmannite.

PubMed

Yang, Gordon C C; Huang, Sheng-Chih; Wang, Chih-Lung; Jen, Yu-Sheng

2016-09-01

The main objective of this study was to develop and establish an in situ remediation technology coupling nano-schwertmannite/H2O2 process and electrokinetic (EK) process for the removal of phthalates (PAEs) and acetaminophen in river sediments. Test results are given as follows: (1) injection of nano-schwertmannite slurry and H2O2 (collectively, "novel oxidant") into the anode reservoir would yield ·OH radicals that then will be diffused into the sediment compartment and further transported by the electroosmotic flow and/or electrophoresis from the anode end toward the cathode to degrade PAEs and pharmaceuticals in the sediment if any; (2) an electric potential gradient of 1.5 V cm(-1) would help the removal of PAEs and acetaminophen in the blank test, which no "novel oxidants" was added to the remediation system; (3) the practice of electrode polarity reversal would maintain neutral pH for sediment after remediation; (4) injection of equally divided dose of 10 mL novel oxidant into the anode reservoir and four injection ports on the top of sediment chamber would further enhance the removal efficiency; and (5) an extension of treatment time from 14 d to 28 d is beneficial to the removal efficiency as expected. In comparison, the remediation performance obtained by the EK-assisted nano-SHM/H2O2 oxidation process is superior to that of the batch degradation test, but is comparable with other EK integrated technologies for the treatment of same contaminants. Thus, it is expected that the EK-assisted nano-SHM/H2O2 oxidation process is a viable technology for the removal of phthalate esters and pharmaceuticals from river sediments in large-scale operations. Copyright © 2016 Elsevier Ltd. All rights reserved.

Application of non-ionic surfactant as a developed method for the enhancement of two-phase solvent bar microextraction for the simultaneous determination of three phthalate esters from water samples.

PubMed

Bandforuzi, Samereh Ranjbar; Hadjmohammadi, Mohammad Reza

2018-08-03

The extraction of phthalate esters (PEs) from aqueous matrices using two-phase solvent bar microextraction by organic micellar phase was investigated. A short hollow fiber immobilized with reverse micelles of Brij 35 surfactant in 1-octanol was served as the solvent bar for microextraction. Experimental results show that the extraction efficiency were much higher using two-phase solvent bar microextraction based on non-ionic surfactant than conventional two-phase solvent bar microextraction because of a positive effect of surfactant-containing extraction phase in promoting the partition process by non-ionic intermolecular forces such as polar and hydrophobicity interactions. The nature of the extraction solvent, type and concentration of non-ionic surfactant, extraction time, sample pH, temperature, stirring rate and ionic strength were the effecting parameters which optimized to obtain the highest extraction recovery. Analysis of recovered analytes was carried out with high performance liquid chromatography coupled with ultraviolet detection (HPLC-UV). Under the optimum conditions, linearity was observed in the range of 1-800 ng mL -1 for dimethylphthalate (DMP) and 0.5-800 ng mL -1 for diethylphthalate (DEP) and di-n-butyl phthalate (DBP) with correlation determination values above 0.99 for them. The limits of detection and quantification were ranged from 0.012 to 0.03 ng mL -1 and 0.04-0.1 ng mL -1 , respectively. The ranges of intra-day and inter-day RSD (n = 3) at 20 ng mL -1 of PEs were 1.8-2.1% and 2.1-2.6%, respectively. Results showed that developed method can be a very powerful, innovative and promising sample preparation technique in PEs analysis from environmental and drinking water samples. Copyright © 2018. Published by Elsevier B.V.

Biodegradation tests of mercaptocarboxylic acids, their esters, related divalent sulfur compounds and mercaptans.

PubMed

Rücker, Christoph; Mahmoud, Waleed M M; Schwartz, Dirk; Kümmerer, Klaus

2018-04-17

Mercaptocarboxylic acids and their esters, a class of difunctional compounds bearing both a mercapto and a carboxylic acid or ester functional group, are industrial chemicals of potential environmental concern. Biodegradation of such compounds was systematically investigated here, both by literature search and by experiments (Closed Bottle Test OECD 301D and Manometric Respirometry Test OECD 301F). These compounds were found either readily biodegradable or at least biodegradable to a significant extent. Some related compounds of divalent sulfur were tested for comparison (mercaptans, sulfides, disulfides). For the two relevant monofunctional compound classes, carboxylic acids/esters and mercaptans, literature data were compiled, and by comparison with structurally similar compounds without these functional groups, the influence of COOH/COOR' and SH groups on biodegradability was evaluated. Thereby, an existing rule of thumb for biodegradation of carboxylic acids/esters was supported by experimental data, and a rule of thumb could be formulated for mercaptans. Concurrent to biodegradation, abiotic processes were observed in the experiments, rapid oxidative formation of disulfides (dimerisation of monomercaptans and cyclisation of dimercaptans) and hydrolysis of esters. Some problems that compromise the reproducibility of biodegradation test results were discussed.

Determination of endocrine disrupting compounds and their metabolites in fish bile.

PubMed

Ros, Oihana; Izaguirre, Jon Kepa; Olivares, Maitane; Bizarro, Cristina; Ortiz-Zarragoitia, Maren; Cajaraville, Miren Pilar; Etxebarria, Nestor; Prieto, Ailette; Vallejo, Asier

2015-12-01

This work describes a new methodology for the simultaneous determination of a large variety of emerging and persistent organic compounds and some of their metabolites in fish bile samples. The target compounds were musk fragrances, alkyl phenols, hormones, pesticides, phthalate esters and bisphenol-A, all of them with a known endocrine disrupting effect. To achieve the determination these three steps were optimized: i) an enzymatic hydrolysis of the metabolites to render the unconjugated compounds; ii) the solid phase extraction of the target analytes (Plexa cartridges 200-mg); and, iii) a clean-up of the extracts (Florisil cartridges 1-g). The samples were analyzed by gas-chromatography-mass spectrometry (GC-MS), though the polar fraction required a previous derivatization with O-bis (trimethylsilyl) trifluoroacetamide. Good apparent recoveries (63-122%), repeatability (<20%) and limits of detection (LODs) ranging between 0.04 and 459 ng/mL were obtained. This method was applied to the analysis of the target analytes in bile samples of thicklip grey mullets (Chelon labrosus) from five different populations of the Basque Coast (South East Bay of Biscay) during the period of May-June 2012. The target analytes were found at concentrations ranging from

[Distribution Characteristics and Risk Assessment of Phthalic Acid Esters in Agricultural Products Around the Pearl River Delta. South China].

PubMed

Li, Bin; Wu, Shan; Liang, Jin-ming; Deng, Jie-fan; Wang, Ke; Liang, Wen-li; Zeng, Cai-ming; Peng, Si-qing; Zhang, Tian-bin; Yang, Guo-yi

2016-01-15

In order to investigate and assess the distribution of pathalic acid easters (PAEs) in agricultural products from typical areas of the Pearl River Delta, South China, 131 agricultural products were sampled for determination of 6 PAEs priority pollutants classified by the U. S. EPA by GC-FID. The results showed that the total contents of the PAEs (sigma PAEs) in agricultural products samples ranged from nd to 79.86 mg x kg(-1) and the mean value was 2.84 mg x kg(-1), with the detected ratio of 98.5%. The average concentrations of sigma PAEs in different types of agricultural products were ordered by vegetables (3.03 mg x kg(-1)) > rice (2.52 mg x kg(-1)) > fruits (1.26 mg x kg(-1)). The mean concentration of PAEs distributed in the four typical cities of the Pearl River Delta, and decreased in the sequence of Zhuhai (6.53 mg x kg(-1)) > Dongguan (2.59 mg x kg(-1)) > Huizhou (1.53 mg x kg(-1)) > Zhongshan (1.12 mg x kg(-1)). Di-n-butyl phthalate (DBP), di-(2-ethylhexyl) phthalate (DEHP) and di-n-octyl phthalate (DnOP) contributed more than 90. 8% of the total PAEs in samples, and were the main components of PAEs in agricultural products from the Pearl River Delta, with higher percentage contents and detected ratio. Meanwhile, the average concentrations of sigma PAEs in cabbage mustard, lettuce occurred in Zhuhai and Dongguan cities, followed by lettuce and leaf lettuce in the corresponding DEHP from Zhuhai city, both exceeded the suggested standards in U.S.A. and Europe and were of high health risk. There were significant differences among 14 various vegetables in the contents of the 6 PAEs compounds, and the sigma PAEs contents in cabbage mustard and lettuce as part of leafy vegetables were higher than those in other vegetables, while the lowest were detected in flowering cabbage and edible amaranth. Therefore, the type of vegetables and its growing environment exposed to the atmosphere and soil were the main factors that significantly affected their accumulation of PAEs concentrations.

Condensation of anhydrides or dicarboxylic acids with compounds containing active methylene groups. Part 1: Condensation of phthalic anhydride with acetoacetic and malonic ester

NASA Technical Reports Server (NTRS)

Oshkaya, V. P.; Vanag, G. Y.

1985-01-01

Phthalic anhydride was condensed with acetoacetic ester in acetic anhydride and triethylamine solution, and when phthalyl chloride was reacted with sodium acetoacetic ester compounds were formed of the phthalide and indandione series: phthalylacetoacetic ester and a derivative of indan-1,3-dione which after boiling with hydrochloric acid yielded indan-1,3-dione. Phthalylmalonic ester was obtained from phthalic anhydride and malonic ester in the presence of triethylamine.

Influence of continental organic aerosols to the marine atmosphere over the East China Sea: Insights from lipids, PAHs and phthalates.

PubMed

Kang, Mingjie; Yang, Fan; Ren, Hong; Zhao, Wanyu; Zhao, Ye; Li, Linjie; Yan, Yu; Zhang, Yingjie; Lai, Senchao; Zhang, Yingyi; Yang, Yang; Wang, Zifa; Sun, Yele; Fu, Pingqing

2017-12-31

Total suspended particle (TSP) samples were collected during a marine cruise in the East China Sea from May 18 to June 12, 2014. They were analyzed for solvent extractable organic compounds (lipid compounds, PAHs and phthalates) using gas chromatography/mass spectrometry (GC/MS) to better understand the sources and source apportionment of aerosol pollution in the western North Pacific. Higher concentrations were observed in the terrestrially influenced aerosol samples on the basis of five-day backward air mass trajectories, especially for aerosols collected near coastal areas. Phthalates were found to be the dominant species among these measured compound classes (707±401ngm -3 for daytime and 313±155ngm -3 for nighttime), followed by fatty acids, fatty alcohols, n-alkanes and PAHs. In general, the daytime abundances for these compounds are higher than nighttime, possibly attributable to more intensive anthropogenic activities during the daytime. The factor analysis indicates that biomass burning, fungal activities and fossil fuel combustion maybe the main emission sources for organic aerosols over the East China Sea. This study demonstrates that the East Asian continent can be a natural emitter of biogenic and anthropogenic organics to the marine atmosphere through long-range transport, which controls the chemical composition and concentration of organic aerosols over the East China Sea. Copyright © 2017 Elsevier B.V. All rights reserved.

Exposure to select phthalates and phenols through use of personal care products among Californian adults and their children.

PubMed

Philippat, Claire; Bennett, Deborah; Calafat, Antonia M; Picciotto, Irva Hertz

2015-07-01

Certain phenols and phthalates are used in many consumer products including personal care products (PCPs). We aimed to study the associations between the use of PCPs and urinary concentrations of biomarkers of select phenols and phthalates among Californian adults and their children. As an additional aim we compared phenols and phthalate metabolites concentrations measured in adults and children urine samples collected the same day. Our study relied on a subsample of 90 adult-child pairs participating in the Study of Use of Products and Exposure Related Behavior (SUPERB). Each adult and child provided one to two urine samples in which we measured concentrations of selected phenols and phthalate metabolites. We computed Spearman correlation coefficients to compare concentrations measured in adults and children urine samples collected the same day. We used adjusted linear and Tobit regression models to study the associations between the use of PCPs in the past 24h and biomarker concentrations. Benzophenone-3 and parabens concentrations were higher in adults compared to their children. Conversely children had higher mono-n-butyl phthalate and mono-isobutyl phthalate concentrations. No significant difference was observed for the other compounds. The total number of different PCPs used was positively associated with urinary concentrations of methyl, propyl and butyl parabens and the main metabolite of diethyl phthalate in adults. Among children, the use of a few specific products including liquid soap, hair care products and sunscreen was positively associated with urinary concentrations of some phenols or phthalate metabolites. These results strengthen the body of evidence suggesting that use of PCPs is an important source of exposure to parabens and diethyl phthalate in adults and provide data on exposure to selected phenols and phthalates through use of PCPs in children. Copyright © 2015 Elsevier Inc. All rights reserved.

Exposure to select phthalates and phenols through use of personal care products among Californian adults and their children

PubMed Central

Philippat, Claire; Bennett, Deborah; Calafat, Antonia M.; Picciotto, Irva Hertz

2016-01-01

Introduction Certain phenols and phthalates are used in many consumer products including personal care products (PCPs). Aims We aimed to study the associations between the use of PCPs and urinary concentrations of bio-markers of select phenols and phthalates among Californian adults and their children. As an additional aim we compared phenols and phthalate metabolites concentrations measured in adults and children urine samples collected the same day. Methods Our study relied on a subsample of 90 adult–child pairs participating in the Study of Use of Products and Exposure Related Behavior (SUPERB). Each adult and child provided one to two urine samples in which we measured concentrations of selected phenols and phthalate metabolites. We computed Spearman correlation coefficients to compare concentrations measured in adults and children urine samples collected the same day. We used adjusted linear and Tobit regression models to study the associations between the use of PCPs in the past 24 h and biomarker concentrations. Results Benzophenone-3 and parabens concentrations were higher in adults compared to their children. Conversely children had higher mono-n-butyl phthalate and mono-isobutyl phthalate concentrations. No significant difference was observed for the other compounds. The total number of different PCPs used was positively associated with urinary concentrations of methyl, propyl and butyl parabens and the main metabolite of diethyl phthalate in adults. Among children, the use of a few specific products including liquid soap, hair care products and sunscreen was positively associated with urinary concentrations of some phenols or phthalate metabolites. Discussion These results strengthen the body of evidence suggesting that use of PCPs is an important source of exposure to parabens and diethyl phthalate in adults and provide data on exposure to selected phenols and phthalates through use of PCPs in children. PMID:25929801

Use of external metabolizing systems when testing for endocrine disruption in the T-screen assay

DOE Office of Scientific and Technical Information (OSTI.GOV)

Taxvig, Camilla, E-mail: camta@food.dtu.dk; Olesen, Pelle Thonning; Nellemann, Christine

2011-02-01

Although, it is well-established that information on the metabolism of a substance is important in the evaluation of its toxic potential, there is limited experience with incorporating metabolic aspects into in vitro tests for endocrine disrupters. The aim of the current study was a) to study different in vitro systems for biotransformation of ten known endocrine disrupting chemicals (EDs): five azole fungicides, three parabens and 2 phthalates, b) to determine possible changes in the ability of the EDs to bind and activate the thyroid receptor (TR) in the in vitro T-screen assay after biotransformation and c) to investigate the endogenousmore » metabolic capacity of the GH3 cells, the cell line used in the T-screen assay, which is a proliferation assay used for the in vitro detection of agonistic and antagonistic properties of compounds at the level of the TR. The two in vitro metabolizing systems tested the human liver S9 mix and the PCB-induced rat microsomes gave an almost complete metabolic transformation of the tested parabens and phthalates. No marked difference the effects in the T-screen assay was observed between the parent compounds and the effects of the tested metabolic extracts. The GH3 cells themselves significantly metabolized the two tested phthalates dimethyl phthalate (DMP) and diethyl phthalate (DEP). Overall the results and qualitative data from the current study show that an in vitro metabolizing system using liver S9 or microsomes could be a convenient method for the incorporation of metabolic and toxicokinetic aspects into in vitro testing for endocrine disrupting effects.« less

Occurrence and potential causes of androgenic activities in source and drinking water in China.

PubMed

Hu, Xinxin; Shi, Wei; Wei, Si; Zhang, Xiaowei; Feng, Jianfang; Hu, Guanjiu; Chen, Sulan; Giesy, John P; Yu, Hongxia

2013-09-17

The increased incidences of disorders of male reproductive tract as well as testicular and prostate cancers have been attributed to androgenic pollutants in the environment. Drinking water is one pathway of exposure through which humans can be exposed. In this study, both potencies of androgen receptor (AR) agonists and antagonists were determined in organic extracts of raw source water as well as finished water from waterworks, tap water, boiled water, and poured boiled water in eastern China. Ten of 13 samples of source water exhibited detectable AR antagonistic potencies with AR antagonist equivalents (Ant-AR-EQs) ranging from <15.3 (detection limit) to 140 μg flutamide/L. However, no AR agonistic activity was detected in any source water. All finished water from waterworks, tap water, boiled water, and poured boiled water exhibited neither AR agonistic nor antagonistic activity. Although potential risks are posed by source water, water treatment processes effectively removed AR antagonists. Boiling and pouring of water further removed these pollutants. Phthalate esters (PAEs) including diisobutyl phthalate (DIBP) and dibutyl phthalate (DBP) were identified as major contributors to AR antagonistic potencies in source waters. Metabolites of PAEs exhibited no AR antagonistic activity and did not increase potencies of PAEs when they coexist.

Environmental Exposure to Dioxins, Dibenzofurans, Bisphenol A, and Phthalates in Children with and without Autism Spectrum Disorder Living near the Gulf of Mexico.

PubMed

Rahbar, Mohammad H; Swingle, Hanes M; Christian, MacKinsey A; Hessabi, Manouchehr; Lee, MinJae; Pitcher, Meagan R; Campbell, Sean; Mitchell, Amy; Krone, Ryan; Loveland, Katherine A; Patterson, Donald G

2017-11-21

Environmental exposure to organic endocrine disrupting chemicals, including dioxins, dibenzofurans, bisphenol A (BPA), and phthalates has been associated with neurodevelopmental disorders, including autism spectrum disorder (ASD). We conducted a pilot monitoring study of 30 ASD cases and 10 typically developing (TD) controls ages 2-8 years from communities along the Gulf of Mexico near Alabama, which houses 14 Superfund sites, to assess the concentrations of dioxins and dibenzofurans in serum, and BPA and phthalate ester metabolites in urine. Based on General Linear Models, the lipid- or creatinine-adjusted geometric mean concentrations of the aforementioned chemicals did not differ between the ASD case and TD control groups (all p ≥ 0.27). We compared our findings to the adjusted means as reported by the National Health and Nutrition Examination Survey, survey years 2011-2012, and found that TD controls in our study had lower BPA (59%) and MEHHP (26%) concentrations, higher MBP (50%) concentration, and comparable (<20% difference) MEP, MBZP, MEOHP, and MCPP concentrations. We also conducted a preliminary investigation of dietary exposures and found that the consumption of certain types of fish may be associated with higher OCDD concentrations, and the consumption of soft drinks and juices may be associated with lower BPA and MEOHP concentrations, respectively.

Responses of bacterial community to dibutyl phthalate pollution in a soil-vegetable ecosystem.

PubMed

Kong, Xiao; Jin, Decai; Jin, Shulan; Wang, Zhigang; Yin, Huaqun; Xu, Meiying; Deng, Ye

2018-04-10

Phthalate esters (PAEs) are a type of plasticizer that has aroused great concern due to their mutagenic, teratogenic, and carcinogenic effects, wherefore dibutyl phthalate (DBP) and other PAEs have been listed as priority pollutants. In this study, the impacts of DBP on a soil-vegetable ecosystem were investigated. The results showed that DBP could accumulate within vegetable tissues, and the accumulative effect was enhanced with higher levels of DBP contamination in soils. DBP accumulation also decreased vegetable quality in various ways, including decreased soluble protein content and increased nitrate content. The diversity of bacteria in soils gradually decreased with increasing DBP concentration, while no clear association with endophytic bacteria was observed. Also, the relative abundance, structure, and composition of soil bacterial communities underwent successional change during the DBP degradation period. The variation of bulk soil bacterial community was significantly associated with DBP concentration, while changes in the rhizosphere soil bacteria community were significantly associated with the properties of both soil and vegetables. The results indicated that DBP pollution could increase the health risk from vegetables and alter the biodiversity of indigenous bacteria in soil-vegetable ecosystems, which might further alter ecosystem functions in agricultural fields. Copyright © 2018 Elsevier B.V. All rights reserved.

Distribution of di(2-ethylhexyl) phthalate and products in blood and blood components.

PubMed Central

Rock, G; Labow, R S; Tocchi, M

1986-01-01

In order to impart flexibility, plastic medical devices incorporate liquid plasticizers into their structure. Data from several laboratories, including ours, have shown that these compounds leach from blood bags and tubing during collection of blood, storage of various blood components and during kidney dialysis and cell and plasma apheresis procedures. After the plasticizer di(2-ethylhexyl) phthalate leaches from poly(vinyl chloride) blood packs, it is converted by a plasma enzyme to a more toxic metabolite, mono(2-ethylhexyl) phthalate. Blood fractionation products from outdated plasma contain mono(2-ethylhexyl) phthalate, the highest level being found in normal serum albumin. Recently, we have reported that di(2-ethylhexyl) phthalate actually binds to the red blood cell membrane and reduces its osmotic fragility. Current methods of red cells storage, which permit utilization up to 35 days after collection, are not possible without this membrane stabilization. Platelets are now stored for 5 days in the Fenwal PL 732 polyolefin bag. Although stated to be essentially free of liquid plasticizers, a significant level of leaching from this bag into the extracts of stored platelet concentrates was observed. PMID:3709456

A simple and selective method for determination of phthalate biomarkers in vegetable samples by high pressure liquid chromatography-electrospray ionization-tandem mass spectrometry.

PubMed

Zhou, Xi; Cui, Kunyan; Zeng, Feng; Li, Shoucong; Zeng, Zunxiang

2016-06-01

In the present study, solid-phase extraction cartridges including silica reversed-phase Isolute C18, polymeric reversed-phase Oasis HLB and mixed-mode anion-exchange Oasis MAX, and liquid-liquid extractions with ethyl acetate, n-hexane, dichloromethane and its mixtures were compared for clean-up of phthalate monoesters from vegetable samples. Best recoveries and minimised matrix effects were achieved using ethyl acetate/n-hexane liquid-liquid extraction for these target compounds. A simple and selective method, based on sample preparation by ultrasonic extraction and liquid-liquid extraction clean-up, for the determination of phthalate monoesters in vegetable samples by liquid chromatography/electrospray ionisation-tandem mass spectrometry was developed. The method detection limits for phthalate monoesters ranged from 0.013 to 0.120 ng g(-1). Good linearity (r(2)>0.991) between MQLs and 1000× MQLs was achieved. The intra- and inter-day relative standard deviation values were less than 11.8%. The method was successfully used to determine phthalate monoester metabolites in the vegetable samples. Copyright © 2016 Elsevier Ltd. All rights reserved.

The Reactions of Nitrogen Peroxide with Possible Stabilisers for Propellants

DTIC Science & Technology

1957-03-01

ether Carbamite Phe nyl-be nzyl-ure thane (pure) Cyclohexanyl-urethane Cyclohexano ne Die thyl phthalate Di-isoamyl phthalate Dibutyl oxalate Glycollic...saponification" arises from the presence of phenyl urethane and diphenyl urea; differences in contents of these impurities and of benzyl aniline...nitrogen that is recovered from a product. 4.2.2 Ure are fairly reactive. Triphenylethylurea present with diphenyl - amine in 蠢 compound" leads to a

Extraneous dissolved organic matter enhanced adsorption of dibutyl phthalate in soils: Insights from kinetics and isotherms.

