Water-Compatible Polymer Concrete Materials for use in Rapid Repair Systems for Airport Runways

DTIC Science & Technology

1981-03-01

resin systems, resorcinol phenol- formaldehyde (RPF), urea - formaldehyde (UF), melamine - formaldehyde (MF), and furfuryl alcohol (FA), were selected for...type polymer systems. Phenol- formaldehyde (PF), melamine - formaldehyde (MF), urea -formalde- hyde (UF), and furfuryl alcohol (FA) monomers contain OH and...1-1.5) (1-2) Urea - formaldehyde NH2 CONH2 - HCHO Liquid 7150 (1.0) (1.5-2.5) Melamine - formaldehyde NH2 C:NC(NH2 ):NC(N’H2

Foamable compositions and formations treatment

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

Clampitt, R.L.

1981-11-17

Thermally stable foamable gelled compositions are disclosed suitable for postprimary oil recovery e.g., steam- or gas-foamed systems comprising water, a surfactant, a polymeric viscosifier, an aldehyde component, and at least one phenolic component such as resorcinol, catechol, and the like, as well as selected oxidized phenolic materials such as 1,4-benzoquinone of natural or synthetic origin and natural and modified tannins. The gel compositions can additionally contain gel stabilizers such as sulfomethylated quebracho (Smq) and chemical buffering agents such as sodium bicarbonate.

Enzymic glucosylation of phenols

PubMed Central

Hopkinson, Shirley M.; Pridham, J. B.

1967-01-01

1. A transglucosylase fraction has been obtained from the mycelium of Aspergillus niger. 2. The preparation will transfer α-d-glucopyranosyl residues from maltose and other α-d-glucopyranosides to phenolic and alcoholic hydroxyl groups and to carboxylic acid groups. 3. α-Isomaltosides and α-maltosides are formed when resorcinol and catechol are used as acceptors. 4. pH precipitation and DEAE-cellulose chromatography were used to resolve the activity into two fractions. The properties, in particular polyol inhibition, of one of these fractions have been examined in detail. PMID:5584008

Reaction of bromine and chlorine with phenolic compounds and natural organic matter extracts--Electrophilic aromatic substitution and oxidation.

PubMed

Criquet, Justine; Rodriguez, Eva M; Allard, Sebastien; Wellauer, Sven; Salhi, Elisabeth; Joll, Cynthia A; von Gunten, Urs

2015-11-15

Phenolic compounds are known structural moieties of natural organic matter (NOM), and their reactivity is a key parameter for understanding the reactivity of NOM and the disinfection by-product formation during oxidative water treatment. In this study, species-specific and/or apparent second order rate constants and mechanisms for the reactions of bromine and chlorine have been determined for various phenolic compounds (phenol, resorcinol, catechol, hydroquinone, phloroglucinol, bisphenol A, p-hydroxybenzoic acid, gallic acid, hesperetin and tannic acid) and flavone. The reactivity of bromine with phenolic compounds is very high, with apparent second order rate constants at pH 7 in the range of 10(4) to 10(7) M(-1) s(-1). The highest value was recorded for the reaction between HOBr and the fully deprotonated resorcinol (k = 2.1 × 10(9) M(-1) s(-1)). The reactivity of phenolic compounds is enhanced by the activating character of the phenolic substituents, e.g. further hydroxyl groups. With the data set from this study, the ratio between the species-specific rate constants for the reactions of chlorine versus bromine with phenolic compounds was confirmed to be about 3000. Phenolic compounds react with bromine or chlorine either by oxidation (electron transfer, ET) or electrophilic aromatic substitution (EAS) processes. The dominant process mainly depends on the relative position of the hydroxyl substituents and the possibility of quinone formation. While phenol, p-hydroxybenzoic acid and bisphenol A undergo EAS, hydroquinone, catechol, gallic acid and tannic acid, with hydroxyl substituents in ortho or para positions, react with bromine by ET leading to quantitative formation of the corresponding quinones. Some compounds (e.g. phloroglucinol) show both partial oxidation and partial electrophilic aromatic substitution and the ratio observed for the pathways depends on the pH. For the reaction of six NOM extracts with bromine, electrophilic aromatic substitution accounted for only 20% of the reaction, and for one NOM extract (Pony Lake fulvic acid) it accounted for <10%. This shows that for natural organic matter samples, oxidation (ET) is far more important than bromine incorporation (EAS). Copyright © 2015 Elsevier Ltd. All rights reserved.

Wet air oxidation of resorcinol as a model treatment for refractory organics in wastewaters from the wood processing industry.

PubMed

Weber, Bernd; Chavez, Alma; Morales-Mejia, Julio; Eichenauer, Sabrina; Stadlbauer, Ernst A; Almanza, Rafael

2015-09-15

Wastewater treatment systems are important tools to enhance sustainability in terms of reducing environmental impact and complying with sanitary requirements. This work addresses the wet air oxidation (WAO) process for pre-treatment of phenolic wastewater effluents. The aim was to increase biodegradability prior to a subsequent anaerobic stage. In WAO laboratory experiments using a micro-autoclave, the model compound resorcinol was degraded under different oxygen availability regims within the temperature range 150 °C-270 °C. The activation energy was determined to be 51.5 kJ/mol. Analysis of the products revealed that after 3 h of reaction at 230 °C, 97.5% degradation of resorcinol was achieved. At 250 °C and the same reaction time complete removal of resorcinol was observed. In this case the total organic carbon content was reduced down to 29%, from 118.0 mg/L down to 34.4 mg/L. Under these process conditions, the pollutant was only partially mineralized and the ratio of the biological oxygen demand relative to the chemical oxygen demand, which is 0.07 for resorcinol, was increased to a value exceeding 0.5. The main by-product acetic acid, which is a preferred compound for methanogenic bacteria, was found to account for 33% of the total organic carbon. Copyright © 2015 Elsevier Ltd. All rights reserved.

Gluability of out-of-service utility poles

Treesearch

Han Roliadi; Chung Y. Hse; Elvin T. Choong; Todd F. Shupe

2000-01-01

This investigation determined the gluability of weathered, out-of-service southern yellow pine (SYP) (Pinus spp.) utility poles. Three types of adhesives were used: resorcinol-phenol formaldehyde (RPF), polyvinyl acetate (PVA), and casein. The poles consisted of two service duration groups: 5 and 25 years. Longer weathering caused greater reduction in creosote content...

Adhesives for bonding wood to metal

Treesearch

H. W. Eickner; R. F. Blomquist

1964-01-01

During recent years considerable research and development work have been done on high-strength, durable adhesives for use in bonding metals. Much of this is also applicable for gluing wood to metal. The woodworking adhesives, such as animal, vegetable, casein, urea resin, phenol resin, and resorcinol resin, have not been found entirely suitable for this purpose. They...

Rocket and Missile Container Engineering Guide

DTIC Science & Technology

1982-01-01

impregnated with urea - formaldehyde and melamine - formaldehyde resins , found that a high degree of fungous resistance was imparted to the cotton...34 Phenol-aniline- formaldehyde Resorcinol- formaldehyde Urea - formaldehydes Urea -formaldehydeh Protein- formaldehydes Zein- formaldehyde ("Vicara") Casein...Practically, any cush- ioning material can be made resistant to fungi. The treatment usually involves impregnation

Phenolic profile and fermentation patterns of different commercial gluten-free pasta during in vitro large intestine fermentation.

PubMed

Rocchetti, Gabriele; Lucini, Luigi; Chiodelli, Giulia; Giuberti, Gianluca; Gallo, Antonio; Masoero, Francesco; Trevisan, Marco

2017-07-01

The fate of phenolic compounds, along with short-chain fatty acids (SCFAs) production kinetics, was evaluated on six different commercial gluten-free (GF) pasta samples varying in ingredient compositions, focussing on the in vitro faecal fermentation after the gastrointestinal digestion. A general reduction of both total phenolics and reducing power was observed in all samples, together with a substantial change in phenolic profile over 24h of faecal fermentation, with differences among GF pasta samples. Flavonoids, hydroxycinnamics and lignans degraded over time, with a concurrent increase in low-molecular-weight phenolic acids (hydroxybenzoic acids), alkylphenols, hydroxybenzoketones and tyrosols. Interestingly, discriminant analysis also identified several alkyl derivatives of resorcinol as markers of the changes in phenolic profile during in vitro fermentation. Furthermore, degradation pathways of phenolics by intestinal microbiota have been proposed. Considering the total SCFAs and butyrate production during the in vitro fermentation, different fermentation kinetics were observed among GF pasta post-hydrolysis residues. Copyright © 2017 Elsevier Ltd. All rights reserved.

Condensed tannin-sulfonate derivatives in cold-setting wood-laminating adhesives

Treesearch

Roland E. Kreibich; Richard W. Hemingway

1987-01-01

Extraction of southern pine bark with 4.0 percent sodium sulfite and 0.4-percent sodium carbonate(based on ovendry bark weight) gives epicatechin-(4β)-sulfonate and oligomeric procyanidin-4-sulfonatee that show great promise to replace about 50 percent of the phenol-resorcinol-formaldehyde resin in coldsetting wood-laminating adhesives. Bonds in Douglas-fir...

Condensed tannins: Desulfonation of hydrox-benzylsufonic acids related to proanthocyanidin derivatives.

Treesearch

Gerald W. McGraw; Peter E. Laks; Richard W. Hemingway

1988-01-01

Studies on the desulfonation of 2,4,6-trihydroxybenzylsufonic acid and sodium epicatechin-(4β)-sulfonate showed that suflonates to α a phloroglucinol ring are good leaving groups at ambient temperature and pH greater than 8.0. In contrast, hydroxybenzylsufonic acids with resorcinol or phenol hydroxl functionality resist desulfonation even at pH 12 and...

Quenching of fluorescence of phenolic compounds and modified humic acids by cadmium ions.

PubMed

Tchaikovskaya, O N; Nechaev, L V; Yudina, N V; Mal'tseva, E V

2016-08-01

The interaction of a number of phenolic compounds, being 'model fragments' of humic acids, with cadmium ions was investigated. The fluorescence quenching method was used to determine the complexation constants of these compounds with cadmium ions. It was established that bonding of phenolic compounds by cadmium ions at рН 7 is weak and reaches a maximum value of 15% for interaction with resorcinol. It was demonstrated that modification of humic acids by the mechanoactivation method increases by three times bonding of cadmium ions, which is caused by strengthening the acid properties of carboxyl and hydroxyl groups at the aromatic ring. Copyright © 2016 John Wiley & Sons, Ltd. Copyright © 2016 John Wiley & Sons, Ltd.

Adhesive bonding of wood treated with ACQ and copper azole preservatives

Treesearch

Linda F. Lorenz; Charles Frihart

2006-01-01

Treated wood has generally been more difficult to bond than untreated wood for a variety of reasons. Alkaline copper quat (ACQ) and copper azole (CA-B), the most prominent substitutes for chromated copper arsenate (CCA), are difficult to bond consistently. Using a phenol-resorcinol- formaldehyde (PRF) adhesive formulated for bonding to CCA-treated wood, we examined the...

Application of honeymoon cold-set adhesive systems for structural end joints in North America

Treesearch

Roland E. Kreibich; Richard W. Hemingway; William T. Nearn

1993-01-01

High quality, structural end joints can be cold-set at mill speed using a two-component honeymoon adhesive system composed of southern pine bark or pecan shell membrane tannin and a modified, commercially available. phenol-resorcinol-formaldehyde resin. Adhesive costs of a fully waterproof glueline are approximately $0.60/lb. of applied adhesive mix compared to $0.80/...

RADIATION DOSIMETER AND DOSIMETRIC METHODS

DOEpatents

Taplin, G.V.

1958-10-28

The determination of ionizing radiation by means of single fluid phase chemical dosimeters of the colorimetric type is presented. A single fluid composition is used consisting of a chlorinated hydrocarbon, an acidimetric dye, a normalizer and water. Suitable chlorinated hydrocarbons are carbon tetrachloride, chloroform, trichloroethylene, trichlorethane, ethylene dichioride and tetracbloroethylene. Suitable acidimetric indicator dyes are phenol red, bromcresol purple, and creosol red. Suitable normallzers are resorcinol, geraniol, meta cresol, alpha -tocopberol, and alpha -naphthol.

Aqueous benzene-diols react with an organic triplet excited state and hydroxyl radical to form secondary organic aerosol.

PubMed

Smith, Jeremy D; Kinney, Haley; Anastasio, Cort

2015-04-21

Chemical processing in atmospheric aqueous phases, such as cloud and fog drops, can play a significant role in the production and evolution of secondary organic aerosol (SOA). In this work we examine aqueous SOA production via the oxidation of benzene-diols (dihydroxy-benzenes) by the triplet excited state of 3,4-dimethoxybenzaldehyde, (3)DMB*, and by hydroxyl radical, ˙OH. Reactions of the three benzene-diols (catechol (CAT), resorcinol (RES) and hydroquinone (HQ)) with (3)DMB* or ˙OH proceed rapidly, with rate constants near diffusion-controlled values. The two oxidants exhibit different behaviors with pH, with rate constants for (3)DMB* increasing as pH decreases from pH 5 to 2, while rate constants with ˙OH decrease in more acidic solutions. Mass yields of SOA were near 100% for all three benzene-diols with both oxidants. We also examined the reactivity of atmospherically relevant mixtures of phenols and benzene-diols in the presence of (3)DMB*. We find that the kinetics of phenol and benzene-diol loss, and the production of SOA mass, in mixtures are generally consistent with rate constants determined in experiments containing a single phenol or benzene-diol. Combining our aqueous kinetic and SOA mass yield data with previously published gas-phase data, we estimate a total SOA production rate from benzene-diol oxidation in a foggy area with significant wood combustion to be nearly 0.6 μg mair(-3) h(-1), with approximately half from the aqueous oxidation of resorcinol and hydroquinone, and half from the gas-phase oxidation of catechol.

The depigmenting effect of natural resorcinol type polyphenols Kuwanon O and Sanggenon T from the roots of morus australis.

PubMed

Hu, Shuting; Zheng, Zongping; Chen, Feng; Wang, Mingfu

2017-01-04

Morus australis, one of the major Morus species growing in East Asia, is rich in phenolic compounds. The extract of M. australis has been used as skin whitening components for a long period. The action mechanisms of its principal constituents are still unclear. This study aims to evaluate the skin lightening effects of phenolic compounds extracted from the root of M. australis in different melanocyte systems and artificial skin models. The depigmenting effect of resorcinol type polyphenols (RTPs) from the root extract of M. australis was evaluated in murine b16 and melan-a cell lines using a combined sulforhodamine B assay. Tyrosinase activity and the expression of melanogenesis proteins were evaluated for the mechanism study. The artificial skin model is used as a replacement of the animal test. Only Kuwanon O and Sanggenon T were found to have significant depigmenting effects in both murine b16 and melan-a cell lines. Their depigmenting mechanisms are slightly different in the two cell systems. In b16 cells, Kuwanon O and Sanggenon T, together with the other two RTPs, induced post-transcriptional degradations of MITF without suppressing its mRNA expression, leading to significant decreases of TRP-1 and TRP-2 production. While in melan-a cells, the levels of tyrosinase families were suppressed via MITF downregulation at both transcription and translation level by RTPs, with Kuwanon O inducing the greatest suppression. Further evaluations in artificial skin model demonstrated the outstanding depigmenting effects of Kuwanon O and Sanggenon T. Kuwanon O and Sanggenon T from M.australis root extract are two potential skin whitening ingredients. To screen resorcinol flavonone derivatives with an isoprenyl group in the Diels-Alder substituent might be an option for the search of potent hypopigmenting agents from plants. Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.

Effect of nitro substituent on electrochemical oxidation of phenols at boron-doped diamond anodes.

PubMed

Jiang, Yi; Zhu, Xiuping; Li, Hongna; Ni, Jinren

2010-02-01

In order to investigate nitro-substitutent's effect on degradation of phenols at boron-doped diamond (BDD) anodes, cyclic voltammetries of three nitrophenol isomers: 2-nitrophenol (2NP), 3-nitrophenol (3NP) and 4-nitrophenol (4NP) were studied, and their bulk electrolysis results were compared with phenol's (Ph) under alkaline condition. The voltammetric study showed nitrophenols could be attacked by hydroxyl radicals and nitro-group was released from the aromatic ring. Results of bulk electrolysis showed degradation of all phenols were fit to a pseudo first-order equation and followed in this order: 2NP>4NP>3NP>Ph. Molecular structures, especially carbon atom charge, significantly influenced the electrochemical oxidation of these isomers. Intermediates were analyzed during the electrolysis process, and were mainly catechol, resorcinol, hydroquinone, and carboxylic acids, such as acetic acid and oxalic acid. A simple degradation pathway was proposed. Moreover, a linear increasing relationship between degradation rates and Hammett constants of the studied phenols was observed, which demonstrated that electrochemical oxidation of these phenols was mainly initiated by electrophilic attack of hydroxyl radicals at BDD anodes. Copyright (c) 2009 Elsevier Ltd. All rights reserved.

Utilization of aromatic compounds by the Penicillium strain Bi 7/2.

PubMed

Hofrichter, M; Scheibner, K

1993-01-01

The Penicillium strain Bi 7/2 utilized phenol, catechol, resorcinol, hydroquinone, pyrogallol, hydroxyhydroquinone, phloroglucinol, m- and p-cresol, orcinol, 4-methylcatechol, 4-methoxyphenol, 4-aminophenol, benzyl alcohol, benzoic acid, 2-, 3- and 4-hydroxybenzoic acid, anthranilic acid, protocatechuic acid and gallic acid as sole sources of carbon and energy. The central metabolites catechol, protocatechuic acid and hydroxyquinone could be determined by HPLC with diode-array detection. Pathways for the degradation of aromatic substances were proposed.

Phenolic Compounds in Particles of Mainstream Waterpipe Smoke

PubMed Central

2013-01-01

Introduction: Waterpipe tobacco smoking has in recent years become a popular international phenomenon, particularly among youth. While it has been shown to deliver significant quantities of several carcinogenic and toxic substances, phenols, an important class of chemical compounds thought to promote DNA mutation and cardiovascular diseases, however, has not been studied. Due to the relatively low temperature characteristic of waterpipe tobacco during smoking (i.e., <450 °C), it was hypothesized that phenolic compounds, which form at approximately 300 °C, will be found in abundance in waterpipe smoke. Methods: In this study, phenolic compounds in the particle phase of waterpipe mainstream smoke were quantified. Waterpipe and cigarette mainstream smoke generated using standard methods were collected on glass fiber pads and analyzed using gas chromatography/mass spectroscopy selected ion current profile chromatogram method for quantification. Results: We found that relative to a single cigarette, a waterpipe delivers at least 3 times greater quantities of the 7 analyzed phenols (phenol, o-cresol, m-cresol, p-cresol, catechol, resorcinol, and hydroquinone). Moreover, phenol derivatives such as methylcatechol, and flavorings such as vanillin, ethyl vanillin, and benzyl alcohol were found in quantities up to 1,000 times greater than the amount measured in the smoke of a single cigarette. Conclusion: The large quantities of phenols and phenol derivatives in waterpipe smoke add to the growing evidence that habitual waterpipe use may increase the risk of cancer and cardiovascular diseases. PMID:23178319

Cavitand-Based Polyphenols as Highly Reactive Organocatalysts for the Coupling of Carbon Dioxide and Oxiranes.

PubMed

Martínez-Rodríguez, Luis; Otalora Garmilla, Javier; Kleij, Arjan W

2016-04-07

A variety of cavitand-based polyphenols was prepared from cheap and accessible aldehyde and resorcinol/pyrogallol reagents to give the respective resorcin[4]- or pyrogallol[4]arenes. The preorganization of the phenolic units allows intra- and intermolecular hydrogen bond (HB) networks that affect both the reactivity and stability of these HB-donor catalysts. Unexpectedly, we found that the resorcin[4]arenes show cooperative catalysis behavior compared to the parent resorcinol in the catalytic coupling of epoxides and CO2 with a significantly higher turnover. At elevated reaction temperatures, the resorcin[4]arene-based catalyst 3 d displays the best catalytic performance with very high turnover numbers and frequencies, combining increased reactivity and stability compared to pyrogallol, and an ample substrate scope. This type of polyphenol structure thus illustrates the importance of a new, highly competitive organocatalyst design to devise sustainable CO2 conversion processes. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Controlled Defects of Zinc Oxide Nanorods for Efficient Visible Light Photocatalytic Degradation of Phenol

PubMed Central

Al-Sabahi, Jamal; Bora, Tanujjal; Al-Abri, Mohammed; Dutta, Joydeep

2016-01-01

Environmental pollution from human and industrial activities has received much attention as it adversely affects human health and bio-diversity. In this work we report efficient visible light photocatalytic degradation of phenol using supported zinc oxide (ZnO) nanorods and explore the role of surface defects in ZnO on the visible light photocatalytic activity. ZnO nanorods were synthesized on glass substrates using a microwave-assisted hydrothermal process, while the surface defect states were controlled by annealing the nanorods at various temperatures and were characterized by photoluminescence and X-ray photoelectron spectroscopy. High performance liquid chromatography (HPLC) was used for the evaluation of phenol photocatalytic degradation. ZnO nanorods with high surface defects exhibited maximum visible light photocatalytic activity, showing 50% degradation of 10 ppm phenol aqueous solution within 2.5 h, with a degradation rate almost four times higher than that of nanorods with lower surface defects. The mineralization process of phenol during degradation was also investigated, and it showed the evolution of different photocatalytic byproducts, such as benzoquinone, catechol, resorcinol and carboxylic acids, at different stages. The results from this study suggest that the presence of surface defects in ZnO nanorods is crucial for its efficient visible light photocatalytic activity, which is otherwise only active in the ultraviolet region. PMID:28773363

Controlled Defects of Zinc Oxide Nanorods for Efficient Visible Light Photocatalytic Degradation of Phenol.

PubMed

Al-Sabahi, Jamal; Bora, Tanujjal; Al-Abri, Mohammed; Dutta, Joydeep

2016-03-28

Environmental pollution from human and industrial activities has received much attention as it adversely affects human health and bio-diversity. In this work we report efficient visible light photocatalytic degradation of phenol using supported zinc oxide (ZnO) nanorods and explore the role of surface defects in ZnO on the visible light photocatalytic activity. ZnO nanorods were synthesized on glass substrates using a microwave-assisted hydrothermal process, while the surface defect states were controlled by annealing the nanorods at various temperatures and were characterized by photoluminescence and X-ray photoelectron spectroscopy. High performance liquid chromatography (HPLC) was used for the evaluation of phenol photocatalytic degradation. ZnO nanorods with high surface defects exhibited maximum visible light photocatalytic activity, showing 50% degradation of 10 ppm phenol aqueous solution within 2.5 h, with a degradation rate almost four times higher than that of nanorods with lower surface defects. The mineralization process of phenol during degradation was also investigated, and it showed the evolution of different photocatalytic byproducts, such as benzoquinone, catechol, resorcinol and carboxylic acids, at different stages. The results from this study suggest that the presence of surface defects in ZnO nanorods is crucial for its efficient visible light photocatalytic activity, which is otherwise only active in the ultraviolet region.

Secondary Organic Aerosol Produced from Aqueous Reactions of Phenols in Fog Drops and Deliquesced Particles

NASA Astrophysics Data System (ADS)

Smith, J.; Anastasio, C.

2014-12-01

The formation and evolution of secondary organic aerosol (SOA) in atmospheric condensed phases (i.e., aqueous SOA) can proceed rapidly, but relatively little is known of the important aqueous SOA precursors or their reaction pathways. In our work we are studying the aqueous SOA formed from reactions of phenols (phenol, guaiacol, and syringol), benzene-diols (catechol, resorcinol, and hydroquinone), and phenolic carbonyls (e.g., vanillin and syringaldehyde). These species are potentially important aqueous SOA precursors because they are released in large quantities from biomass burning, have high Henry's Law constants (KH = 103 -109 M-1 atm-1) and are rapidly oxidized. To evaluate the importance of aqueous reactions of phenols as a source of SOA, we first quantified the kinetics and SOA mass yields for 11 phenols reacting via direct photodegradation, hydroxyl radical (•OH), and with an excited organic triplet state (3C*). In the second step, which is the focus of this work, we use these laboratory results in a simple model of fog chemistry using conditions during a previously reported heavy biomass burning event in Bakersfield, CA. Our calculations indicate that under aqueous aerosol conditions (i.e., a liquid water content of 100 μg m-3) the rate of aqueous SOA production (RSOA(aq)) from phenols is similar to the rate in the gas phase. In contrast, under fog/cloud conditions the aqueous RSOA from phenols is 10 times higher than the rate in the gas phase. In both of these cases aqueous RSOA is dominated by the oxidation of phenols by 3C*, followed by direct photodegradation of phenolic carbonyls, and then •OH oxidation. Our results suggest that aqueous oxidation of phenols is a significant source of SOA during fog events and also during times when deliquesced aerosols are present.

Effect of the pH in the adsorption and in the immersion enthalpy of monohydroxylated phenols from aqueous solutions on activated carbons.

PubMed

Blanco-Martínez, D A; Giraldo, L; Moreno-Piraján, J C

2009-09-30

An activated carbon Carbochem--PS230 was modified by chemical and thermal treatment in flow of H(2) in order to evaluate the influence of the activated carbon chemical surface in the adsorption of the monohydroxylated phenols. The solid-solution interaction was determined by analyzing the adsorption isotherms at 298 K at pH 7, 9 and 11 during 48 h. The adsorption capacity of activated carbons increases when the pH solution decreases. The amount adsorbed increases in the reduced carbon at the maximum adsorption pH and decreases in the oxidized carbon. In the sample of granulated activated carbon, CAG, the monohydroxylated phenols adsorption capacity diminishes in the following order catechol >hydroquinone >resorcinol, at the three pH values. The experimental data are evaluated with Freundlich's and Langmuir's models. The immersion enthalpies are determined and increase with the retained amount, ranging between 21.5 and 45.7 J g(-1). In addition, the immersion enthalpies show more interaction with the reduced activated carbon that has lower total acidity contents.

14N NQR study of hydrogen bonded complexes of 1,4 diazabicyclo [2,2,2] octane (ted) with phenols and thiourea

NASA Astrophysics Data System (ADS)

Murgich, Juan; Magaly, Santana R.; Diaz, Olga E.

The 14N NQR spectra of H bonded complexes of 1,4 diazabicyclo [2,2,2] octane, also known as triethylenediamine (TED), with phenol (1:2), p-chlorophenol (1:2), p-nitrophenol (1:2), hydroquinone (1:1), resorcinol (1:1) and thiourea (1:2) were observed at 77 K. The 14N frequency shifts produced by the H bonds in the TED complexes were approximately two times larger than those found for similar complexes of Hexamethylenetetramine (HMT). Such change was explained by the effect on the remaining N atoms of the increase in the number of -CH 2- groups and the decrease in N atoms in passing from HMT to TED. From the above results it seems that the inductive effect plays an important role in the formation of H bonds in tertiary amines like HMT and TED.

Solid-Phase Spectrophotometric Analysis of 1-Naphthol Using Silica Functionalized with m-Diazophenylarsonic Acid

NASA Astrophysics Data System (ADS)

Zaitseva, Nataliya; Alekseev, Sergei; Zaitsev, Vladimir; Raks, Viktoria

2016-03-01

The m-aminophenylarsonic acid (m-APAA) was immobilized onto the silica gel surface with covalently grafted quaternary ammonium groups via ion exchange. The diazotization of ion-bonded m-APAA resulted in a new solid-phase spectrophotometric reagent for detection of 1-naphtol in environmental water samples. The procedure of solid-phase spectrophotometric analysis is characterized by 20 μg L-1 limit of detection (LOD) of 1-naphtol, up to 2000 concentration factor, and insensitivity to the presence of natural water components as well as to 30-fold excess of phenol, resorcinol, and catechol.

In vitro anti-platelet effects of simple plant-derived phenolic compounds are only found at high, non-physiological concentrations.

PubMed

Ostertag, Luisa M; O'Kennedy, Niamh; Horgan, Graham W; Kroon, Paul A; Duthie, Garry G; de Roos, Baukje

2011-11-01

Bioactive polyphenols from fruits, vegetables, and beverages have anti-platelet effects and may thus affect the development of cardiovascular disease. We screened the effects of 26 low molecular weight phenolic compounds on two in vitro measures of human platelet function. After platelets had been incubated with one of 26 low molecular weight phenolic compounds in vitro, collagen-induced human platelet aggregation and in vitro TRAP-induced P-selectin expression (as marker of platelet activation) were assessed. Incubation of platelet-rich plasma from healthy volunteers with 100 μmol/L hippuric acid, pyrogallol, catechol, or resorcinol significantly inhibited collagen-induced platelet aggregation (all p<0.05; n≥15). Incubation of whole blood with concentrations of 100 μmol/L salicylic acid, p-coumaric acid, caffeic acid, ferulic acid, 4-hydroxyphenylpropionyl glycine, 5-methoxysalicylic acid, and catechol significantly inhibited TRAP-induced surface P-selectin expression (all p<0.05; n=10). Incubation with lower concentrations of phenolics affected neither platelet aggregation nor activation. As concentrations of 100 μmol/L are unlikely to be reached in the circulation, it is doubtful whether consumption of dietary phenolics in nutritionally attainable amounts plays a major role in inhibition of platelet activation and aggregation in humans. Copyright © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Condensed tannin-resorcinol adducts and their use in wood-laminating adhesives: An exploratory study

Treesearch

Richard W. Hemingway; R.E. Kreibich

1984-01-01

The reaction of a tannin extract (containing about 30% carbohydrate) from loblolly pine (Pinus taeda L.) bark (two parts) and resorcinol (one part) at 120°C for 24 h with acetic acid catalyst gave a product containing predominantly oligomeric procyanidin-4-resorcinol adducts (39%), unreacted resorcinol (22%), carbohydrate (20%). the resorcinol adduct...

Exogenous Ochronosis

PubMed Central

Bhattar, Prachi A; Zawar, Vijay P; Godse, Kiran V; Patil, Sharmila P; Nadkarni, Nitin J; Gautam, Manjyot M

2015-01-01

Exogenous ochronosis (EO) is a cutaneous disorder characterized by blue-black pigmentation resulting as a complication of long-term application of skin-lightening creams containing hydroquinone but may also occur due to topical contact with phenol or resorcinol in dark-skinned individuals. It can also occur following the use of systemic antimalarials such as quinine. EO is clinically and histologically similar to its endogenous counterpart viz., alkaptonuria, which, however, exhibits systemic effects and is an inherited disorder. Dermoscopy and in vivo skin reflectance confocal microscopy are noninvasive in vivo diagnostic tools. It is very difficult to treat EO, a cosmetically disfiguring and troubling disorder with disappointing treatment options. PMID:26677264

R6 Hexameric Insulin Complexed with m-Cresol or Rescorcinol

NASA Technical Reports Server (NTRS)

Smith, G. David; Ciszak, Ewa; Magrum, Lucy A.; Rose, M. Franklin (Technical Monitor)

2000-01-01

The structures of three R6 human insulin hexamers have been determined. Crystals of monoclinic m-cresol/insulin, monoclinic resorcinol/insulin, and rhombohedral m-cresol/insulin crystals diffracted to 1.9, 1.9 and 1,78 Angstroms, respectively, and have been refined to residuals of 0.195, 0.179, and 0.200, respectively. In all three structures, a phenolic derivative is found to occupy the phenolic binding site where it forms hydrogen bonds to the carbonyl oxygen of A6 Cys and the nitrogen of A11 Cys. Two additional phenolic derivative binding sites were identified within or between hexamers. The structures of all three hexamers are nearly identical although a large displacement of the N-terminus of one B-chain in both monoclinic structures results from coordination to a sodium ion which is located between symmetry related hexamers. Other minor differences in structure are a consequence of differences in packing in the monoclinic cell as compared to the rhombohedral cell. Based upon the differences in conformation of the B13 Glu side chains in T6, T3R3, and R6 hexamers, the deprotonation of these side chains appears to be associated with the T (right arrow) R conformational transition.

Aerogel and xerogel composites for use as carbon anodes

DOEpatents

Cooper, John F.; Tillotson, Thomas M.; Hrubesh, Lawrence W.

2010-10-12

A method for forming a reinforced rigid anode monolith and fuel and product of such method. The method includes providing a solution of organic aerogel or xerogel precursors including at least one of a phenolic resin, phenol (hydroxybenzene), resorcinol(1,3-dihydroxybenzene), or catechol(1,2-dihydroxybenzene); at least one aldehyde compound selected from the group consisting of formaldehyde, acetaldehyde, and furfuraldehyde; and an alkali carbonate or phosphoric acid catalyst; adding internal reinforcement materials comprising carbon to said precursor solution to form a precursor mixture; gelling said precursor mixture to form a composite gel; drying said composite gel; and pyrolyzing said composite gel to form a wettable aerogel/carbon composite or a wettable xerogel/carbon composite, wherein said composites comprise chars and said internal reinforcement materials, and wherein said composite is suitable for use as an anode with the chars being fuel capable of being combusted in a molten salt electrochemical fuel cell in the range from 500 C to 800 C to produce electrical energy. Additional methods and systems/compositions are also provided.

Solution-state NMR analysis of hydroxymethylated resorcinol cured in the presence of crude milled-wood lignin from Acer saccharum

Treesearch

Daniel J. Yelle

2017-01-01

Resorcinol-formaldehyde adhesives can reinforce stress fractures that appear from wood surface preparation. Researchers have found that applying the resorcinol-formaldehyde prepolymer, hydroxymethylated resorcinol is thought to plasticize lignin components and stabilize stress fractures through reactions with lignin subunits and hemicelluloses in wood. In this study, a...

Condensed tannin-resorcinol adducts in laminating adhesives

Treesearch

Richard W. Hemingway; Roland E. Kreibich

1985-01-01

A condensed tannin-resorcinol adduct made by co-reaction of an extract from southern pine bark with resorcinol at a 2 to 1 weight ratio was used to prepare a laminating resin in which the entire amount of resorcinol normally used was replaced by this adduct. The resin was formulated into a room temperature setting adhesive that meets the basic criteria of product...

Method for making thin carbon foam electrodes

DOEpatents

Pekala, Richard W.; Mayer, Steven T.; Kaschmitter, James L.; Morrison, Robert L.

1999-01-01

A method for fabricating thin, flat carbon electrodes by infiltrating highly porous carbon papers, membranes, felts, metal fibers/powders, or fabrics with an appropriate carbon foam precursor material. The infiltrated carbon paper, for example, is then cured to form a gel-saturated carbon paper, which is subsequently dried and pyrolyzed to form a thin sheet of porous carbon. The material readily stays flat and flexible during curing and pyrolyzing to form thin sheets. Precursor materials include polyacrylonitrile (PAN), polymethylacrylonitrile (PMAN), resorcinol/formaldehyde, catechol/formaldehyde, phenol/formaldehyde, etc., or mixtures thereof. These thin films are ideal for use as high power and energy electrodes in batteries, capacitors, and fuel cells, and are potentially useful for capacitive deionization, filtration and catalysis.

Nonenzymic spectrophotometric determination of potential poison ivy cross-reactors.

PubMed

Quattrone, A J

1977-03-01

I describe an inexpensive, nonenzymic analytical system for prescreening substances that might cross-react as Rhus toxing (e.g., poison ivy, poison oak, and sumac allergens) on human skin. By spectrophotometric assay after incubation with an oxidizing mixture of Cu(II)ammine complex and ammonium persulfate, I could accurately and reproducibly determine o-quinoidal products of several potential synthetic cross-reactors and native poison ivy allergen, and could distinguish these from catecholamines, resorcinol, p-hydroquinone, and a closely related phenol. A good correlation was obtained between this nonenzymic technique and an enzymic assay. This Cu(II)ammine/persulfate oxidative assay, however, is inexpensive and obviates any spectral interference from enzymic proteins.

Reductive transformation of dioxins: An assessment of the contribution of dissolved organic matter to dechlorination reactions

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

Fu, Q.S.; Barkovskii, A.L.; Adriaens, P.

1999-11-01

The susceptibility of dioxins to dissolved organic carbon (DOC)-mediated dechlorination reactions was investigated using 1,2,3,4,6,7,9-heptachlorodibenzo-p-dioxin (HpCDD), Aldrich humic acid (AHA), and polymaleic acid (PMA) as model compounds. The dechlorination yields were on the order of 4--20% which, when normalized to phenolic acidity, was comparable to yields observed in the presence of the humic constituents catechol and resorcinol. Based on the ratio of dechlorination yields as a function of phenolic acidity and electron transfer capacity, differences in electron transfer efficiency to dioxins are likely combined effects of specific interactions with the functional groups and nonspecific hydrophobic interactions. Hexa- and pentaCDD homologuesmore » were dominant in all incubations, and diCDD constituted the final product of dechlorination. The rates of appearance of lesser chlorinated products were similar to those observed in sediment systems and followed thermodynamic considerations as they decreased with a decrease in level of chlorination. Generally, both absolute and phenolic acidity-normalized rate constants for AHA-mediated reactions were up to 2-fold higher than those effected by PMA. These results indicate that the electron shuttling capacity of sediment DOC may significantly affect the fate of dioxins, in part through dechlorination reactions.« less

Environmental and occupational exposure to resorcinol in Finland.

PubMed

Porras, Simo P; Hartonen, Minna; Ylinen, Katriina; Tornaeus, Jarkko; Tuomi, Tapani; Santonen, Tiina

2018-03-27

Resorcinol is a suspected endocrine disruptor that affects thyroid function by inhibiting thyroxin peroxidase. It may also have an impact on iodine uptake. Resorcinol has various uses; for example in the manufacture of rubber products and in wood adhesives, flame retardants, UV stabilizers, and dyes. It is also used in personal care products such as hair colorants, anti-acne preparations, and peels. The aim of this study was to assess both environmental background exposure and occupational exposure to resorcinol in Finland. We investigated occupational exposure in hairdresser work and in the manufacture of tyres, adhesive resins and glue-laminated timber by biomonitoring total resorcinol concentration in urine samples. The biomonitoring results were compared to the urinary levels of occupationally non-exposed volunteers, and to the biomonitoring equivalent (BE), which we estimated on the basis of the EFSA's acceptable daily intake (ADI) value for resorcinol. Almost all the urine samples (99%) of the non-occupationally exposed volunteers contained measurable amounts of resorcinol. The urinary resorcinol data were rather scattered, and the resorcinol concentrations among women (GM 84 μg/l, 95th percentile 2072 μg/l) were clearly higher than the respective concentrations among men (GM 35 μg/l, 95th percentile 587 μg/l). The reason for this difference remains unclear. Although the two highest results exceeded the BE of 4 mg/l calculated on the basis of the EFSA's ADI, the 95th percentile of the occupationally non-exposed volunteers' results remained well below the BE among both males and females. According to the results, hairdressers' exposure to resorcinol was at the same level as that of the reference population of occupationally non-exposed volunteers. All hairdresser's values remained below the BE for resorcinol. The urinary resorcinol levels of the industrial workers were also at the same level as those of the reference population. We observed slight increases in the post-shift and evening samples of those working in the manufacture of tyres and adhesive resins. The results of some workers in the tyre manufacturing company exceeded the 95th percentile of non-occupationally exposed males, which was used as a biological guidance value for occupational exposure. Moreover, in this case exposure was below the health-based biomonitoring equivalents. All the air samples collected in the companies contained very low resorcinol concentrations. It should be noted that the sample sizes for the male controls and industrial groups were small. Copyright © 2018. Published by Elsevier B.V.

A Surfactant-Free Synthesis Technique of Coral-Like Zno Hierarchical Structures for Photocatalytic Degradation of Resorcinol under UV Irradiation

NASA Astrophysics Data System (ADS)

Sin, Jin-Chung; Lam, Sze-Mun; Chin, Ying-Hui

2018-01-01

Hierarchical coral-like ZnO structures were successfully prepared by a surfactant-free wet chemical method. Various characterization tests were carried out to analyze the as-prepared ZnO samples. The coral-like ZnO was used to degrade resorcinol at three different solution pH values (pH 5.0, pH 8.0 and pH 11.0). It was observed that the resorcinol adsorption onto the ZnO was strongly dependent on the electrical charge properties of both photocatalyst and resorcinol. Photocatalytic degradation of resorcinol reached the highest at pH 11.0 due to high concentration of hydroxyl ions for hydroxyl radicals generation.

Characterization of pure and composite resorcinol formaldehyde aerogels doped with silver

NASA Astrophysics Data System (ADS)

Attia, S. M.; Abdelfatah, M. S.; Mossad, M. M.

2017-07-01

A series of Resorcinol Formaldehyde (RF) aerogels composites with nanoparticles of sliver were prepared by the sol-gel method at different concentrations doped silver. FTIR spectra of pure and composite RF aerogels show six absorption bands attributed to -OH groups bonded to the benzene ring, stretching of -CH2- bonds and aromatic ring stretching. FTIR results ensured that sliver particles do not interact with aerogel network. UV-visible spectrum of pure silver show an absorbance peak at 420 nm attributed to the surface plasmon excitation of sliver Nano spheres. UV-visible spectral of pure and composite RF aerogels shows a steep decrease of absorption with wavelength after 500 nm, making sample’s color reddish brown. TEM and SEM images of pure and composite RF aerogels revealed that the textural arrangement of RF aerogels can be described as densely packed small nodules.

Oxidation and reduction in irradiated binary crystals of resorcinol and progesterone

NASA Astrophysics Data System (ADS)

Box, Harold C.; Budzinski, Edwin E.

1985-12-01

The binary single crystals of resorcinol and progesterone were x-irradiated at 4.2 K. The semiquinone of resorcinol was generated by radiation induced oxidation. The oxidation and reduction products were identified from ESR and ENDOR measurements. (AIP)

Durability of one-part polyurethane bonds to wood improved by HMR coupling agent

Treesearch

Charles B. Vick; E. Arnold Okkonen

2000-01-01

In a previous study on the strength and durability of a new class of wood adhesives called one-part polyurethanes, four commercial one-part polyurethanes, along with a resorcinol-formaldehyde adhesive representing a standard of performance, were compared in bonds to yellow birch and Douglas-fir in a series of industry-accepted tests (7). The polyurethanes all performed...

Method for making thin carbon foam electrodes

DOEpatents

Pekala, R.W.; Mayer, S.T.; Kaschmitter, J.L.; Morrison, R.L.

1999-08-03

A method for fabricating thin, flat carbon electrodes by infiltrating highly porous carbon papers, membranes, felts, metal fibers/powders, or fabrics with an appropriate carbon foam precursor material is disclosed. The infiltrated carbon paper, for example, is then cured to form a gel-saturated carbon paper, which is subsequently dried and pyrolyzed to form a thin sheet of porous carbon. The material readily stays flat and flexible during curing and pyrolyzing to form thin sheets. Precursor materials include polyacrylonitrile (PAN), polymethylacrylonitrile (PMAN), resorcinol/formaldehyde, catechol/formaldehyde, phenol/formaldehyde, etc., or mixtures thereof. These thin films are ideal for use as high power and energy electrodes in batteries, capacitors, and fuel cells, and are potentially useful for capacitive deionization, filtration and catalysis.

Expression and characteristics of manganese peroxidase from Ganoderma lucidum in Pichia pastoris and its application in the degradation of four dyes and phenol.

PubMed

Xu, Hui; Guo, Meng-Yuan; Gao, Yan-Hua; Bai, Xiao-Hui; Zhou, Xuan-Wei

2017-02-23

Manganese peroxidase (MnP) of white rot basidiomycetes, an extracellular heme enzyme, is part of a peroxidase superfamily that is capable of degrading the different phenolic compounds. Ganoderma, a white rot basidiomycete widely distributed worldwide, could secrete lignin-modifying enzymes (LME), including laccase (Lac), lignin peroxidases (LiP) and MnP. After the selection of a G. lucidum strain from five Ganoderma strains, the 1092 bp full-length cDNA of the MnP gene, designated as G. lucidum MnP (GluMnP1), was cloned from the selected strain. We subsequently constructed an eukaryotic expression vector, pAO815:: GlMnP, and transferred it into Pichia pastoris SMD116. Recombinant GluMnP1 (rGluMnP1) was with a yield of 126 mg/L and a molecular weight of approximately 37.72 kDa and a specific enzyme activity of 524.61 U/L. The rGluMnP1 could be capable of the decolorization of four types of dyes and the degradation of phenol. Phenol and its principal degradation products including hydroquinone, pyrocatechol, resorcinol, benzoquinone, were detected successfully in the experiments. The rGluMnP1 could be effectively expressed in Pichia pastoris and with a higher oxidation activity. We infer that, in the initial stages of the reaction, the catechol-mediated cycle should be the principal route of enzymatic degradation of phenol and its oxidation products. This study highlights the potential industrial applications associated with the production of MnP by genetic engineering methods, and the application of industrial wastewater treatment.

Changes of turbidity during the phenol oxidation by photo-Fenton treatment.

PubMed

Villota, Natalia; Camarero, Luis M; Lomas, Jose M; Perez, Jonatan

2014-11-01

Turbidity presented by phenol solutions oxidized with Fenton reagent shows the tendency of a first order intermediate kinetics. Thus, turbidity can be considered a representative parameter of the presence of intermediate oxidation species, which are generated along the decomposition of toxic and reluctant contaminants, such as phenol. Moreover, that parameter presents a linear dependence with the catalyst dosage, but is also determined by the initial contaminant load. When analyzing the oxidation mechanism of phenol, it is found that the maximum turbidity occurs when the treatment is carried out at oxidant to phenol molar ratios R = 4.0. These oxidation conditions correspond to the presence of a reaction mixture mainly composed of dihydroxylated rings, precursors of the muconic acid formation. The oxidation via "para" comprises the formation reactions of charge transfer complexes (quinhydrone), between the para-dihydroxylated intermediates (hydroquinone) and the para-substituted quinones (p-benzoquinone), which are quite unstable and reactive species, quickly decomposed into hydroxyhydroquinones. Working with oxidant ratios up to R = 6.0, the maximum observed value of turbidity in the oxidized solutions is kept almost constant. It is found that, in these conditions, the pyrogallol formation is maximal, what is generated through the degradation of ortho-species (catechol and ortho-benzoquinone) and meta-substituted (resorcinol). Operating with ratios over R = 6.0, these intermediates are decomposed into biodegradable acids, generating lower turbidity in the solution. Then, the residual turbidity is a function of the molar ratio of the ferrous ions vs. moles of oxidant utilized in the essays, that lets to estimate the stoichiometric dosage of catalyst as 20 mg/L at pH = 3.0, whereas operating in stoichiometric conditions, R = 14.0, the residual turbidity of water results almost null.

Resorcinol-formaldehyde reactions in dilute solution observed by carbon-13 NMR spectroscopy

Treesearch

Alfred W. Christiansen

2000-01-01

A recently discovered coupling agent, hydroxymethylated resorcinol (HMR), based on resorcinol-formaldehyde, can greatly enhance wood-to-epoxy resin bond durability in exterior applications. However, for HMR to be most effective, it needs to be prepared a few hours before it is applied to the...

Hair Dyes Resorcinol and Lawsone Reduce Production of Melanin in Melanoma Cells by Tyrosinase Activity Inhibition and Decreasing Tyrosinase and Microphthalmia-Associated Transcription Factor (MITF) Expression

PubMed Central

Lee, Shu-Mei; Chen, Yi-Shyan; Lin, Chih-Chien; Chen, Kuan-Hung

2015-01-01

Hair coloring products are one of the most important cosmetics for modern people; there are three major types of hair dyes, including the temporary, semi-permanent and permanent hair dyes. The selected hair dyes (such as ammonium persulfate, sodium persulfate, resorcinol and lawsone) are the important components for hair coloring products. Therefore, we analyzed the effects of these compounds on melanogenesis in B16-F10 melanoma cells. The results proved that hair dyes resorcinol and lawsone can reduce the production of melanin. The results also confirmed that resorcinol and lawsone inhibit mushroom and cellular tyrosinase activities in vitro. Resorcinol and lawsone can also downregulate the protein levels of tyrosinase and microphthalmia-associated transcription factor (MITF) in B16-F10 cells. Thus, we suggest that frequent use of hair dyes may have the risk of reducing natural melanin production in hair follicles. Moreover, resorcinol and lawsone may also be used as hypopigmenting agents to food, agricultural and cosmetic industry in the future. PMID:25584612

Degradation of phenolic compounds with hydrogen peroxide catalyzed by enzyme from Serratia marcescens AB 90027.

PubMed

Yao, Ri-Sheng; Sun, Min; Wang, Chun-Ling; Deng, Sheng-Song

2006-09-01

In this paper, the degradation of phenolic compounds using hydrogen peroxide as oxidizer and the enzyme extract from Serratia marcescens AB 90027 as catalyst was reported. With such an enzyme/H2O2 combination treatment, a high chemical oxygen demand (COD) removal efficiency was achieved, e.g., degradation of hydroquinone exceeded 96%. From UV-visible and IR spectra, the degradation mechanisms were judged as a process of phenyl ring cleavage. HPLC analysis shows that in the degradation p-benzoquinone, maleic acid and oxalic acid were formed as intermediates and that they were ultimately converted to CO2 and H2O. With the enzyme/H2O2 treatment, vanillin, hydroquinone, catechol, o-aminophenol, p-aminophenol, phloroglucinol and p-hydroxybenzaldehyde were readily degraded, whereas the degradation of phenol, salicylic acid, resorcinol, p-cholorophenol and p-nitrophenol were limited. Their degradability was closely related to the properties and positions of their side chain groups. Electron-donating groups, such as -OH, -NH2 and -OCH3 enhanced the degradation, whereas electron-withdrawing groups, such as -NO2, -Cl and -COOH, had a negative effect on the degradation of these compounds in the presence of enzyme/H2O2. Compounds with -OH at ortho and para positions were more readily degraded than those with -OH at meta positions.

Electrochemical Oxidation of Resorcinol in Aqueous Medium Using Boron-Doped Diamond Anode: Reaction Kinetics and Process Optimization with Response Surface Methodology

PubMed Central

Körbahti, Bahadır K.; Demirbüken, Pelin

2017-01-01

Electrochemical oxidation of resorcinol in aqueous medium using boron-doped diamond anode (BDD) was investigated in a batch electrochemical reactor in the presence of Na2SO4 supporting electrolyte. The effect of process parameters such as resorcinol concentration (100–500 g/L), current density (2–10 mA/cm2), Na2SO4 concentration (0–20 g/L), and reaction temperature (25–45°C) was analyzed on electrochemical oxidation using response surface methodology (RSM). The optimum operating conditions were determined as 300 mg/L resorcinol concentration, 8 mA/cm2 current density, 12 g/L Na2SO4 concentration, and 34°C reaction temperature. One hundred percent of resorcinol removal and 89% COD removal were obtained in 120 min reaction time at response surface optimized conditions. These results confirmed that the electrochemical mineralization of resorcinol was successfully accomplished using BDD anode depending on the process conditions, however the formation of intermediates and by-products were further oxidized at much lower rate. The reaction kinetics were evaluated at optimum conditions and the reaction order of electrochemical oxidation of resorcinol in aqueous medium using BDD anode was determined as 1 based on COD concentration with the activation energy of 5.32 kJ/mol that was supported a diffusion-controlled reaction. PMID:29082225

Studies on the synthesis, spectra, catalytic and antibacterial activities of binuclear ruthenium(II) complexes.

PubMed

Krishnamoorthy, P; Sathyadevi, P; Deepa, K; Dharmaraj, N

2010-09-15

A new series of stable binuclear ruthenium(II) carbonyl complexes of the general formula [{RuX(CO)(EPh(3))(2)}(2)L] (where X=H or Cl; E=P or As and L=dibasic tetradentate diacetyl resorcinol (H(2)-DAR)) have been synthesised by reacting ruthenium(II) starting complexes [RuHX(CO)(EPh(3))(3)] (where X=H or Cl; E=P or As) and 4,6-diacetylresorcinol (H(2)-DAR) ligand in benzene medium. The structure of the new binuclear ruthenium(II) carbonyl complexes was established using elemental analysis, spectra (FT-IR, UV-vis and (1)H NMR), electrochemical and thermal studies. In these reactions, the 4,6-diacetylresorcinol (H(2)-DAR) ligand behaves as a binegative tetradentate chelating ligand coordinating through O,O atoms of both the carbonyl and phenolic C-O groups by replacing a molecule of PPh(3)/AsPh(3) and a hydride ion from the starting complexes. Further, all these complexes were also employed as new catalysts for the oxidation of primary and secondary alcohols in the presence of N-methylmorpholine-N-oxide (NMO) as a more viable co-oxidant. The free ligand and their metal complexes have also been screened for their antibacterial activity against the growth of gram +ve and gram -ve bacterial cultures. Copyright 2010 Elsevier B.V. All rights reserved.

Effect of substituted hydroxyl groups in the changes of solution turbidity in the oxidation of aromatic contaminants.

PubMed

Villota, N; Jm, Lomas; Lm, Camarero

2017-01-01

This paper deals with the changes of turbidity that are generated in aqueous solutions of phenol when they are oxidized by using different Fenton technologies. Results revealed that if the Fenton reaction was promoted with UV light, the turbidity that was generated in the water doubled. Alternatively, the use of ultrasonic waves produced an increase in turbidity which initially proceeded slowly, reaching intensities eight times higher than in the conventional Fenton treatment. As well, the turbidity showed a high dependence on pH. It is therefore essential to control acidity throughout the reaction. The maximum turbidity was generated when operating at pH = 2.0, and it slowly decreased with increasing to a value of pH = 3.0, at which the turbidity was the lowest. This result was a consequence of the presence of ferric ions in solution. At pH values greater than 3.5, the turbidity increased almost linearly until at pH = 5.0 reached its maximum intensity. In this range, ferrous ions may generate an additional contribution of radicals that promote the degradation of the phenol species that produce turbidity. Turbidity was enhanced at ratios R = 4.0 mol H 2 O 2 /mol C 6 H 6 O. This value corresponds to the stoichiometric ratio that leads to the production of turbidity-precursor species. Therefore, muconic acid would be a species that generate high turbidity in solution according to its isomerism. Also, the results revealed that the turbidity is not a parameter to which species contribute additively since interactions may occur among species that would enhance their individual contributions to it. Analyzing the oxidation of phenol degradation intermediates, the results showed that meta-substituted compounds (resorcinol) generate high turbidity in the wastewater. The presence of polar molecules, such as muconic acid, would provide the structural features that are necessary for resorcinol to act as a clip between two carboxylic groups, thus establishing directional hydrogen bonds that would generate an adduct in the 2:2 ratio. In addition, some similarity is observed between the turbidity and the presence of dihydroxybenzoquinone. This molecule has a structure that could establish hydrogen bond links with the carboxylic groups in 1:2 ratio. Such supramolecular structures would possess high molecular weight and robustness that would hinder the passage of light through the water, generating high turbidity.

Melamine-bridged alkyl resorcinol modified urea - formaldehyde resin for bonding hardwood plywood

Treesearch

Chung-Yun Hse; Mitsuo Higuchi

2010-01-01

A powdery product was obtained by the reaction of methylolated melamine with alkyl resorcinols to form melamine-bridged alkyl resorcinols (MARs). The effects of the addition of this powder on the bonding strength and formaldehyde emission of urea–formaldehyde (UF) resins were investigated. Three types of UF resins with a formaldehyde/urea molar ratio of 1.3 synthesized...

Reversed phase liquid chromatography with UV absorbance and flame ionization detection using a water mobile phase and a cyano propyl stationary phase Analysis of alcohols and chlorinated hydrocarbons.

PubMed

Quigley, W W; Ecker, S T; Vahey, P G; Synovec, R E

1999-10-01

The development of liquid chromatography with a commercially available cyano propyl stationary phase and a 100% water mobile phase is reported. Separations were performed at ambient temperature, simplifying instrumental requirements. Excellent separation efficiency using a water mobile phase was achieved, for example N=18 800, or 75 200 m(-1), was obtained for resorcinol, at a retention factor of k'=4.88 (retention time of 9.55 min at 1 ml min(-1) for a 25 cmx4.6 mm i.d. column, packed with 5 mum diameter particles with the cyano propyl stationary phase). A separation via reversed phase liquid chromatography (RP-LC) with a 100% water mobile phase of six phenols and related compounds was compared to a separation of the same compounds by traditional RP-LC, using octadecylsilane (ODS), i.e. C18, bound to silica and an aqueous mobile phase modified with acetonitrile. Nearly identical analysis time was achieved for the separation of six phenols and related compounds using the cyano propyl stationary phase with a 100% water mobile phase, as compared to traditional RP-LC requiring a relatively large fraction of organic solvent modifier in the mobile phase (25% acetonitrile:75% water). Additional understanding of the retention mechanism with the 100% water mobile phase was obtained by relating measured retention factors of aliphatic alcohols, phenols and related compounds, and chlorinated hydrocarbons to their octanol:water partition coefficients. The retention mechanism is found to be consistent with a RP-LC mechanism coupled with an additional retention effect due to residual hydroxyl groups on the cyano propyl stationary phase. Advantages due to a 100% water mobile phase for the chemical analysis of alcohol mixtures and chlorinated hydrocarbons are reported. By placing an absorbance detector in-series and preceding a novel drop interface to a flame ionization detector (FID), selective detection of a separated mixture of phenols and related compounds and aliphatic alcohols is achieved. The compound class of aliphatic alcohols is selectively and sensitively detected by the drop interface/FID, and the phenols and related compounds are selectively and sensitively detected by absorbance detection at 200 nm. The separation and detection of chlorinated hydrocarbons in a water sample matrix further illustrated the advantages of this methodology. The sensitivity and selectivity of the FID signal for the chlorinated hydrocarbons are significantly better than absorbance detection, even at 200 nm. This methodology is well suited to continuous and automated monitoring of water samples. The applicability of samples initially in an organic solvent matrix is explored, since an organic sample matrix may effect retention and efficiency. Separations in acetonitrile and isopropyl alcohol sample matrices compared well to separations with a water sample matrix.

Determination of phenolic compounds derived from hydrolysable tannins in biological matrices by RP-HPLC.

PubMed

Díez, María Teresa; García del Moral, Pilar; Resines, José Antonio; Arín, María Jesús

2008-08-01

An RP-HPLC method for the determination of four phenolic compounds: gallic acid (GA), pyrogallol (PY), resorcinol (RE) and ellagic acid (EA), derived from hydrolysable tannins is reported. Separation was achieved on a SunFire C18 (250 x 4.6 mm id, 5 microm) column at 40 degrees C with gradient elution. UV detection at 280 nm was applied. The developed method was validated in terms of linearity, accuracy and precision. Satisfactory repeatability and between day precision were noticed with RSD values lower than 3%. Recoveries from different biological samples ranged from 91.50 to 105.25%. The LODs were estimated as 1.70 mg/L for PY, 1.68 mg/L for GA, 1.52 mg/L for RE and 0.98 mg/L for EA with a 20 microL injection volume. The method was applied for the determination of these compounds in oak leaves and in ruminal fluid and urine samples taken from beef cattle fed with oak leaves. The proposed method could be used in ruminant nutrition studies to verify the effect that a diet rich in tannins have on ruminal fermentation and to determine the toxicity of these compounds.

The role of humic and fulvic acids in the phototransformation of phenolic compounds in seawater.