PubMed

Wu, Wei; Sheng, Hongjie; Gu, Chenggang; Song, Yang; Willbold, Sabine; Qiao, Yan; Liu, Guangxia; Zhao, Wei; Wang, Yu; Jiang, Xin; Wang, Fang

2018-08-01

The widespread use of plastic film, especially in agricultural practices, has resulted in phthalic acid esters (PAEs) pollution, which poses risks for greenhouse soils. Application of composted manure is a common agricultural practice that adds extraneous dissolved organic matter (DOM) to the soil, however, the effect of extraneous DOM on the behavior of PAEs in agricultural soil is not clear. Dibutyl phthalate (DBP) was used as a model compound to investigate the effect and mechanism of extraneous DOM on the adsorption kinetics and isotherms of PAEs in two types of soils, through batch experiments and characterization of extraneous DOM and soils using fourier transform infrared spectroscopy (FTIR) and nuclear magnetic resonance (NMR). The equilibrium adsorption amount of DBP in black soil was higher than in red soil regardless of the presence of extraneous DOM, due to the higher organic matter content of black soil. Hydrophobic partition played a dominant role in the DBP adsorption process of soils with and without extraneous DOM. The addition of DOM enhanced the adsorption capacity of DBP through partition in the two soils, especially at high DBP concentrations. Additions of a lower concentration of DOM better enhanced the adsorption effect than the higher concentrated DOM, due to an increase in water solubility of DBP resulted from excessive extraneous DOM in aqueous phase. Differences in mineral composition of soils led to diverse adsorption mechanisms of DBP as affected by additions of extraneous DOM. The FTIR spectra indicated that the intra-molecular and intermolecular hydrogen bond interactions of carboxylic acids, aromatic CC and CO in amides were involved in DBP adsorption in soils. Therefore, addition of DOM may increase adsorption of DBP in soils and thus influence its bioavailability and transformation in soils. Copyright © 2018 Elsevier B.V. All rights reserved.

Investigation of the tracers for plastic-enriched waste burning aerosols

NASA Astrophysics Data System (ADS)

Kumar, Sudhanshu; Aggarwal, Shankar G.; Gupta, Prabhat K.; Kawamura, Kimitaka

2015-05-01

To better identify the tracers for open-waste burning (OWB) aerosols, we have conducted aerosol sampling at 2 landfill sites, i.e., Okhla and Bhalswa in New Delhi. The metals such as, As, Cd, Sb and Sn, which have been observed almost negligible in remote aerosols, are found abundantly in these OWB aerosol samples (n = 26), i.e., 60 ± 65, 41 ± 53, 537 ± 847 and 1325 ± 1218 ng m-3, respectively. Samples (n = 20) collected at urban locations in New Delhi, i.e., at Employees' State Insurance (ESI) hospital and National Physical Laboratory (NPL) also show high abundances of these metals in the particles. Filter samples are also analyzed for water-soluble dicarboxylic acids (C2-C12) and related compounds (oxocarboxylic acids and α-dicarbonyls). Terephthalic acid (tPh) was found to account for more than 77% of total diacids determined in OWB aerosols. However, such a high abundance of tPh is not observed in aerosols collected at urban sites. Instead, phthalic acid (Ph) was found as the third/fourth most abundant diacid (∼3%) following C2 (>70%) and C4 (>12%) in these waste burning influenced urban aerosols. A possible secondary formation pathway of Ph by photo-degradation of phthalate ester (di-2-ethylhexyl phthalate) in plastic-waste burning aerosol is suggested. Ionic composition of OWB aerosols showed that Cl- is the most abundant ion (40 ± 8% of total ions determined). The correlation studies of the potential metals with the organic tracers of garbage burning, i.e., phthalic, isophthalic and terephthalic acids show that especially Sn can be used as marker for tracing the plastic-enriched waste burning aerosols.

The efficacy of an oxidation pond in mineralizing some industrial waste products with special reference to fluorene degradation: A case study

DOE Office of Scientific and Technical Information (OSTI.GOV)

Ahmed, M.T.; Dewedar, A.; Mekki, L.

1999-07-01

The efficacy of the oxidation pond on the outskirts of the 10th of Ramadan, the main industrial city in Egypt, was examined. Samples of wastewater collected from the inlet and the outlet were screened for some priority pollutants. Acenaphethene and fluorene were the most frequently detected polycyclic aromatic hydrocarbons, while dimethyl phthalate was the most frequently detected phthalate ester. The spectrum of pollutants, their concentrations and frequencies were similar in the inlet and the outlet, indicating an inferior mineralization capability of the pond. Several degradative bacterial strains were isolated from the pond and grown on M56 minimal media supplemented withmore » different pollutants as the carbon source. The efficacy of pure and mixed cultures to break down fluorene, the most frequently detected pollutant was examined. Fluorene degradation was fast in the first 10 days, the followed by a slow phase. Mixed culture had a higher rate of fluorene degradation in comparison to pure cultures. High performance liquid chromatography analysis of fluorene degradation showed three degradative metabolites. But GC/MS analysis detected one compound, identified as acetamide. The present work has indicated the poor efficacy of the pond. Lack of primary treatment of industrial effluent at factory level, coupled with shock loads of toxicants that may damage the microorganisms and their degradative capabilities are presumably main factors behind such inferior performance. Moreover, the type of pollutants discharged into the pond tend to fluctuate and change depending on the rate from the factories discharge and work shifts. Such irregular feeding of persistent pollutants may have led to a wash out of specialized strains of bacteria capable to degrade such persistent pollutants.« less

Ultrasound assisted extraction combined with dispersive liquid-liquid microextraction (US-DLLME)-a fast new approach to measure phthalate metabolites in nails.

PubMed

Alves, Andreia; Vanermen, Guido; Covaci, Adrian; Voorspoels, Stefan

2016-09-01

A new, fast, and environmentally friendly method based on ultrasound assisted extraction combined with dispersive liquid-liquid microextraction (US-DLLME) was developed and optimized for assessing the levels of seven phthalate metabolites (including the mono(ethyl hexyl) phthalate (MEHP), mono(2-ethyl-5-hydroxyhexyl) phthalate (5-OH-MEHP), mono(2-ethyl-5-oxohexyl) phthalate (5-oxo-MEHP), mono-n-butyl phthalate (MnBP), mono-isobutyl phthalate (MiBP), monoethyl phthalate (MEP), and mono-benzyl phthalate (MBzP)) in human nails by UPLC-MS/MS. The optimization of the US-DLLME method was performed using a Taguchi combinatorial design (L9 array). Several parameters such as extraction solvent, solvent volume, extraction time, acid, acid concentration, and vortex time were studied. The optimal extraction conditions achieved were 180 μL of trichloroethylene (extraction solvent), 2 mL trifluoroacetic acid in methanol (2 M), 2 h extraction and 3 min vortex time. The optimized method had a good precision (6-17 %). The accuracy ranged from 79 to 108 % and the limit of method quantification (LOQm) was below 14 ng/g for all compounds. The developed US-DLLME method was applied to determine the target metabolites in 10 Belgian individuals. Levels of the analytes measured in nails ranged between <12 and 7982 ng/g. The MEHP, MBP isomers, and MEP were the major metabolites and detected in every sample. Miniaturization (low volumes of organic solvents used), low costs, speed, and simplicity are the main advantages of this US-DLLME based method. Graphical Abstract Extraction and phase separation of the US-DLLME procedure.

Sugar Ester Compounds for Arthropod Control

USDA-ARS?s Scientific Manuscript database

Sugar esters, also known as acyl sugars or polyol esters, are a class of compounds that are internationally recognized as food additives. They are commonly used in bakery goods, drugs, cosmetics, food packaging plastics, and in other applications because of their surfactant and emulsifying properti...

Degradation of Di(2-Ethylhexyl) Phthalate by a Novel Gordonia alkanivorans Strain YC-RL2.

PubMed

Nahurira, Ruth; Ren, Lei; Song, Jinlong; Jia, Yang; Wang, Junhuan; Fan, Shuanghu; Wang, Haisheng; Yan, Yanchun

2017-03-01

One bacterial strain, YC-RL2, isolated from petroleum-contaminated soil, could utilize environmental hormone Di(2-Ethylhexyl) phthalate (DEHP) as a sole carbon source for growth. Strain YC-RL2 was identified as Gordonia alkanivorans by 16S rRNA gene analysis and Biolog tests. The effects of environmental factors which might affect the degrading process were optimized at 30 °C and pH 8.0. Strain YC-RL2 showed superior halotolerance and could tolerate up to 0-5% NaCl in trace element medium supplemented with DEHP, although the DEHP degradation rates slowed as NaCl concentration increased. It also showed an outstanding performance in a wide range of pH (6.0-11.0). Meanwhile, strain YC-RL2 was able to withstand high concentrations of DEHP (from 100 to 800 mg/L), and the degradation rates were all above 94%. The DEHP intermediates were detected by HPLC-MS, and the degradation pathway was deduced tentatively. DEHP was transformed into phthalic acid (PA) via mono (2-ethylhexyl) phthalate (MEHP), and PA was further utilized for growth via benzoic acid (BA). The enzyme expected to catalyze the hydrolysis of MEHP to PA was identified from strain YC-RL2. Further investigation found that the enzyme could catalyze the transformation of a wide range of monoalkyl phthalates to PA. This study is the first report about species G. alkanivorans which could degrade several kinds of phthalic acid esters (PAEs), and indicates its application potential for bioremediation of PAE-polluted sites.

Exposure of Preschool-Age Greek Children (RHEA Cohort) to Bisphenol A, Parabens, Phthalates, and Organophosphates.

PubMed

Myridakis, Antonis; Chalkiadaki, Georgia; Fotou, Marianna; Kogevinas, Manolis; Chatzi, Leda; Stephanou, Euripides G

2016-01-19

Phthalate esters (PEs), bisphenol A (BPA), and parabens (PBs), which are used in numerous consumer products, are known for their endocrine disrupting properties. Organophosphate chemicals (OPs), which form the basis of the majority of pesticides, are known for their neurotoxic activity in humans. All of these chemicals are associated with health problems to which children are more susceptible. Once they enter the human body, PEs, BPA, PBs, and OPs are metabolized and/or conjugated and finally excreted via urine. Hence, human exposure to these substances is examined through a determination of the urinary concentrations of their metabolites. This study assessed the exposure of Greek preschool-age children to PEs, BPA, PBs, and OPs by investigating the urinary levels of seven PEs metabolites, six PBs, BPA, and six dialkyl phosphate metabolites in five-hundred samples collected from 4-year-old children, subjects of the "RHEA" mother-child cohort in Crete, Greece. Daily intake of endocrine disruptors, calculated for 4 year old children, was lower than the corresponding daily intake for 2.5 year old children, which were determined in an earlier study of the same cohort. In some cases the daily intake levels exceeded the U.S. Environmental Protection Agency Tolerable Daily Intake (TDI) values and the EFSA Reference Doses (RfD) (e.g., for di-2-ethyl-hexyl phthalate, 3.6% and 1% of the children exceeded RfD and TDi, respectively). Exposure was linked to three main sources: PEs-BPA to plastic, PBs-diethyl phthalate to personal hygiene products, and OPs to food.

Thermal Decomposition of Methyl Esters in Biodiesel Fuel: Kinetics, Mechanisms and Products

NASA Astrophysics Data System (ADS)

Chai, Ming

Biodiesel continues to enjoy increasing popularity. However, recent studies on carbonyl compounds emissions from biodiesel fuel are inconclusive. Emissions of carbonyl compounds from petroleum diesel fuels were compared to emissions from pure biodiesel fuels and petroleum-biodiesel blends used in a non-road diesel generator. The concentration of total carbonyl compounds was the highest when the engine was idling. The carbonyl emissions, as well as ozone formation potential, from biodiesel fuel blends were higher than those emitted from petroleum diesel fuel. The sulfur content of diesel fuel and the source of biodiesel fuel were not found to have a significant impact on emissions of carbonyl compounds. Mechanism parameters of the thermal decomposition of biodiesel-range methyl esters were obtained from the results of thermal gravimetric analysis (TGA). The overall reaction orders are between 0.49 and 0.71 and the energies of activation are between 59.9 and 101.3 kJ/mole. Methyl esters in air have lower activation energies than those in nitrogen. Methyl linoleate has the lowest activation energy, followed by methyl oleate, and methyl stearate. The pyrolysis and oxidation of the three methyl esters were investigated using a semi-isothermal tubular flow reactor. The profiles of major products versus reaction temperature are presented. In the pyrolysis of methyl stearate, the primary reaction pathway is the decarboxylic reaction at the methyl ester functional group. Methyl oleate's products indicate more reactions on its carbon-carbon double bond. Methyl linoleate shows highest reactivity among the three methyl esters, and 87 products were detected. The oxidation of three methyl esters resulted in more products in all compound classes, and 55, 114, and 127 products were detected, respectively. The oxidation of methyl esters includes decarboxylation on ester group. The methyl ester's carbon chain could be oxidized as a hydrocarbon compound and form oxidized esters and unsaturated esters, which have been observed in methyl ester's oxidation products. The oxidation of methyl stearate, methyl oleate and methyl linoleate produces 16, 28 and 34 types of carbonyl compounds, respectively. The unsaturated methyl ester forms more carbonyl compounds compared to the saturated methyl ester, which indicates the formation of carbonyl compounds might be more related to the unsaturated carbon bond rather than the methyl ester group. Good agreement between results for total carbon (TC) generally has been found, but the organic and elemental carbon (OC and EC) fractions determined by different methods often disagree. Lack of reference materials has impeded progress on method standardization and understanding method biases. As part of this dissertation, uniform carbon distribution for the filter sets is prepared by using a simply aerosol generation and collection method. The relative standard deviations for the mean TC, OC, and EC results reported by the seven laboratories were below 10%, 11% and 12% (respectively). The method of filter generation is generally applicable and reproducible. Depending on the application, different filter loadings and types of OC materials can be employed. Matched filter sets prepared by this approach can be used for determining the accuracy of various OC-EC methods and thereby contribute to method standardization.

Phthalates and alkylphenols in industrial and domestic effluents: case of Paris conurbation (France).

PubMed

Bergé, A; Gasperi, J; Rocher, V; Gras, L; Coursimault, A; Moilleron, R

2014-08-01

Phthalates and alkylphenols are toxics classified as endocrine disrupting compounds (EDCs). They are of particular concern due to their ubiquity and generally higher levels found in the environment comparatively to other EDCs. Industrial and domestic discharges might affect the quality of receiving waters by discharging organic matter and contaminants through treated waters and combined sewer overflows. Historically, industrial discharges are often considered as the principal vector of pollution in urban areas. If this observation was true in the past for some contaminants, no current data are today available to compare the quality of industrial and domestic discharges as regards EDCs. In this context, a total of 45 domestic samples as well as 101 industrial samples were collected from different sites, including 14 residential and 33 industrial facilities. This study focuses more specifically on 4 phthalates and 2 alkylphenols, among the most commonly studied congeners. A particular attention was also given to routine wastewater quality parameters. For most substances, wastewaters from the different sites were heavily contaminated; they display concentrations up to 1200 μg/l for di-(2-ethylhexyl) phthalate and between 10 and 100 μg/l for diethyl phthalate and nonylphenol. Overall, for the majority of compounds, the industrial contribution to the flux of contaminant reaching the wastewater treatment plants ranges between 1 and 3%. The data generated during this work constitutes one of the first studies conducted in Europe on industrial fluxes for a variety of sectors of activity. The study of the wastewater contribution was used to better predict the industrial and domestic contributions at the scale of a huge conurbation heavily urbanized but with a weak industrial cover, illustrated by Paris. Our results indicate that specific investigations on domestic discharges are necessary in order to reduce the release of phthalates and alkylphenols in the sewer systems for such conurbations. Copyright © 2014 Elsevier B.V. All rights reserved.

Phthalate esters and organochlorine pesticides in agricultural soils and vegetables from fast-growing regions: a case study from eastern China.

PubMed

Sun, Jianteng; Pan, Lili; Tsang, Daniel C W; Li, Zhiheng; Zhu, Lizhong; Li, Xiangdong

2018-01-01

The present study investigated phthalate esters (PAEs) and organochlorine pesticides (OCPs) in agricultural soils and vegetables from eastern China. The concentrations of PAEs ranged from 109 to 5560 ng/g in soils and 60.1 to 2390 ng/g in cabbages, with average concentrations of 946 and 601 ng/g, respectively. The concentrations of OCPs ranged from <0.1 to 662 ng/g in soils and <0.1 to 42.8 ng/g in cabbages, with average concentrations of 134 and 11.6 ng/g, respectively. OCPs were mainly in the 0-30 cm surface soil layers, while PAEs could infiltrate in deep soil profiles to 70-80 cm layer. Potential source analysis traced the occurrence of OCPs to both historical application and current usage, whereas building materials and agricultural plastic film were possible input sources of PAEs in the ambient environment. OCPs showed no apparent effect on soil microbial communities, whereas significant negative relationship was observed between PAEs and fungi in soils (R = -0.54, p < 0.01). Human health risk assessment data revealed marginal noncarcinogenic risks and low carcinogenic risks in these soils. Notably, PAEs posed a comparable or higher risk level compared with that of OCPs. This study suggests the need for better regulation on pollution control and management of PAE-elevated sites to protect soil quality and food safety.

The effects of heavy metal ions, phthalates and ochratoxin A on oxidation of carcinogenic aristolochic acid I causing Balkan endemic nephropathy.

PubMed

Barta, Frantisek; Levova, Katerina; Hodek, Petr; Schmeiser, Heinz H; Arlt, Volker M; Stiborova, Marie

2015-01-01

Balkan endemic nephropathy (BEN) is a chronic progressive fibrosis associated with upper urothelial carcinoma (UUC). Aetiology of BEN is still not fully explained. Although carcinogenic aristolochic acid I (AAI) was proven as the major cause of BEN/UUC, this nephropathy is considered to be multifactorial. Hence, we investigated whether other factors considered as potential causes of BEN [a mycotoxin ochratoxin A (OTA), Cd, Pb, Se and As ions and organic compounds (i.e. phthalates) released from lignite deposits in BEN areas] can influence detoxication of AAI, whose concentrations are crucial for BEN development. Oxidation of AAI to 8-hydroxyaristolochic acid I (AAIa) in the presence of Cd, Pb, Se, As ions, dibutylphthalate (DBP), butylbenzylphthalate (BBP), bis(2-ethylhexyl)phthalate (DEHP) and OTA by rat liver microsomes was determined by HPLC. Only OTA, cadmium and selenium ions, and BBP inhibited AAI oxidation by rat liver microsomes. These compounds also inhibited activities of CYP1A1 and/or CYP2C6/11 catalysing AAI demethylation in rat livers. Therefore, these CYP inhibitions can be responsible for a decrease in AAIa formation. When the combined effects of these compounds were investigated, the most efficient inhibition was caused by OTA combined with BBP and selenium ions. The results show low effects of BBP, cadmium and selenium ions, and/or their combinations on AAI detoxication. No effects were produced by the other metal ions (Pb, As) and phthalates DBP and DEHP. This finding suggests that they do not influence AAI-mediated BEN development. In contrast, OTA might influence this process, by inhibition of AAI detoxication.

Identification of Aroma Compounds of Lamiaceae Species in Turkey Using the Purge and Trap Technique

PubMed Central

Sonmezdag, Ahmet Salih; Kelebek, Hasim; Selli, Serkan

2017-01-01

The present research was planned to characterize the aroma composition of important members of the Lamiaceae family such as Salvia officinalis, Lavandula angustifolia and Mentha asiatica. Aroma components of the S. officinalis, L. angustifolia and M. asiatica were extracted with the purge and trap technique with dichloromethane and analyzed with the gas chromatography–mass spectrometry (GC–MS) technique. A total of 23, 33 and 33 aroma compounds were detected in Salvia officinalis, Lavandula angustifolia and Mentha asiatica, respectively including, acids, alcohols, aldehydes, esters, hydrocarbons and terpenes. Terpene compounds were both qualitatively and quantitatively the major chemical group among the identified aroma compounds, followed by esters. The main terpene compounds were 1,8-cineole, sabinene and linalool in Salvia officinalis, Lavandula angustifolia and Mentha asiatica, respectively. Among esters, linalyl acetate was the only and most important ester compound which was detected in all samples. PMID:28231089

Identification of Aroma Compounds of Lamiaceae Species in Turkey Using the Purge and Trap Technique.

PubMed

Sonmezdag, Ahmet Salih; Kelebek, Hasim; Selli, Serkan

2017-02-08

The present research was planned to characterize the aroma composition of important members of the Lamiaceae family such as Salvia officinalis , Lavandula angustifolia and Mentha asiatica . Aroma components of the S. officinalis , L. angustifolia and M. asiatica were extracted with the purge and trap technique with dichloromethane and analyzed with the gas chromatography-mass spectrometry (GC-MS) technique. A total of 23, 33 and 33 aroma compounds were detected in Salvia officinalis , Lavandula angustifolia and Mentha asiatica , respectively including, acids, alcohols, aldehydes, esters, hydrocarbons and terpenes. Terpene compounds were both qualitatively and quantitatively the major chemical group among the identified aroma compounds, followed by esters. The main terpene compounds were 1,8-cineole, sabinene and linalool in Salvia officinalis , Lavandula angustifolia and Mentha asiatica , respectively. Among esters, linalyl acetate was the only and most important ester compound which was detected in all samples.

Synthesis, Characterization and Application of N-Ti/13X/MCM-41 Mesoporous Molecular Sieves.

PubMed

Tao, Hong; Nguyen, Nhat-Thien; Hei, Xiao-Hui; Nguyen, Cong Nguyen; Tsai, Hsiao-Hsin; Chang, I-Cheng; Chang, Chang-Tang

2016-06-01

Di-n-butyl phthalate (DBP) is a type of phthalate ester. In recent years, an increasing number of studies have examined the removal of DBP. In this study we use a composite material of N-Ti/13X/MCM-41, synthesized by nitrogen, molecular sieve 13X, tetrabutyl orthotitanate and tetraethyl orthosilicate as raw materials, CTAB as a structural template and tetrabutyl titanate and urea under hydrothermal conditions. The optimized experimental conditions, such as the amount of material, reaction time, pH value and initial concentration were tested. The surface areas of N-Ti/13X/MCM-41 were found to be 664 m2g(-1). TEM micrographs revealed N-Ti/13X/MCM-41 is consisting of aggregates of spherical particles, similar with standard synthesized MCM-41 (Mobil Composition of Matter No. 41). Through photocatalytic degradation experiments, the optimum degradation efficiency of DBP was more than 90% at a pH 6.0 with catalyst dosing of 0.15 g L(-1).

Highly Functionalized 1,2–Diamino Compounds through Reductive Amination of Amino Acid-Derived β–Keto Esters

PubMed Central

Pérez-Faginas, Paula; Aranda, M. Teresa; García-López, M. Teresa; Infantes, Lourdes; Fernández-Carvajal, Asia; González-Ros, José Manuel; Ferrer-Montiel, Antonio; González-Muñiz, Rosario

2013-01-01

1,2-Diamine derivatives are valuable building blocks to heterocyclic compounds and important precursors of biologically relevant compounds. In this respect, amino acid-derived β–keto esters are a suitable starting point for the synthesis of β,γ–diamino ester derivatives through a two-step reductive amination procedure with either simple amines or α–amino esters. AcOH and NaBH3CN are the additive and reducing agents of choice. The stereoselectivity of the reaction is still an issue, due to the slow imine-enamine equilibria through which the reaction occurs, affording mixtures of diastereoisomers that can be chromatographically separated. Transformation of the β,γ–diamino esters into pyrrolidinone derivatives allows the configuration assignment of the linear compounds, and constitutes an example of their potential application in the generation of molecular diversity. PMID:23308167

Use of external metabolizing systems when testing for endocrine disruption in the T-screen assay.

PubMed

Taxvig, Camilla; Olesen, Pelle Thonning; Nellemann, Christine

2011-02-01

Although, it is well-established that information on the metabolism of a substance is important in the evaluation of its toxic potential, there is limited experience with incorporating metabolic aspects into in vitro tests for endocrine disrupters. The aim of the current study was a) to study different in vitro systems for biotransformation of ten known endocrine disrupting chemicals (EDs): five azole fungicides, three parabens and 2 phthalates, b) to determine possible changes in the ability of the EDs to bind and activate the thyroid receptor (TR) in the in vitro T-screen assay after biotransformation and c) to investigate the endogenous metabolic capacity of the GH3 cells, the cell line used in the T-screen assay, which is a proliferation assay used for the in vitro detection of agonistic and antagonistic properties of compounds at the level of the TR. The two in vitro metabolizing systems tested the human liver S9 mix and the PCB-induced rat microsomes gave an almost complete metabolic transformation of the tested parabens and phthalates. No marked difference the effects in the T-screen assay was observed between the parent compounds and the effects of the tested metabolic extracts. The GH3 cells themselves significantly metabolized the two tested phthalates dimethyl phthalate (DMP) and diethyl phthalate (DEP). Overall the results and qualitative data from the current study show that an in vitro metabolizing system using liver S9 or microsomes could be a convenient method for the incorporation of metabolic and toxicokinetic aspects into in vitro testing for endocrine disrupting effects. Copyright © 2010 Elsevier Inc. All rights reserved.

DOE Office of Scientific and Technical Information (OSTI.GOV)

Reifenrath, W.G.; Hawkins, G.S.; Kurtz, M.S.

Formulations of the mosquito repellent N,N-diethyl-3-methylbenzamide (deet) in combination with a variety of additives were developed to control repellent evaporation and percutaneous penetration. Deet was also formulated with the repellent dimethyl phthalate to study the interaction of the two compounds on the skin. The evaporation and penetration processes were evaluated on whole and split-thickness pig skin using radiolabeled repellents with an in vitro apparatus. Under essentially still air and air flow conditions, one of the deet formulations resulted in significantly reduced total evaporation and percutaneous penetration of deet as compared to unformulated repellent. When deet and dimethyl phthalate were combined,more » neither repellent affected the total amount of evaporation and penetration of the other compound. However, initial percutaneous penetration and evaporation rates were slightly less and decayed less rapidly than when both chemicals were tested separately at the same dose. These results indicated a degree of competition of the two compounds for the same avenues of loss.« less

Dose–response analysis of phthalate effects on gene expression in rat whole embryo culture

DOE Office of Scientific and Technical Information (OSTI.GOV)

Robinson, Joshua F.; Department of Toxicogenomics, Maastricht University, Maastricht; Verhoef, Aart

2012-10-01

The rat postimplantation whole embryo culture (WEC) model serves as a potential screening tool for developmental toxicity. In this model, cultured rat embryos are exposed during early embryogenesis and evaluated for morphological effects. The integration of molecular-based markers may lead to improved objectivity, sensitivity and predictability of WEC in assessing developmental toxic properties of compounds. In this study, we investigated the concentration-dependent effects of two phthalates differing in potency, mono(2-ethylhexyl) phthalate (MEHP) and monomethyl phthalate (MMP, less toxic), on the transcriptome in WEC to examine gene expression in relation with dysmorphogenesis. MEHP was more potent than MMP in inducing genemore » expression changes as well as changes on morphology. MEHP induced significant enrichment of cholesterol/lipid/steroid (CLS) metabolism and apoptosis pathways which was associated with developmental toxicity. Regulation of genes within CLS metabolism pathways represented the most sensitive markers of MEHP exposure, more sensitive than classical morphological endpoints. As shown in direct comparisons with toxicogenomic in vivo studies, alterations in the regulation of CLS metabolism pathways has been previously identified to be associated with developmental toxicity due to phthalate exposure in utero. Our results support the application of WEC as a model to examine relative phthalate potency through gene expression and morphological responses. Additionally, our results further define the applicability domain of the WEC model for developmental toxicological investigations. -- Highlights: ► We examine the effect of two phthalates on gene expression and morphology in WEC. ► MEHP is more potent than MMP in inducing gene expression changes and dysmorphogenesis. ► MEHP significantly disrupts cholesterol metabolism pathways in a dose-dependent manner. ► Specific phthalate-related mechanisms in WEC are relevant to mechanisms in vivo.« less

Phthalates and other additives in plastics: human exposure and associated health outcomes

PubMed Central

Meeker, John D.; Sathyanarayana, Sheela; Swan, Shanna H.

2009-01-01

Concern exists over whether additives in plastics to which most people are exposed, such as phthalates, bisphenol A or polybrominated diphenyl ethers, may cause harm to human health by altering endocrine function or through other biological mechanisms. Human data are limited compared with the large body of experimental evidence documenting reproductive or developmental toxicity in relation to these compounds. Here, we discuss the current state of human evidence, as well as future research trends and needs. Because exposure assessment is often a major weakness in epidemiological studies, and in utero exposures to reproductive or developmental toxicants are important, we also provide original data on maternal exposure to phthalates during and after pregnancy (n = 242). Phthalate metabolite concentrations in urine showed weak correlations between pre- and post-natal samples, though the strength of the relationship increased when duration between the two samples decreased. Phthalate metabolite levels also tended to be higher in post-natal samples. In conclusion, there is a great need for more human studies of adverse health effects associated with plastic additives. Recent advances in the measurement of exposure biomarkers hold much promise in improving the epidemiological data, but their utility must be understood to facilitate appropriate study design. PMID:19528058

Phthalates and type 1 diabetes: is there any link?

PubMed

Castro-Correia, Cíntia; Correia-Sá, Luísa; Norberto, Sónia; Delerue-Matos, Cristina; Domingues, Valentina; Costa-Santos, Cristina; Fontoura, Manuel; Calhau, Conceição

2018-04-21

Phthalates are a group of chemical compounds used as plasticizers in the manufacture of plastic materials. They can be present in many commonly used products. There seems to be a relationship between exposure to phthalates and the occurrence of metabolic dysfunctions, such as a decrease in glucose tolerance, oxidative stress, loss of beta cells, and a decrease in insulin synthesis. As beta cells play a key role in the onset of type 1 diabetes mellitus (T1DM), we sought to investigate the relationship between exposure to phthalates and the diagnosis of T1DM in prepubertal children. Design concentrations of phthalate metabolites were compared in the urine of a population of prepubertal children with new-onset diabetes, patients with T1DM diagnosed more than 6 months previously, and healthy control children. Although the concentrations of DBP and DiBP metabolites were statistically identical in the new-onset diabetes, diabetes, and control groups, there was a clear trend for higher levels of DiBP metabolites in the children with new-onset diabetes. In our sample, there was a trend for higher levels of DiBP metabolites in children with new-onset diabetes.

Copper-catalyzed oxidative C-O bond formation of 2-acyl phenols and 1,3-dicarbonyl compounds with ethers: direct access to phenol esters and enol esters.

PubMed

Park, Jihye; Han, Sang Hoon; Sharma, Satyasheel; Han, Sangil; Shin, Youngmi; Mishra, Neeraj Kumar; Kwak, Jong Hwan; Lee, Cheong Hoon; Lee, Jeongmi; Kim, In Su

2014-05-16

A copper-catalyzed oxidative coupling of 2-carbonyl-substituted phenols and 1,3-dicarbonyl compounds with a wide range of dibenzyl or dialkyl ethers is described. This protocol provides an efficient preparation of phenol esters and enol esters in good yields with high chemoselectivity. This method represents an alternative protocol for classical esterification reactions.

Nanoporous Cyanate Ester Resins: Structure-Gas Transport Property Relationships

NASA Astrophysics Data System (ADS)

Gusakova, Kristina; Fainleib, Alexander; Espuche, Eliane; Grigoryeva, Olga; Starostenko, Olga; Gouanve, Fabrice; Boiteux, Gisèle; Saiter, Jean-Marc; Grande, Daniel

2017-04-01

This contribution addresses the relationships between the structure and gas transport properties of nanoporous thermostable cyanate ester resins (CERs) derived from polycyclotrimerization of 1,1'-bis(4-cyanatophenyl)ethane in the presence of 30 or 50 wt% of inert high-boiling temperature porogens (i.e., dimethyl- or dibutyl phthalates), followed by their quantitative removal. The nanopores in the films obtained were generated via a chemically induced phase separation route with further porogen extraction from the densely crosslinked CERs. To ensure a total desorption of the porogen moieties from the networks, an additional short-term thermal annealing at 250 °C was performed. The structure and morphology of such nanoporous CER-based films were investigated by FTIR and SEM techniques, respectively. Further, the gas transport properties of CER films were analyzed after the different processing steps, and relationships between the material structure and the main gas transport parameters were established.

A Strategy for Nonmigrating Plasticized PVC Modified with Mannich base of Waste Cooking Oil Methyl Ester.

PubMed

Jia, Puyou; Zhang, Meng; Hu, Lihong; Song, Fei; Feng, Guodong; Zhou, Yonghong

2018-01-25

The waste cooking oil (WCO) production from the catering industry and food processing industry causes serious environmental, economic and social problems. However, WCO can be used for the preparation of fine chemicals such as internal plasticizer. With this aim, this work is focused on preparing internal plasticizer by using WCO and determining technical viability of non-migration poly (vinyl chloride) (PVC) materials. The mannich base of waste cooking oil methyl ester (WCOME) was synthesized from WCO via esterification, interesterification and mannich reaction, which was used to produce self-plasticization PVC materials as an internal plasticizer. The results showed that the PVC was plasticized effectively. Self-plasticization PVC films showed no migration in n-hexane, but 15.7% of dioctyl phthalate (DOP) leached from DOP/PVC(50/50) system into n-hexane. These findings transformed the traditional plastic processing technology and obtained cleaner production of no migration plasticizer from WCO.

Survey of the Anaerobic Biodegradation Potential of Organic Chemicals in Digesting Sludge

PubMed Central

Battersby, Nigel S.; Wilson, Valerie

1989-01-01

The degradation potential of 77 organic chemicals under methanogenic conditions was examined with an anaerobic digesting sludge from the United Kingdom. Degradation was assessed in terms of net total gas (CH4 plus CO2) produced, expressed as a percentage of the theoretical production (ThGP). The compounds tested were selected from various chemical groups and included substituted phenols and benzoates, pesticides, phthalic acid esters, homocyclic and heterocyclic ring compounds, glycols, and monosubstituted benzenes. The results obtained were in good agreement with published surveys of biodegradability in U.S. digesting sludges and other methanogenic environments. In general, the presence of chloro or nitro groups inhibited anaerobic gas production, while carboxyl and hydroxyl groups facilitated biodegradation. The relationship between substituent position and susceptibility to methanogenic degradation was compound dependent. The following chemicals were completely degraded (≥80% ThGP) at a concentration of 50 mg of carbon per liter: phenol, 2-aminophenol, 4-cresol, catechol, sodium benzoate, 4-aminobenzoic acid, 3-chlorobenzoic acid, phthalic acid, ethylene glycol, diethylene glycol, triethylene glycol, sodium stearate, and quinoline. 3-Cresol, 4-chlorobenzoic acid, dimethyl phthalate, and pyridine were partially degraded. Although the remaining chemicals tested were either persistent or toxic, their behavior may differ at more environmentally realistic chemical-to-biomass ratios. Our findings suggest that biodegradability assessments made with sludge from one source can be extrapolated to sludge from another source with a reasonable degree of confidence and should help in predicting the fate of an organic chemical during the anaerobic digestion of sewage sludge. PMID:16347851

Downsides of the recycling process: harmful organic chemicals in children's toys.

PubMed

Ionas, Alin C; Dirtu, Alin C; Anthonissen, Tim; Neels, Hugo; Covaci, Adrian

2014-04-01

Most of the materials used in consumer goods contain a number of additives which are meant to improve key properties like plasticity or flame resistance. At the end-of-life of the product, many polymeric materials are recycled and the additives they contain, such as flame retardants (FRs) and plasticizers, are transferred to the newly manufactured goods. We have investigated the occurrence and profiles of FRs, such as polybrominated diphenyl ethers (PBDEs) and phosphate FR (PFRs) and of plasticisers, such as phthalate esters, in 106 toys samples. Low levels and detection frequencies of components of the technical Penta-BDE and Deca-BDE mixtures were found, with BDE 209 being the dominant PBDE in all samples (maximum value was 0.14mg/g or 0.014%). The levels of PFRs and phthalates were up to 10,000 times higher than those of the PBDEs, with triphenyl phosphate and diethylhexyl phthalate being the major representatives of these classes. Maximum values were 1.3 and 6.9%, respectively. The detection frequencies were up to 50% for PFRs and 98% for phthalates. All but one of the toys produced after the REACH regulation went into force complied with its provisions. The samples were grouped according to relevant selection criteria to assess the risk for children of different age groups. Using models in the literature, exposure to these chemicals was tentatively assessed. It is clear that at the levels found in the investigated toys, these additives do not contribute to the intended characteristics of the materials, but in some cases may pose a health hazard to the children. Most likely, recycled materials are an important source of these additives in toys and therefore, their (re)use in products for children should be subject to stricter restrictions. Copyright © 2014 Elsevier Ltd. All rights reserved.

Biodegradation of Di-(2-ethylhexyl) Phthalate by Rhodococcus ruber YC-YT1 in Contaminated Water and Soil.

PubMed

Yang, Ting; Ren, Lei; Jia, Yang; Fan, Shuanghu; Wang, Junhuan; Wang, Jiayi; Nahurira, Ruth; Wang, Haisheng; Yan, Yanchun

2018-05-11

Di-(2-ethylehxyl) phthalate (DEHP) is one of the most broadly representative phthalic acid esters (PAEs) used as a plasticizer in polyvinyl chloride (PVC) production, and is considered to be an endocrine-disrupting chemical. DEHP and its monoester metabolites are responsible for adverse effects on human health. An efficient DEHP-degrading bacterial strain Rhodococcus ruber YC-YT1, with super salt tolerance (0⁻12% NaCl), is the first DEHP-degrader isolated from marine plastic debris found in coastal saline seawater. Strain YC-YT1 completely degraded 100 mg/L DEHP within three days (pH 7.0, 30 °C). According to high-performance liquid chromatography⁻mass spectrometry (HPLC-MS) analysis, DEHP was transformed by strain YC-YT1 into phthalate (PA) via mono (2-ethylehxyl) phthalate (MEHP), then PA was used for cell growth. Furthermore, YC-YT1 metabolized initial concentrations of DEHP ranging from 0.5 to 1000 mg/L. Especially, YC-YT1 degraded up to 60% of the 0.5 mg/L initial DEHP concentration. Moreover, compared with previous reports, strain YC-YT1 had the largest substrate spectrum, degrading up to 13 kinds of PAEs as well as diphenyl, p-nitrophenol, PA, benzoic acid, phenol, protocatechuic acid, salicylic acid, catechol, and 1,2,3,3-tetrachlorobenzene. The excellent environmental adaptability of strain YC-YT1 contributed to its ability to adjust its cell surface hydrophobicity (CSH) so that 79.7⁻95.9% of DEHP-contaminated agricultural soil, river water, coastal sediment, and coastal seawater were remedied. These results demonstrate that R. ruber YC-YT1 has vast potential to bioremediate various DEHP-contaminated environments, especially in saline environments.

Biodegradation of Di-(2-ethylhexyl) Phthalate by Rhodococcus ruber YC-YT1 in Contaminated Water and Soil

PubMed Central

Yang, Ting; Jia, Yang; Fan, Shuanghu; Wang, Junhuan; Wang, Jiayi; Nahurira, Ruth; Wang, Haisheng; Yan, Yanchun

2018-01-01

Di-(2-ethylehxyl) phthalate (DEHP) is one of the most broadly representative phthalic acid esters (PAEs) used as a plasticizer in polyvinyl chloride (PVC) production, and is considered to be an endocrine-disrupting chemical. DEHP and its monoester metabolites are responsible for adverse effects on human health. An efficient DEHP-degrading bacterial strain Rhodococcus ruber YC-YT1, with super salt tolerance (0–12% NaCl), is the first DEHP-degrader isolated from marine plastic debris found in coastal saline seawater. Strain YC-YT1 completely degraded 100 mg/L DEHP within three days (pH 7.0, 30 °C). According to high-performance liquid chromatography–mass spectrometry (HPLC-MS) analysis, DEHP was transformed by strain YC-YT1 into phthalate (PA) via mono (2-ethylehxyl) phthalate (MEHP), then PA was used for cell growth. Furthermore, YC-YT1 metabolized initial concentrations of DEHP ranging from 0.5 to 1000 mg/L. Especially, YC-YT1 degraded up to 60% of the 0.5 mg/L initial DEHP concentration. Moreover, compared with previous reports, strain YC-YT1 had the largest substrate spectrum, degrading up to 13 kinds of PAEs as well as diphenyl, p-nitrophenol, PA, benzoic acid, phenol, protocatechuic acid, salicylic acid, catechol, and 1,2,3,3-tetrachlorobenzene. The excellent environmental adaptability of strain YC-YT1 contributed to its ability to adjust its cell surface hydrophobicity (CSH) so that 79.7–95.9% of DEHP-contaminated agricultural soil, river water, coastal sediment, and coastal seawater were remedied. These results demonstrate that R. ruber YC-YT1 has vast potential to bioremediate various DEHP-contaminated environments, especially in saline environments. PMID:29751654

Dose additive effects of simvastatin and dipentyl phthalate on ...

EPA Pesticide Factsheets

Sex differentiation of the mammalian reproductive tract is a highly regulated process that is driven, in part, by fetal testosterone (T) production. In utero exposure to phthalate esters (PE) during sex differentiation can cause reproductive tract malformations in rats. PE alter the expression of genes associated with steroid synthesis/transport and cholesterol biosynthesis. Simvastatin (SMV) is a cholesterol-lowering drug that inhibits HMG-CoA reductase. As cholesterol is a precursor for steroid biosynthesis, we proposed that maternal exposure to SMV during the critical period of sex differentiation would lower fetal T and result in corresponding alterations in cholesterol- and androgenmediated gene expression. Timed pregnant SD rats were dosed orally with SMV from GD14-GD18. T production on GD18 was measured by RIA, and changes in gene expression in maternal and fetal tissues were assessed by quantitative rt-PCR. Circulating lipids were also measured in dams and fetuses. SMV lowered fetal T production, altered several genes involved in cholesterol biosynthesis in the maternal liver, and lowered lipids in the fetus but not in the dam. Unlike PE, SMV did not alter genes associated with sex differentiation. In a second experiment, dams were dosed with SMV, dipentyl phthalate (DPeP, a PE), or both. SMV and DPeP alone reduced fetal T production to 44.3 and 37.5% of control values, respectively, but the mixture reduced T production to 19.9% of control. These studies

Environmental Exposure to Dioxins, Dibenzofurans, Bisphenol A, and Phthalates in Children with and without Autism Spectrum Disorder Living near the Gulf of Mexico

PubMed Central

Rahbar, Mohammad H.; Swingle, Hanes M.; Christian, MacKinsey A.; Hessabi, Manouchehr; Lee, MinJae; Pitcher, Meagan R.; Campbell, Sean; Mitchell, Amy; Krone, Ryan; Loveland, Katherine A.; Patterson, Donald G.

2017-01-01

Environmental exposure to organic endocrine disrupting chemicals, including dioxins, dibenzofurans, bisphenol A (BPA), and phthalates has been associated with neurodevelopmental disorders, including autism spectrum disorder (ASD). We conducted a pilot monitoring study of 30 ASD cases and 10 typically developing (TD) controls ages 2–8 years from communities along the Gulf of Mexico near Alabama, which houses 14 Superfund sites, to assess the concentrations of dioxins and dibenzofurans in serum, and BPA and phthalate ester metabolites in urine. Based on General Linear Models, the lipid- or creatinine-adjusted geometric mean concentrations of the aforementioned chemicals did not differ between the ASD case and TD control groups (all p ≥ 0.27). We compared our findings to the adjusted means as reported by the National Health and Nutrition Examination Survey, survey years 2011–2012, and found that TD controls in our study had lower BPA (59%) and MEHHP (26%) concentrations, higher MBP (50%) concentration, and comparable (<20% difference) MEP, MBZP, MEOHP, and MCPP concentrations. We also conducted a preliminary investigation of dietary exposures and found that the consumption of certain types of fish may be associated with higher OCDD concentrations, and the consumption of soft drinks and juices may be associated with lower BPA and MEOHP concentrations, respectively. PMID:29160842

Effects of gestational exposure to di-n-butyl phthalate and mineral oil on testis development of the Mongolian gerbil.

PubMed

Christante, C M; Pinto-Fochi, M E; Negrin, A C; Taboga, S R; Góes, R M

2018-06-14

Phthalate esters are endocrine disrupters that can affect the development of the testis in a species-specific manner. However, their interference in the male gonads of the Mongolian gerbil is unknown. The aim of the present study was to evaluate whether gestational exposure to di-n-butyl phthalate (DBP) interferes with the development of the gerbil testis during the first six weeks of life. Males were evaluated at 1, 7, 14, 28, 35 and 42 days of age in an untreated (control) group or groups exposed from 8 to 23 days gestation to DBP (100mgkg-1day-1 in mineral oil) or vehicle by maternal gavage. DBP exposure impaired cell proliferation within the seminiferous cords at birth, but increased proliferation at the end of the first week, when higher testosterone concentrations were observed. The vehicle (mineral oil) reduced the total number of gonocytes and attenuated the decrease in testosterone concentrations at 7 days. The vehicle also altered gonocyte relocation at 14 days and increased oestrogen concentrations at 28 days by approximately 112%. In summary, both DBP and oil interfered in gonadal development and testosterone plasma concentrations in the first week of postnatal life. However, the changes observed at the beginning of puberty were not seen after exposure to DBP, indicating a more harmful effect of mineral oil in this period.

Naturally Occurring Cinnamic Acid Sugar Ester Derivatives.

PubMed

Tian, Yuxin; Liu, Weirui; Lu, Yi; Wang, Yan; Chen, Xiaoyi; Bai, Shaojuan; Zhao, Yicheng; He, Ting; Lao, Fengxue; Shang, Yinghui; Guo, Yu; She, Gaimei

2016-10-24

Cinnamic acid sugar ester derivatives (CASEDs) are a class of natural product with one or several phenylacrylic moieties linked with the non-anomeric carbon of a glycosyl skeleton part through ester bonds. Their notable anti-depressant and brains protective activities have made them a topic of great interest over the past several decades. In particular the compound 3',6-disinapoylsucrose, the index component of Yuanzhi (a well-known Traditional Chinese Medicine or TCM), presents antidepressant effects at a molecular level, and has become a hotspot of research on new lead drug compounds. Several other similar cinnamic acid sugar ester derivatives are reported in traditional medicine as compounds to calm the nerves and display anti-depression and neuroprotective activity. Interestingly, more than one third of CASEDs are distributed in the family Polygalaceae . This overview discusses the isolation of cinnamic acid sugar ester derivatives from plants, together with a systematic discussion of their distribution, chemical structures and properties and pharmacological activities, with the hope of providing references for natural product researchers and draw attention to these interesting compounds.