PubMed

Calza, P; Vione, D; Minero, C

2014-09-15

Humic substances (HS) are known to act as photosensitizers toward the transformation of pollutants in the surface layer of natural waters. This study focused on the role played by HS toward the transformation of xenobiotics in seawater, with the purpose of assessing the prevailing degradation routes. Phenol was chosen as model xenobiotic and its transformation was investigated under simulated sunlight in the presence of terrestrial or marine humic and fulvic acids, in pure water at pH8, artificial seawater (ASW) or natural seawater (NSW). The following parameters were determined: (1) the phenol degradation rate; (2) the variation in HS concentration with irradiation time; (3) the production of transformation products; (4) the influence of iron species on the transformation process. Faster transformation of phenol was observed with humic acids (HA) compared to fulvic acids (SRFA), and transformation induced by both HA and SRFA was faster in ASW than that in pure water. These observations can be explained by assuming an interplay between different competing and sometimes opposite processes, including the competition between chloride, bromide and dissolved oxygen for reaction with HS triplet states. The analysis of intermediates formed in the different matrices under study showed the formation of several hydroxylated (hydroquinone, 1,4-benzoquinone, resorcinol) and condensed compounds (2,2'-bisphenol, 4,4'-bisphenol, 4-phenoxyphenol). Although 1,4-benzoquinone was the main transformation product, formation of condensed molecules was significant with both HA and SRFA. Experiments on natural seawater spiked with HS confirmed the favored formation of condensed products, suggesting a key role of humic matter in dimerization reactions occurring in saline water. Copyright © 2014 Elsevier B.V. All rights reserved.

General Overview of Phenolics from Plant to Laboratory, Good Antibacterials or Not

PubMed Central

Aldulaimi, Omar A.

2017-01-01

The emergence and rapid development of seriously drug-resistant pathogens have created the greatest danger to public health and made the treatment of infectious diseases ineffective; to control the antibiotic-resistant microbes, the discovery of new effective antibacterials with new mechanisms of action against bacteria remains an urgent task to control the bacterial resistance. The paucity of infections in wild plants supports the role of innate defense system of plants. Many researchers nominate the natural extracts to act against bacterial resistance mechanisms, and the majority of them have now been focused on the combination of plant extracts and antibiotics to define the availability of resistance modification agents. Only very few numbers of natural products are successful to reach experiments circle beyond the in vitro assays. Phenols and phenolic acids could serve as good candidates to the natural antibacterial arsenal. The pyrogallol-based compounds are more potent than others such as catechol or resorcinol, gallic acid, and the hydroxycinnamic acid (ferulic acid) are destructing the bacterial cell wall of Staphylococcus aureus, Escherichia coli, and Pseudomonas aeruginosa, leading to leakage of cellular contents. These compounds have stronger activity against Gram-positive microorganisms, and some of them showed good synergism with antibiotics, for example, pentagalloylglucopyranose, is shown a synergism with penicillin G against methicillin-resistant S. aureus, another example is the interesting synergism between epicatechin gallate and oxacillin where the minimal inhibitory concentrations of oxacillin reduced around 500 times by the addition of epicatechin gallate to the antibiotic. PMID:28989246

Acne

MedlinePlus

... a cream or lotion with benzoyl peroxide, resorcinol, salicylic acid, or sulfur. Benzoyl peroxide works to reduce oil made by the glands. Resorcinol, salicylic acid, and sulfur help breakdown whiteheads and blackheads. If ...

Simultaneous Quantification of Dexpanthenol and Resorcinol from Hair Care Formulation Using Liquid Chromatography: Method Development and Validation.

PubMed

De, Amit Kumar; Chowdhury, Partha Pratim; Chattapadhyay, Shyamaprasad

2016-01-01

The current study presents the simultaneous quantification of dexpanthenol and resorcinol from marketed hair care formulation. Dexpanthenol is often present as an active ingredient in personal care products for its beautifying and invigorating properties and restorative and smoothing properties. On the other hand resorcinol is mainly prescribed for the treatment of seborrheic dermatitis of scalp. The toxic side effects of resorcinol limit its use in dermatological preparations. Therefore an accurate quantification technique for the simultaneous estimation of these two components can be helpful for the formulation industries for the accurate analysis of their product quality. In the current study a high performance liquid chromatographic technique has been developed using a C18 column and a mobile phase consisting of phosphate buffer of pH = 2.8 following a gradient elution. The mobile phase flow rate was 0.6 mL per minute and the detection wavelength was 210 nm for dexpanthenol and 280 nm for resorcinol. The linearity study was carried out using five solutions having concentrations ranging between 10.34 μg·mL(-1) and 82.69 μg·mL(-1) (r (2) = 0.999) for resorcinol and 10.44 μg·mL(-1) and 83.50 μg·mL(-1) (r (2) = 0.998) for dexpanthenol. The method has been validated as per ICH Q2(R1) guidelines. The ease of single step sample preparation, accuracy, and precision (intraday and interday) study presents the method suitable for the simultaneous quantification of dexpanthenol and resorcinol from any personal care product and dermatological preparations containing these two ingredients.

Simultaneous Quantification of Dexpanthenol and Resorcinol from Hair Care Formulation Using Liquid Chromatography: Method Development and Validation

PubMed Central

De, Amit Kumar; Chowdhury, Partha Pratim; Chattapadhyay, Shyamaprasad

2016-01-01

The current study presents the simultaneous quantification of dexpanthenol and resorcinol from marketed hair care formulation. Dexpanthenol is often present as an active ingredient in personal care products for its beautifying and invigorating properties and restorative and smoothing properties. On the other hand resorcinol is mainly prescribed for the treatment of seborrheic dermatitis of scalp. The toxic side effects of resorcinol limit its use in dermatological preparations. Therefore an accurate quantification technique for the simultaneous estimation of these two components can be helpful for the formulation industries for the accurate analysis of their product quality. In the current study a high performance liquid chromatographic technique has been developed using a C18 column and a mobile phase consisting of phosphate buffer of pH = 2.8 following a gradient elution. The mobile phase flow rate was 0.6 mL per minute and the detection wavelength was 210 nm for dexpanthenol and 280 nm for resorcinol. The linearity study was carried out using five solutions having concentrations ranging between 10.34 μg·mL−1 and 82.69 μg·mL−1 (r 2 = 0.999) for resorcinol and 10.44 μg·mL−1 and 83.50 μg·mL−1 (r 2 = 0.998) for dexpanthenol. The method has been validated as per ICH Q2(R1) guidelines. The ease of single step sample preparation, accuracy, and precision (intraday and interday) study presents the method suitable for the simultaneous quantification of dexpanthenol and resorcinol from any personal care product and dermatological preparations containing these two ingredients. PMID:27042377

Acne

MedlinePlus

... may contain benzoyl peroxide, sulfur, resorcinol, adapalene, or salicylic acid. They work by killing bacteria, drying up skin ... Prescription formulas of benzoyl peroxide, sulfur, resorcinol, or salicylic acid Topical azelaic acid For women whose acne is ...

[Branch-specific detection of phenols and assessment of ground water solubility].

PubMed

Fischer, F; Kerndorff, H; Kühn, S

2000-01-01

There are about 500 technically relevant phenolic compounds such as cresols, chlorophenols or nitrophenols. It is most preferable to determine phenols as single compounds via gas chromatography. Further, phenols can also be assayed as photometrically as an overall parameter (Phenolindex): however, no conclusions about specific compounds can be drawn from this type of test. Also this method is not as reliable for an hazard assessment as gas chromatography. First, not all phenols, for instance resorcinol or 1-naphthol can be determined with this method. Second, phenolic groups in humic substances, which do not constitute a threat for groundwater, are determined alongside environmentally relevant phenols using this method. In most cases, it is possible to deduce which phenols can be expected in the groundwater of contaminated sites from the type of industrial usage, such as chlorophenols and pulp bleaching or nitrophenols and the production of explosives. Phenols are formed during coal combustion for instance at cokemanufactures or gasworks. They are important raw materials for the chemical industry from which resins, surfactants, pharmaceuticals, pigments, explosives, and stabilizers are produced. During the 80's phenol, cresols, nonylphenols, anisidines, aminophenols, dihydroxybenzenes, and naphthols were manufactured in amounts exceeding 10,000 t/a. Also, phenolic compounds are used as additives in many areas for example as solvents in the electric industry, in sawmills, papermanufacture, electroplating of metal sheets, as photographic developers, as textile dyes, or for the tanning of hydes. Due to the formation and use of phenols at industrial sites, groundwater contaminations are possible via infiltration through the unsaturated zone. Especially at gasworks and ammunition factories, groundwater contaminations with phenols have become known. In the vicinity of railway tracks and associated facillities contaminations due to the use of pesticides or mineral oils are possible. Input of phenols on agricultural lands can be caused by pesticides, sewage sludge or manure. The groundwater downstream of landfills often contains phenol, chlorophenols, cresols, and xylenols. The formation of phenol from other organic contaminants as benzene in groundwater has been reported. The potential for mobilization of phenols in the saturated zone can be estimated from their physical and chemical properties. Especially low molecular weight phenols are easily mobilized due to their high solubility in water and low potential for accumulation. These compounds are: phenol, cresols, xylenols, chlorophenols, hydroxybenzenes, nitrophenols, anisidines, aminophenols, anisol, 2-phenoxyethanol, and thiophenol. The stability of phenols under laboratory conditions varies. The complete mineralization depends mainly on the experimental set-up, i.e. nutrients, temperature, and type of inocula. The anaerobic degradation of phenols is generally slower than the aerobic. Phenol is readily biodegradable under both aerobic and anaerobic conditions. In general, the biodegradability depends on the type, number and position of substitutes. Phenols with nitro-, alkyl-, or chlorosubstitutes are more recalcitrant than phenol itself. Our biodegradability test show that the decomposition of alkylphenols is determined by the length and branching of the alcyllic chain. Phenols with high contamination potential are chlorophenols, xylenols, and nitrophenols. These compounds are both mobile and recalcitrant in the saturated zone. Phenolic compounds of a medium contamination risk are dichlorophenols, trichlorophenols, cresols, and phenol because they are mobile but less stable in groundwater. These compounds are known contaminants in the groundwater at gasworks, landfills, and ammunition factories. Aminophenols, anisidines, tert-butylphenols, ethylphenols, hydroxybenzenes, and 2-phenoxyethanol also constite a potential hazard for groundwater; however, no contaminations with these compounds are known. Poisoning due to oral uptake of phenol contaminated ground- or drinking water have not been reported, which might be due to the pungent odor and taste phenolic compounds have even at very low concentrations (mg/L). Because of the taste problem, the German drinking water standard for phenols is 0.5 microgram/L. In Berlin, groundwater with phenol concentrations higher than 30 micrograms/L of alkylphenols or 2 micrograms/L of chlorophenols is considered contaminated.

Substitution and addition reactions of •OH with p-substituted-phenols

NASA Astrophysics Data System (ADS)

Albarrán, Guadalupe; Galicia-Jiménez, Eduardo; Mendoza, Edith; Schuler, Robert H.

2017-04-01

The directing effect of a hydroxyl group on the substitution and addition reactions of •OH to the substituted and free positions in aromatic rings of p-substituted-phenols were studied in aqueous solutions containing either K3Fe(CN)6 as an oxidant of the substituted hydroxycyclohexadienyl radical initially formed or using ascorbic acid. The results showed that the attack of the •OH to the substituted position (ipso position) was followed by elimination of the substituent producing hydroquinone. The addition reaction of the •OH to the free position on the ring produced 4-substituent-catechol and 4-substituent-resorcinol derivatives. Identification and quantification of the radiolytic products were carried out using high performance liquid chromatography. The results of the yields are given for the p-halogen-phenols (p-X-Ph) p-F-Ph, p-Cl-Ph, p-Br-Ph and p-I-Ph. Other compounds, p-nitro-Ph, p-OH-benzoic acid, p-OH-benzonitrile, p-OH-benzaldehyde, p-OH-anisole and p-OH-benzyl alcohol (represented as p-Z-Ph), were only studied using K3Fe(CN)6 as the oxidant. The results show that the p-X-Ph are attacked by the •OH at the ipso position to the halogen in the proportion 1:0.53:0.46:0.11 for F>Cl>Br>I. The •OH attacked at the ipso position to the p-Z-Phs through a substitution reaction, which depended on the substituent group. Thus, the strongly deactivating groups produced less hydroquinone, indicating less substitution reaction than the strongly activating groups.

Sol-gel coating of inorganic nanostructures with resorcinol-formaldehyde resin.

PubMed

Li, Na; Zhang, Qiao; Liu, Jian; Joo, Jibong; Lee, Austin; Gan, Yang; Yin, Yadong

2013-06-07

A general sol-gel process has been developed to form a coating of resorcinol-formaldehyde (RF) resin on inorganic nanostructures of various compositions and morphologies. The RF shell can be conveniently converted into carbon through high temperature carbonization under an inert atmosphere.

Discovery of 2,4-diarylaminopyrimidines bearing a resorcinol motif as novel ALK inhibitors to overcome the G1202R resistant mutation.

PubMed

Geng, Kaijun; Xia, Zongjun; Ji, Yinchun; Zhang, Ruisi Ruthy; Sun, Deqiao; Ai, Jing; Song, Zilan; Geng, Meiyu; Zhang, Ao

2018-01-20

To address drug resistance caused by ALK kinase mutations, especially the most refractory and predominant mutation G1202R for the second-generation ALK inhibitor, a series of new diarylaminopyrimidine analogues were designed by incorporating a resorcinol moiety (A-ring) to interact the ALK kinase domain where the G1202R is located. Compound 12d turns out as the most potent with IC 50 values of 1.7, 3.5, and 1.8 nM against ALK wild type, gatekeeper mutant L1196M, and the G1202R mutant, respectively. More importantly, compound 12d has excellent inhibitory effects against the proliferation of BaF3 cells specifically expressing ALK wild type, gatekeeper L1196M, and the most challenging mutant G1202R, with IC 50 values all less than 1.5 nM. Collectively, compound 12d is worthy of further investigation as a new more potent third-generation ALK inhibitor to circumvent drug resistance of both the first-generation and the second-generation inhibitors. Copyright © 2017. Published by Elsevier Masson SAS.

Characteristics of the wood adhesion bonding mechanism using hydroxymethyl resorcinol

Treesearch

Douglas J. Gardner; Charles E. Frazier; Alfred W. Christiansen

2006-01-01

A recent collaborative effort among the U.S. Forest Products Laboratory, Virginia Tech, and the University of Maine has explored the possible bonding mechanisms contributing to durable wood adhesive bonding using hydroxymethyl resorcinol (HMR) surface treatment. Current adhesive bonding mechanisms include: mechanical interlocking, electronic or electrostatic theory,...

40 CFR 721.9488 - Substituted resorcinols.

Code of Federal Regulations, 2010 CFR

2010-07-01

... reporting. (1) The chemical substances identified generically as substituted resorcinols (PMNs P-95-1103, P-95-1104, and P-96-1235) are subject to reporting under this section for the significant new uses.... Requirements as specified in § 721.90 (a)(4), (b)(4), and (c)(4) (N = 9). (ii) [Reserved] (b) Specific...

Unprecedented access of phenolic substrates to the heme active site of a catalase: substrate binding and peroxidase-like reactivity of Bacillus pumilus catalase monitored by X-ray crystallography and EPR spectroscopy.

PubMed

Loewen, Peter C; Villanueva, Jacylyn; Switala, Jacek; Donald, Lynda J; Ivancich, Anabella

2015-05-01

Heme-containing catalases and catalase-peroxidases catalyze the dismutation of hydrogen peroxide as their predominant catalytic activity, but in addition, individual enzymes support low levels of peroxidase and oxidase activities, produce superoxide, and activate isoniazid as an antitubercular drug. The recent report of a heme enzyme with catalase, peroxidase and penicillin oxidase activities in Bacillus pumilus and its categorization as an unusual catalase-peroxidase led us to investigate the enzyme for comparison with other catalase-peroxidases, catalases, and peroxidases. Characterization revealed a typical homotetrameric catalase with one pentacoordinated heme b per subunit (Tyr340 being the axial ligand), albeit in two orientations, and a very fast catalatic turnover rate (kcat  = 339,000 s(-1) ). In addition, the enzyme supported a much slower (kcat  = 20 s(-1) ) peroxidatic activity utilizing substrates as diverse as ABTS and polyphenols, but no oxidase activity. Two binding sites, one in the main access channel and the other on the protein surface, accommodating pyrogallol, catechol, resorcinol, guaiacol, hydroquinone, and 2-chlorophenol were identified in crystal structures at 1.65-1.95 Å. A third site, in the heme distal side, accommodating only pyrogallol and catechol, interacting with the heme iron and the catalytic His and Arg residues, was also identified. This site was confirmed in solution by EPR spectroscopy characterization, which also showed that the phenolic oxygen was not directly coordinated to the heme iron (no low-spin conversion of the Fe(III) high-spin EPR signal upon substrate binding). This is the first demonstration of phenolic substrates directly accessing the heme distal side of a catalase. © 2015 Wiley Periodicals, Inc.

New families of carbon gels based on natural resources

NASA Astrophysics Data System (ADS)

Szczurek, Andrzej; Amaral-Labat, Gisele; Fierro, Vanessa; Pizzi, Antonio; Celzard, Alain

2013-03-01

Carbon gels are versatile materials which can be used for many applications. They are extremely expensive, because generally prepared from resorcinol - formaldehyde (RF) resins first gelled and next dried with supercritical carbon dioxide. In the present work, resorcinol has been substituted partly or completely by tannins, a family of molecules extracted from mimosa tree barks. Tannins are natural, non-toxic products, typically thirty times cheaper than resorcinol. Their chemical resemblance with the latter makes them be often called natural resorcinol. Using tannins not only substantially decreases the cost but also allows preparing materials in a much wider range of pHs than that usually employed for RF gels. Consequently the main pore size and the fraction of given families of pores, controlling the carbon gels' properties, are tuned in an easier way, and a much wider range of pore structures is obtained. Finally, two alternative ways of drying are suggested for further decreasing the cost: freeze-drying and supercritical drying in acetone. Both are shown to lead, in some conditions described below, to materials having similar characteristics to those of expensive RF carbon aerogels previously dried in supercritical CO2.

Adsorptive removal of aniline by granular activated carbon from aqueous solutions with catechol and resorcinol.

PubMed

Suresh, S; Srivastava, V C; Mishrab, I M

2012-01-01

In the present paper, the removal of aniline by adsorption process onto granular activated carbon (GAC) is reported from aqueous solutions containing catechol and resorcinol separately. The Taguchi experimental design was applied to study the effect of such parameters as the initial component concentrations (C(0,i)) of two solutes (aniline and catechol or aniline and resorcinol) in the solution, temperature (T), adsorbent dosage (m) and contact time (t). The L27 orthogonal array consisting of five parameters each with three levels was used to determine the total amount of solutes adsorbed on GAC (q(tot), mmol/g) and the signal-to-noise ratio. The analysis of variance (ANOVA) was used to determine the optimum conditions. Under these conditions, the ANOVA shows that m is the most important parameter in the adsorption process. The most favourable levels of process parameters were T = 303 K, m = 10 g/l and t = 660 min for both the systems, qtot values in the confirmation experiments carried out at optimum conditions were 0.73 and 0.95 mmol/g for aniline-catechol and aniline-resorcinol systems, respectively.

Effects of topical application of B-Resorcinol and Glycyrrhetinic acid monotherapy and in combination with fractional CO2 laser treatment for benign hand hyperpigmentation treatment.

PubMed

Grippaudo, Francesca Romana; Di Russo, Pier Paolo

2016-12-01

Hand solar lentigines are frequent benign lesions of elderly population, requiring longtime treatments with topical agents or laser to lighten. The aim of this study was to evaluate and compare the efficacy of CO 2 fractional laser photothermolysis followed by topical application of B-Resorcinol and Glycyrrhetinic acid vs. only topical B-Resorcinol and Glycyrrhetinic acid application for hand solar lentigines treatment. Hand solar lentigines of eleven volunteers were divided into two groups: Group A spots received CO 2 fractional laser photothermolysis followed by 4 weeks topical application of B-Resorcinol and Glycyrrhetinic acid, and Group B spots received only 4 weeks topical treatments. All hands were photographed, and hand solar lentigines scanned with dermatoscope at the beginning of the study (T 0 ), 1 month after laser treatment (T 1 ), and at the end of the study (T 2 ) to document spots dimensions and color. A blinded dermatologist evaluated dermoscopic T 0 and T 2 images. The considered variables were assessed for significance by the nonparametric Mann-Whitney U-test. In all volunteers, investigators and blinded dermatologist's evaluation hand solar lentigines features improved, with no statistical differences in the two groups. Topical application of B-Resorcinol and Glycyrrhetinic acid is effective to lighten hand solar lentigines after 4 weeks of treatment, with or without a previous fractional laser photothermolysis. © 2016 Wiley Periodicals, Inc.

Enhancing and inhibiting effects of aromatic compounds on luminol-dimethylsulfoxide-OH(-) chemiluminescence and determination of intermediates in oxidative hair dyes by HPLC with chemiluminescence detection.

PubMed

Zhou, Jian; Xu, Hong; Wan, Guo-Hui; Duan, Chun-Feng; Cui, Hua

2004-10-08

The effect of 36 aromatic compounds on the luminol-dimethylsulfoxide-OH(-) chemiluminescence (CL) was systematically studied. It was found that dihydroxybenzenes, and ortho- and para-substituted aminophenols and phenylenediamines inhibited the CL and phenols with three or more than three hydroxyls except phloroglucin tended to enhance the CL. The CL inhibition and enhancement was proposed to be dependent on whether superoxide anion radical (O(2)(-)) was competitively consumed by compounds in the CL system. Trihydroxybenzenes were capable of generating superoxide anion radical, leading to the CL enhancement, whereas dihydroxybenzenes were superoxide anion radical scavenger, causing the CL inhibition. Based on the inhibited CL, a novel method for the simultaneous determination of p-phenylenediamine, o-phenylenediamine, p-aminophenol, o-aminophenol, resorcinol and hydroquinone by high-performance liquid chromatography coupled with chemiluminescence detection was developed. The method has been successfully applied to determine intermediates in oxidative hair dyes and wastewater of shampooing after hair dyed.

76 FR 36307 - Guidance for Industry on Topical Acne Drug Products for Over-the-Counter Human Use-Revision of...

Federal Register 2010, 2011, 2012, 2013, 2014

2011-06-22

... the monograph (75 FR 9767, March 4, 2010) (final rule). The guidance describes the requirements of the... products marketed under the monograph (i.e., products that contain any of the active ingredients permitted under the OTC topical acne drug monograph, including benzoyl peroxide, resorcinol, resorcinol...

Improvements to hydroxymethylated resorcinol coupling agent for durable bonding to wood

Treesearch

Alfred W. Christiansen; E. Arnold Okkonen

2003-01-01

Improving the exterior quality bonding of wood to epoxy adhesive resins is important for bonding glass-fiber-reinforced vinyl ester resin laminae to glulam structural members, as well as for repairing glulam members in exterior applications on site. The coupling agent for these applications, hydroxymethylated resorcinol (HMR), was recently improved by using a novolak...

Chemical and mechanical aspects of HMR primer in relationship to wood bonding

Treesearch

Alfred W. Christiansen

2005-01-01

The mechanism by which hydroxymethylated resorcinol (HMR) primer improves the durability of various adhesives to wood has been hypothesized as covalent chemical links between the adhesive and primer and possibly between the primer and wood. The present work presents experiments to test this hypothesis. In the first test, some resorcinol was displaced by 2- methylres-...

Oxygen reduction reaction catalyzed by nickel complexes based on thiophosphorylated calix[4]resorcinols and immobilized in the membrane electrode assembly of fuel cells.

PubMed

Kadirov, M K; Knyazeva, I R; Nizameev, I R; Safiullin, R A; Matveeva, V I; Kholin, K V; Khrizanforova, V V; Ismaev, T I; Burilov, A R; Budnikova, Yu H; Sinyashin, O G

2016-10-18

The catalytic activity of the nickel complexes of thiophosphorylated calix[4]resorcinols for oxygen reduction in a polymer electrolyte membrane fuel cell (PEMFC) has been studied. The conformation of the macrocyclic ligand determines the morphology and catalytic properties of the resulting organometallic species.

Mesoporous carbons and polymers

DOEpatents

Bell, William; Dietz, Steven

2001-01-01

A mesoporous material prepared by polymerizing a resorcinol/formaldehyde system from an aqueous solution containing resorcinol, formaldehyde and a surfactant and optionally pyrolyzing the polymer to form a primarily carbonaceous solid. The material has an average pore size between 4 and 75 nm and is suitable for use in liquid-phase surface limited applications, including sorbent, catalytic, and electrical applications.

Dual Studies on a Hydrogen-Deuterium Exchange of Resorcinol and the Subsequent Kinetic Isotope Effect

ERIC Educational Resources Information Center

Giles, Richard; Kim, Iris; Chao, Weyjuin Eric; Moore, Jennifer; Jung, Kyung Woon

2014-01-01

An efficient laboratory experiment has been developed for undergraduate students to conduct hydrogen-deuterium (H-D) exchange of resorcinol by electrophilic aromatic substitution using D[subscript 2]O and a catalytic amount of H[subscript 2]SO[subscript 4]. The resulting labeled product is characterized by [superscript 1]H NMR. Students also…

Multicentre patch testing with a resol resin based on phenol and formaldehyde.

PubMed

Isaksson, Marléne; Inerot, Annica; Lidén, Carola; Matura, Mihaly; Stenberg, Berndt; Möller, Halvor; Bruze, Magnus

2011-07-01

Contact allergy to phenol-formaldehyde resins (PFRs) based on phenol and formaldehyde is not detected by a p-tertiary-butylphenol-formaldehyde resin (PTBP-FR) included in most baseline patch test series. To investigate the rate of contact allergy to PFR-2 (a mixture of monomers and dimers from a resol resin based on phenol and formaldehyde) in a Swedish population, and to investigate associated simultaneous allergic reactions. Five centres representing the Swedish Contact Dermatitis Research Group included PFR-2 in their patch test baseline series for a period of 1.5 years. Of 2504 patients tested, 27 (1.1%) reacted to PFR-2. Of those 27 individuals, 2 had a positive reaction to formaldehyde and 2 to PTBP-FR. Simultaneous allergic reactions were noted to colophonium in 6, to Myroxylon pereirae in 14, and to fragrance mix I in 15. The contact allergy frequency in the tested population (1.1%) merits its inclusion in the Swedish baseline series and possibly also in other baseline series. Simultaneous allergic reactions were noted to colophonium, M. pereirae, and fragrance mix I. © 2011 John Wiley & Sons A/S.

ANTI-OXIDATIVE, (α-GLUCOSIDASE AND α-AMYLASE INHIBITORY ACTIVITY OF VITEX DONIANA: POSSIBLE EXPLOITATION IN THE MANAGEMENT OF TYPE 2 DIABETES.

PubMed

Ibrahim, Mohammed Auwal; Koorbanally, Neil Anthony; Islam, Shahidul

2016-09-01

Vitex doniana is an important African medicinal plant traditionally used for the treatment of many diseases including type 2 diabetes (T2D). In this study, ethyl acetate, ethanol and aqueous extracts of the stem bark, root and leaf of V. doniana were analyzed for in vitro anti-oxidative activity and the results indicated that the ethanolic extract of the leaves had the best anti-oxidative activity. Subsequently, the ethanolic extract of the leaves was partitioned between hexane, dichloromethane, ethyl acetate and water. The aqueous fraction had a significantly ( p < 0.05) higher phenolics content and also showed the best anti-oxidative activity within the fractions. Furthermore, the aqueous fraction demonstrated significantly (p < 0.05) more potent inhibitory activities against α-glucosidase and α-amylase than other fractions. Steady state kinetics analysis revealed that the aqueous fraction inhibited both (α-glucosidase and (α-amylase activities in a non-competitive manner with inhibition binding constant (Ki) values of 5.93 and 167.44 μg/mL, respectively. Analysis of the aqueous fraction by GC-MS showed the presence of resorcinol, 4-hydroxybenzoic acid, 3,4,5-trimethoxyphenol and 2,4'-dihydroxychalcone identified by their mass fragmentation patterns and comparison to standard spectra. The results obtained in this study showed that V doniana leaves have a good in vitro anti-T2D potential possibly elicited through phenolics.

Effect of ultrasonic waves on the water turbidity during the oxidation of phenol. Formation of (hydro)peroxo complexes.

PubMed

Villota, Natalia; Lomas, Jose M; Camarero, Luis M

2017-11-01

Analysis of the kinetics of aqueous phenol oxidation by a sono-Fenton process reveals that the via involving ortho-substituted intermediates prevails: catechol (25.0%), hydroquinone (7.7%) and resorcinol (0.6%). During the oxidation, water rapidly acquires color that reaches its maximum intensity at the maximum concentration of p-benzoquinone. Turbidity formation occurs at a slower rate. Oxidant dosage determines the nature of the intermediates, being trihydroxylated benzenes (pyrogallol, hydroxyhydroquinone) and muconic acid the main precursors causing turbidity. It is found that the concentration of iron species and ultrasonic waves affects the intensity of the turbidity. The pathway of (hydro)peroxo-iron(II) complexes formation is proposed. Operating with 20.0-27.8mgFe 2+ /kW rates leads to formation of (hydro)peroxo-iron(II) complexes, which induce high turbidity levels. These species would dissociate into ZZ-muconic acid and ferrous ions. Applying relationships around 13.9mgFe 2+ /kW, the formation of (hydro)peroxo-iron(III) complexes would occur, which could react with carboxylic acids (2,5-dioxo-3-hexenedioic acid). That reaction induces turbidity slower. This is due to the organic substrate reacting with two molecules of the (hydro)peroxo complex. Therefore, it is necessary to accelerate the iron regeneration, intensifying the ultrasonic irradiation. Afterwards, this complex would dissociate into maleic acid and ferric ions. Copyright © 2017 Elsevier B.V. All rights reserved.

Solution of Azelaic Acid (20%), Resorcinol (10%) and Phytic Acid (6%) Versus Glycolic Acid (50%) Peeling Agent in the Treatment of Female Patients with Facial Melasma

PubMed Central

Faghihi, Gita; Taheri, Azam; Shahmoradi, Zabihollah; Nilforoushzadeh, Mohammad Ali

2017-01-01

Background: Melasma, a common acquired disorder of hyperpigmentation, especially in women, is often resistant to therapy. This study was aimed to evaluate the efficacy and safety of azelaic acid, resorcinol and phytic acid solution in chemical peeling of melasma in comparison to 50% glycolic acid. Materials and Methods: This clinical trial was performed, on 42 female patients with bilateral melasma. Severity of melasma was assessed by melasma area and severity index (MASI). Combination of (20% azelaic acid + 10% resorcinol + 6% phytic acid) was used as a new peeling agent on the right side of the face and 50% glycolic acid on the left side every 2 weeks for 6 times. Follow-up was carried out for 3 months after the last session. Any decrease in MASI score and unwanted complications following peeling were evaluated and compared during the trial. Results: Patients showed marked improvement as calculated with MASI score before and after treatment in both sides of the face. The efficacy of combination formula (azelaic acid, resorcinol and phytic acid) was similar to glycolic acid, but with fewer complications. There was no statistically difference in improvement between two groups (P > 0.05). However, the patient's discomfort following procedures was significantly lower with azelaic acid, resorcinol and phytic compared with the glycolic acid peels (P < 0.05) and there was the same duration in the beginning of the therapeutic response in both groups. Conclusion: Results showed that triple-combination was found to be an effective and safe peeling agent in the treatment of melasma and it was as effective as 50% glycolic acid peel. PMID:28299301

Determination of synthetic by-products and an intermediate in the colour additives D&C Red Nos 27 and 28 (phloxine B) and their lakes using conventional HPLC.

PubMed

Weisz, Adrian; Krantz, Zoe B

2014-01-01

Specifications in the US Code of Federal Regulations (CFR) for the colour additives D&C Red No. 27 (R27) and D&C Red No. 28 (R28) limit the levels of the synthetic by-products 2,3,4,5-tetrachloro-6-(3´,5´-dibromo-2´,4´-dihydroxybenzoyl)benzoic acid (SBBA) and "brominated resorcinol" and of the intermediate 3,4,5,6-tetrachlorophthalic acid (TCPA). The present study reports the development and application of a conventional HPLC method for the quantitative determination of these impurities in R27, R28 and their lakes. Because the CFR-listed "brominated resorcinol" refers to a group of synthetic by-products, six variously brominated resorcinols were examined as possible impurities. Due to their rapid decomposition in the presence of the dye, the existence of any brominated resorcinols in R27 and R28 is highly unlikely, and this supposition is supported by the results obtained in this study. SBBA, 2,4,6-tribromoresorcinol (Br3R, the brominated resorcinol most likely to be found as an impurity) and TCPA were quantified by using five-point calibration curves with data points (w/w) that ranged from 0.066% to 0.820% for SBBA, from 0.050% to 0.499% for Br3R, and from 0.061% to 1.410% for TCPA. The HPLC method was applied to the analysis of test portions from batches of R27, R28 and their lakes submitted to the USFDA for certification by domestic and foreign manufacturers.

Solution of Azelaic Acid (20%), Resorcinol (10%) and Phytic Acid (6%) Versus Glycolic Acid (50%) Peeling Agent in the Treatment of Female Patients with Facial Melasma.

PubMed

Faghihi, Gita; Taheri, Azam; Shahmoradi, Zabihollah; Nilforoushzadeh, Mohammad Ali

2017-01-01

Melasma, a common acquired disorder of hyperpigmentation, especially in women, is often resistant to therapy. This study was aimed to evaluate the efficacy and safety of azelaic acid, resorcinol and phytic acid solution in chemical peeling of melasma in comparison to 50% glycolic acid. This clinical trial was performed, on 42 female patients with bilateral melasma. Severity of melasma was assessed by melasma area and severity index (MASI). Combination of (20% azelaic acid + 10% resorcinol + 6% phytic acid) was used as a new peeling agent on the right side of the face and 50% glycolic acid on the left side every 2 weeks for 6 times. Follow-up was carried out for 3 months after the last session. Any decrease in MASI score and unwanted complications following peeling were evaluated and compared during the trial. Patients showed marked improvement as calculated with MASI score before and after treatment in both sides of the face. The efficacy of combination formula (azelaic acid, resorcinol and phytic acid) was similar to glycolic acid, but with fewer complications. There was no statistically difference in improvement between two groups ( P > 0.05). However, the patient's discomfort following procedures was significantly lower with azelaic acid, resorcinol and phytic compared with the glycolic acid peels ( P < 0.05) and there was the same duration in the beginning of the therapeutic response in both groups. Results showed that triple-combination was found to be an effective and safe peeling agent in the treatment of melasma and it was as effective as 50% glycolic acid peel.

Continuous tank reactors in series: an improved alternative in the removal of phenolic compounds with immobilized peroxidase.

PubMed

Gómez, E; Máximo, M F; Montiel, M C; Gómez, M; Murcia, M D; Ortega, S

2012-01-01

Immobilized derivatives of soybean peroxidase, covalently bound to a glass support, were used in a continuous stirred tank reactor in series, in order to study the removal of two phenolic compounds: phenol and 4-chlorophenol. The use of two reactors in series, rather than one continuous tank, improved the removal efficiencies of phenol and 4-chlorophenol. The distribution of different amounts of enzyme between the two tanks showed that the relative distributions influenced the removal efficiency reached and the degree of the enzyme deactivation. The highest removal percentages were reached at the outlet of the second tank for a distribution of 50% of the enzyme in each tank. However, with a distribution of 75% in the first tank and 25% in the second, the elimination percentage in the second tank was slightly lower than in the previous case, and the effects of deactivation of the enzyme in the first tank were less pronounced. In all the distributions assayed it was observed that the first tank acts as a filter for the second one, which receives a feed with a smaller load of phenolic compounds, thus diminishing enzyme deactivation in the second tank.

Surface and catalytic properties of acid metal carbons prepared by the sol gel method

NASA Astrophysics Data System (ADS)

Aguado-Serrano, J.; Rojas-Cervantes, M. L.; Martín-Aranda, R. M.; López-Peinado, A. J.; Gómez-Serrano, V.

2006-06-01

The sol-gel method has been applied for the synthesis of a series of acid metal-carbon xerogels (with M = V, Cr, Mo and Ni) by polymerisation of resorcinol with formaldehyde in the presence of metallic precursors. A blank sample was also prepared without any metal addition. The xerogels were heated in nitrogen at 1000 °C to obtain the pyrolysed products. The samples were characterised by different techniques such as thermal-mass spectrometry analysis, gas physisorption, and mercury porosimetry. In addition, the acid character of the pyrolysed products was tested by the Claisen-Schmidt condensation between benzaldehyde and acetophenone for the formation of chalcones.

Molecular simulation and experimental validation of resorcinol adsorption on Ordered Mesoporous Carbon (OMC).

PubMed

Ahmad, Zaki Uddin; Chao, Bing; Konggidinata, Mas Iwan; Lian, Qiyu; Zappi, Mark E; Gang, Daniel Dianchen

2018-04-27

Numerous research works have been devoted in the adsorption area using experimental approaches. All these approaches are based on trial and error process and extremely time consuming. Molecular simulation technique is a new tool that can be used to design and predict the performance of an adsorbent. This research proposed a simulation technique that can greatly reduce the time in designing the adsorbent. In this study, a new Rhombic ordered mesoporous carbon (OMC) model is proposed and constructed with various pore sizes and oxygen contents using Materials Visualizer Module to optimize the structure of OMC for resorcinol adsorption. The specific surface area, pore volume, small angle X-ray diffraction pattern, and resorcinol adsorption capacity were calculated by Forcite and Sorption module in Materials Studio Package. The simulation results were validated experimentally through synthesizing OMC with different pore sizes and oxygen contents prepared via hard template method employing SBA-15 silica scaffold. Boric acid was used as the pore expanding reagent to synthesize OMC with different pore sizes (from 4.6 to 11.3 nm) and varying oxygen contents (from 11.9% to 17.8%). Based on the simulation and experimental validation, the optimal pore size was found to be 6 nm for maximum adsorption of resorcinol. Copyright © 2018 Elsevier B.V. All rights reserved.

Selective hydrogenation of phenol to cyclohexanone over Pd@CN (N-doped porous carbon): Role of catalyst reduction method

NASA Astrophysics Data System (ADS)

Hu, Shuo; Yang, Guangxin; Jiang, Hong; Liu, Yefei; Chen, Rizhi

2018-03-01

Selective phenol hydrogenation is a green and sustainable technology to produce cyclohexanone. The work focused on investigating the role of catalyst reduction method in the liquid-phase phenol hydrogenation to cyclohexanone over Pd@CN (N-doped porous carbon). A series of reduction methods including flowing hydrogen reduction, in-situ reaction reduction and liquid-phase reduction were designed and performed. The results highlighted that the reduction method significantly affected the catalytic performance of Pd@CN in the liquid-phase hydrogenation of phenol to cyclohexanone, and the liquid-phase reduction with the addition of appropriate amount of phenol was highly efficient to improve the catalytic activity of Pd@CN. The influence mechanism was explored by a series of characterizations. The results of TEM, XPS and CO chemisorption confirmed that the reduction method mainly affected the size, surface composition and dispersion of Pd in the CN material. The addition of phenol during the liquid-phase reduction could inhibit the aggregation of Pd NPs and promote the reduction of Pd (2+), and then improved the catalytic activity of Pd@CN. The work would aid the development of high-performance Pd@CN catalysts for selective phenol hydrogenation.

Mechanism of isomers and analogues of resveratrol dimers selectively quenching singlet oxygen by UHPLC-ESI-MS2.

PubMed

Yin, Xuefeng; Yu, Jia; Kong, Qingjun; Ren, Xueyan

2017-12-15

Stilbenoids, in particular, resveratrol and its dimers are abundantly present in Vitis vinifera and proved to be quenchers with selective singlet oxygen. However, only a few mechanisms are reported for their complex molecular architectures. Hence, UHPLC combined with accurate MS is employed to investigate the photo-radiation mechanism of resveratrol dimers systematically. Ⅰ: Resorcinol ring exists in Scirpusin A 1, Trans-ε-viniferin 2 and Trans-σ-viniferin 3. The photochemical products were 14Da or 16Da higher than reagents and underwent an endoperoxide intermediate to quinones; Ⅱ: [2+2] cyclization of intra-molecular trans-double bond. The products were 18Da greater than substrates thereby cycloaddited to oxygen heterocyclic; Ⅲ : [4+1], [4+2] cyclization of oxetane formed products were 28Da and 44Da higher than 3, 2 and 1. Ⅳ : 5-phenol-2,3-dihydrobenzofuran ring exists in 2 been oxidized, causing the products at 16Da, 32Da higher than 2. This is the first to reveal the generally regular mechanism of stilbenoids quenching singlet oxygen. Copyright © 2017 Elsevier Ltd. All rights reserved.

Structure and Electromagnetic Properties of Cellular Glassy Carbon Monoliths with Controlled Cell Size

PubMed Central

Szczurek, Andrzej; Plyushch, Artyom; Macutkevic, Jan

2018-01-01

Electromagnetic shielding is a topic of high importance for which lightweight materials are highly sought. Porous carbon materials can meet this goal, but their structure needs to be controlled as much as possible. In this work, cellular carbon monoliths of well-defined porosity and cell size were prepared by a template method, using sacrificial paraffin spheres as the porogen and resorcinol-formaldehyde (RF) resin as the carbon precursor. Physicochemical studies were carried out for investigating the conversion of RF resin into carbon, and the final cellular monoliths were investigated in terms of elemental composition, total porosity, surface area, micropore volumes, and micro/macropore size distributions. Electrical and electromagnetic (EM) properties were investigated in the static regime and in the Ka-band, respectively. Due to the phenolic nature of the resin, the resultant carbon was glasslike, and the special preparation protocol that was used led to cellular materials whose cell size increased with density. The materials were shown to be relevant for EM shielding, and the relationships between those properties and the density/cell size of those cellular monoliths were elucidated. PMID:29723961

Electrothermal atomic absorption spectrometric determination of copper in nickel-base alloys with various chemical modifiers*1

NASA Astrophysics Data System (ADS)

Tsai, Suh-Jen Jane; Shiue, Chia-Chann; Chang, Shiow-Ing

1997-07-01

The analytical characteristics of copper in nickel-base alloys have been investigated with electrothermal atomic absorption spectrometry. Deuterium background correction was employed. The effects of various chemical modifiers on the analysis of copper were investigated. Organic modifiers which included 2-(5-bromo-2-pyridylazo)-5-(diethylamino-phenol) (Br-PADAP), ammonium citrate, 1-(2-pyridylazo)-naphthol, 4-(2-pyridylazo)resorcinol, ethylenediaminetetraacetic acid and Triton X-100 were studied. Inorganic modifiers palladium nitrate, magnesium nitrate, aluminum chloride, ammonium dihydrogen phosphate, hydrogen peroxide and potassium nitrate were also applied in this work. In addition, zirconium hydroxide and ammonium hydroxide precipitation methods have also been studied. Interference effects were effectively reduced with Br-PADAP modifier. Aqueous standards were used to construct the calibration curves. The detection limit was 1.9 pg. Standard reference materials of nickel-base alloys were used to evaluate the accuracy of the proposed method. The copper contents determined with the proposed method agreed closely with the certified values of the reference materials. The recoveries were within the range 90-100% with relative standard deviation of less than 10%. Good precision was obtained.

Cloning of a Gene Cluster Involved in the Catabolism of p-Nitrophenol by Arthrobacter sp. Strain JS443 and Characterization of the p-Nitrophenol Monooxygenase▿

PubMed Central

Perry, Lynda L.; Zylstra, Gerben J.

2007-01-01

The npd gene cluster, which encodes the enzymes of a p-nitrophenol catabolic pathway from Arthrobacter sp. strain JS443, was cloned and sequenced. Three genes, npdB, npdA1, and npdA2, were independently expressed in Escherichia coli in order to confirm the identities of their gene products. NpdA2 is a p-nitrophenol monooxygenase belonging to the two-component flavin-diffusible monooxygenase family of reduced flavin-dependent monooxygenases. NpdA1 is an NADH-dependent flavin reductase, and NpdB is a hydroxyquinol 1,2-dioxygenase. The npd gene cluster also includes a putative maleylacetate reductase gene, npdC. In an in vitro assay containing NpdA2, an E. coli lysate transforms p-nitrophenol stoichiometrically to hydroquinone and hydroxyquinol. It was concluded that the p-nitrophenol catabolic pathway in JS443 most likely begins with a two-step transformation of p-nitrophenol to hydroxy-1,4-benzoquinone, catalyzed by NpdA2. Hydroxy-1,4-benzoquinone is reduced to hydroxyquinol, which is degraded through the hydroxyquinol ortho cleavage pathway. The hydroquinone detected in vitro is a dead-end product most likely resulting from chemical or enzymatic reduction of the hypothetical intermediate 1,4-benzoquinone. NpdA2 hydroxylates a broad range of chloro- and nitro-substituted phenols, resorcinols, and catechols. Only p-nitro- or p-chloro-substituted phenols are hydroxylated twice. Other substrates are hydroxylated once, always at a position para to a hydroxyl group. PMID:17720792

Porous Media and Mixture Models for Hygrothermal Behavior of Phenolic Composites

NASA Technical Reports Server (NTRS)

Sullivan, Roy M.; Stokes, Eric H.

1999-01-01

Theoretical models are proposed to describe the interaction of water with phenolic polymer. The theoretical models involve the study of the flow of a viscous fluid through a porous media and the thermodynamic theory of mixtures. From the theory, a set of mathematical relations are developed to simulate the effect of water on the thermostructural response of phenolic composites. The expressions are applied to simulate the measured effect of water in a series of experiments conducted on carbon phenolic composites.

Low density, resorcinol-formaldehyde aerogels

DOEpatents

Pekala, Richard W.

1991-01-01

The polycondensation of resorcinol with formaldehyde under alkaline conditions results in the formation of surface functionalized polymer "Clusters". The covalent crosslinking of these "clusters" produces gels which when processed under supercritical conditions, produce low density, organic aerogels (density.ltoreq.100 mg/cc; cell size .ltoreq.0.1 microns). The aerogels are transparent, dark red in color and consist of interconnected colloidal-like particles with diameters of about 100.circle.. These aerogels may be further carbonized to form low density carbon foams with cell size of about 0.1 micron.

Low density, resorcinol-formaldehyde aerogels

DOEpatents

Pekala, Richard W.

1989-01-01

The polycondensation of resorcinol with formaldehyde under alkaline conditions results in the formation of surface functionalized polymer "clusters". The covalent crosslinking of these "clusters" produces gels which when processed under supercritical conditions, produce low density, organic aerogels (density .ltoreq.100 mg/cc; cell size .ltoreq.0.1 microns). The aerogels are transparent, dark red in color and consist of interconnected colloidal-like particles with diameters of about 100 .ANG.. These aerogels may be further carbonized to form low density carbon foams with cell size of about 0.1 micron.

Low density, resorcinol-formaldehyde aerogels

DOEpatents

Pekala, R.W.

1989-10-10

The polycondensation of resorcinol with formaldehyde under alkaline conditions results in the formation of surface functionalized polymer clusters. The covalent crosslinking of these clusters produces gels which when processed under supercritical conditions, produce low density, organic aerogels (density [<=]100 mg/cc; cell size [<=]0.1 microns). The aerogels are transparent, dark red in color and consist of interconnected colloidal-like particles with diameters of about 100 [angstrom]. These aerogels may be further carbonized to form low density carbon foams with cell size of about 0.1 micron.

A comparison of the toxicity and metabolism of phenol and chlorinated phenols by Lemna gibba, with special reference to 2,4,5-trichlorophenol

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

Sharma, H.A.; Barber, J.T.; Ensley, H.E.

1997-02-01

The toxicity of a series of chlorinated phenols, from phenol to pentachlorophenol, was determined using frond reproduction in aseptically grown Lemna gibba. The toxicities of the phenols tended to increase as the number of chlorine substituents on the phenol ring increased. The plants metabolized each of the phenols in the same manner producing metabolites that were more polar than their parent compounds. The metabolite for 2,4,5-trichlorophenol was isolated and identified by nuclear magnetic resonance spectroscopy and chemical ionization mass spectroscopy. The structural identity was confirmed by comparison with synthetic material as 2,4,5-trichlorophenyl-{beta}-D-glucopyranoside. These results, together with previously published results, suggestmore » that conjugation with D-glucose is a stereotypic response of duckweed to challenge by phenol and chlorinated phenols.« less

Pyrolysis g.c.-m.s. of a series of degraded woods and coalified logs that increase in rank from peat to subbituminous coal

USGS Publications Warehouse

Hatcher, P.G.; Lerch, H. E.; Kotra, R.K.; Verheyen, T.V.

1988-01-01

Xylem tissue from degraded wood and coalified logs or stems was examined by pyrolysis g.c.-m.s. to improve understanding of the coalification process. The pyrolysis data, when combined with solid-state 13C n.m.r. data for the same samples, show several stages of evolution during coalification. The first stage, microbial degradation in peat, involves the selective degradation of cellulosic components and preservation of lignin-like components. As coalification increases, the lignin structural units undergo a series of defunctionalization reactions. The first of these involve loss of methoxyl groups, with replacement by phenolic hydroxyls such that catechol-like structures are produced. As the xylem tissue is converted to subbituminous coal, the persistence of phenols and methylated phenols in pyrolysis g.c.-m.s. data of subbituminous coal suggests that the catechol-like structures are being converted to phenol-like structures. The ability to discern detailed changes in the chemical structural composition of a genetically and histologically related series of samples provides an ideal method for developing models of coal structure, especially that of low-rank coal. ?? 1988.

Multicenter Patch Testing With a Resol Resin Based on Phenol and Formaldehyde Within the International Contact Dermatitis Research Group.

PubMed

Isaksson, Marléne; Ale, Iris; Andersen, Klaus; Diepgen, Thomas; Elsner, Peter; Goossens, An; Goh, Chee-Leok; Jerajani, Hemangi; Maibach, Howard; Matsunaga, Kayoko; McFadden, John; Nixon, Rosemary; Sasseville, Denis; Bruze, Magnus

2015-01-01

Contact allergy to phenol-formaldehyde resins (PFRs) based on phenol and formaldehyde is not detected by a p-tertiary-butylphenol-formaldehyde resin included in most baseline patch test series. The aims of this study were to investigate the contact allergy rate to PFR-2 in an international population and to investigate associated simultaneous allergic reactions. Thirteen centers representing the International Contact Dermatitis Research Group included PFR-2 into their patch test baseline series during a period of 6 months in 2012. Of 2259 patients tested, 28 (1.2%) reacted to PFR-2. Of those 28 individuals, one had a positive reaction to formaldehyde and 2 to p-tertiary-butylphenol-formaldehyde resin. Simultaneous allergic reactions were noted to colophonium in 3, to Myroxylon pereirae in 5, and to fragrance mix I in 8. The contact allergy frequency in the tested population (1.2%) merits its inclusion into the international baseline series and possibly also into other baseline series after appropriate investigations. Significantly, overrepresented simultaneous allergic reactions were noted for M. pereirae and fragrance mix I.

Solid phase extraction of magnetic carbon doped Fe3O4 nanoparticles.

PubMed

Yang, Jing; Li, Jia-yuan; Qiao, Jun-qin; Lian, Hong-zhen; Chen, Hong-yuan

2014-01-17

Carbon decorated Fe3O4 nanoparticles (Fe3O4/C) are promising magnetic solid-phase extraction (MSPE) sorbents in environmental and biological analysis. Fe3O4/C based MSPE method shows advantages of easy operation, rapidness, high sensitivity, and environmental friendliness. In this paper, the MSPE mechanism of Fe3O4/C nanoparticles has been comprehensively investigated, for the first time, through the following three efforts: (1) the comparison of extraction efficiency for polycyclic aromatic hydrocarbons (PAHs) between the Fe3O4/C sorbents and activated carbon; (2) the chromatographic retention behaviors of hydrophobic and hydrophilic compounds on Fe3O4/C nanoparticles as stationary phase; (3) related MSPE experiments for several typical compounds such as pyrene, naphthalene, benzene, phenol, resorcinol, anisole and thioanisole. It can be concluded that there are hybrid hydrophobic interaction and hydrogen bonding interaction or dipole-dipole attraction between Fe3O4/C sorbents and analytes. It is the existence of carbon and oxygen-containing functional groups coated on the surface of Fe3O4/C nanoparticles that is responsible for the effective extraction process. Copyright © 2013 Elsevier B.V. All rights reserved.

Optimized structure and thermochemical properties of flavonoids determined by the CHIH(medium) DFT model chemistry versus experimental techniques

NASA Astrophysics Data System (ADS)

Mendoza-Wilson, Ana María.; Lardizabal-Gutiérrez, Daniel; Torres-Moye, Enrique; Fuentes-Cobas, Luis; Balandrán-Quintana, René R.; Camacho-Dávila, Alejandro; Quintero-Ramos, Armando; Glossman-Mitnik, Daniel

2007-12-01

The purpose of this work was to evaluate the accuracy of the CHIH(medium)-DFT model chemistry (PBEg/CBSB2 ∗∗//PBEg/CBSB4) in the determination of the optimized structure and thermochemical properties of heterocyclic systems of medium size such as flavonoids, wherefore were selected three of the most abundant flavonoids in vegetable tissues, and which posses the higher antioxidant activity: quercetin, (+)-catechin and cyanidin. As reference systems were employed three cyclic compounds: phenol, catechol and resorcinol. The thermochemical properties evaluated were enthalpy of formation, bond dissociation enthalpy (BDE) and ionization potential (IP), following the scheme of isodesmic reactions. The theoretical results were compared with experimental data generated by X-ray diffraction and calorimetric techniques realized in part by us, whereas other data were taken from the literature. The results obtained in this work reveal that the CHIH(medium)-DFT model chemistry represents an accurate computational tool to calculate structural and thermochemical properties in the studied flavonoid and reference compounds. The average absolute deviation of enthalpy of formation for reference compounds was 3.0 kcal/mol, 2.64 kcal/mol for BDE, and 2.97 kcal/mol for IP.

Piroxicam cocrystals with phenolic coformers: preparation, characterization, and dissolution properties.

PubMed

Emami, Shahram; Adibkia, Khosro; Barzegar-Jalali, Mohammad; Siahi-Shadbad, Mohammadreza

2018-04-04

This study explores the preparation and investigation of dissolution properties of piroxicam cocrystals. Differential scanning calorimetry (DSC) was used to determine the capability of resorcinol (RES), methylparaben (MPB), and vanillin (VAN) to form cocrystals with piroxicam (PRX). Generation of cocrystals was attempted by liquid assisted grinding and slurry methods. Cocrystals were characterized by thermal methods, powder X-ray diffraction, and Fourier-transform infrared spectroscopy. Apparent solubility, intrinsic dissolution rate (IDR), and powder dissolution profile of cocrystals were compared with anhydrous piroxicam, piroxicam monohydrate (PRXMH), and previously reported piroxicam-succinic acid cocrystal. Contact angles and particle sizes of the studied solids were also measured. Based on the DSC screening results, we prepared and characterized PRX-RES and PRX-MPB cocrystals. Interestingly, the cocrystals not only failed to improve apparent solubility and IDR of PRX but also showed lower values than PRX that were attributed to induction of phase transformation of PRX to PRXMH. In contrary, cocrystals performed better than PRX in powder dissolution studies. The higher dissolution rates of cocrystals were explained by improved wettability and reduced sizes. This study has highlighted the complexity of solid state properties of cocrystals and has provided new evidence for the in-solution stability issues of cocrystals.

Low density, resorcinol-formaldehyde aerogels

DOEpatents

Pekala, R.W.

1988-05-26

The polycondensation of resorcinol with formaldehyde under alkaline conditions results in the formation of surface functionalized polymer ''clusters''. The covalent crosslinking of these ''clusters'' produces gels which when processed under supercritical conditions, produce low density, organic aerogels (density less than or equal to100 mg/cc; cell size less than or equal to0.1 microns). The aerogels are transparent,dark red in color and consist of interconnected colloidal-like particles with diameters of about 100 A/degree/. These aerogels may be further carbonized to form low density carbon foams with cell size of about 0.1 micron. 1 fig., 1 tab.

Ionic Liquids as Solvent, Catalyst Support Chemical Agent Decontamination and Detoxification

DTIC Science & Technology

2004-12-15

agents. 8 3.2 Reactions in surfactant systems Currie studied the reaction between 3-bromo-1-propanol and phenol and a series of phenols carrying...Liquids; Knoche, W., Schomacker, R., Eds.; Springer-Verlag: New York, 1998, pp 1-10. (52) Gonzaga , F.; Perez, E.; Rico-Lattes, I.; Lattes, A. New Journal

Spectroscopic studies of micelle-enhanced ligand exchange of gallium (III)/4-(2-pyridylazo) resorcinol complex by calf thymus DNA.

PubMed

Romeika, Jennifer M; Spurgeon, Charina L; Yan, Fei

2014-01-03

The effect of cationic micelles of cetyltrimethylammonium bromide (CTAB) on the interaction of gallium (III) with 4-(2-pyridylazo) resorcinol (PAR) under varying conditions has been studied spectrophotometrically. At pH 6.0, CTAB (0.05% w/v) markedly enhanced the absorption intensity of gallium (III)-PAR complex. Furthermore, the introduction of CTAB provided unique selectivity for the ligand exchange of Ga(III)-PAR by calf thymus dsDNA over calf thymus ssDNA. This phenomenon offers a novel spectrophotometric sensing strategy for direct detection of dsDNA. Copyright © 2013 Elsevier B.V. All rights reserved.

High strength air-dried aerogels

DOEpatents

Coronado, Paul R.; Satcher, Jr., Joe H.

2012-11-06

A method for the preparation of high strength air-dried organic aerogels. The method involves the sol-gel polymerization of organic gel precursors, such as resorcinol with formaldehyde (RF) in aqueous solvents with R/C ratios greater than about 1000 and R/F ratios less than about 1:2.1. Using a procedure analogous to the preparation of resorcinol-formaldehyde (RF) aerogels, this approach generates wet gels that can be air dried at ambient temperatures and pressures. The method significantly reduces the time and/or energy required to produce a dried aerogel compared to conventional methods using either supercritical solvent extraction. The air dried gel exhibits typically less than 5% shrinkage.

Steric hindrance effects in the use of heterocyclic azodyestuffs as spectrophotometric reagents.

PubMed

Geary, W J; Bottomley, F

1967-05-01

The heterocyclic azo dyestuffs 4-(n-methyl-2 -pyridylazo)-resorcinol (where n = 3', 4', 5', 6') have been prepared, and their possible use as spectrophotometric reagents investigated. The dyestuffs are shown to function analogously to the parent ligand 4-(2'-pyridylazo) resorcinol (PAR) in giving red complexes with the ions Co(2+), Ni(2+), Cu(2+), Zn(2+) and UO(2)(2+). Steric effects resulting from the position of the methyl group in the heterocyclic ring are shown to occur in relation both to the spectra of the dyestuffs themselves and to the sensitivity of their reactions with the metal ions.

INHIBITION OF HUMAN ACETYL- AND BUTYRYLCHOLINESTERASE BY NOVEL CARBAMATES OF (−)- AND (+)-TETRAHYDROFUROBENZOFURAN AND METHANOBENZODIOXEPINE

PubMed Central

Luo, Weiming; Yu, Qian-sheng; Kulkarni, Santosh S.; Parrish, Damon A.; Holloway, Harold W.; Tweedie, David; Shafferman, Avigdor; Lahiri, Debomoy K.; Brossi, Arnold; Greig, Nigel H.

2008-01-01

A new enantiomeric synthesis utilizing classical resolution provided two novel series of optically active inhibitors of cholinesterase: (−)- and (+)- O-carbamoyl phenols of tetrahydrofurobenzofuran and methanobenzodioxepine. An additional two series of (−)- and (+)-O-carbamoyl phenols of pyrroloindole and furoindole were obtained by known procedures, and their anticholinesterase actions were similarly quantified against freshly prepared human acetyl- (AChE) and butyrylcholinesterase (BChE). Both enantiomeric forms of each series demonstrated potent cholinesterase inhibitory activity (with IC50 values as low as 10 nM for AChE and 3 nM for BChE), with the exception of the (+)-O-carbamoyl phenols of pyrroloindole that lacked activity (IC50 values > 1 µM). Based on the biological data of these four series, a SAR analysis was provided by molecular volume calculations. In addition, a probable transition state model was established according to the known X-ray structure of a transition state complex of Torpedo californica AChE-m-(N,N,N,trimethylammonio)-2,2,2-trifluoroacetophenone (TcAChE-TMTFA). This model proved valuable in explaining the enantio-selectivity and enzyme subtype selectivity of each series. These carbamates are more or similarly potent to anticholinesterases in current clinical use; providing not only inhibitors of potential clinical relevance but also pharmacological tools to define drug-enzyme binding interactions within an enzyme crucial in the maintenance of cognition and numerous systemic physiological functions in health, aging and disease. PMID:16570913

Bioenergetic strategy of microalgae for the biodegradation of tyrosol and hydroxytyrosol.

PubMed

Papazi, Aikaterini; Ioannou, Andreas; Symeonidi, Myrto; Doulis, Andreas G; Kotzabasis, Kiriakos

2017-05-01

Olive mill wastewater has significant polluting properties due to its high phenolic content [mainly tyrosol (trs) and hydroxytyrosol (htrs)]. Growth kinetics and a series of fluorescence induction measurements for Scenedesmus obliquus cultures showed that microalgae can be tolerant of these phenolic compounds. Changes in the cellular energy reserves and concentration of the phenolic compounds adjust the "toxicity" of these compounds to the microalgae and are, therefore, the main parameters that affect biodegradation. Autotrophic growth conditions of microalgae and high concentrations of trs or htrs induce higher biodegradation compared with mixotrophic conditions and lower phenolic concentrations. When microalgae face trs and htrs simultaneously, biodegradation begins from htrs, the more energetically demanding compound. All these lead to the conviction that microalgae have a "rational" management of cellular energy balance. Low toxicity levels lead to higher growth and lower biodegradation, whereas higher toxicity levels lead to lower growth and higher biodegradation. The selection of appropriate conditions (compatible to the bioenergetic strategies of microalgae) seems to be the key for a successful biodegradation of a series of toxic compounds, thus paving the way for future biotechnological applications for solving complicated pollution problems, like the detoxification of olive mill wastewater.

Quantitative atomic-scale structure characterization of ordered mesoporous carbon materials by solid state NMR

DOE PAGES

Wang, Zhuoran; Opembe, Naftali; Kobayashi, Takeshi; ...

2018-02-03

In this study, solid-state (SS)NMR techniques were applied to characterize the atomic-scale structures of ordered mesoporous carbon (OMC) materials prepared using Pluronic F127 as template with resorcinol and formaldehyde as polymerizing precursors. A rigorous quantitative analysis was developed using a combination of 13C SSNMR spectra acquired with direct polarization and cross polarization on natural abundant and selectively 13C-enriched series of samples pyrolyzed at various temperatures. These experiments identified and counted the key functional groups present in the OMCs at various stages of preparation and thermal treatment. Lastly, the chemical evolution of molecular networks, the average sizes of aromatic clusters andmore » the extended molecular structures of OMCs were then inferred by coupling this information with the elemental analysis results.« less

Quantitative atomic-scale structure characterization of ordered mesoporous carbon materials by solid state NMR

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

Wang, Zhuoran; Opembe, Naftali; Kobayashi, Takeshi

In this study, solid-state (SS)NMR techniques were applied to characterize the atomic-scale structures of ordered mesoporous carbon (OMC) materials prepared using Pluronic F127 as template with resorcinol and formaldehyde as polymerizing precursors. A rigorous quantitative analysis was developed using a combination of 13C SSNMR spectra acquired with direct polarization and cross polarization on natural abundant and selectively 13C-enriched series of samples pyrolyzed at various temperatures. These experiments identified and counted the key functional groups present in the OMCs at various stages of preparation and thermal treatment. Lastly, the chemical evolution of molecular networks, the average sizes of aromatic clusters andmore » the extended molecular structures of OMCs were then inferred by coupling this information with the elemental analysis results.« less

The Potential of Plant Phenolics in Prevention and Therapy of Skin Disorders

PubMed Central

Działo, Magdalena; Mierziak, Justyna; Korzun, Urszula; Preisner, Marta; Szopa, Jan; Kulma, Anna

2016-01-01

Phenolic compounds constitute a group of secondary metabolites which have important functions in plants. Besides the beneficial effects on the plant host, phenolic metabolites (polyphenols) exhibit a series of biological properties that influence the human in a health-promoting manner. Evidence suggests that people can benefit from plant phenolics obtained either by the diet or through skin application, because they can alleviate symptoms and inhibit the development of various skin disorders. Due to their natural origin and low toxicity, phenolic compounds are a promising tool in eliminating the causes and effects of skin aging, skin diseases, and skin damage, including wounds and burns. Polyphenols also act protectively and help prevent or attenuate the progression of certain skin disorders, both embarrassing minor problems (e.g., wrinkles, acne) or serious, potentially life-threatening diseases such as cancer. This paper reviews the latest reports on the potential therapy of skin disorders through treatment with phenolic compounds, considering mostly a single specific compound or a combination of compounds in a plant extract. PMID:26901191

The Potential of Plant Phenolics in Prevention and Therapy of Skin Disorders.

PubMed

Działo, Magdalena; Mierziak, Justyna; Korzun, Urszula; Preisner, Marta; Szopa, Jan; Kulma, Anna

2016-02-18

Phenolic compounds constitute a group of secondary metabolites which have important functions in plants. Besides the beneficial effects on the plant host, phenolic metabolites (polyphenols) exhibit a series of biological properties that influence the human in a health-promoting manner. Evidence suggests that people can benefit from plant phenolics obtained either by the diet or through skin application, because they can alleviate symptoms and inhibit the development of various skin disorders. Due to their natural origin and low toxicity, phenolic compounds are a promising tool in eliminating the causes and effects of skin aging, skin diseases, and skin damage, including wounds and burns. Polyphenols also act protectively and help prevent or attenuate the progression of certain skin disorders, both embarrassing minor problems (e.g., wrinkles, acne) or serious, potentially life-threatening diseases such as cancer. This paper reviews the latest reports on the potential therapy of skin disorders through treatment with phenolic compounds, considering mostly a single specific compound or a combination of compounds in a plant extract.

Toxicity of phenol and monochlorophenols to growth and metabolic activities of Pseudomonas

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

Huang, D.S.; Tseng, I.C.

1996-07-01

Phenolic compounds are toxic to many organisms and are often present in the effluents from oil refineries, the petrochemical, pesticide, and color and textile industries. Several authors have demonstrated a characteristic pattern of behavioral responses in fishes during phenol exposure. Others have also evaluated the toxicity of halogenated phenolic compounds by screening for effects on the specific growth rates (SGR) and the dehydrogenase activity (DHA) of Escherichia coli. However, little work has been done to determine the effects on biota from short exposures at relatively high concentrations of phenol or monochlorophenols that might occur following a deliberate or accidental dischargemore » to a receiving water. Microorganisms with phenol-degrading capacity have been studied intensively, including cyanobacteria such as Nostoc linckia, yeast such as Trichosporon cutaneum, bacteria such as Pseudomonas putida, and other unidentified species. Among these Pseudomonas has received the most attention and several mutants have been prepared to degrade substituted phenols. This study investigates the initial response of Pseudomonas upon exposure to high concentrations of phenol and chlorophenols by measuring the oxygen uptake rates. A series growth experiment was also conducted in order to compare the kinetic results with standard microbial tests. 12 refs., 3 figs., 1 tab.« less

Nanoindentation mapping of a wood-adhesive bond

NASA Astrophysics Data System (ADS)

Konnerth, J.; Valla, A.; Gindl, W.

2007-08-01

A mapping experiment of a wood phenol-resorcinol-formaldehyde adhesive bond was performed by means of grid nanoindentation. The variability of the modulus of elasticity and the hardness was evaluated for an area of 17 μm by 90 μm. Overall, the modulus of elasticity of the adhesive was clearly lower than the modulus of wood cell walls, whereas the hardness of the adhesive was slightly higher compared to cell walls. A very slight trend of decreasing modulus of elasticity was found with increasing distance from the immediate bond line. However, the trend was superimposed by a high variability of the modulus of elasticity in dependence on the position in the wood cell wall. The unexpectedly high variation of the modulus between 12 and 24 GPa may be explained by the interaction between the helical orientation of the cellulose microfibrils in the S2 layer of the wood cell wall and the geometry of the three-sided Berkovich type indenter pyramid used. Corresponding to the very slight decrease in modulus with increasing distance from the bond line, a similar but clearer trend was found for hardness. Both trends of changing mechanical properties of wood cell walls with varying distance from the bond line are attributed to effects of adhesive penetration into the wood cell wall.

The Nitrite-Scavenging Properties of Catechol, Resorcinol, and Hydroquinone: A Comparative Study on Their Nitration and Nitrosation Reactions.

PubMed

Lu, Yunhao; Dong, Yanzuo; Li, Xueli; He, Qiang

2016-10-14

The nitration and nitrosation reactions of catechol, resorcinol, and hydroquinone (0.05 mmol/L) with sodium nitrite (0.05 mmol/L) at pH 3 and 37 °C were studied by using liquid chromatography and mass spectrometry (LC-MS) and atom charge analysis, which was aimed to provide chemical insight into the nitrite-scavenging behavior of polyphenols. The 3 benzenediols showed different mechanisms to scavenge nitrite due to their differences in hydroxyl position. Catechol was nitrated with 1 NO 2 group at the hydroxyl oxygen, and resorcinol was nitrosated with 2 NO groups at the C 2 and C 4 (or C 6 ) positions of the benzene ring. Hydroquinone could scavenge nitrite through both nitration and nitrosation mechanisms. The nitrated hydroquinone had 1 NO 2 group at the hydroxyl oxygen in the molecule, while the nitrosated 1 containing 2 NO groups at the benzene ring might have 3 structure probabilities. The results may provide a structure-activity understanding on the nitrite-scavenging property of polyphenols, so as to promote their application in the food industry for the removal of possibly toxic nitrites found in many vegetables and often in processed meat products. © 2016 Institute of Food Technologists®.

Incidence of flare-ups and evaluation of quality after retreatment of resorcinol-formaldehyde resin ("Russian Red Cement") endodontic therapy.

PubMed

Gound, Tom G; Marx, David; Schwandt, Nathan A

2003-10-01

The purpose of this retrospective study was to evaluate the quality of treatment and incidence of flare-ups when teeth with resorcinol-formaldehyde resin are retreated in a postgraduate endodontic clinic. Fifty-eight cases were included in this study. Obturated and unfilled canal space was measured on radiographs. Forty-eight percent of the total canal space was filled before retreatment; 90% was filled after retreatment. After retreatment, obturations were rated as optimal in 59%, improved in 33%, unchanged in 6%, and worse in 2%. Seven patients (12%) had postretreatment flare-ups. Data were statistically analyzed using the Cochran-Armitage Test for Discrete Variables. No statistical difference in the incidence of flare-ups was found in teeth that before treatment had more than half the canal space filled compared to teeth with less than half, cases with pre-existing periradicular radiolucencies compared to cases with normal periradicular appearance, symptomatic cases compared to asymptomatic cases, or cases with optimal fillings after retreatment compared to less than optimal cases. It was concluded that teeth with resorcinol-formaldehyde fillings might be retreated with a good prognosis for improving the radiographic quality, but a higher than normal incidence of flare-ups may occur.

A study of cross-reactions between mango contact allergens and urushiol.

PubMed

Oka, Keiko; Saito, Fumio; Yasuhara, Tadashi; Sugimoto, Akiko

2004-01-01

The allergens causing mango dermatitis have long been suspected to be alk(en)yl catechols and/or alk(en)yl resorcinols on the basis of observed cross-sensitivity reactions to mango in patients known to be sensitive to poison ivy and oak (Toxicodendron spp.). Earlier, we reported the 3 resorcinol derivatives: heptadecadienylresorcinol (I), heptadecenylresorcinol (II) and pentadecylresorcinol (III); collectively named 'mangol', as mango allergens. In this study, we extracted the 1st 2 components (I and II) from the Philippine mango, adjusted them to 0.05% concentration in petrolatum and patch tested the components on 2 subjects with mango dermatitis. Both subjects reacted to I. 1 subject also elicited a weaker positive reaction to II. To investigate the cross-reaction between mangol and urushiol, we also patch tested the same subjects with urushiol. The subject sensitive to II reacted to urushiol. 6 subjects with a history of lacquer contact dermatitis and positive reactions to urushiol were similarly patch tested. 5 persons reacted to I. 2 subjects also exhibited a slower but positive reaction to II. This is the 1st report in which heptadec(adi)enyl resorcinols known to be present in mango have been shown to elicit positive patch test reactions in mango-sensitive patients.

Towards a feasible and scalable production of bio-xerogels.

PubMed

Rey-Raap, Natalia; Szczurek, Andrzej; Fierro, Vanessa; Menéndez, J Angel; Arenillas, Ana; Celzard, Alain

2015-10-15

The synthesis process of carbon xerogels is limited, mainly due to two drawbacks that prevent their introduction onto the market: (i) the long time required for producing the material and (ii) the reagents used for the synthesis, which are costly and harmful to the environment. Microwave radiation is expected to produce a reduction in time of more than 90%, while the use of tannin instead of resorcinol will probably result in a cost-effective carbonaceous material. Resorcinol-tannin-formaldehyde xerogels containing different amounts of tannin, either with or without a surfactant (sodium dodecyl sulphate), were synthesized by means of two different heating methods: conventional and microwave heating. The effects of the surfactant, the heating method and the addition of tannin upon the porous structure and the chemical composition of the final materials were evaluated. It was found that the addition of surfactant is essential for obtaining highly porous xerogels when using tannins. The heating method also plays an important role, as conventionally synthesized samples display a greater volume of large pores. However, tannins are less sensitive to microwave radiation and their use results in tannin-formaldehyde xerogels that have a porous structure and chemical composition similar to those of resorcinol-formaldehyde xerogels. Copyright © 2015 Elsevier Inc. All rights reserved.

Evaluation of SRB phenolic TPS material made by an alternate vendor

NASA Technical Reports Server (NTRS)

Karu, Z. S.

1982-01-01

Tests conducted to evaluate the adequacy of solid rocket booster (SRB) phenolic thermal protection system (TPS) material supplied by an alternate vendor chosen by United Space Boosters, Inc. (USBI), to replace the current phenolic TPS sections used thus far on the first four Shuttle flights. The phenolic TPS is applied mainly to the attach and kick rings of the solid rocket booster (SRB). Full-scale sectional models of both the attach and kick ring structure were made up with 0.0265 in. thick stainless steel thin skin covers with thermocouples on them to determine the heating rates. Such models were made up for both the forward and rear faces of the kick ring which has a different configuration on each side. The thin skins were replaced with the alternate phenolic TPS sections cut from flight hardware configuration phenolic parts as supplied by the new vendor. Two tests were performed for each configuration of the attach and kick rings and the samples were exposed to the flow for a duration that gave a heat load equivalent to that obtained in the series of runs made for the current line of phenolic TPS. The samples performed very well with no loss of any phenolic layers. The post-test samples looked better than those used to verify the current phenolic TPS.

PA-1, a Versatile Anaerobe Obtained in Pure Culture, Catabolizes Benzenoids and Other Compounds in Syntrophy with Hydrogenotrophs, and P-2 plus Wolinella sp. Degrades Benzenoids

PubMed Central

Barik, Sudhakar; Brulla, W. J.; Bryant, M. P.

1985-01-01

Methanogenic enrichments catabolizing 13 mM phenylacetate or 4 mM phenol were established at 37°C, using a 10% inoculum from a municipal anaerobic digester. By using agar roll tubes of the basal medium plus 0.1% yeast extract-25 mM fumarate, a hydrogenotrophic lawn of Wolinella succinogenes and phenol or phenylacetate, strains P-2 and PA-1, respectively, were isolated in coculture with W. succinogenes. With the lawn deleted, PA-1 was isolated in pure culture. Strain P-2 is apparently a new species of anaerobic, motile, gram-negative, spindle-shaped, small rod that as yet has been grown only in coculture with W. succinogenes. It used phenol, hydrocinnamate, benzoate, and phenylacetate as energy sources. Product recovery by the coculture, per mole of phenol and 4.4 mol of fumarate used, included 2.03, 0.12, 0.08, and 3.23 mol, respectively, of acetate, propionate, butyrate, and succinate. Carbon recovery was 75% and H recovery was 80%, although CO2 and a few other possible products were not determined. That P-2 is an obligate proton-reducing acetogen and possible pathways for its degradation of phenol are discussed. Strain PA-1 is apparently a new species of anaerobic, motile, relatively small, gram-negative rod. It utilized compounds such as phenylacetate, hydrocinnamate, benzoate, phenol, resorcinol, gallate, 4-aminophenol, 2-aminobenzoate, pyruvate, Casamino Acids, and aspartate as energy sources in coculture with W. succinogenes. Per mole of phenylacetate and 1.44 mol of fumarate used, 1.04, 0.53, and 0.78 mol of acetate, propionate, and succinate, respectively, were recovered from the coculture. Only about 50% of the carbon and H were recovered. In coculture with Methanospirillum hungatei, 0.96 mol of acetate and 0.25 mol of methane were recovered per mol of pyruvate used; 0.90 mol of acetate and 0.33 mol of methane, per mol of fumarate used; 0.93 mol of acetate and 0.54 mol of methane, per mol of aspartate used; and 1.71 mol of acetate and 0.57 mol of methane, per mol of glucose used. Carbon and H recoveries, assuming CO2 and ammonia were produced in stoichiometric amounts, were 97 and 98% for pyruvate, 72.5 and 82% for fumarate, 96.5 and 98% for aspartate, and 61.8 and 76% for glucose. No explanation such as contamination could be found for the fact that the coculture PA-1 plus Wolinella sp. did not use glucose; after growth with M. hungatei on pyruvate, however, the latter coculture used glucose. The PA-1 pure culture produced 0.86 mol of propionate per mol of succinate used during growth. PA-1 produced a small amount of H2. Strain PA-1 is the most versatile anaerobic bacterium yet known that catabolizes monobenzenoids in the absence of electron acceptors such as sulfate or nitrate. PMID:16346852

A functional genomics investigation of allelochemical biosynthesis in Sorghum bicolor root hairs.

PubMed

Baerson, Scott R; Dayan, Franck E; Rimando, Agnes M; Nanayakkara, N P Dhammika; Liu, Chang-Jun; Schröder, Joachim; Fishbein, Mark; Pan, Zhiqiang; Kagan, Isabelle A; Pratt, Lee H; Cordonnier-Pratt, Marie-Michèle; Duke, Stephen O

2008-02-08

Sorghum is considered to be one of the more allelopathic crop species, producing phytotoxins such as the potent benzoquinone sorgoleone (2-hydroxy-5-methoxy-3-[(Z,Z)-8',11',14'-pentadecatriene]-p-benzoquinone) and its analogs. Sorgoleone likely accounts for much of the allelopathy of Sorghum spp., typically representing the predominant constituent of Sorghum bicolor root exudates. Previous and ongoing studies suggest that the biosynthetic pathway for this plant growth inhibitor occurs in root hair cells, involving a polyketide synthase activity that utilizes an atypical 16:3 fatty acyl-CoA starter unit, resulting in the formation of a pentadecatrienyl resorcinol intermediate. Subsequent modifications of this resorcinolic intermediate are likely to be mediated by S-adenosylmethionine-dependent O-methyltransferases and dihydroxylation by cytochrome P450 monooxygenases, although the precise sequence of reactions has not been determined previously. Analyses performed by gas chromatography-mass spectrometry with sorghum root extracts identified a 3-methyl ether derivative of the likely pentadecatrienyl resorcinol intermediate, indicating that dihydroxylation of the resorcinol ring is preceded by O-methylation at the 3'-position by a novel 5-n-alk(en)ylresorcinol-utilizing O-methyltransferase activity. An expressed sequence tag data set consisting of 5,468 sequences selected at random from an S. bicolor root hair-specific cDNA library was generated to identify candidate sequences potentially encoding enzymes involved in the sorgoleone biosynthetic pathway. Quantitative real time reverse transcription-PCR and recombinant enzyme studies with putative O-methyltransferase sequences obtained from the expressed sequence tag data set have led to the identification of a novel O-methyltransferase highly and predominantly expressed in root hairs (designated SbOMT3), which preferentially utilizes alk(en)ylresorcinols among a panel of benzene-derivative substrates tested. SbOMT3 is therefore proposed to be involved in the biosynthesis of the allelochemical sorgoleone.

Phenolics and antioxidant capacity of table grape (Vitis vinifera L.) cultivars grown in Chile.

PubMed

Lutz, Mariane; Jorquera, Katterin; Cancino, Beatriz; Ruby, Rene; Henriquez, Carolina

2011-09-01

Grapes (Vitis vinifera L.) possess health-promoting effects attributed to their supply of a wide variety of bioactive phenolics. Juice and skin fractions of 4 varieties of table grapes: Red Globe, Crimson Seedless, Autumn Royal, and Ribier were prepared to determine and compare their total phenolics content, antioxidant capacity (DPPH, FRAP, and ORAC), anthocyanins, and specific phenolics (caffeic acid, gallic acid, resveratrol, and catechin) content, since a series of positive health benefits are expected from the intake of any of these fractions. Higher amounts of total phenolics and antioxidant capacity were observed in the skin fractions (P < 0.05). Blue grapes (Autumn Royal and Ribier) exhibited higher phenolics content and antioxidant capacity (P < 0.05) than red grapes. The most abundant phenolic compound observed was catechin (P < 0.05). Significant correlations between the antioxidant capacity and total phenolics were observed in grape juice and skin fractions. Autumn Royal juice provides a very high amount of phenolics, anthocyanins, and exhibits the highest antioxidant capacity, offering the best health promoting properties compared with the other grape varieties studied. Grapes possess health-promoting effects attributed to their supply of a wide variety of bioactive phenolics. Grape juice made with blue grapes (Autumn Royal, Ribier) exhibit higher phenolics content and antioxidant capacity than juice elaborated with red grapes (Red Globe, Crimson Seedless). The skin is a good source of phenolics and has a high antioxidant capacity. Specific health-promoting phenolics are more abundant in blue grapes, mainly in their skin fraction, which should not be discarded. © 2011 Institute of Food Technologists®

Effect of Phenol Molecular Structure on Bacterial Transformation Rate Constants in Pond and River Samples

PubMed Central

Paris, Doris F.; Wolfe, N. Lee; Steen, William C.; Baughman, George L.

1983-01-01

Microbial transformation rate constants for a series of phenols were correlated with a property of the substituents, van der Waal's radius. Transformation products were the corresponding catechols, with the exception of p-hydroxybenzoic acid, the product of p-acetylphenol. A different product suggested a different pathway; p-acetylphenol, therefore, was deleted from the data base. PMID:16346236

Phenol oxidation by a sequential CWPO-CWAO treatment with a Fe/AC catalyst.

PubMed

Quintanilla, A; Fraile, A F; Casas, J A; Rodríguez, J J

2007-07-31

Catalytic wet peroxide oxidation (CWPO) of phenol with a homemade Fe/activated carbon (Fe/AC) catalyst has been studied in a stainless steel fixed-bed reactor at different operating conditions (T=23-100 degrees C, P(T)=1-8atm, W=0-2.5g, and tau=20-320g(CAT)h/g(Phenol)). The results show that, thanks to the incorporation of Fe on the activated carbon, phenol conversion improved dramatically, reaching a 90% at 65 degrees C, 2atm, and 40g(CAT)h/g(Phenol). However, TOC conversion values remain fairly low, (around 5% at 40g(CAT)h/g(Phenol)), and no improvement was obtained with the inclusion of Fe. The presence of Fe seems to promote the nondesirable coupling reactions that take place in CWPO of phenol due to the condensation of the ring intermediates (the primary phenol oxidation products). These condensation products are quite refractory to CWPO at the conditions employed. Taking advantage of the high phenol conversions in CWPO and the high phenol mineralization in CWAO, along with the good stability of the Fe/AC catalyst, a CWPO-CWAO sequential treatment has been successfully performed by using a fixed-bed and trickle-bed reactor in series. A CWPO treatment at ambient conditions followed by a CWAO treatment at mild conditions (100 degrees C and 8atm) is presented as high efficiency process for the decontamination of phenolic wastewaters.

Selection of anion exchangers for detoxification of dilute-acid hydrolysates from spruce.

PubMed

Horváth, Ilona Sárvári; Sjöde, Anders; Nilvebrant, Nils-Olof; Zagorodni, Andrei; Jönsson, Leif J

2004-01-01

Six anion-exchange resins with different properties were compared with respect to detoxification of a dilute-acid hydrolysate of spruce prior to ethanolic fermentation with Saccharomyces cerevisiae. The six resins encompassed strong and weak functional groups as well as styrene-, phenol-, and acrylic-based matrices. In an analytical experimental series, fractions from columns packed with the different resins were analyzed regarding pH, glucose, furfural, hydroxymethylfurfural, phenolic compounds, levulinic acid, acetic acid, formic acid, and sulfate. An initial adsorption of glucose occurred in the strong alkaline environment and led to glucose accumulation at a later stage. Acetic and levulinic acid passed through the column before formic acid, whereas sulfate had the strongest affinity. In a preparative experimental series, one fraction from each of six columns packed with the different resins was collected for assay of the fermentability and analysis of glucose, mannose, and fermentation inhibitors. The fractions collected from strong anion-exchange resins with styrene-based matrices displayed the best fermentability: a sevenfold enhancement of ethanol productivity compared with untreated hydrolysate. Fractions from a strong anion exchanger with acrylic-based matrix and a weak exchanger with phenol-based resin displayed an intermediate improvement in fermentability, a four- to fivefold increase in ethanol productivity. The fractions from two weak exchangers with styrene- and acrylic-based matrices displayed a twofold increase in ethanol productivity. Phenolic compounds were more efficiently removed by resins with styrene- and phenol-based matrices than by resins with acrylic-based matrices.

Oxidative polycondensation of benzimidazole using NaOCl: Synthesis, characterization, optical, thermal and electrical properties of polybenzimidazoles

NASA Astrophysics Data System (ADS)

Anand, Siddeswaran; Muthusamy, Athianna; Dineshkumar, Sengottuvelu; Chandrasekaran, J.

2017-11-01

A series of polybenzimidazole polymers, poly-2-(1H-benzo[d] imidazole-2-yl) phenol (PBIP2), poly-3-(1H-benzo[d] imidazole-2-yl) phenol (PBIP3) and poly-4-(1H-benzo[d] imidazole-2-yl) phenol (PBIP4) were synthesized by oxidative polycondensation of benzimidazole monomers 2-(1H-benzo [d] imidazole-2-yl) phenol (BIP2), 3-(1H-benzo [d] imidazole-2-yl) phenol (BIP3) and 4-(1H-benzo [d] imidazole-2-yl) phenol (BIP4). The structure of benzimidazoles monomers and polybenzimidazoles (PBI) were confirmed by various spectroscopic techniques. The quantum theoretical calculations of band gap energy values of monomers were done with DFT and are compared with its optical band gap energy values. Fluorescence spectra of these compounds showed maximum emission in blue region. The electrical conductivity of PBIs was measured by four-point probe technique and showed good electrical response on iodine doping and conductivity increases with increase iodine doping time. The differences in conductivities among the three PBIs are in accordance with the charge density on imidazole nitrogens calculated by Huckel method. The high carbines residue (∼40%) at 500 °C in thermo gravimetric analysis shows that the PBIs are having reasonably good thermal stability. Polymers have recorded high dielectric constant at low applied frequency of 50 Hz at 393 K. The I-V characteristics of polybenzimidazoles p-n diodes showed rectifying nature with a typical forward to reverse current in the range -4 to 4 V. The high n values are caused by non homogeneities and effect of series resistance.

On the origin of donor O–H bond weakening in phenol-water complexes

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

Banerjee, Pujarini; Mukhopadhyay, Deb Pratim; Chakraborty, Tapas, E-mail: pctc@iacs.res.in

2015-11-28

Matrix isolation infrared spectroscopy has been used to investigate intermolecular interactions in a series of binary O–H⋯O hydrogen bonded phenol-water complexes where water is the common acceptor. The interaction at the binding site has been tuned by incorporating multiple fluorine substitutions at different aromatic ring sites of the phenol moiety. The spectral effects for the aforesaid chemical changes are manifested in the infrared spectra of the complexes as systematic increase in spectral shift of the phenolic O–H stretching fundamental (Δν{sub O–H}). While ν{sub O–H} bands of the monomers of all the fluorophenols appear within a very narrow frequency range, themore » increase in Δν{sub O–H} of the complexes from phenol to pentafluorophenol is very large, nearly 90%. The observed values of Δν{sub O–H} do not show a linear correlation with the total binding energies (ΔE{sub b}) of the complexes, expected according to Badger-Bauer rule. However, in the same Δν{sub O–H} vs ΔE{sub b} plot, nice linear correlations are revealed if the complexes of ortho-fluorophenols are treated separately from their meta/para-substituted analogues. The observations imply that in spite of having the same binding site (O–H⋯O) and the same chemical identities (phenolic), the complexes of ortho and non-ortho fluorophenols do not belong, from the viewpoint of detailed molecular interactions, to a homologous series. Linear correlations of Δν{sub O–H} are, however, observed with respect to the electrostatic component of ΔE{sub b} as well as the quantum mechanical charge transfer interaction energy (E{sub CT}). From quantitative viewpoint, the latter correlation along with the associated electronic structure parameters appears more satisfactory. It has also been noted that the observed Δν{sub O–H} values of the complexes display a linear relationship with the aqueous phase pK{sub a} values of the respective phenol derivatives.« less

A Laboratory Exercise to Understand the Importance of Enzyme Technology in the Fruit-Processing Industry: Viscosity Decrease and Phenols Release from Apple Mash

ERIC Educational Resources Information Center

Pinelo, Manuel; Nielsen, Michael K.; Meyer, Anne S.

2011-01-01

In a 4-h laboratory exercise, students accomplish a series of enzymatic macerations of apple mash, assess the viscosity of the mash during the maceration, extract the juice by centrifugation, and measure the levels of antioxidant phenols extracted into the juice after different enzyme treatments. The exercise shows the impact of enzyme-catalyzed…

Phenols in hydrothermal petroleums and sediment bitumen from Guaymas Basin, Gulf of California

NASA Technical Reports Server (NTRS)

Simoneit, B. R.; Leif, R. N.; Ishiwatari, R.

1996-01-01

The aliphatic, aromatic and polar (NSO) fractions of seabed petroleums and sediment bitumen extracts from the Guaymas Basin hydrothermal system have been analyzed by gas chromatography and gas chromatography-mass spectrometry (free and silylated). The oils were collected from the interiors and exteriors of high temperature hydrothermal vents and represent hydrothermal pyrolyzates that have migrated to the seafloor by hydrothermal fluid circulation. The downcore sediments are representative of both thermally unaltered and thermally altered sediments. The survey has revealed the presence of oxygenated compounds in samples with a high degree of thermal maturity. Phenols are one class of oxygenated compounds found in these samples. A group of methyl-, dimethyl- and trimethyl-isoprenoidyl phenols (C27-C29) is present in all of the seabed NSO fractions, with the methyl- and dimethyl-isoprenoidyl phenols occurring as major components, and a trimethyl-isoprenoidyl phenol as a minor component. A homologous series of n-alkylphenols (C13-C33) has also been found in the seabed petroleums. These phenols are most likely derived from the hydrothermal alteration of sedimentary organic matter. The n-alkylphenols are probably synthesized under hydrothermal conditions, but the isoprenoidyl phenols are probably hydrothermal alteration products of natural product precursors. The suites of phenols do not appear to be useful tracers of high temperature hydrothermal processes.

Density functional theory study of hydrogen atom abstraction from a series of para-substituted phenols: why is the Hammett σ(p)+ constant able to represent radical reaction rates?

PubMed

Yoshida, Tatsusada; Hirozumi, Koji; Harada, Masataka; Hitaoka, Seiji; Chuman, Hiroshi

2011-06-03

The rate of hydrogen atom abstraction from phenolic compounds by a radical is known to be often linear with the Hammett substitution constant σ(+), defined using the S(N)1 solvolysis rates of substituted cumyl chlorides. Nevertheless, a physicochemical reason for the above "empirical fact" has not been fully revealed. The transition states of complexes between the 2,2-diphenyl-1-picrylhydrazyl radical (dpph·) and a series of para-substituted phenols were determined by DFT (Density Functional Theory) calculations, and then the activation energy as well as the homolytic bond dissociation energy of the O-H bond and charge distribution in the transition state were calculated. The heterolytic bond dissociation energy of the C-Cl bond and charge distribution in the corresponding para-substituted cumyl chlorides were calculated in parallel. Excellent correlations among σ(+), charge distribution, and activation and bond dissociation energies revealed quantitatively that there is a strong similarity between the two reactions, showing that the electron-deficiency of the π-electron system conjugated with a substituent plays a crucial role in determining rates of the two reactions. The results provide a new insight into and physicochemical understanding of σ(+) in the hydrogen abstraction from substituted phenols by a radical.

Development of aircraft lavatory compartments with improved fire resistance characteristics. Phase 2: Sandwich panel resin system development

NASA Technical Reports Server (NTRS)

Anderson, R. A.; Arnold, D. B.; Johnson, G. A.

1979-01-01

A NASA-funded program is described which aims to develop a resin system for use in the construction of lavatory wall panels, sidewall panels, and ceiling panels possessing flammability, smoke and gas emission, and toxicity (FS&T) characteristics superior to the existing epoxy resin. Candidate resins studied were phenolic, polyimide, and bismaleimide. Based on the results of a series of FS&T as well as mechanical and aesthetic property tests, a phenolic resin was chosen as the superior material. Material and process specifications covering the phenolic resin based materials were prepared and a method of rating sandwich panel performance was developed.

A finite element method for the thermochemical decomposition of polymeric materials. II - Carbon phenolic composites

NASA Technical Reports Server (NTRS)

Sullivan, R. M.; Salamon, N. J.

1992-01-01

A previously developed formulation for modeling the thermomechanical behavior of chemically decomposing, polymeric materials is verified by simulating the response of carbon phenolic specimens during two high temperature tests: restrained thermal growth and free thermal expansion. Plane strain and plane stress models are used to simulate the specimen response, respectively. In addition, the influence of the poroelasticity constants upon the specimen response is examined through a series of parametric studies.

Acne -- self-care

MedlinePlus

... It may help to use a wash with salicylic acid or benzoyl if your skin is oily and ... products may contain benzoyl peroxide, sulfur, resorcinol, or salicylic acid. They work by killing bacteria, drying up skin ...

Reactions of the phthalimide N-oxyl radical (PINO) with activated phenols: the contribution of π-stacking interactions to hydrogen atom transfer rates.

PubMed

D'Alfonso, Claudio; Bietti, Massimo; DiLabio, Gino A; Lanzalunga, Osvaldo; Salamone, Michela

2013-02-01

The kinetics of reactions of the phthalimide N-oxyl radical (PINO) with a series of activated phenols (2,2,5,7,8-pentamethylchroman-6-ol (PMC), 2,6-dimethyl- and 2,6-di-tert-butyl-4-substituted phenols) were investigated by laser flash photolysis in CH(3)CN and PhCl in order to establish if the reactions with PINO can provide a useful tool for evaluating the radical scavenging ability of phenolic antioxidants. On the basis of the small values of deuterium kinetic isotope effects, the relatively high and negative ρ values in the Hammett correlations and the results of theoretical calculations, we suggest that these reactions proceed by a hydrogen atom transfer (HAT) mechanism having a significant degree of charge transfer resulting from a π-stacked conformation between PINO and the aromatic ring of the phenols. Kinetic solvent effects were analyzed in detail for the hydrogen transfer from 2,4,6-trimethylphenol to PINO and the data obtained are in accordance with the Snelgrove-Ingold equation for HAT. Experimental rate constants for the reactions of PINO with activated phenols are in accordance with those predicted by applying the Marcus cross relation.

Designing of phenol-based β-carbonic anhydrase1 inhibitors through QSAR, molecular docking, and MD simulation approach.

PubMed

Ahamad, Shahzaib; Hassan, Md Imtaiyaz; Dwivedi, Neeraja

2018-05-01

Tuberculosis (Tb) is an airborne infectious disease caused by Mycobacterium tuberculosis. Beta-carbonic anhydrase 1 ( β-CA1 ) has emerged as one of the potential targets for new antitubercular drug development. In this work, three-dimensional quantitative structure-activity relationships (3D-QSAR), molecular docking, and molecular dynamics (MD) simulation approaches were performed on a series of natural and synthetic phenol-based β-CA1 inhibitors. The developed 3D-QSAR model ( r 2  = 0.94, q 2  = 0.86, and pred_r 2  = 0.74) indicated that the steric and electrostatic factors are important parameters to modulate the bioactivity of phenolic compounds. Based on this indication, we designed 72 new phenolic inhibitors, out of which two compounds (D25 and D50) effectively stabilized β-CA1 receptor and, thus, are potential candidates for new generation antitubercular drug discovery program.

Shell thickness-dependent microwave absorption of core-shell Fe3O4@C composites.

PubMed

Du, Yunchen; Liu, Wenwen; Qiang, Rong; Wang, Ying; Han, Xijiang; Ma, Jun; Xu, Ping

2014-08-13

Core-shell composites, Fe3O4@C, with 500 nm Fe3O4 microspheres as cores have been successfully prepared through in situ polymerization of phenolic resin on the Fe3O4 surface and subsequent high-temperature carbonization. The thickness of carbon shell, from 20 to 70 nm, can be well controlled by modulating the weight ratio of resorcinol and Fe3O4 microspheres. Carbothermic reduction has not been triggered at present conditions, thus the crystalline phase and magnetic property of Fe3O4 micropsheres can be well preserved during the carbonization process. Although carbon shells display amorphous nature, Raman spectra reveal that the presence of Fe3O4 micropsheres can promote their graphitization degree to a certain extent. Coating Fe3O4 microspheres with carbon shells will not only increase the complex permittivity but also improve characteristic impedance, leading to multiple relaxation processes in these composites, thus the microwave absorption properties of these composites are greatly enhanced. Very interestingly, a critical thickness of carbon shells leads to an unusual dielectric behavior of the core-shell structure, which endows these composites with strong reflection loss, especially in the high frequency range. By considering good chemical homogeneity and microwave absorption, we believe the as-fabricated Fe3O4@C composites can be promising candidates as highly effective microwave absorbers.

Decontamination of spent ion-exchangers contaminated with cesium radionuclides using resorcinol-formaldehyde resins.

PubMed

Palamarchuk, Marina; Egorin, Andrey; Tokar, Eduard; Tutov, Mikhail; Marinin, Dmitry; Avramenko, Valentin

2017-01-05

The origin of the emergence of radioactive contamination not removable in the process of acid-base regeneration of ion-exchange resins used in treatment of technological media and liquid radioactive waste streams has been determined. It has been shown that a majority of cesium radionuclides not removable by regeneration are bound to inorganic deposits on the surface and inside the ion-exchange resin beads. The nature of the above inorganic inclusions has been investigated by means of the methods of electron microscopy, IR spectrometry and X-ray diffraction. The method of decontamination of spent ion-exchange resins and zeolites contaminated with cesium radionuclides employing selective resorcinol-formaldehyde resins has been suggested. Good prospects of such an approach in deep decontamination of spent ion exchangers have been demonstrated. Copyright © 2016 Elsevier B.V. All rights reserved.

The chemical structure of Gloeocapsomorpha prisca microfossils: implications for their origin

NASA Astrophysics Data System (ADS)

Blokker, Peter; van Bergen, Pim; Pancost, Rich; Collinson, Margaret E.; de Leeuw, Jan W.; Sinninghe Damste, Jaap S.

2001-03-01

Two Estonian Kukersites (Ordovician) and two samples from the Guttenberg Member (Ordovician) of the Decorah formation (North America) containing botryoidal aggregates of Gloeocapsomorpha prisca were investigated by RuO 4 chemical degradation, FTIR, and flash pyrolysis-GC/MS to obtain information about the polymeric structure of these microfossils. The products formed upon oxidation by RuO 4 were analysed by GC/MS and revealed the presence of a wide range of carboxyl and/or carbonyl moiety containing compounds with carbon skeletons ranging from C 5 to C 20. The Estonian Kukersites reveal the presence of a characteristic set of mono-, di-, and tricarboxylic acids. These compounds suggest that the Estonian Kukersites are composed of a polymer consisting of mainly C 21 and C 23n-alkenyl resorcinol building blocks. Similarly, although the tricarboxylic acids are not present, the RuO 4 degradation product mixtures of the Guttenberg Member samples, suggest a poly( n-alkyl resorcinol) structure. The higher thermal maturity is most likely responsible for the different chemistry and morphology of the G. prisca microfossils in these samples. Because compounds like n-alkenyl resorcinols are known to polymerise under oxygenated conditions even in an aqueous environment, it is not per se necessary that these microfossils are composed of a selectively preserved biopolymeric cell wall. It is also possible that G. prisca microfossils are composed of a cell wall or sheath component that polymerised during senescence or diagenesis of the organism.

Kinetics and structure-activity relationship of dendritic bridged hindered phenol antioxidants to protect styrene against free radical induced peroxidation

NASA Astrophysics Data System (ADS)

Li, Cui-Qin; Guo, Su-Yue; Wang, Jun; Shi, Wei-Guang; Zhang, Zhi-Qiu; Wang, Peng-Xiang

2017-12-01

A series of dendritic poly(amido-amine) (PAMAM) bridged hindered phenols antioxidants were synthesized. The active antioxidant group (3-(3,5-di- tert-butyl-4-hydroxyphenyl)propionic acid) was attached to two generations of PAMAM dendrimers, and their structure was verified by nuclear magnetic resonance (NMR) and fourier transform infrared spectra (FT-IR). The antioxidant abilities of the dendritic phenols to inhibit the oxidation of styrene were evaluated and the relationships between the length of core, the generation of dendrimers and the antioxidant activities were established. The reaction kinetics of scavenging peroxyl radicals was followed by oxygen consumption. The inhibition time ( t inh) values showed the dendritic phenols had the ability of scavenging peroxyl radicals, and that the antioxidant ability increased with the increasing length of the core and the generation. The kinetic analysis demonstrated that dendritic phenols could slow the rate of styrene peroxidation induced by AIBN, as shown by the number of trapping ROO· ( n), and this role was in accordance with that of the t inh values.

Tyrosinase-containing chitosan gels: A combined catalyst and sorbent for selective phenol removal

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

Sun, W.Q.; Payne, G.F.

There are a series of examples in which phenols appear as contaminants in process streams and their selective removal is required for waste minimization. For the selective removal of a phenol from a mixture, the authors are exploiting the substrate specificity of the enzyme tyrosinase to convert phenols into reactive o-quinones which are then adsorbed onto the amine-containing polymer chitosan. To effectively package the enzyme and sorbent, tyrosinase was immobilized between two chitosan gel films. The entrapment of tyrosinase between the films led to little loss of activity during immobilization, while tyrosinase leakage during incubation was limited. The chitosan gelsmore » rapidly adsorb the tyrosinase-generated product(s) of phenol oxidation while the capacity of the gels is substantially greater than the capacity of chitosan flakes. The performance of tyrosinase-containing chitosan gels significantly depends on the ratio of tyrosinase-to-chitosan. High tyrosinase-to-chitosan ratios result in less efficient use of tyrosinase, presumably due to suicide inactivation. However, the efficiency of chitosan use increases with increased tyrosinase-to-chitosan ratios.« less

Sorption of halogenated phenols and pharmaceuticals to biochar: affecting factors and mechanisms.

PubMed

Oh, Seok-Young; Seo, Yong-Deuk

2016-01-01

The feasibility of using biochar as a sorbent to remove nine halogenated phenols (2,4-dichlorophenol, 2,4-dibromophenol, 2,4-difluorophenol, 2-chlorophenol, 4-chlorophenol, 2-bromophenol, 4-bromophenol, 2-fluorophenol, and 4-fluorophenol) and two pharmaceuticals (triclosan and ibuprofen) from water was examined through a series of batch experiments. Types of biochar, synthesized using various biomasses including fallen leaves, rice straw, corn stalk, used coffee grounds, and biosolids, were evaluated. Compared to granular activated carbon (GAC), most of the biochar samples did not effectively remove halogenated phenols or pharmaceuticals from water. The increase in pH and deprotonation of phenols in biochar systems may be responsible for its ineffectiveness at this task. When pH was maintained at 4 or 7, the sorption capacity of biochar was markedly increased. Considering maximum sorption capacity and properties of sorbents and sorbates, it appears that the sorption capacity of biochar for halogenated phenols is related to the surface area and carbon content of the biochar and the hydrophobicity of halogenated phenols. In the cases of triclosan and ibuprofen, the sorptive capacities of GAC, graphite, and biochars were also significantly affected by pH, according to the point of zero charge (PZC) of sorbents and deprotonation of the pharmaceuticals. Pyrolysis temperature did not affect the sorption capacity of halogenated phenols or pharmaceuticals. Based on the experimental observations, some biochars are good candidates for removal of halogenated phenols, triclosan, and ibuprofen from water and soil.

Gallium(III)/4-(2-pyridylazo)resorcinol system in water and SDS solution: kinetics and thermodynamics.

PubMed

Biver, T; Boggioni, A; Secco, F; Venturini, M

2008-01-01

The equilibria and kinetics of the complex formation and dissociation reaction between gallium(III) and PAR [4-(2-pyridylazo)resorcinol] have been investigated in water and in the presence of SDS micelles. The reactive form of Ga(III) is GaOH2+ in both cases. The addition of SDS results in an increase of both the binding affinity and velocity, the maximum accelerating effect being observed just above the cmc value of SDS that, under the conditions of the experiments, is 5.6 x 10-3 M. At pH = 3.2, the maximum value of the equilibrium constant ratio Kapp(SDS)/Kapp(H2O) is 27.4, whereas that of the binding rate constants kf(SDS)/kf(H2O) is 16. The results are interpreted in terms of increased concentrations of the reactants on the micelle surface and on competition of PAR and SDS for GaOH2+.

Inhibitory effects of cardols and related compounds on superoxide anion generation by xanthine oxidase.

PubMed

Masuoka, Noriyoshi; Nihei, Ken-ichi; Maeta, Ayami; Yamagiwa, Yoshiro; Kubo, Isao

2015-01-01

5-Pentadecatrienylresorcinol, isolated from cashew nuts and commonly known as cardol (C₁₅:₃), prevented the generation of superoxide radicals catalysed by xanthine oxidase without the inhibition of uric acid formation. The inhibition kinetics did not follow the Michelis-Menten equation, but instead followed the Hill equation. Cardol (C₁₀:₀) also inhibited superoxide anion generation, but resorcinol and cardol (C₅:₀) did not inhibit superoxide anion generation. The related compounds 3,5-dihydroxyphenyl alkanoates and alkyl 2,4-dihydroxybenzoates, had more than a C9 chain, cooperatively inhibited but alkyl 3,5-dihydroxybenzoates, regardless of their alkyl chain length, did not inhibit the superoxide anion generation. These results suggested that specific inhibitors for superoxide anion generation catalysed by xanthine oxidase consisted of an electron-rich resorcinol group and an alkyl chain having longer than C9 chain. Copyright © 2014 Elsevier Ltd. All rights reserved.

Adsorption/electrosorption of catechol and resorcinol onto high area activated carbon cloth.

PubMed

Bayram, Edip; Hoda, Numan; Ayranci, Erol

2009-09-15

Removal of catechol and resorcinol from aqueous solutions by adsorption and electrosorption onto high area activated carbon cloth (ACC) was investigated. Kinetics of both adsorption and electrosorption were followed by in-situ UV-spectroscopic method and the data were treated according to pseudo-first-order, pseudo-second-order and intraparticle diffusion models. It was found that the adsorption and electrosorption of these compounds onto ACC follows pseudo-second-order model. pH changes during adsorption and electrosorption were followed and discussed with regard to the interaction between ACC and adsorbate molecules, utilizing the pH(pzc) value of ACC. An electrodesorption experiment was conducted to explore the possibility of regeneration of ACC. Adsorption isotherms were derived at 25 degrees C on the basis of batch analysis. The fits of experimental isotherm data to the well-known Freundlich, Langmuir and Tempkin models were examined.

Hugoniots of aerogels involving carbon and resorcinol formaldehyde

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

Hrubesh, L H; Ree, F H; Schmidt, R D

1999-06-24

Recently, a first-order phase transition is predicted in liquid carbon using atomistic simulation and Brenner's bond order potential. There are also experimental data suggesting a possibility for a first-order phase transition. In light of this, a thermochemical equilibrium code (CHEQ) is used to provide guidance to experiments to find a liquid-liquid phase change in carbon foam and carbon-rich aerogel, resorcinol formaldehyde. Isotherms and Hugoniots were computed based on the previous analysis by van Thiel and Ree. The present calculations predict the liquid-liquid-graphite triple point to be at 5000 K and 5.2 GPa and its critical point to be at 6000more » K and 8.8 GPa. The present Hugoniot calculations suggest that the liquid-liquid phase transition may be detected by performing a shock experiment with initial density of approximately 0.15 gm/cm{sup 3}.« less

Preparation of hydrophobic organic aeorgels

DOEpatents

Baumann, Theodore F.; Satcher, Jr., Joe H.; Gash, Alexander E.

2007-11-06

Synthetic methods for the preparation of hydrophobic organics aerogels. One method involves the sol-gel polymerization of 1,3-dimethoxybenzene or 1,3,5-trimethoxybenzene with formaldehyde in non-aqueous solvents. Using a procedure analogous to the preparation of resorcinol-formaldehyde (RF) aerogels, this approach generates wet gels that can be dried using either supercritical solvent extraction to generate the new organic aerogels or air dried to produce an xerogel. Other methods involve the sol-gel polymerization of 1,3,5 trihydroxy benzene (phloroglucinol) or 1,3 dihydroxy benzene (resorcinol) and various aldehydes in non-aqueous solvents. These methods use a procedure analogous to the one-step base and two-step base/acid catalyzed polycondensation of phloroglucinol and formaldehyde, but the base catalyst used is triethylamine. These methods can be applied to a variety of other sol-gel precursors and solvent systems. These hydrophobic organics aerogels have numerous application potentials in the field of material absorbers and water-proof insulation.

Preparation of hydrophobic organic aeorgels

DOEpatents

Baumann, Theodore F.; Satcher, Jr., Joe H.; Gash, Alexander E.

2004-10-19

Synthetic methods for the preparation of hydrophobic organics aerogels. One method involves the sol-gel polymerization of 1,3-dimethoxybenzene or 1,3,5-trimethoxybenzene with formaldehyde in non-aqueous solvents. Using a procedure analogous to the preparation of resorcinol-formaldehyde (RF) aerogels, this approach generates wet gels that can be dried using either supercritical solvent extraction to generate the new organic aerogels or air dried to produce an xerogel. Other methods involve the sol-gel polymerization of 1,3,5 trihydroxy benzene (phloroglucinol) or 1,3 dihydroxy benzene (resorcinol) and various aldehydes in non-aqueous solvents. These methods use a procedure analogous to the one-step base and two-step base/acid catalyzed polycondensation of phloroglucinol and formaldehyde, but the base catalyst used is triethylamine. These methods can be applied to a variety of other sol-gel precursors and solvent systems. These hydrophobic organics aerogels have numerous application potentials in the field of material absorbers and water-proof insulation.

Phenolic compounds can delay the oxidation of polyunsaturated fatty acids and the growth of Listeria monocytogenes: structure-activity relationships.

PubMed

Pernin, Aurélia; Dubois-Brissonnet, Florence; Roux, Stéphanie; Masson, Marine; Bosc, Véronique; Maillard, Marie-Noëlle

2018-04-20

Phenolic compounds present a potential solution to ensuring food quality and safety. Indeed, they can limit oxidation reactions and bacterial growth in food products. Although their antioxidant mechanisms of action are well known, their antibacterial ones are less well understood, especially in light of their chemical structures. The aim of this study was to first quantify both aspects of a series of natural phenolic compounds and then link these activities to their chemical structure. We evaluated antioxidant activity by measuring the capacity of phenolic compounds to delay free linoleic acid oxidation caused by the action of a hydrophilic azo-radical initiator (AAPH). We evaluated antibacterial activity by measuring the growth inhibition of Listeria monocytogenes and determining the non-inhibitory and minimum inhibitory concentrations for each compound. Compounds with ortho-diphenolic structures were the best antioxidants, whereas those belonging to the simple phenol category were the best antibacterial compounds. The physico-chemical properties of the compounds influenced both activities, but not in the same way. The chemical environment of the phenolic group and the presence of delocalization structures are the most important parameters for antioxidant activity, whereas the partition coefficient logP is one of the most important factors involved in antibacterial activity. This article is protected by copyright. All rights reserved.

A review of molecular mechanisms of the anti-leukemic effects of phenolic compounds in honey.

PubMed

Abubakar, Murtala B; Abdullah, Wan Zaidah; Sulaiman, Siti Amrah; Suen, Ang Boon

2012-11-15

Hematologic malignancies constitute about 9% of all new cases of cancers as reported via the GLOBOCAN series by International Agency for Research on Cancer (IARC) in 2008. So far, the conventional therapeutic and surgical approaches to cancer therapy have not been able to curtail the rising incidence of cancers, including hematological malignancies, worldwide. The last decade has witnessed great research interest in biological activities of phenolic compounds that include anticancer, anti-oxidation and anti-inflammation, among other things. A large number of anticancer agents combat cancer through cell cycle arrest, induction of apoptosis and differentiation, as well as through inhibition of cell growth and proliferation, or a combination of two or more of these mechanisms. Various phenolic compounds from different sources have been reported to be promising anticancer agents by acting through one of these mechanisms. Honey, which has a long history of human consumption both for medicinal and nutritional uses, contains a variety of phenolic compounds such as flavonoids, phenolic acids, coumarins and tannins. This paper presents a review on the molecular mechanisms of the anti-leukemic activity of various phenolic compounds on cell cycle, cell growth and proliferation and apoptosis, and it advocates that more studies should be conducted to determine the potential role of honey in both chemoprevention and chemotherapy in leukemia.

Importance of phenols structure on their activity as antinitrosating agents: A kinetic study

PubMed Central

Pessêgo, Márcia; Rosa da Costa, Ana M; Moreira, José A.

2011-01-01

Objective: Nitrosative deamination of DNA bases induced by reaction with reactive nitrogen species (RNS) has been pointed out as a probable cause of mutagenesis. (Poly)phenols, present in many food items from the Mediterranean diet, are believed to possess antinitrosating properties due to their RNS scavenging ability, which seems to be related to their structure. It has been suggested that phenolic compounds will react with the above-mentioned species more rapidly than most amino compounds, thus preventing direct nitrosation of the DNA bases and their transnitrosation from endogenous N-nitroso compounds, or most likely from the transient N-nitrosocompounds formed in vivo. Materials and Methods: In order to prove that assumption, a kinetic study of the nitroso group transfer from a N-methyl-N-nitrosobenzenesulfonamide (N-methyl-N-nitroso-4-methylbenzenesulfonamide, MeNMBS) to the DNA bases bearing an amine group and to a series of phenols was carried out. In the transnitrosation of phenols, the formation of nitrosophenol was monitored by Ultraviolet (UV) / Visible spectroscopy, and in the reactions of the DNA bases, the consumption of MeNMBS was followed by high performance liquid chromatography (HPLC). Results: The results obtained point to the transnitrosation of DNA bases being negligible, as well as that of phenols bearing electron-withdrawing groups. Phenols with methoxy substituents in positions 2, 4, and / or 6, although they seemed to react, did not afford the expected product. Phenols with electron-releasing substituents, unless these blocked the oxygen atom, reacted with our model compound at an appreciable rate. O-nitrosation of the phenolate ion followed by rearrangement of the C-nitrosophenol seemed to be involved. Conclusion: This study provided evidence that the above compounds might actually act as antinitrosating agents in vivo. PMID:21430963

Molecular complexes of alprazolam with carboxylic acids, boric acid, boronic acids, and phenols. Evaluation of supramolecular heterosynthons mediated by a triazole ring.

PubMed

Varughese, Sunil; Azim, Yasser; Desiraju, Gautam R

2010-09-01

A series of molecular complexes, both co-crystals and salts, of a triazole drug-alprazolam-with carboxylic acids, boric acid, boronic acids, and phenols have been analyzed with respect to heterosynthons present in the crystal structures. In all cases, the triazole ring behaves as an efficient hydrogen bond acceptor with the acidic coformers. The hydrogen bond patterns exhibited with aromatic carboxylic acids were found to depend on the nature and position of the substituents. Being a strong acid, 2,6-dihydroxybenzoic acid forms a salt with alprazolam. With aliphatic dicarboxylic acids alprazolam forms hydrates and the water molecules play a central role in synthon formation and crystal packing. The triazole ring makes two distinct heterosynthons in the molecular complex with boric acid. Boronic acids and phenols form consistent hydrogen bond patterns, and these are seemingly independent of the substitutional effects. Boronic acids form noncentrosymmetric cyclic synthons, while phenols form O--H...N hydrogen bonds with the triazole ring.

Polymerization of phenol by using discharged plasma under hydrothermal state

NASA Astrophysics Data System (ADS)

Mitsugi, M.; Yoshida, A.; Watanabe, H.; Kiyan, T.; Takade, M.; Miyaji, K.; Namihira, T.; Kuwahara, Y.; Akiyama, H.; Hara, M.; Sasaki, M.; Goto, M.

2010-03-01

Supercritical fluid with plasma is a type of green processing media because this technique does not use catalyst and toxic solvents. In this study, we carried out experiments of organic materials in the presence of discharged plasma in sub- and supercritical water to evaluate the possibility for new reactions. For this purpose, we used SUS316 reactor that generates plasma at temperature and pressure up to 573K and 30MPa, respectively. 100 mmol/L aqueous phenol solution was used as starting material. The reactions were carried out at temperature of 523K and under pressure of 25MPa. After a series of reactions, water-soluble, water-insoluble (oily products), solid residue and gaseous product were obtained. For the analysis of these products, HPLC, GC-MS, TOC, GC-TCD and TOF-MS were used. The highest phenol conversion was 16.96% obtained at 523K, 25MPa and with 4000 times discharged plasma. Polymerized phenol was obtained as a product.

Carbonic anhydrase inhibitors: guaiacol and catechol derivatives effectively inhibit certain human carbonic anhydrase isoenzymes (hCA I, II, IX and XII).

PubMed

Scozzafava, Andrea; Passaponti, Maurizio; Supuran, Claudiu T; Gülçin, İlhami

2015-01-01

Carbonic anhydrases (CAs) are widespread metalloenzymes in higher vertebrates including humans. A series of phenolic compounds, including guaiacol, 4-methylguaiacol, 4-propylguaiacol, eugenol, isoeugenol, vanillin, syringaldehyde, catechol, 3-methyl catechol, 4-methyl catechol and 3-methoxy catechol were investigated for their inhibition of all the catalytically active mammalian isozymes of the Zn(2+)-containing CA (EC 4.2.1.1). All the phenolic compounds effectively inhibited human carbonic anhydrase isoenzymes (hCA I, II, IX and XII), with Kis in the range of 2.20-515.98 μM. The various isozymes showed diverse inhibition profiles. Among the tested phenolic derivatives, compounds 4-methyl catechol and 3-methoxy catechol showed potent activity as inhibitors of the tumour-associated transmembrane isoforms (hCA IX and XII) in the submicromolar range, with high selectivity. The results obtained from this research may lead to the design of more effective carbonic anhydrase isoenzyme inhibitors (CAIs) based on such phenolic compound scaffolds.