Solid-phase microextraction of phthalate esters in water sample using different activated carbon-polymer monoliths as adsorbents.

PubMed

Lirio, Stephen; Fu, Chung-Wei; Lin, Jhih-Yun; Hsu, Meng-Ju; Huang, Hsi-Ya

2016-07-13

In this study, the application of different activated carbon-polymer (AC-polymer) monoliths as adsorbents for the solid-phase microextraction (SPME) of phthalate esters (PAEs) in water sample were investigated. The activated carbon (AC) was embedded in organic polymers, poly(butyl methacrylate-co-ethylene dimethacrylate) (poly(BMA-EDMA)) or poly(styrene-co-divinylbenzene) (poly(STY-DVB)), via a 5-min microwave-assisted or a 15-min water bath heating polymerization. Preliminary investigation on the performance of the native poly(BMA-EDMA) and poly(STY-DVB) demonstrated remarkable adsorption efficiencies for PAEs. However, due to the strong hydrophobic, π-π, and hydrogen bonding interactions between the analytes and polymers, low extraction recoveries were achieved. In contrast, the presence of AC in native polymers not only enhanced the adsorption efficiencies but also assisted the PAE desorption, especially for AC-poly(STY-DVB) with extraction recovery ranged of 76.2-99.3%. Under the optimized conditions, the extraction recoveries for intra-, inter-day and column-to-column were in the range of 76.5-100.8% (<3.7% RSDs), 77.2-97.6% (<5.6% RSDs) and 75.5-99.7% (<6.2% RSDs), respectively. The developed AC-poly(STY-DVB) monolithic column showed good mechanical stability, which can be reused for more than 30 extraction times without any significant loss in the extraction recoveries of PAEs. The AC-poly(STY-DVB) monolithic column was successfully applied in SPME of PAEs in water sample with extraction recovery ranged of 78.8%-104.6% (<5.5% RSDs). Copyright © 2016 Elsevier B.V. All rights reserved.

Indoor pollutants emitted by office equipment: A review ofreported data and information needs

DOE Office of Scientific and Technical Information (OSTI.GOV)

Destaillats, Hugo; Maddalena, Randy L.; Singer, Brett C.

2007-02-01

There is concern that potentially harmful pollutants may be emitted from office equipment. Although office equipment has been a focal point for governmental efforts to promote energy efficiency through programs such as the US EPA's Energy Star, little is known about the relationship between office equipment use and indoor air quality, and information on pollutant emissions is sparse. In this review, we summarize available information on emission rates and/or ambient concentrations of various pollutants that are related to office equipment use. Experimental methods used in the characterization of emissions are briefly described. The office equipment evaluated in this review includesmore » computers (desktops and notebooks), printers (laser, ink-jet and all-in-one machines) and photocopy machines. Reported emission rates of the following pollutant groups are summarized: volatile organic chemicals (VOCs), ozone, particulate matter and several semivolatile organic chemicals (SVOCs). The latter include phthalate esters, brominated flame retardants, organophosphate flame retardants and polycyclic aromatic hydrocarbons (PAHs). We also review studies reporting airborne concentrations in indoor environments where office equipment was present and thought to be a significant contributor to the total pollutant burden (offices, residences, schools, electronics recycling plants). For certain pollutants, such as organophosphate flame retardants, the link between emission by office equipment and indoor air concentrations is relatively well established. However, indoor VOCs, ozone, PAHs and phthalate esters can originate from a variety of sources, and their source apportionment is less straightforward. This literature review identifies substances of toxicological significance, with the purpose of serving as a guide to evaluate their potential importance with respect to human exposures.« less

Development of dispersive liquid-liquid microextraction technique using ternary solvents mixture followed by heating for the rapid and sensitive analysis of phthalate esters and di(2-ethylhexyl) adipate.

PubMed

Farajzadeh, Mir Ali; Khoshmaram, Leila

2015-01-30

In this study, for the first time, a dispersive liquid-liquid microextraction technique using a ternary solvent mixture is reported. In order to extract five phthalate esters and di(2-ethylhexyl) adipate with different polarities from aqueous samples, a simplex centroid experimental design method was used to select an optimal mixture of ternary solvents prior to gas chromatographyflame ionization detection. In this work, dimethyl formamide as a disperser solvent containing dichloromethane, chloroform, and carbon tetrachloride as a ternary extraction solvent mixture is injected into sample solution and a cloudy solution is formed. After centrifuging, 250μL of the obtained sedimented phase was transferred into another tube and 5μL DMF was added to it. Then, the tube was heated in a water bath at 75°C for 5min in order to evaporate the main portion of the extraction solvents. Finally, 2μL of the remained phase is injected into the separation system. Under the optimum extraction conditions, the method shows wide linear ranges and low limits of detection and quantification between 0.03-0.15 and 0.09-0.55μgL(-1), respectively. Enrichment factors and extraction recoveries are in the ranges of 980-4500 and 20-90%, respectively. The method is successfully applied in the determination of the target analytes in mineral water, soda, lemon juice, vinegar, dough, and yogurt packed in plastic packages. Copyright © 2014 Elsevier B.V. All rights reserved.

Comparative study of the antioxidant activities of some lipase-catalyzed alkyl dihydrocaffeates synthesized in ionic liquid.

PubMed

Gholivand, Somayeh; Lasekan, Ola; Tan, Chin Ping; Abas, Faridah; Wei, Leong Sze

2017-06-01

The solubility limitations of phenolic acids in many lipidic environments are now greatly improved by their enzymatic esterification in ionic liquids (ILs). Herein, four different ILs were tested for the esterification of dihydrocaffeic acid with hexanol and the best IL was selected for the synthesis of four other n-alkyl esters with different chain-lengths. The effect of alkyl chain length on the anti-oxidative properties of the resulted purified esters was investigated using β-carotene bleaching (BCB) and free radical scavenging method DPPH and compared with butylated hydroxytoluene (BHT) as reference compound. All four esters (methyl, hexyl, dodecyl and octadecyl dihydrocaffeates) exhibited relatively strong radical scavenging abilities. The scavenging activity of the test compounds was in the following order: methyl ester>hexyl ester⩾dodecyl ester>octadecyl ester>BHT while the order for the BCB anti-oxidative activity was; BHT>octadecyl ester>dodecyl ester>hexyl ester>methyl ester. Copyright © 2016 Elsevier Ltd. All rights reserved.

Plasticizers and bisphenol A, in packaged foods sold in the Tunisian markets: study of their acute in vivo toxicity and their environmental fate.

PubMed

Beltifa, Asma; Feriani, Anouar; Machreki, Monia; Ghorbel, Asma; Ghazouani, Lakhdar; Di Bella, Giuseppa; Van Loco, Joris; Reyns, Tim; Mansour, Hedi Ben

2017-10-01

Today, processed and packaged foods are considered as among the major sources of human exposure to plasticizers and bisphenol which migrate from plastic packing. In the present study, a wide range of food products sold on the Tunisian market such as grain and grain products, milk and dairy products, fats and oil, drink, fish, and sweets have been analyzed firstly in order to identify the presence of phthalates and bisphenol. Then, the identified chemical molecules were studied for their environmental fate and tested in vivo for its toxicity in mice models. The food products analyzed using GC-MS/MS indicated the presence of the benzyl butyl phthalate (BBP), dibutyl phthalate (DBP), bis(2-ethylhexyl) phthalate (DEHP), diisodecyl phthalate (DiDP), diisononyl phthalate (DiNP), and 1,2-cyclohexane dicarboxylic acid diisononyl ester (DINC) and which using UPLC-MS/MS demonstrated the presence of bisphenol A of all food products. However, compared to other phthalates, BBP was found at high concentrations in the puff pastry (123 mg/kg), milk (2.59 mg/kg), butter (1.5 mg/kg), yogurt (2.23 mg/kg), oil (6.94 mg/kg), water (0.57 mg/kg), candy 1 (2.35 mg/kg), candy 2 (0.81 mg/kg), orange juice (1.25 mg/kg), peach juice (1.26 mg/kg), fruit juices (0.4 mg/kg), and chocolate (0.884 mg/kg). The obtained data in vivo clearly showed that the acute administration of BBP caused hepatic and renal damage as demonstrated by an increase in biochemical parameters as well as the activities of plasma marker enzymes such as alanine aminotransferase, aspartate aminotransferase, alkaline phosphatase, lactate dehydrogenase, blood urea nitrogen, glucose, urea, creatinine, and uric acid when compared to the control group. By the same occurrence, the histopathological study revealed that BBP strongly modified the structure of hepatic and renal tissues. In addition, the plasticizers and BBP will therefore discharge via wastewater treatment plants in aquatic system and could reach marine organisms such as fish. We have followed the fate of BBP in bream Sparus aurata. In fact, chemical analysis showed the contamination of wild S. aurata by BBP from Sousse Coast (1.5 mg/kg) and wild S. aurata from Monastir Coast (0.33 mg/kg).

Components of plastic: experimental studies in animals and relevance for human health

PubMed Central

Talsness, Chris E.; Andrade, Anderson J. M.; Kuriyama, Sergio N.; Taylor, Julia A.; vom Saal, Frederick S.

2009-01-01

Components used in plastics, such as phthalates, bisphenol A (BPA), polybrominated diphenyl ethers (PBDE) and tetrabromobisphenol A (TBBPA), are detected in humans. In addition to their utility in plastics, an inadvertent characteristic of these chemicals is the ability to alter the endocrine system. Phthalates function as anti-androgens while the main action attributed to BPA is oestrogen-like activity. PBDE and TBBPA have been shown to disrupt thyroid hormone homeostasis while PBDEs also exhibit anti-androgen action. Experimental investigations in animals indicate a wide variety of effects associated with exposure to these compounds, causing concern regarding potential risk to human health. For example, the spectrum of effects following perinatal exposure of male rats to phthalates has remarkable similarities to the testicular dysgenesis syndrome in humans. Concentrations of BPA in the foetal mouse within the range of unconjugated BPA levels observed in human foetal blood have produced effects in animal experiments. Finally, thyroid hormones are essential for normal neurological development and reproductive function. Human body burdens of these chemicals are detected with high prevalence, and concentrations in young children, a group particularly sensitive to exogenous insults, are typically higher, indicating the need to decrease exposure to these compounds. PMID:19528057

Occurrence, fate and effects of Di (2-ethylhexyl) Phthalate in wastewater treatment plants: a review.

PubMed

Zolfaghari, M; Drogui, P; Seyhi, B; Brar, S K; Buelna, G; Dubé, R

2014-11-01

Phthalates, such as Di (2-ethylhexyl) Phthalate (DEHP) are compounds extensively used as plasticizer for long time around the world. Due to the extensive usage, DEHP is found in many surface waters (0.013-18.5 μg/L), wastewaters (0.716-122 μg/L), landfill leachate (88-460 μg/L), sludge (12-1250 mg/kg), soil (2-10 mg/kg). DEHP is persistent in the environment and the toxicity of the byproducts resulting from the degradation of DEHP sometime exacerbates the parent compound toxicity. Water/Wastewater treatment processes might play a key role in delivering safe, reliable supplies of water to households, industry and in safeguarding the quality of water in rivers, lakes and aquifers. This review addresses state of knowledge concerning the worldwide production, occurrence, fate and effects of DEHP in the environment. Moreover, the fate and behavior of DEHP in various treatment processes, including biological, physicochemical and advanced processes are reviewed and comparison (qualitative and quantitative) has been done between the processes. The trends and perspectives for treatment of wastewaters contaminated by DEHP are also analyzed in this review. Copyright © 2014 Elsevier Ltd. All rights reserved.

Evaluation of nitrate-substituted pseudocholine esters of aspirin as potential nitro-aspirins.

PubMed

Gilmer, John F; Moriarty, Louise M; Clancy, John M

2007-06-01

Herein we explore some designs for nitro-aspirins, compounds potentially capable of releasing both aspirin and nitric oxide in vivo. A series of nitrate-bearing alkyl esters of aspirin were prepared based on the choline ester template preferred by human plasma butyrylcholinesterase. The degradation kinetics of the compounds were followed in human plasma solution. All compounds underwent hydrolysis rapidly (t(1/2) approximately 1min) but generating exclusively the corresponding nitro-salicylate. The one exception, an N-propyl, N-nitroxyethyl aminoethanol ester produced 9.2% aspirin in molar terms indicating that the nitro-aspirin objective is probably achievable if due cognisance can be paid to the demands of the activating enzyme. Even at this low level of aspirin release, this compound is the most successful nitro-aspirin reported to date in the key human plasma model.

18F-labeled Rhodamines as Potential Myocardial Perfusion Agents: Comparison of Pharmacokinetic Properties of Several Rhodamines

PubMed Central

Bartholoma, Mark D.; Zhang, Shaohui; Akurathi, Vamsidhar; Pacak, Christina A.; Dunning, Patricia; Fahey, Frederic H.; Cowan, Douglas B.; Treves, S. Ted; Packard, Alan B.

2015-01-01

Introduction We recently reported the development of the [18F]fluorodiethylene glycol ester of rhodamine B as a potential positron emission tomography (PET) tracer for myocardial perfusion imaging (MPI). This compound was developed by optimizing the ester moiety on the rhodamine B core, and its pharmacokinetic properties were found to be superior to those of the prototype ethyl ester. The goal of the present study was to optimize the rhodamine core while retaining the fluorodiethyleneglycol ester prosthetic group. Methods A series of different rhodamine cores (rhodamine 6G, rhodamine 101, and tetramethylrhodamine) were labeled with 18F using the corresponding rhodamine lactones as the precursors and [18F]fluorodiethylene glycol ester as the prosthetic group. The compounds were purified by semipreparative HPLC, and their biodistribution was measured in rats. Additionally, the uptake of the compounds was evaluated in isolated rat cardiomyocytes. Results As was the case with the different prosthetic groups, we found that the rhodamine core has a significant effect on the in vitro and in vivo properties of this series of compounds. Of the rhodamines evaluated to date, the pharmacologic properties of the 18F-labeled diethylene glycol ester of rhodamine 6G are superior to those of the 18F-labeled diethylene glycol esters of rhodamine B, rhodamine 101, and tetramethylrhodamine. As with 18F-labeled rhodamine B, [18F]rhodamine 6G was observed to localize in the mitochondria of isolated rat cardiomyocytes. Conclusions Based on these results, the 18F-labeled diethylene glycol ester of rhodamine 6G is the most promising potential PET MPI radiopharmaceutical of those that have been evaluated to date, and we are now preparing to carry out first-in-human clinical studies with this compound. PMID:26205075

(18)F-labeled rhodamines as potential myocardial perfusion agents: comparison of pharmacokinetic properties of several rhodamines.

PubMed

Bartholomä, Mark D; Zhang, Shaohui; Akurathi, Vamsidhar; Pacak, Christina A; Dunning, Patricia; Fahey, Frederic H; Cowan, Douglas B; Treves, S Ted; Packard, Alan B

2015-10-01

We recently reported the development of the [(18)F]fluorodiethylene glycol ester of rhodamine B as a potential positron emission tomography (PET) tracer for myocardial perfusion imaging (MPI). This compound was developed by optimizing the ester moiety on the rhodamine B core, and its pharmacokinetic properties were found to be superior to those of the prototype ethyl ester. The goal of the present study was to optimize the rhodamine core while retaining the fluorodiethyleneglycol ester prosthetic group. A series of different rhodamine cores (rhodamine 6G, rhodamine 101, and tetramethylrhodamine) were labeled with (18)F using the corresponding rhodamine lactones as the precursors and [(18)F]fluorodiethylene glycol ester as the prosthetic group. The compounds were purified by semipreparative HPLC, and their biodistribution was measured in rats. Additionally, the uptake of the compounds was evaluated in isolated rat cardiomyocytes. As was the case with the different prosthetic groups, we found that the rhodamine core has a significant effect on the in vitro and in vivo properties of this series of compounds. Of the rhodamines evaluated to date, the pharmacologic properties of the (18)F-labeled diethylene glycol ester of rhodamine 6G are superior to those of the (18)F-labeled diethylene glycol esters of rhodamine B, rhodamine 101, and tetramethylrhodamine. As with (18)F-labeled rhodamine B, [(18)F]rhodamine 6G was observed to localize in the mitochondria of isolated rat cardiomyocytes. Based on these results, the (18)F-labeled diethylene glycol ester of rhodamine 6G is the most promising potential PET MPI radiopharmaceutical of those that have evaluated to date, and we are now preparing to carry out first-in-human clinical studies with this compound. Copyright © 2015 Elsevier Inc. All rights reserved.

Pressurized liquid extraction-gas chromatography-mass spectrometry analysis of fragrance allergens, musks, phthalates and preservatives in baby wipes.

PubMed

Celeiro, Maria; Lamas, J Pablo; Garcia-Jares, Carmen; Llompart, Maria

2015-03-06

Baby wipes and wet toilet paper are specific hygiene care daily products used on newborn and children skin. These products may contain complexes mixtures of harmful chemicals. A method based on pressurized liquid extraction (PLE) followed by gas chromatography-mass spectrometry (GC-MS) has been developed for the simultaneous determination of sixty-five chemical compounds (fragrance allergens, preservatives, musks, and phthalates) in wipes and wet toilet paper for children. These compounds are legislated in Europe according Regulation EC No 1223/2009, being twelve of them banned for their use in cosmetics, and one of them, 3-iodo-2-propynyl butylcarbamate (IPBC), is banned in products intended for children under 3 years. Also, propyl-, and butylparaben will be prohibited in leave-on cosmetic products designed for application on the nappy area of children under 3 years from April 2015. PLE is a fast, simple, easily automated technique, which permits to integrate a clean-up step during the extraction process reducing analysis time and stages. The proposed PLE-based procedure was optimized on real non-spiked baby wipe samples by means of experimental design to study the influence on extraction of parameters such as extraction solvent, temperature, extraction time, and sorbent type. Under the selected conditions, the method was validated showing satisfactory linearity, and intra-day, and inter-day precision. Recoveries were between 80-115% for most of the compounds with relative standard deviations (RSD) lower than 15%. Finally, twenty real samples were analyzed. Thirty-six of the target analytes were detected, highlighting the presence of phenoxyethanol in all analyzed samples at high concentration levels (up to 0.8%, 800μgg(-1)). Methyl paraben (MeP), and ethyl paraben (EtP) were found in 40-50% of the samples, and the recently banned isobutyl paraben (iBuP) and isopropyl paraben (iPrP), were detected in one and seven samples, respectively, at concentrations between 0.093 and 247μgg(-1). In the case of phthalates, the forbidden phthalates dibutyl phtalate (DBP) and di(2-ethylhexyl)phthalate (DEHP) were also found in thirteen samples at low levels. All the samples contained fragrance allergens in many cases at high levels (up to 2400μgg(-1)) and three musks were detected in the samples. Excluding the banned compounds, all samples complied with the concentration limits established by the European Regulation although 25% of them did not fulfill the labeling requirements for fragrance allergens. Copyright © 2015 Elsevier B.V. All rights reserved.

Human biological monitoring of suspected endocrine-disrupting compounds

PubMed Central

Faniband, Moosa; Lindh, Christian H; Jönsson, Bo AG

2014-01-01

Endocrine-disrupting compounds are exogenous agents that interfere with the natural hormones of the body. Human biological monitoring is a powerful method for monitoring exposure to endocrine disrupting compounds. In this review, we describe human biological monitoring systems for different groups of endocrine disrupting compounds, polychlorinated biphenyls, brominated flame retardants, phthalates, alkylphenols, pesticides, metals, perfluronated compounds, parabens, ultraviolet filters, and organic solvents. The aspects discussed are origin to exposure, metabolism, matrices to analyse, analytical determination methods, determinants, and time trends. PMID:24369128

Emission of phthalates and phthalate alternatives from vinyl flooring and crib mattress covers: the influence of temperature.

PubMed

Liang, Yirui; Xu, Ying

2014-12-16

Emissions of phthalates and phthalate alternatives from vinyl flooring and crib mattress covers were measured in a specially designed chamber. The gas-phase concentrations versus time were measured at four different temperatures, that is, 25, 36, 45, and 55 °C. The key parameter that controls the emissions (y0, gas-phase concentration in equilibrium with the material phase) was determined, and the emissions were found to increase significantly with increasing temperature. Both the material-phase concentration (C0) and the chemical vapor pressure (Vp) were found to have great influence on the value of y0. The measured ratios of C0 to y0 were exponentially proportional to the reciprocal of temperature, in agreement with the van't Hoff equation. A emission model was validated at different temperatures, with excellent agreement between model calculations and chamber observations. In residential homes, an increase in the temperature from 25 to 35 °C can elevate the gas-phase concentration of phthalates by more than a factor of 10, but the total airborne concentration may not increase that much for less volatile compounds. In infant sleep microenvironments, an increase in the temperature of mattress can cause a significant increase in emission of phthalates from the mattress cover and make the concentration in the infant's breathing zone about four times higher than that in the bulk room air, resulting in potentially high exposure.

Serum Phthalate Levels and Time to Pregnancy in Couples from Greenland, Poland and Ukraine

PubMed Central

Specht, Ina Olmer; Bonde, Jens Peter; Toft, Gunnar; Lindh, Christian H.; Jönsson, Bo A. G.; Jørgensen, Kristian T.

2015-01-01

Phthalates are ubiquitous industrial chemicals that have been associated with altered reproductive function in rodents. Several human studies have reported an inverse association between male testosterone and phthalate levels. Our aim was to investigate time to pregnancy (TTP) according to serum levels of diethylhexyl phthalate (DEHP) and diisononyl phthalate (DiNP) metabolites in both partners. In 2002-2004 we enrolled 938 pregnant women and 401 male spouses from Greenland, Poland and Ukraine. Six oxidized metabolites of DEHP and DiNP were summarized for each of the two parent compounds to provide proxies of the internal exposure. We used Cox discrete-time models to estimate fecundability ratios (FR) and 95% confidence intervals (95% CIs) for men and women according to their proxy-DEHP or -DiNP serum levels adjusted for a fixed set of covariates. The FR was slightly elevated among women with high levels of DEHP (FR=1.14, 95% CI 1.00;1.30) suggesting a shorter TTP in these women. The FR was unrelated to DiNP in women, whereas the results for men were inconsistent pointing in opposite directions. First-time pregnant women from Greenland with high serum DiNP levels had a longer TTP. This study spanning large contrast in environmental exposure does not indicate adverse effects of phthalates on couple fecundity. The shorter TTP in women with high levels of DEHP metabolites is unexplained and needs further investigation. PMID:25786246

Designed biocompatible nano-inhibitor based on poly(β-cyclodextrin-ester) for reduction of the DEHP migration from plasticized PVC.

PubMed

Raeisi, Ahmad; Faghihi, Khalil; Shabanian, Meisam

2017-10-15

The easy migration of di(2-ethylhexyl) phthalate (DEHP) from the plasticized PVC (P-PVC) poses a serious threat to human health and the ecosystems. Thus, its control migration from the P-PVC products is very important. In this work, a poly(β-cyclodextrin-ester) network (β-CDP) was synthesized via reaction of β-cyclodextrin with 3,3',4,4'-benzophenone tetracarboxylic dianhydride. As a potential inhibitor for reduction of the DEHP migration, the β-CDP was grafted to Fe 3 O 4 nanoparticles. Poly(β-cyclodextrin-ester) functionalized Fe 3 O 4 nanoparticles (MNP-CDP) has been used in PVC/DEHP system as a reactive nano-inhibitor to reduce DEHP migration. Thermal stability and mechanical properties of obtained films were investigated. DEHP migration tests of the P-PVC films were also carried out by using Gas chromatography. It was found that by incorporating the small amounts of nano-inhibitor in PVC/DEHP system, the migration of DEHP effectively reduced from the P-PVC samples about 65% without any serious changes in mechanical and thermal properties of the P-PVC films. Copyright © 2017 Elsevier Ltd. All rights reserved.