Growth Inhibition and DNA Damage Induced by X-Phenols in Yeast: A Quantitative Structure–Activity Relationship Study

PubMed Central

2017-01-01

Phenolic compounds and their derivatives are ubiquitous constituents of numerous synthetic and natural chemicals that exist in the environment. Their toxicity is mostly attributed to their hydrophobicity and/or the formation of free radicals. In a continuation of the study of phenolic toxicity in a systematic manner, we have examined the biological responses of Saccharomyces cerevisiae to a series of mostly monosubstituted phenols utilizing a quantitative structure–activity relationship (QSAR) approach. The biological end points included a growth assay that determines the levels of growth inhibition induced by the phenols as well as a yeast deletion (DEL) assay that assesses the ability of X-phenols to induce DNA damage or DNA breaks. The QSAR analysis of cell growth patterns determined by IC50 and IC80 values indicates that toxicity is delineated by a hydrophobic, parabolic model. The DEL assay was then utilized to detect genomic deletions in yeast. The increase in the genotoxicity was enhanced by the electrophilicity of the phenolic substituents that were strong electron donors as well as by minimal hydrophobicity. The electrophilicities are represented by Brown’s sigma plus values that are a variant of the Hammett sigma constants. A few mutant strains of genes involved in DNA repair were separately exposed to 2,6-di-tert-butyl-4-methyl-phenol (BHT) and butylated hydroxy anisole (BHA). They were subsequently screened for growth phenotypes. BHA-induced growth defects in most of the DNA repair null mutant strains, whereas BHT was unresponsive. PMID:29302629

Divergent synthesis of bioactive resorcinols isolated from the fruiting bodies of Hericium erinaceum: total syntheses of hericenones A, B, and I, hericenols B-D, and erinacerins A and B.

PubMed

Kobayashi, Shoji; Tamanoi, Hidetsugu; Hasegawa, Yuichi; Segawa, Yusuke; Masuyama, Araki

2014-06-06

Total syntheses of 5'- and 7'-oxidized geranyl resorcylates isolated from the fruiting bodies of Hericium erinaceum and the submerged cultures of a Stereum species were achieved. Our synthesis features derivatization of a suitably functionalized 5'-oxidized geranyl phthalide as a common intermediate, which was obtained by Stille coupling between the phthalide core and the side chain, into a series of natural products by divergent functional group manipulations. The crucial C5'-oxygen functionality was installed at the initial stage by alkylation by an α-cyano ethoxyethyl ether. From a common synthetic intermediate, eight total syntheses including hericenones A, B, and I, hericenols B-D, and erinacerins A and B were achieved (hericenol B and erinacerin B were synthesized as racemates). The structure of hericenone B established in the isolation paper was unambiguously revised as the carbonyl regioisomer at the lactam moiety.

On the synthesis and structure of resorcinol-formaldehyde polymeric networks – Precursors to 3D-carbon macroassemblies

DOE PAGES

Lewicki, James P.; Fox, Christina A.; Worsley, Marcus A.

2015-05-15

With the new impetus towards the development of hierarchical graphene and CNT macro-assemblies for application in fields such as advanced energy storage, catalysis and electronics; there is much renewed interest in organic carbon-based sol–gel processes as a synthetically convenient and versatile means of forming three dimensional, covalently bonded organic/inorganic networks. Such matrices can act as highly effective precursors, scaffolds or molecular ‘glues’ for the assembly of a wide variety of functional carbon macro-assemblies. However, despite the utility and broad use of organic sol–gel processes – such as the ubiquitous resorcinol-formaldehyde (RF) reaction, there are details of the reaction chemistries ofmore » these important sol–gel processes that remain poorly understood at present. It is therefore both timely and necessary to examine these reactions in more detail using modern analytical techniques in order to gain a more rigorous understanding of the mechanisms by which these organic networks form. The goal of such studies is to obtain improved and rational control over the organic network structure, in order to better direct and tailor the architecture of the final inorganic carbon matrix. In this study we have investigated in detail, the mechanism of the organic sol–gel network forming reaction of resorcinol and formaldehyde from a structural and kinetic standpoint, by using a combination of real-time high field solution state nuclear magnetic resonance (NMR), low field NMR relaxometry and differential scanning calorimetry (DSC). These investigations have allowed us to track the network formation processes in real-time, gain both detailed structural information on the mechanisms of the RF sol–gel process and a quantitative assessment of the kinetics of the global network formation process. Here, it has been shown that the mechanism, by which the RF organic network forms, proceeds via an initial exothermic step correlated to the formation of a free aromatic aldehyde. The network growth reaction then proceeds in a statistical manner following a first order Arrhenius type kinetic relationship – characteristic of a typical thermoset network poly-condensation process. Finally, despite the relative complexity and ill-defined nature of the formaldehyde staring material, the final network structure is to a large extent, governed by the substitution pattern of the resorcinol molecule.« less

The Electrical Properties for Phenolic Isocyanate-Modified Bisphenol-Based Epoxy Resins Comprising Benzoate Group.

PubMed

Lee, Eun Yong; Chae, Il Seok; Park, Dongkyung; Suh, Hongsuk; Kang, Sang Wook

2016-03-01

Epoxy resin has been required to have a low dielectric constant (D(k)), low dissipation factor (Df), low coefficient of thermal expansion (CTE), low water absorption, high mechanical, and high adhesion properties for various applications. A series of novel phenolic isocyanate-modified bisphenol-based epoxy resins comprising benzoate group were prepared for practical electronic packaging applications. The developed epoxy resins showed highly reduced dielectric constants (D(k)-3.00 at 1 GHz) and low dissipation values (Df-0.014 at 1 GHz) as well as enhanced thermal properties.

Pressure Venting Tests of Phenolic Impregnated Carbon Ablator (PICA)

NASA Technical Reports Server (NTRS)

Blosser, Max L.; Knutson, Jeffrey R.

2015-01-01

A series of tests was devised to investigate the pressure venting behavior of one of the candidate ablators for the Orion capsule heat shield. Three different specimens of phenolic impregnated carbon ablator (PICA) were instrumented with internal pressure taps and subjected to rapid pressure changes from near vacuum to one atmosphere and simulated Orion ascent pressure histories. The specimens vented rapidly to ambient pressure and sustained no detectable damage during testing. Peak pressure differences through the thickness of a 3-inch-thick specimen were less than 1 psi during a simulated ascent pressure history.

Pathways to Mesoporous Resin/Carbon Thin Films with Alternating Gyroid Morphology

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

Zhang, Qi; Matsuoka, Fumiaki; Suh, Hyo Seon

Three-dimensional (3D) mesoporous thin films with sub-100 nm periodic lattices are of increasing interest as templates for a number of nanotechnology applications, yet are hard to achieve with conventional top-down fabrication methods. Block copolymer self-assembly derived mesoscale structures provide a toolbox for such 3D template formation. In this work, single (alternating) gyroidal and double gyroidal mesoporous thin-film structures are achieved via solvent vapor annealing assisted co-assembly of poly(isoprene-block-styrene-block-ethylene oxide) (PI-b-PS-b-PEO, ISO) and resorcinol/phenol formaldehyde resols. In particular, the alternating gyroid thin-film morphology is highly desirable for potential template backfilling processes as a result of the large pore volume fraction. Inmore » situ grazing-incidence small-angle X-ray scattering during solvent annealing is employed as a tool to elucidate and navigate the pathway complexity of the structure formation processes. The resulting network structures are resistant to high temperatures provided an inert atmosphere. The thin films have tunable hydrophilicity from pyrolysis at different temperatures, while pore sizes can be tailored by varying ISO molar mass. A transfer technique between substrates is demonstrated for alternating gyroidal mesoporous thin films, circumventing the need to re-optimize film formation protocols for different substrates. Increased conductivity after pyrolysis at high temperatures demonstrates that these gyroidal mesoporous resin/carbon thin films have potential as functional 3D templates for a number of nanomaterials applications.« less

A Review of Molecular Mechanisms of the Anti-Leukemic Effects of Phenolic Compounds in Honey

PubMed Central

Abubakar, Murtala B.; Abdullah, Wan Zaidah; Sulaiman, Siti Amrah; Suen, Ang Boon

2012-01-01

Hematologic malignancies constitute about 9% of all new cases of cancers as reported via the GLOBOCAN series by International Agency for Research on Cancer (IARC) in 2008. So far, the conventional therapeutic and surgical approaches to cancer therapy have not been able to curtail the rising incidence of cancers, including hematological malignancies, worldwide. The last decade has witnessed great research interest in biological activities of phenolic compounds that include anticancer, anti-oxidation and anti-inflammation, among other things. A large number of anticancer agents combat cancer through cell cycle arrest, induction of apoptosis and differentiation, as well as through inhibition of cell growth and proliferation, or a combination of two or more of these mechanisms. Various phenolic compounds from different sources have been reported to be promising anticancer agents by acting through one of these mechanisms. Honey, which has a long history of human consumption both for medicinal and nutritional uses, contains a variety of phenolic compounds such as flavonoids, phenolic acids, coumarins and tannins. This paper presents a review on the molecular mechanisms of the anti-leukemic activity of various phenolic compounds on cell cycle, cell growth and proliferation and apoptosis, and it advocates that more studies should be conducted to determine the potential role of honey in both chemoprevention and chemotherapy in leukemia. PMID:23203111

Glycosylation of phenolic compounds by the site-mutated β-galactosidase from Lactobacillus bulgaricus L3.

PubMed

Lu, Lili; Xu, Lijuan; Guo, Yuchuan; Zhang, Dayu; Qi, Tingting; Jin, Lan; Gu, Guofeng; Xu, Li; Xiao, Min

2015-01-01

β-Galactosidases can transfer the galactosyl from lactose or galactoside donors to various acceptors and thus are especially useful for the synthesis of important glycosides. However, these enzymes have limitations in the glycosylation of phenolic compounds that have many physiological functions. In this work, the β-galactosidase from Lactobacillus bulgaricus L3 was subjected to site-saturation mutagenesis at the W980 residue. The recombinant pET-21b plasmid carrying the enzyme gene was used as the template for mutation. The mutant plasmids were transformed into Escherichia coli cells for screening. One recombinant mutant, W980F, exhibited increased yield of glycoside when using hydroquinone as the screening acceptor. The enzyme was purified and the effects of the mutation on enzyme properties were determined in detail. It showed improved transglycosylation activity on novel phenolic acceptors besides hydroquinone. The yields of the glycosides produced from phenol, hydroquinone, and catechol were increased by 7.6% to 53.1%. Moreover, it generated 32.3% glycosides from the pyrogallol that could not be glycosylated by the wild-type enzyme. Chemical structures of these glycoside products were further determined by MS and NMR analysis. Thus, a series of novel phenolic galactosides were achieved by β-galactosidase for the first time. This was a breakthrough in the enzymatic galactosylation of the challenging phenolic compounds of great values.

Metabolic and Microbial Modulation of the Large Intestine Ecosystem by Non-Absorbed Diet Phenolic Compounds: A Review.

PubMed

Mosele, Juana I; Macià, Alba; Motilva, Maria-José

2015-09-18

Phenolic compounds represent a diverse group of phytochemicals whose intake is associated with a wide spectrum of health benefits. As consequence of their low bioavailability, most of them reach the large intestine where, mediated by the action of local microbiota, a series of related microbial metabolites are accumulated. In the present review, gut microbial transformations of non-absorbed phenolic compounds are summarized. Several studies have reached a general consensus that unbalanced diets are associated with undesirable changes in gut metabolism that could be detrimental to intestinal health. In terms of explaining the possible effects of non-absorbed phenolic compounds, we have also gathered information regarded their influence on the local metabolism. For this purpose, a number of issues are discussed. Firstly, we consider the possible implications of phenolic compounds in the metabolism of colonic products, such as short chain fatty acids (SCFA), sterols (cholesterol and bile acids), and microbial products of non-absorbed proteins. Due to their being recognized as affective antioxidant and anti-inflammatory agents, the ability of phenolic compounds to counteract or suppress pro-oxidant and/or pro-inflammatory responses, triggered by bowel diseases, is also presented. The modulation of gut microbiota through dietetic maneuvers including phenolic compounds is also commented on. Although the available data seems to assume positive effects in terms of gut health protection, it is still insufficient for solid conclusions to be extracted, basically due to the lack of human trials to confirm the results obtained by the in vitro and animal studies. We consider that more emphasis should be focused on the study of phenolic compounds, particularly in their microbial metabolites, and their power to influence different aspects of gut health.

Bacterial metabolism of aromatic compounds and a complex hazardous waste under anaerobic conditions

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

O'Connor, O.A.

1992-01-01

The biological fate of organic chemicals in the environment depends upon a variety of physical/chemical factors. In the absence of molecular oxygen, the importance of terminal electron acceptors has been often overlooked. Since anaerobic microbial consortia are dependent upon the availability of particular electron acceptors, these conditions can play an important role in influencing the fate of environmental pollutants. In this research, different electron acceptors were evaluated for their effects on the biodegradation of environmental toxicants. Two anaerobic bioassays, the Biochemical Methane Potential (BMP) and the Anaerobic Toxicity Assay (ATA), were used to evaluate a series of phthalic acid estersmore » (PAEs), substituted phenols and a landfill leachate, for their methanogenic biodegradability and toxicity. Many of the PAEs and phenols could be stoichiometrically mineralized. In addition, the landfill leachate was found to be inhibitory at concentrations greater than 10%, and partially mineralized in approximately 50 weeks. Based upon these assays, 6 different functional groups and their isomers were evaluated for their effect on the biodegradability and toxicity of phenol under methanogenic and denitrifying conditions. These results indicated that nitro- and chloro-substituted phenols were persistent under denitrifying conditions. Under methanogenic conditions, these compounds were metabolized to a more reduced intermediate with less toxicity. Conversely, amino-substituted phenols were not readily mineralized under methanogenic conditions, but were metabolized after minimal lag under denitrifying conditions. From active denitrifying phenol degrading cultures, a pure culture was obtained which could grow on phenol and on a variety of other alkyl-substituted aromatic compounds. Additional studies have tentatively identified several alicyclic metabolites including cyclohexanol, 2-cyclohexene-1-ol, cyclohexanone and 2-cyclohexene-1-one from phenol catabolism.« less

Various effects of the photosystem II--inhibiting herbicides on 5-n-alkylresorcinol accumulation in rye seedlings.

PubMed

Magnucka, Elżbieta G; Pietr, Stanisław J; Kozubek, Arkadiusz; Zarnowski, Robert

2014-11-01

The effect of three PSII-inhibiting herbicides, lenacil, linuron, and pyrazon, on the accumulation of 5-n-alkylresorcinols in rye seedlings (Secale cereale L.) grown under various light and thermal conditions was studied. All used chemicals increased resorcinolic lipid content in both green and etiolated plants grown at 29 °C. At 22 °C pyrazon and lenacil decreased the content of alkylresorcinols in plants kept in the darkness and increased their amount in the light-grown seedlings. In turn, level of resorcinolic lipids was decreased by linuron in both etiolated and green plants. At the lowest tested temperature lenacil enhanced production of alkylresorcinols only in etiolated rye seedlings, whereas the light-independent stimulatory action of pyrazon on alkylresorcinol accumulation in rye grown at 15 °C was observed. Additionally, only the latter did not exert a negative effect on rye seedling growth under any of tested conditions. Compared with respective controls, the herbicides used also markedly modified the qualitative pattern of resorcinolic homologs. Interestingly, the observed changes generally favored the enhanced antifungal activity of these compounds. Our study provides novel information on the influence of PSII inhibitors on alkylresorcinol metabolism in rye seedlings. The unquestionable achievement of this work is the observation that low dose of pyrazon mainly stimulated both growth and alkylresorcinol synthesis in rye seedlings, a non-target plant. Moreover, our experimental work showed unambiguously that the observed pyrazon-driven accumulation and homolog pattern modification of alkylresorcinols dramatically improved the resistance of winter rye to infections caused by Rhizoctonia cerealis. Copyright © 2014 Elsevier Inc. All rights reserved.

ELECTROCHEMICALLY DEPOSITED POLYMER-COATED GOLD ELECTRODES SELECTIVE FOR 2,4-DICHLOROPHENOXYACETIC ACID

EPA Science Inventory

Electropolymerized membranes on gold electrodes doped with 2,4-dichlorophenoxyacetic acid (2,4-D) were prepared from a solution containing resorcinol, o-phenylenediamine and 2,4-D. Fourier Transform Infrared (FTIR) spectroscopy was used to evaluate the incorporation and interact...

Aquagel electrode separator for use in batteries and supercapacitors

DOEpatents

Mayer, Steven T.; Kaschmitter, James L.; Pekala, Richard W.

1995-01-01

An electrode separator for electrochemical energy storage devices, such as a high energy density capacitor incorporating a variety of carbon foam electrodes. The separator is derived from an aquagel of resorcinol-formaldehyde and related polymers and containing ionically conducting electrolyte in the pores thereof.

Structural features of resorcinol-formaldehyde resin chars and interfacial behavior of water co-adsorbed with low-molecular weight organics

NASA Astrophysics Data System (ADS)

Gun'ko, Vladimir M.; Bogatyrov, Viktor M.; Turov, Vladimir V.; Leboda, Roman; Skubiszewska-Zięba, Jadwiga; Urubkov, Iliya V.

2013-10-01

Products of resorcinol-formaldehyde resin carbonization (chars) are characterized by different morphology (particle shape and sizes) and texture (specific surface area, pore volume and pore size distribution) depending on water content during resin polymerization. At a low amount of water (Cw = 37.8 wt.%) during synthesis resulting in strongly cross-linked polymers, carbonization gives nonporous particles. An increase in the water content to 62.7 wt.% results in a nano/mesoporous char, but if Cw = 73.3 wt.%, a char is purely nanoporous. Despite these textural differences, the Raman spectra of all the chars are similar because of the similarity in the structure of their carbon sheets with a significant contribution of sp3 C atoms. However, the difference in the spatial organization of the carbon sheet stacks in the particles results in the significant differences in the textural and morphological characteristics and in the adsorption properties of chars with respect to water, methane, benzene, hydrogen, methylene chloride, and dimethylsulfoxide.

Gas Generation Testing of Spherical Resorcinol-Formaldehyde (sRF) Resin

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

Colburn, Heather A.; Bryan, Samuel A.; Camaioni, Donald M.

This report describes gas generation testing of the spherical resorcinol-formaldehyde (sRF) resin that was conducted to support the technology maturation of the LAWPS facility. The current safety basis for the LAWPS facility is based primarily on two studies that had limited or inconclusive data sets. The two studies indicated a 40% increase in hydrogen generation rate of water (as predicted by the Hu model) with sRF resin over water alone. However, the previous studies did not test the range of conditions (process fluids and temperatures) that are expected in the LAWPS facility. Additionally, the previous studies did not obtain replicatemore » test results or comparable liquid-only control samples. All of the testing described in this report, conducted with water, 0.45M nitric acid, and waste simulants with and without sRF resin, returned hydrogen generation rates that are within the current safety basis for the facility of 1.4 times the Hu model output for water.« less

Resorcinol-, catechol- and saligenin-based bronchodilating β2-agonists as inhibitors of human cholinesterase activity.

PubMed

Bosak, Anita; Knežević, Anamarija; Gazić Smilović, Ivana; Šinko, Goran; Kovarik, Zrinka

2017-12-01

We investigated the influence of bronchodilating β2-agonists on the activity of human acetylcholinesterase (AChE) and usual, atypical and fluoride-resistant butyrylcholinesterase (BChE). We determined the inhibition potency of racemate and enantiomers of fenoterol as a resorcinol derivative, isoetharine and epinephrine as catechol derivatives and salbutamol and salmeterol as saligenin derivatives. All of the tested compounds reversibly inhibited cholinesterases with K i constants ranging from 9.4 μM to 6.4 mM and had the highest inhibition potency towards usual BChE, but generally none of the cholinesterases displayed any stereoselectivity. Kinetic and docking results revealed that the inhibition potency of the studied compounds could be related to the size of the hydroxyaminoethyl chain on the benzene ring. The additional π-π interaction of salmeterol's benzene ring and Trp286 and hydrogen bond with His447 probably enhanced inhibition by salmeterol which was singled out as the most potent inhibitor of all the cholinesterases.

Modification of glassy carbon electrode with poly(hydroxynaphthol blue)/multi-walled carbon nanotubes composite and construction a new voltammetric sensor for the simultaneous determination of hydroquinone, catechol, and resorcinol

NASA Astrophysics Data System (ADS)

Daneshinejad, Hassan; Arab Chamjangali, Mansour; Goudarzi, Nasser; Hossain Amin, Amir

2018-03-01

A novel voltammetric sensor is developed based on a poly(hydroxynaphthol blue)/multi-walled carbon nanotubes-modified glassy carbon electrode for the simultaneous determination of the dihydroxybenzene isomers hydroquinone (HQ), catechol (CC), and resorcinol (RS). The preparation and basic electrochemical performance of the sensor are investigated in details. The electrochemical behavior of the dihydroxybenzene isomers at the sensor is studied by the cyclic and differential pulse voltammetric techniques. The results obtained show that this new electrochemical sensor exhibits an excellent electro-catalytic activity towards oxidation of the three isomers. The mechanism of this electro-catalytic activity is discussed. Using the optimum parameters, limit of detection obtained 0.24, 0.24, and 0.26 μmol L-1 for HQ, CC, and RS, respectively. The modified electrode is also successfully applied to the simultaneous determination of dihydroxybenzene in water samples.

Synthesis and characterization of electrical conducting porous carbon structures based on resorcinol-formaldehyde

NASA Astrophysics Data System (ADS)

Najeh, I.; Ben Mansour, N.; Mbarki, M.; Houas, A.; Nogier, J. Ph.; El Mir, L.

2009-10-01

Electrical conducting carbon (ECC) porous structures were explored by changing the pyrolysis temperature of organic xerogel compounds prepared by sol-gel method from resorcinol-formaldehyde (RF) mixtures in acetone using picric acid as catalyst. The effect of this preparation parameter on the structural and electrical properties of the obtained ECCs was studied. The analysis of the obtained results revealed that the polymeric insulating xerogel phase was transformed progressively with pyrolysis temperature into carbon conducting phase; this means the formation of long continuous conducting path for charge carriers to move inside the structure with thermal treatment and the samples exhibited tangible percolation behaviour where the percolation threshold can be determined by pyrolysis temperature. The temperature-dependent conductivity of the obtained ECC structures shows a semi-conducting behaviour and the I( V) characteristics present a negative differential resistance. The results obtained from STM micrographs revealed that the obtained ECC structures consist of porous electrical conducting carbon materials.

Evaluations of Mechanisms for Pu Uptake and Retention within Spherical Resorcinol-Formaldehyde Resin Columns

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

Delegard, Calvin H.; Levitskaia, Tatiana G.; Fiskum, Sandra K.

The unexpected uptake and retention of plutonium (Pu) onto columns containing spherical resorcinol-formaldehyde (sRF) resin during ion exchange testing of Cs (Cs) removal from alkaline tank waste was observed in experiments at both the Pacific Northwest National Laboratory (PNNL) and the Savannah River National Laboratory (SRNL). These observations have raised concern regarding the criticality safety of the Cs removal unit operation within the low-activity waste pretreatment system (LAWPS). Accordingly, studies have been initiated at Washington River Protection Solutions (WRPS), who manages the operations of the Hanford Site tank farms, including the LAWPS, PNNL, and elsewhere to investigate these findings. Asmore » part of these efforts, PNNL has prepared the present report to summarize the laboratory testing observations, evaluate these phenomena in light of published and unpublished technical information, and outline future laboratory testing, as deemed appropriate based on the literature studies, with the goal to elucidate the mechanisms for the observed Pu uptake and retention.« less

Electrophoresis-chemiluminescence detection of phenols catalyzed by hemin.

PubMed

Shu, Lu; Zhu, Jinkun; Wang, Qingjiang; He, Pingang; Fang, Yuzhi

2014-09-01

Based on the catalytic activity of hemin, an efficient biocatalyst, an indirect capillary electrophoresis-chemiluminescence (CE-CL) detection method for phenols using a hemin-luminol-hydrogen peroxide system was developed. Through a series of static injection experiments, hemin was found to perform best in a neutral solution rather than an acidic or alkaline medium. Although halide ions such as Br(-) and F(-) could further enhance the CL signal catalyzed by hemin, it is difficult to apply these conditions to this CE-CL detection system because of the self-polymerization of hemin, as it hinders the CE process. The addition of concentrated ammonium hydroxide to an aqueous/dimethyl sulfoxide solution of hemin-luminol afforded a stable CE-CL baseline. The indirect CE-CL detection of five phenols using this method gave the following limits of detections: 4.8 × 10(-8) mol/L (o-sec-butylphenol), 4.9 × 10(-8) mol/L (o-cresol), 5.4 × 10(-8) mol/L (m-cresol), 5.3 × 10(-8) mol/L (2,4-dichlorophenol) and 7.1 × 10(-8) mol/L (phenol). Copyright © 2013 John Wiley & Sons, Ltd.

Methylation patterns of aquatic humic substances determined by 13C NMR spectroscopy

USGS Publications Warehouse

Thorn, K.A.; Steelink, C.; Wershaw, R. L.

1987-01-01

13C NMR spectroscopy is used to examine the hydroxyl group functionality of a series of humic and fulvic acids from different aquatic environments. Samples first are methylated with 13C-labeled diazomethane. The NMR spectra of the diazomethylated samples allow one to distinguish between methyl esters of carboxylic acids, methyl ethers of phenolic hydroxyls, and methyl ethers of phenolic hydroxyls adjacent to two substituents. Samples are then permethylated with 13C-labeled methyl iodide/NaH. 13C NMR spectra of permethylated samples show that a significant fraction of the hydroxyl groups is not methylated with diazomethane alone. In these spectra methyl ethers of carbohydrate and aliphatic hydroxyls overlap with methyl ethers of phenolic hydroxyls. Side reactions of the methyltion procedure including carbon methylation in the CH3I/NaH procedure, are also examined. Humic and fulvic acids from bog, swamp, groundwater, and lake waters showssome differences in their distribution of hydroxyl groups, mainly in the concentrations of phenolic hydroxyls, which may be attributed to their different biogeochemical origins. ?? 1987.

A review of catalytic hydrodeoxygenation of lignin-derived phenols from biomass pyrolysis.

PubMed

Bu, Quan; Lei, Hanwu; Zacher, Alan H; Wang, Lu; Ren, Shoujie; Liang, Jing; Wei, Yi; Liu, Yupeng; Tang, Juming; Zhang, Qin; Ruan, Roger

2012-11-01

Catalytic hydrodeoxygenation (HDO) of lignin-derived phenols which are the lowest reactive chemical compounds in biomass pyrolysis oils has been reviewed. The hydrodeoxygenation (HDO) catalysts have been discussed including traditional HDO catalysts such as CoMo/Al(2)O(3) and NiMo/Al(2)O(3) catalysts and transition metal catalysts (noble metals). The mechanism of HDO of lignin-derived phenols was analyzed on the basis of different model compounds. The kinetics of HDO of different lignin-derived model compounds has been investigated. The diversity of bio-oils leads to the complexities of HDO kinetics. The techno-economic analysis indicates that a series of major technical and economical efforts still have to be investigated in details before scaling up the HDO of lignin-derived phenols in existed refinery infrastructure. Examples of future investigation of HDO include significant challenges of improving catalysts and optimum operation conditions, further understanding of kinetics of complex bio-oils, and the availability of sustainable and cost-effective hydrogen source. Copyright © 2012 Elsevier Ltd. All rights reserved.

Some phenolic compounds of extracts obtained from Origanum species growing in Turkey.

PubMed

Ozkan, Gülcan; Ozcan, Mehmet Musa

2014-08-01

Caffeic acid, rosmarinic acid, rutin, apigenin 7-O-glucoside, apigenin, and acesetin were the main phenolic compounds of Origanum onites extracts in all applications. While acesetin contents ranged from 133.59 mg/100 g (U1) to 437.25 mg/100 g (S3), rosmarinic acid changed between 215.94 mg/100 g (U4) and 1120.56 mg/100 g (S2) in Origanum vulgare L. subsp. hirtum (Link) Ietsw. Both rosmarinic acid and acesetin were not found in U5 application. Only caffeic acid (19.39 mg/100 g) was found in U5 application. Rosmarinic acid contents of O. onites extract changed between 158.62 mg/100 g (U5) and 799.87 mg/100 g (S2). Generally, dominant phenolic compound of Origanum extracts was rosmarinic acid compared with other extracts. In addition, methanol:water:acetic acid mixture (S2) (95:4.5:0.5) was found as the best application. Phenolic contents of extracts obtained with U series mixtures were found low.

A Quantum Chemical and Statistical Study of Phenolic Schiff Bases with Antioxidant Activity against DPPH Free Radical

PubMed Central

Anouar, El Hassane

2014-01-01

Phenolic Schiff bases are known as powerful antioxidants. To select the electronic, 2D and 3D descriptors responsible for the free radical scavenging ability of a series of 30 phenolic Schiff bases, a set of molecular descriptors were calculated by using B3P86 (Becke’s three parameter hybrid functional with Perdew 86 correlation functional) combined with 6-31 + G(d,p) basis set (i.e., at the B3P86/6-31 + G(d,p) level of theory). The chemometric methods, simple and multiple linear regressions (SLR and MLR), principal component analysis (PCA) and hierarchical cluster analysis (HCA) were employed to reduce the dimensionality and to investigate the relationship between the calculated descriptors and the antioxidant activity. The results showed that the antioxidant activity mainly depends on the first and second bond dissociation enthalpies of phenolic hydroxyl groups, the dipole moment and the hydrophobicity descriptors. The antioxidant activity is inversely proportional to the main descriptors. The selected descriptors discriminate the Schiff bases into active and inactive antioxidants. PMID:26784873

Noble-metal-free bimetallic alloy nanoparticle-catalytic gasification of phenol in supercritical water

DOE PAGES

Jia, Lijuan; Yu, Jiangdong; Chen, Yuan; ...

2017-08-01

The exploration of non-noble-metal catalysts for high efficiency gasification of biomass in supercritical water (SCW) is of great significance for the sustainable development. A series of Ni–M (M = Co or Zn) bimetallic nanoparticles supported on graphitized carbon black were synthesized and examined as catalysts for gasification of phenol in SCW. We found that a nearly complete gasification of phenol can be achieved even at a low temperature of 450 °C with the bimetallic nanoparticles catalysts. Kinetic study indicated the activation energy for phenol gasification were 20.4 ± 2.6 and 43.6 ± 2.6 kJ/mol for Ni20Zn15 and Ni20Co15 catalyst, respectively.more » Furthermore, XRD, XPS and TEM were performed to characterize the catalysts and the results showed the formation of NiCo and NiZn alloy phase. Catalyst recycling experiments were also conducted to evaluate the stability of the catalysts. The characterization of used catalysts suggest that the severe agglomeration of nanoparticles leads to the decrease in catalytic activity.« less

Synthesis of New Hydrated Geranylphenols and in Vitro Antifungal Activity against Botrytis cinerea

PubMed Central

Soto, Mauricio; Espinoza, Luis; Chávez, María I.; Díaz, Katy; Olea, Andrés F.; Taborga, Lautaro

2016-01-01

Geranylated hydroquinones and other geranylated compounds isolated from Aplydium species have shown interesting biological activities. This fact has prompted a number of studies where geranylated phenol derivatives have been synthesized in order to assay their bioactivities. In this work, we report the synthesis of a series of new hydrated geranylphenols using two different synthetic approaches and their inhibitory effects on the mycelial growth of Botrytis cinerea. Five new hydrated geranylphenols were obtained by direct coupling reaction between geraniol and phenol in dioxane/water and using BF3·Et2O as the catalyst or by the reaction of a geranylated phenol with BF3·Et2O. Two new geranylated quinones were also obtained. The synthesis and structural elucidation of all new compounds is presented. All hydrated geranylphenols efficiently inhibit the mycelial growth of B. cinerea. Their activity is higher than that observed for non-hydrated compounds. These results indicate that structural modification on the geranyl chain brings about an enhancement of the inhibition effect of geranylated phenol derivatives. PMID:27271604

Noble-metal-free bimetallic alloy nanoparticle-catalytic gasification of phenol in supercritical water

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

Jia, Lijuan; Yu, Jiangdong; Chen, Yuan

The exploration of non-noble-metal catalysts for high efficiency gasification of biomass in supercritical water (SCW) is of great significance for the sustainable development. A series of Ni–M (M = Co or Zn) bimetallic nanoparticles supported on graphitized carbon black were synthesized and examined as catalysts for gasification of phenol in SCW. We found that a nearly complete gasification of phenol can be achieved even at a low temperature of 450 °C with the bimetallic nanoparticles catalysts. Kinetic study indicated the activation energy for phenol gasification were 20.4 ± 2.6 and 43.6 ± 2.6 kJ/mol for Ni20Zn15 and Ni20Co15 catalyst, respectively.more » Furthermore, XRD, XPS and TEM were performed to characterize the catalysts and the results showed the formation of NiCo and NiZn alloy phase. Catalyst recycling experiments were also conducted to evaluate the stability of the catalysts. The characterization of used catalysts suggest that the severe agglomeration of nanoparticles leads to the decrease in catalytic activity.« less

Built-up resilience to climate change in peatlands

NASA Astrophysics Data System (ADS)

Wang, H.; Tian, J.; Ho, M.; Flanagan, N. E.; Vilgalys, R.; Richardson, C. J.

2017-12-01

Peatlands have stored about 30% of global soil carbon over millennia. Most studies suggest that climate change effects, like drought and warming, may decrease C sequestration and increase C loss in peatlands, thus resulting in a positive feedback on climate change. However, the long-term feedback between plant-microbe mediated carbon processes and climate change still remains highly uncertain. Here, we conducted a series of field and lab experiments in southern shrub and northern Sphagnum peatlands to document how previously unrecognized mechanisms regulate the buildup of anti-microbial phenolics, which protects stored carbon directly by reducing phenol oxidase activity during short-term drought, and indirectly through a shift from low-phenolics Sphagnum/herbs to high-phenolics shrubs after long-term moderate drought. We further showed a symbiosis of slow-growing decomposers concomitant with a shift of high-phenolic plants, which increased peat resistance to disturbance. Our results indicate that shrub expansion induced by climate change in boreal peatlands may be a long-term self-adaptive mechanism not only increasing carbon sequestration, but also potentially protecting soil carbon. Therefore, peatlands are highly resilient ecosystems in which the symbiotic adaption of both plants and microbes, triggered by persistent climate change, likely can acclimate to the stressors and maintain their carbon sequestration function and processes.

Aqueous phase hydrogenation of phenol catalyzed by Pd and PdAg on ZrO 2

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

Resende, Karen A.; Hori, Carla E.; Noronha, Fabio B.

Hydrogenation of phenol in aqueous phase was studied over a series of ZrO2-supported Pd catalysts in order to explore the effects of particle size and of Ag addition on the activity of Pd. Kinetic assessments were performed in a batch reactor, on monometallic Pd/ZrO2 samples with different Pd loadings (0.5%, 1% and 2%), as well as on a 1% PdAg/ZrO2 sample. The turnover frequency (TOF) increases with the Pd particle size. The reaction orders in phenol and H2 indicate that the surface coverages by phenol, H2 and their derived intermediates are higher on 0.5% Pd/ZrO2 than on other samples. Themore » activation energy was the lowest on the least active sample (0.5% Pd/ZrO2), while being identical on 1% and 2% Pd/ZrO2 catalysts. Thus, the significantly lower activity of the small Pd particles (1-2 nm on average) in 0.5%Pd/ZrO2 is explained by the unfavorable activation entropies for the strongly bound species. The presence of Ag increases considerably the TOF of the reaction by decreasing the Ea and increasing the coverages of phenol and H2.« less

Arcjet Testing of Advanced Conformal Ablative TPS

NASA Technical Reports Server (NTRS)

Gasch, Matthew; Beck, Robin; Agrawal, Parul

2014-01-01

A conformable TPS over a rigid aeroshell has the potential to solve a number of challenges faced by traditional rigid TPS materials (such as tiled Phenolic Impregnated Carbon Ablator (PICA) system on MSL. The compliant (high strain to failure) nature of the conformable ablative materials will allow integration of the TPS with the underlying aeroshell structure much easier and enable monolithic-like configuration and larger segments (or parts) to be used. In May of 2013 the CA250 project executed an arcjet test series in the Ames IHF facility to evaluate a phenolic-based conformal system (named Conformal-PICA) over a range of test conditions from 40-400Wcm2. The test series consisted of four runs in the 13-inch diameter nozzle. Test models were based on SPRITE configuration (a 55-deg sphere cone), as it was able to provide a combination of required heat flux, pressure and shear within a single entry. The preliminary in-depth TC data acquired during that test series allowed a mid-fidelity thermal response model for conformal-PICA to be created while testing of seam models began to address TPS attachment and joining of multiple segments for future fabrication of large-scale aeroshells. Discussed in this paper are the results.

Comparative assay of antioxidant packages for dimer of estolide esters

USDA-ARS?s Scientific Manuscript database

A series of 26 different antioxidants and commercial antioxidant packages, containing both natural and synthetic-based materials, were evaluated with dimeric coconut-oleic estolide 2-ethylhexyl ester. The different antioxidants were broken down into different classes of materials: phenolic, aminic, ...

Studies on the structural changes during curing of epoxy and its blend with CTBN

NASA Astrophysics Data System (ADS)

Srivastava, Kavita; Rathore, Ashwani Kumar; Srivastava, Deepak

2018-01-01

Cashew nut shell liquid (CNSL), an agricultural renewable resource material, produces natural phenolic distillates such as cardanol. Cardanol condenses with formaldehyde at the ortho- and para-position of the phenolic ring under acidic or alkaline condition to yield a series of polymers of novolac- or resol-type phenolic resins. These phenolic resins may further be modified by epoxidation with epichlorohydrin to duplicate the performance of such phenolic-type novolacs (CFN). The structural changes during curing of blend samples of epoxy and carboxyl terminated poly (butadiene-co-acrylonitrile) (CTBN) were studies by Fourier-transform infrared (FTIR) spectrophotometer. The epoxy samples were synthesized by biomass material, cardanol. Blend sample was prepared by physical mixing of CTBN ranging between 0 and 20 weight percent CTBN liquid rubber into cardanol-based epoxidized novolac (CEN) resin. The FTIR spectrum of uncured blend sample clearly indicated that there appeared a band in the region of 3200-3500 cm- 1 which might be due to the presence of phenolic hydroxyl group and sbnd OH group of the opened epoxide. Pure epoxy resin showed peaks near 856 cm- 1 which might be due to oxirane functionality of the epoxidized novolac resin. Both epoxy and its blend sample was cured with polyamine. The cure temperature of CEN resin was found to be decreased by the incorporation of CTBN. The decomposition behavior was also studied by thermogravimetric analyzer (TGA). Two-step decomposition behavior was observed in both epoxy and its blend samples.

Studies on the structural changes during curing of epoxy and its blend with CTBN.

PubMed

Srivastava, Kavita; Rathore, Ashwani Kumar; Srivastava, Deepak

2018-01-05

Cashew nut shell liquid (CNSL), an agricultural renewable resource material, produces natural phenolic distillates such as cardanol. Cardanol condenses with formaldehyde at the ortho- and para-position of the phenolic ring under acidic or alkaline condition to yield a series of polymers of novolac- or resol-type phenolic resins. These phenolic resins may further be modified by epoxidation with epichlorohydrin to duplicate the performance of such phenolic-type novolacs (CFN). The structural changes during curing of blend samples of epoxy and carboxyl terminated poly (butadiene-co-acrylonitrile) (CTBN) were studies by Fourier-transform infrared (FTIR) spectrophotometer. The epoxy samples were synthesized by biomass material, cardanol. Blend sample was prepared by physical mixing of CTBN ranging between 0 and 20weightpercent CTBN liquid rubber into cardanol-based epoxidized novolac (CEN) resin. The FTIR spectrum of uncured blend sample clearly indicated that there appeared a band in the region of 3200-3500cm -1 which might be due to the presence of phenolic hydroxyl group and OH group of the opened epoxide. Pure epoxy resin showed peaks near 856cm -1 which might be due to oxirane functionality of the epoxidized novolac resin. Both epoxy and its blend sample was cured with polyamine. The cure temperature of CEN resin was found to be decreased by the incorporation of CTBN. The decomposition behavior was also studied by thermogravimetric analyzer (TGA). Two-step decomposition behavior was observed in both epoxy and its blend samples. Copyright © 2017 Elsevier B.V. All rights reserved.

Kinetics of browning, phenolics, and 5-hydroxymethylfurfural in commercial sparkling wines.

PubMed

Serra-Cayuela, A; Jourdes, M; Riu-Aumatell, M; Buxaderas, S; Teissedre, P-L; López-Tamames, E

2014-02-05

We analyzed the degree of browning (absorbance at 420 nm), the phenolics, and the 5-hydroxymethylfurfural (5-HMF) content in six sparkling wines series kept at three temperatures (4, 16, and 20 °C) for over 2 years. Caffeic acid, trans-coutaric acid, p-coumaric acid, and 5-HMF were the compounds with the greatest correlation with browning and time. 5-HMF was the only compound that evolved linearly at all temperatures. We propose that 5-HMF is a better time-temperature marker than the A₄₂₀ parameter or phenolics, because it shows higher linearity with time at all temperatures, is more sensitive to temperature changes, and has lower variability. The kinetics of 5-HMF was studied showing a zero-order behavior. We propose mathematical models that wineries can use to predict the browning shelf life of their sparkling wines as a function of the storage time and temperature.

Exploring Cancer Therapeutics with Natural Products from African Medicinal Plants, Part I: Xanthones, Quinones, Steroids, Coumarins, Phenolics and other Classes of Compounds.

PubMed

Simoben, Conrad V; Ibezim, Akachukwu; Ntie-Kang, Fidele; Nwodo, Justina N; Lifongo, Lydia L

2015-01-01

Cancer is known to be the second most common disease-related cause of death among humans. In drug discovery programs anti-cancer chemotherapy remains quite challenging due to issues related to resistance. Plants used in traditional medicine are known to contribute significantly within a large proportion of the African population. A survey of the literature has led to the identification of ~400 compounds from African medicinal plants, which have shown anti-cancer, anti-proliferation, anti-tumor and/or cytotoxic activities, tested by in vitro and in vivo assays (from mildly active to very active), mainly alkaloids, terpenoids, flavonoids, coumarins, phenolics, polyacetylates, xanthones, quinones, steroids and lignans. The first part of this review series focuses on xanthones, quinones, steroids, coumarins, phenolics and other compound classes, while part II is focused on alkaloids, terpenoids, flavonoids.

Aromatics and phenols from catalytic pyrolysis of Douglas fir pellets in microwave with ZSM-5 as a catalyst

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

Wang, Lu; Lei, Hanwu; Ren, Shoujie

Microwave assisted catalytic pyrolysis was investigated to convert Douglas fir pellets to bio-oils by a ZSM-5 Zeolite catalyst. A central composite experimental design (CCD) was used to optimize the catalytic pyrolysis process. The effects of reaction time, temperature and catalyst to biomass ratio on the bio-oil, syngas, and biochar yields were determined. GC/MS analysis results showed that the bio-oil contained a series of important and useful chemical compounds. Phenols, guaiacols, and aromatic hydrocarbons were the most abundant compounds which were about 50-82 % in bio-oil depending on the pyrolysis conditions. Comparison between the bio-oils from microwave pyrolysis with and withoutmore » catalyst showed that the catalyst increased the content of aromatic hydrocarbons and phenols. A reaction pathway was proposed for microwave assisted catalyst pyrolysis of Douglas fir pellets.« less

Interactions of Kraft lignin and wheat gluten during biomaterial processing: evidence for the role of phenolic groups.

PubMed

Kaewtatip, Kaewta; Menut, Paul; Auvergne, Remi; Tanrattanakul, Varaporn; Morel, Marie-Helene; Guilbert, Stephane

2010-04-14

The chemical interactions between Kraft lignin and wheat gluten under processing conditions were investigated by determining the extent of the protein network formation. To clarify the role of different chemical functions found in lignin, the effect of Kraft lignin was compared with that of an esterified lignin, in which hydroxyl groups had been suppressed by esterification, and with a series of simple aromatics and phenolic structures with different functionalities (conjugated double bonds, hydroxyl, carboxylic acid, and aldehyde). The protein solubility was determined by using the Kjeldahl method. The role of the hydroxyl function was assessed by the significantly lower effect of esterified lignin. The importance of the phenolic radical scavenging structure is evidenced by the effect of guaiacol, which results in a behavior similar to that of the Kraft lignin. In addition, the significant effect of conjugated double bonds on gluten reactivity, through nucleophilic addition, was demonstrated.

Symposium on Toxic Substance Control: Decontamination, April 22 - 24, 1980, Columbus, Ohio.

DTIC Science & Technology

1981-06-01

standard decontaminants is used. TABLE 1. Standard Chemical Decontaminants Decontaminant Agents Used On STB Blister and nerve agents DS-2 All chemical... agents M258 Kit Sodium Hydroxide, Ethanol, G-Series nerve agents Phenol, Water Chloramine B, ZnCI2, Blister ana V-Series Ethanol, Water nerve agents A...is a point source alarm that actively samples ambient air and reacts to low concentrations of nerve agents . The M-8 alarm detector also detects several

21 CFR 74.1327 - D&C Red No. 27.

Code of Federal Regulations, 2010 CFR

2010-04-01

... bromine. The 4,5,6,7-tetrachlorofluorescein is manufactured by the acid condensation of resorcinol and tetrachlorophthalic acid or its anhydride. The 4,5,6,7-tetrachlorofluorescein is isolated and partially purified prior... avoided by current good manufacturing practice: Sum of volatile matter (at 135 °C) and halides and...

21 CFR 333.320 - Permitted combinations of active ingredients.

Code of Federal Regulations, 2013 CFR

2013-04-01

... 21 Food and Drugs 5 2013-04-01 2013-04-01 false Permitted combinations of active ingredients. 333.320 Section 333.320 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN... Topical Acne Drug Products § 333.320 Permitted combinations of active ingredients. (a) Resorcinol...

21 CFR 333.320 - Permitted combinations of active ingredients.

Code of Federal Regulations, 2011 CFR

2011-04-01

... 21 Food and Drugs 5 2011-04-01 2011-04-01 false Permitted combinations of active ingredients. 333.320 Section 333.320 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN... Topical Acne Drug Products § 333.320 Permitted combinations of active ingredients. (a) Resorcinol...

21 CFR 333.320 - Permitted combinations of active ingredients.

Code of Federal Regulations, 2012 CFR

2012-04-01

... 21 Food and Drugs 5 2012-04-01 2012-04-01 false Permitted combinations of active ingredients. 333.320 Section 333.320 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN... Topical Acne Drug Products § 333.320 Permitted combinations of active ingredients. (a) Resorcinol...

21 CFR 333.320 - Permitted combinations of active ingredients.

Code of Federal Regulations, 2010 CFR

2010-04-01

... 21 Food and Drugs 5 2010-04-01 2010-04-01 false Permitted combinations of active ingredients. 333... Topical Acne Drug Products § 333.320 Permitted combinations of active ingredients. (a) Resorcinol... of the user, the revised text is set forth as follows: § 333.320 Permitted combinations of active...

21 CFR 333.320 - Permitted combinations of active ingredients.

Code of Federal Regulations, 2014 CFR

2014-04-01

... 21 Food and Drugs 5 2014-04-01 2014-04-01 false Permitted combinations of active ingredients. 333.320 Section 333.320 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN... Topical Acne Drug Products § 333.320 Permitted combinations of active ingredients. (a) Resorcinol...

RECOGNITION OF PYRENE USING MOLECULARLY-IMPRINTED ELECTROCHEMICALLY-DEPOSITED POLY (2-MERCAPTOBENZIMIDAZOLE) OR POLY(RESORCINOL) ON GOLD ELECTRODES

EPA Science Inventory

The feasibility of using thiol chemistry to form molecularly imprinted polymer-coated gold electrodes to measure pyrene is reported. For the first approach, poly(2-mercaptoimidazole) (2-MBI) was electrochemically deposited on gold electrodes in the presence or absence of the tem...

Aquagel electrode separator for use in batteries and supercapacitors

DOEpatents

Mayer, S.T.; Kaschmitter, J.L.; Pekala, R.W.

1995-03-28

An electrode separator is described for electrochemical energy storage devices, such as a high energy density capacitor incorporating a variety of carbon foam electrodes. The separator is derived from an aquagel of resorcinol-formaldehyde and related polymers and containing ionically conducting electrolyte in the pores thereof. 9 figures.

Gas Chromatography/Atmospheric Pressure Chemical Ionization-Fourier Transform Ion Cyclotron Resonance Mass Spectrometry of Pyrolysis Oil from German Brown Coal

PubMed Central

Zuber, Jan; Kroll, Marius M.; Rathsack, Philipp; Otto, Matthias

2016-01-01

Pyrolysis oil from the slow pyrolysis of German brown coal from Schöningen, obtained at a temperature of 500°C, was separated and analyzed using hyphenation of gas chromatography with an atmospheric pressure chemical ionization source operated in negative ion mode and Fourier transform ion cyclotron resonance mass spectrometry (GC-APCI-FT-ICR-MS). Development of this ultrahigh-resolving analysis method is described, that is, optimization of specific GC and APCI parameters and performed data processing. The advantages of GC-APCI-FT-ICR-MS hyphenation, for example, soft ionization, ultrahigh-resolving detection, and most important isomer separation, were demonstrated for the sample liquid. For instance, it was possible to separate and identify nine different propylphenol, ethylmethylphenol, and trimethylphenol isomers. Furthermore, homologous series of different acids, for example, alkyl and alkylene carboxylic acids, were verified, as well as homologous series of alkyl phenols, alkyl dihydroxy benzenes, and alkoxy alkyl phenols. PMID:27066076

Antimony photoresists for EUV lithography: mechanistic studies

NASA Astrophysics Data System (ADS)

Murphy, Michael; Narasimhan, Amrit; Grzeskowiak, Steven; Sitterly, Jacob; Schuler, Philip; Richards, Jeff; Denbeaux, Greg; Brainard, Robert L.

2017-03-01

We have developed a method to study the photomechanism of our antimony carboxylate platform R3Sb(COOR')2. A series of mechanistic studies followed the production of reaction byproducts by mass spectrometer, as they left the film during exposure to EUV photons and 80 eV electrons. We identified several prominent outgassing fragments and their rates of production as a function of ligand structure. The degree of outgassing appears to be well-correlated with the bond dissociation energy of the carboxylate ligand R' group. Furthermore, a deuterium labeling study was conducted to determine from which ligand hydrogen is abstracted to form benzene and phenol during exposure. Benzene and phenol were found to abstract hydrogen from opposing sites within the film, and with greater than 95% isotopic purity. Using the results of the outgassing studies alongside established mechanisms for electron-induced reactions; a series of reaction pathways were proposed to generate the aforementioned outgassing species and a possible nonvolatile negative-tone photoproduct.

Discovery of benzotriazole-azo-phenol/aniline derivatives as antifungal agents.

PubMed

Lv, Min; Ma, Jingchun; Li, Qin; Xu, Hui

2018-01-15

A series of benzotriazole-azo-phenol/aniline derivatives were prepared and evaluated for their antifungal activities against six phytopathogenic fungi such as Fusarium graminearum, Fusarium solani, Alternaria alternate, Valsa mali, Botrytis cinerea, and Curvularia lunata. Among them, compounds IIf, IIn, and IIr showed a broad-spectrum of potent antifungal activities. Especially some compounds displayed 3.5-10.8 folds more potent activities than carbendazim against A. alternata and C. lunata. Notably, compounds IIc, IIm, and IIr exhibited good protective and therapeutic effects against B. cinerea at 200 μg/mL. Their structure-activity relationships were also discussed. Copyright © 2017 Elsevier Ltd. All rights reserved.

Detection of Sendai virus receptor, the ganglioside GDla, in target tissue (mouse lung)

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

Markwell, M.A.K.; Sato, E.

1986-05-01

Previously the authors had shown that the gangliosides GDla, GTlb, and GQlb derived from brain function as receptors for the paramyxovirus Sendai virus by their ability to induce infection when incubated with receptor-deficient cells. Analyses of MDBK, HeLa, and MDCK cells in culture demonstrated that these putative receptors were present in host cells in the quantities required for infection. The primary site of infection for Sendai virus in the whole animal is the respiratory tract, culminating in the lung. Therefore, the ganglioside content of this target organ was analyzed to determine the endogenous receptor population available to Sendai virus. Themore » total ganglioside fraction of lung was resolved into individual species by HPTLC. Gangliosides of the gangliotetraose series were identified by the specific binding of /sup 125/I-labeled tetanus and cholera toxins before and after exposure with sialidase. In this manner one of the major resorcinol-positive bands was identified as GDla. Evidence of the more complex ganglioside receptors for Sendai virus was also seen.« less

Preparation and application of microcapsule-encapsulated color electrophortic fluid in Isopar M system for electrophoretic display

NASA Astrophysics Data System (ADS)

Sun, Cui; Feng, Ya-Qing; Zhang, Bao; Li, Xiang-Gao; Shao, Ji-Zhou; Han, Jing-Jing; Chen, Xu

2013-05-01

The use of Isopar M as a liquid suspending fluid for electrophoretic display was studied. The dispersion stability and chargeability of pigments suspended in Isopar M were investigated. Polyisobutylene monosuccinimide (T-151) as the charge control additive in Isopar M electrophoretic fluid can provide a good electrophoretic mobility to the particles. The wall materials of a series of blue-white, red-white and yellow-white dual-particle microcapsules were prepared by in situ polymerization of urea and formaldehyde. The mass ratio of wall/core material was a key factor in influencing the yield of microcapsules. The concentration of resorcinol has an impact on the surface morphology and mechanical strength of microcapsule wall. Microcapsules' surface morphologies were characterized by optical microscopy and scanning electron microscopy. The performance of the microcapsules with different binder materials and adhesive layers were investigated. Contrast ratio of microcapsules display device were tested every 10 days for a period of 90 days. The compatibility of Isopar M with both the electrophoretic particles and bounding capsule was studied.

Comparison of different extraction procedures for the comprehensive characterization of bioactive phenolic compounds in Rosmarinus officinalis by reversed-phase high-performance liquid chromatography with diode array detection coupled to electrospray time-of-flight mass spectrometry.

PubMed

Borrás Linares, I; Arráez-Román, D; Herrero, M; Ibáñez, E; Segura-Carretero, A; Fernández-Gutiérrez, A

2011-10-21

In the present work, a comparative study between two environmentally friendly and selective extraction techniques, such as supercritical fluid extraction (SFE) and pressurized liquid extraction (PLE) have been carried out focusing in the bioactive phenolic compounds present in Rosmarinus officinalis. For the analysis of the SFE and PLE extracts, a new methodology for qualitative characterization has been developed, based on the use of reversed-phase high-performance liquid chromatography (RP-HPLC), equipped with two different detection systems coupled in series: diode array detector (DAD) and time of flight mass spectrometry (TOF-MS) detector connected via an electrospray ionization interface (ESI). The use of a small particle size C(18) column (1.8 μm) provided a great resolution and made possible the separation of several isomers. Moreover, UV-visible spectrophotometry is a valuable tool for identifying the class of phenolic compounds, whereas MS data enabled to structurally characterize the compounds present in the extracts. The applied methodology was useful for the determination of many well-known phenolic compounds present in R. officinalis, such as carnosol, carnosic acid, rosmadial, rosmanol, genkwanin, homoplantaginin, scutellarein, cirsimaritin and rosmarinic acid, as well as other phenolic compounds present in other species belonging to Lamiaceae family. Copyright © 2011 Elsevier B.V. All rights reserved.

Catalytic performance of strong acid catalyst: Methyl modified SBA-15 loaded perfluorinated sulfonic acid obtained by the waste perfluorinated sulfonic acid ion exchange membrane

NASA Astrophysics Data System (ADS)

Jiang, Tingshun; Huang, Qiuyan; Li, Yingying; Fang, Minglan; Zhao, Qian

2018-02-01

Mesoporous molecular sieve (SBA-15) was modified using the trimethylchlorosilane as functional agent and the silylation SBA-15 mesoporous material was prepared in this work. The alcohol solution of perfluorinated sulfonic acid dissolved from the waste perfluorinated sulfonic acid ion exchange membrane (PFSIEM) was loaded onto the resulting mesoporous material by the impregnation method and their physicochemical properties were characterized by FT-IR, N2-physisorption, XRD, TG-DSC and TEM. The catalytic activities of these synthesized solid acid catalysts were evaluated by alkylation of phenol with tert-butyl alcohol. The influence of reaction temperature, weight hour space velocity (WHSV) and reaction time on the phenol conversion and product selectivity were assessed by means of a series of experiments. The results showed that with the increase of the active component of the catalyst, these catalysts still remained good mesoporous structure, but the mesoporous ordering decreased to some extent. These catalysts exhibited good catalytic performance for the alkylation of phenol with tert-butanol. The maximum phenol conversion of 89.3% with 70.9% selectivity to 4-t-butyl phenol (4-TBP) was achieved at 120 °C and the WHSV is 4 h-1. The methyl group was loaded on the surface of the catalyst by trimethylchlorosilane. This is beneficial to retard the deactivation of the catalyst. In this work, the alkylation of phenol with tert-butyl alcohol were carried out using the methyl modified SBA-15 mesoporous materials loaded perfluorinated sulfonic acid as catalysts. The results show that the resulting catalyst exhibited high catalytic activity.

21 CFR 74.1322 - D&C Red No. 22.

Code of Federal Regulations, 2010 CFR

2010-04-01

.... The fluorescein is manufactured by the acid condensation of resorcinol and phthalic acid or its... good manufacturing practice: Sum of volatile matter (at 135°C) and halides and sulfates (calculated as... of phthalic acid, not more than 1 percent. Sodium salt of 2-(3,5-Dibromo-2,4-dihydroxybenzoyl)benzoic...

Effects of swelling forces on the durability of wood adhesive bonds

Treesearch

Blake M. Hofferber; Edward Kolodka; Rishawn Brandon; Robert J. Moon; Charles R. Frihart

2006-01-01

The purpose of this study was to investigate the role of wood swelling on performance of wood-adhesive bonds (resorcinol formaldehyde, epoxy, emulsion polymerisocyanate), for untreated and acetylated wood. Effects of these treatments on measured strain anisotropy and swelling stress were measured and then related to compressive shear strength and percentage wood...

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

Kirimura, Kohtaro, E-mail: kkohtaro@waseda.jp; Watanabe, Shotaro; Kobayashi, Keiichi

Type III polyketide synthases (PKSs) catalyze the formation of pyrone- and resorcinol-types aromatic polyketides. The genomic analysis of the filamentous fungus Aspergillus niger NRRL 328 revealed that this strain has a putative gene (chr-8-2: 2978617–2979847) encoding a type III PKS, although its functions are unknown. In this study, for functional analysis of this putative type III PKS designated as An-CsyA, cloning and heterologous expression of the An-CsyA gene (An-csyA) in Escherichia coli were performed. Recombinant His-tagged An-CsyA was successfully expressed in E. coli BL21 (DE3), purified by Ni{sup 2+}-affinity chromatography, and used for in vitro assay. Tests on the substrate specificity ofmore » the His-tagged An-CsyA with myriad acyl-CoAs as starter substrates and malonyl-CoA as extender substrate showed that His-tagged An-CsyA accepted fatty acyl-CoAs (C2-C14) and produced triketide pyrones (C2-C14), tetraketide pyrones (C2-C10), and pentaketide resorcinols (C10-C14). Furthermore, acetoacetyl-CoA, malonyl-CoA, isobutyryl-CoA, and benzoyl-CoA were also accepted as starter substrates, and both of triketide pyrones and tetraketide pyrones were produced. It is noteworthy that the His-tagged An-CsyA produced polyketides from malonyl-CoA as starter and extender substrates and produced tetraketide pyrones from short-chain fatty acyl-CoAs as starter substrates. Therefore, this is the first report showing the functional properties of An-CsyA different from those of other fungal type III PKSs. -- Highlights: •Type III PKS from Aspergillus niger NRRL 328, An-CsyA, was cloned and characterized. •An-CsyA produced triketide pyrones, tetraketide pyrones and pentaketide resorcinols. •Functional properties of An-CsyA differs from those of other fungal type III PKSs.« less

Construction of divergent fused heterocycles via an acid-promoted intramolecular ipso-Friedel-Crafts alkylation of phenol derivatives.

PubMed

Yokosaka, Takuya; Shiga, Naoki; Nemoto, Tetsuhiro; Hamada, Yasumasa

2014-05-02

Two different cascade cyclization processes were developed using aryl group-substituted propargyl alcohol derivatives with a p-hydroxybenzylamine unit as common substrates. Using TFA as an acid promoter, an intramolecular ipso-Friedel-Crafts alkylation of phenol derivatives, formation of an iminium cation via a rearomatization-promoted C-C bond cleavage, an aza-Prins reaction, and a 6-membered ring formation proceeded sequentially, producing a variety of fused-tricyclic dihydroquinoline derivatives in 45-99% yield. In addition, a one-pot sequential silver acetate-catalyzed hydroamination/etherification-acid-promoted skeletal rearrangement was examined using the same series of substrates, affording fused-tricyclic indole/benzofuran derivatives in 66-89% yield.

Almond (Prunus dulcis (Mill.) D.A. Webb) skins as a potential source of bioactive polyphenols.

PubMed

Monagas, Maria; Garrido, Ignacio; Lebrón-Aguilar, Rosa; Bartolome, Begoña; Gómez-Cordovés, Carmen

2007-10-17

An exhaustive study of the phenolic composition of almond ( Prunus dulcis (Mill.) D.A. Webb) skins was carried out in order to evaluate their potential application as a functional food ingredient. Using the HPLC-DAD/ESI-MS technique, a total of 33 compounds corresponding to flavanols, flavonols, dihydroflavonols and flavanones, and other nonflavonoid compounds were identified. Peaks corresponding to another 23 structure-related compounds were also detected. MALDI-TOF MS was applied to characterize almond skin proanthocyanidins, revealing the existence of a series of A- and B-type procyanidins and propelargonidins up to heptamers, and A- and B-type prodelphinidins up to hexamers. Flavanols and flavonol glycosides were the most abundant phenolic compounds in almond skins, representing up to 38-57% and 14-35% of the total quantified phenolics, respectively. Due to their antioxidant properties, measured as oxygen-radical absorbance capacity (ORAC) at 0.398-0.500 mmol Trolox/g, almond skins can be considered as a value-added byproduct for elaborating dietary antioxidant ingredients.

In Vitro Antifungal Activity of New and Known Geranylated Phenols against Phytophthora cinnamomi Rands.

PubMed

Chavez, María I; Soto, Mauricio; Cimino, Franco A; Olea, Andrés F; Espinoza, Luis; Díaz, Katy; Taborga, Lautaro

2018-05-29

A series of new and known geranylated phenol/methoxyphenol derivatives has been tested in vitro as inhibitor agents of mycelial growth of Phytophthora cinnamomi . The activity of tested compounds is correlated with the nature, number, and position of the substituent group on the aromatic ring. Results indicate that the most active geranylated derivatives are those having two hydroxyl groups (or one ⁻OH and one ⁻OCH₃) attached to the aromatic ring. Interestingly, these derivatives are as active as Metalaxil ® , a commonly used commercial fungicide. Thus, our results suggest that some of these compounds might be of agricultural interest due to their potential use as fungicides against P. cinnamomi . The effect of structure on fungicide activity is discussed in terms of electronic distribution on both the aromatic ring and side geranyl chain. All tested compounds have been synthesized by direct coupling of geraniol and the respective phenol. Interestingly, new digeranylated derivatives were obtained by increasing the reaction time.

Copper(II) and zinc(II) dinuclear enzymes model compounds: The nature of the metal ion in the biological function

NASA Astrophysics Data System (ADS)

Ferraresso, L. G.; de Arruda, E. G. R.; de Moraes, T. P. L.; Fazzi, R. B.; Da Costa Ferreira, A. M.; Abbehausen, C.

2017-12-01

First series transition metals are used abundantly by nature to perform catalytic transformations of several substrates. Furthermore, the cooperative activity of two proximal metal ions is common and represents a highly efficient catalytic system in living organisms. In this work three dinuclear μ-phenolate bridged metal complexes were prepared with copper(II) and zinc(II), resulting in a ZnZn, CuCu and CuZn with the ligand 2-ethylaminodimethylamino phenol (saldman) as model compounds of superoxide dismutase (CuCu and CuZn) and metallo-β-lactamases (ZnZn). Metals are coordinated in a μ-phenolate bridged symmetric system. Cu(II) presents a more distorted structure, while zinc is very symmetric. For this reason, [CuCu(saldman)] shows higher water solubility and also higher lability of the bridge. The antioxidant and hydrolytic beta-lactamase-like activity of the complexes were evaluated. The lability of the bridge seems to be important for the antioxidant activity and is suggested to because of [CuCu(saldman)] presents a lower antioxidant capacity than [CuZn(saldman)], which showed to present a more stable bridge in solution. The hydrolytic activity of the bimetallic complexes was assayed using nitrocefin as substrate and showed [ZnZn(saldman)] as a better catalyst than the Cu(II) analog. The series demonstrates the importance of the nature of the metal center for the biological function and how the reactivity of the model complex can be modulated by coordination chemistry.

Toxicity prediction of PHDDs and phenols in the light of nucleic acid bases and DNA base pair interaction.

PubMed

Mondal Roy, Sutapa; Roy, Debesh R; Sahoo, Suban K

2015-11-01

The applicability of Density Functional Theory (DFT) based descriptors for the development of quantitative structure-toxicity relationships (QSTR) is assessed for two different series of toxic aromatic compounds, viz., polyhalogenated dibenzo-p-dioxins (PHDDs) and phenols (PHs). A series of 20 compounds each for PHDDs and PHs with their experimental toxicities (IC50 and IGC50) is chosen in the present study to develop DFT based efficient quantum chemical parameters (QCPs) for explaining the toxin potential of the considered compounds. A systematic analysis to find out the electron donation/acceptance nature of these selected compounds with the considered model biosystems, viz., nucleic acid (NA) bases and DNA base pairs, is performed to identify potential QCPs. Accordingly, PHDDs is found to be electron acceptors whereas phenols as donors, during their interaction with biosystems. Two parameter regression model is carried out comprising global charge transfer (ΔN), and local Fukui Function's for nucleophilic attack (fk(+)) for PHDDs and the same for electrophilic attack (fk(-)) in case of PHs. It is heartening to note that our chosen descriptors, viz, charge transfer (ΔN) and Fukui Function (fk(±)) plays a crucial role by explaining more than 90% of the observed toxic behavior (in terms of correlation-coefficient, R) of PHDDs and PHs. The developed QCPs, viz., ΔN and fk(±) can be added as the new descriptors in the QSTR parlance. Copyright © 2015 Elsevier Inc. All rights reserved.

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

Duignan, M. R.; Herman, D. T.; Restivo, M. L.

Experiments at several different scales were performed to understand the removal of spherical resorcinol formaldehyde (sRF) ion exchange resin using a gravity drain system with a valve located above the resin screen in the ion exchange column (IXC). This is being considered as part of the design for the Low Activity Waste Pretreatment System (LAWPS) to be constructed at the DOE Hanford Site.

Using the DFT-D method to describe dispersion interactions in systems of weakly-bonded Xe-aromatic molecules

NASA Astrophysics Data System (ADS)

Andriichenko, N. N.; Ermilov, A. Yu.

2013-08-01

The optimum version of the DFT-D class of methods (BHHLYP-D2, 6-31G*) is chosen to describe binding in a Xe-phenol system with the aim of subsequent KM/MM calculations for complex Xe-containing protein systems. It is shown that the stability of the Xe-phenol system is due to weak dispersion interactions not described in conventional approaches using the density functional. The MP2 approach using the (aug)-cc-pVTZ basis and Stuttgart pseudopotential, which yield the best reproduction of the characteristics of a Xe2 xenon dimer, is chosen as the reference standard. It is noted that the 2010 DFT-D3 methods underestimate the binding energy by a factor of nearly three, while DFT methods without dispersion corrections do not reproduce the stability of Xe2 and Xe-phenol systems. It is found that in the best version of calculations, BHHLYP-D2, the binding energy in Xe-phenol complex is estimated to be 2.7 kcal/mol versus the 3.1 kcal/mol found using the comparative approach. It is concluded that BHHLYP-D2 adequately reproduces the difference between the two conformers of the Xe-phenol complex and trend toward an increase in binding energy in the series of aromatic amino acids (phenylalanine, tyrosine, and tryptophan). DFT-D can also indicate the existence of excess conformers that are missing in systems according to more precise descriptions (MP2/(aug)-cc-pVTZ).

Filtrates and Residues: Optical Projection Experiments to Demonstrate New Curricula Contents.

ERIC Educational Resources Information Center

Perina, Ivo

1986-01-01

Presents background information and procedures for 12 experiments dealing with such areas as: reactivity of a homologous series of saturated monovalent alcohols; enzymatic degradation of hydrogen peroxide by catalase; effect of an activator and inhibitor on amylase activity; proving the existence of phenol in waste water; detecting common air…

Macro-kinetic investigation on phenol uptake from air by biofiltration: Influence of superficial gas flow rate and inlet pollutant concentration

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

Zilli, M.; Fabiano, B.; Ferraiolo, A.

1996-02-20

The macro-kinetic behavior of phenol removal from a synthetic exhaust gas was investigated theoretically as well as experimentally by means of two identical continuously operating laboratory-scale biological filter bed columns. A mixture of peat and glass beads was used as filter material. After sterilization it was inoculated with a pure strain of Pseudomonas putida, as employed in previous experimental studies. To determine the influence of the superficial gas flow rate on biofilter performance and to evaluate the phenol concentration profiles along the column, two series of continuous tests were carried out varying either the inlet phenol concentration, up to 1,650more » mg {center_dot} m{sup {minus}3}, or the superficial gas flow rate, from 30 to 460 m{sup 3} {center_dot} m{sup {minus}2} {center_dot} h{sup {minus}1}. The elimination capacity of the biofilter is proved by a maximum volumetric phenol removal rate of 0.73 kg {center_dot} m{sup {minus}3} {center_dot} h{sup {minus}1}. The experimental results are consistent with a biofilm model incorporating first-order substrate elimination kinetics. The model may be considered a useful tool in scaling-up a biofiltration system. Furthermore, the deodorization capacity of the biofilter was investigated, at inlet phenol concentrations up to 280 mg {center_dot} m{sup {minus}3} and superficial gas flow rates ranging from 30 to 92 m{sup 3} {center_dot} m{sup {minus}2} {center_dot} h{sup {minus}1}. The deodorization of the gas was achieved at a maximum inlet phenol concentration of about 255 mg {center_dot} m{sup {minus}3}, operating at a superficial gas flow rate of 30 m{sup 3} {center_dot} m{sup {minus}2} {center_dot} h{sup {minus}1}.« less

Quenching of triplet-excited flavins by flavonoids. Structural assessment of antioxidative activity.

PubMed

Huvaere, Kevin; Olsen, Karsten; Skibsted, Leif H

2009-10-02

The mechanism of flavin-mediated photooxidation of flavonoids was investigated for aqueous solutions. Interaction of triplet-excited flavin mononucleotide with phenols, as determined by laser flash photolysis, occurred at nearly diffusion-controlled rates (k approximately 1.6 x 10(9) L mol(-1) s(-1) for phenol at pH 7, 293 K), but protection of the phenolic function by methylation inhibited reaction. Still, electron transfer was proposed as the dominating mechanism due to the lack of primary kinetic hydrogen/deuterium isotope effect and the low activation enthalpy (<20 kJ mol(-1)) for photooxidation. Activation entropy worked compensating in a series of phenolic derivatives, supporting a common oxidation mechanism. An ortho-hydroxymethoxy pattern was equally reactive (k approximately 2.3 x 10(9) L mol(-1) s(-1) for guaiacol at pH 7) as compounds with ortho-dihydroxy substitution (k approximately 2.4 x 10(9) L mol(-1) s(-1) for catechol at pH 7), which are generally referred to as good antioxidants. This refutes the common belief that stabilization of incipient phenoxyl radicals through intramolecular hydrogen bonding is the driving force behind the reducing activity of catechol-like compounds. Instead, such bonding improves ionization characteristics of the substrates, hence the differences in reactivity with (photo)oxidation of isolated phenols. Despite the similar reactivity, radicals from ortho-dihydroxy compounds are detected in high steady-state concentrations by electron paramagnetic resonance (EPR) spectroscopy, while those resulting from oxidation of ortho-hydroxymethoxy (or isolated phenolic) patterns were too reactive to be observed. The ability to deprotonate and form the corresponding radical anions at neutral pH was proposed as the decisive factor for stabilization and, consequently, for antioxidative action. Thus, substituting other ionizable functions for the ortho- or para-hydroxyl in phenolic compounds resulted in stable radical anion formation, as demonstrated for para-hydroxybenzoic acid, in contrast to its methyl ester.

Early diagenesis of vascular plant tissues: Lignin and cutin decomposition and biogeochemical implications

NASA Astrophysics Data System (ADS)

Opsahl, Stephen; Benner, Ronald

1995-12-01

Long-term subaqueous decomposition patterns of five different vascular plant tissues including mangrove leaves and wood ( Avicennia germinans), cypress needles and wood ( Taxodium distichum) and smooth cordgrass ( Spartina alternifora) were followed for a period of 4.0 years, representing the longest litter bag decomposition study to date. All tissues decomposed under identical conditions and final mass losses were 97, 68, 86, 39, and 93%, respectively. Analysis of the lignin component of herbaceous tissues using alkaline CuO oxidation was complicated by the presence of a substantial ester-bound phenol component composed primarily of cinnamyl phenols. To overcome this problem, we introduce a new parameter to represent lignin, Λ6. Λ6 is comprised only of the six syringyl and vanillyl phenols and was found to be much less sensitive to diagenetic variation than the commonly used parameter Λ, which includes the cinnamyl phenols. Patterns of change in lignin content were strongly dependent on tissue type, ranging from 77% enrichment in smooth cordgrass to 6% depletion in cypress needles. In contrast, depletion of cutin was extensive (65-99%) in all herbaceous tissues. Despite these differences in the overall reactivity of lignin and cutin, both macromolecules were extensively degraded during the decomposition period. The long-term decomposition series also provided very useful information about the compositional parameters which are derived from the specific oxidation products of both lignin and cutin. The relative lability of ester-bound cinnamyl phenols compromised their use in parameters to distinguish woody from herbaceous plant debris. The dimer to monomer ratios of lignin-derived phenols indicated that most intermonomeric linkages in lignin degraded at similar rates. Acid to aldehyde ratios of vanillyl and syringyl phenols became elevated, particularly during the latter stages of decomposition supporting the use of these parameters as indicators of diagenetic alteration. Given the observation that cutin-derived source indicator parameters were generally more sensitive to diagenetic alteration than those of lignin, we suggest the distributional patterns of cutin-derived acids and their associated positional isomers may be most useful for tissue-specific distinctions complementing the general categorical information obtained from lignin phenol analysis alone.

Pyrolysis-high resolution gas chromatography and pyrolysis gas chromatography-mass spectrometry of kerogens and kerogen precursors

NASA Technical Reports Server (NTRS)

Van De Meent, D.; Brown, S. C.; Philp, R. P.; Simoneit, B. R. T.

1980-01-01

A series of kerogens and kerogen precursors isolated from DSDP samples, oil shales and recent algal mats have been examined by Curie point pyrolysis-high resolution gas chromatography and gas chromatography-mass spectrometry. This study has shown that the three main types of kerogens (marine, terrestrial and mixtures of both) can be characterized using these techniques. The marine (algal) kerogens yield principally aliphatic products and the terrestrial kerogens yield more aromatic and phenolic products with some n-alkanes and n-alkenes. The yields of n-alkanes and n-alkenes increase and phenols decrease with increasing geologic age, however, pyrolysis-GC cannot be used to characterize the influence of short term diagenesis on the kerogen structure.

Chemical constituents of Piper betle Linn. (Piperaceae) roots.

PubMed

Ghosh, K; Bhattacharya, T K

2005-08-31

Column chromatography of the alcoholic extract of Piper betle roots furnished aristololactam A-II and a new phenyl propene, characterized as 4-allyl resorcinol, while the petroleum-ether extract yielded a diketosteroid, viz. stigmast-4-en-3,6-dione. All these compounds were characterized by spectroscopic means. Isolation of these compounds from this source is being reported here for the first time.

Quantitative determination of a-Arbutin, ß-Arbutin, Kojic acid, nicotinamide, hydroquinone, resorcinol, 4-methoxyphenol, 4-ethoxyphenol and ascorbic acid from skin whitening Products by HPLC-UV

USDA-ARS?s Scientific Manuscript database

Development of an analytical method for the simultaneous determination of multifarious skin whitening agents will provide an efficient tool to analyze skin whitening cosmetics. An HPLC-UV method was developed for quantitative analysis of six commonly used whitening agents, a-arbutin, ß-arbutin, koji...

Bimodal activated carbons derived from resorcinol-formaldehyde cryogels

PubMed Central

Szczurek, Andrzej; Amaral-Labat, Gisele; Fierro, Vanessa; Pizzi, Antonio; Celzard, Alain

2011-01-01

Resorcinol-formaldehyde cryogels prepared at different dilution ratios have been activated with phosphoric acid at 450 °C and compared with their carbonaceous counterparts obtained by pyrolysis at 900 °C. Whereas the latter were, as expected, highly mesoporous carbons, the former cryogels had very different pore textures. Highly diluted cryogels allowed preparation of microporous materials with high surface areas, but activation of initially dense cryogels led to almost non-porous carbons, with much lower surface areas than those obtained by pyrolysis. The optimal acid concentration for activation, corresponding to stoichiometry between molecules of acid and hydroxyl groups, was 2 M l−1, and the acid–cryogel contact time also had an optimal value. Such optimization allowed us to achieve surface areas and micropore volumes among the highest ever obtained by activation with H3PO4, close to 2200 m2 g−1 and 0.7 cm3 g−1, respectively. Activation of diluted cryogels with a lower acid concentration of 1.2 M l−1 led to authentic bimodal activated carbons, having a surface area as high as 1780 m2 g−1 and 0.6 cm3 g−1 of microporous volume easily accessible through a widely developed macroporosity. PMID:27877405

Investigation of charge-transfer hydrogen bonding interaction of 1-(2-pyridylazo)-2-naphthol (PAN) and 4-(2-Pyridylazo)resorcinol (PAR) with chloranilic acid through experimental and DFT studies

NASA Astrophysics Data System (ADS)

Karmakar, Animesh; Singh, Bula

2018-07-01

The H-bonding interaction of 1-(2-pyridylazo)-2-naphthol (PAN) and 4-(2-Pyridylazo) resorcinol (PAR) with chloranilic acid (CLA) have been considered spectroscopically in methanol solvent. PAN and PAR were used as a ligand and this two ligands has diverse application in spectrophotometric, chelatometric analysis of different metal ions. However, it is seen as of the literature analysis that no molecular complex of PAN and PAR with CLA was reported. The creation of charge-transfer H-bonded adduct gives a outlook to progress the physico-chemical scenery of the donor. So the complex of PAN and PAR with chloranilic acid was recounted in this work in methanol medium. Both the hydrogen-bonded molecular complexes have been prepared and identified using 1H NMR, FT-IR, and elemental analysis. Spectroscopic data point out that PAN and PAR discretely interact with CLA by a physically potent H-bonding interaction. The thermal constancy of the above molecular complexes has been determined by TGA-DTA analysis. The computational calculation also supported the development of the H-bonded charge-transfer adduct.

Theoretical studies of structure and selectivity of 5-methyl-4-(2-thiazolylazo) resorcinol as a sensor for metal ions: DFT calculation

NASA Astrophysics Data System (ADS)

Thaomola, Sukhontip; Sompech, Supachai

2018-05-01

The global minimum optimized structures of the free sensor 5-methyl-4-(2-thiazolylazo) resorcinol (5-Me-TAR) and 5-Me-TAR-Cu2+ complexes in the gas phase have been investigated by using Density Functional Theory (DFT) with the def2-TZVP basis set. To compare the selectivity of 5-Me-TAR for metal ions, the binding energy of 5-Me-TAR with various metal ions (Na+, K+, Mg2+, Ca2+, Ba2+, Mn2+, Co2+, Ni2+, Cu2+, Zn2+, Pd2+, Cd2+ and Hg2+) were calculated at the same level as the theory. Binding energy values of most transition metal ions are lower than alkaline earth metal ions and alkali metal ions, respectively. The 5-Me-TAR sensor shows the highest selectivity with the Cu2+ ion. Moreover, Dependent Density Functional Theory (TDDFT) results confirm that the 5-Me-TAR-Cu2+ complex is stabilized by the sensor to metal charge transfer process. The computational studies suggested that the 5-Me-TAR is suitable for Cu2+ ion detection sensor development.

Quantitative Determination of α-Arbutin, β-Arbutin, Kojic Acid, Nicotinamide, Hydroquinone, Resorcinol, 4-Methoxyphenol, 4-Ethoxyphenol, and Ascorbic Acid from Skin Whitening Products by HPLC-UV.

PubMed

Wang, Yan-Hong; Avonto, Cristina; Avula, Bharathi; Wang, Mei; Rua, Diego; Khan, Ikhlas A

2015-01-01

An HPLC-UV method was developed for the quantitative analysis of nine skin whitening agents in a single injection. These compounds are α-arbutin, β-arbutin, kojic acid, nicotinamide, resorcinol, ascorbic acid, hydroquinone, 4-methoxyphenol, and 4-ethoxyphenol. The separation was achieved on a reversed-phase C18 column within 30 min. The mobile phase was composed of water and methanol, both containing 0.1% acetic acid (v/v). The stability of the analytes was evaluated at different pH values between 2.3 and 7.6, and the extraction procedure was validated for different types of skin whitening product matrixes, which included two creams, a soap bar, and a capsule. The best solvent system for sample preparation was 20 mM NaH2PO4 containing 10% methanol at pH 2.3. The analytical method was validated for accuracy, precision, LOD, and LOQ. The developed HPLC-UV method was applied for the quantitation of the nine analytes in 59 skin whitening products including creams, lotions, sera, foams, gels, mask sheets, soap bars, tablets, and capsules.

Studies on the Food Additive Propyl Gallate: Synthesis, Structural Characterization, and Evaluation of the Antioxidant Activity

ERIC Educational Resources Information Center

Garrido, Jorge; Garrido, E. Manuela; Borges, Fernanda

2012-01-01

Antioxidants are additives largely used in industry for delaying, retarding, or preventing the development of oxidative deterioration. Propyl gallate (E310) is a phenolic antioxidant extensively used in the food, cosmetics, and pharmaceutical industries. A series of lab experiments have been developed to teach students about the importance and…

Synthesis and Metalation of a Ligand: An Interdisciplinary Laboratory Experiment for Second-Year Organic and Introductory Inorganic Chemistry Students

ERIC Educational Resources Information Center

Kasting, Benjamin J.; Bowser, Andrew K.; Anderson-Wile, Amelia M.; Wile, Bradley M.

2015-01-01

An interdisciplinary laboratory experiment involving second-year undergraduate organic chemistry and introductory inorganic chemistry undergraduate students is described. Organic chemistry students prepare a series of amine-bis(phenols) via a Mannich reaction, and characterize their products using melting point; FTIR; and [superscript 1]H,…

Phenolic compositions of 50 and 30 year sequences of Australian red wines: the impact of wine age.

PubMed

McRae, Jacqui M; Dambergs, Robert G; Kassara, Stella; Parker, Mango; Jeffery, David W; Herderich, Markus J; Smith, Paul A

2012-10-10

The phenolic composition of red wine impacts upon the color and mouthfeel and thus quality of the wine. Both of these characteristics differ depending on the age of a wine, with the purple of young wines changing to brick red and the puckering or aggressive astringency softening in older wines. This study investigated the color parameters, tannin concentrations and tannin composition of a 50 year series of Cabernet Sauvignon wines from a commercial label as well as 30 year series of Cabernet Sauvignon and Shiraz wines from a separate commercial label to assess the impact of wine age on phenolic composition and concentration. The wine color density in wines of 40 to 50 years old was around 5 AU compared with 16 AU of wine less than 12 months old, which correlated well with the concentration of non-bleachable pigments and pigmented polymers. Conversely, the anthocyanin concentrations in 10 year old wines were substantially lower than that of recently bottled wines (around 100 mg/L compared with 627 mg/L, respectively), adding further evidence that non-bleachable pigments including pigmented polymers play a much larger role in long-term wine color than anthocyanins. No age-related trend was observed for tannin concentration, indicating that the widely noted softer astringency of older red wines cannot necessarily be directly related to lower concentrations of soluble wine tannin and is potentially a consequence of changes in tannin structure. Wine tannins from older wines were generally larger than tannins from younger wines and showed structural changes consistent with oxidation.

Microporosity development in phenolic resin-based mesoporous carbons for enhancing CO2 adsorption at ambient conditions

NASA Astrophysics Data System (ADS)

Choma, Jerzy; Jedynak, Katarzyna; Fahrenholz, Weronika; Ludwinowicz, Jowita; Jaroniec, Mietek

2014-01-01

Soft-templating method was used to prepare mesoporous carbons. The synthesis in the presence of hydrochloric and citric acids involved resorcinol and formaldehyde as carbon precursors and triblock copolymer Pluronic F127 as a template. The as-synthesized samples underwent carbonization in flowing nitrogen at various temperatures; namely 600 °C, 700 °C and 800 °C. Two routes were used to develop microporosity in the mesoporous carbons studied. The first one involved introduction of tetraethyl orthosilicate to the reaction system. After silica dissolution with NaOH, an increase in microporosity was observed. The second method, chemical activation with KOH at 700 °C, was explored as an alternative approach to create microporosity. It is noteworthy that the TEOS addition not only led to the development of microporosity but also to some improvement of mesoporosity. The post-synthesis KOH activation resulted in more significant increase in the microporosity as compared to the samples obtained by TEOS-assisted synthesis. The mesopore volume was somewhat lower for activated carbons as compared to that in mesoporous carbons. Both methods resulted in micro-mesoporous carbons with good adsorption properties; for instance, in the case of carbons prepared in the presence of TEOS, the best sample exhibited BET surface area of 1463 m2/g and the total pore volume of 1.31 cm3/g. For the KOH activated carbons the best adsorption parameters were as follows: the specific surface area = 1906 m2/g, and the total pore volume = 0.98 cm3/g. Both procedures used for microporosity development afforded carbons with good adsorption properties that can be useful for applications such as CO2 adsorption, air and water purification.

Improved Structural Design and CO 2 Capture of Porous Hydroxy-Rich Polymeric Organic Frameworks

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

Kidder, Michelle K.; Earl, Lyndsey D.; de Almeida, Valmor F.

2016-04-16

Polymeric organic frameworks (POFs) are tunable and robust porous materials with potential applications for gas capture, catalysis, and separations technologies. A series of new porous POFs have been synthesized from the reaction of phloroglucinol or resorcinol derivatives with aryl aldehyde precursors. The monomers have various molecular shapes including linear, bent, trigonal, and tetrahedral geometries. Depending on the size and geometric matching of the monomers, the polymers are dominantly microporous with some mesoporous character or they are non-porous. In addition to standard spectroscopic and surface characterization, the materials were screened as adsorbents for carbon dioxide capture at low pressure (0-1 bar).more » The best performing material (POF 1D) has a CO 2 capture capacity of 9.0 wt. % (2.04 mmol g -1) at 298 K and 1 bar which is comparable to other polymeric organic frameworks. Isosteric heats of adsorption for POF 1A, POF 2A, and POF 2B were found to be dependent on the weight percent of CO 2 adsorbed: this suggests there are both chemisorptive and physisorptive components of CO 2 capture by the POFs.« less

Phenolic aminocarboxylate chelates of 99mTc as hepatobiliary agents.

PubMed

Hunt, F C; Maddalena, D J; Wilson, J G; Bautovich, G J

1986-01-01

A series of alkyl- and halogen-substituted derivatives of ethylenediamine di[o-hydroxyphenylacetic acid] (EDDHA) and N,N'-bis[2-hydroxybenzyl] ethylenediamine N,N'-diacetic acid (HBED) were complexed with 99mTc and their biodistribution was determined in rats. All complexes displayed substantial hepatobiliary excretion; of each series, 99mTc-Br-EDDHA and 99mTc-di-Cl-HBED had the maximum amount in the gastrointestinal tract. Scintigraphic studies of 99mTc-Cl-EDDHA in dogs revealed prompt imaging of the liver followed by imaging of the gall bladder as the complex was excreted into the bile.

Carbon foams for energy storage devices

DOEpatents

Kaschmitter, James L.; Mayer, Steven T.; Pekala, Richard W.

1996-01-01

A high energy density capacitor incorporating a variety of carbon foam electrodes is described. The foams, derived from the pyrolysis of resorcinol-formaldehyde and related polymers, are high density (0.1 g/cc-1.0 g/cc) electrically conductive and have high surface areas (400 m.sup.2 /g-1000 m.sup.2 /g). Capacitances on the order of several tens of farad per gram of electrode are achieved.

Supercapacitors based on carbon foams

DOEpatents

Kaschmitter, James L.; Mayer, Steven T.; Pekala, Richard W.

1993-01-01

A high energy density capacitor incorporating a variety of carbon foam electrodes is described. The foams, derived from the pyrolysis of resorcinol-formaldehyde and related polymers, are high density (0.1 g/cc-1.0 g/cc) electrically conductive and have high surface areas (400 m.sup.2 /g-1000 m.sup.2 /g). Capacitances on the order of several tens of farad per gram of electrode are achieved.

Oxidative degradation of phenols in sono-Fenton-like systems upon high-frequency ultrasound irradiation

NASA Astrophysics Data System (ADS)

Aseev, D. G.; Sizykh, M. R.; Batoeva, A. A.

2017-12-01

The kinetics of oxidative degradation of phenol and chlorophenols upon acoustic cavitation in the megahertz range (1.7 MHz) is studied experimentally in model systems, and the involvement of in situ generated reactive oxygen species (ROSs) is demonstrated. The phenols subjected to high frequency ultrasound (HFUS) are ranked in terms of their rate of conversion: 2,4,6-trichlorophenol > 2,4-dichlorophenol 2-chlorophenol > 4-chlorophenol phenol. Oxidative degradation upon HFUS irradiation is most efficient at low concentrations of pollutants, due to the low steady-state concentrations of the in situ generated ROSs. A dramatic increase is observed in the efficiency of oxidation in several sonochemical oxidative systems (HFUS in combination with other chemical oxidative factors). The system with added Fe2+ (a sono-Fenton system) derives its efficiency from hydrogen peroxide generated in situ as a result of the recombination of OH radicals. The S2O8 2-/Fe2+/HFUS system has a synergetic effect on substrate oxidation that is attributed to a radical chain mechanism. In terms of the oxidation rates, degrees of conversion, and specific energy efficiencies of 4-chlorophenol oxidation based on the amount of oxidized substance per unit of expended energy the considered sonochemical oxidative systems form the series HFUS < S2O8 2-/HFUS < S2O8 2-/Fe2+/HFUS.

The oxidation degradation of aromatic compounds

NASA Technical Reports Server (NTRS)

Brezinsky, Kenneth; Glassman, Irvin

1987-01-01

A series of experiments were conducted which focused on understanding the role that the O atom addition to aromatic rings plays in the oxidation of benzene and toluene. Flow reactor studies of the oxidation of toluene gave an indication of the amount of O atoms available during an oxidation and the degree to which the O atom adds to the ring. Flow reactor studies of the oxidation of toluene and benzene to which NO2 was added, have shown that NO2 appears to suppress the formation of O atoms and consequently reduce the amount of phenols and cresols formed by O atom addition. A high temperature pyrolysis study of phenol has confirmed that the major decomposition products are carbon monoxide and cyclopentadiene. A preliminary value for the overall decomposition rate constant was also obtained.

Mushroom Tyrosinase: A Model System to Combine Experimental Investigation of Enzyme-Catalyzed Reactions, Data Handling Using R, and Enzyme-Inhibitor Structural Studies

ERIC Educational Resources Information Center

Nairn, Robert; Cresswell, Will; Nairn, Jacqueline

2015-01-01

The activity of mushroom tyrosinase can be measured by monitoring the conversion of phenolic compounds into quinone derivatives using spectrophotometry. This article describes a series of experiments which characterize the functional properties of tyrosinase, the analysis of the resulting data using R to determine the kinetic parameters, and the…

Extending the scope of amantadine drug by incorporation of phenolic azo Schiff bases as potent selective inhibitors of carbonic anhydrase II, drug likeness and binding analysis.

PubMed

Channar, Pervaiz Ali; Saeed, Aamer; Shahzad, Danish; Larik, Fayaz Ali; Hassan, Mubashir; Raza, Hussain; Abbas, Qamar; Seo, Sung-Yum

2018-05-16

A series of Amantadine based azo Schiff base dyes 6a-6e have been synthesized and characterized by 1 H NMR and 13 C NMR and evaluated for their in vitro carbonic anhydrase II inhibition activity and antioxidant activity. All of the synthesized showed excellent carbonic inhibition. Compound 6b was found to be the most potent derivative in the series, the IC 50 of 6b was found to be 0.0849 ± 0.00245μM (standard Acetazolamide IC 50 =0.9975±0.049μM). The binding interactions of the most active analogs were confirmed through molecular docking studies. Docking studies showed 6b is interacting by making two hydrogen bonds w at His93 and Ser1 residues respectively. All compounds showed a good drug score and followed Lipinski's rule. In summary, our studies have shown that these amantadine derived phenolic azo Schiff base derivatives are a new class of carbonic anhydrase II inhibitors. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

Diagenesis of conifer needles in a coastal marine environment

NASA Astrophysics Data System (ADS)

Hedges, John I.; Weliky, K.

1989-10-01

Physically intact fir, hemlock and cedar needles were isolated from different horizons of a sediment core from a coastal marine bay (Dabob Bay, Washington State, U.S.A.) and from nearby trees and forest litter. Green fir, hemlock and cedar needles were all characterized by glucose-rich aldose mixtures (~30% of tissue carbon), the production of vanillyl and cinnamyl CuO-derived phenols (~8% of tissue carbon) and the presence of both pinitol and myo-inositol (1-2% of tissue carbon). Needles from forest litter were enriched in lignin phenols and non-glucose aldoses and depleted in glucose and cyclitols. The sediment core contained an average of 10 mg/1 of physically intact fir, hemlock and cedar needles, which occurred in similar relative abundances and accounted for less than 1% of the total nonwoody gymnosperm tissue. Compared to the green and litter counterparts, all sedimentary needles were greatly depleted in cyclitols, glucose and p-coumaric acid and enriched in vanillyl phenol precursors. The degree of elevation of vanillyl phenol yield from the degraded needles was used to estimate minimal carbon losses from the samples, which ranged from near 40% for needle litter to almost 70% for the deepest (~100 years old) sedimentary fir/hemlock samples. Although downcore increases in carbon loss and refractory organic components indicated in situ diagenesis, the bulk of overall degradation occurred either on land or during the first 10-20 years after deposition. Atomic C/N ratios of degraded needles were lower than for green counterparts, but nitrogen was lost overall. These relative changes indicate the following stability series: vanillyl phenols > N > ferulic acid, p-hydroxy phenols, most aldoses and bulk tissue > glucose and p-coumaric acid > cyclitols (near 100% loss). Vanillic acid to vanillin ratios, (Ad/Al)v, of the green fir and hemlock needles were unusually high (0.36-0.38) and decreased downcore. Diagenesis also decreased the cinnamyl/vanillyl phenol ratio (C/V) of the deepest sedimentary fir/hemlock needles to 20% of the original value and almost tripled the carbon-normalized yield of total vanillyl plus cinnamyl phenols (Λ). The net result of these compositional variations was to make the lignin component of the buried conifer needles resemble lignin in gymnosperm wood, thereby leading to underestimates of needle input and mass.

Synthesis of porous g-C{sub 3}N{sub 4}/La and enhanced photocatalytic activity for the degradation of phenol under visible light irradiation

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

Rong, Xinshan; Qiu, Fengxian, E-mail: fxqiu@ujs.edu.cn; Rong, Jian

2015-10-15

A series of porous g-C{sub 3}N{sub 4}/La (PGCN/La) materials used as photocatalyst for the degradation of phenol were prepared by two steps. The photocatalysts were characterized by X-ray diffraction (XRD), UV–vis diffuse reflectance spectroscopy (DRS), thermogravimetry (TG), Brunauer–Emmett–Teller (BET), Scanning electron microscopy (SEM), transmission electron microscopy (TEM) and X-ray photoelectron spectroscopy (XPS). From the TEM morphology, the porous structure of g-C{sub 3}N{sub 4} could be successfully controlled; from BET results, BET specific surface area of porous g-C{sub 3}N{sub 4} (PGCN) sample increases with the increasing of urea mass ratio. Compared with PGCN material (PGCN-50), PGCN/La sample (PGCN-50/La-5) could exhibit anmore » enhanced photocatalytic activity and has the best degradation efficiency of 98.6% within 50 min under visible light irradiation. Photocatalytic reaction follows the first-order model kinetics; and PGCN-50/La-5 photocatalyst shows the largest reaction rate among all samples which is nearly 2.96 times higher than that of pure PGCN-50. The present work illustrates that the photocatalytic activity of porous g-C{sub 3}N{sub 4} was improved by the addition of La and PGCN-50/La-5 has potential application in the removal of phenol or other organic molecular from wastewater. - Graphical abstract: Porous g-C{sub 3}N{sub 4}/La photocatalyst is synthesized and its removal of phenol application has been explored. - Highlights: • Porous PGCN/La photocatalyst was prepared successfully by hydrothermal method. • PGCN/La has a highest degradation efficiency of 98.6% for phenol within 50 min. • The reaction rate of is nearly 2.96 times higher than that of pure PGCN. • As prepared material has potential application in removal of phenol from wastewater.« less

Assessment of increased wet wood bonding for epoxy-bonded samples using a melamine-urea-formaldehyde priming agent

Treesearch

Jermal G. Chandler; Charles R. Frihart

2005-01-01

Is the hydroxymethylated resorcinol (HMR) primer unique or can a melamine- based primer also increase the wet wood strength of epoxy bonds? Although the exact reason for poor durability with some wood adhesives is not known, the HMR priming agent was found to facilitate durable bonds in most cases tested. A model of cell wall stabilization that is believed to be the...

Process for producing carbon foams for energy storage devices

DOEpatents

Kaschmitter, James L.; Mayer, Steven T.; Pekala, Richard W.

1998-01-01

A high energy density capacitor incorporating a variety of carbon foam electrodes is described. The foams, derived from the pyrolysis of resorcinol-formaldehyde and related polymers, are high density (0.1 g/cc-1.0 g/cc) electrically conductive and have high surface areas (400 m.sup.2 /g-1000 m.sup.2 /g). Capacitances on the order of several tens of farad per gram of electrode are achieved.

Carbon foams for energy storage devices

DOEpatents

Kaschmitter, J.L.; Mayer, S.T.; Pekala, R.W.

1996-06-25

A high energy density capacitor incorporating a variety of carbon foam electrodes is described. The foams, derived from the pyrolysis of resorcinol-formaldehyde and related polymers, are high density (0.1 g/cc--1.0 g/cc) electrically conductive and have high surface areas (400 m{sup 2}/g-1000 m{sup 2}/g). Capacitances on the order of several tens of farad per gram of electrode are achieved. 9 figs.

Supercapacitors based on carbon foams

DOEpatents

Kaschmitter, J.L.; Mayer, S.T.; Pekala, R.W.

1993-11-09

A high energy density capacitor incorporating a variety of carbon foam electrodes is described. The foams, derived from the pyrolysis of resorcinol-formaldehyde and related polymers, are high density (0.1 g/cc-1.0 g/cc) electrically conductive and have high surface areas (400 m[sup 2]/g-1000 m[sup 2]/g). Capacitances on the order of several tens of farad per gram of electrode are achieved. 9 figures.

[Investigation on simultaneous determination of dihydroxybenzene isomers in water samples using multi-walled carbon nanotube modified screen-printed electrode].

PubMed

Li, Yuan-Ting; Li, Da-Wei; Song, Wei; Long, Yi-Tao

2011-02-01

A disposable electrode, multi-walled carbon nanotube modified screen printed electrode (MWCNT/SPE), had been fabricated using screen printing technology and drop-coating method to determine dihydroxybenzene isomers (hydroquinone, catechol and resorcinol). The cyclic voltammetry behavior of dihydroxybenzene isomers had been investigated with the MWCNT/SPE. The results reveal that MWCNT/SPE, which shows a strong electrocatalytic activity for the oxidation of dihydroxybenzenes, can entirely separate the oxidation peaks of them. According to differential pulse voltammetry tests, the peak currents of dihydroxybenzene isomers are linear to their concentrations at the range of 8.20 x 10(-6) -1.00 x 10(-3), 8.20 x 10(-6) -1.00 x 10(-3) and 1.64 x 10(-5) -1.16 x 10(-3) mol x L(-1), with the detection limits of 4.34 x 10(-6), 3.42 x 10(-6) and 6.70 x 10(-6) mol x L(-1) for hydroquinone, catechol and resorcinol, respectively. For the determination of dihydroxybenzene isomers in water samples, the value of recovery found by standard addition method was in the range of 96.2%-104.9%. These results indicate MWCNT/SPE can be applied to rapid in-situ determination of dihydroxybenzenes-polluted water samples.

Fire Safety Tests for Cesium-Loaded Spherical Resorcinol Formaldehyde Resin: Data Summary Report

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

Kim, Dong-Sang; Schweiger, Michael J.; Peterson, Reid A.

2012-09-01

A draft safety evaluation of the scenario for spherical resorcinol formaldehyde (SRF) resin fire inside the ion exchange column was performed by the Hanford Tank Waste Treatment and Immobilization Plant (WTP) Fire Safety organization. The result of this draft evaluation suggested a potential change of the fire safety classification for the Cesium Ion Exchange Process System (CXP) emergency elution vessels, equipment, and piping. To resolve this question, the fire properties of the SRF resin were measured by Southwest Research Institute (SwRI) through a subcontract managed by Pacific Northwest National Laboratory (PNNL). The results of initial fire safety tests on themore » SRF resin were documented in a previous report (WTP-RPT-218). The present report summarizes the results of additional tests performed by SwRI on the cesium-loaded SRF resin. The efforts by PNNL were limited to summarizing the test results provided by SwRI into one consolidated data report. The as-received SwRI report is attached to this report in the Appendix A. Where applicable, the precision and bias of each test method, as given by each American Society for Testing and Materials (ASTM) standard procedure, are included and compared with the SwRI test results of the cesium-loaded SRF resin.« less

Skin sensitization quantitative risk assessment for occupational exposure of hairdressers to hair dye ingredients.

PubMed

Goebel, Carsten; Diepgen, Thomas L; Blömeke, Brunhilde; Gaspari, Anthony A; Schnuch, Axel; Fuchs, Anne; Schlotmann, Kordula; Krasteva, Maya; Kimber, Ian

2018-06-01

Occupational exposure of hairdressers to hair dyes has been associated with the development of allergic contact dermatitis (ACD) involving the hands. p-Phenylenediamine (PPD) and toluene-2,5-diamine (PTD) have been implicated as important occupational contact allergens. To conduct a quantitative risk assessment for the induction of contact sensitization to hair dyes in hairdressers, available data from hand rinsing studies following typical occupational exposure conditions to PPD, PTD and resorcinol were assessed. By accounting for wet work, uneven exposure and inter-individual variability for professionals, daily hand exposure concentrations were derived. Secondly, daily hand exposure was compared with the sensitization induction potency of the individual hair dye defined as the No Expected Sensitization Induction Levels (NESIL). For PPD and PTD hairdresser hand exposure levels were 2.7 and 5.9 fold below the individual NESIL. In contrast, hand exposure to resorcinol was 50 fold below the NESIL. Correspondingly, the risk assessment for PPD and PTD indicates that contact sensitization may occur, when skin protection and skin care are not rigorously applied. We conclude that awareness of health risks associated with occupational exposure to hair dyes, and of the importance of adequate protective measures, should be emphasized more fully during hairdresser education and training. Copyright © 2018 Elsevier Inc. All rights reserved.

4-(2-Pyridylazo)-resorcinol Functionalized Thermosensitive Ionic Microgels for Optical Detection of Heavy Metal Ions at Nanomolar Level.

PubMed

Zhou, Xianjing; Nie, Jingjing; Du, Binyang

2015-10-07

4-(2-Pyridylazo)-resorcinol (PAR) functionalized thermosensitive ionic microgels (PAR-MG) were synthesized by a one-pot quaternization method. The PAR-MG microgels were spherical in shape with radius of ca. 166.0 nm and narrow size distribution and exhibited thermo-sensitivity in aqueous solution. The PAR-MG microgels could optically detect trace heavy metal ions, such as Cu(2+), Mn(2+), Pb(2+), Zn(2+), and Ni(2+), in aqueous solutions with high selectivity and sensitivity. The PAR-MG microgel suspensions exhibited characteristic color with the presence of various trace heavy metal ions, which could be visually distinguished by naked eyes. The limit of colorimetric detection (DL) was determined to be 38 nM for Cu(2+) at pH 3, 12 nM for Cu(2+) at pH 7, and 14, 79, 20, and 21 nM for Mn(2+), Pb(2+), Zn(2+), and Ni(2+), respectively, at pH 11, which was lower than (or close to) the United States Environmental Protection Agency standard for the safety limit of these heavy metal ions in drinking water. The mechanism of detection was attributed to the chelation between the nitrogen atoms and o-hydroxyl groups of PAR within the microgels and heavy metal ions.

Cycloate, an inhibitor of fatty acid elongase, modulates the metabolism of very-long-side-chain alkylresorcinols in rye seedlings.

PubMed

Magnucka, Elzbieta G; Suzuki, Yoshikatsu; Pietr, Stanislaw J; Kozubek, Arkadiusz; Zarnowski, Robert

2009-10-01

Cycloate inhibits the biosynthesis of very-long-chain fatty acids, the essential constituents of plant waxes and suberin. Fatty acids also serve as precursors of aliphatic carbon chains in resorcinolic lipids, which play a fundamental role in the plant defence system against fungal pathogens. In this study, the effect of cycloate on the biosynthesis of 5-n-alkylresorcinols in rye seedlings (Secale cereale L.) grown under various light and thermal conditions was examined. The content of alkylresorcinols biosynthesised in rye was generally increased by the herbicide in both green and etiolated plants. The presence of cycloate also affected patterns of alkylresorcinol homologues in plants grown at 15 and 22 degrees C; very-long-side-chain compounds were less abundant, whereas both short-chain saturated and unsaturated homologues were generally accumulated. No cycloate-related effects caused by homologue pattern modifications were observed at elevated temperature. This study extends present understanding of the mode of action of thiocarbamate herbicides. Cycloate markedly affected the biosynthesis of very-long-side-chain resorcinolic lipids in rye seedlings, confirming the existence of parallels in both fatty acid and alkylresorcinol biosynthetic pathways. The observed cycloate-driven accumulation of 5-n-alkylresorcinols may improve the resistance of cereals to infections caused by microbial pathogens. Copyright 2009 Society of Chemical Industry.

Synthesis, structure and luminescence of novel co-crystals based on bispyridyl-substituted α,β-unsaturated ketones with coformers

NASA Astrophysics Data System (ADS)

Li, Hong-Juan; Wang, Lei; Zhao, Juan-Juan; Sun, Ju-Feng; Sun, Ji-Liang; Wang, Chun-Hua; Hou, Gui-Ge

2015-01-01

Based on 2,6-bis((pyridin-4-yl)methylene)cyclohexanone (A) and N-methyl-3,5-bis((pyridin-4-yl)methylene)-4-piperidone (B) with coformers, three novel macrocyclic co-crystals, (A)ṡ(resorcinol) (1), (A)ṡ(1,3,5-benzenetriol) (2), (B)2ṡ(1,3,5-benzenetriol)2 (3) and three chain co-crystals, (A)ṡ(hydroquinone) (4), (A)ṡ(isophthalic acid) (5), (B)ṡ(isophthalic acid) (6) have been synthesized and structurally characterized by IR, 1H NMR and X-ray crystal structure analysis. Structural analysis indicates that four-component macrocycles in 1-3 are generated from "clip-like" resorcinol templates and building blocks, while 4-6 show infinite H-bonding chains. In addition, the luminescent properties of A, B and 1-6 are investigated primarily in the solid state. Compared with free building blocks, 1-6 are blue-shifted 55-60 nm with decreasing emission intensities in spite of the enhancement in 6. The change of luminescent properties might be caused mainly by incorporation of coformers into co-crystals, including H-bonds, molecular conformations, arranging dispositions and π-π characteristics. It might have potential applications for crystal engineering to construct patentable crystals with interesting luminescent properties.

Simultaneous determination of hydroquinone, catechol and resorcinol by voltammetry using graphene screen-printed electrodes and partial least squares calibration.

PubMed

Aragó, Miriam; Ariño, Cristina; Dago, Àngela; Díaz-Cruz, José Manuel; Esteban, Miquel

2016-11-01

Catechol (CC), resorcinol (RC) and hydroquinone (HQ) are dihydroxybenzene isomers that usually coexist in different samples and can be determined using voltammetric techniques taking profit of their fast response, high sensitivity and selectivity, cheap instrumentation, simple and timesaving operation modes. However, a strong overlapping of CC and HQ signals is observed hindering their accurate analysis. In the present work, the combination of differential pulse voltammetry with graphene screen-printed electrodes (allowing detection limits of 2.7, 1.7 and 2.4µmolL(-1) for HQ, CC and RC respectively) and the data analysis by partial least squares calibration (giving root mean square errors of prediction, RMSEP values, of 2.6, 4.1 and 2.3 for HQ, CC and RC respectively) has been proposed as a powerful tool for the quantification of mixtures of these dihydroxybenzene isomers. The commercial availability of the screen-printed devices and the low cost and simplicity of the analysis suggest that the proposed method can be a valuable alternative to chromatographic and electrophoretic methods for the considered species. The method has been applied to the analysis of these isomers in spiked tap water. Copyright © 2016 Elsevier B.V. All rights reserved.

Antibody-based enzyme-linked lectin assay (ABELLA) for the sialylated recombinant human erythropoietin present in culture supernatant.

PubMed

Kim, Hyoung Jin; Lee, Seung Jae; Kim, Hong-Jin

2008-11-04

The terminal sialic acid of human erythropoietin (hEPO) is essential for in vivo activity. The current resorcinol and HPLC methods for analyzing alpha2,3-linked sialic acid require more than a microgram of purified rhEPO, and purification takes a great deal of time and labor. In this study, we assessed the use of an antibody-based enzyme-linked lectin assay (ABELLA) for analyzing non-purified recombinant hEPO (rhEPO). The major problem of this method was the high background due to terminal sialylation of components of the assay (antibody and bovine serum albumin) other than rhEPO. To solve this problem, we used a monoclonal antibody (Mab 287) to capture the rhEPO, and oxidized the bovine serum albumin used for blocking with meta-periodate. The sialic acid content of non-purified rhEPO measured by ABELLA was similar to that obtained by the resorcinol method on purified rhEPO. ABELLA has advantages such as adaptability and need for minimal amounts of rhEPO (40 ng/ml). Our observations suggest that ABELLA should reduce the time and labor needed to improve culture conditions so as to increase protein sialylation, and also facilitate the study of sialylation mechanisms.

Studies on the precursors of strong mutagen [3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone]MX by chlorination of fractions from different waters.

PubMed

Xu, X; Liang, L; Zou, H; Liu, Y; Wang, L; Zhang, J

1997-10-01

The strong mutagen, [3-chloro-4-(dichloromethyl)-5-hydroxy- 2(5H)-furanone] MX, was found to be one of the most potent mutagens in drinking water. In this study, dissolved organic matters from river water and lake water were separated into several compound classes by sorbtion on a series of resin absorbents. After chlorine treatment of the fractions, MX was determined with GC/MS in the selected ion monitoring mode. Humic substances produced more MX on a TOC-basis than other fractions and contributed more to MX formation in the chlorinated natural waters. Some phenols were detected in the oxidation products of humic substances and therefore formation of MX may occur when some phenolic precursor structures in humic substances are treated with chlorine.

In vitro antioxidant activities of leaf and root extracts of Albizia antunesiana harms.

PubMed

Chipiti, Talent; Ibrahim, Mohammed Auwal; Koorbanally, Neil Anthony; Islam, Md Shahidul

2013-01-01

The antioxidative activities of the ethanol and aqueous extracts of the leaf and root samples of Albizia antunesiana were determined across a series of four in vitro models. The results showed that all the extracts had reducing power (Fe(3+)- Fe2+), DPPH, hydroxyl and nitric oxide radical scavenging abilities. The ethanol root extract had more potent antioxidant power in all the experimental models and possesses a higher total phenol content of 216.6 +/- 6.7 mg/g. The GC-MS analysis of the aqueous and ethanol extracts of the roots and leaves indicated that several aromatic phenolic compounds, a coumarin and some common triterpenoids were present in these extracts. Data from this study suggest that the leaves and roots of Albizia antunesiana possessed antioxidative activities that varied depending on the solvents.

Enhanced photocatalytic degradation of phenol and photogenerated charges transfer property over BiOI-loaded ZnO composites.

PubMed

Jiang, Jingjing; Wang, Hongtao; Chen, Xiaodong; Li, Shuo; Xie, Tengfeng; Wang, Dejun; Lin, Yanhong

2017-05-15

In this paper, a series of BiOI/ZnO photocatalysts containing various BiOI contents were prepared by a facile two-step synthetic method. The structure and crystal phase, morphology, surface element analysis, optical property of as-prepared samples are measured by X-ray diffraction (XRD), Scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS) and UV-Vis diffuse reflectance spectrometry (DRS). BiOI/ZnO photocatalytic activities of the prepared photocatalysts were evaluated by photocatalytic degradation of phenol under simulated light irradiation. The phenol degradation rate reached 99.9% within 2h under simulated solar light irradiation. The probable photocatalytic mechanism of composites photocatalysts is discussed by active species trapping experiments, the surface photovoltage (SPV), the transient photovoltage (TPV) and photoluminescence (PL) measurements. The results manifest that the superior photocatalytic activity of BiOI/ZnO composites is derived from the strong internal electric field between BiOI and ZnO, which is beneficial for the effective separation and transfer of photogenerated charges in ZnO. Moreover, the loading of BiOI on the surface of ZnO inhibited the recombination of photogenerated charge carriers in ZnO, resulting in excellent photocatalytic activity. On the contrary, the effect of an extension of the light absorption range induced by the introduction of BiOI on the phenol degradation activity is not significant. Copyright © 2017 Elsevier Inc. All rights reserved.

Process for producing carbon foams for energy storage devices

DOEpatents

Kaschmitter, J.L.; Mayer, S.T.; Pekala, R.W.

1998-08-04

A high energy density capacitor incorporating a variety of carbon foam electrodes is described. The foams, derived from the pyrolysis of resorcinol-formaldehyde and related polymers, are high density (0.1 g/cc--1.0 g/cc) electrically conductive and have high surface areas (400 m{sup 2}/g--1,000 m{sup 2}/g). Capacitances on the order of several tens of farad per gram of electrode are achieved. 9 figs.

Fine structure in the m/z 121 mass chromatogram of Paraho shale oil

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

Gallegos, E.J.

1984-04-01

High-resolution gas chromatography/high-resolution mass spectrometry/computer (HRGC/HRMS/C) techniques are reported here in the provisional identification of several homologous series of alkylpuridines, phenols, terpenes, and terpanes analytically isolated from Paraho shale oil. HRGC/HRMS/C techniques were also used to follow the hydrodenitrification, HDN, procedure for the removal of the heterocompounds, as well as to monitor the effect of hydrogenation on alkenes.

Coupling the Alkaline-Surfactant-Polymer Technology and the Gelation Technology to Maximize Oil Production

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

Malcolm Pitts; Jie Qi; Dan Wilson

2005-12-01

Gelation technologies have been developed to provide more efficient vertical sweep efficiencies for flooding naturally fractured oil reservoirs or reservoirs with different sand lenses with high permeability contrast. The field proven alkaline-surfactant-polymer technology economically recovers 15% to 25% OOIP more crude oil than waterflooding froin swept pore space of an oil reservoir. However, alkaline-surfactant-polymer technology is not amenable to naturally fractured reservoirs or reservoirs with high permeability contrast zones because much of injected solution bypasses target pore space containing oil. This work investigates whether combining these two technologies could broaden applicability of alkaline-surfactant-polymer flooding into these reservoirs. Fluid-fluid interaction withmore » different gel chemical compositions and alkaline-surfactant-polymer solution with pH values ranging from 9.2 to 12.9 have been tested. Aluminum-polyacrylamide gels are not stable to alkaline-surfactant-polymer solutions at any pH. Chromium-polyacrylamide gels with polymer to chromium ion ratios of 25 or greater were stable to alkaline-surfactant-polymer solutions if solution pH was 10.6 or less. When the polymer to chromium ion was 15 or less, chromium-polyacrylamide gels were stable to alkaline-surfactant-polymer solutions with pH values up to 12.9. Chromium-xanthan gum gels were stable to alkaline-surfactant-polymer solutions with pH values of 12.9 at the polymer to chromium ion ratios tested. Silicate-polyacrylamide, resorcinol-formaldehyde, and sulfomethylated resorcinol-formaldehyde gels were also stable to alkaline-surfactant-polymer solutions with pH values ranging from 9.2 to 12.9. Iron-polyacrylamide gels were immediately destroyed when contacted with any of the alkaline-surfactant-polymer solutions with pH values ranging from 9.2 to 12.9. Gel solutions under dynamic conditions of linear corefloods showed similar stability to alkaline-surfactant-polymer solutions as in the fluid-fluid analyses with the exception of the xanthan gum-chromium acetate gels. Aluminum-polyacrylamide flowing gels are not stable to alkaline-surfactant-polymer solutions of either pH 10.5 or 12.9, either in linear corefloods or in dual separate radial core, common manifold corefloods. Chromium acetate-polyacrylamide flowing and rigid tonguing gels are stable to subsequent alkaline-surfactant-polymer solution injection. Rigid tonguing chromium acetate-polyacrylamide gels maintained permeability reduction better than flowing chromium acetate-polyacrylamide gels. Chromium acetate gels were stable to injection of alkaline-surfactant-polymer solutions at 72 F, 125 F and 175 F in linear corefloods. Chromium acetate-polyacrylamide gels maintained diversion capability after injection of an alkaline-surfactant-polymer solution in stacked; radial coreflood with a common well bore. Chromium acetate-polyacrylamide gel used to seal fractured core maintain fracture closure if followed by an alkaline-surfactant-polymer solution. Chromium acetate-xanthan gum rigid gels are not stable to subsequent alkaline-surfactant-polymer solution injection at 72, 125, and 175 F. Silicate-polyacrylamide gels are not stable with subsequent injection of either a pH 10.5 or a 12.9 alkaline-surfactant-polymer solution. Resorcinol-formaldehyde gels were stable to subsequent alkaline-surfactant-polymer solution injection. When evaluated in a dual core configuration, injected fluid flows into the core with the greatest effective permeability to the injected fluid. The same gel stability trends to subsequent alkaline-surfactant-polymer injected solution were observed. Aluminum citrate-polyacrylamide, resorcinol-formaldehyde, and the silicate-polyacrylamide gel systems did not produce significant incremental oil in linear corefloods. Both flowing and rigid tonguing chromium acetate-polyacrylamide gels and the xanthan gum-chromium acetate gel system produced incremental oil with the rigid tonguing gel producing the greatest amount. Higher oil recovery could have been due to higher differential pressures across cores. Aluminum citrate-polyacrylamide gels, chromium acetate-polyacrylamide gels, silicate-polymer, and chromium-xanthan guin gels did not alter an alkaline-surfactant-polymer solution's ability to produce incremental oil. Incremental oil was reduced with the resorcinol-formaldehyde gel system. Total waterflood plus chemical flood oil recovery sequence recoveries were generally similar.« less

Predicting reactivity of model DOM compounds towards chlorine with mediated electrochemical oxidation.