Substituted Caffeic and Ferulic Acid Phenethyl Esters: Synthesis, Leukotrienes Biosynthesis Inhibition, and Cytotoxic Activity.

PubMed

Morin, Pier; St-Coeur, Patrick-Denis; Doiron, Jérémie A; Cormier, Marc; Poitras, Julie J; Surette, Marc E; Touaibia, Mohamed

2017-07-06

Glioblastoma multiforme (GBM) is an aggressive brain tumor that correlates with short patient survival and for which therapeutic options are limited. Polyphenolic compounds, including caffeic acid phenethyl ester (CAPE, 1a ), have been investigated for their anticancer properties in several types of cancer. To further explore these properties in brain cancer cells, a series of caffeic and ferulic acid esters bearing additional oxygens moieties (OH or OCH₃) were designed and synthesized. (CAPE, 1a ), but not ferulic acid phenethyl ester (FAPE, 1b ), displayed substantial cytotoxicity against two glioma cell lines. Some but not all selected compounds derived from both (CAPE, 1a ) and (FAPE, 1b ) also displayed cytotoxicity. All CAPE-derived compounds were able to significantly inhibit 5-lipoxygenase (5-LO), however FAPE-derived compounds were largely ineffective 5-LO inhibitors. Molecular docking revealed new hydrogen bonds and π-π interactions between the enzyme and some of the investigated compounds. Overall, this work highlights the relevance of exploring polyphenolic compounds in cancer models and provides additional leads in the development of novel therapeutic strategies in gliomas.

Emerging pollutants in wastewater: a review of the literature.

PubMed

Deblonde, Tiphanie; Cossu-Leguille, Carole; Hartemann, Philippe

2011-11-01

For 20 years, many articles report the presence of new compounds, called "emerging compounds", in wastewater and aquatic environments. The US EPA (United States - Environmental Protection Agency) defines emerging pollutants as new chemicals without regulatory status and which impact on environment and human health are poorly understood. The objective of this work was to identify data on emerging pollutants concentrations in wastewater, in influent and effluent from wastewater treatment plants (WWTPs) and to determine the performance of sewage disposal. We collected 44 publications in our database. We sought especially for data on phthalates, Bisphenol A and pharmaceuticals (including drugs for human health and disinfectants). We gathered concentration data and chose 50 pharmaceutical molecules, six phthalates and Bisphenol A. The concentrations measured in the influent ranged from 0.007 to 56.63 μg per liter and the removal rates ranges from 0% (contrast media) to 97% (psychostimulant). Caffeine is the molecule whose concentration in influent was highest among the molecules investigated (in means 56.63 μg per liter) with a removal rate around 97%, leading to a concentration in the effluent that did not exceed 1.77 μg per liter. The concentrations of ofloxacin were the lowest and varied between 0.007 and 2.275 μg per liter in the influent treatment plant and 0.007 and 0.816 μg per liter in the effluent. Among phthalates, DEHP is the most widely used, and quantified by the authors in wastewater, and the rate of removal of phthalates is greater than 90% for most of the studied compounds. The removal rate for antibiotics is about 50% and 71% for Bisphenol A. Analgesics, anti inflammatories and beta-blockers are the most resistant to treatment (30-40% of removal rate). Some pharmaceutical molecules for which we have not collected many data and which concentrations seem high as Tetracycline, Codeine and contrast products deserve further research. Copyright © 2011 Elsevier GmbH. All rights reserved.

Partitioning of polycyclic aromatic hydrocarbons, alkylphenols, bisphenol A and phthalates in landfill leachates and stormwater.

PubMed

Kalmykova, Yuliya; Björklund, Karin; Strömvall, Ann-Margret; Blom, Lena

2013-03-01

Partitioning of organic pollutants is essential to their fate, mobility and removal from water and soil. To study the partitioning behavior of selected alkylphenols, bisphenol A, phthalates and polycyclic aromatic hydrocarbons (PAHs), a method for separating the truly dissolved and colloidal phase of organic pollutants was developed, verified and applied to samples of landfill leachate and stormwater from urban areas and waste-sorting sites. Alkylphenols, bisphenol A, phthalates and PAHs were detected in all the untreated samples (total concentrations), most of the filtered samples and frequently in the colloid-bound phase. Concentrations of alkylphenols and PAHs in urban stormwater were one order of magnitude lower than in the landfill leachates and stormwater from waste-sorting sites. The difference between total, dissolved and colloid-bound concentrations in the water samples was not statistically significant for any phenols or phthalates, but for three of the PAHs; naphthalene (mostly dissolved), phenanthrene and fluoranthene (mostly particulate). These results indicate that in landfill leachates and stormwaters, organic pollutants are predominantly attached to colloids and/or truly dissolved in contrast to their expected strong sorption to particulate matter. Occurrence and concentrations of pollutants in dissolved and colloid-bound phases correlated negatively with the K(OW). However, even highly hydrophobic compounds were frequently detected in filtered samples, i.e. the dissolved phases, and it is suggested that the organic content in the colloids decreases the compounds' partition to particles. The results confirm that the K(OW) values of specific organic pollutants well describe the compounds partition-binding process to dissolved organic carbon (DOC) colloids. Our findings call for a re-assessment of the organic pollutants' mobility and associated risks. This knowledge can also serve as a base for selecting efficient treatment methods for stormwater and landfill leachates. Copyright © 2012 Elsevier Ltd. All rights reserved.

Selected trace-element and synthetic-organic compound data for streambed sediment from the Clark Fork-Pend Oreille and Spokane River basins, Montana, Idaho, and Washington, 1998

USGS Publications Warehouse

Beckwith, Michael A.

2002-01-01

Most of the analytical results for synthetic organic compounds were reported as either estimated or non-detected values. Phthalates and polycyclic aro­matic hydrocarbons were the most frequently detected classes of synthetic organic compounds in streambed sediment. Organochlorine pesticide residues were detected at two sites. Polychlorinated biphenyls were detected at one site.

Antiandrogenic activity of phthalate mixtures: Validity of concentration addition

DOE Office of Scientific and Technical Information (OSTI.GOV)

Christen, Verena; Crettaz, Pierre; Oberli-Schrämmli, Aurelia

2012-03-01

Phthalates and bisphenol A have very widespread use leading to significant exposure of humans. They are suspected to interfere with the endocrine system, including the androgen, estrogen and the thyroid hormone system. Here we analyzed the antiandrogenic activity of six binary, and one ternary mixture of phthalates exhibiting complete antiandrogenic dose–response curves, and binary mixtures of phthalates and bisphenol A at equi-effective concentrations of EC{sub 10}, EC{sub 25} and EC{sub 50} in MDA-kb2 cells. Mixture activity followed the concentration addition (CA) model with a tendency to synergism at high and antagonism at low concentrations. Isoboles and the toxic unit approachmore » (TUA) confirmed the additive to synergistic activity of the binary mixtures BBP + DBP, DBP + DEP and DEP + BPA at high concentrations. Both methods indicate a tendency to antagonism for the EC{sub 10} mixtures BBP + DBP, BBP + DEP and DBP + DEP, and the EC{sub 25} mixture of DBP + BPA. A ternary mixture revealed synergism at the EC{sub 50}, and weak antagonistic activity at the EC{sub 25} level by the TUA. A mixture of five phthalates representing a human urine composition and reflecting exposure to corresponding parent compounds showed no antiandrogenic activity. Our study demonstrates that CA is an appropriate concept to account for mixture effects of antiandrogenic phthalates and bisphenol A. The interaction indicates a departure from additivity to antagonism at low concentrations, probably due to interaction with the androgen receptor and/or cofactors. This study emphasizes that a risk assessment of phthalates should account for mixture effects by applying the CA concept. -- Highlights: ► Antiandrogenic activity of mixtures of 2 and 3 phthalates are assessed in MDA-kb2 cells. ► Mixture activities followed the concentration addition model. ► A tendency to synergism at high and antagonism at low levels occurred.« less

Rapid, automated online SPE-LC-QTRAP-MS/MS method for the simultaneous analysis of 14 phthalate metabolites and 5 bisphenol analogues in human urine.

PubMed

Heffernan, A L; Thompson, K; Eaglesham, G; Vijayasarathy, S; Mueller, J F; Sly, P D; Gomez, M J

2016-05-01

Phthalates and bisphenol A (BPA) have received special attention in recent years due to their frequent use in consumer products and potential for adverse effects on human health. BPA is being replaced with a number of alternatives, including bisphenol S, bisphenol B, bisphenol F and bisphenol AF. These bisphenol analogues have similar potential for adverse health effects, but studies on human exposure are limited. Accurate measurement of multiple contaminants is important for estimating exposure. This paper describes a sensitive and automated method for the simultaneous determination of 14 phthalate metabolites, BPA and four bisphenol analogues in urine using online solid phase extraction coupled with high-performance liquid chromatography/tandem mass spectrometry using a hybrid triple-quadrupole linear ion trap mass spectrometer (LC-QTRAP-MS/MS), requiring very little sample volume (50µL). Quantification was performed under selected reaction monitoring (SRM) mode with negative electrospray ionization. The use of SRM combined with an enhanced product ion scan within the same analysis was examined. Unequivocal identification was provided by the acquisition of three SRM transitions per compound and isotope dilution. The analytical performance of the method was evaluated in synthetic and human urine. Linearity of response over three orders of magnitude was demonstrated for all of the compounds (R(2)>0.99), with method detection limits of 0.01-0.5ng/mL and limits of reporting of 0.07-3.1ng/mL. Accuracy ranged from 93% to 113% and inter- and intra-day precision were <22%. Finally, the validated method has been successfully applied to a cohort of pregnant women to measure biomarker concentrations of phthalates and bisphenols, with median concentrations ranging from 0.3ng/mL (bisphenol S) to 18.5ng/mL (monoethyl phthalate). Copyright © 2016 Elsevier B.V. All rights reserved.

Occurrence and risk assessment of potentially toxic elements and typical organic pollutants in contaminated rural soils.

PubMed

Xu, Yongfeng; Dai, Shixiang; Meng, Ke; Wang, Yuting; Ren, Wenjie; Zhao, Ling; Christie, Peter; Teng, Ying

2018-07-15

The residual levels and risk assessment of several potentially toxic elements (PTEs), phthalate esters (PAEs) and polycyclic aromatic hydrocarbons (PAHs) in rural soils near different types of pollution sources in Tianjin, China, were studied. The soils were found to be polluted to different extents with PTEs, PAEs and PAHs from different pollution sources. The soil concentrations of chromium (Cr), nickel (Ni), di-n-butyl phthalate (DnBP), acenaphthylene (Any) and acenaphthene (Ane) were higher than their corresponding regulatory reference limits. The health risk assessment model used to calculate human exposure indicates that both non-carcinogenic and carcinogenic risks from selected pollutants were generally acceptable or close to acceptable. Different types of pollution sources and soil physicochemical properties substantially affected the soil residual concentrations of and risks from these pollutants. PTEs in soils collected from agricultural lands around industrial and residential areas and organic pollutants (PAEs and PAHs) in soils collected from agricultural areas around livestock breeding were higher than those from other types of pollution sources and merit long-term monitoring. Copyright © 2018 Elsevier B.V. All rights reserved.

Analysis of plasticiser migration to meat roasted in plastic bags by SPME-GC/MS.

PubMed

Moreira, Miriany Avelino; André, Leiliane Coelho; Cardeal, Zenilda de Lourdes

2015-07-01

Plasticisers are compounds used in the polymer industry to increase the flexibility of plastics. Some of these compounds cause endocrine dysfunction in humans and animals by interfering with the production, release, transport, metabolism, binding or elimination of natural hormones in the body and are therefore recognised as endocrine disruptors. This paper describes cold-fibre solid-phase microextraction as a sampling technique to analyse eight plasticisers in spices and roasted chicken meat stored in plastic bags by gas chromatography-mass spectrometry. Limits of detection for this method ranged from 0.01 to 0.18 μg kg(-)(1). Diisobutyl phthalate and dibutyl phthalate were found in the samples of spices and roasted chicken meat. The highest concentrations of plasticisers were found in the spices used to cook the chicken meat. Copyright © 2015 Elsevier Ltd. All rights reserved.

Environmentally Friendly Procedure Based on Supercritical Fluid Chromatography and Tandem Mass Spectrometry Molecular Networking for the Discovery of Potent Antiviral Compounds from Euphorbia semiperfoliata.

PubMed

Nothias, Louis-Félix; Boutet-Mercey, Stéphanie; Cachet, Xavier; De La Torre, Erick; Laboureur, Laurent; Gallard, Jean-François; Retailleau, Pascal; Brunelle, Alain; Dorrestein, Pieter C; Costa, Jean; Bedoya, Luis M; Roussi, Fanny; Leyssen, Pieter; Alcami, José; Paolini, Julien; Litaudon, Marc; Touboul, David

2017-10-27

A supercritical fluid chromatography-based targeted purification procedure using tandem mass spectrometry and molecular networking was developed to analyze, annotate, and isolate secondary metabolites from complex plant extract mixture. This approach was applied for the targeted isolation of new antiviral diterpene esters from Euphorbia semiperfoliata whole plant extract. The analysis of bioactive fractions revealed that unknown diterpene esters, including jatrophane esters and phorbol esters, were present in the samples. The purification procedure using semipreparative supercritical fluid chromatography led to the isolation and identification of two new jatrophane esters (13 and 14) and one known (15) and three new 4-deoxyphorbol esters (16-18). The structure and absolute configuration of compound 16 were confirmed by X-ray crystallography. This compound was found to display antiviral activity against Chikungunya virus (EC 50 = 0.45 μM), while compound 15 proved to be a potent and selective inhibitor of HIV-1 replication in a recombinant virus assay (EC 50 = 13 nM). This study showed that a supercritical fluid chromatography-based protocol and molecular networking can facilitate and accelerate the discovery of bioactive small molecules by targeting molecules of interest, while minimizing the use of toxic solvents.

Carbodithioic acid esters of fluoxetine, a novel class of dual-function spermicides.

PubMed

Kiran Kumar, S T V S; Kumar, Lalit; Sharma, Vishnu L; Jain, Ashish; Jain, Rajeev K; Maikhuri, Jagdamba P; Kumar, Manish; Shukla, Praveen K; Gupta, Gopal

2008-10-01

Carbodithioic acid esters of fluoxetine have been prepared by replacing the methylamino function in aminopropane chain with carbodithioic acid ester group and by adding various S-2-hydroxypropyl ester of dialkyl carbodithioic acid at 3-methylamino group. Some of these compounds showed spermicidal, antifungal and anti-Trichomonas activities. The study revealed that incorporation of carbodithioic acid residue directly into fluoxetine structure leads to compounds with better antifungal and anti-Trichomonas activities, and N-methyl-[3-phenyl-3-(4-trifluoromethyl-phenoxy)-propyl]carbodithioic acid S-(2-pyrrolidino-ethyl) ester (14) has shown better profile than both fluoxetine and nonoxynol-9. Further lead optimization may yield a potent dual-function spermicide.

Enantioselective Synthesis of α-Mercapto-β-amino Esters via Rh(II)/Chiral Phosphoric Acid-Cocatalyzed Three-Component Reaction of Diazo Compounds, Thiols, and Imines.

PubMed

Xiao, Guolan; Ma, Chaoqun; Xing, Dong; Hu, Wenhao

2016-12-02

An enantioselective method for the synthesis of α-mercapto-β-amino esters has been developed via a rhodium(II)/chiral phosphoric acid-cocatalyzed three-component reaction of diazo compounds, thiols, and imines. This transformation is proposed to proceed through enantioselective trapping of the sulfonium ylide intermediate generated in situ from the diazo compound and thiol by the phosphoric acid-activated imine. With this method, a series of α-mercapto-β-amino esters were obtained in good yields with moderate to good stereoselectivities.

Enzymatic synthesis of 1,3-dihydroxyphenylacetoyl-sn-glycerol: Optimization by response surface methodology and evaluation of its antioxidant and antibacterial activities.

PubMed

Kharrat, Nadia; Aissa, Imen; Dgachi, Youssef; Aloui, Fatma; Chabchoub, Fakher; Bouaziz, Mohamed; Gargouri, Youssef

2017-12-01

In this study, the enzymatic synthesis of phenylacetoyl glycerol ester was carried out as a response to the increasing consumer demand for natural compounds. 1,3-dihydroxyphenylacetoyl-sn-Glycerol (1,3-di-HPA-Gly), labeled as "natural" compound with interesting biological properties, has been successfully synthesized for the first time in good yield by a direct esterification of glycerol (Gly) with p-hydroxyphenylacetic acid (p-HPA) using immobilized Candida antarctica lipase as a biocatalyst. Spectroscopic analyses of purified esters showed that the glycerol was mono- or di-esterified on the primary hydroxyl group. These compounds were evaluated for their antioxidant activity using two different tests. The glycerol di-esters (1,3-di-HPA-Gly) showed a higher antiradical capacity than that of the butyl hydroxytoluene. Furthermore, compared to the p-HPA, synthesized ester (1,3-di-HPA-Gly) exhibited the most antibacterial effect mainly against Gram + bacteria. Among synthesized esters the 1,3-di-HPA-Gly was most effective as antioxidant and antibacterial compound. These findings could be the basis for a further exploitation of the new compound, 1,3-di-HPA-Gly, as antioxidant and antibacterial active ingredient in the cosmetic and pharmaceutical fields. Copyright © 2017. Published by Elsevier Inc.

Spectroscopic detection of pharmaceutical compounds from an aflatoxigenic strain of Aspergillus parasiticus.

PubMed

Basaran, P; Demirbas, R M

2010-08-20

Polar and non-polar secondary metabolites as well as phenolic compounds of Aspergillus parasiticus grown on hazelnut were analyzed by high-resolution high performance liquid chromatography-mass spectroscopy and fourier transform infrared spectroscopy. Several novel and beneficial compounds such as dibutyl phthalate, pyrogallol, fumagillol, italicic acid and sorbicillin were identified from A. parasiticus for the first time. Some of these compounds have the potential to be used in pharmaceutical industry. Copyright 2009 Elsevier GmbH. All rights reserved.

Preparative purification of the major anti-inflammatory triterpenoid esters from Marigold (Calendula officinalis).

PubMed

Hamburger, M; Adler, S; Baumann, D; Förg, A; Weinreich, B

2003-06-01

A method for the efficient preparative purification of faradiol 3-O-laurate, palmitate and myristate, the major anti-inflammatory triterpenoid esters in the flower heads of the medicinal plant Calendula officinalis has been developed. Gram quantities of the individual compounds were obtained with 96 to 98% purity by a combination of supercritical fluid extraction (SFE), normal-phase and reversed-phase column chromatography. During the work-up of the faradiol esters, accompanying minor compounds of the triterpene ester fraction were purified and identified by spectroscopic means as maniladiol 3-O-laurate and myristate.

A critical analysis of the biological impacts of plasticizers on wildlife

PubMed Central

Oehlmann, Jörg; Schulte-Oehlmann, Ulrike; Kloas, Werner; Jagnytsch, Oana; Lutz, Ilka; Kusk, Kresten O.; Wollenberger, Leah; Santos, Eduarda M.; Paull, Gregory C.; Van Look, Katrien J. W.; Tyler, Charles R.

2009-01-01

This review provides a critical analysis of the biological effects of the most widely used plasticizers, including dibutyl phthalate, diethylhexyl phthalate, dimethyl phthalate, butyl benzyl phthalate and bisphenol A (BPA), on wildlife, with a focus on annelids (both aquatic and terrestrial), molluscs, crustaceans, insects, fish and amphibians. Moreover, the paper provides novel data on the biological effects of some of these plasticizers in invertebrates, fish and amphibians. Phthalates and BPA have been shown to affect reproduction in all studied animal groups, to impair development in crustaceans and amphibians and to induce genetic aberrations. Molluscs, crustaceans and amphibians appear to be especially sensitive to these compounds, and biological effects are observed at environmentally relevant exposures in the low ng l−1 to µg l−1 range. In contrast, most effects in fish (except for disturbance in spermatogenesis) occur at higher concentrations. Most plasticizers appear to act by interfering with the functioning of various hormone systems, but some phthalates have wider pathways of disruption. Effect concentrations of plasticizers in laboratory experiments coincide with measured environmental concentrations, and thus there is a very real potential for effects of these chemicals on some wildlife populations. The most striking gaps in our current knowledge on the impacts of plasticizers on wildlife are the lack of data for long-term exposures to environmentally relevant concentrations and their ecotoxicity when part of complex mixtures. Furthermore, the hazard of plasticizers has been investigated in annelids, molluscs and arthropods only, and given the sensitivity of some invertebrates, effects assessments are warranted in other invertebrate phyla. PMID:19528055

Using exposure prediction tools to link exposure and ...

EPA Pesticide Factsheets

A few different exposure prediction tools were evaluated for use in the new in vitro-based safety assessment paradigm using di-2-ethylhexyl phthalate (DEHP) and dibutyl phthalate (DnBP) as case compounds. Daily intake of each phthalate was estimated using both high-throughput (HT) prediction models such as the HT Stochastic Human Exposure and Dose Simulation model (SHEDS-HT) and the ExpoCast heuristic model and non-HT approaches based on chemical specific exposure estimations in the environment in conjunction with human exposure factors. Reverse dosimetry was performed using a published physiologically based pharmacokinetic (PBPK) model for phthalates and their metabolites to provide a comparison point. Daily intakes of DEHP and DnBP were estimated based on the urinary concentrations of their respective monoesters, mono-2-ethylhexyl phthalate (MEHP) and monobutyl phthalate (MnBP), reported in NHANES (2011–2012). The PBPK-reverse dosimetry estimated daily intakes at the 50th and 95th percentiles were 0.68 and 9.58 μg/kg/d and 0.089 and 0.68 μg/kg/d for DEHP and DnBP, respectively. For DEHP, the estimated median from PBPK-reverse dosimetry was about 3.6-fold higher than the ExpoCast estimate (0.68 and 0.18 μg/kg/d, respectively). For DnBP, the estimated median was similar to that predicted by ExpoCast (0.089 and 0.094 μg/kg/d, respectively). The SHEDS-HT prediction of DnBP intake from consumer product pathways alone was higher at 0.67 μg/kg/d. The PBPK-reve

Sampling, Testing, and Test Interpretation of Dredged Material Proposed for Unconfined, Open-Water Disposal in Central Puget Sound. Volume 5. Evaluation Procedures Technical Appendix. Phase 1

DTIC Science & Technology

1988-06-01

petroleum and combustion products. Consequently, the PSDDA list of chemicals of concern includes 16 polynuclear aromatic hydrocarbons (PAHs). Measurement...This material usually includes slurry water. Hydrocarbon . An organic compound composed of carbon and hydrogen. Petroleum and its derived compounds... Hydrocarbons Phthalates Pesticides Miscellaneous Compounds Biological Testing --Amphipod Bioassay Microtox Bioassay Macoma Bioaccumulation Costs for

Screening lactic acid bacteria strains with ability to bind di-n-butyl phthalate via Turbiscan technique.