PubMed

de Vera, Glen Andrew; Gernjak, Wolfgang; Radjenovic, Jelena

2017-05-01

Chlorine demand of a water sample depends on the characteristics of dissolved organic matter (DOM). It is an important parameter for water utilities used to assess oxidant and/or disinfectant consumption of source waters during treatment and distribution. In this study, model compounds namely resorcinol, tannic acid, vanillin, cysteine, tyrosine, and tryptophan were used to represent the reactive moieties of complex DOM mixtures. The reactivity of these compounds was evaluated in terms of Cl 2 demand and electron donating capacity (EDC). The EDC was determined by mediated electrochemical oxidation (MEO) which involves the use of 2,2'-azino-bis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) as an electron shuttle. The Cl 2 demand of readily oxidizable compounds (resorcinol, tannic acid, vanillin, and cysteine) was found to correlate well with EDC (R 2  = 0.98). The EDC values (mol e - /mol C) of the model compounds are as follows: 1.18 (cysteine) > 0.77 (resorcinol) > 0.59 (vanillin) > 0.52 (tannic acid) > 0.36 (tryptophan) > 0.19 (tyrosine). To determine the effect of pre-oxidation on EDC, ozone was added (0.1 mol O 3 /mol C) into each model compound solution. Ozonation caused a general decrease in EDC (10-40%), chlorine demand (10-30%), and UV absorbance (10-40%), except for tyrosine which showed both increased UV 275 and EDC. Before and after ozonation, 24 h disinfection byproduct (DBP) formation potential tests (Cl 2 residual = 1.5 mg/L) were conducted to evaluate the use of EDC for DBP formation prediction. The results indicate that there was no significant correlation between the EDC of the model compounds and the formation potentials of adsorbable organic chlorine, trichloromethane, and trichloroacetic acid. This suggests that while EDC correlates with Cl 2 demand, chlorine consumption may not directly translate to DBP formation because oxidation reactions may dominate over substitution reactions. Overall, this study provides useful insights on the reactions of ABTS + and HOCl with model DOM compounds, and highlights the potential application of MEO for rapid determination of Cl 2 demand of a water sample. Copyright © 2017 Elsevier Ltd. All rights reserved.

Investigation of Performance Envelope for Phenolic Impregnated Carbon Ablator (PICA)

NASA Technical Reports Server (NTRS)

Agrawal, Parul; Prabhu, Dinesh; Milos, Frank S.; Stackpoole, Mairead

2016-01-01

The present work provides the results of a short exploratory study on the performance of Phenolic Impregnated Carbon Ablator, or PICA, at high heat flux and pressure in an arcjet facility at NASA Ames Research Center. The primary objective of the study was to explore the thermal response of PICA at cold-wall heat fluxes well in excess of 1500 W/cm (exp 2). Based on the results of a series of flow simulations, multiple PICA samples were tested at an estimated cold wall heat flux and stagnation pressure of 1800 W/cm (exp 2) and 130 kPa, respectively. All samples survived the test, and no failure was observed either during or after the exposure. The results indicate that PICA has a potential to perform well at environments with significantly higher heat flux and pressure than it has currently been flown.

Structural dissection of Shewanella oneidensis old yellow enzyme 4 bound to a Meisenheimer complex and (nitro)phenolic ligands.

PubMed

Elegheert, Jonathan; Brigé, Ann; Van Beeumen, Jozef; Savvides, Savvas N

2017-10-01

Shewanella oneidensis, a Gram-negative γ-proteobacterium with an extensive redox capacity, possesses four old yellow enzyme (OYE) homologs. Of these, Shewanella yellow enzyme 4 (SYE4) is implicated in resistance to oxidative stress. Here, we present a series of high-resolution crystal structures for SYE4 in the oxidized and reduced states, and in complex with phenolic ligands and the nitro-aromatic explosive picric acid. The structures unmask new features, including the identification of a binding platform for long-chain hydrophobic molecules. Furthermore, we present the first structural observation of a hydride-Meisenheimer complex of picric acid with a flavoenzyme. Overall, our study exposes the binding promiscuity of SYE4 toward a variety of electrophilic substrates and is consistent with a general detoxification function for SYE4. © 2017 Federation of European Biochemical Societies.

Improved solubility of DNA in recyclable and reusable bio-based deep eutectic solvents with long-term structural and chemical stability.

PubMed

Mondal, Dibyendu; Sharma, Mukesh; Mukesh, Chandrakant; Gupta, Vishal; Prasad, Kamalesh

2013-10-25

The solubility of DNA in bio-based deep eutectic solvents (DESs) consisting of mixtures of choline chloride with levulinic acid, glycerol, ethylene glycol, sorbitol and resorcinol was investigated. The macromolecule was found to be soluble and chemically and structurally stable in DESs consisting of mixtures containing glycerol and ethylene glycol. Furthermore recyclability of the DESs was demonstrated over three consecutive reuses in DNA dissolution.

A simple and low cost dual-wavelength β-correction spectrophotometric determination and speciation of mercury(II) in water using chromogenic reagent 4-(2-thiazolylazo) resorcinol

NASA Astrophysics Data System (ADS)

Al-Bagawi, A. H.; Ahmad, W.; Saigl, Z. M.; Alwael, H.; Al-Harbi, E. A.; El-Shahawi, M. S.

2017-12-01

The most common problems in spectrophotometric determination of various complex species originate from the background spectral interference. Thus, the present study aimed to overcome the spectral matrix interference for the precise analysis and speciation of mercury(II) in water by dual-wavelength β-correction spectrophotometry using 4-(2-thiazolylazo) resorcinol (TAR) as chromogenic reagent. The principle was based on measuring the correct absorbance for the formed complex of mercury(II) ions with TAR reagent at 547 nm (lambda max). Under optimized conditions, a linear dynamic range of 0.1-2.0 μg mL- 1 with correlation coefficient (R2) of 0.997 were obtained with lower limits of detection (LOD) of 0.024 μg mL- 1 and limit of quantification (LOQ) of 0.081 μg mL- 1. The values of RSD and relative error (RE) obtained for β-correction method and single wavelength spectrophotometry were 1.3, 1.32% and 4.7, 5.9%, respectively. The method was validated in tap and sea water in terms of the data obtained from inductively coupled plasma-optical emission spectrometry (ICP-OES) using student's t and F tests. The developed methodology satisfactorily overcomes the spectral interference in trace determination and speciation of mercury(II) ions in water.

A glassy carbon electrode modified with cerium phosphate nanotubes for the simultaneous determination of hydroquinone, catechol and resorcinol.

PubMed

Li, Zhen; Yue, Yuhua; Hao, Yanjun; Feng, Shun; Zhou, Xianli

2018-03-12

A nafion film containing cerium phosphate nanotubes was pasted onto a glassy carbon electrode (GCE) to obtain a sensor for hydroquinone (HQ). The morphologies and components of the coating were characterized by transmission electron microscopy, scanning electron microscopy and energy-dispersive spectroscopy. Cyclic voltammetry and differential pulse voltammetry (DPV) showed the specific surface of the electrode to be significantly increased and the electron transfer rate to be accelerated. The modified GCE was applied to the determination of hydroquinone (HQ) via DPV. The oxidation current increases linearly in the 0.23 μM to 16 mM HQ concentration range which is as wide as five orders of magnitude. The limit of detection is 0.12 μM (based on a signal-to-noise ratio of 3), and the sensitivity is 1.41 μA·μM -1  cm -2 . The method was further applied to the simultaneous determination of HQ, catechol and resorcinol. The potentials for the three species are well separated (20, 134, and 572 mV vs SCE). Average recoveries from (spiked) real water samples are between 95.2 and 107.0%, with relative standard deviations of 0.9~2.7% (for n = 3) at three spiking levels. The method was validated by independent assays using HPLC. Graphical abstract ᅟ.

Prevalence of potent skin sensitizers in oxidative hair dye products in Korea.

PubMed

Kim, Hyunji; Kim, Kisok

2016-09-01

The objective of the present study was to elucidate the prevalence of potent skin sensitizers in oxidative hair dye products manufactured by Korean domestic companies. A database on hair dye products made by domestic companies and selling in the Korean market in 2013 was used to obtain information on company name, brand name, quantity of production, and ingredients. The prevalence of substances categorized as potent skin sensitizers was calculated using the hair dye ingredient database, and the pattern of concomitant presence of hair dye ingredients was analyzed using network analysis software. A total of 19 potent skin sensitizers were identified from a database that included 99 hair dye products manufactured by Korean domestic companies. Among 19 potent skin sensitizers, the four most frequent were resorcinol, m-aminophenol, p-phenylenediamine (PPD), and p-aminophenol; these four skin-sensitizing ingredients were found in more than 50% of the products studied. Network analysis showed that resorcinol, m-aminophenol, and PPD existed together in many hair dye products. In 99 products examined, the average product contained 4.4 potent sensitizers, and 82% of the products contained four or more skin sensitizers. The present results demonstrate that oxidative hair dye products made by Korean domestic manufacturers contain various numbers and types of potent skin sensitizers. Furthermore, these results suggest that some hair dye products should be used with caution to prevent adverse effects on the skin, including allergic contact dermatitis.

Structural, absorption, and molecular properties of o,o'-dihydroxyazo resorcinol dyes bearing an acryloyloxy group

NASA Astrophysics Data System (ADS)

Özkınalı, Sevil; Çavuş, M. Serdar; Ceylan, Abdullah; Gür, Mahmut

2017-12-01

To the best of our knowledge, this is the first study reporting the synthesis and characterization of o,o‧-dihydroxyazo dyes bearing an acryloyl group. The o,o‧-dihydroxyazo dyes were synthesized through coupling of resorcinol with the diazonium salts of 2-amino-4-methylphenol, 2-aminophenol, 2-amino-4-chlorophenol, and 2-amino-4-nitrophenol. Their acryloyl derivatives were synthesized using metallic sodium and acryloyl chloride under an inert atmosphere. Characterization of the compounds was conducted using infrared (IR), ultraviolet-visible (UV-vis), proton nuclear magnetic resonance (1H NMR), and carbon nuclear magnetic resonance (13C NMR) spectroscopic methods. The tautomerism of the synthesized compounds' was also evaluated. The results were compared with theoretical results obtained by density functional theory (DFT). The DFT calculations were performed to obtain ground-state optimized geometries and calculate the relevant electronic and chemical reactivity parameters. Furthermore, possible tautomers deduced from the UV-vis spectra were investigated using theoretical calculations. Both the IR and NMR spectral data showed that azo tautomers predominate in the solid state and DMSO solvent. The effects of pH, solvent, and substituent on the predominant tautomers were further investigated through UV-vis spectroscopy. The results indicate that hydrazone tautomers were dominant at pH 12 in dimethylformamide (DMF), whereas azo tautomers were dominant at pH 2 in EtOH or CHCl3.

Probing the electronic structure of platinum(II) chromophores: crystal structures, NMR structures, and photophysical properties of six new bis- and di- phenolate/thiolate Pt(II)diimine chromophores.

PubMed

Weinstein, Julia A; Tierney, Mark T; Davies, E Stephen; Base, Karel; Robeiro, Anthony A; Grinstaff, Mark W

2006-05-29

A general route for synthesis of six structurally similar Pt(II) diimine thiolate/phenolates chromophores possessing bulky phenolate or thiolate ligands is reported. The Pt chromophores were characterized using an array of techniques including 1H, 13C, and 195Pt NMR, absorption, emission, (spectro)electrochemistry, and EPR spectroscopy. Systematic variation of the electronic structure of the Pt(II) chromophores studied was achieved by (i) changing solvent polarity; (ii) substituting oxygen for sulfur in the donor ligand; (iii) alternating donor ligands from bis- to di-coordination; and (iv) changing the electron donating/withdrawing properties of the ligand(s). The lowest excited state in these new chromophores was assigned to a [charge-transfer-to-diimine] transition from the HOMO of mixed Pt/S (or Pt/O) character on the basis of absorption and emission spectroscopy, UV/vis (spectro)electrochemistry, and EPR spectroscopy. One of the chromophores, Pt(dpphen)(3,5-di-tert-butyl-catecholate) represents an example of a Pt(II) diimine phenolate chromophore that possesses a reversible oxidation centered predominantly on the donor ligand. Results from EPR spectroscopy indicate participation of the Pt(II) orbitals in the HOMO. There is a dramatic difference in the photophysical properties of carborane complexes compared to other mixed-ligand Pt(II) compounds, which includes room-temperature emission and photostability. The charge-transfer character of the lowest excited state in this series of chromophores is maintained throughout. Moreover, the absorption and emission energies and the redox properties of the excited state can be significantly tuned.

Reactive Diazonium-Modified Silica Fillers for High-Performance Polymers.

PubMed

Sandomierski, Mariusz; Strzemiecka, Beata; Chehimi, Mohamed M; Voelkel, Adam

2016-11-08

We describe a simple way of modification of three silica-based fillers with in situ generated 4-hydroxymethylbenzenediazonium salt ( + N 2 -C 6 H 4 -CH 2 OH). The rationale for using a hydroxyl-functionalized diazonium salt is that it provides surface-functionalized fillers that can react with phenolic resins. The modification of silica by diazonium salts was assessed using Fourier transform infrared (FTIR) spectroscopy and X-ray photoelectron spectroscopy (XPS). FTIR spectroscopy permitted the tracking of benzene ring breathing and C-C. The absence of the characteristic N≡N stretching vibration in the 2200-2300 cm -1 range indicates the loss of the diazonium group. XPS results indicate a higher C/Si atomic ratio after the diazonium modification of fillers and the presence of π-π* C1s satellite peaks characteristic of the surface-tethered aromatic species. Adhesion of aryl layers to the silicas is excellent because they withstand harsh thermal and organic solvent treatments. Phenolic resins (used, for example, as binders in abrasive products) were filled with diazonium-modified silicas at 10-25 wt %. The reactivity of the fillers toward phenolic resins was evaluated by the determination of the flow distance. After annealing at 180 °C, the diazonium-modified silica/phenolic resin composites were mechanically tested using the three-point flexural method. The flexural strength was found to be up to 35% higher than that of the composites prepared without any diazonium salts. Diazonium-modified silica with surface-bound -CH 2 -OH groups is thus ideal reactive filler for phenolic resins. Such filler ensures interfacial chemical reactions with the matrix and imparts robust mechanical properties to the final composites. This specialty diazonium-modified silica will find potential application as fillers in the composites for the abrasive industry. More generally, aryl diazonium salts are a unique new series of compounds for tailoring the surface properties of fillers and tuning the physicochemical and mechanical properties of polymer composites.

Synthesis and in Vitro and in Vivo Evaluation of Phosphoinositide-3-kinase Inhibitors.

PubMed

Burger, Matthew T; Knapp, Mark; Wagman, Allan; Ni, Zhi-Jie; Hendrickson, Thomas; Atallah, Gordana; Zhang, Yanchen; Frazier, Kelly; Verhagen, Joelle; Pfister, Keith; Ng, Simon; Smith, Aaron; Bartulis, Sarah; Merrit, Hanne; Weismann, Marion; Xin, Xiaohua; Haznedar, Joshua; Voliva, Charles F; Iwanowicz, Ed; Pecchi, Sabina

2011-01-13

Phospoinositide-3-kinases (PI3K) are important oncology targets due to the deregulation of this signaling pathway in a wide variety of human cancers. A series of 2-morpholino, 4-substituted, 6-(3-hydroxyphenyl) pyrimidines have been reported as potent inhibitors of PI3Ks. Herein, we describe the structure-guided optimization of these pyrimidines with a focus on replacing the phenol moiety, while maintaining potent target inhibition and improving in vivo properties. A series of 2-morpholino, 4-substituted, 6-heterocyclic pyrimidines, which potently inhibit PI3K, were discovered. Within this series a compound, 17, was identified with suitable pharmacokinetic (PK) properties, which allowed for the establishment of a PI3K PK/pharmacodynamic-efficacy relationship as determined by in vivo inhibition of AKT(Ser473) phosphorylation and tumor growth inhibition in a mouse A2780 tumor xenograft model.

Synthesis and in Vitro and in Vivo Evaluation of Phosphoinositide-3-kinase Inhibitors

PubMed Central

2010-01-01

Phospoinositide-3-kinases (PI3K) are important oncology targets due to the deregulation of this signaling pathway in a wide variety of human cancers. A series of 2-morpholino, 4-substituted, 6-(3-hydroxyphenyl) pyrimidines have been reported as potent inhibitors of PI3Ks. Herein, we describe the structure-guided optimization of these pyrimidines with a focus on replacing the phenol moiety, while maintaining potent target inhibition and improving in vivo properties. A series of 2-morpholino, 4-substituted, 6-heterocyclic pyrimidines, which potently inhibit PI3K, were discovered. Within this series a compound, 17, was identified with suitable pharmacokinetic (PK) properties, which allowed for the establishment of a PI3K PK/pharmacodynamic−efficacy relationship as determined by in vivo inhibition of AKTSer473 phosphorylation and tumor growth inhibition in a mouse A2780 tumor xenograft model. PMID:24900252

Inhibition of the sympathetic nervous system by a series of heterocyclic congeners of dopamine.

PubMed

Sharabi, F M; Long, J P; Cannon, J G; Hatheway, G J

1976-12-01

A series of heterocyclic congeners of dopamine (GJH-series) with different positions of phenolic oxygens and with the possibility of cis and trans isomerism at the 4a-10b ring juncture was evaluated in vitro and in vivo for dopaminergic activity. Two compounds, GJH-166 and GJH-171, were found to suppress the positive chronotropic response induced by stimulation of the right cardioaccelerator nerves. These effects were antagonized by haloperidol. GJH-166, in doses as low as 9.5 x 10(-4) mugmol/kg reduced the resting heart rate in cats anesthetized with alpha-chloralose. GJH-166 and GJH-171 antagonized pressor responses induced by bilateral carotid occlusion and stimulation of the central stump of the sciatic nerve. The results outlined in this manuscript support the hypothesis that the extended conformation of the dihydroxyhenylethylamine moiety of dopamine with a trans isomeric form is favorable for dopaminergic agonist activity.

Method of low pressure and/or evaporative drying of aerogel

DOEpatents

Mayer, Steven T.; Kaschmitter, James L.; Pekala, Richard W.

1995-01-01

A process whereby Resorcinol/Formaldehyde (RF) aerogel having a density of about 0.4-1.2 g/cc can be manufactured using a simple air drying procedure. This process is inherently simpler, quicker, and less expensive than the more conventional supercritical or subcritical CO.sub.2 extraction procedures. RF aerogels can be used as produced, such as in insulation applications, or pyrolyzed to form carbon aerogels with a density of about 0.9 g/cc for use in applications such as batteries, supercapacitors, etc.

Improved colorimetric determination of serum zinc.

PubMed

Johnson, D J; Djuh, Y Y; Bruton, J; Williams, H L

1977-07-01

We show how zinc may easily be quantified in serum by first using an optimum concentration of guanidine hydrochloride to cause release of zinc from proteins, followed by complexation of released metals with cyanide. The cyanide complex of zinc is preferentially demasked with chloral hydrate, followed by a colorimetric reaction between zinc and 4-(2-pyridylazo)resorcinol. This is a sensitive water-soluble ligand; its complex with zinc has an absorption maximum at 497 nm. Values found by this technique compare favorably with those obtained by atomic absorption spectroscopy.

Novel Thioredoxin Inhibitors for Breast Cancer Therapy

DTIC Science & Technology

2001-07-01

of TH-223, the cesium salt of diol 3 16] was alkylated and cyclized under oxidative conditions. All of these compounds have been fully characterized...selectivity for Trx-1 over TrxR. Alkylation at the phenol as shown in the SR-series of analogs mostly abolished activity, with the exception of SR...with either MDA-MB 231 or MCF-7 cells were quite active as antiproliferative agents . Generally, MCF-7 cells were slightly more sensitive than the p53

Electrochemical sensor for catechol and dopamine based on a catalytic molecularly imprinted polymer-conducting polymer hybrid recognition element.

PubMed

Lakshmi, Dhana; Bossi, Alessandra; Whitcombe, Michael J; Chianella, Iva; Fowler, Steven A; Subrahmanyam, Sreenath; Piletska, Elena V; Piletsky, Sergey A

2009-05-01

One of the difficulties with using molecularly imprinted polymers (MIPs) and other electrically insulating materials as the recognition element in electrochemical sensors is the lack of a direct path for the conduction of electrons from the active sites to the electrode. We have sought to address this problem through the preparation and characterization of novel hybrid materials combining a catalytic MIP, capable of oxidizing the template, catechol, with an electrically conducting polymer. In this way a network of "molecular wires" assists in the conduction of electrons from the active sites within the MIP to the electrode surface. This was made possible by the design of a new monomer that combines orthogonal polymerizable functionality; comprising an aniline group and a methacrylamide. Conducting films were prepared on the surface of electrodes (Au on glass) by electropolymerization of the aniline moiety. A layer of MIP was photochemically grafted over the polyaniline, via N,N'-diethyldithiocarbamic acid benzyl ester (iniferter) activation of the methacrylamide groups. Detection of catechol by the hybrid-MIP sensor was found to be specific, and catechol oxidation was detected by cyclic voltammetry at the optimized operating conditions: potential range -0.6 V to +0.8 V (vs Ag/AgCl), scan rate 50 mV/s, PBS pH 7.4. The calibration curve for catechol was found to be linear to 144 microM, with a limit of detection of 228 nM. Catechol and dopamine were detected by the sensor, whereas analogues and potentially interfering compounds, including phenol, resorcinol, hydroquinone, serotonin, and ascorbic acid, had minimal effect (< or = 3%) on the detection of either analyte. Non-imprinted hybrid electrodes and bare gold electrodes failed to give any response to catechol at concentrations below 0.5 mM. Finally, the catalytic properties of the sensor were characterized by chronoamperometry and were found to be consistent with Michaelis-Menten kinetics.

Supplementation with wine phenolic compounds increases the antioxidant capacity of plasma and vitamin E of low-density lipoprotein without changing the lipoprotein Cu(2+)-oxidizability: possible explanation by phenolic location.

PubMed

Carbonneau, M A; Léger, C L; Monnier, L; Bonnet, C; Michel, F; Fouret, G; Dedieu, F; Descomps, B

1997-10-01

To evaluate the effect of the red wine phenolic compound (RWPC) dietary supplementation without alcohol interference on: (1) some of the biochemical characteristics of LDL, (2) the oxidative susceptibility of LDL and (3) the antioxidant capacity of total plasma (Pl-AOC). In order to account for discrepancies between the three series of data, the in vitro stability of the association of phenolic compounds and LDL was tested. An intervention study with 20 volunteers. Each served as his own control. Cu(2+)-oxidizability of LDL and Pl-AOC were tested on blood samples before and after dietary supplementation. Cu(2+)-oxidizability of LDL was also tested by co-incubation in the presence of RWPC or phenolic acids with or without extensive dialysis. The Laboratory of Lipid Biochemistry and Biology, School of Medicine, and the Laboratory of Metabolic Diseases, Lapeyronie Hospital, University of Montpellier, France. Healthy males, nonsmokers and moderate drinkers, submitted to a dietary regimen deprived of vitamin E and C for a period of 10 d before supplementation. They also abstained from alcohol, wine, fruit juices, coffee, tea and cola beverages during this period. Six 0.33 g capsules/d (namely two capsules at each meal) of a preparation of red wine phenolic compounds in a dry powder form were given to the volunteers over a period of two weeks. Blood samples were drawn in fasting conditions at day 0 and day 14 of the supplementation period. Supplementation led to: (1) in LDL, a significant increase in vitamin E content (n = 20, P = 0.01) or vitamin E/total fatty acid bis-allylic carbon number ratio (n = 20, P = 0.006) without modification in the other biochemical characteristics or Cu(2+)-oxidizability; (2) in plasma, a significant increase in the antioxidant capacity (n = 11, P = 0.01). In vitro studies showed that RWPC or sinapic, caffeic or ferulic acids incubated in the presence of LDL increased the protection of the lipoparticle against oxidation (caffeic > sinapic > ferulic). This effect, however, was totally lost after extensive dialysis. The enhancing effect of the RWPC supplementation on Pl-AOC may be due to a phenolic-compound action both in the aqueous phase of plasma and at the surface of lipoprotein particles. Surface location possibly explains the enhancing-sparing effect of supplementation on LDL vitamin E and the absence of effect on dialysed-LDL oxidizability.

Antioxidant capacities and total phenolic contents of 20 polyherbal remedies used as tonics by folk healers in Phatthalung and Songkhla provinces, Thailand.

PubMed

Chanthasri, Wipawee; Puangkeaw, Nuntitporn; Kunworarath, Nongluk; Jaisamut, Patcharawalai; Limsuwan, Surasak; Maneenoon, Katesarin; Choochana, Piyapong; Chusri, Sasitorn

2018-02-21

Uses of polyherbal formulations have played a major role in traditional medicine. The present study is focused on the formulations used in traditional Thai folkloric medicine as tonics or bracers. Twenty documented polyherbal mixtures, used as nourishing tonics by the folk healers in Phatthalung and Songkhla provinces in southern Thailand, are targeted. Despite traditional health claims, there is no scientific evidence to support the utilization of polyherbal formulations. The phenolic and flavonoid contents of the polyherbal formulations and a series of antioxidant tests were applied to measure their capability as preventive or chain-breaking antioxidants. In addition, the cytotoxic activity of effective formulations was assayed in Vero cells. Ninety-eight plant species belonging to 45 families were used to prepare the tested formulation. The preliminary results revealed that water extracts of THP-R016 and THP-R019 contain a high level of total phenolic and flavonoid contents and exhibit remarkable antioxidant activities, as tested by DPPH, ABTS, and FRAP assays. The extract of THP-R019 also showed the strongest metal chelating activities, whereas THP-R016 extract possessed notable superoxide anion and peroxyl radical scavenging abilities. The data provide evidence that the water extracts of folkloric polyherbal formulations, particularly THP-R016, are a potential source of natural antioxidants, which will be valuable in the pharmaceutical and nutraceutical industries. The free radical scavenging of THP-R016 may be due to the contribution of phenolic and flavonoid contents. Useful characteristics for the consumer, such as the phytochemical profiles of active ingredients, cellular based antioxidant properties and beneficial effects in vivo, are under further investigation.

Fire Safety Tests for Spherical Resorcinol Formaldehyde Resin: Data Summary Report

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

Kim, Dong-Sang; Peterson, Reid A.; Schweiger, Michael J.

2012-07-30

A draft safety evaluation of the scenario for spherical resorcinol-formaldehyde (SRF) resin fire inside the ion exchange column was performed by the Hanford Tank Waste Treatment and Immobilization Plant (WTP) Fire Safety organization. The result of this draft evaluation suggested a potential change of the fire safety classification for the Cesium Ion Exchange Process System (CXP) emergency elution vessels, equipment, and piping, which may be overly bounding based on the fire performance data from the manufacturer of the ion exchange resin selected for use at the WTP. To resolve this question, the fire properties of the SRF resin were measuredmore » by Southwest Research Institute (SwRI), following the American Society for Testing and Materials (ASTM) standard procedures, through a subcontract managed by Pacific Northwest National Laboratory (PNNL). For some tests, the ASTM standard procedures were not entirely appropriate or practical for the SRF resin material, so the procedures were modified and deviations from the ASTM standard procedures were noted. This report summarizes the results of fire safety tests performed and reported by SwRI. The efforts by PNNL were limited to summarizing the test results provided by SwRI into one consolidated data report. All as-received SwRI reports are attached to this report in the Appendix. Where applicable, the precision and bias of each test method, as given by each ASTM standard procedure, are included and compared with the SwRI test results of the SRF resin.« less

Inhibition of development, swarming differentiation and virulence factors in Proteus mirabilis by an extract of Lithrea molleoides and its active principle (Z,Z)-5-(trideca-4',7'-dienyl)-resorcinol.

PubMed

Carpinella, M C; De Bellis, L; Joray, M B; Sosa, V; Zunino, P M; Palacios, S M

2011-08-15

Antibacterial activity of Lithrea molleoides extract against Proteus mirabilis has been previously reported by our group. In the present study, the compound (Z,Z)-5-(trideca-4',7'-dienyl)-resorcinol (1) was isolated as its responsible active principle. The effects of the compound obtained and of L. molleoides extract on P. mirabilis growth and virulence factors were evaluated. Compound 1 showed MIC and MBC values of 4000 μg/ml. It was found that the extract, at four times the MIC, produced complete killing of the uropathogen at 2h from the beginning of the experiment, while the alkylresorcinol, at four times the MIC, produced the same effect after 24 h. Hemolysis was adversely affected in treatments with both products at 8 μg/ml, while hemagglutination was not altered. The whole extract induced complete autoaggregation of P. mirabilis at 2000 μg/ml, while compound 1 at the same concentration did not show this property. Swarming motility was delayed in treatments with the extract and with 1 at 1000 and 8 μg/ml, respectively, at 8h from the beginning of the assay. Complete inhibition of the phenomenon was still observed after 24 h when compound 1 was added at 125 μg/ml. These findings offer the possibility of new classes of antimicrobial medicines to tackle infections caused by P. mirabilis. Copyright © 2011 Elsevier GmbH. All rights reserved.

Solid phase extraction of rare earth elements in seawater and estuarine water with 4-(2-thiazolylazo) resorcinol immobilized Chromosorb 106 for determination by inductively coupled plasma mass spectrometry

PubMed Central

Zereen, Fahmida; Yilmaz, Vedat; Arslan, Zikri

2013-01-01

A solid phase preconcentration method has been developed using new chelating resin prepared by immobilization of 4-(2-thiazolylazo) resorcinol (TAR) on Chromosorb 106. The method was optimized for determination of rare earth elements (REEs) in seawater and estuarine water samples by inductively coupled plasma mass spectrometry (ICP-MS). The effects of various experimental parameters, such as load pH, eluent concentration, sample and eluent flow rates were examined to find the optimum operating conditions. The REEs were quantitatively retained from saline solutions on a minicolumn Chromosorb 106-TAR resin at pH 5.0 and then eluted with 1.0 mL of 1% (v/v) HNO3. The resin possesses large sorption capacity for REEs ranging from 81.1 µmol g−1 for Lu and 108 µmol g−1 for Nd. Detection limits (3s) varied between 0.06 ng L−1 for Pr to 0.31 for Ce for preconcentration of 5.0 mL blank solutions (pH 5.0). The relative standard deviation for triplicate measurements was less than 5% at 0.1 µg L−1 level. The method was validated by analysis Nearshore seawater certified reference material (CASS–4). The elemental results were comparable with the values reported in literature. The method was verified by analysis of spiked and unspiked coastal seawater and estuarine water samples. PMID:24000264

Cannabidiol-2',6'-dimethyl ether, a cannabidiol derivative, is a highly potent and selective 15-lipoxygenase inhibitor.

PubMed

Takeda, Shuso; Usami, Noriyuki; Yamamoto, Ikuo; Watanabe, Kazuhito

2009-08-01

The inhibitory effect of nordihydroguaiaretic acid (NDGA) (a nonselective lipoxygenase (LOX) inhibitor)-mediated 15-LOX inhibition has been reported to be affected by modification of its catechol ring, such as methylation of the hydroxyl group. Cannabidiol (CBD), one of the major components of marijuana, is known to inhibit LOX activity. Based on the phenomenon observed in NDGA, we investigated whether or not methylation of CBD affects its inhibitory potential against 15-LOX, because CBD contains a resorcinol ring, which is an isomer of catechol. Although CBD inhibited 15-LOX activity with an IC(50) value (50% inhibition concentration) of 2.56 microM, its monomethylated and dimethylated derivatives, CBD-2'-monomethyl ether and CBD-2',6'-dimethyl ether (CBDD), inhibited 15-LOX activity more strongly than CBD. The number of methyl groups in the resorcinol moiety of CBD (as a prototype) appears to be a key determinant for potency and selectivity in inhibition of 15-LOX. The IC(50) value of 15-LOX inhibition by CBDD is 0.28 microM, and the inhibition selectivity for 15-LOX (i.e., the 5-LOX/15-LOX ratio of IC(50) values) is more than 700. Among LOX isoforms, 15-LOX is known to be able to oxygenate cholesterol esters in the low-density lipoprotein (LDL) particle (i.e., the formation of oxidized LDL). Thus, 15-LOX is suggested to be involved in development of atherosclerosis, and CBDD may be a useful prototype for producing medicines for atherosclerosis.

Solid phase extraction of rare earth elements in seawater and estuarine water with 4-(2-thiazolylazo) resorcinol immobilized Chromosorb 106 for determination by inductively coupled plasma mass spectrometry.

PubMed

Zereen, Fahmida; Yilmaz, Vedat; Arslan, Zikri

2013-09-01

A solid phase preconcentration method has been developed using new chelating resin prepared by immobilization of 4-(2-thiazolylazo) resorcinol (TAR) on Chromosorb 106. The method was optimized for determination of rare earth elements (REEs) in seawater and estuarine water samples by inductively coupled plasma mass spectrometry (ICP-MS). The effects of various experimental parameters, such as load pH, eluent concentration, sample and eluent flow rates were examined to find the optimum operating conditions. The REEs were quantitatively retained from saline solutions on a minicolumn Chromosorb 106-TAR resin at pH 5.0 and then eluted with 1.0 mL of 1% (v/v) HNO 3 . The resin possesses large sorption capacity for REEs ranging from 81.1 µmol g -1 for Lu and 108 µmol g -1 for Nd. Detection limits (3s) varied between 0.06 ng L -1 for Pr to 0.31 for Ce for preconcentration of 5.0 mL blank solutions (pH 5.0). The relative standard deviation for triplicate measurements was less than 5% at 0.1 µg L -1 level. The method was validated by analysis Nearshore seawater certified reference material (CASS-4). The elemental results were comparable with the values reported in literature. The method was verified by analysis of spiked and unspiked coastal seawater and estuarine water samples.

In situ and laboratory studies on the fate of specific organic compounds in an anaerobic landfill leachate plume, 1. Experimental conditions and fate of phenolic compounds

NASA Astrophysics Data System (ADS)

Nielsen, Per H.; Albrechtsen, Hans-Jørgen; Heron, Gorm; Christensen, Thomas H.

1995-11-01

The transformation of specific organic compounds was investigated by in situ and laboratory experiments in an anaerobic landfill leachate pollution plume at four different distances from the landfill. This paper presents the experimental conditions in the in situ microcosm and laboratory batch microcosm experiments performed and the results on the fate of 7 phenolic compounds. Part 2 of this series of papers, also published in this issue, presents the results on the fate of 8 aromatic compounds and 4 chlorinated aliphatic compounds. The redox conditions in the plume were characterized as methanogenic, Fe(III)-reducing and NO 3--reducing by the redox sensitive species present in groundwater and sediment and by bioassays. With a few exceptions the aquifer redox conditions were maintained throughout the experiments as monitored by redox sensitive species present in groundwater during the experiments, by redox sensitive species present in the sediment after the experiments and by bioassays performed after the experiments. Transformation of nitrophenol was very fast close to the landfill in strongly reducing conditions, while transformation was slower in the more oxidized part of the plume. Lag phases for the nitrophenols were short (maximum 10 days). Phenol was only transformed in the more distant part of the plume in experiments where NO 3-, Fe(III) and Mn(IV) reduction was dominant. Lag phases for phenol were either absent or lasted up to 2 months. Dichlorophenols were only transformed in experiments representing strongly reducing, presumably methanogenic, redox conditions close to the landfill after lag phases of up to 3 months. Transformation of o-cresol was not observed in any of the experiments throughout the plume. Generally, there was good accordance between the results obtained by in situ and laboratory experiments, both concerning redox conditions and the fate of the phenolic compounds. However, for phenol and 2,4-dichlorophenol, transformation was observed in some in situ experiments but not in the corresponding laboratory experiments. In some experiments, this coul be explained by differences in the redox conditions developing during the experiments. Nitrophenols were apparently transformed abiotically in the most reduced part of the plume, at 2 m from the landfill.

Polyoxometalate oxidation of non-phenolic lignin subunits in water : effect of substrate structure on reaction kinetics

Treesearch

Tomoya Yokoyama; Hou-min Chang; Richard S. Reiner; Raja H. Atalla; Ira A. Weinstock; John F. Kadla

2004-01-01

The effect of lignin-biopolymer structure on the mechanism of its oxidative depolymerization by polyoxometalates (POMs) was investigated by reacting an equilibrated POM ensemble with a series of ring-substituted benzyl alcohols. Under anaerobic conditions in mixed water/methanol, observed pseudo-first order reaction rates (150°C) of 8.96 x 10–3 and 4.89 x 10–3 sec–1...

New aromatic activated dihalides and bisphenol monomers for the preparation of novel poly(arylene ethers)

NASA Technical Reports Server (NTRS)

Wolfe, James F.

1993-01-01

The goal of this research program was to synthesize a series of unique monomers of type I to be utilized at NASA-Langley in the preparation of new poly(arylene ether ketones), poly(arylene ether ketosulfones), and poly(arylene ether ketophosphine oxides). These A-A and A-B monomer systems, which possess activated aryl halide and/or phenolic end groups, are accessible via condensation reactions of appropriately substituted aryl acetonitrile carbanions with activated aryl dihalides followed by oxidative decyanation.

Determination of polar organic solutes in oil-shale retort water

USGS Publications Warehouse

Leenheer, J.A.; Noyes, T.I.; Stuber, H.A.

1982-01-01

A variety of analytical methods were used to quantitatively determine polar organic solutes in process retort water and a gas-condensate retort water produced in a modified in situ oil-shale retort. Specific compounds accounting for 50% of the dissolved organic carbon were identified in both retort waters. In the process water, 42% of the dissolved organic carbon consisted of a homologous series of fatty acids from C2 to C10. Dissolved organic carbon percentages for other identified compound classes were as follows: aliphatic dicarboxylic acids, 1.4%; phenols, 2.2%; hydroxypyridines, 1.1%; aliphatic amides, 1.2%. In the gas-condensate retort water, aromatic amines were most abundant at 19.3% of the dissolved organic carbon, followed by phenols (17.8%), nitriles (4.3%), aliphatic alcohols (3.5%), aliphatic ketones (2.4%), and lactones (1.3%). Steam-volatile organic solutes were enriched in the gas-condensate retort water, whereas nonvolatile acids and polyfunctional neutral compounds were predominant organic constituents of the process retort water.

Deep eutectic solvent-based valorization of spent coffee grounds.

PubMed

Yoo, Da Eun; Jeong, Kyung Min; Han, Se Young; Kim, Eun Mi; Jin, Yan; Lee, Jeongmi

2018-07-30

Spent coffee grounds (SCGs) are viewed as a valuable resource for useful bioactive compounds, such as chlorogenic acids and flavonoids, and we suggest an eco-friendly and efficient valorization method. A series of choline chloride-based deep eutectic solvents (DESs) were tested as green extraction solvents for use with ultrasound-assisted extraction. Extraction efficiency was evaluated based on total phenolic content (TPC), total flavonoid content, total chlorogenic acids, and/or anti-oxidant activity. A binary DES named HC-6, which was composed of 1,6-hexanediol:choline chloride (molar ratio 7:1) was designed to produce the highest efficiency. Experimental conditions were screened and optimized for maximized efficiency using a two-level fractional factorial design and a central composite design, respectively. As a result, the proposed method presented significantly enhanced TPC and anti-oxidant activity. In addition, phenolic compounds could be easily recovered from extracts at high recovery yields (>90%) by adsorption chromatography. Copyright © 2018 Elsevier Ltd. All rights reserved.

Antioxidant Activity, Acetylcholinesterase, and Carbonic Anhydrase Inhibitory Properties of Novel Ureas Derived from Phenethylamines.

PubMed

Aksu, Kadir; Özgeriş, Bünyamin; Taslimi, Parham; Naderi, Ali; Gülçin, İlhami; Göksu, Süleyman

2016-12-01

A series of ureas derived from phenethylamines were synthesized and evaluated for human carbonic anhydrase (hCA) I and II, acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) enzyme inhibitory activities and antioxidant properties. The ureas were synthesized from the reactions of substituted phenethylamines with N,N-dimethylcarbamoyl chloride; then, the synthesized compounds were converted to their corresponding phenolic derivatives via O-demethylation. hCA I and II were effectively inhibited by the newly synthesized compounds, with K i values in the range of 0.307-0.432 nM for hCA I and 0.149-0.278 nM for hCA II. On the other hand, the K i parameters of these compounds for AChE and BChE were determined in the range of 0.129-0.434 and 0.095-0.207 nM, respectively. Phenolic ureas also showed good antioxidant activities. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Ionic liquid [OMIm][OAc] directly inducing oxidation cleavage of the β-O-4 bond of lignin model compounds.

PubMed

Yang, Yingying; Fan, Honglei; Meng, Qinglei; Zhang, Zhaofu; Yang, Guanying; Han, Buxing

2017-08-03

We explored the oxidation reactions of lignin model compounds directly induced by ionic liquids under metal-free conditions. In this work, it was found that ionic liquid 1-octyl-3-methylimidazolium acetate as a solvent could promote the aerobic oxidation of lignin model compound 2-phenoxyacetophenone (1) and the yields of phenol and benzoic acid from 1 could be as high as 96% and 86%, respectively. A possible reaction pathway was proposed based on a series of control experiments. An acetate anion from the ionic liquid attacked the hydrogen from the β-carbon thereby inducing the cleavage of the C-O bond of the aromatic ether. Furthermore, it was found that 2-(2-methoxyphenoxy)-1-phenylethanone (4) with a methoxyl group could also be transformed into aromatic products in this simple reaction system and the yields of phenol and benzoic acid from 4 could be as high as 98% and 85%, respectively. This work provides a simple way for efficient transformation of lignin model compounds.

Thiophene-Core Estrogen Receptor Ligands Having Superagonist Activity

PubMed Central

Min, Jian; Wang, Pengcheng; Srinivasan, Sathish; Nwachukwu, Jerome C.; Guo, Pu; Huang, Minjian; Carlson, Kathryn E.; Katzenellenbogen, John A.; Nettles, Kendall W.; Zhou, Hai-Bing

2013-01-01

To probe the importance of the heterocyclic core of estrogen receptor (ER) ligands, we prepared a series of thiophene-core ligands by Suzuki cross-coupling of aryl boronic acids with bromo-thiophenes, and we assessed their receptor binding and cell biological activities. The disposition of the phenol substituents on the thiophene core, at alternate or adjacent sites, and the nature of substituents on these phenols all contribute to binding affinity and subtype selectivity. Most of the bis(hydroxyphenyl)-thiophenes were ERβ selective, whereas the tris(hydroxyphenyl)-thiophenes were ERα selective; analogous furan-core compounds generally have lower affinity and less selectivity. Some diarylthiophenes show distinct superagonist activity in reporter gene assays, giving maximal activities 2–3 times that of estradiol, and modeling suggests that these ligands have a different interaction with a hydrogen-bonding residue in helix-11. Ligand-core modification may be a new strategy for developing ER ligands whose selectivity is based on having transcriptional activity greater than that of estradiol. PMID:23586645

Synthesis and in Vitro Antifungal Activity against Botrytis cinerea of Geranylated Phenols and Their Phenyl Acetate Derivatives

PubMed Central

Chávez, María I.; Soto, Mauricio; Taborga, Lautaro; Díaz, Katy; Olea, Andrés F.; Bay, Camila; Peña-Cortés, Hugo; Espinoza, Luis

2015-01-01

The inhibitory effects on the mycelial growth of plant pathogen Botritys cinerea have been evaluated for a series of geranylphenols substituted with one, two and three methoxy groups in the aromatic ring. The results show that the antifungal activity depends on the structure of the geranylphenols, increasing from 40% to 90% by increasing the number of methoxy groups. On the other hand, the acetylation of the –OH group induces a change of activity that depends on the number of methoxy groups. The biological activity of digeranyl derivatives is lower than that exhibited by the respective monogeranyl compound. All tested geranylphenols have been synthesized by direct coupling of geraniol and the respective phenol. The effect of solvent on yields and product distribution is discussed. For monomethoxyphenols the reaction gives better yields when acetonitrile is used as a solvent and AgNO3 is used as a secondary catalyst. However, for di- and trimethoxyphenols the reaction proceeds only in dioxane. PMID:26287171

On the correlation between the porous structure and the electrochemical response of powdered and monolithic carbon aerogels as electrodes for capacitive deionization

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

Macías, C., E-mail: carlosmacias@nanoquimia.com; Lavela, P.; Rasines, G.

2016-10-15

The combined effect of resorcinol/catalyst (100≤R/C≤800) and resorcinol/water (0.04≤R/W≤0.13) molar ratio on the textural and capacitive properties of carbon aerogels with potential application for capacitive deionization has been evaluated. Activated and pyrolyzed aerogels were synthesized by the sol-gel polymerization of resorcinol-formaldehyde mixtures and dried in supercritical conditions. Data show that high R/C and R/W molar ratios lead to materials with large pores in the mesopore range, whereas the surface area and micropore volumes remain somewhat the same. The activation of the aerogels increased the differences in the specific surface and micropore volumes due to the development of microporosity. This effectmore » was more remarkable for the samples with low R/C whatever the R/W ratio, indicating that the carbon aerogel obtained using high amounts of catalyst are more prone to be activated. Regarding the electrochemical features of the aerogels, low capacitance values were measured in aerogels combining low R/W and high R/C and reciprocally low R/C and high R/W molar ratios, due to their higher resistance. Polarization resistances were found to be slightly higher for the pyrolyzed than for activated aerogels, and followed a decreasing trend with the mesoporosity, indicating the outstanding contribution of the mesoporous network to provide a good kinetic response. The desalting capacity of monolithic aerogels showed a simultaneous dependence with the surface area and the resistivity of the electrodes, pointing out the importance of performing electrochemical measurements in adequate cell configurations (i.e., desalting units) upon the intended application. - Graphical abstract: The textural properties of carbon aerogels are strongly influenced by the synthesis parameters precursor to catalyst (R/C) and water (R/C) ratios. The volumetric capacitance measured in a symmetric cell with monolithic electrodes of carbon aerogel strongly correlates with both surface area and electrical resistivity. - Highlights: • Influence of the synthesis conditions on the properties of carbon aerogels is reported. • Specific surface decreases in the activated samples when either R/C or R/W increase. • An enhanced decrease of the capacitance was observed when R/C and R/W increase. • Ohmic resistance of the electrodes that strongly depends on the R/W and R/C. • Electrosorption capacity is successfully correlated to surface area and resistivity.« less

Ferrocene Functionalized Endocrine Modulators as Anticancer Agents

NASA Astrophysics Data System (ADS)

Hillard, Elizabeth A.; Vessières, Anne; Jaouen, Gerard

We present here some of our studies on the synthesis and behaviour of ferrocenyl selective endocrine receptor modulators against cancer cells, particularly breast and prostate cancers. The proliferative/anti-proliferative effects of compounds based on steroidal and non-steroidal endocrine modulators have been extensively explored in vitro. Structure-activity relationship studies of such molecules, particularly the hydroxyferrocifens and ferrocene phenols, have shown the effect of (1) the presence and the length of the N,N-dimethylamino side chain, (2) the presence and position of the phenol group, (3) the role of the ferrocenyl moiety, (4) that of conjugation, (5) phenyl functionalisation and (6) the placement of the phenyl group. Compounds possessing a ferrocene moiety linked to a p-phenol by a conjugated π-system are among the most potent of the series, with IC50 values ranging from 0.090 to 0.6µM on hormone independent breast cancer cells. Based on the SAR data and electrochemical studies, we have proposed an original mechanism to explain the unusual behaviour of these bioorganometallic species and coin the term "kronatropic" to qualify this effect, involving ROS production and bio-oxidation. In addition, the importance of formulation is underlined. We also discuss the behaviour of ferrocenyl androgens and anti-androgens for possible use against prostate cancers. In sum, ferrocene has proven to be a fascinating substituent due to its vast potential for oncology.

Versatile Surface Functionalization of Metal-Organic Frameworks through Direct Metal Coordination with a Phenolic Lipid Enables Diverse Applications

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

Zhu, Wei; Xiang, Guolei; Shang, Jin

Here, a novel strategy for the versatile functionalization of the external surface of metal-organic frameworks (MOFs) has been developed based on the direct coordination of a phenolic-inspired lipid molecule DPGG (1,2-dipalmitoyl-sn-glycero-3-galloyl) with metal nodes/sites surrounding MOF surface. X-ray diffraction and Argon sorption analysis prove that the modified MOF particles retain their structural integrity and porosity after surface modification. Density functional theory calculations reveal that strong chelation strength between the metal sites and the galloyl head group of DPGG is the basic prerequisite for successful coating. Due to the pH-responsive nature of metal-phenol complexation, the modification process is reversible by simplemore » washing in weak acidic water, showing an excellent regeneration ability for water-stable MOFs. Moreover, the colloidal stability of the modified MOFs in the nonpolar solvent allows them to be further organized into 2 dimensional MOF or MOF/polymer monolayers by evaporation-induced interfacial assembly conducted on an air/water interface. Lastly, the easy fusion of a second functional layer onto DPGG-modified MOF cores, enabled a series of MOF-based functional nanoarchitectures, such as MOFs encapsulated within hybrid supported lipid bilayers (so-called protocells), polyhedral core-shell structures, hybrid lipid-modified-plasmonic vesicles and multicomponent supraparticles with target functionalities, to be generated. for a wide range of applications.« less

In vitro antioxidant and in vivo photoprotective effect of pistachio (Pistacia vera L., variety Bronte) seed and skin extracts.

PubMed

Martorana, Maria; Arcoraci, Teresita; Rizza, Luisa; Cristani, Mariateresa; Bonina, Francesco Paolo; Saija, Antonina; Trombetta, Domenico; Tomaino, Antonio

2013-03-01

Pistachio (Pistacia vera L.) nuts are a rich source of phenolic compounds, known for their high antioxidant activity, and contained not only in the seeds but also in the skin. A pistachio cultivar of high quality is typical of Bronte, Sicily, Italy. The purpose of our study was to investigate the chemical composition and antioxidant properties of two polyphenol-rich extracts from skins (TP) and decorticated seeds (SP) of Bronte pistachios, and to verify the potential use of these extracts for topical photoprotective products. Chemical analysis showed that the TP and SP extracts contain high levels of phenolic compounds, but the TP extract is about ten times richer in phenols than the SP extract, being anthocyanins the most abundant compounds found in the TP extract. Both these extracts, and especially the TP extract, possess good radical scavenger/antioxidant properties, as shown in a series of in vitro assays carried out using homogenous and non-homogenous chemical environment. Furthermore both the TP extract and, although at a lower degree, the SP extract reduce, when topically applied, UV-B-induced skin erythema in human volunteers. These findings suggest that extracts from Bronte TP and SP could be successfully employed as photoprotective ingredients in topical cosmetic and pharmaceutical formulations. Copyright © 2013 Elsevier B.V. All rights reserved.

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

Zhang, W.; Chang, Q.G.; Liu, W.D.

A series of follow-up investigations were performed to produce data for improving the four-indicator carbon selection method that we developed to identify high-potential activated carbons effective for removing specific organic water pollutants. The carbon's pore structure and surface chemistry are dependent on the raw material and the activation process. Coconut carbons have relatively more small pores than large pores; coal and apricot nutshell/walnut shell fruit carbons have the desirable pore structures for removing adsorbates of all sizes. Chemical activation, excessive activation, and/or thermal reactivation enlarge small pores, resulting in reduced phenol number and higher tannic acid number. Activated carbon's phenol,more » iodine, methylene blue, and tannic acid numbers are convenient indicators of its surface area and pore volume of pore diameters < 10, 10-15, 15-28, and > 28 angstrom, respectively. The phenol number of a carbon is also a good indicator of its surface acidity of oxygen-containing organic functional groups that affect the adsorptive capacity for aromatic and other small polar organics. The tannic acid number is an indicator of carbon's capacity for large, high-molecular-weight natural organic precursors of disinfection by-products in water treatment. The experimental results for removing nitrobenzene, methyl-tert-butyl ether, 4,4-bisphenol, humic acid, and the organic constituents of a biologically treated coking-plant effluent have demonstrated the effectiveness of this capacity-indicator-based method of carbon selection.« less

Pervaporation of phenols

DOEpatents

Boddeker, Karl W.

1989-01-01

Aqueous phenolic solutions are separated by pervaporation to yield a phenol-depleted retentate and a phenol-enriched permeate. The separation effect is enhanced by phase segregation into two immiscible phases, "phenol in water" (approximately 10% phenol), and "water in phenol" (approximately 70% phenol). Membranes capable of enriching phenols by pervaporation include elastomeric polymers and anion exchange membranes, membrane selection and process design being guided by pervaporation performance and chemical stability towards phenolic solutions. Single- and multiple-stage procresses are disclosed, both for the enrichment of phenols and for purification of water from phenolic contamination.

Pervaporation of phenols

DOEpatents

Boddeker, K.W.

1989-02-21

Aqueous phenolic solutions are separated by pervaporation to yield a phenol-depleted retentate and a phenol-enriched permeate. The separation effect is enhanced by phase segregation into two immiscible phases, phenol in water'' (approximately 10% phenol), and water in phenol'' (approximately 70% phenol). Membranes capable of enriching phenols by pervaporation include elastomeric polymers and anion exchange membranes, membrane selection and process design being guided by pervaporation performance and chemical stability towards phenolic solutions. Single- and multiple-stage processes are disclosed, both for the enrichment of phenols and for purification of water from phenolic contamination. 8 figs.

Coupling the Alkaline-Surfactant-Polymer Technology and The Gelation Technology to Maximize Oil Production

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

Malcolm Pitts; Jie Qi; Dan Wilson

2005-12-01

Gelation technologies have been developed to provide more efficient vertical sweep efficiencies for flooding naturally fractured oil reservoirs or reservoirs with different sand lenses with high permeability contrast. The field proven alkaline-surfactant-polymer technology economically recovers 15% to 25% OOIP more crude oil than waterflooding from swept pore space of an oil reservoir. However, alkaline-surfactant-polymer technology is not amenable to naturally fractured reservoirs or reservoirs with high permeability contrast zones because much of injected solution bypasses target pore space containing oil. This work investigates whether combining these two technologies could broaden applicability of alkaline-surfactant-polymer flooding into these reservoirs. Fluid-fluid interaction withmore » different gel chemical compositions and alkaline-surfactant-polymer solution with pH values ranging from 9.2 to 12.9 have been tested. Aluminum-polyacrylamide gels are not stable to alkaline-surfactant-polymer solutions at any pH. Chromium-polyacrylamide gels with polymer to chromium ion ratios of 25 or greater were stable to alkaline-surfactant-polymer solutions if solution pH was 10.6 or less. When the polymer to chromium ion was 15 or less, chromium-polyacrylamide gels were stable to alkaline-surfactant-polymer solutions with pH values up to 12.9. Chromium-xanthan gum gels were stable to alkaline-surfactant-polymer solutions with pH values of 12.9 at the polymer to chromium ion ratios tested. Silicate-polyacrylamide, resorcinol-formaldehyde, and sulfomethylated resorcinol-formaldehyde gels were also stable to alkaline-surfactant-polymer solutions with pH values ranging from 9.2 to 12.9. Iron-polyacrylamide gels were immediately destroyed when contacted with any of the alkaline-surfactant-polymer solutions with pH values ranging from 9.2 to 12.9. Gel solutions under dynamic conditions of linear corefloods showed similar stability to alkaline-surfactant-polymer solutions as in the fluid-fluid analyses with the exception of the xanthan gum-chromium acetate gels. Aluminum-polyacrylamide flowing gels are not stable to alkaline-surfactant-polymer solutions of either pH 10.5 or 12.9, either in linear corefloods or in dual separate radial core, common manifold corefloods. Chromium acetate-polyacrylamide flowing and rigid tonguing gels are stable to subsequent alkaline-surfactant-polymer solution injection. Rigid tonguing chromium acetate-polyacrylamide gels maintained permeability reduction better than flowing chromium acetate-polyacrylamide gels. Chromium acetate gels were stable to injection of alkaline-surfactant-polymer solutions at 72 F, 125 F and 175 F in linear corefloods. Chromium acetate-polyacrylamide gels maintained diversion capability after injection of an alkaline-surfactant-polymer solution in stacked; radial coreflood with a common well bore. Chromium acetate-polyacrylamide gel used to seal fractured core maintain fracture closure if followed by an alkaline-surfactant-polymer solution. Chromium acetatexanthan gum rigid gels are not stable to subsequent alkaline-surfactant-polymer solution injection at 72, 125, and 175 F. Silicate-polyacrylamide gels are not stable with subsequent injection of either a pH 10.5 or a 12.9 alkaline-surfactant-polymer solution. Resorcinol-formaldehyde gels were stable to subsequent alkaline-surfactant-polymer solution injection. When evaluated in a dual core configuration, injected fluid flows into the core with the greatest effective permeability to the injected fluid. The same gel stability trends to subsequent alkaline-surfactant-polymer injected solution were observed. Aluminum citrate-polyacrylamide, resorcinol-formaldehyde, and the silicate-polyacrylamide gel systems did not produce significant incremental oil in linear corefloods. Both flowing and rigid tonguing chromium acetate-polyacrylamide gels and the xanthan gum-chromium acetate gel system produced incremental oil with the rigid tonguing gel producing the greatest amount. Higher oil recovery could have been due to higher differential pressures across cores. Aluminum citrate-polyacrylamide gels, chromium acetate-polyacrylamide gels, silicate-polymer, and chromium-xanthan gum gels did not alter an alkaline-surfactant-polymer solution's ability to produce incremental oil. Incremental oil was reduced with the resorcinol-formaldehyde gel system. Total waterflood plus chemical flood oil recovery sequence recoveries were generally similar. Performance and produced polymer evaluation of four alkaline-surfactant-polymer projects concluded that only one of the projects could have benefited from combining the alkaline-surfactant-polymer and gelation technologies. Cambridge, the 1993 Daqing, Mellott Ranch, and the Wardlaw alkaline-surfacant-polymer floods were studied. An initial gel treatment followed by an alkaline-surfactant-polymer flood in the Wardlaw field would have been a benefit due to reduction of fracture flow.« less

Nitrogen-doped carbon aerogels for electrical energy storage

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

Campbell, Patrick; Montalvo, Elizabeth; Baumann, Theodore F.

Disclosed here is a method for making a nitrogen-doped carbon aerogel, comprising: preparing a reaction mixture comprising formaldehyde, at least one nitrogen-containing resorcinol analog, at least one catalyst, and at least one solvent; curing the reaction mixture to produce a wet gel; drying the wet gel to produce a dry gel; and thermally annealing the dry gel to produce the nitrogen-doped carbon aerogel. Also disclosed is a nitrogen-doped carbon aerogel obtained according to the method and a supercapacitor comprising the nitrogen-doped carbon aerogel.

Three-dimensional multichannel aerogel of carbon quantum dots for high-performance supercapacitors.

PubMed

Lv, Lingxiao; Fan, Yueqiong; Chen, Qing; Zhao, Yang; Hu, Yue; Zhang, Zhipan; Chen, Nan; Qu, Liangti

2014-06-13

A three-dimensional (3D) carbon quantum dot (CQD) aerogel has been prepared by in situ assembling CQDs in the sol-gel polymerization of resorcinol (R) and formaldehyde (F) and subsequently pyrolyzing the formed CQD gel. Compared to the supercapacitor based on the CQD-free aerogel, the supercapacitor fabricated with the CQD aerogel showed 20-fold higher specific capacitance (294.7 F g(-1) at the current density of 0.5 A g(-1)) and an excellent stability over 1000 consecutive charge-discharge cycles.

Three-dimensional multichannel aerogel of carbon quantum dots for high-performance supercapacitors

NASA Astrophysics Data System (ADS)

Lv, Lingxiao; Fan, Yueqiong; Chen, Qing; Zhao, Yang; Hu, Yue; Zhang, Zhipan; Chen, Nan; Qu, Liangti

2014-06-01

A three-dimensional (3D) carbon quantum dot (CQD) aerogel has been prepared by in situ assembling CQDs in the sol-gel polymerization of resorcinol (R) and formaldehyde (F) and subsequently pyrolyzing the formed CQD gel. Compared to the supercapacitor based on the CQD-free aerogel, the supercapacitor fabricated with the CQD aerogel showed 20-fold higher specific capacitance (294.7 F g-1 at the current density of 0.5 A g-1) and an excellent stability over 1000 consecutive charge-discharge cycles.

Method of low pressure and/or evaporative drying of aerogel

DOEpatents

Mayer, S.T.; Kaschmitter, J.L.; Pekala, R.W.

1995-05-30

A process is described whereby Resorcinol/Formaldehyde (RF) aerogel having a density of about 0.4--1.2 g/cc can be manufactured using a simple air drying procedure. This process is inherently simpler, quicker, and less expensive than the more conventional supercritical or subcritical CO{sub 2} extraction procedures. RF aerogels can be used as produced, such as in insulation applications, or pyrolyzed to form carbon aerogels with a density of about 0.9 g/cc for use in applications such as batteries, supercapacitors, etc.

Thio-,amine-,nitro-,and macrocyclic containing organic aerogels & xerogels

DOEpatents

Fox, Glenn A.; Tillotson, Thomas M.

2005-08-02

An organic aerogel or xerogel formed by a sol-gel reaction using starting materials that exhibit similar reactivity to the most commonly used resorcinol starting material. The new starting materials, including thio-, amine- and nitro-containing molecules and functionalized macrocyclic molecules will produce organic xerogels and aerogels that have improved performance in the areas of detection and sensor technology, as well as water stream remediation. Also, further functionalization of these new organic aerogels or xerogels will yield material that can be extracted with greater facility than current organic aerogels.

Expedited Synthesis of Fluorine-18 Labeled Phenols. A Missing Link in PET Radiochemistry

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

Katzenellenbogen, John A.; Zhou, Dong

Fluorine-18 (F-18) is arguably the most valuable radionuclide for positron emission tomographic (PET) imaging. However, while there are many methods for labeling small molecules with F-18 at aliphatic positions and on electron-deficient aromatic rings, there are essentially no reliable and practical methods to label electron-rich aromatic rings such as phenols, with F-18 at high specific activity. This is disappointing because fluorine-labeled phenols are found in many drugs; there are also many interesting plant metabolites and hormones that contain either phenols or other electron-rich aromatic systems such as indoles whose metabolism, transport, and distribution would be interesting to study if theymore » could readily be labeled with F-18. Most approaches to label phenols with F-18 involve the labeling of electron-poor precursor arenes by nucleophilic aromatic substitution, followed by subsequent conversion to phenols by oxidation or other multi-step sequences that are often inefficient and time consuming. Thus, the lack of good methods for labeling phenols and other electron-rich aromatics with F-18 at high specific activity represents a significant methodological gap in F-18 radiochemistry that can be considered a “Missing Link in PET Radiochemistry”. The objective of this research project was to develop and optimize a series of unusual synthetic transformations that will enable phenols (and other electron-rich aromatic systems) to be labeled with F-18 at high specific activity, rapidly, reliably, and conveniently, thereby bridging this gap. Through the studies conducted with support of this project, we have substantially advanced synthetic methodology for the preparation of fluorophenols. Our progress is presented in detail in the sections below, and much has been published or presented publication; other components are being prepared for publication. In essence, we have developed a completely new method to prepare o-fluorophenols from non-aromatic precursors (diazocyclohexenones) by a novel reaction sequence that uses fluoride ion as a precursor and various activating electrophiles, and we have improved methods for the preparation of heterodiaryl iodonium salts. Both methods have been used to prepare interesting potential radiotracers. Other advances have been made in labeling dendrimeric nanoparticle structures of increasing interest for multimodal imaging and in advancing labeling through fluorosilane bonds. Thus, the progress we have made substantially fills the significant gap in PET radiochemistry that we originally identified, and it provides for the field new methodology that can be applied to a number of current challenges, including the preparation of several molecules of interest as radiotracers, such as 2-[18F]Fluoroestradiol (2-FES) and m-fluorotyrosine, which we have illustrated. These methods can be used by any skilled radiochemist interesting in preparing these agents or similar fluorine-18 labeled electron-rich arene systems of interested for PET biological imaging in the most general sense.« less

Selective phenol methylation to 2,6-dimethylphenol in a fluidized bed of iron-chromium mixed oxide catalyst with o-cresol circulation.

PubMed

Zukowski, Witold; Berkowicz, Gabriela; Baron, Jerzy; Kandefer, Stanisław; Jamanek, Dariusz; Szarlik, Stefan; Wielgosz, Zbigniew; Zielecka, Maria

2014-01-01

2,6-dimethylphenol (2,6-DMP) is a product of phenol methylation, especially important for the plastics industry. The process of phenol methylation in the gas phase is strongly exothermic. In order to ensure good temperature equalization in the catalyst bed, the process was carried out using a catalyst in the form of a fluidized bed - in particular, the commercial iron-chromium catalyst TZC-3/1. Synthesis of 2,6-dimethylphenol from phenol and methanol in fluidized bed of iron-chromium catalyst was carried out and the fluidization of the catalyst was examined. Stable state of fluidized bed of iron-chromium catalyst was achieved. The measured velocities allowed to determine the minimum flow of reactants, ensuring introduction of the catalyst bed in the reactor into the state of fluidization. Due to a high content of o-cresol in products of 2,6-dimethylphenol synthesis, circulation in the technological node was proposed. A series of syntheses with variable amount of o-cresol in the feedstock allowed to determine the parameters of stationary states. A stable work of technological node with o-cresol circulation is possible in the temperature range of350-380°C, and o-cresolin/phenolin molar ratio of more than 0.48. Synthesis of 2,6-DMP over the iron-chromium catalyst is characterized by more than 90% degree of phenol conversion. Moreover, the O-alkylation did not occur (which was confirmed by GC-MS analysis). By applying o-cresol circulation in the 2,6-DMP process, selectivity of more than 85% degree of 2,6-DMP was achieved. The participation levels of by-products: 2,4-DMP and 2,4,6-TMP were low. In the optimal conditions based on the highest yield of 2,6-DMP achieved in the technological node applying o-cresol circulation, there are 2%mol. of 2,4-DMP and 6%mol. of 2,4,6-TMP in the final mixture, whereas 2,4,6-TMP can be useful as a chain stopper and polymer's molar mass regulator during the polymerization of 2,6-DMP.

Inhalation by design: novel ultra-long-acting β(2)-adrenoreceptor agonists for inhaled once-daily treatment of asthma and chronic obstructive pulmonary disease that utilize a sulfonamide agonist headgroup.

PubMed

Glossop, Paul A; Lane, Charlotte A L; Price, David A; Bunnage, Mark E; Lewthwaite, Russell A; James, Kim; Brown, Alan D; Yeadon, Michael; Perros-Huguet, Christelle; Trevethick, Michael A; Clarke, Nicholas P; Webster, Robert; Jones, Rhys M; Burrows, Jane L; Feeder, Neil; Taylor, Stefan C J; Spence, Fiona J

2010-09-23

A novel series of potent and selective sulfonamide derived β(2)-adrenoreceptor agonists are described that exhibit potential as inhaled ultra-long-acting bronchodilators for the treatment of asthma and chronic obstructive pulmonary disease. Analogues from this series mediate very long-lasting smooth muscle relaxation in guinea pig tracheal strips. The sulfonamide agonist headgroup confers high levels of intrinsic crystallinity that could relate to the acidic sulfonamide motif supporting a zwitterionic form in the solid state. Optimization of pharmacokinetic properties was achieved through targeted introduction of a phenolic moiety to support rapid phase II clearance, thereby minimizing systemic exposure following inhalation and reducing systemically mediated adverse events. Compound 38 (PF-610355) is identified as a clinical candidate from this series, with in vivo duration of action studies confirming its potential for once-daily use in humans. Compound 38 is currently in advanced phase II clinical studies.

40 CFR 721.10238 - Formaldehyde, polymers with acetone-phenol reaction products and phenol, potassium sodium salts.

Code of Federal Regulations, 2012 CFR

2012-07-01

...-phenol reaction products and phenol, potassium sodium salts. 721.10238 Section 721.10238 Protection of..., polymers with acetone-phenol reaction products and phenol, potassium sodium salts. (a) Chemical substance..., polymers with acetone-phenol reaction products and phenol, potassium sodium salts (PMN P-09-147; CAS No...

40 CFR 721.10238 - Formaldehyde, polymers with acetone-phenol reaction products and phenol, potassium sodium salts.

Code of Federal Regulations, 2014 CFR

2014-07-01

...-phenol reaction products and phenol, potassium sodium salts. 721.10238 Section 721.10238 Protection of..., polymers with acetone-phenol reaction products and phenol, potassium sodium salts. (a) Chemical substance..., polymers with acetone-phenol reaction products and phenol, potassium sodium salts (PMN P-09-147; CAS No...

40 CFR 721.10238 - Formaldehyde, polymers with acetone-phenol reaction products and phenol, potassium sodium salts.

Code of Federal Regulations, 2013 CFR

2013-07-01

...-phenol reaction products and phenol, potassium sodium salts. 721.10238 Section 721.10238 Protection of..., polymers with acetone-phenol reaction products and phenol, potassium sodium salts. (a) Chemical substance..., polymers with acetone-phenol reaction products and phenol, potassium sodium salts (PMN P-09-147; CAS No...

Simultaneous estimation of phenolic acids in sea buckthorn (Hippophaë rhamnoides) using RP-HPLC with DAD.

PubMed

Arimboor, Ranjith; Kumar, K Sarin; Arumughan, C

2008-05-12

A RP-HPLC-DAD method was developed and validated for the simultaneous analysis of nine phenolic acids including gallic acid, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, salicylic acid, p-coumaric acid, cinnamic acid, caffiec acid and ferulic acid in sea buckthorn (SB) (Hippophaë rhamnoides) berries and leaves. The method was validated in terms of linearity, LOD, precision, accuracy and recovery and found to be satisfactory. Phenolic acid derivatives in anatomical parts of SB berries and leaves were separated into free phenolic acids, phenolic acids bound as esters and phenolic acids bound as glycosides and profiled in HPLC. Berry pulp contained a total of 1068 mg/kg phenolic acids, of which 58.8% was derived from phenolic glycosides. Free phenolic acids and phenolic acid esters constituted 20.0% and 21.2%, respectively, of total phenolic acids in SB berry pulp. The total phenolic acid content in seed kernel (5741 mg/kg) was higher than that in berry pulp and seed coat (Table 2). Phenolic acids liberated from soluble esters constituted the major fraction of phenolic acids (57.3% of total phenolic acids) in seed kernel. 8.4% and 34.3% of total phenolic acids in seed kernel were, respectively contributed by free and phenolic acids liberated from glycosidic bonds. The total soluble phenolic acids content in seed coat (448 mg/kg) was lower than that in seed kernel and pulp (Table 2). Proportion of free phenolic acids in total phenolic acids in seed coat was higher than that in seed kernel and pulp. Phenolic acids bound as esters and glycosides, respectively contributed 49.1% and 20.3% of total phenolic acids in seed coat. The major fraction (approximately 70%) of phenolic acids in SB berries was found to be concentrated in the seeds. Gallic acid was the predominant phenolic acid both in free and bound forms in SB berry parts and leaves.

The influence of interactions among phenolic compounds on the antiradical activity of chokeberries (Aronia melanocarpa).

PubMed

Jakobek, Lidija; Seruga, Marijan; Krivak, Petra

2011-06-01

In the present work, interactions between phenolic compounds from chokeberries and their influence on the antiradical activity was studied. Three fractions were isolated from chokeberries containing different classes of phenolic compounds. The first fraction contained a major part of phenolic acids and flavonols, the second anthocyanins, and the third insoluble phenols and proanthocyanidins. The phenolic compound content was determined using high-performance liquid chromatography, and the antiradical activity using the DPPH test. In order to evaluate the effects of interactions between phenolic compounds on the antiradical activity, the antiradical activity of individual phenolic fractions was compared with that obtained by mixing phenolic fractions. Phenolic mixtures showed the decrease in the antiradical activity in comparison with the individual phenolic fractions. These results suggest the existence of complex interactions among phenolic compounds that caused the decrease of the antiradical activity. Interactions among chokeberry phenols promoted a negative synergism.

Synthesis of Optode Thin Layer using Sol Gel Hybrid of Trietoxysiloxane monomer and 3-(Trimethoxysilyl) Propilamine with Ionophore 4-(2-Pyridilazo)-1,3-Benzenadiol (PAR)

NASA Astrophysics Data System (ADS)

Wahyuningsih, S.; Rahmawati, F.; Kamal, S.; Slamet, S.; Yunianto, M.; Rahmawati, P.; Aini, F. N.

2018-03-01

Optode (Optical sensors) is one of the modern chemical sensors in the field of analytical chemistry that has utilized of inorganic polymers. The optode based on MLCT (Metal to Ligand Charge Transfer) (or MMLL’CT, Mixing Metal-Ligand to Ligand Charge Transfer) or LMCT (Ligand to Metal Charge Transfer) phenomenons have beed generated from oktyltrietxysilane, aminopropyltrimethoxysilane and 4-(2-pyrydilazo) resorcinol (abbreviated as OTES-APTS-PAR) for Cu(II), Cr(III), Ni(II), Fe(III), Cd(II), and Zn(II) ions target. The syntheses of thin layer optode were performed by sol gel method followed by evaporation in glass substrat. The formation of 4-(2-pyrydilazo) resorcinol complexes with ions target have gained strong absorption spectras in visible region because of charge transfer phenomenons. The optical sensor of OTES-APTS-PAR was analysed thermal properties using Differential Thermal Analysis (DTA). DTA thermogram showed a glass transition peaks at a temperature of 315.5 °C. Fourier transform Infrared (FTIR) spectras have showed that the optode materials consisted NH aryl groups indicated IR absorption at 1577.7 cm-1 and also –CH aromatic at 1469.0 cm-1. Synthesized optode materials have strong broad visible absorption with the maximum wavelengths (λmax) = 405 nm and 508.5 nm, respectively. This material have excellent optical responds to several metal ions such as Cu(II), Cr(III), Ni(II), Fe(III), Cd(II), and Zn(II) that was showed from huge Δλmax and the increase of Ktotal

Synthesis and antioxidant activity of curcumin analogs.

PubMed

Zheng, Qu-Tong; Yang, Ze-Hua; Yu, Liu-Ying; Ren, Yu-Yan; Huang, Qiu-Xia; Liu, Qiu; Ma, Xiang-Yu; Chen, Zi-Kang; Wang, Zong-Bao; Zheng, Xing

2017-05-01

Numerous biological activities including antioxidant, antitumor, anti-inflammation, and antivirus of the natural product curcumin were reported. However, the clinical application of it was significantly limited by its instability, poor solubility, less body absorbing, and low bioavailability. This review focuses on the structure modification and antioxidant activity evaluation of curcumin. To study the structure-activity relationship (SAR), five series of curcumin analogs were synthesized and their antioxidant activity were evaluated in vitro. The results showed that electron-donating groups, especially the phenolic hydroxyl group are an essential component to improve the antioxidant activity.

Design, Synthesis, and Evaluation of Novel 2,6-Disubstituted Phenol Derivatives as General Anesthetics.

PubMed

Qin, Linlin; Ren, Lei; Wan, Songlin; Liu, Guoliang; Luo, Xinfeng; Liu, Zhenhong; Li, Fangqiong; Yu, Yan; Liu, Jianyu; Wei, Yonggang

2017-05-11

A novel series of optically active 2,6-disubstituted alkylphenols with improved anesthetic profiles compared to widely used propofol were synthesized. The incorporation of the cyclopropyl group not only increased the steric effect but also introduced stereoselective effects over their anesthetic properties. Compounds 1, 2, and 6 were selected as potential candidates for further preclinical development including studies of their water-soluble prodrugs. Clinical studies of candidate compound 6 (Haisco HSK3486) as a general anesthetic are being performed in Australia and China.

Nerve lesioning with direct current

NASA Astrophysics Data System (ADS)

Ravid, E. Natalie; Shi Gan, Liu; Todd, Kathryn; Prochazka, Arthur

2011-02-01

Spastic hypertonus (muscle over-activity due to exaggerated stretch reflexes) often develops in people with stroke, cerebral palsy, multiple sclerosis and spinal cord injury. Lesioning of nerves, e.g. with phenol or botulinum toxin is widely performed to reduce spastic hypertonus. We have explored the use of direct electrical current (DC) to lesion peripheral nerves. In a series of animal experiments, DC reduced muscle force by controlled amounts and the reduction could last several months. We conclude that in some cases controlled DC lesioning may provide an effective alternative to the less controllable molecular treatments available today.

Poly(3-hydroxybutyrate)-ethyl cellulose based bio-composites with novel characteristics for infection free wound healing application.

PubMed

Iqbal, Hafiz M N; Kyazze, Godfrey; Locke, Ian Charles; Tron, Thierry; Keshavarz, Tajalli

2015-11-01

A series of bio-composites including poly3-hydroxybutyrate [P(3HB)] grafted ethyl cellulose (EC) stated as P(3HB)-EC were successfully synthesised. Furthermore, natural phenols e.g., p-4-hydroxybenzoic acid (HBA) and ferulic acid (FA) were grafted onto the newly developed P(3HB)-EC-based bio-composites under laccase-assisted environment without the use of additional initiators or crosslinking agents. The phenol grafted bio-composites were critically evaluated for their antibacterial and biocompatibility features as well as their degradability in soil. In particular, the results of the antibacterial evaluation for the newly developed bio-composites indicated that 20HBA-g-P(3HB)-EC and 15FA-g-P(3HB)-EC bio-composites exerted strong bactericidal and bacteriostatic activity against Gram(-)E. coli NTCT 10418 as compared to the Gram(+)B. subtilis NCTC 3610. This study shows further that at various phenolic concentrations the newly synthesised bio-composites remained cytocompatible with human keratinocyte-like HaCaT skin cells, as 100% cell viability was recorded, in vitro. As for the degradation, an increase in the degradation rate was recorded during the soil burial analyses over a period of 42 days. These findings suggest that the reported bio-composites have great potential for use in wound healing; covering the affected skin area which may favour tissue repair over shorter periods. Copyright © 2015 Elsevier B.V. All rights reserved.

Grape skin phenolics as inhibitors of mammalian α-glucosidase and α-amylase--effect of food matrix and processing on efficacy.

PubMed

Lavelli, V; Sri Harsha, P S C; Ferranti, P; Scarafoni, A; Iametti, S

2016-03-01

Type-2 diabetes is continuously increasing worldwide. Hence, there is a need to develop functional foods that efficiently alleviate damage due to hyperglycaemia complications while meeting the criteria for a sustainable food processing technology. Inhibition of mammalian α-amylase and α-glucosidase was studied for white grape skin samples recovered from wineries and found to be higher than that of the drug acarbose. In white grape skins, quercetin and kaempferol derivatives, analysed by UPLC-DAD-MS, and the oligomeric series of catechin/epicatechin units and their gallic acid ester derivatives up to nonamers, analysed by MALDI-TOF-MS were identified. White grape skin was then used for enrichment of a tomato puree (3%) and a flat bread (10%). White grape skin phenolics were found in the extract obtained from the enriched foods, except for the higher mass proanthocyanidin oligomers, mainly due to their binding to the matrix and to a lesser extent to heat degradation. Proanthocyanidin solubility was lower in bread, most probably due to formation of binary proanthocyanin/protein complexes, than in tomato puree where possible formation of ternary proanthocyanidin/protein/pectin complexes can enhance solubility. Enzyme inhibition by the enriched foods was significantly higher than for unfortified foods. Hence, this in vitro approach provided a platform to study potential dietary agents to alleviate hyperglycaemia damage and suggested that grape skin phenolics could be effective even if the higher mass proanthocyanidins are bound to the food matrix.

[Formation mechanism and chemical safety of nonintentional chemical substances present in chlorinated drinking water and wastewater].

PubMed

Onodera, Sukeo

2010-09-01

This paper reviews the formation mechanism and chemical safety of nonintentional chemical substances (NICS) present in chlorine-treated water containing organic contaminants. Undesirable compounds, i.e., NICS, may be formed under certain conditions when chlorine reacts with organic matter. The rate and extent of chlorine consumption with organics are strongly dependent on their chemical structures, particularly whether double bonds or sulfur and nitrogen atoms occur in the molecules. Organothiophosphorus pesticides (P=S type) are easily oxidized to their phosphorus compounds (P=O type) in chlorinated water containing HOCl as little as 0.5 mg/l, resulting in an increase in cholinesterase-inhibitory activity. Chlorination of phenols in water also produces a series of highly chlorinated compounds, including chlorophenols, chloroquinones, chlorinated carboxylic acids, and polychlorinated phenoxyphenols (PCPPs). In some of these chloroquinones, 2,6-dichloroalkylsemiquinones exhibit a strong mutagenic response as do positive controls used in the Ames test. 2-phenoxyphenols in these PCPPs are particularly interesting, as they are present in the chlorine-treated phenol solution and they are also precursors (predioxins) of the highly toxic chlorinated dioxins. Polynuclear aromatic hydrocarbons (PAHs) were found to undergo chemical changes due to hypochlorite reactions to give chloro-substituted PAHs, oxygenated (quinones) and hydroxylated (phenols) compounds, but they exhibit a lower mutagenic response. In addition, field work was performed in river water and drinking water to obtain information on chemical distribution and their safety, and the results are compared with those obtained in the model chlorination experiments.

Single-step synthesis of a new series of meso di-Mannich bases from the cyclic aminal (2S,7R,11S,16R)-1,8,10,17-tetraazapentacyclo[8.8.1.1.8,170.2,7011,16]icosane and p-substituted phenols

PubMed Central

2013-01-01

Background The results presented herein show that the cyclic aminal (2S,7R,11S,16R)-1,8,10,17-tetraazapentacyclo[8.8.1.1.8,170.2,7011,16]icosane (6), derived from cis-(meso)-1,2-diaminocyclohexane and formaldehyde, is a suitable substrate for the preption of a series of cis-meso Mannich bases such as 8a-l by reaction with p-substituted phenols 7a-l in basic media. These compounds are valuable synthetic products and may find application in asymmetric catalysis. Results The products were characterized principally by NMR and IR spectroscopy. Both the benzylic and aminalic protons of the perhydrobenzimidazolidine moiety were diastereotopic due to the presence of stereogenic nitrogen centers. The occurrence of intramolecular hydrogen bonding interactions was confirmed by the broad OH stretching vibration band in the IR spectra. Vibrational spectra were calculated using B3LYP at 6-31G(d,p) level, and the calculated frequencies for the νOH vibrations were compared to those of the experimental spectra. Hydrogen bonding interactions in the solid state were observed through the X-ray crystallography of 8j. Additionally, Mulliken charges and Fukui indices for 6 were calculated as theoretical descriptors of electrophilicity. Conclusion A new series of meso Mannich bases called 4,4′-disubstituted-2,2′-{[(3aR,7aS)-2,3,3a,4,5,6,7,7a-octahydro-1H-1,3-benzimidazole-1,3-diyl]bis(methylene)} diphenols (8a-l) which are derived from cis-(meso)-1,2-diaminocyclohexane, were obtained from cyclic aminal 6. These results confirmed the behavior of 6 as an electrophilic preformed reagent in Mannich reactions in basic media. PMID:23758899

Screening of high concentration phenol degrading strain and optimization of its phenol degradation performance

NASA Astrophysics Data System (ADS)

Zhang, Yue-Hua; Li, Jing; Wang, Xue; Xue, Chun-Mei

2018-03-01

As phenol as the sole carbon source, the activated sludge was screened and acclimated to obtain the superior phenol-degrading bacteria capable of degrading high phenol concentration. The mixed bacteria completely degraded 1700mg/L phenol in 15h, to 102.9mg/L; the degradation rate reached 96.9%. After isolation and purification, four different single strains were obtained, and the genus of each strain was preliminarily identified. At the same time, the effects of initial phenol concentration, bacteria dosage, temperature and pH on the degradation of COD and phenol by phenol-degrading bacteria were also investigated. The mixed bacteria de-phenol effect is better than the four isolates were isolated.

Investigation of chitosan-phenolics systems as wood adhesives.

PubMed

Peshkova, Svetlana; Li, Kaichang

2003-04-24

Chitosan-phenolics systems were investigated as wood adhesives. Adhesion between two pieces of wood veneer developed only when all three components-chitosan, a phenolic compound, and laccase-were present. For the adhesive systems containing a phenolic compound with only one phenolic hydroxyl group, adhesive strengths were highly dependent upon the chemical structures of phenolic compounds used in the system and the relative oxidation rates of the phenolic compounds by laccase. The adhesive strengths were also directly related to the viscosity of the adhesive systems. However, for the adhesive systems containing a phenolic compound with two or three phenolic hydroxyl groups adjacent to each other, no correlations among adhesive strengths, relative oxidation rates of the phenolic compounds by laccase, and viscosities were observed. The adhesion mechanisms of these chitosan-phenolics systems were proposed to be similar to those of mussel adhesive proteins.

Hierarchical activated mesoporous phenolic-resin-based carbons for supercapacitors.

PubMed

Wang, Zhao; Zhou, Min; Chen, Hao; Jiang, Jingui; Guan, Shiyou

2014-10-01

A series of hierarchical activated mesoporous carbons (AMCs) were prepared by the activation of highly ordered, body-centered cubic mesoporous phenolic-resin-based carbon with KOH. The effect of the KOH/carbon-weight ratio on the textural properties and capacitive performance of the AMCs was investigated in detail. An AMC prepared with a KOH/carbon-weight ratio of 6:1 possessed the largest specific surface area (1118 m(2) g(-1)), with retention of the ordered mesoporous structure, and exhibited the highest specific capacitance of 260 F g(-1) at a current density of 0.1 A g(-1) in 1 M H2 SO4 aqueous electrolyte. This material also showed excellent rate capability (163 F g(-1) retained at 20 A g(-1)) and good long-term electrochemical stability. This superior capacitive performance could be attributed to a large specific surface area and an optimized micro-mesopore structure, which not only increased the effective specific surface area for charge storage but also provided a favorable pathway for efficient ion transport. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

An outbreak of illness among aerospace workers.

PubMed Central

Sparks, P. J.; Simon, G. E.; Katon, W. J.; Altman, L. C.; Ayars, G. H.; Johnson, R. L.

1990-01-01

A multispecialty panel of physicians evaluated a case series of 53 composite-materials workers in a large aircraft manufacturing facility who filed workers' compensation claims for illness labeled by the media as the "aerospace syndrome." Possible skin and respiratory tract exposures included formaldehyde, phenol, particulates, epoxy resins, and trace organic solvents, but measured concentrations were well below all regulatory and consensus standards. Most workers had histories of transient skin or respiratory tract irritation consistent with the known potential toxicity of these materials. None of the workers tested had immunoglobulin IgG or IgE antibodies to human serum albumin complexed with formaldehyde. A majority (74%) met DSM-III-R [Diagnostic and Statistical Manual of Mental Disorders, 3rd edition, revised] criteria for major depression, panic disorder, or both. Most of these psychiatric disorders were of a recent onset, correlating in time with the use of phenol- and formaldehyde-impregnated composite material. Psychosocial factors were thought to have played a major role in the high prevalence of illness in this group and should be evaluated directly in well-controlled epidemiologic studies of similar crisis-building situations in the future. PMID:2098006

Structural characterization and identification of iridoid glycosides, saponins, phenolic acids and flavonoids in Flos Lonicerae Japonicae by a fast liquid chromatography method with diode-array detection and time-of-flight mass spectrometry.

PubMed

Qi, Lian-Wen; Chen, Chun-Yun; Li, Ping

2009-10-01

A fast liquid chromatography method with diode-array detection (DAD) and time-of-flight mass spectrometry (TOF-MS) has been developed for analysis of constituents in Flos Lonicerae Japonicae (FLJ), a traditional Chinese medicine derived from the flower bud of Lonicera japonica. The chromatographic analytical time decreased to 25 min without sacrificing resolution using a column packed with 1.8-microm porous particles (4.6 x 50 mm), three times faster than the performance of conventional 5.0-microm columns (4.6 x 150 mm). Four major groups of compounds previously isolated from FLJ were structurally characterized by DAD-TOF-MS: iridoid glycosides showed maximum UV absorption at 240 nm; phenolic acids at 217, 242, and 326 nm; flavonoids at 255 and 355 nm; while saponins had no absorption. In electrospray ionization (ESI)-TOF-MS experiments, elimination of a glucose unit (162 Da), and successive losses of H(2)O, CH(3)OH and CO, were generally observed in iridoid glycosides; saponins were characterized by a series of identical aglycone ions; phenolic acids typically generated a base peak at [M-H-caffeoyl](-) by loss of a caffeic acid unit (162 Da) and several marked quinic acid moiety ions; cleavage of the glycosidic bond (loss of 162 or 308 Da), subsequent losses of H(2)O, CO, RDA and C-ring fragmentation were the most possible fragmentation pathways for flavonoids. By accurate mass measurements within 4 ppm error for each molecular ion and subsequent fragment ions, as well as the 'full mass spectral' information of TOF-MS, a total of 41 compounds including 13 iridoid glycosides, 11 phenolic acids, 7 saponins, and 10 flavonoids were identified in a methanolic extract of FLJ. Copyright (c) 2009 John Wiley & Sons, Ltd.

Effect of processing on phenolic acids composition and radical scavenging capacity of barley pasta.

PubMed

De Paula, Rosanna; Rabalski, Iwona; Messia, Maria Cristina; Abdel-Aal, El-Sayed M; Marconi, Emanuele

2017-12-01

Phenolic acids, total phenolics content and DPPH radical scavenging capacity in raw ingredients, fresh and dried spaghetti, and in uncooked and cooked spaghetti were evaluated and compared with semolina spaghetti as a reference. Ferulic acid was the major phenolic acid found in the free and bound phenolic extracts in all the investigated pasta samples. The addition of barley flour into pasta at incorporation levels of 30, 50 and 100% increased phenolic acids and total phenolics content. Pasta processing did not significantly affect the total phenolics content and free radical scavenging capacity, but a significant reduction in total phenolic acids measured by HPLC was found. Drying process differently affected individual phenolic compounds in the free and bound fractions, and thus, the total phenolic acids content. Free vanillic, caffeic and p-coumaric acids did not significantly change, while p-hydroxybenzoic and ferulic acids of the free extracts showed higher values compared to the corresponding fresh pasta. Cooking did not greatly affect total phenolic acids, more leading to conserving free and bound phenolic compounds. Copyright © 2017 Elsevier Ltd. All rights reserved.

Treatment of phenolic wastewater in an anaerobic fixed bed reactor (AFBR) - recovery after shock loading.

PubMed

Bajaj, Mini; Gallert, Claudia; Winter, Josef

2009-03-15

An anaerobic fixed bed reactor (AFBR) was run for 550 days with a mixed microbial flora to stabilize synthetic wastewater that contained glucose and phenol as main carbon sources. The influent phenol concentration was gradually increased from 2 to 40 mmol/l within 221 days. The microbial flora was able to adapt to this high phenol concentration with an average of 94% phenol removal. Microbial adaptation at such a high phenol concentration is not reported elsewhere. The maximum phenol removal observed before the phenol shock load was 39.47 mmol/l or 3.7 g phenol/l at a hydraulic retention time (HRT) of 2.5 days and an organic loading rate (OLR) of 5.3 g/l.d which amounts to a phenol removal rate of ca. 15.8 mmol phenol/l.d. The chemical oxygen demand (COD) removal before exposing the reactor to a shock load corresponded with phenol removal. A shock load was induced in the reactor by increasing the phenol concentration from 40 to 50 mmol/l in the influent. The maximum phenol removal rate observed after shock load was 18 mmol/l.d at 5.7 g COD/l.d. But this was not a stable rate and a consistent drop in COD and phenol removal was observed for 1 week, followed by a sharp decline and production of fatty acids. Recovery of the reactor was possible only when no feed was provided to the reactor for 1 month and the phenol concentration was increased gradually. When glucose was omitted from the influent, unknown intermediates of anaerobic phenol metabolism were observed for some time.

Ultrasonic activated efficient synthesis of chromenes using amino-silane modified Fe3O4 nanoparticles: A versatile integration of high catalytic activity and facile recovery

NASA Astrophysics Data System (ADS)

Safari, Javad; Zarnegar, Zohre

2014-08-01

An efficient synthesis of 2-amino-4H-chromenes is achieved by one pot three component coupling reaction of aldehyde, malononitrile, and resorcinol using amino-silane modified Fe3O4 nanoparticles (MNPs-NH2) heterogeneous nanocatalyst under sonic condition. The attractive advantages of the present process are mild reaction conditions, short reaction times, easy isolation of products, good yields and simple operational procedures. Combination of the advantages of ultrasonic irradiation and magnetic nanoparticles provides important methodology to carry out catalytic transformations.

Tunable Graphitic Carbon Nano-Onions Development in Carbon Nanofibers for Multivalent Energy Storage

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

Schwarz, Haiqing L.

2016-01-01

We developed a novel porous graphitic carbon nanofiber material using a synthesis strategy combining electrospinning and catalytic graphitization. RF hydrogel was used as carbon precursors, transition metal ions were successfully introduced into the carbon matrix by binding to the carboxylate groups of a resorcinol derivative. Transition metal particles were homogeneously distributed throughout the carbon matrix, which are used as in-situ catalysts to produce graphitic fullerene-like nanostructures surrounding the metals. The success design of graphitic carbons with enlarged interlayer spacing will enable the multivalent ion intercalation for the development of multivalent rechargeable batteries.

Phenol red-silk tyrosine cross-linked hydrogels.

PubMed

Sundarakrishnan, Aswin; Herrero Acero, Enrique; Coburn, Jeannine; Chwalek, Karolina; Partlow, Benjamin; Kaplan, David L

2016-09-15

Phenol red is a cytocompatible pH sensing dye that is commonly added to cell culture media, but removed from some media formulations due to its structural mimicry of estrogen. Phenol red free media is also used during live cell imaging, to avoid absorbance and fluorescence quenching of fluorophores. To overcome these complications, we developed cytocompatible and degradable phenol red-silk tyrosine cross-linked hydrogels using horseradish peroxidase (HRP) enzyme and hydrogen peroxide (H2O2). Phenol red added to silk during tyrosine crosslinking accelerated di-tyrosine formation in a concentration-dependent reaction. Phenol red diffusion studies and UV-Vis spectra of phenol red-silk tyrosine hydrogels at different pHs showed altered absorption bands, confirming entrapment of dye within the hydrogel network. LC-MS of HRP-reacted phenol red and N-acetyl-l-tyrosine reaction products confirmed covalent bonds between the phenolic hydroxyl group of phenol red and tyrosine on the silk. At lower phenol red concentrations, leak-proof hydrogels which did not release phenol red were fabricated and found to be cytocompatible based on live-dead staining and alamar blue assessments of encapsulated fibroblasts. Due to the spectral overlap between phenol red absorbance at 415nm and di-tyrosine fluorescence at 417nm, phenol red-silk hydrogels provide both absorbance and fluorescence-based pH sensing. With an average pKa of 6.8 and good cytocompatibiltiy, phenol red-silk hydrogels are useful for pH sensing in phenol red free systems, cellular microenvironments and bioreactors. Phenol red entrapped within hydrogels facilitates pH sensing in phenol red free environments. Leak-proof phenol red based pH sensors require covalent binding techniques, but are complicated due to the lack of amino or carboxyl groups on phenol red. Currently, there is no simple, reliable technique to covalently link phenol red to hydrogel matrices, for real-time pH sensing in cell culture environments. Herein, we take advantage of phenolic groups for covalent linkage of phenol red to silk tyrosine in the presence of HRP and H2O2. The novelty of the current system stems from its simplicity and the use of silk protein to create a cytocompatible, degradable sensor capable of real-time pH sensing in cell culture microenvironments. Copyright © 2016 Acta Materialia Inc. Published by Elsevier Ltd. All rights reserved.

Survey of sensitizing components of oxidative hair dyes (retail and professional products) in Germany.

PubMed

Kirchlechner, Stephan; Hübner, Anja; Uter, Wolfgang

2016-07-01

Components of oxidative hair dyes, such as p-toluylenediamine, are very potent contact sensitizers to which many consumers as well as hairdressers and their clients are commonly exposed. Based on the qualitative composition of both retail and professional haircare products as determined by package labeling (according to INCI), we conducted a survey on the exposure to active components of oxidative hair dyes in Germany. The joint occurrence of components is also discussed. Nearly all of the 20 most commonly used substances are potent or very potent contact sensitizers. Contained in 88 % of all products, p-toluylenediamine is the most common component. There are only minor differences between retail and professional products. A frequent combination of substances includes p-toluylenediamine (sulfate), resorcinol as well as m-aminophenol. However, their actual concentrations (which were not investigated in this study) may vastly differ depending on the shade of the individual hair dye. Descriptive univariate analysis reveals that the currently used patch test series "Hairdressing Chemicals", as recommended by the German Contact Allergy Research Group (DKG), does not adequately cover the spectrum of allergens consumers and professionals are exposed to. Other studies have also suggested that a number of other allergens should be tested as well. Taking into account the dynamic kinetics of oxidative hair dyes with respect to allergy development, the effects of combined simultaneous exposure to multiple allergens on the risk of sensitization requires further research. © 2016 Deutsche Dermatologische Gesellschaft (DDG). Published by John Wiley & Sons Ltd.

Biological removal of phenol from wastewaters: a mini review

NASA Astrophysics Data System (ADS)

Pradeep, N. V.; Anupama, S.; Navya, K.; Shalini, H. N.; Idris, M.; Hampannavar, U. S.

2015-06-01

Phenol and its derivatives are common water pollutants and include wide variety of organic chemicals. Phenol poisoning can occur by skin absorption, inhalation, ingestion and various other methods which can result in health effects. High exposures to phenol may be fatal to human beings. Accumulation of phenol creates toxicity both for flora and fauna. Therefore, removal of phenol is crucial to perpetuate the environment and individual. Among various treatment methods available for removal of phenols, biodegradation is environmental friendly. Biological methods are gaining importance as they convert the wastes into harmless end products. The present work focuses on assessment of biological removal (biodegradation) of phenol. Various factors influence the efficiency of biodegradation of phenol such as ability of the microorganism, enzymes involved, the mechanism of degradation and influencing factors. This study describes about the sources of phenol, adverse effects on the environment, microorganisms involved in the biodegradation (aerobic and anaerobic) and enzymes that polymerize phenol.

Parabola-like shaped pH-rate profile for phenols oxidation by aqueous permanganate.

PubMed

Du, Juanshan; Sun, Bo; Zhang, Jing; Guan, Xiaohong

2012-08-21

Oxidation of phenols by permanganate in the pH range of 5.0-9.0 generally exhibits a parabola-like shape with the maximum reaction rate obtained at pH close to phenols' pK(a). However, a monotonic increase or decrease is observed if phenols' pK(a) is beyond the pH range of 5.0-9.0. A proton transfer mechanism is proposed in which the undissociated phenol is directly oxidized by permanganate to generate products while a phenolate-permanganate adduct, intermediate, is formed between dissociated phenol and permanganate ion and this is the rate-limiting step for phenolates oxidation by permanganate. The intermediate combines with H(+) and then decomposes to products. Rate equations derived based on the steady-state approximation can well simulate the experimentally derived pH-rate profiles. Linear free energy relationships (LFERs) were established among the parameters obtained from the modeling, Hammett constants, and oxygen natural charges in phenols and phenolates. LFERs reveal that chlorine substituents have opposite influence on the susceptibility of phenols and phenolates to permanganate oxidation and phenolates are not necessarily more easily oxidized than their neutral counterparts. The chlorine substituents regulate the reaction rate of chlorophenolates with permanganate mainly by influencing the natural charges of the oxygen atoms of dissociated phenols while they influence the oxidation of undissociated chlorophenols by permanganate primarily by forming intramolecular hydrogen bonding with the phenolic group.

Reaction pathways of proton transfer in hydrogen-bonded phenol-carboxylate complexes explored by combined UV-vis and NMR spectroscopy.

PubMed

Koeppe, Benjamin; Tolstoy, Peter M; Limbach, Hans-Heinrich

2011-05-25

Combined low-temperature NMR/UV-vis spectroscopy (UVNMR), where optical and NMR spectra are measured in the NMR spectrometer under the same conditions, has been set up and applied to the study of H-bonded anions A··H··X(-) (AH = 1-(13)C-2-chloro-4-nitrophenol, X(-) = 15 carboxylic acid anions, 5 phenolates, Cl(-), Br(-), I(-), and BF(4)(-)). In this series, H is shifted from A to X, modeling the proton-transfer pathway. The (1)H and (13)C chemical shifts and the H/D isotope effects on the latter provide information about averaged H-bond geometries. At the same time, red shifts of the π-π* UV-vis absorption bands are observed which correlate with the averaged H-bond geometries. However, on the UV-vis time scale, different tautomeric states and solvent configurations are in slow exchange. The combined data sets indicate that the proton transfer starts with a H-bond compression and a displacement of the proton toward the H-bond center, involving single-well configurations A-H···X(-). In the strong H-bond regime, coexisting tautomers A··H···X(-) and A(-)···H··X are observed by UV. Their geometries and statistical weights change continuously when the basicity of X(-) is increased. Finally, again a series of single-well structures of the type A(-)···H-X is observed. Interestingly, the UV-vis absorption bands are broadened inhomogeneously because of a distribution of H-bond geometries arising from different solvent configurations.

Identification of the free phenolic profile of Adlay bran by UPLC-QTOF-MS/MS and inhibitory mechanisms of phenolic acids against xanthine oxidase.

PubMed

Lin, Lianzhu; Yang, Qingyun; Zhao, Kun; Zhao, Mouming

2018-07-01

Adlay bran free phenolic extract has been previously demonstrated to possess potent xanthine oxidase (XOD) inhibitory activity. The aims of this study were to characterize the free phenolic profile of adlay bran and investigate the structure-activity relationship, underlying mechanism and interaction of phenolic acids as XOD inhibitors. A total of twenty phenolics including ten phenolic acids, two coumarins, two phenolic aldedhyes and six flavonoids were identified in a phenolic compound-guided separation by UPLC-QTOF-MS/MS. Adlay bran free phenolic extract possessed strong XOD inhibitory activity related to hydroxycinnamic acids with methoxyl groups. The hydrogen bonding and hydrophobic interactions were the main forces in the binding of adlay phenolics to XOD. Sinapic acid, identified in adlay bran for the first time, possessed strong XOD inhibitory activity in a mixed non-competitive manner, and synergistic effects with other adlay phenolic acids at low concentrations, and would be a promising agent for preventing and treating hyperuricemia. Copyright © 2018. Published by Elsevier Ltd.

Degradation Of Carbon/Phenolic Composites By NaOH

NASA Technical Reports Server (NTRS)

King, H. M.; Semmel, M. L.; Goldberg, B. E.; Clinton, Raymond G., Jr.

1989-01-01

Effects of sodium hydroxide contamination level on physical and chemical properties of phenolic resin and carbon/phenolic composites described in report. NaOH degrades both carbon and phenolic components of carbon/phenolic laminates.

Inhibitory effects of phenolic compounds of rice straw formed by saccharification during ethanol fermentation by Pichia stipitis.

PubMed

Wang, Xiahui; Tsang, Yiu Fai; Li, Yuhao; Ma, Xiubing; Cui, Shouqing; Zhang, Tian-Ao; Hu, Jiajun; Gao, Min-Tian

2017-11-01

In this study, it was found that the type of phenolic acids derived from rice straw was the major factor affecting ethanol fermentation by Pichia stipitis. The aim of this study was to investigate the inhibitory effect of phenolic acids on ethanol fermentation with rice straw. Different cellulases produced different ratios of free phenolic acids to soluble conjugated phenolic acids, resulting in different fermentation efficiencies. Free phenolic acids exhibited much higher inhibitory effect than conjugated phenolic acids. The flow cytometry results indicated that the damage to cell membranes was the primary mechanism of inhibition of ethanol fermentation by phenolic acids. The removal of free phenolic acids from the hydrolysates increased ethanol productivity by 2.0-fold, indicating that the free phenolic acids would be the major inhibitors formed during saccharification. The integrated process for ethanol and phenolic acids may constitute a new strategy for the production of low-cost ethanol. Copyright © 2017 Elsevier Ltd. All rights reserved.

Novel Phenolic Inhibitors of Small/Intermediate-Conductance Ca2+-Activated K+ Channels, KCa3.1 and KCa2.3

PubMed Central

Oliván-Viguera, Aida; Valero, Marta Sofía; Murillo, María Divina; Wulff, Heike; García-Otín, Ángel-Luis; Arbonés-Mainar, José-Miguel; Köhler, Ralf

2013-01-01

Background KCa3.1 channels are calcium/calmodulin-regulated voltage-independent K+ channels that produce membrane hyperpolarization and shape Ca2+-signaling and thereby physiological functions in epithelia, blood vessels, and white and red blood cells. Up-regulation of KCa3.1 is evident in fibrotic and inflamed tissues and some tumors rendering the channel a potential drug target. In the present study, we searched for novel potent small molecule inhibitors of KCa3.1 by testing a series of 20 selected natural and synthetic (poly)phenols, synthetic benzoic acids, and non-steroidal anti-inflammatory drugs (NSAIDs), with known cytoprotective, anti-inflammatory, and/or cytostatic activities. Methodology/Principal Findings In electrophysiological experiments, we identified the natural phenols, caffeic acid (EC50 1.3 µM) and resveratrol (EC50 10 µM) as KCa3.1 inhibitors with moderate potency. The phenols, vanillic acid, gallic acid, and hydroxytyrosol had weak or no blocking effects. Out of the NSAIDs, flufenamic acid was moderately potent (EC50 1.6 µM), followed by mesalamine (EC50≥10 µM). The synthetic fluoro-trivanillic ester, 13b ([3,5-bis[(3-fluoro-4-hydroxy-benzoyl)oxymethyl]phenyl]methyl 3-fluoro-4-hydroxy-benzoate), was identified as a potent mixed KCa2/3 channel inhibitor with an EC50 of 19 nM for KCa3.1 and 360 pM for KCa2.3, which affected KCa1.1 and Kv channels only at micromolar concentrations. The KCa3.1/KCa2-activator SKA-31 antagonized the 13b-blockade. In proliferation assays, 13b was not cytotoxic and reduced proliferation of 3T3 fibroblasts as well as caffeic acid. In isometric vessel myography, 13b increased contractions of porcine coronary arteries to serotonin and antagonized endothelium-derived hyperpolarization-mediated vasorelaxation to pharmacological KCa3.1/KCa2.3 activation. Conclusions/Significance We identified the natural phenols, caffeic acid and resveratrol, the NSAID, flufenamic acid, and the polyphenol 13b as novel KCa3.1 inhibitors. The high potency of 13b with pan-activity on KCa3.1/KCa2 channels makes 13b a new pharmacological tool to manipulate inflammation and cancer growth through KCa3.1/KCa2 blockade and a promising template for new drug design. PMID:23516517

Acinetobacter sp. DW-1 immobilized on polyhedron hollow polypropylene balls and analysis of transcriptome and proteome of the bacterium during phenol biodegradation process.

PubMed

Gu, Qihui; Wu, Qingping; Zhang, Jumei; Guo, Weipeng; Wu, Huiqing; Sun, Ming

2017-07-07

Phenol is a hazardous chemical known to be widely distributed in aquatic environments. Biodegradation is an attractive option for removal of phenol from water sources. Acinetobacter sp. DW-1 isolated from drinking water biofilters can use phenol as a sole carbon and energy source. In this study, we found that Immobilized Acinetobacter sp. DW-1cells were effective in biodegradation of phenol. In addition, we performed proteome and transcriptome analysis of Acinetobacter sp. DW-1 during phenol biodegradation. The results showed that Acinetobacter sp. DW-1 degrades phenol mainly by the ortho pathway because of the induction of phenol hydroxylase, catechol-1,2-dioxygenase. Furthermore, some novel candidate proteins (OsmC-like family protein, MetA-pathway of phenol degradation family protein, fimbrial protein and coenzyme F390 synthetase) and transcriptional regulators (GntR/LuxR/CRP/FNR/TetR/Fis family transcriptional regulator) were successfully identified to be potentially involved in phenol biodegradation. In particular, MetA-pathway of phenol degradation family protein and fimbrial protein showed a strong positive correlation with phenol biodegradation, and Fis family transcriptional regulator is likely to exert its effect as activators of gene expression. This study provides valuable clues for identifying global proteins and genes involved in phenol biodegradation and provides a fundamental platform for further studies to reveal the phenol degradation mechanism of Acinetobacter sp.

Community Analysis and Recovery of Phenol-degrading Bacteria from Drinking Water Biofilters

PubMed Central

Gu, Qihui; Wu, Qingping; Zhang, Jumei; Guo, Weipeng; Wu, Huiqing; Sun, Ming

2016-01-01

Phenol is a ubiquitous organic contaminant in drinking water. Biodegradation plays an important role in the elimination of phenol pollution in the environment, but the information about phenol removal by drinking water biofilters is still lacking. Herein, we study an acclimated bacterial community that can degrade over 80% of 300 mg/L phenol within 3 days. PCR detection of genotypes involved in bacterial phenol degradation revealed that the degradation pathways contained the initial oxidative attack by phenol hydroxylase, and subsequent ring fission by catechol 1,2-dioxygenase. Based on the PCR denatured gradient gel electrophoresis (PCR-DGGE) profiles of bacteria from biological activated carbon (BAC), the predominant bacteria in drinking water biofilters including Delftia sp., Achromobacter sp., and Agrobacterium sp., which together comprised up to 50% of the total microorganisms. In addition, a shift in bacterial community structure was observed during phenol biodegradation. Furthermore, the most effective phenol-degrading strain DW-1 that correspond to the main band in denaturing gradient gel electrophoresis (DGGE) profile was isolated and identified as Acinetobacter sp., according to phylogenetic analyses of the 16S ribosomal ribonucleic acid (rRNA) gene sequences. The strain DW-1 also produced the most important enzyme, phenol hydroxylase, and it also exhibited a good ability to degrade phenol when immobilized on granular active carbon (GAC). This study indicates that the enrichment culture has great potential application for treatment of phenol-polluted drinking water sources, and the indigenous phenol-degrading microorganism could recover from drinking water biofilters as an efficient resource for phenol removal. Therefore, the aim of this study is to draw attention to recover native phenol-degrading bacteria from drinking water biofilters, and use these native microorganisms as phenolic water remediation in drinking water sources. PMID:27148185

Community Analysis and Recovery of Phenol-degrading Bacteria from Drinking Water Biofilters.

PubMed

Gu, Qihui; Wu, Qingping; Zhang, Jumei; Guo, Weipeng; Wu, Huiqing; Sun, Ming

2016-01-01

Phenol is a ubiquitous organic contaminant in drinking water. Biodegradation plays an important role in the elimination of phenol pollution in the environment, but the information about phenol removal by drinking water biofilters is still lacking. Herein, we study an acclimated bacterial community that can degrade over 80% of 300 mg/L phenol within 3 days. PCR detection of genotypes involved in bacterial phenol degradation revealed that the degradation pathways contained the initial oxidative attack by phenol hydroxylase, and subsequent ring fission by catechol 1,2-dioxygenase. Based on the PCR denatured gradient gel electrophoresis (PCR-DGGE) profiles of bacteria from biological activated carbon (BAC), the predominant bacteria in drinking water biofilters including Delftia sp., Achromobacter sp., and Agrobacterium sp., which together comprised up to 50% of the total microorganisms. In addition, a shift in bacterial community structure was observed during phenol biodegradation. Furthermore, the most effective phenol-degrading strain DW-1 that correspond to the main band in denaturing gradient gel electrophoresis (DGGE) profile was isolated and identified as Acinetobacter sp., according to phylogenetic analyses of the 16S ribosomal ribonucleic acid (rRNA) gene sequences. The strain DW-1 also produced the most important enzyme, phenol hydroxylase, and it also exhibited a good ability to degrade phenol when immobilized on granular active carbon (GAC). This study indicates that the enrichment culture has great potential application for treatment of phenol-polluted drinking water sources, and the indigenous phenol-degrading microorganism could recover from drinking water biofilters as an efficient resource for phenol removal. Therefore, the aim of this study is to draw attention to recover native phenol-degrading bacteria from drinking water biofilters, and use these native microorganisms as phenolic water remediation in drinking water sources.

Phenolic composition and antioxidant potential of grain legume seeds: A review.

PubMed

Singh, Balwinder; Singh, Jatinder Pal; Kaur, Amritpal; Singh, Narpinder

2017-11-01

Legumes are a good source of bioactive phenolic compounds which play significant roles in many physiological as well as metabolic processes. Phenolic acids, flavonoids and condensed tannins are the primary phenolic compounds that are present in legume seeds. Majority of the phenolic compounds are present in the legume seed coats. The seed coat of legume seeds primarily contains phenolic acids and flavonoids (mainly catechins and procyanidins). Gallic and protocatechuic acids are common in kidney bean and mung bean. Catechins and procyanidins represent almost 70% of total phenolic compounds in lentils and cranberry beans (seed coat). The antioxidant activity of phenolic compounds is in direct relation with their chemical structures such as number as well as position of the hydroxyl groups. Processing mostly leads to the reduction of phenolic compounds in legumes owing to chemical rearrangements. Phenolic content also decreases due to leaching of water-soluble phenolic compounds into the cooking water. The health benefits of phenolic compounds include acting as anticarcinogenic, anti-thrombotic, anti-ulcer, anti-artherogenic, anti-allergenic, anti-inflammatory, antioxidant, immunemodulating, anti-microbial, cardioprotective and analgesic agents. This review provides comprehensive information of phenolic compounds identified in grain legume seeds along with discussing their antioxidant and health promoting activities. Copyright © 2017 Elsevier Ltd. All rights reserved.

Lag phase and biomass determination of Rhodococcus pyridinivorans GM3 for degradation of phenol

NASA Astrophysics Data System (ADS)

Al-Defiery, M. E. J.; Reddy, G.

2018-05-01

Among various techniques available for removal of phenol, biodegradation is an eco-friendly and cost effective method. Thus, it is required to understand the process of biodegradation of phenol, such as investigate on lag phase and biomass concentration. Phenol degrading bacteria were isolated from soil samples of industrial sites in enriched mineral salts medium (MSM) with phenol as a sole source of energy and carbon. One isolate of potential phenol degradation from consortium for phenol degrading studies was identified as Rhodococcus pyridinivorans GM3. Lag phase and biomass determination of R. pyridinivorans GM3 was studied with different phenol concentrations under pH 8.5 at temperature 32 Co and 200 rpm. Microbial biomass was directly proportional to increasing phenol concentration between 1.0 to 2.0 g/L with a maximum dry biomass of 1.745 g/L was noted after complete degradation of 2.0 g/L phenol in 48 hours.

Removal of reactive red-120 and 4-(2-pyridylazo) resorcinol from aqueous samples by Fe3O4 magnetic nanoparticles using ionic liquid as modifier.

PubMed

Absalan, Ghodratollah; Asadi, Mozaffar; Kamran, Sedigheh; Sheikhian, Leila; Goltz, Douglas M

2011-08-30

The nanoparticles of Fe(3)O(4) as well as the binary nanoparticles of ionic liquid and Fe(3)O(4) (IL-Fe(3)O(4)) were synthesized for removal of reactive red 120 (RR-120) and 4-(2-pyridylazo) resorcinol (PAR) as model azo dyes from aqueous solutions. The mean size and the surface morphology of the nanoparticles were characterized by TEM, DLS, XRD, FTIR and TGA techniques. Adsorption of RR-120 and PAR was studied in a batch reactor at different experimental conditions such as nanoparticle dosage, dye concentration, pH of the solution, ionic strength, and contact time. Experimental results indicated that the IL-Fe(3)O(4) nanoparticles had removed more than 98% of both dyes under the optimum operational conditions of a dosage of 60mg, a pH of 2.5, and a contact time of 2min when initial dyes concentrations of 10-200mg L(-1) were used. The maximum adsorption capacity of IL-Fe(3)O(4) was 166.67 and 49.26mg g(-1) for RR-120 and PAR, respectively. The isotherm experiments revealed that the Langmuir model attained better fits to the equilibrium data than the Freundlich model. The Langmuir adsorption constants were 5.99 and 3.62L mg(-1) for adsorptions of RR-120 and PAR, respectively. Both adsorption processes were endothermic and dyes could be desorbed from IL-Fe(3)O(4) by using a mixed NaCl-acetone solution and adsorbent was reusable. Copyright © 2011 Elsevier B.V. All rights reserved.

Alkylresorcinol synthases expressed in Sorghum bicolor root hairs play an essential role in the biosynthesis of the allelopathic benzoquinone sorgoleone.

PubMed

Cook, Daniel; Rimando, Agnes M; Clemente, Thomas E; Schröder, Joachim; Dayan, Franck E; Nanayakkara, N P Dhammika; Pan, Zhiqiang; Noonan, Brice P; Fishbein, Mark; Abe, Ikuro; Duke, Stephen O; Baerson, Scott R

2010-03-01

Sorghum bicolor is considered to be an allelopathic crop species, producing phytotoxins such as the lipid benzoquinone sorgoleone, which likely accounts for many of the allelopathic properties of Sorghum spp. Current evidence suggests that sorgoleone biosynthesis occurs exclusively in root hair cells and involves the production of an alkylresorcinolic intermediate (5-[(Z,Z)-8',11',14'-pentadecatrienyl]resorcinol) derived from an unusual 16:3Delta(9,12,15) fatty acyl-CoA starter unit. This led to the suggestion of the involvement of one or more alkylresorcinol synthases (ARSs), type III polyketide synthases (PKSs) that produce 5-alkylresorcinols using medium to long-chain fatty acyl-CoA starter units via iterative condensations with malonyl-CoA. In an effort to characterize the enzymes responsible for the biosynthesis of the pentadecyl resorcinol intermediate, a previously described expressed sequence tag database prepared from isolated S. bicolor (genotype BTx623) root hairs was first mined for all PKS-like sequences. Quantitative real-time RT-PCR analyses revealed that three of these sequences were preferentially expressed in root hairs, two of which (designated ARS1 and ARS2) were found to encode ARS enzymes capable of accepting a variety of fatty acyl-CoA starter units in recombinant enzyme studies. Furthermore, RNA interference experiments directed against ARS1 and ARS2 resulted in the generation of multiple independent transformant events exhibiting dramatically reduced sorgoleone levels. Thus, both ARS1 and ARS2 are likely to participate in the biosynthesis of sorgoleone in planta. The sequences of ARS1 and ARS2 were also used to identify several rice (Oryza sativa) genes encoding ARSs, which are likely involved in the production of defense-related alkylresorcinols.