PubMed

Lili, Zhao; Hongfei, Zhao; Shoukat, Sana; Xiaochen, Zhang; Bolin, Zhang

2017-06-01

Di-n-butyl phthalate (DBP) is a ubiquitous environmental contaminant that poses a risk to humans. Previous work indicates that the ability of lactic acid bacteria (LAB) to bind phthalic acid esters is strain-specific. As cell suspensions of LAB strains in aqueous solution are likely to be colloidal dispersions, this study provided a technique to efficiently screen LAB strains that bind DBP via Turbiscan, which has been widely used to measure the stability of emulsions or colloidal dispersions. Eleven LAB strains belonging to Lactobacillus plantarum, Lb. pentosus, Lb. paralimentarius, Lb. helveticus, Leuconostoc mesenteroides, Lb. acidophilus, Bifidobacterium lactis, and Bifidobacterium bifidum species were used in this study, and seven of them were selected to test in an earlier stage of exploring the process for finding a screening method; others were used for a validation test. It was observed that the various values of the 10 h Turbiscan Stability Index (TSI) of the cell suspension from each strain, at the equilibrium time of dispersed particles according to the peak thickness of cell-suspensions as measured by Turbiscan, had significant negative correlations with the DBP-binding percentage of LAB strains. Higher TSI values are correlated with lower binding of bacteria strains to DBP with a correlation coefficient of 0.8292. Cell surface hydrocarbons of LAB strains and their adherence were observed to correlate with DBP-binding percentages and may lead to the different states of aggregation or equilibrium of bacterial cell-suspensions, and the aggregation of bacterial cells resulted in fewer binding sites in the cell wall for DBP. Finally, four LAB strains were randomly selected to verify the feasibility of the method. In all, the findings demonstrate that TSI might be used as a tool to quickly screen strains that bind DBP. The present work could be extended to the removal of other toxic compounds, when screening of high-efficiency strains is required.

Nutrients, heavy metals and phthalate acid esters in solar greenhouse soils in Round-Bohai Bay-Region, China: impacts of cultivation year and biogeography.

PubMed

Chen, Zhiqun; Tian, Tian; Gao, Lihong; Tian, Yongqiang

2016-07-01

Solar greenhouse is a common facility type used for horticultural crop production in China. However, most solar greenhouse fields have been degraded due to continuous cropping and excessive fertilizer use. Therefore, we investigated solar greenhouse soils covering a wide range of cultivation years and environmental conditions in Round-Bohai Bay-Region to test the effects of cultivation year and biogeography on nutrients, heavy metals, and phthalate acid esters (PAEs). In general, soil pH decreased while soil electrical conductivity (EC), organic matter (OM), total nitrogen (TN), NO3 (-)-N, NH4 (+)-N, mineral nitrogen (MN), Olsen-P, and NH4OAc-K contents increased as time of cultivation increased. However, this trend was influenced by sampling sites. Among sampling sites, Jiangsu showed a relatively low soil pH and high Olsen-P content, while Hebei showed a relatively high soil EC value, NO3 (-)-N, NH4 (+)-N, MN, and NH4OAc-K contents. Liaoning was characterized by relatively high soil OM and TN contents. The nutrient level indexes in evaluation of soil quality on Olsen-P and NH4OAc-K exceeded the standard seriously. The maximum values of the heavy metals Cd, Cu, and Zn were 4.87, 2.78, and 1.15 times higher than the threshold values, respectively. There was a rising trend on the heavy metal contents with the increasing cultivation years, and this trend was significantly influenced by sampling sites. Both Cu and Zn had relative high heavy metal indexes in evaluation of soil pollution. The PAEs were not detected in almost all sampling soils. Overall, the excessive fertilizer application was an important cause of nutrient accumulation and heavy metal pollution, resulting in soil degradation in solar greenhouses.

Adsorption and desorption of phthalic acid esters on graphene oxide and reduced graphene oxide as affected by humic acid.

PubMed

Lu, Lun; Wang, Jun; Chen, Baoliang

2018-01-01

The implications of humic acid (HA) regarding surface properties of graphene materials and their interactions with phthalic acid esters (PAEs) are not vivid. We report the role of HA on graphene oxide (GO) and reduced graphene oxide (RGO) for sorption-desorption behavior of PAEs. Besides higher surface area and pore volume, the hydrophobic π-conjugated carbon atoms on RGO ensured prominent adsorption capacity towards PAEs in comparison to hydrophilic GO, highlighting the hydrophobic effect. After adjusting for the hydrophobic effect by calculating the hexadecane-water partition coefficient (K HW ) normalized adsorption coefficient (K d /K HW ), the dimethyl phthalate (DMP) molecule portrayed a higher adsorption affinity towards RGO by π-π electron donor-acceptor (EDA) interaction for active sites on graphene interface via sieving effect. In contrast to RGO, the weak π-π EDA interactions and H-bonding was observed between the carbonyl groups of PAEs and oxygen containing functional groups on GO. There was no obvious change in morphologies of GO and RGO before and desorption as revealed by SEM and TEM images, as desorption hysteresis did not occur in all conditions. The presence of HA also resulted in shielding effect thereby decreasing the adsorption rate and capacity of diethyl phthalate (DEP) on GO and RGO, while it had little effect on DMP, probably due to the adsorbed HA as new active sites. The desorption of DMP and DEP on RGO in presence of HA was quick and enhanced. These results should be important for evaluating the fate and health risk of graphene materials and PAEs in the environment. Copyright © 2017 Elsevier Ltd. All rights reserved.

Determination of phthalate esters in drinking water and edible vegetable oil samples by headspace solid phase microextraction using graphene/polyvinylchloride nanocomposite coated fiber coupled to gas chromatography-flame ionization detector.

PubMed

Amanzadeh, Hatam; Yamini, Yadollah; Moradi, Morteza; Asl, Yousef Abdossalmi

2016-09-23

In the current study, a graphene/polyvinylchloride nanocomposite was successfully coated on a stainless steel substrate by a simple dip coating process and used as a novel headspace solid phase microextraction (HS-SPME) fiber for the extraction of phthalate esters (PEs) from drinking water and edible vegetable oil samples. The prepared SPME fibers exhibited high extractability for PEs (due to the dominant role of π-π stacking interactions and hydrophobic effects) yielding good sensitivity and precision when followed by a gas chromatograph with a flame ionization detector (GC-FID). The optimization strategy of the extraction process was carried out using the response surface method based on a central composite design. The developed method gave a low limit of detection (0.06-0.08μgL(-1)) and good linearity (0.2-100μgL(-1)) for the determination of the PEs under the optimized conditions (extraction temperature, 70±1°C; extraction time, 35min; salt concentration, 30% w/v; stirring rate, 900rpm; desorption temperature, 230°C; and desorption time, 4min) whereas the repeatability and fiber-to-fiber reproducibility were in the range 6.1-7.8% and 8.9-10.2%, respectively. Finally, the proposed method was successfully applied to the analysis of PEs in drinking water and edible oil samples with good recoveries (87-112%) and satisfactory precisions (RSDs<8.3%), indicating the absence of matrix effects in the proposed HS-SPME method. Copyright © 2016 Elsevier B.V. All rights reserved.

Investigating into composition, distribution, sources and health risk of phthalic acid esters in street dust of Xi'an City, Northwest China.

PubMed

Wang, Lijun; Zhang, Wenjuan; Tao, Wendong; Wang, Li; Shi, Xingmin; Lu, Xinwei

2017-08-01

Phthalic acid esters (PAEs) are widely used as plasticizers and in consumer products, which may enter the environment and present risks to human health. U.S. EPA classifies six PAEs as priority pollutants, which could be accumulated in street dust at the interface of atmosphere, biosphere and geosphere. This study collected a total of 58 street dust samples from Xi'an City in Northwest China and analyzed for concentrations of the priority PAEs. Composition, distribution, sources and health risk of the PAEs were further examined. All the priority PAEs were detected in the street dust. The concentrations of individual PAEs varied between not detected and 183.19 mg/kg. The sum of the 6 priority PAEs (∑6PAEs) ranged from 0.87 to 250.30 mg/kg with a mean of 40.48 mg/kg. The most abundant PAEs in the street dust were di-n-butyl phthalate and di (2-ethylhexyl) phthalate (DEHP). Higher concentrations of ∑6PAEs in the street dust were found in the south and west parts of Xi'an City as well as its urban center, which were possibly attributed to the prevailing northerly Asian winter monsoon. The PAEs in the street dust originated mainly from wide application of plasticizers as well as cosmetics and personal care products. The main pathways of human exposure to PAEs in the street dust were ingestion and dermal adsorption of dust particles. The non-cancer risk of human exposure to PAEs in the street dust was relatively low, while the risk to children was higher than that to adults. The cancer risk of human exposure to DEHP in the street dust was lower than the standard limit value of 10 -6 .

Distribution and sources of polycyclic aromatic hydrocarbons and phthalic acid esters in water and surface sediment from the Three Gorges Reservoir.

PubMed

Lin, Li; Dong, Lei; Meng, Xiaoyang; Li, Qingyun; Huang, Zhuo; Li, Chao; Li, Rui; Yang, Wenjun; Crittenden, John

2018-07-01

After the impoundment of the Three Gorges Reservoir (TGR), the hydrological situation of the reservoir has changed greatly. The concentration and distribution of typical persistent organic pollutants in water and sediment have also changed accordingly. In this study, the concentration, distribution and potential sources of 16 polycyclic aromatic hydrocarbons (PAHs) and 6 phthalic acid esters (PAEs) during the water drawdown and impoundment periods were investigated in water and sediment from the TGR. According to our results, PAHs and PAEs showed temporal and spatial variations. The mean ΣPAH and ΣPAE concentrations in water and sediment were both higher during the water impoundment period than during the water drawdown period. The water samples from the main stream showed larger ΣPAH concentration fluctuations than those from tributaries. Both the PAH and PAE concentrations meet the Chinese national water environmental quality standard (GB 3838-2002). PAH monomers with 2-3 rings and 4 rings were dominant in water, and 4-ring and 5-6-ring PAHs were dominant in sediment. Di-n-butyl phthalate (DBP) and di-2-ethylhexyl phthalate (DEHP) were the dominant PAE pollutants in the TGR. DBP and DEHP had the highest concentrations in water and sediment, respectively. The main source of PAHs in water from the TGR was petroleum and emissions from coal and biomass combustion, whereas the main sources of PAHs in sediments included coal and biomass combustion, petroleum, and petroleum combustion. The main source of PAEs in water was domestic waste, and the plastics and heavy chemical industries were the main sources of PAEs in sediment. Copyright © 2017. Published by Elsevier B.V.

Halogenated flame retardants in the Great Lakes environment.

PubMed

Venier, Marta; Salamova, Amina; Hites, Ronald A

2015-07-21

Flame retardants are widely used industrial chemicals that are added to polymers, such as polyurethane foam, to prevent them from rapidly burning if exposed to a small flame or a smoldering cigarette. Flame retardants, especially brominated flame retardants, are added to many polymeric products at percent levels and are present in most upholstered furniture and mattresses. Most of these chemicals are so-called "additive" flame retardants and are not chemically bound to the polymer; thus, they migrate from the polymeric materials into the environment and into people. As a result, some of these chemicals have become widespread pollutants, which is a concern given their possible adverse health effects. Perhaps because of their environmental ubiquity, the most heavily used group of brominated flame retardants, the polybrominated diphenyl ethers (PBDEs), was withdrawn from production and use during the 2004-2013 period. This led to an increasing demand for other flame retardants, including other brominated aromatics and organophosphate esters. Although little is known about the use or production volumes of these newer flame retardants, it is evident that some of these chemicals are also becoming pervasive in the environment and in humans. In this Account, we describe our research on the occurrence of halogenated and organophosphate flame retardants in the environment, with a specific focus on the Great Lakes region. This Account starts with a short introduction to the first generation of brominated flame retardants, the polybrominated biphenyls, and then presents our measurements of their replacement, the PBDEs. We summarize our data on PBDE levels in babies, bald eagles, and in air. Once these compounds came off the market, we began to measure several of the newer flame retardants in air collected on the shores of the Great Lakes once every 12 days. These new measurements focus on a tetrabrominated benzoate, a tetrabrominated phthalate, a hexabrominated diphenoxyethane, several brominated benzenes, and a highly chlorinated norbornene compound called Dechlorane Plus. Most recently, we have begun measuring the atmospheric concentrations of several organophosphate esters, which are an increasing part of the flame retardant market. The interesting feature of this story is how one compound or set of compounds has followed another out of and into the marketplace even though none of them have been officially regulated. This replacement of one commercial product by another with similar functions shows that the chemical industry does respond to scientific environmental measurements and to the resulting bad publicity. This is a good thing. The problem is that often the replacement chemicals also become environmentally ubiquitous.

Comparative toxicity, oxidative stress and endocrine disruption potential of plasticizers in JEG-3 human placental cells.

PubMed

Pérez-Albaladejo, Elisabet; Fernandes, Denise; Lacorte, Silvia; Porte, Cinta

2017-02-01

Plasticizers are suspected to be toxic and/or to modulate or disrupt the endocrine system of humans and to cross the placental barrier, being embryonic and fetal development a particularly vulnerable period. This work investigates the comparative toxicity and ability to interfere with the synthesis of steroids and to generate reactive oxygen species (ROS) of a selected number of plasticizers, including bisphenol A (BPA), nonyl- (NP) and octylphenol (OP), benzyl butyl phthalate (BBP), dibutyl phthalate (DBP), di(2-ethylhexyl)phthalate (DEHP) and dimethyl phthalate (DMP), in the human placenta JEG-3 cells. Moreover, the bioavailability of chemicals in culture medium has been investigated. After 24h exposure, OP and NP showed the highest cytotoxicity (EC 50 : 36-40μM) followed by BPA (138-219μM), whereas no significant toxicity was observed for phthalates. Notwithstanding, BBP and DBP significantly decreased P450 aromatase activity (experimental IC 50 : 14-15μM), while NP and OP (20μM) increased the activity. Overall, this study evidences the differential toxicity and ability to modulate placental aromatase activity of some of the compounds nowadays used as plasticizers, and highlights the need of an accurate determination of the bioavailability of chemicals to improve the sensitivity of in-vitro tests. Copyright © 2016 Elsevier B.V. All rights reserved.

Comparison of different wastewater treatments for removal of selected endocrine-disruptors from paper mill wastewaters.

PubMed

Balabanič, Damjan; Hermosilla, Daphne; Merayo, Noemí; Klemenčič, Aleksandra Krivograd; Blanco, Angeles

2012-01-01

There is increasing concern about chemical pollutants that have the ability to mimic hormones, the so-called endocrine-disrupting compounds (EDCs). One of the main reasons for concern is the possible effect of EDCs on human health. EDCs may be released into the environment in different ways, and one of the most significant sources is industrial wastewater. The main objective of this research was to evaluate the treatment performance of different wastewater treatment procedures (biological treatment, filtration, advanced oxidation processes) for the reduction of chemical oxygen demand and seven selected EDCs (dimethyl phthalate, diethyl phthalate, dibutyl phthalate, benzyl butyl phthalate, bis(2-ethylhexyl) phthalate, bisphenol A and nonylphenol) from wastewaters from a mill producing 100 % recycled paper. Two pilot plants were running in parallel and the following treatments were compared: (i) anaerobic biological treatment followed by aerobic biological treatment, ultrafiltration and reverse osmosis (RO), and (ii) anaerobic biological treatment followed by membrane bioreactor and RO. Moreover, at lab-scale, four different advanced oxidation processes (Fenton reaction, photo-Fenton reaction, photocatalysis with TiO(2), and ozonation) were applied. The results indicated that the concentrations of selected EDCs from paper mill wastewaters were effectively reduced (100 %) by both combinations of pilot plants and photo-Fenton oxidation (98 %), while Fenton process, photocatalysis with TiO(2) and ozonation were less effective (70 % to 90 %, respectively).

Molecular, seasonal, and spatial distributions of organic aerosols from fourteen Chinese cities.

PubMed

Wang, Gehui; Kawamura, Kimitaka; Lee, Shuncheng; Ho, Kinfai; Cao, Junji

2006-08-01

Organic aerosols were studied at the molecular level in 14 coastal and inland mega-cities in China during winter and summer 2003. They are characterized by the abundant presence of n-alkanes (annual average, 340 ng m(-3)), fatty acids (769 ng m(-3)), sugars (412 ng m(-3)), and phthalates (387 ng m(-3)). In contrast, fatty alcohols, polyols/polyacids, lignin and resin products, sterols, polycyclic aromatic hydrocarbons (PAHs), and hopanes were detected as relatively minor components. n-Alkanes show a weak odd/even carbon predominance (CPI = 1.1) and PAHs show a predominance of benzo(b)fluoranthene, suggesting a serious contribution from fossil fuel (mainly coal) combustion. Their concentrations (except for phthalates and polyols/polyacids) were 2-15 times higher in winter than summer due to a significant usage of coal burning and an enhancement of atmospheric inversion layers. Phthalates were found to be more abundant in summer than winter, probably due to enhanced vaporization from plastics followed by adsorptive deposition on the pre-existing particles. Concentrations of total quantified compounds are extremely high (approximately 10 microg m(-3)) in the midwest (Chongqing and Xi'an) where active industrialization/urbanization is going on. This study shows that concentrations of the compounds detected are 1-3 orders of magnitude higher than those reported from developed countries.

Targeting mitochondria: Esters of rhodamine B with triterpenoids are mitocanic triggers of apoptosis.

PubMed

Wolfram, Ratna Kancana; Heller, Lucie; Csuk, René

2018-05-25

Triterpenoic acids, ursolic acid (1), oleanolic acid (2), glycyrrhetinic acid (3) and betulinic acid (4) were converted into their corresponding methyl 5-8 and benzyl esters 9-12 or benzyl amides 21-24. These derivatives served as starting materials for the synthesis of pink colored rhodamine B derivatives 25-36 which were screened for cytotoxicity in colorimetric SRB assays. All of the compounds were cytotoxic for a variety of human tumor cell lines. The activity of the benzyl ester derivatives 29-32 was lower than the cytotoxicity of the methyl esters 25-28. The benzyl amides 33-36 were the most cytotoxic compounds of this series. The most potential compound was a glycyrrhetinic acid rhodamine B benzyl amide 35. This compound showed activity against the different cancer cell lines in a two-digit to low three-digit nano-molar range. Staining experiments combined with fluorescence microscopy showed that this compound triggered apoptosis in A2780 ovarian carcinoma cells and acted as a mitocan. Copyright © 2018 Elsevier Masson SAS. All rights reserved.

Microbial Transformation of Esters of Chlorinated Carboxylic Acids

PubMed Central

Paris, D. F.; Wolfe, N. L.; Steen, W. C.

1984-01-01

Two groups of compounds were selected for microbial transformation studies. In the first group were carboxylic acid esters having a fixed aromatic moiety and an increasing length of the alkyl component. Ethyl esters of chlorine-substituted carboxylic acids were in the second group. Microorganisms from environmental waters and a pure culture of Pseudomonas putida U were used. The bacterial populations were monitored by plate counts, and disappearance of the parent compound was followed by gas-liquid chromatography as a function of time. The products of microbial hydrolysis were the respective carboxylic acids. Octanol-water partition coefficients (Kow) for the compounds were measured. These values spanned three orders of magnitude, whereas microbial transformation rate constants (kb) varied only 50-fold. The microbial rate constants of the carboxylic acid esters with a fixed aromatic moiety increased with an increasing length of alkyl substituents. The regression coefficient for the linear relationships between log kb and log Kow was high for group 1 compounds, indicating that these parameters correlated well. The regression coefficient for the linear relationships for group 2 compounds, however, was low, indicating that these parameters correlated poorly. PMID:16346459

Polyphenol fatty acid esters as serine protease inhibitors: a quantum-chemical QSAR analysis.

PubMed

Viskupicova, Jana; Danihelova, Martina; Majekova, Magdalena; Liptaj, Tibor; Sturdik, Ernest

2012-12-01

We investigated the ability of polyphenol fatty acid esters to inhibit the activity of serine proteases trypsin, thrombin, elastase and urokinase. Potent protease inhibition in micromolar range was displayed by rutin and rutin derivatives esterified with medium and long chain, mono- and polyunsaturated fatty acids (1e-m), followed by phloridzin and esculin esters with medium and long fatty acid chain length (2a-d, 3a-d), while unmodified compounds showed only little or no effect. QSAR study of the compounds tested provided the most significant parameters for individual inhibition activities, i.e. number of hydrogen bond donors for urokinase, molecular volume for thrombin, and solvation energy for elastase. According to the statistical analysis, the action of elastase inhibitors is opposed to those of urokinase and thrombin. Cluster analysis showed two groups of compounds: original polyphenols together with rutin esters with short fatty acid chain length and rutin esters with long fatty acid chain length.

Analysis of phenolic choline esters from seeds of Arabidopsis thaliana and Brassica napus by capillary liquid chromatography/electrospray- tandem mass spectrometry.

PubMed

Böttcher, Christoph; von Roepenack-Lahaye, Edda; Schmidt, Jürgen; Clemens, Stephan; Scheel, Dierk

2009-04-01

Total phenolic choline ester fractions prepared from seeds of Arabidopsis thaliana and Brassica napus were analyzed by capillary LC/ESI-QTOF-MS and direct infusion ESI-FTICR-MS. In addition to the dominating sinapoylcholine, 30 phenolic choline esters could be identified based on accurate mass measurements, interpretation of collision-induced dissociation (CID) mass spectra, and synthesis of selected representatives. The compounds identified so far include substituted hydroxycinnamoyl- and hydroxybenzoylcholines, respective monohexosides as well as oxidative coupling products of phenolic choline esters and monolignols. Phenolic choline esters are well separable by reversed-phase liquid chromatography and sensitively detectable using electrospray ionization mass spectrometry in positive ion mode. CID mass spectra obtained from molecular ions facilitate the characterization of both the type and substitution pattern of such compounds. Therefore, LC/ESI-MS/MS represents a valuable tool for comprehensive qualitative and quantitative analysis of this compound class. Copyright (c) 2009 John Wiley & Sons, Ltd.

Ozone reaction characteristics of indoor floor dust examined in the emission cell "FLEC".

PubMed

Vibenholt, Anni; Clausen, Per Axel; Wolkoff, Peder

2014-07-01

Ozone reacts with C-C double bonds in common indoor VOCs and SVOCs contained in indoor dust and may be catalytically degraded on dust surfaces. The reaction between floor dust and ozone was investigated in the FLEC emission cell at different ozone concentrations and relative humidities (0%, 25%, and 50% RH). One gram of dust was spread on a clean stainless steel plate which was placed in the FLEC. Steady state reaction rate (kDust) at 2.2 ppm ozone was determined for four different floor dust samples collected in Danish homes and offices. This high concentration was necessary in order to measure and determine the consumption in the outlet air from the FLEC. Measurements were corrected for FLEC wall effects by subtraction of the steady state reaction rate between ozone and a FLEC on a stainless steel plate without dust (kFLEC). The composition of organic compounds in the dust was analyzed by pressurized liquid extraction and thermal desorption GC-MS before and after ozone exposure. kFLEC was independent of the ozone concentration and the reaction was treated as first order. The same was indicated for kDust since it remained unchanged at 2.2 and 1.6 ppm ozone for one dust sample. However, the measured kDust in the FLEC should be considered an average rate constant due to the FLEC geometry. kDust was in the range 0.039-0.14s(-1) pr. g dust at 50% RH. kDust was 3 times higher at 25% RH than at 50% RH and 6 times higher than at 0% RH. The inhomogeneity of the dust was assessed by experiments in triplicate with a new portion of dust each time. The relative standard deviation of kDust at 50% RH was 6-20%. The major identified compounds before and after ozone exposure included aldehydes, saturated and unsaturated linear alkanoic acids, benzoic acid and their methyl esters, dimethyl esters, phthalates and traces of α-pinene and limonene. Substantial increase of C7-C9 aldehydes was observed after ozone exposure. Copyright © 2014 Elsevier Ltd. All rights reserved.

Continental bottled water assessment by stir bar sorptive extraction followed by gas chromatography-tandem mass spectrometry (SBSE-GC-MS/MS).

PubMed

Guart, Albert; Calabuig, Ignacio; Lacorte, Silvia; Borrell, Antonio

2014-02-01

This study was aimed to determine the presence of 69 organic contaminants in 77 representative bottled waters collected from 27 countries all over the world. All water samples were contained in polyethylene terephthalate bottles. Target compounds were (1) environmental contaminants (including 13 polycyclic aromatic hydrocarbons (PAHs), 31 pesticides including organochlorine (OCPs), organophosphorus, and pyrethroids; 7 polychlorinated biphenyls (PCBs); and 7 triazines) and (2) plasticizers (including 6 phthalates and 5 other compounds). Samples were analyzed by stir bar sorptive extraction followed by gas chromatography-tandem mass spectrometry. PAHs, OCPs, PCBs, and triazines, which are indicators of groundwater pollution, were not detected in most of the samples, except for naphthalene (0.005-0.202 μg/L, n = 16). On the other hand, plastic components were detected in 77 % of the samples. Most frequently detected compounds were dimethyl phthalate and benzophenone at concentrations of 0.005-0.125 (n = 41) and 0.014-0.921 (n = 32), respectively. Levels detected are discussed in terms of contamination origin and geographical distribution. Target compounds were detected at low concentrations. Results obtained showed the high quality of bottled water in the different countries around the world.

Liquid chromatography with diode array detection combined with spectral deconvolution for the analysis of some diterpene esters in Arabica coffee brew.

PubMed

Erny, Guillaume L; Moeenfard, Marzieh; Alves, Arminda

2015-02-01

In this manuscript, the separation of kahweol and cafestol esters from Arabica coffee brews was investigated using liquid chromatography with a diode array detector. When detected in conjunction, cafestol, and kahweol esters were eluted together, but, after optimization, the kahweol esters could be selectively detected by setting the wavelength at 290 nm to allow their quantification. Such an approach was not possible for the cafestol esters, and spectral deconvolution was used to obtain deconvoluted chromatograms. In each of those chromatograms, the four esters were baseline separated allowing for the quantification of the eight targeted compounds. Because kahweol esters could be quantified either using the chromatogram obtained by setting the wavelength at 290 nm or using the deconvoluted chromatogram, those compounds were used to compare the analytical performances. Slightly better limits of detection were obtained using the deconvoluted chromatogram. Identical concentrations were found in a real sample with both approaches. The peak areas in the deconvoluted chromatograms were repeatable (intraday repeatability of 0.8%, interday repeatability of 1.0%). This work demonstrates the accuracy of spectral deconvolution when using liquid chromatography to mathematically separate coeluting compounds using the full spectra recorded by a diode array detector. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Experimental investigation of the auto-ignition characteristics of oxygenated reference fuel compounds

NASA Astrophysics Data System (ADS)

Walton, Stephen Michael

The increased use of biofuels presents an opportunity to improve combustion performance while simultaneously reducing greenhouse gases and pollutant emissions. This work focused on improving the fundamental understanding of the auto-ignition chemistry of oxygenated reference fuel compounds. A systematic study of the effects of ester structure on ignition chemistry was performed using the University of Michigan Rapid Compression Facility. The ignition properties of the ester compounds were investigated over a broad range of pressures (P=5-20 atm) and temperatures (T=850-1150 K) which are directly relevant to advanced combustion engine strategies. Ignition delay times for five esters were determined using the RCF. The esters were selected to systematically consider the chemical structure of the compounds. Three esters were saturated: methyl butanoate, butyl methanoate, and ethyl propanoate; and two were unsaturated: methyl crotonate and methyl trans-3-hexenoate. The unsaturated esters were more reactive than their saturated counterparts, with the largest unsaturated ester, methyl trans-3-hexenoate having the highest reactivity. Two isomers of the saturated esters, butyl methanoate and ethyl propanoate, were more reactive than the isomer methyl butanoate. The results are explained if we assume that butyl methanoate and ethyl propanoate form intermediate ring structures which decompose more rapidly than esters such as methyl butanoate, which do not form ring structures. Modeling studies of the reaction chemistry were conducted for methyl butanoate and ethyl propanoate, for which detailed mechanisms were available in the literature. The new experimental data indicated that literature rate coefficients for some of the methyl butanoate/HO2 reactions were too fast. Modifying these within the theoretical uncertainties for the reaction rates, led to excellent agreement between the model predictions and the experimental data. Comparison of the modeling results with the intermediates measured during methyl butanoate ignition indicated that pathways leading to the formation of small hydrocarbons are relatively well represented in the reaction mechanism. The results of this work provide archival benchmark data for improved understanding of the dominant reaction pathways and species controlling the auto-ignition of oxygenated reference fuel compounds. These data also provide a path for continued development of chemical kinetic models to optimize practical combustion systems.

Oxygenated N-Acyl Alanine Methyl Esters (NAMEs) from the Marine Bacterium Roseovarius tolerans EL-164.

PubMed

Bruns, Hilke; Herrmann, Jennifer; Müller, Rolf; Wang, Hui; Wagner Döbler, Irene; Schulz, Stefan

2018-01-26

The marine bacterium Roseovarius tolerans EL-164 (Rhodobacteraceae) can produce unique N-acylalanine methyl esters (NAMEs) besides strucutrally related N-acylhomoserine lactones (AHLs), bacterial signaling compounds widespread in the Rhodobacteraceae. The structures of two unprecedented NAMEs carrying a rare terminally oxidized acyl chain are reported here. The compounds (Z)-N-16-hydroxyhexadec-9-enoyl-l-alanine methyl ester (Z9-16-OH-C16:1-NAME, 3) and (Z)-N-15-carboxypentadec-9-enoyl-l-alanine methyl ester (16COOH-C16:1-NAME, 4) were isolated, and the structures were determined by NMR and MS experiments. Both compounds were synthesized to prove assignments and to test their biological activity. Finally, non-natural, structurally related Z9-3-OH-C16:1-NAME (18) was synthesized to investigate the mass spectroscopy of structurally related NAMEs. Compound 3 showed moderate antibacterial activity against microorganisms such as Bacillus, Streptococcus, Micrococcus, or Mucor strains. In contrast to AHLs, quorum-sensing or quorum-quenching activity was not observed.

Indications of Transformation Products from Hydraulic Fracturing Additives in Shale-Gas Wastewater.

PubMed

Hoelzer, Kathrin; Sumner, Andrew J; Karatum, Osman; Nelson, Robert K; Drollette, Brian D; O'Connor, Megan P; D'Ambro, Emma L; Getzinger, Gordon J; Ferguson, P Lee; Reddy, Christopher M; Elsner, Martin; Plata, Desiree L

2016-08-02

Unconventional natural gas development (UNGD) generates large volumes of wastewater, the detailed composition of which must be known for adequate risk assessment and treatment. In particular, transformation products of geogenic compounds and disclosed additives have not been described. This study investigated six Fayetteville Shale wastewater samples for organic composition using a suite of one- and two-dimensional gas chromatographic techniques to capture a broad distribution of chemical structures. Following the application of strict compound-identification-confidence criteria, we classified compounds according to their putative origin. Samples displayed distinct chemical distributions composed of typical geogenic substances (hydrocarbons and hopane biomarkers), disclosed UNGD additives (e.g., hydrocarbons, phthalates such as diisobutyl phthalate, and radical initiators such as azobis(isobutyronitrile)), and undisclosed compounds (e.g., halogenated hydrocarbons, such as 2-bromohexane or 4-bromoheptane). Undisclosed chloromethyl alkanoates (chloromethyl propanoate, pentanoate, and octanoate) were identified as potential delayed acids (i.e., those that release acidic moieties only after hydrolytic cleavage, the rate of which could be potentially controlled), suggesting they were deliberately introduced to react in the subsurface. In contrast, the identification of halogenated methanes and acetones suggested that those compounds were formed as unintended byproducts. Our study highlights the possibility that UNGD operations generate transformation products and underscores the value of disclosing additives injected into the subsurface.

NTP Carcinogenesis Bioassay of Diallyl Phthalate (CAS No. 131-17-9) in B6C3F1 Mice (Gavage Study).

PubMed

1983-04-01

Diallyl phthalate is a widely used crosslinking agent for unsaturated polyesters. Diallyl phthalate or diallyl phthalate polyester blends are used primarily as plasticizers and carriers for adding catalysts and pigments to polyesters and in molding, electrical parts, laminating compounds, and impregnation of metal castings. Rubber compounds, epoxy formulations, and polyurethane foams may also contain diallyl phthalate. Annual production of diallyl phthalate in the United States exceeds 5,000 pounds; precise figures are not available. A NTP Carcinogenesis bioassay of diallyl phthalate (99% pure) was conducted by administering 0 (vehicle control), 150, or 300 mg/kg diallyl phthalate in corn oil by gavage, 5 days per week for 103 weeks, to groups of 50 male and 50 female B6C3F1 mice. Survival rates and mean body weights of dosed mice were not different from those of the controls, and pathological lesions unrelated to proliferative changes were not observed. Therefore, a maximally tolerated dose for the purposes of carcinogenicity testing may not have been achieved. The incidences of lymphoma and either lymphoma or leukemia in dosed male mice were no significantly greater than those in the controls according to pairwise comparisons (P=0.051 to P=0.096), but the trend tests were statistically significant by either life table or incidental tumor analysis (P=0.031 to P=0.045). The incidence of lymphomas in the high-dose male mice was 12/50 (24%) in comparison with 6/50 (12%) in the controls. Recent historical incidences at the performing laboratory and in the NTP Bioassay Program were 18/120 (15%) and 71/661 (11%), respectively. Since the incidence of high-dose male mice with leukemia was not significantly greater than that of concurrent or historical controls at the performing laboratory by pairwise comparisons, this marginal increase was considered only to be equivocally related to diallyl phthalate administration. Increased incidences of squamous cell papillomas, hyperplasia, and inflammatory lesions of the forestomach were observed in diallyl phthalate-dosed mice of both sexes in a dose-related manner. Papillomas of the forestomach were observed in 0%, 2%, and 4% of the control, low-dose, and high-dose mice of both sexes. The recent historical incidence of this tumor in gavage control mice from both the performing laboratory and other laboratories within the Bioassay Program was less than 1%. Forestomach hyperplasia was diagnosed in 0%, 15%, and 18%, and in 8%, 2%, and 29% of the control, low-dose, and high-dose male and female mice, respectively; chronic inflammation of the forestomach was diagnosed in 0%, 9%, and 16% and in 4%, 2%, and 18% of the control, low-dose, and high-dose male and female mice, respectively. Because of the numerical elevation of the forestomach papillomas in the high-dose mice of both sexes, the concomitant observation of dose related forestomach hyperplasia, and the rarity of this tumor in corn oil (gavage) control B6C3F1 mice, the development of squamous cell papillomas of the forestomach may have been related to diallyl phthalate administration. Under the conditions of this bioassay, the development of chronic inflammation and hyperplasia of the forestomach in both male and female B6C3F1 mice was considered to be related to the administration of diallyl phthalate. The development of squamous cell papillomas of the forestomach may also have been related to chemical administration, but the available data are insufficient to indicate a clear cause and effect relationship. An increase in the incidence of male mice with lymphomas was observed, but this increase was considered only to be equivocally related to diallyl phthalate administration. The results of this bioassay, therefore, do not indicate that diallyl phthalate is carcinogenic in B6C3F1 mice, although a maximum tolerated dose may not have been achieved. A carcinogenicity study by the National Toxicology Program of diallyl phthalate in male and female Fisher 344/N rats, employing daily gavage doses of 0 (vehicle control), 50, or 100 mg/kg boicology Program of diallyl phthalate in male and female Fisher 344/N rats, employing daily gavage doses of 0 (vehicle control), 50, or 100 mg/kg body weight is currently being evaluated. Levels of Evidence of Carcinogenicity: Male Mice: Equivocal Female Mice: Equivocal

Comparative study on cytogenetic damage induced by homo-aza-steroidal esters in human lymphocytes.

PubMed

Mourelatos, D; Papageorgiou, A; Boutis, L; Catsoulacos, P

1995-02-01

The effect of P[N,N-bis(2-chloroethyl)amino]phenylacetate esters of 3 beta-hydroxy-N-methyl-17 alpha-aza-D-homo-5 alpha-androstan-17-one (compound 3) and 3 beta-hydroxy-17 alpha-aza-D-homo-5 alpha-androstane (compound 2) on sister-chromatid exchange (SCE) frequencies and on human lymphocytes proliferation kinetics was studied. The results are compared with those of the P[N,N-bis(2-chloroethyl)amino]phenylacetate esters of 3 beta-hydroxy-17 alpha-aza-D-homo-5 alpha-androstan-17-one (compound 1). All compounds were found to be active in inducing markedly increased SCE rates and cell division delays. A correlation between potency for SCE induction, effectiveness in cell division delay and previously established antitumour activity of these compounds was observed.

Calibration of two passive air samplers for monitoring phthalates and brominated flame-retardants in indoor air.

PubMed

Saini, Amandeep; Okeme, Joseph O; Goosey, Emma; Diamond, Miriam L

2015-10-01

Two passive air samplers (PAS), polyurethane foam (PUF) disks and Sorbent Impregnated PUF (SIP) disks, were characterized for uptake of phthalates and brominated flame-retardants (BFRs) indoors using fully and partially sheltered housings. Based on calibration against an active low-volume air sampler for gas- and particle-phase compounds, we recommend generic sampling rates of 3.5±0.9 and 1.0±0.4 m(3)/day for partially and fully sheltered housing, respectively, which applies to gas-phase phthalates and BFRs as well as particle-phase DEHP (the later for the partially sheltered PAS). For phthalates, partially sheltered SIPs are recommended. Further, we recommend the use of partially sheltered PAS indoors and a deployment period of one month. The sampling rate for the partially sheltered PUF and SIP of 3.5±0.9 m(3)/day is indistinguishable from that reported for fully sheltered PAS deployed outdoors, indicating the role of the housing outdoors to minimize the effect of variable wind velocities on chemical uptake, versus the partially sheltered PAS deployed indoors to maximize chemical uptake where air flow rates are low. Copyright © 2015. Published by Elsevier Ltd.

In vitro antifungal potentials of bioactive compound oleic acid, 3-(octadecyloxy) propyl ester isolated from Lepidagathis cristata Willd. (Acanthaceae) inflorescence.

PubMed

Abubacker, Maghdu Nainamohamed; Devi, Palaniyappan Kamala

2014-09-01

To identify bioactive compound oleic acid, 3-(octadecyloxy) propyl ester from Lepidagathis cristata Willd. (L. cristata) and to assess antifungal potentials of the isolated compound. Aqueous extracts of L. cristata inflorescence were used for this study. The major bioactive compound isolated was tested for antifungal activities. The major bioactive compound oleic acid, 3-(octadecyloxy) propyl ester was isolated from the inflorescence of L. cristata. The bioactive compound was tested for antifungal potentials and found to be highly effective to plant pathogenic fungi Colletotrichum fulcatum NCBT 146, Fusarium oxysporum NCBT 156 and Rhizoctonia solani NCBT 196 as well as for the human pathogenic fungi Curvularia lunata MTCC 2030 and Microsporum canis MTCC 2820. The results justify the antifungal potentials of both plant and human pathogenic fungi. The plant bioactive compound will be helpful in herbal antifungal formulations. Copyright © 2014 Hainan Medical College. Published by Elsevier B.V. All rights reserved.

Histone deacetylase 4 promotes ubiquitin-dependent proteasomal degradation of Sp3 in SH-SY5Y cells treated with di(2-ethylhexyl)phthalate (DEHP), determining neuronal death

DOE Office of Scientific and Technical Information (OSTI.GOV)

Guida, Natascia; Laudati, Giusy; Galgani, Mario

Phthalates, phthalic acid esters, are widely used as plasticizers to produce polymeric materials in industrial production of plastics and daily consumable products. Animal studies have shown that di(2-ethylhexyl)phthalate (DEHP) may cause toxic effects in the rat brain. In the present study, chronic exposure to DEHP (0.1–100 μM) caused dose-dependent cell death via the activation of caspase-3 in neuroblastoma cells. Intriguingly, this harmful effect was prevented by the pan-histone deacetylase (HDAC) inhibitor trichostatin A, by the class II HDAC inhibitor MC-1568, but not by the class I HDAC inhibitor MS-275. Furthermore, DEHP reduced specificity protein 3 (Sp3) gene expression, but notmore » Sp3 mRNA, after 24 and 48 h exposures. However, Sp3 protein reduction was prevented by pre-treatment with MC-1568, suggesting the involvement of class II HDACs in causing this effect. Then, we investigated the possible relationship between DEHP-induced neuronal death and the post-translational mechanisms responsible for the down-regulation of Sp3. Interestingly, DEHP-induced Sp3 reduction was associated to its deacetylation and polyubiquitination. Co-immunoprecipitation studies showed that Sp3 physically interacted with HDAC4 after DEHP exposure, while HDAC4 inhibition by antisense oligodeoxynucleotide reverted the DEHP-induced degradation of Sp3. Notably, Sp3 overexpression was able to counteract the detrimental effect induced by DEHP. Taken together, these results suggest that DEHP exerts its toxic effect by inducing deacetylation of Sp3 via HDAC4, and afterwards, Sp3-polyubiquitination. - Highlights: • Di(2-ethylhexyl)phthalate (DEHP) is cytotoxic to SH-SY5Y cells and cortical neurons. • DEHP-induced cytotoxicity is mediated by apoptosis. • DEHP-induced apoptotic cell death is inhibited by class II HDAC MC-1568. • DEHP neurotoxicity is caused by HDAC4-mediated Sp3 degradation by ubiquitin.« less

SPE-UPLC-MS/MS for the determination of phthalate monoesters in rats urine and its application to study the effects of food emulsifier on the bioavailability of priority controlling PAEs.

PubMed

Xu, R; Gao, H T; Zhu, F; Cao, W X; Yan, Y H M; Zhou, X; Xu, Q; Ji, W L

2016-02-15

This research was mainly focused on the effects of food emulsifier on the bioavailability of six priority controlling phthalate acid esters (PAEs) for the further accurate assessment of their toxic effects, using the corresponding phthalate acid monoesters (PAMEs) in rats urine as biomarkers. Glycerin monostearate was chosen as typical food emulsifier. A method was established to determine PAMEs in urine from rats either in experimental group (integrated gavaged with glycerin monostearate and PAEs) or in control group (gavaged with PAEs only), by using solid-phase extraction (SPE) coupled with ultra performance liquid chromatography tandem mass spectrometry (SPE-UPLC-MS/MS). Extraction recoveries were more than 75% for all the PAMEs; the calibration curve was linear in the range of 1.0-1000.0ng/mL with R(2)>0.995; the limits of detection (LOD) were 0.30ng/mL-0.50ng/mL. In addition, by analysing quality control (QC) urine samples in 3 days, it showed that the method was precise and accurate, for the intra-day and inter-day RSD within 16%, and the accuracy more than 82%. Internal exposure amount of all PAEs in experimental group was significantly higher than that in control group with p values of less than 0.05 except for butyl benzyl phthalates (BBP) (P=0.07). The bioavailability of all PAEs ranged from 5.03% to 109.35% with the presence of food emulsifiers glycerin monostearate, observably higher than that without glycerin monostearate (1.12% to 54.39%). It indicated that food emulsifiers increased the bioavailability of PAEs and may lead to potential food safety risk, which should bring awareness and be further studied. Copyright © 2016 Elsevier B.V. All rights reserved.

Effect of mono-(2-ethylhexyl) phthalate on steroid production of human granulosa cells

DOE Office of Scientific and Technical Information (OSTI.GOV)

Reinsberg, Jochen; Wegener-Toper, Petra; Ven, Katrin van der

2009-08-15

The phthalate ester mono-(2-ethylhexyl) phthalate (MEHP) is the active metabolite of di-(2-ethylhexyl) phthalate, a high-production-volume chemical used as a plasticizer and solvent in numerous consumer products. MEHP has been demonstrated to be a reproductive toxicant in rodents decreasing estradiol and progesterone production in preovulatory granulosa cells. In the present study, we examined the effect of MEHP on steroid production of human granulosa-lutein (GL) cells. Human GL cells collected from women undergoing in vitro fertilization were cultured in medium containing FSH, hCG and 8-Br-cAMP, respectively, together with various concentrations of MEHP (0-500 {mu}mol L{sup -1}). After incubation for 48 h estradiolmore » and progesterone were assayed in the spent culture medium. Furthermore, aromatase activity and mRNA levels of GL cells were determined. Basal as well as FSH-, hCG- and 8-Br-cAMP-stimulated estradiol production of GL cells was suppressed by MEHP in a dose-dependent manner (IC{sub 50} = 105 {mu}mol L{sup -1}, 138 {mu}mol L{sup -1}, 49 {mu}mol L{sup -1} and 78 {mu}mol L{sup -1}). Furthermore aromatase activity and mRNA levels were reduced in GL cells cultured with MEHP. In contrast, MEHP did not alter the production of progesterone up to a concentration of 167 {mu}mol L{sup -1}. The present data indicate that MEHP is a specific inhibitor of estradiol production in human GL cells with a post-cAMP site of action. The inhibition of estradiol production obviously results from a reduction of aromatase activity on the transcript level. As the in vitro effective doses of MEHP are within the range of real environmental exposure levels an inhibitory effect on estrogen production in vivo seems to be possi0009b.« less

Distribution of phthalates, pesticides and drug residues in the dissolved, particulate and sedimentary phases from transboundary rivers (France-Belgium).

PubMed

Net, Sopheak; Rabodonirina, Suzanah; Sghaier, Rafika Ben; Dumoulin, David; Chbib, Chaza; Tlili, Ines; Ouddane, Baghdad

2015-07-15

Various drug residues, pesticides and phthalates are ubiquitous in the environment. Their presence in the environment has attracted considerable attention due to their potential impacts on ecosystem functioning and on public health. In this work, 14 drug residues, 24 pesticides and 6 phthalates have been quantified in three matrices (in the dissolved phase, associated to suspended solid matter (SSM), and in sediment) collected from fifteen watercourses and rivers located in a highly industrialized zone at the cross-border area of Northern France and Belgium. The extractions have been carried out using accelerated solvent extraction (ASE) for solid matrices (SSM and sediment) and using solid phase extraction (SPE) for liquid matrix. The final extract was analyzed using GC-MS technique. Among the three classes of compounds, phthalates have been found at highest level compared to pesticides and drug residues. The Σ6PAE concentrations were ranging from 17.2±2.58 to 179.1±26.9μgL(-1) in dissolved phase, from 2.9±0.4 to 21.1±3.2μgL(-1) in SSM and from 1.1±0.2 to 11.9±1.8μgg(-1)dw in sediment. The Σ14drug residue concentrations were lower than 1.3μgL(-1) in the dissolved phases, lower than 30ngL(-1) associated to SSM and from nondetectable levels to 60.7±9.1ngg(-1)dw in sediment. For pesticides, all compounds were below the LOQ values in dissolved phase and in sediment, and only EPTC could be quantified in SSM. Copyright © 2015 Elsevier B.V. All rights reserved.

Latex paint as a delivery vehicle for diethylphthalate and di-n-butylphthalate: predictable boundary layer concentrations and emission rates.

PubMed

Schripp, Tobias; Salthammer, Tunga; Fauck, Christian; Bekö, Gabriel; Weschler, Charles J

2014-10-01

The description of emission processes of volatile and semi-volatile organic compounds (VOCs and SVOCs) from building products requires a detailed understanding of the material and the air flow conditions at the surface boundary. The mass flux between the surface of the material and air depends on the mass transfer coefficient (hm) through the boundary layer, the gas phase concentration of the target compound immediately adjacent to the material (y0), and the gas-phase concentration in bulk air (y(t)). In the present study emission experiments were performed in two chambers of quite different sizes (0.25 m(3) and 55 m(3)), and, in the larger chamber, at two different temperatures (23°C and 30°C). The emitting material was latex wall paint that had been doped with two plasticizers, diethylphthalate (DEP) and di-n-butylphthalate (DnBP). The phthalate content in the paint was varied in the small chamber experiment to evaluate the impact of the initial concentration in the bulk material (C0) on the emission rate. Boundary layer theory was applied to calculate hm for the specific phthalates from the Sherwood number (Sh) and the diffusion coefficient (Dair). Then y0 was determined based on the bulk gas-phase concentration at steady state (y¯). For both, DEP and DnBP, the y0 obtained was lower than the respective saturation vapor pressure (Ps). Furthermore, for both phthalates in latex paint, the material/air partition coefficient (C0/y0) was close in value to the octanol/air partition coefficient (KOA). This study provides a basis for designing phthalate emitting reference materials that mimic the emission behavior of common building materials. Copyright © 2014 Elsevier B.V. All rights reserved.

Dicarboxylic esters: Useful tools for the biocatalyzed synthesis of hybrid compounds and polymers

PubMed Central

Bassanini, Ivan; Hult, Karl

2015-01-01

Summary Dicarboxylic acids and their derivatives (esters and anhydrides) have been used as acylating agents in lipase-catalyzed reactions in organic solvents. The synthetic outcomes have been dimeric or hybrid derivatives of bioactive natural compounds as well as functionalized polyesters. PMID:26664578

Composition of Lutein Ester Regioisomers in Marigold Flower, Dietary Supplement, and Herbal Tea.

PubMed

Abdel-Aal, El-Sayed M; Rabalski, Iwona

2015-11-11

Characterization of lutein and its esters in a health product is necessary for its efficacy. In the current study lutein ester regioisomers were quantified and identified in several dietary supplements and herbal teas in comparison with marigold flower, the commercial source of lutein. The products were extracted with three solvents and separated on a C30 column. The separated esters were identified/confirmed with LC-MS in APCI+ve mode with the use of synthetic lutein esters. The total content of lutein esters substantially varied among marigold flowers (167-5752 μg/g), supplements (88,000-110,700 μg/g), and herbal teas (12.4-91.3 μg/g). Lutein supplement had a lutein profile similar to that of marigold flower, whereas herbal tea showed an extremely different profile. Lutein dipalmitate was the dominant compound in supplements and marigold flowers followed by lutein 3'-O-myristate-3-O-palmitate and lutein 3'-O-palmitate-3-O-myristate. Lutein was the major compound in marigold herbal tea with small amounts of lutein mono- and diesters. Differences in the concentration and composition of lutein compounds among marigold products could indicate distinct product quality and lutein bioavailability.

Differential DNA methylation at conserved non-genic elements and evidence for transgenerational inheritance following developmental exposure to mono(2-ethylhexyl) phthalate and 5-azacytidine in zebrafish.

PubMed

Kamstra, Jorke H; Sales, Liana Bastos; Aleström, Peter; Legler, Juliette

2017-01-01

Exposure to environmental stressors during development may lead to latent and transgenerational adverse health effects. To understand the role of DNA methylation in these effects, we used zebrafish as a vertebrate model to investigate heritable changes in DNA methylation following chemical-induced stress during early development. We exposed zebrafish embryos to non-embryotoxic concentrations of the biologically active phthalate metabolite mono(2-ethylhexyl) phthalate (MEHP, 30 µM) and the DNA methyltransferase 1 inhibitor 5-azacytidine (5AC, 10 µM). Direct, latent and transgenerational effects on DNA methylation were assessed using global, genome-wide and locus-specific DNA methylation analyses. Following direct exposure in zebrafish embryos from 0 to 6 days post-fertilization, genome-wide analysis revealed a multitude of differentially methylated regions, strongly enriched at conserved non-genic elements for both compounds. Pathways involved in adipogenesis were enriched with the putative obesogenic compound MEHP. Exposure to 5AC resulted in enrichment of pathways involved in embryonic development and transgenerational effects on larval body length. Locus-specific methylation analysis of 10 differentially methylated sites revealed six of these loci differentially methylated in sperm sampled from adult zebrafish exposed during development to 5AC, and in first and second generation larvae. With MEHP, consistent changes were found at 2 specific loci in first and second generation larvae. Our results suggest a functional role for DNA methylation on cis-regulatory conserved elements following developmental exposure to compounds. Effects on these regions are potentially transferred to subsequent generations.

Development of a simple and valid method for the trace determination of phthalate esters in human plasma using dispersive liquid-liquid microextraction coupled with gas chromatography-mass spectrometry.

PubMed

Ebrahim, Karim; Poursafa, Parinaz; Amin, Mohammad Mehdi

2017-11-01

A new method was developed for the trace determination of phthalic acid esters in plasma using dispersive liquid-liquid microextraction and gas chromatography with mass spectrometry analysis. Plasma proteins were efficiently precipitated by trichloroacetic acid and then a mixture of chlorobenzene (as extraction solvent) and acetonitrile (as dispersive solvent) rapidly injected to clear supernatant using a syringe. After centrifuging, chlorobenzene sedimented at the bottom of the test tube. 1 μL of this sedimented phase was injected into the gas chromatograph for phthalic acid esters analysis. Different factors affecting the extraction performance, such as the type of extraction and dispersive solvent, their volume, extraction time, and the effects of salt addition were investigated and optimized. Under the optimum conditions, the enrichment factors and extraction recoveries were satisfactory and ranged between 820-1020 and 91-97%, respectively. The linear range was wide (50-1000 ng/mL) and limit of detection was very low (1.5-2.5 ng/mL for all analytes). The relative standard deviations for analysis of 1 μg/mL of the analytes were between 3.2-6.1%. Salt addition showed no significant effect on extraction recovery. Finally, the proposed method was successfully utilized for the extraction and determination of the phthalic acid esters in human plasma samples and satisfactory results were obtained. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Space simulation ultimate pressure lowered two decades by removal of diffusion pump oil contaminants during operation

NASA Technical Reports Server (NTRS)

Buggele, A. E.

1973-01-01

The complex problem why large space simulation chambers do not realize the true ultimate vacuum was investigated. Some contaminating factors affecting diffusion pump performance have been identified and some advances in vacuum/distillation/fractionation technology have been achieved which resulted in a two decade or more lower ultimate pressure. Data are presented to show the overall or individual contaminating effect of commonly used phthalate ester plasticizers of 390 to 530 molecular weight on diffusion pump performance. Methods for removing contaminants from diffusion pump silicone oil during operation and reclaiming contaminated oil by high vacuum molecular distillation are described.

Using exposure prediction tools to link exposure and dosimetry for risk-based decisions: A case study with phthalates.

PubMed

Moreau, Marjory; Leonard, Jeremy; Phillips, Katherine A; Campbell, Jerry; Pendse, Salil N; Nicolas, Chantel; Phillips, Martin; Yoon, Miyoung; Tan, Yu-Mei; Smith, Sherrie; Pudukodu, Harish; Isaacs, Kristin; Clewell, Harvey

2017-10-01

A few different exposure prediction tools were evaluated for use in the new in vitro-based safety assessment paradigm using di-2-ethylhexyl phthalate (DEHP) and dibutyl phthalate (DnBP) as case compounds. Daily intake of each phthalate was estimated using both high-throughput (HT) prediction models such as the HT Stochastic Human Exposure and Dose Simulation model (SHEDS-HT) and the ExpoCast heuristic model and non-HT approaches based on chemical specific exposure estimations in the environment in conjunction with human exposure factors. Reverse dosimetry was performed using a published physiologically based pharmacokinetic (PBPK) model for phthalates and their metabolites to provide a comparison point. Daily intakes of DEHP and DnBP were estimated based on the urinary concentrations of their respective monoesters, mono-2-ethylhexyl phthalate (MEHP) and monobutyl phthalate (MnBP), reported in NHANES (2011-2012). The PBPK-reverse dosimetry estimated daily intakes at the 50th and 95th percentiles were 0.68 and 9.58 μg/kg/d and 0.089 and 0.68 μg/kg/d for DEHP and DnBP, respectively. For DEHP, the estimated median from PBPK-reverse dosimetry was about 3.6-fold higher than the ExpoCast estimate (0.68 and 0.18 μg/kg/d, respectively). For DnBP, the estimated median was similar to that predicted by ExpoCast (0.089 and 0.094 μg/kg/d, respectively). The SHEDS-HT prediction of DnBP intake from consumer product pathways alone was higher at 0.67 μg/kg/d. The PBPK-reverse dosimetry-estimated median intake of DEHP and DnBP was comparable to values previously reported for US populations. These comparisons provide insights into establishing criteria for selecting appropriate exposure prediction tools for use in an integrated modeling platform to link exposure to health effects. Copyright © 2017 The Authors. Published by Elsevier Ltd.. All rights reserved.

Alkyl Phenols and Diethylhexyl Phthalate in Tissues of Sheep Grazing Pastures Fertilized with Sewage Sludge or Inorganic Fertilizer

PubMed Central

Rhind, Stewart M.; Kyle, Carol E.; Telfer, Gillian; Duff, Elizabeth I.; Smith, Alistair

2005-01-01

We studied selected tissues from ewes and their lambs that were grazing pastures fertilized with either sewage sludge (treated) or inorganic fertilizer (control) and determined concentrations of alkylphenols and phthalates in these tissues. Mean tissue concentrations of alkylphenols were relatively low (< 10–400 μg/kg) in all animals and tissues. Phthalates were detected in tissues of both control and treated animals at relatively high concentrations (> 20,000 μg/kg in many tissue samples). The use of sludge as a fertilizer was not associated with consistently increased concentrations of either alkylphenols or phthalates in the tissues of animals grazing treated pastures relative to levels in control animal tissues. Concentrations of the two classes of chemicals differed but were of a similar order of magnitude in liver and muscle as well as in fat. Concentrations of each class of compound were broadly similar in tissues derived from ewes and lambs. Although there were significant differences (p < 0.01 or p < 0.001) between years (cohorts) in mean tissue concentrations of both nonylphenol (NP) and phthalate in each of the tissues from both ewes and lambs, the differences were not attributable to either the age (6 months or 5 years) of the animal or the duration of exposure to treatments. Octylphenol concentrations were generally undetectable. There was no consistent cumulative outcome of prolonged exposure on the tissue concentrations of either class of pollutant in any ewe tissue. Mean tissue concentrations of phthalate were higher (p < 0.001) in the liver and kidney fat of male compared with female lambs. We suggest that the addition of sewage sludge to pasture is unlikely to cause large increases in tissue concentrations of NP and phthalates in sheep and other animals with broadly similar diets and digestive systems (i.e., domestic ruminants) grazing such pasture. PMID:15811823

Chemical Analysis and Risk Assessment of Diethyl Phthalate in Alcoholic Beverages with Special Regard to Unrecorded Alcohol

PubMed Central

Leitz, Jenny; Kuballa, Thomas; Rehm, Jürgen; Lachenmeier, Dirk W.

2009-01-01

Background Phthalates are synthetic compounds with a widespread field of applications. For example, they are used as plasticizers in PVC plastics and food packaging, or are added to personal care products. Diethyl phthalate (DEP) may be used to denature alcohol, e.g., for cosmetic purposes. Public health concerns of phthalates include carcinogenic, teratogenic, hepatotoxic and endocrine effects. The aim of this study was to develop and validate a method for determining phthalates in alcohol samples and to provide a risk assessment for consumers of such products. Methodology/Principal Findings A liquid-liquid extraction procedure was optimized by varying the following parameters: type of extraction solvent (cyclohexane, n-hexane, 1,1,2-trichlorotrifluoroethane), the ratio extraction solvent/sample volume (1∶1 to 50∶1) and the number of extraction repetitions (1–10). The best extraction yield (99.9%) was achieved with the solvent 1,1,2-trichlorotrifluoroethane, an extraction solvent volume/sample volume ratio of 10∶1 and a double extraction. For quantification, gas chromatography/mass spectrometry with deuterated internal standards was used. The investigated samples were alcoholic beverages and unrecorded alcohol products from different countries (n = 257). Two unrecorded alcohol samples from Lithuania contained diethyl phthalate in concentrations of 608 mg/L and 210 mg/L. Conclusions/Significance The consumption of the phthalate-positive unrecorded alcohols would exceed tolerable daily intakes as derived from animal experiments. Both positive samples were labelled as cosmetic alcohol, but had clearly been offered for human consumption. DEP seems to be unsuitable as a denaturing agent as it has no effect on the organoleptic properties of ethanol. In light of our results that DEP might be consumed by humans in unrecorded alcohols, the prohibition of its use as a denaturing agent should be considered. PMID:19956573

Aminomethylphosphonic Acid and Methoxyacetic Acid Induce Apoptosis in Prostate Cancer Cells

PubMed Central

Parajuli, Keshab R.; Zhang, Qiuyang; Liu, Sen; You, Zongbing

2015-01-01

Aminomethylphosphonic acid (AMPA) and its parent compound herbicide glyphosate are analogs to glycine, which have been reported to inhibit proliferation and promote apoptosis of cancer cells, but not normal cells. Methoxyacetic acid (MAA) is the active metabolite of ester phthalates widely used in industry as gelling, viscosity and stabilizer; its exposure is associated with developmental and reproductive toxicities in both rodents and humans. MAA has been reported to suppress prostate cancer cell growth by inducing growth arrest and apoptosis. However, it is unknown whether AMPA and MAA can inhibit cancer cell growth. In this study, we found that AMPA and MAA inhibited cell growth in prostate cancer cell lines (LNCaP, C4-2B, PC-3 and DU-145) through induction of apoptosis and cell cycle arrest at the G1 phase. Importantly, the AMPA-induced apoptosis was potentiated with the addition of MAA, which was due to downregulation of the anti-apoptotic gene baculoviral inhibitor of apoptosis protein repeat containing 2 (BIRC2), leading to activation of caspases 7 and 3. These results demonstrate that the combination of AMPA and MAA can promote the apoptosis of prostate cancer cells, suggesting that they can be used as potential therapeutic drugs in the treatment of prostate cancer. PMID:26006246

Characteristics of organic matter in PM2.5 from an e-waste dismantling area in Taizhou, China.

PubMed

Gu, Zeping; Feng, Jialiang; Han, Wenliang; Wu, Minghong; Fu, Jiamo; Sheng, Guoying

2010-08-01

Solvent extractable organic compounds in PM(2.5) samples collected in Taizhou, a city famous for its electrical and electronic waste (e-waste) recycling industry in Zhejiang province of China, were analyzed to identify the main emission sources based on molecular markers. Two types of plastics which were most frequently contained in the e-wastes, wires/cables and plastic blocks, were burned in the lab and the particles emitted analyzed. The concentrations of PAHs and phthalate esters at the e-waste dismantling area during our sampling periods were about two times of that at the reference urban site, indicating the high pollution level there. The high concentrations of quaterphenyl found at the dismantling area indicated that burning of plastics or polymers was an important emission source of the PAHs in the fine particles. The diagnostic analysis based on the compositions of alkanes, hopanes and other molecular markers showed that engine exhaust, biomass burning and kitchen emissions were also important emission sources at the e-waste dismantling area. Our results suggested that more effort should be paid to control the correlative emission sources such as transportation and kitchen to achieve better air quality at the e-waste dismantling area besides regulating the recycling activities. Copyright 2010 Elsevier Ltd. All rights reserved.

Zero-valent iron/iron oxide-oxyhydroxide/graphene as a magnetic sorbent for the enrichment of polychlorinated biphenyls, polyaromatic hydrocarbons and phthalates prior to gas chromatography-mass spectrometry.

PubMed

Karamani, Anna A; Douvalis, Alexios P; Stalikas, Constantine D

2013-01-04

A composite magnetic material consisting of zero-valent iron, iron oxide-oxyhydroxide and graphene was synthesized and used successfully as a sorbent for the micro solid-phase extraction of PAHs, PCBs and phthalic acid esters. The components endow the composite with multiple characteristics such as adsorption capability and facile removal due to its magnetic properties. Due to the π-π electrostatic stacking property of graphene, the high specific surface area and the adsorption capability of both components, the resulting black flaky Fe(0)/iron oxide-oxyhydroxide/graphene composite showed high extraction efficiency for the target analytes from water samples. Compared with the neat graphene, the composite material has improved properties in terms of microextraction capabilities as both the hydrophobic graphene and zero-valent iron participate in the adsorption of the hydrophobic molecules. The precision from the extraction of all three groups of compounds was lower than 7% and the recoveries were from 90 to 93% from a spiked lake water sample. The high recoveries in relation to the low final volume of the desorption solvent ensure high preconcentration efficiency and a promising sorbent for analytical applications. Copyright © 2012 Elsevier B.V. All rights reserved.

Aminomethylphosphonic acid and methoxyacetic acid induce apoptosis in prostate cancer cells.

PubMed

Parajuli, Keshab R; Zhang, Qiuyang; Liu, Sen; You, Zongbing

2015-05-22

Aminomethylphosphonic acid (AMPA) and its parent compound herbicide glyphosate are analogs to glycine, which have been reported to inhibit proliferation and promote apoptosis of cancer cells, but not normal cells. Methoxyacetic acid (MAA) is the active metabolite of ester phthalates widely used in industry as gelling, viscosity and stabilizer; its exposure is associated with developmental and reproductive toxicities in both rodents and humans. MAA has been reported to suppress prostate cancer cell growth by inducing growth arrest and apoptosis. However, it is unknown whether AMPA and MAA can inhibit cancer cell growth. In this study, we found that AMPA and MAA inhibited cell growth in prostate cancer cell lines (LNCaP, C4-2B, PC-3 and DU-145) through induction of apoptosis and cell cycle arrest at the G1 phase. Importantly, the AMPA-induced apoptosis was potentiated with the addition of MAA, which was due to downregulation of the anti-apoptotic gene baculoviral inhibitor of apoptosis protein repeat containing 2 (BIRC2), leading to activation of caspases 7 and 3. These results demonstrate that the combination of AMPA and MAA can promote the apoptosis of prostate cancer cells, suggesting that they can be used as potential therapeutic drugs in the treatment of prostate cancer.

Estimation of hydrolysis rate constants for carbamates ...

EPA Pesticide Factsheets

Cheminformatics based tools, such as the Chemical Transformation Simulator under development in EPA’s Office of Research and Development, are being increasingly used to evaluate chemicals for their potential to degrade in the environment or be transformed through metabolism. Hydrolysis represents a major environmental degradation pathway; unfortunately, only a small fraction of hydrolysis rates for about 85,000 chemicals on the Toxic Substances Control Act (TSCA) inventory are in public domain, making it critical to develop in silico approaches to estimate hydrolysis rate constants. In this presentation, we compare three complementary approaches to estimate hydrolysis rates for carbamates, an important chemical class widely used in agriculture as pesticides, herbicides and fungicides. Fragment-based Quantitative Structure Activity Relationships (QSARs) using Hammett-Taft sigma constants are widely published and implemented for relatively simple functional groups such as carboxylic acid esters, phthalate esters, and organophosphate esters, and we extend these to carbamates. We also develop a pKa based model and a quantitative structure property relationship (QSPR) model, and evaluate them against measured rate constants using R square and root mean square (RMS) error. Our work shows that for our relatively small sample size of carbamates, a Hammett-Taft based fragment model performs best, followed by a pKa and a QSPR model. This presentation compares three comp

Predicting Residential Exposure to Phthalate Plasticizer Emitted from Vinyl Flooring: Sensitivity, Uncertainty, and Implications for Biomonitoring

PubMed Central

Xu, Ying; Cohen Hubal, Elaine A.; Little, John C.

2010-01-01

Background Because of the ubiquitous nature of phthalates in the environment and the potential for adverse human health effects, an urgent need exists to identify the most important sources and pathways of exposure. Objectives Using emissions of di(2-ethylhexyl) phthalate (DEHP) from vinyl flooring (VF) as an illustrative example, we describe a fundamental approach that can be used to identify the important sources and pathways of exposure associated with phthalates in indoor material. Methods We used a three-compartment model to estimate the emission rate of DEHP from VF and the evolving exposures via inhalation, dermal absorption, and oral ingestion of dust in a realistic indoor setting. Results A sensitivity analysis indicates that the VF source characteristics (surface area and material-phase concentration of DEHP), as well as the external mass-transfer coefficient and ventilation rate, are important variables that influence the steady-state DEHP concentration and the resulting exposure. In addition, DEHP is sorbed by interior surfaces, and the associated surface area and surface/air partition coefficients strongly influence the time to steady state. The roughly 40-fold range in predicted exposure reveals the inherent difficulty in using biomonitoring to identify specific sources of exposure to phthalates in the general population. Conclusions The relatively simple dependence on source and chemical-specific transport parameters suggests that the mechanistic modeling approach could be extended to predict exposures arising from other sources of phthalates as well as additional sources of other semivolatile organic compounds (SVOCs) such as biocides and flame retardants. This modeling approach could also provide a relatively inexpensive way to quantify exposure to many of the SVOCs used in indoor materials and consumer products. PMID:20123613

Predicting residential exposure to phthalate plasticizer emitted from vinyl flooring: sensitivity, uncertainty, and implications for biomonitoring.

PubMed

Xu, Ying; Cohen Hubal, Elaine A; Little, John C

2010-02-01

Because of the ubiquitous nature of phthalates in the environment and the potential for adverse human health effects, an urgent need exists to identify the most important sources and pathways of exposure. Using emissions of di(2-ethylhexyl) phthalate (DEHP) from vinyl flooring (VF) as an illustrative example, we describe a fundamental approach that can be used to identify the important sources and pathways of exposure associated with phthalates in indoor material. We used a three-compartment model to estimate the emission rate of DEHP from VF and the evolving exposures via inhalation, dermal absorption, and oral ingestion of dust in a realistic indoor setting. A sensitivity analysis indicates that the VF source characteristics (surface area and material-phase concentration of DEHP), as well as the external mass-transfer coefficient and ventilation rate, are important variables that influence the steady-state DEHP concentration and the resulting exposure. In addition, DEHP is sorbed by interior surfaces, and the associated surface area and surface/air partition coefficients strongly influence the time to steady state. The roughly 40-fold range in predicted exposure reveals the inherent difficulty in using biomonitoring to identify specific sources of exposure to phthalates in the general population. The relatively simple dependence on source and chemical-specific transport parameters suggests that the mechanistic modeling approach could be extended to predict exposures arising from other sources of phthalates as well as additional sources of other semivolatile organic compounds (SVOCs) such as biocides and flame retardants. This modeling approach could also provide a relatively inexpensive way to quantify exposure to many of the SVOCs used in indoor materials and consumer products.