Oral bioavailability enhancement of β-lapachone, a poorly soluble fast crystallizer, by cocrystal, amorphous solid dispersion, and crystalline solid dispersion.

PubMed

Liu, Chengyu; Liu, Zhengsheng; Chen, Yuejie; Chen, Zhen; Chen, Huijun; Pui, Yipshu; Qian, Feng

2018-03-01

The aim of this paper was to compare the in vitro dissolution and in vivo bioavailability of three solubility enhancement technologies for β-lapachone (LPC), a poorly water soluble compound with extremely high crystallization propensity. LPC cocrystal was prepared by co-grinding LPC with resorcinol. LPC crystalline and amorphous solid dispersions (CSD and ASD) were obtained by spray drying with Poloxamer 188 and HPMC-AS, respectively. The cocrystal structure was solved by single crystal x-ray diffraction. All formulations were characterized by WAXRD, DSC, POM and SEM. USP II and intrinsic dissolution studies were used to compare the in vitro dissolution of these formulations, and a crossover dog pharmacokinetic study was used to compare their in vivo bioavailability. An 1:1 LPC-resorcinol cocrystal with higher solubility and faster dissolution rate was obtained, yet it converted to LPC crystal rapidly in solution. LPC/HPMC-AS ASD was confirmed to be amorphous and uniform, while the crystal and crystallite sizes of LPC in CSD were found to be ∼1-3 μm and around 40 nm, respectively. These formulations performed similarly during USP II dissolution, while demonstrated dramatically different oral bioavailability of ∼32%, ∼5%, and ∼1% in dogs, for CSD, co-crystal, and ASD, respectively. CSD showed the fastest intrinsic dissolution rate among the three. The three formulations showed poor IVIVC which could be due to rapid and unpredictable crystallization kinetics. Considering all the reasons, we conclude that for molecules with extremely high crystallization tendency that cannot be inhibited by any pharmaceutical excipients, size-reduction technologies such as CSD could be advantageous for oral bioavailability enhancement in vivo than technologies only generating transient but not sustained supersaturation. Copyright © 2018 Elsevier B.V. All rights reserved.

Enhancement of Fenton and photo-Fenton processes at initial circumneutral pH for the degradation of the β-blocker metoprolol.

PubMed

Romero, V; Acevedo, S; Marco, P; Giménez, J; Esplugas, S

2016-01-01

The need for acidification in the Fenton and photo-Fenton process is often outlined as one of its major drawbacks, thus in this work the acidification of the Metoprolol (MET) is avoided by the addition of resorcinol (RES), which is used to simulate model organic matter. The experiments were carried out at natural pH (6.2) with different Fe(2+) (1, 2.5, 5, and 10 mg/L) and H2O2 (25, 50, 125 and 150 mg/L) concentrations. The performance of MET and RES degradation was assessed along the reaction time. Working with the highest concentrations (5 and 10 mg/L of ferrous iron and 125 and 150 mg/L of H2O2) more than 90% of MET and RES removals were reached within 50 and 20 min of treatment, respectively, by Fenton process. However a low mineralization was achieved in both cases, likely, due to by-products accumulation. Regarding to photo-Fenton process, within 3 min with the highest iron and hydrogen peroxide concentrations, a complete MET degradation was obtained and 95% of RES conversion was achieved. Parameters such Total Organic Carbon, Chemical Oxygen Demand, and AOS were measured. Intermediates were identified and MET degradation path was proposed in the presence of resorcinol. Finally, a comparison between Fenton and photo-Fenton processes at acid pH and at initial circumneutral pH was discussed. The positive effect of RES on Fenton and photo-Fenton systems has been confirmed, allowing the work at circumneutral pH. Copyright © 2015 Elsevier Ltd. All rights reserved.

Role of 2-hexyl, 5-propyl resorcinol production by Pseudomonas chlororaphis PCL1606 in the multitrophic interactions in the avocado rhizosphere during the biocontrol process.

PubMed

Calderón, Claudia E; de Vicente, Antonio; Cazorla, Francisco M

2014-07-01

Different bacterial traits can contribute to the biocontrol of soilborne phytopathogenic fungus. Among others, (1) antagonism, (2) competition for nutrients and niches, (3) induction of systemic resistance of the plants and (4) predation and parasitism are the most studied. Pseudomonas chlororaphis PCL1606 is an antagonistic rhizobacterium that produces the antifungal metabolite 2-hexyl, 5-propyl resorcinol (HPR). This bacterium can biologically control the avocado white root rot caused by Rosellinia necatrix. Confocal laser scanning microscopy of the avocado rhizosphere revealed that this biocontrol bacterium and the fungal pathogen compete for the same niche and presumably also for root exudate nutrients. The use of derivative mutants in the geners related to HPR biosynthesis (dar genes) revealed that the lack of HPR production by P. chlororaphis PCL1606 negatively influences the bacterial colonisation of the avocado root surface. Microscopical analysis showed that P. chlororaphis PCL1606 closely interacts and colonises the fungal hyphae, which may represent a novel biocontrol mechanism in this pseudomonad. Additionally, the presence of HPR-producing biocontrol bacteria negatively affects the ability of the fungi to infect the avocado root. HPR production negatively affects hyphal growth, leading to alterations in the R. necatrix physiology visible under microscopy, including the curling, vacuolisation and branching of hyphae, which presumably affects the colonisation and infection abilities of the fungus. This study provides the first report of multitrophic interactions in the avocado rhizosphere, advancing our understanding of the role of HPR production in those interactions. © 2014 Federation of European Microbiological Societies. Published by John Wiley & Sons Ltd. All rights reserved.

Alkylresorcinol Synthases Expressed in Sorghum bicolor Root Hairs Play an Essential Role in the Biosynthesis of the Allelopathic Benzoquinone Sorgoleone[W][OA

PubMed Central

Cook, Daniel; Rimando, Agnes M.; Clemente, Thomas E.; Schröder, Joachim; Dayan, Franck E.; Nanayakkara, N.P. Dhammika; Pan, Zhiqiang; Noonan, Brice P.; Fishbein, Mark; Abe, Ikuro; Duke, Stephen O.; Baerson, Scott R.

2010-01-01

Sorghum bicolor is considered to be an allelopathic crop species, producing phytotoxins such as the lipid benzoquinone sorgoleone, which likely accounts for many of the allelopathic properties of Sorghum spp. Current evidence suggests that sorgoleone biosynthesis occurs exclusively in root hair cells and involves the production of an alkylresorcinolic intermediate (5-[(Z,Z)-8′,11′,14′-pentadecatrienyl]resorcinol) derived from an unusual 16:3Δ9,12,15 fatty acyl-CoA starter unit. This led to the suggestion of the involvement of one or more alkylresorcinol synthases (ARSs), type III polyketide synthases (PKSs) that produce 5-alkylresorcinols using medium to long-chain fatty acyl-CoA starter units via iterative condensations with malonyl-CoA. In an effort to characterize the enzymes responsible for the biosynthesis of the pentadecyl resorcinol intermediate, a previously described expressed sequence tag database prepared from isolated S. bicolor (genotype BTx623) root hairs was first mined for all PKS-like sequences. Quantitative real-time RT-PCR analyses revealed that three of these sequences were preferentially expressed in root hairs, two of which (designated ARS1 and ARS2) were found to encode ARS enzymes capable of accepting a variety of fatty acyl-CoA starter units in recombinant enzyme studies. Furthermore, RNA interference experiments directed against ARS1 and ARS2 resulted in the generation of multiple independent transformant events exhibiting dramatically reduced sorgoleone levels. Thus, both ARS1 and ARS2 are likely to participate in the biosynthesis of sorgoleone in planta. The sequences of ARS1 and ARS2 were also used to identify several rice (Oryza sativa) genes encoding ARSs, which are likely involved in the production of defense-related alkylresorcinols. PMID:20348430

Influence of iodine on the treatment of spacecraft humidity condensate to produce potable water

NASA Technical Reports Server (NTRS)

Symons, James M.; Muckle, Susan V.

1990-01-01

Several compounds in the ersatz humidity condensate do react with iodine to form iodine-substituted organic compounds (TOI), most notably phenol, acetaldehyde, ethanol, and sodium formate. Iodination of the ersatz humidity condensate produced 3.0 to 3.5 mg/L of TOI within 24 hours. The TOI that was produced by the passage of the ersatz humidity condensate through the first iodinated resin (IR) in the adsorption system was removed by the granular activated carbon that followed. TOI detected in the final effluent was formed by the reaction of the non-adsorbable condensate compounds with the final IR in the treatment series. The activated carbon bed series in the adsorption system performed poorly in its removal of TOC. The rapid breakthrough of TOC was not surprising, as the ersatz humidity condensate contained several highly soluble organic compounds, alcohols and organic acids.

A novel porous framework as variable chemo-sensor: from response of specific carcinogenic alkyl-aromatic to selective detection of explosive nitro-aromatics.

PubMed

Chen, Qihui

2018-06-07

Selective probing one molecule from one class similar molecules is highly challenging due to their similar chemical and physical properties. Here, a novel metal-organic framework FJI-H15 with flexible porous cages has been designed and synthesized, which can specifically recognize ethyl-benzene with ultrahigh enhancement efficiency from series of alkyl-aromatics, in which an unusual size-dependent interaction has been found and proved. While it also can selectively detect phenolic-nitroaromatics among series of nitro-aromatics based on energy transferring and electrostatic interaction. Such unusual specificity and variable mechanisms responding to different type molecules has not been reported, which will provide a new strategy for developing more effective chemo-sensor based on MOFs for probing small structural differences in molecules. © 2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Solid/liquid extraction equilibria of phenolic compounds with trioctylphosphine oxide impregnated in polymeric membranes.

PubMed

Praveen, Prashant; Loh, Kai-Chee

2016-06-01

Trioctylphosphine oxide based extractant impregnated membranes (EIM) were used for extraction of phenol and its methyl, hydroxyl and chloride substituted derivatives. The distribution coefficients of the phenols varied from 2 to 234, in the order of 1-napthol > p-chlorophenol > m-cresol > p-cresol > o-cresol > phenol > catechol > pyrogallol > hydroquinone, when initial phenols loadings was varied in 100-2000 mg/L. An extraction model, based on the law of mass action, was formulated to predict the equilibrium distribution of the phenols. The model was in excellent agreement (R(2) > 0.97) with the experimental results at low phenols concentrations (<800 mg/L). At higher phenols loadings though, Langmuir isotherm was better suited for equilibrium prediction (R(2) > 0.95), which signified high mass transfer resistance in the EIMs. Examination of the effects of ring substitution on equilibrium, and bivariate statistical analysis between the amounts of phenols extracted into the EIMs and factors affecting phenols interaction with TOPO, indicated the dominant role of hydrophobicity in equilibrium determination. These results improve understanding of the solid/liquid equilibrium process between phenols and the EIMs, and these will be useful in designing phenol recovery process from wastewater. Copyright © 2016 Elsevier Ltd. All rights reserved.

The Profile and Bioaccessibility of Phenolic Compounds in Cereals Influenced by Improved Extrusion Cooking Treatment

PubMed Central

Zeng, Zicong; Liu, Chengmei; Luo, Shunjing; Chen, Jun; Gong, Ersheng

2016-01-01

The aim of this study was to investigate the effect of Improved Extrusion Cooking Treatment (IECT) on the phenolics and its bioaccessibility in cereals, represented by brown rice, wheat, and oat. Data showed that total phenolic content and total antioxidant activity in free form were significantly decreased, while the bound form was increased after IECT. After IECT, the total free phenolic acids of brown rice and wheat were significantly decreased by 5.88% and 45.66%, respectively, while the total bound phenolic acids of brown rice, wheat, and oat were significantly increased by 6.45%, 8.78%, and 9.10%, respectively. Brown rice provided the most bioaccessible phenolics and antioxidant compounds, followed by oat and wheat. IECT significantly decreased the bioaccessible phenolics of brown rice and oat by 31.09% and 30.95%, while it had minimal effect on the bioaccessible phenolics of wheat. These results showed that IECT greatly affected the phenolics and its bioaccessibiltiy of cereals, with the effect depending on cereal matrix and the sensitivity of free and bound phenolics. Furthermore, bioaccessible phenolic acids of raw and processed cereals were considerably low, and it slightly contributed to the bioaccessible phenolics. PMID:27513581

Surface characterization of lignocellulosics for composite manufacture

NASA Astrophysics Data System (ADS)

Iyer, Ananth V.

The objectives of this research were to form moisture resistant wheat strawboards, either by altering the straw surface characteristics or by changing the chemistry of the polymeric 4, 4' diphenylmethane diisocyanate (PMDI)-based matrix and interface. Part I compared the surface characteristics of wheat, barley, oat, rice, kenaf, hemp and softwood particles. All cereal straws had two surfaces: epidermis and brittle-pith unlike one heterogeneous type observed for bast fibers and softwood particles. The epidermis of cereal straws was not wet by water or aqueous binders, whereas the pith surface allowed the penetration of water, but was not readily wetted by aqueous binders. Between the different surface treatments evaluated for wheat straw in Part II, NaOH selectively peeled-off the epidermis and pith layers. The treated straw particles were formable into strawboards using aqueous phenol-formaldehyde, urea-formaldehyde, and duroplastic acrylic acid binders with good internal bond strength (IBS) and adequate water resistance. In Part III it was shown that, decreasing straw particle sizes and bleaching worsened the mechanical properties of strawboards, but the moisture absorption properties of bleached strawboards were lower than the unbleached ones. Layering of straw particles in strawboards did not seem to affect their mechanical or moisture absorption properties. Part IV showed that the pith surface of wheat straw was fractured on curing with PMDI, providing hollow microcrevices for water accumulation. Furthermore, the cured PMDI formed a network polyurea/polyuretonimine/polycarbodiimide/polyisocyanurate polymer on straw surfaces whose properties dictated the properties of strawboards. Among the different mono-, bi-, and tri-functional alcohols, amines and carboxylic acids evaluated in Part V as H-donor substitutes to moisture for reaction with PMDI on straw surfaces, ethylene glycol, resorcinol, glycerin and citric acid provided IBS values greater than the ANSI recommended minimum (60 psi) and lower thickness swell values than the moisture-cure process. In Part VI, strawboards formed with 2% PMDI and 5% epoxy or duroplastic acrylic acid binders had high IBS values, and their thickness swell after 24 h soaking in water was restricted to 13%, which was much lower than the ˜18--20% values obtained for strawboards made with 5% PMDI.

Development of new efficient method for isolation of phenolics from sea algae prior to their rapid resolution liquid chromatographic-tandem mass spectrometric determination.

PubMed

Klejdus, Bořivoj; Plaza, Merichel; Šnóblová, Marie; Lojková, Lea

2017-02-20

The extraction of phenolic compounds from 4 different sea algae samples, three brown algae (Cystoseira abies-marina, C. abies-marina grinded under cryogenic conditions with liquid nitrogen, Undaria pinnatifida and Sargassum muticum) and one red algae (Chondrus crispus) via solid phase extraction using micro-elution solid-phase extraction (μ-SPE) plate method was studied. Prior to μ-SPE, 50mg of algae with 80% methanol mixture was extracted in hyphenated series by various extraction techniques, such as pressurized liquid extraction and Ika Ultra-Turrax ® Tube Drive, in combination with ultrasound assisted extraction. The μ-SPE plate technique reduced the time of sample pre-treatment thanks to higher sensitivity and pre-concentration effect. Selected groups of benzoic acid derivatives (p-hydroxybenzoic, protocatechuic, gallic, vanillic, and syringic acids), hydroxybenzaldehydes (4-hydroxybenzaldehyde, and 3,4-dihydroxybenzaldehyde), and cinnamic acid derivatives (p-coumaric, caffeic, ferulic, sinapic, and chlorogenic acids) were determined using rapid resolution liquid chromatography coupled to mass spectrometry detection with negative ion electrospray ionization (RRLC-ESI-MS) using multiple reactions monitoring. LOQs of measured samples varied in the range 0.23-1.68ng/mL and LODs in the range 0.07-0.52ng/mL. The applied method allowed a simultaneous determination of phenolics (i.e. free, esters soluble in methanol, glycosides, and esters insoluble in methanol) in less than 5min (including alkaline or acidic hydrolysis of raw extracts) from sea algae extracts. Copyright © 2016 Elsevier B.V. All rights reserved.

Resolving the chemical structures of off-odorants and potentially harmful substances in toys-example of children's swords.

PubMed

Denk, Philipp; Velasco-Schön, Cristina; Buettner, Andrea

2017-09-01

Most children's toys on the market are primarily made out of plastic and other complex composite materials. Consumer complaints about offensive odors or irritating effects associated with toy products have increased in recent years. One example is the strongly perceivable negative odor reported for a particular series of toy swords. Characterizing the presence of contaminants, including those that have the potential to be deleterious to health, in such products is a significant analytical challenge due to the high baseline abundance of chemical constituents of the materials used in the products. In the present study, the nature of offensive odorants associated with toy sword products was examined by gas chromatography (GC). After initial sensory evaluations, the volatile compounds from the toy products were recovered using solvent extraction and solvent-assisted flavor evaporation. The extracts were analyzed using GC-olfactometry (GC-O) and two-dimensional GC-O coupled with mass spectrometry (GC-GC-MS/O). A total of 26 odor-active compounds, including aromatic hydrocarbons and phenols, were identified among numerous non-odorous volatile by-products. These substances also included polycyclic aromatic hydrocarbons, which were analyzed by GC-MS. Representative substances were naphthalene and 1,2-dihydronaphthalene that exhibited moldy, mothball-like odor impressions, and phenol derivatives with leather-like, phenolic, horse-stable-like smells. The odorants detected correlated with the assigned attributes from the sensory analyses. This study clearly shows that the detection and identification of such odorous contaminants can provide key indications of potentially harmful yet unknown substances in everyday products such as toys. Graphical abstract ᅟ.

VUV/UV light inducing accelerated phenol degradation with a low electric input.

PubMed

Li, Mengkai; Wen, Dong; Qiang, Zhimin; Kiwi, John

2017-01-23

This study presents the first evidence for the accelerated degradation of phenol by Fenton's reagent in a mini-fluidic VUV/UV photoreaction system (MVPS). A low-pressure mercury lamp used in the MVPS led to a complete degradation of phenol within 4-6 min. The HO˙ and HO 2 ˙ originating from both Fenton's reagent and VUV photolysis of water were identified with suitable radical scavengers. The effects of initial concentrations of phenol, H 2 O 2 and Fe 3+ as well as solution pH on phenol degradation kinetics were examined. Increasing the initial phenol concentration slowed down the phenol degradation, whereas increasing the initial H 2 O 2 or Fe 3+ concentration accelerated the phenol degradation. The optimal solution pH was 3.7. At both 254 and 185 nm, increasing phenol concentration enhanced its absorption for the incident photons. The reaction mechanism for the degradation of phenol was suggested consistent with the results obtained. This study indicates that the VUV/UV photo-Fenton process has potential applications in the treatment of industrial wastewater containing phenol and related aromatic pollutants.

Phenolic profile and in vitro antioxidant capacity of insoluble dietary fiber powders from citrus (Citrus junos Sieb. ex Tanaka) pomace as affected by ultrafine grinding.

PubMed

Tao, Bingbing; Ye, Fayin; Li, Hang; Hu, Qiang; Xue, Shan; Zhao, Guohua

2014-07-23

The effects of mechanical and jet grindings on the proximate composition, phenolics, and antioxidant capacity of insoluble antioxidant dietary fiber powder from citrus pomace (IADFP-CP) were investigated in comparison with ordinary grinding. IADFP-CP from jet grinding showed higher levels of crude fat, total sugar, and free phenolics and lower levels of crude protein and bound phenolics than that from ordinary grinding. Totally, 14 phenolics (9 free, 1 bound, and 4 free/bound) in IADFP-CP were identified by RP-HPLC-DAD/ESI-Q-TOF-MS/MS. Hesperidin accounted for >57% of total phenolics in IADFP-CP. Among IADFP-CPs, the jet-ground presented the highest free phenolics but the lowest bound phenolics. The IADFP-CP from jet grinding presented the highest antioxidant capacity of free phenolics (by DPPH and FRAP assays), followed by the ones from mechanical and then ordinary grinding. The present study suggests that jet grinding could improve the extraction of phenolic compounds from IADFP-CP and increase the antioxidant capacities of free phenolics and the resultant powder.

Cocarcinogenicity of phenols from Estonian shale tars (oils).

PubMed Central

Bogovski, P A; Mirme, H I

1979-01-01

Many phenols have carcinogenic activity. The Estonian shale oils contain up to 40 vol % phenols. The promoting activity after initiation of phenols of Estonian shale oils was tested in mice with a single subthreshold dose (0.36 mg) of benzo(a)pyrene. C57Bl and CC57Br mice were used in skin painting experiments. Weak carcinogenic activity was found in the total crude water-soluble phenols recovered from the wastewater of a shale processing plant. In two-stage experiments a clear promoting action of the total crude phenols was established, whereas the fractions A and B (training reagents), obtained by selective crystallization of the total phenols exerted a considerably weaker promoting action. Epo-glue, a commercial epoxy product produced from unfractionated crude phenols, had no promoting activity, which may be due to the processing of the phenols involving polymerization. The mechanism of action of phenols is not clear. According to some data from the literature, phenol and 5-methylresorcinol reduce the resorption speed of BP in mouse skin, causing prolongation of the action fo the carcinogen. PMID:446449

Cocarcinogenicity of phenols from Estonian shale tars (oils).

PubMed

Bogovski, P A; Mirme, H I

1979-06-01

Many phenols have carcinogenic activity. The Estonian shale oils contain up to 40 vol % phenols. The promoting activity after initiation of phenols of Estonian shale oils was tested in mice with a single subthreshold dose (0.36 mg) of benzo(a)pyrene. C57Bl and CC57Br mice were used in skin painting experiments. Weak carcinogenic activity was found in the total crude water-soluble phenols recovered from the wastewater of a shale processing plant. In two-stage experiments a clear promoting action of the total crude phenols was established, whereas the fractions A and B (training reagents), obtained by selective crystallization of the total phenols exerted a considerably weaker promoting action. Epo-glue, a commercial epoxy product produced from unfractionated crude phenols, had no promoting activity, which may be due to the processing of the phenols involving polymerization. The mechanism of action of phenols is not clear. According to some data from the literature, phenol and 5-methylresorcinol reduce the resorption speed of BP in mouse skin, causing prolongation of the action fo the carcinogen.

The regulation by phenolic compounds of soil organic matter dynamics under a changing environment.

PubMed

Min, Kyungjin; Freeman, Chris; Kang, Hojeong; Choi, Sung-Uk

2015-01-01

Phenolics are the most abundant plant metabolites and are believed to decompose slowly in soils compared to other soil organic matter (SOM). Thus, they have often been considered as a slow carbon (C) pool in soil dynamics models. Here, however, we review changes in our concept about the turnover rate of phenolics and quantification of different types of phenolics in soils. Also, we synthesize current research on the degradation of phenolics and their regulatory effects on decomposition. Environmental changes, such as elevated CO2, warming, nitrogen (N) deposition, and drought, could influence the production and form of phenolics, leading to a change in SOM dynamics, and thus we also review the fate of phenolics under environmental disturbances. Finally, we propose the use of phenolics as a tool to control rates of SOM decomposition to stabilize organic carbon in ecosystems. Further studies to clarify the role of phenolics in SOM dynamics should include improving quantification methods, elucidating the relationship between phenolics and soil microorganisms, and determining the interactive effects of combinations of environmental changes on the phenolics production and degradation and subsequent impact on SOM processing.

Chemopreventive effects of free and bound phenolics associated to steep waters (nejayote) obtained after nixtamalization of different maize types.

PubMed

Rojas-García, Carlos; García-Lara, Silverio; Serna-Saldivar, Sergio O; Gutiérrez-Uribe, Janet A

2012-03-01

Free and bound phenolics extracts from nejayote solids were obtained after optimally lime-cooking blue, normal white, red, normal yellow, high-carotenoid and quality protein maize types. The extraction yield ranged from 4.47 to 10.05%. Bound phenolics extracts had higher content of total phenolics, antioxidant activity and ferulic acid compared to the free phenolics extracts. In general, free phenolics extracts were less cytotoxic than the bound phenolics counterparts. Bound phenolics extracts had higher induction of quinone reductase (QR) and particularly the normal yellow nejayote exerted the highest chemopreventive index tested in Hepa1c1c7 cells. When tested for monofunctional phase 2 induction capacity in BPrc1 cells, the bound phenolics extracts of blue, normal white and quality protein nejayotes were better inducers than the normal yellow counterpart. Particularly, the free phenolics extract of the white maize nejayote induced BPrc1 cells QR and exerted a higher chemopreventive index compared to the bound phenolics extract. Therefore, the nejayote of the normal white maize was the best source of monofunctional phase 2 enzyme inducers.

Phenol separation from phenol-laden saline wastewater by membrane aromatic recovery system-like membrane contactor using superhydrophobic/organophilic electrospun PDMS/PMMA membrane.

PubMed

Ren, Long-Fei; Adeel, Mister; Li, Jun; Xu, Cong; Xu, Zheng; Zhang, Xiaofan; Shao, Jiahui; He, Yiliang

2018-05-15

Phenol recovery from phenol-laden saline wastewater plays an important role in the waste reclamation and pollution control. A membrane aromatic recovery system-like membrane contactor (MARS-like membrane contactor) was set up in this study using electrospun polydimethylsiloxane/polymethyl methacrylate (PDMS/PMMA) membrane with 0.0048 m 2 effective area to separate phenol from saline wastewater. Phenol and water contact angles of 0° and 162° were achieved on this membrane surface simultaneously, indicating its potential in the separation of phenol and water-soluble salt. Feed solution (500 mL) of 0.90 L/h and receiving solution (500 mL) of 1.26 L/h were investigated to be the optimum conditions for phenol separation, which corresponds to the employed Reynolds number of 14.6 and 20.5. During 108-h continuous separation for feed solution (2.0 g/L phenol, 10.0 g/L NaCl) under room temperature (20 °C), 42.6% of phenol was recycled in receiving solution with a salt rejection of 99.95%. Meanwhile, the mean phenol mass transfer coefficient (K ov ) was 6.7 × 10 -7  m s -1 . As a membrane-based process, though the permeated phenol increased with the increase of phenol concentration in feed solution, the phenol recovery ratio was determined by the membrane properties rather than the pollutant concentrations. Phenol was found to permeate this membrane via adsorption, diffusion and desorption, and therefore, the membrane fouling generated from pore blockage in other membrane separation processes was totally avoided. Copyright © 2018 Elsevier Ltd. All rights reserved.

Sustainable biodegradation of phenol by immobilized Bacillus sp. SAS19 with porous carbonaceous gels as carriers.

PubMed

Ke, Qian; Zhang, Yunge; Wu, Xilin; Su, Xiaomei; Wang, Yuyang; Lin, Hongjun; Mei, Rongwu; Zhang, Yu; Hashmi, Muhammad Zaffar; Chen, Chongjun; Chen, Jianrong

2018-09-15

In this study, high-efficient phenol-degrading bacterium Bacillus sp. SAS19 which was isolated from activated sludge by resuscitation-promoting factor (Rpf) addition, were immobilized on porous carbonaceous gels (CGs) for phenol degradation. The phenol-degrading capabilities of free and immobilized Bacillus sp. SAS19 were evaluated under various initial phenol concentrations. The obtained results showed that phenol could be removed effectively by both free and immobilized Bacillus sp. SAS19. Furthermore, for degradation of phenol at high concentrations, long-term utilization and recycling were more readily achieved for immobilized bacteria as compared to free bacteria. Immobilized bacteria exhibited significant increase in phenol-degrading capabilities in the third cycle of recycling and reuse, which demonstrated 87.2% and 100% of phenol (1600 mg/L) degradation efficiency at 12 and 24 h, respectively. The present study revealed that immobilized Bacillus sp. SAS19 can be potentially used for enhanced treatment of synthetic phenol-laden wastewater. Copyright © 2018 Elsevier Ltd. All rights reserved.

A comprehensive evaluation of three microfluidic chemiluminescence methods for the determination of the total phenolic contents in fruit juices.

PubMed

Al Haddabi, Buthaina; Al Lawati, Haider A J; Suliman, FakhrEldin O

2017-01-01

Three recently reported microfluidic chemiluminescence (MF-CL) methods (based on reactions with acidic permanganate enhanced by formaldehyde (KMnO4-COH), acidic cerium (IV) and rhodamine B (Ce-RB), and acidic cerium (IV) and rhodamine 6G (Ce-R6G) enhanced by SDS) for the determination of the total phenolic content (TPC) in juices were critically evaluated in terms of their selectivity. The evaluation was carried out using 86 analytes, including 22 phenolic compounds (phenolic acids and polyphenols), 6 known non-phenolic antioxidants, 9 amino acids and a number of proteins, carbohydrates, nucleotide bases, inorganic salts and other compounds. Each method was sensitive toward phenolic compounds (PCs). However, the KMnO4-COH CL system showed a higher sensitivity toward phenolic acids and also responded to non-phenolic antioxidants. The other two systems showed higher sensitivity toward polyphenolic compounds than to phenolic acids and did not responded to all other compounds including non-phenolic antioxidants. Copyright © 2016 Elsevier Ltd. All rights reserved.

Bound Phenolics of Quinoa Seeds Released by Acid, Alkaline, and Enzymatic Treatments and Their Antioxidant and α-Glucosidase and Pancreatic Lipase Inhibitory Effects.

PubMed

Tang, Yao; Zhang, Bing; Li, Xihong; Chen, Peter X; Zhang, Hua; Liu, Ronghua; Tsao, Rong

2016-03-02

Unextractable phenolics from plant foods and their role in health benefits have become increasingly important. Meal residues of three quinoa seeds free of fat and extractable phenolics were subjected to acid, alkaline, and enzymatic hydrolyses. The total and individual phenolic compounds released were analyzed, and 19 phenolics, predominantly phenolic acids and several flavonoids, were identified. The concentration of bound phenolics was highest in black quinoa followed by red and white, regardless of the hydrolysis method. Higher phenolic contents also showed stronger antioxidant activities and inhibition of α-glucosidase and pancreatic lipase activities. Carbohydrases, that is, pectinase, xylanase and feruloyl esterase, which effectively liberated bound phenolics are known to be secreted by colonic bacteria, suggesting potential antioxidant and anti-inflammatory effects by these compounds in the large intestine during colonic fermentation. These results can also be applied to treat foods high in bound phenolics to enhance bioaccessibility.

Electrochemical removal of phenol from oil refinery wastewater.

PubMed

Abdelwahab, O; Amin, N K; El-Ashtoukhy, E-S Z

2009-04-30

This study explores the possibility of using electrocoagulation to remove phenol from oil refinery waste effluent using a cell with horizontally oriented aluminum cathode and a horizontal aluminum screen anode. The removal of phenol was investigated in terms of various parameters namely: pH, operating time, current density, initial phenol concentration and addition of NaCl. Removal of phenol during electrocoagulation was due to combined effect of sweep coagulation and adsorption. The results showed that, at high current density and solution pH 7, remarkable removal of 97% of phenol after 2h can be achieved. The rate of electrocoagulation was observed to increase as the phenol concentration decreases; the maximum removal rate was attained at 30 mg L(-1) phenol concentration. For a given current density using an array of closely packed Al screens as anode was found to be more effective than single screen anode, the percentage phenol removal was found to increase with increasing the number of screens per array. After 2h of electrocoagulation, 94.5% of initial phenol concentration was removed from the petroleum refinery wastewater. Energy consumption and aluminum Electrode consumption were calculated per gram of phenol removed. The present study shows that, electrocoagulation of phenol using aluminum electrodes is a promising process.

Compositional dynamics of dissolved lignin in watersheds: small temperate streams to large tropical rivers

NASA Astrophysics Data System (ADS)

Ward, N. D.; Keil, R. G.; Medeiros, P. M.; Brito, D.; Krusche, A. V.; Richey, J. E.

2012-12-01

The most abundant biochemicals on land are cellulose, hemicellulose, and lignin. Lignin, alone, composes roughly 30% of the organic carbon (OC) in the terrestrial biosphere (Boerjan et al., 2003) and a significant portion of the OC mobilized into stream and river networks worldwide. Here we present a synthesis of several studies examining (i) the mobilization dynamics/compositional changes in dissolved lignin during rapid storm events in small temperate streams (Hood Canal, WA, USA), and (ii) the respiration dynamics/biological overturning of dissolved (and particulate) lignin in the Amazon River mainstem. Rapid sampling (3 hour intervals) during short-term rainfall events has revealed that the concentration of dissolved lignin phenols (as well as DOC) in small temperate streams is strongly correlated with river discharge (Ward et al., 2012). Additionally, rapid discharge increases resulted in an increase in Ad/Al and C/V ratios and decrease in the S/V ratio of dissolved lignin phenols, indicating a mobilization of relatively degraded non-woody/gymnosperm-derived material in the dissolved phase during storms occurring after a long dry period. We hypothesize that sorption to soil surfaces imparts an additional control on lignin mobilization: degraded phenols are relatively more soluble than their non-degraded counterparts and are easily mobilized by rapid flow, whereas non-degraded phenols are slowly mobilized by base flow and continuously degraded in soils. Once lignin is mobilized into the aquatic setting it is often assumed to be refractory. However, evidence in the Amazon River mainstem suggests the contrary. We have assessed the biodegradability of dissolved (and particulate) lignin, as well as a vast suite (~120) of similar phenolic compounds with a series of incubation experiments performed on four Amazon River cruises. We estimate that on average the degradation of lignin and similar phenolic compounds supports 30-50% of bulk respiration rates in the river, implying that lignin may be a highly important organic matter fuel for CO2 outgassing from the world's inland waters. Contrary to bulk respiration rates, which poorly correlate with bulk OC concentrations, the respiration of lignin appears to be almost entirely controlled by substrate composition. Lignin (and OC) concentrations and lignin degradation rates both correlate well with the seasonal hydrograph in the Amazon (Ward et al., submitted). Based on the measurements made here, and by others (Hedges et al., 1988; Field et al., 1998; Houghton et al., 2001; Malhi et al., 2008; Bose et al., 2009) we estimate that roughly 80 Tg C of lignin is sequestered in Amazonian soils annually, roughly 40% of this lignin is respired in soils, 55% is respired within the river continuum, and less than 5% is delivered to the ocean.

Lethal and sublethal effects of chlorine, phenol, and chlorine-phenol mixtures on the mud crab, Panopeus herbstii.

PubMed

Key, P B; Scott, G I

1986-11-01

The mud crab, Panopeus herbstii, was acutely exposed (96-hr) to chlorine-produced oxidants (CPO), phenol, and a CPO-phenolic mixture (1:1) to determine lethal and sublethal effects. The 96-hr (LC50) values were determined for each individual compound and mixture. Additionally, whole-animal respiration rates were measured following acute exposure to sublethal concentrations of each compound or mixture. Phenol uptake/depuration rates were measured in the phenol and CPO-phenol mixture concentrations. Results indicated 96-hr LC50 values of 1.06 mg/L for CPO (fiducial limits (FL) = 0.53-2.01 mg/L), 52.8 mg/L for phenol (FL = 45.6-64.5 mg/L), and 184.7 mg/L total toxicant units (TTU) for the CPO-phenol mixture (FL = 143.7-250.2 mg/L TTU). Statistical analysis indicated that the acute toxicity of the CPO-phenol mixture was less than additive. Sublethal studies indicated that only acute exposure to sublethal concentrations of CPO caused altered respiration rates. After 96-hr depuration, metabolic rates in all CPO-exposure crabs generally returned to control rates. Uptake/depuration rate studies indicated significantly lower phenol uptake rates in crabs exposed to the CPO-phenol mixture. These findings suggest that the less-than-additive toxicity of the CPO-phenol mixture may result from lowered uptake/depuration rate kinetics and indicate that the discharge of chlorinated-phenolic waste may not result in additive and/or synergistic interactions, but rather in less-than-additive effects on decapod aquatic species.

Inhibition of the acetoclastic methanogenic activity by phenol and alkyl phenols.

PubMed

Olguin-Lora, P; Puig-Grajales, L; Razo-Flores, E

2003-08-01

Chemical and petrochemical industries are important sources of aromatic pollutants. Petrochemical processes like caustic washing of middle distillates produce the spent caustic liquors highly concentrated in phenol and alkyl phenols. The anaerobic technology is considered a feasible strategy for petrochemical wastewater pre-treatment although high concentrations of phenol could limit its efficiency. The goal of this work was to determine the toxicity of both selected alkyl phenols and a synthetic "spent-caustic phenols mixture" on the acetoclastic Specific Methanogenic Activity (SMA) of unadapted and phenol-adapted granular sludge. Alkyl phenols were responsible for 50% (IC50) and 100% (IC100) inhibition of the SMA at concentrations ranging from 1.6 to 5.0 mM and from 4.1 to 27.5 mM, respectively, for un-adapted granular sludge. In the case of phenol-adapted granular sludge, the inhibitory concentrations ranged from 1.7 to 14.9 mM and from 4.0 to 83.0 for IC50 and IC100, respectively, highlighting the impact of sludge acclimation. The inhibition produced by 2-ethylphenol was more acute compared to phenol and was not reduced by the phenol acclimation process. The IC50 and IC100 values obtained for the synthetic "spent-caustic phenols mixture" were 9.5 mM and 88.4 mM, respectively. The inhibitory concentrations of phenol compounds were closely correlated with compound apolarity (log P), indicating that the lipophilic character of the tested compounds was responsible for their methanogenic toxicity. An inhibition model is confirmed to estimate the IC50 and IC100.

Determination of Radical Scavenging Activity and Total Phenols of Wine and Spices: A Randomized Study

PubMed Central

Lugemwa, Fulgentius Nelson; Snyder, Amanda L.; Shaikh, Koonj

2013-01-01

Thirty eight bottles of red wine (Carbanet Sauvignon) were randomly selected based on vintage, region, price, and age (number of months in a barrel). The total phenolic content of each wine was determined using Folin-Ciocalteau assay. The radical scavenging activity was evaluated using 2,2-diphenyl-1-picryhydrazyl (DPPH) assay. Apart from a few bottles that exhibited above average radical scavenging activity and phenolic content, there was no good correlation of those two quantities with region, price or vintage. The average phenolic amount was 2874 mg/L. The lowest phenolic content was found to be 1648 mg/L for an eight dollar wine. Wine with the highest amount of phenol of 4495 mg/L was a 2007, nine dollar bottle from South America. High amount of phenols did not translate into high radical scavenging activity. Barrel-aging did not increase the amount of phenols or the radical scavenging activity of wine. In order to discover new and potent sources of antioxidants from plants, the following spices were studied: ginger, cilantro, cumin, anise, linden, eucalyptus, marjoram, oregano, sage, thyme and rosemary. Whole spices were crushed and extracted for 96 h at room temperature using a combination of ethyl acetate, ethyl alcohol and water in the ratio of 4.5:4.5:1 (v/v/v). The radical scavenging activity of extracts was evaluated using 2,2-diphenyl-1-picryhydrazyl (DPPH) assay. The total phenolic content of each spice was also determined using the Folin-Ciocalteau assay. Eucalyptus was found to be the most potent antioxidant with an LC50 of 324.1 mg of phenol/L, followed by marjoram with an LC50 of 407.5 mg of phenol/L, and rosemary with an LC50 of 414.0 mg/L. The least potent antioxidants were ginger and cilantro with LC50 of 7604 mg/L of phenol and 7876 mg of phenol/L, respectively. PMID:26784340

Influence of Protein-Phenolic Complex on the Antioxidant Capacity of Flaxseed (Linum usitatissimum L.) Products.

PubMed

Guimarães Drummond E Silva, Fernanda; Miralles, Beatriz; Hernández-Ledesma, Blanca; Amigo, Lourdes; Iglesias, Amadeu Hoshi; Reyes Reyes, Felix Guillermo; Netto, Flavia Maria

2017-02-01

The impact of the naturally present phenolic compounds and/or proteins on the antioxidant capacity of flaxseed products (phenolic fraction, protein concentrates, and hydrolysates) before and after simulated gastrointestinal digestion was studied. For that, whole and phenolic reduced products were assessed. Four glycosylated phenolic compounds (secoisolariciresinol and ferulic, p-coumaric, and caffeic acids) were identified in flaxseed products. Phenolic fraction exerts the highest antioxidant capacity that increased by alkaline hydrolysis and by simulated gastrointestinal digestion. The action of Alcalase and digestive enzymes resulted in an increase of the antioxidant capacity of whole and phenolic reduced products. Principal component analysis showed that proteinaceous samples act as antioxidant is by H + transfer, while those samples containing phenolic compounds exert their effects by both electron donation and H + transfer mechanisms. Protein/peptide-phenolic complexation, confirmed by fluorescence spectra, exerted a positive effect on the antioxidant capacity, mainly in protein concentrates.

Determination of niobium in rocks by an isotope dilution spectrophotometric method

USGS Publications Warehouse

Greenland, L.P.; Campbell, E.Y.

1970-01-01

Rocks and minerals are fused with sodium peroxide in the presence of carrierfree 95Nb. The fusion cake is leached with water and the precipitate dissolved in hydrofluoric-sulfuric acid mixture. Niobium is extracted into methyl isobutyl ketone and further purified by ion exchange. The amount of niobium is determined spectrophotometrically with 4-(2-pyridylazo)-resorcinol, and the chemical yield of the separations determined by counting 95Nb. This procedure is faster and less sensitive to interferences than previously proposed methods for determining niobium in rocks.The high purity of the separated niobium makes the method applicable to nearly all matrices. ?? 1970.

Separation of V(V)-4-(2-pyridylazo)resorcinolato complex from a large excess reagent using an ODS cartridge for high-performance liquid chromatography.

PubMed

Takahashi, Toru; Kaneko, Emiko; Yotsuyanagi, Takao

2006-12-01

A selective off-line preconcentration technique for the V(V) complex with 4-(2-pyridylazo)resorcinol has been developed and successfully applied to the determination of V(V) in an air-borne sample. The target complex was separated from excess reagent using an ODS cartridge and water as the eluent. The complex was then concentrated on another ODS cartridge using tetrabutylammonium bromide and eluted with methanol; the eluate was applied to a one-drop concentration/HPLC. A detection limit as low as (6.05 +/- 0.82)x 10(-11) M (5 ppt) was achieved.

In situ Silver Spot Preparation and on-Plate Surface-Enhanced Raman Scattering Detection in Thin Layer Chromatography Separation

NASA Astrophysics Data System (ADS)

Herman, K.; Mircescu, N. E.; Szabo, L.; Leopold, L. F.; Chiş, V.; Leopold, N.

2013-05-01

An improved approach for surface-enhanced Raman scattering (SERS) detection of mixture constituents after thin layer chromatography (TLC) separation is presented. A SERS active silver substrate was prepared under open air conditions, directly on the thin silica film by photo-reduction of silver nitrate, allowing the detection of binary mixtures of cresyl violet, bixine, crystal violet, and Cu(II) complex of 4-(2-pyridylazo)resorcinol. The recorded SERS spectrum provides a unique spectral fingerprint for each molecule; therefore the use of analyte standards is avoided, thus rendering the presented procedure advantageous compared to the conventional detection methodology in TLC.

Effect of in-situ bonding system and surface modification of montmorillonite on the properties of butyl rubber/MMT composites

NASA Astrophysics Data System (ADS)

Halim, S. F.; Lawandy, S. N.; Nour, M. A.

2012-07-01

Isobutylene-isoprene rubber (IIR)/nanoclay composites were prepared by solution intercalation method. Cloisite Na+ nanoclays and organo-modified montmorillonite (OMT) Cloisite 10 A,.15 A and 20 A were used in this study. The effect of In-situ bonding system HRH (hexametylene tetramine: resorcinol: hydrated silica) on the dispersion of used nanoclays in the rubber matrix were examined by X-ray diffraction and atomic force microscopy (AFM). Characterization of the prepared composites was performed by studying the rheometeric and mechanical properties. The burning out behavior of the nanocomposites with and without the bonding system was also measured.

Distribution and potential ecological risk of 50 phenolic compounds in three rivers in Tianjin, China.

PubMed

Zhong, Wenjue; Wang, Donghong; Wang, Zijian

2018-04-01

Phenolic compounds widely exist in the surface water of many countries; however, few studies have simultaneously analyzed and evaluated broad-spectrum phenolic compounds in various components of the water environment. Therefore this study analyzed the distribution and potential ecological risk of 50 phenolic compounds in the surface water, sediment and suspended particulate matter of three important rivers in Tianjin, the main heavy industry city with high pollution in China. The qualitative results show that phenolic pollution existed extensively in the three rivers and the kinds of phenolic compounds in the water were relatively higher than in both sediment and suspended particulate matter. The quantitative results show that the phenolic pollution in the wet-season samples was serious than dry-season samples. Meanwhile, total concentrations of phenolic compounds in three components from the Dagu Drainage River (DDR) were all much higher than those in the Beitang Drainage River (BDR) and Yongdingxin River (YDXR). The highest total concentrations of phenolic compounds in three components all appeared in wet-season samples in DDR, and the highest total concentration was 1354 μg/L in surface water, 719 μg/kg dw in suspended particulate matter and 2937 μg/kg dw in sediment, respectively. The ecological risk of phenolic compounds in surface water was evaluated using the quotient method, and phenolic compounds with risk quotient (RQ) > 1 (RQ > 0.3 for YDXR) were identified as priority pollutants. Five kinds of phenolic compounds were identified as priority phenolic compounds in BDR, and the order of risk was 2-cresol > 2,4-xylenol > 2-sec-butylphenol > 2-naphthol > 3-cresol. Six kinds of phenolic compounds were identified as priority phenolic compounds in DDR, and the order of risk was 2-naphthol > p-chloro-m-xylenol > 4-cresol > 3-cresol > 2,4-xylenol > 2,3,6-Trimethylphenol. In YDXR, only phenol, 2-naphthol and 2,4-xylenol were identified as priority phenolic compounds. Copyright © 2017 Elsevier Ltd. All rights reserved.

Elucidation of riverine and lacustrine dissolved organic matter (DOM) composition using comprehensive GC×GC time-of-flight mass spectrometry (GC×GC-TOF-MS)

NASA Astrophysics Data System (ADS)

Ball, G. I.; Goldberg, S. J.; Aluwihare, L. I.

2012-12-01

Rivers and streams play a key role in mediating the transfer of organic carbon (both particulate and dissolved) from terrestrial to aquatic settings. Dissolved organic carbon represents the majority of the carbon pool in low alkalinity riverine and lacustrine waters, and its composition plays important roles, including affecting water clarity and stimulating heterotrophic productivity, which influences its rate of reconversion to CO2. Yet, the chemical complexity and heterogeneity of this reservoir have limited structural elucidation to primarily describing common bulk-level characteristics. Seasonal SPE-DOM samples from the Upper Truckee River, Lake Tahoe, and two surrounding lakes, as well as SPE-DOM isolated from two dissimilar California rivers, were first characterized using δ13C, δ15N, 1H-NMR, and then subjected to CuO oxidation followed by TMS derivatization and were analyzed using comprehensive GC×GC time-of-flight mass spectrometry (GC×GC-TOF-MS). Thousands of peaks were identified per sample. Simultaneous, orthogonal separation of components in two dimensions (on the basis of volatility and polarity) allowed for the identification of oxidation mixture components by both their MS spectra and, when MS spectra alone were insufficient for structural assignment and standards were absent, by the observed trajectories of homologues compound series assumed in 2-D retention-time space. Several homologous compound series were observed, including mid-to-long chain fatty acids, keto (ω-1) fatty acids, (α, ω)-dioic acids, and the resolution and identification of closely related isomers, such as the benzene di-, and tricarboxylic acids, were also facilitated by this method. Furthermore, in mixed samples containing two or more end-members, such as in lake DOM samples characterized by mixed terrestrial and algal OM sources, the intensity of the phenolic elution space, which includes the lignin phenols and lignin phenolic dimers, correlates with ancillary measurements indicative of terrestrial OM loading, such as increased 1H-NMR resonance intensities for methoxy and aromatic-linked hydrogens and lower δ13C values more consistent with C3 plant versus algal sources.igure 1: Oxidized and derivatized SPE-DOM isolated from the Upper Truckee River, South Lake Tahoe, CA, and visualized in two dimensions.

Inhibitory potentials of phenolic-rich extracts from Bridelia ferruginea on two key carbohydrate-metabolizing enzymes and Fe2+-induced pancreatic oxidative stress.

PubMed

Afolabi, Olakunle Bamikole; Oloyede, Omotade Ibidun; Agunbiade, Shadrack Oludare

2018-05-01

The current study was designed to evaluate the various antioxidant potentials and inhibitory effects of phenolic-rich leaf extracts of Bridelia ferruginea (BF) on the in vitro activities of some key enzymes involved in the metabolism of carbohydrates. In this study, BF leaf free and bound phenolic-rich extracts were used. We quantified total phenolic and flavonoid contents, and evaluated several antioxidant activities using assays for ferric reducing antioxidant power, total antioxidant activity (phosphomolybdenum reducing ability), 1,1-diphenyl-2-picrylhydrazyl and thiobarbituric acid reactive species. Also, extracts were tested for their ability to inhibit α-amylase and α-glucosidase activity. The total phenolic and total flavonoid contents in the free phenolic extract of BF were significantly greater than in the bound phenolic extract. Also, all the antioxidant activities considered were significantly greater in the free phenolic extract than in the bound phenolic extract. In the same vein, the free phenolic-rich extract had a significantly higher percentage inhibition against α-glucosidase activity (IC 50  = 28.5 µg/mL) than the bound phenolic extract (IC 50  = 340.0 µg/mL). On the contrary, the free phenolic extract (IC 50  = 210.0 µg/mL) had significantly lower inhibition against α-amylase than the bound phenolic-rich extract (IC 50  = 190.0 µg/mL). The phenolic-rich extracts of BF leaves showed antioxidant potentials and inhibited two key carbohydrate-metabolizing enzymes in vitro. Copyright © 2018 Shanghai Changhai Hospital. Published by Elsevier B.V. All rights reserved.

Isolation and characterization of phenol degrading bacterium strain Bacillus thuringiensis J20 from olive waste in Palestine.

PubMed

Ereqat, Suheir I; Abdelkader, Ahmad A; Nasereddin, Abedelmajeed F; Al-Jawabreh, Amer O; Zaid, Taher M; Letnik, Ilya; Abdeen, Ziad A

2018-01-02

This study aimed at isolation of phenol degrading bacteria from olive mill wastes in Palestine. The efficiency of phenol removal and factors affecting phenol degradation were investigated. A bacterial strain (J20) was isolated from solid olive mill waste and identified as Bacillus thuringiensis based on standard morphological, biochemical characteristics and 16SrRNA sequence analysis. The strain was able to grow in a phenol concentration of 700 mg/L as the sole carbon and energy source. The culture conditions showed a significant impact on the ability of these cells to remove phenol. This strain exhibited optimum phenol degradation performance at pH 6.57 and 30 °C . Under the optimized conditions, this strain could degrade 88.6% of phenol (700 mg/L) within 96 h when the initial cell density was OD 600 0.2. However, the degradation efficiency could be improved from about 88% to nearly 99% by increasing the cell density. Immobilization of J20 was carried out using 4% sodium alginate. Phenol degradation efficiency of the immobilized cells of J20 was higher than that of the free cells, 100% versus 88.6% of 700 mg/L of phenol in 120 h, indicating the improved tolerance of the immobilized cells toward phenol toxicity. The J20 was used in detoxifying crude OMWW, phenolic compounds levels were reduced by 61% compared to untreated OMWW after five days of treatment. Hence, B. thuringiensis-J20 can be effectively used for bioremediation of phenol-contaminated sites in Palestine. These findings may lead to new biotechnological applications for the degradation of phenol, related to olive oil production.

Biodegradation of phenol in synthetic and industrial wastewater by Rhodococcus erythropolis UPV-1 immobilized in an air-stirred reactor with clarifier.

PubMed

Prieto, M B; Hidalgo, A; Rodríguez-Fernández, C; Serra, J L; Llama, M J

2002-05-01

Phenol biodegradation by suspended and immobilized cells of Rhodococcus erythropolis UPV-1 was studied in discontinuous and continuous mode under optimum culture conditions. Phenol-acclimated cells were adsorbed on diatomaceous earth, where they grew actively forming a biofilm of short filaments. Immobilization protected cells against phenol and resulted in a remarkable enhancement of their respiratory activity and a shorter lag phase preceding active phenol degradation. Under optimum operation conditions in a laboratory-scale air-stirred reactor, the immobilized cells were able to completely degrade phenol in synthetic wastewater at a volumetric productivity of 11.5 kg phenol m(-3) day(-1). Phenol biodegradation was also tested in two different industrial wastewaters (WW1 and WW2) obtained from local resin manufacturing companies, which contained both phenols and formaldehyde. In this case, after wastewater conditioning (i.e., dilution, pH, nitrogen and phosphorous sources and micronutrient amendments) the immobilized cells were able to completely remove the formaldehyde present in both waters. Moreover, they biodegraded phenols completely at a rate of 0.5 kg phenol m(-3) day(-1) in the case of WW1 and partially (but at concentrations lower than 50 mg l(-1)) at 0.1 and 1.0 kg phenol m(-3) day(-1) in the cases of WW2 and WW1, respectively.

Synthesis and characterization of a series of nickel( ii ) alkoxide precursors and their utility for Ni(0) nanoparticle production

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

Treadwell, LaRico J.; Boyle, Timothy J.; Phelan, W. Adam

2017-02-22

We synthesized a series of nickel(II) aryloxide ([Ni(OAr) 2(py) x]) precursors from an amide-alcohol exchange using [Ni(NR 2) 2] in the presence of pyridine (py). The H-OAr selected were the mono- and di-ortho-substituted 2-alkyl phenols: alkyl = methyl (H-oMP), iso-propyl (H-oPP), tert-butyl (H-oBP) and 2,6-di-alkyl phenols (alkyl = di-iso-propyl (H-DIP), di-tert-butyl (H-DBP), di-phenyl (H-DPhP)). Furthermore, the crystalline products were solved as solvated monomers and structurally characterized as [Ni(OAr) 2(py) x], where x = 4: OAr = oMP (1), oPP (2); x = 3: OAr = oBP (3), DIP (4); x = 2: OAr = DBP (5), DPhP (6). The excitedmore » states (singlet or triplet) and various geometries of 1–6 were identified by experimental UV-vis and verified by computational modeling. Magnetic susceptibility of the representative compound 4 was fit to a Curie Weiss model that yielded a magnetic moment of 4.38(3)μ B consistent with a Ni 2+ center. Compounds 1 and 6 were selected for decomposition studied under solution precipitation routes since they represent the two extremes of coordination. The particle size and crystalline structure were characterized using transmission electron microscopy (TEM) and powder X-ray diffraction (PXRD). Finally, the materials isolated from 1 and 6 were found by TEM to form irregular shape nanomaterials (8–15 nm), which by PXRD were found to be Ni 0 hcp (PDF: 01-089-7129) and fcc (PDF: 01-070-0989), respectively.« less

Directional liquefaction of biomass for phenolic compounds and in situ hydrodeoxygenation upgrading of phenolics using bifunctional catalysts

Treesearch

Junfeng Feng; Chung-yun Hse; Kui Wang; Zhongzhi Yang; Jianchun Jiang; Junming Xu

2017-01-01

Phenolic compounds derived from biomass are important feedstocks for the sustainable production of hydrocarbon biofuels. Hydrodeoxygenation is an effective process to remove oxygen-containing functionalities in phenolic compounds. This paper reported a simple method for producing hydrocarbons by liquefying biomass and upgrading liquefied products. Three phenolic...

Selective defunctionalization by TiO2 of monomeric phenolics from lignin pyrolysis into simple phenols.

PubMed

Mante, Ofei D; Rodriguez, Jose A; Babu, Suresh P

2013-11-01

This study is focused on defunctionalizing monomeric phenolics from lignin into simple phenols for applications such as phenol/formaldehyde resins, epoxidized novolacs, adhesives and binders. Towards this goal, Titanium dioxide (TiO2) was used to selectively remove hydroxyl, methoxy, carbonyl and carboxyl functionalities from the monomeric phenolic compounds from lignin to produce mainly phenol, cresols and xylenols. The results showed that anatase TiO2 was more selective and active compared to rutile TiO2. Catechols were found to be the most reactive phenolics and 4-ethylguaiacol the least reactive with anatase TiO2. An overall conversion of about 87% of the phenolics was achieved at 550°C with a catalyst-to-feed ratio of 5 w/w. Over 97% conversion of phenolics is achievable at moderate temperatures (550°C or ≤ 600°C) and a moderate catalyst-to-feed ratio of 6.5:1. The reactivity of catechols on TiO2 suggests that titania is a promising catalyst in the removal of hydroxyl moiety. Published by Elsevier Ltd.

Transition of phenolics and cyanogenic glycosides from apricot and cherry fruit kernels into liqueur.

PubMed

Senica, Mateja; Stampar, Franci; Veberic, Robert; Mikulic-Petkovsek, Maja

2016-07-15

Popular liqueurs made from apricot/cherry pits were evaluated in terms of their phenolic composition and occurrence of cyanogenic glycosides (CGG). Analyses consisted of detailed phenolic and cyanogenic profiles of cherry and apricot seeds as well as beverages prepared from crushed kernels. Phenolic groups and cyanogenic glycosides were analyzed with the aid of high-performance liquid chromatography (HPLC) and mass spectrophotometry (MS). Lower levels of cyanogenic glycosides and phenolics have been quantified in liqueurs compared to fruit kernels. During fruit pits steeping in the alcohol, the phenolics/cyanogenic glycosides ratio increased and at the end of beverage manufacturing process higher levels of total analyzed phenolics were detected compared to cyanogenic glycosides (apricot liqueur: 38.79 μg CGG per ml and 50.57 μg phenolics per ml; cherry liqueur 16.08 μg CGG per ml and 27.73 μg phenolics per ml). Although higher levels of phenolics are characteristic for liqueurs made from apricot and cherry pits these beverages nevertheless contain considerable amounts of cyanogenic glycosides. Copyright © 2016 Elsevier Ltd. All rights reserved.

Potentiometric study of binary complexes of 3-[(1 R)-1-hydroxy-2-(methylamino)ethyl]phenol hydrochloride with some lanthanide ions in aqueous and mixed solutions

NASA Astrophysics Data System (ADS)

Sharma, S. S.; Kadia, M. V.

2014-12-01

The complexation of lanthanide ions (Y3+, La3+, Ce3+, Pr3+, Nd3+, Sm3+, Gd3+, Tb3+, and Dy3+) with 3-[(1 R)-1-hydroxy-2-(methylamino)ethyl]phenol hydrochloride was studied at different temperatures and different ionic strengths in aqueous solutions by Irving-Rossotti pH titration technique. Stepwise calculation, PKAS and BEST Fortran IV computer programs were used for determination of proton-ligand and metal-ligand stability constants. The formation of species like MA, MA2, and MA(OH) is considered in SPEPLOT. Thermodynamic parameters of complex formation (Δ G, Δ H, and Δ S) are also evaluated. Negative Δ G and Δ H values indicate that complex formation is favourable in these experimental conditions. The stability of complexes is also studied at in different solvent-aqueous (vol/vol). The stability series of lanthanide complexes has shown to have the "gadolinium break." Stability of complexes decreases with increase in ionic strength and temperature. Effect of systematic errors like effect of dissolved carbon dioxide, concentration of alkali, concentration of acid, concentration of ligand and concentration of metal have also been explained.

Chemoselective amide formation using O-(4-nitrophenyl)hydroxylamines and pyruvic acid derivatives.

PubMed

Kumar, Sonali; Sharma, Rashi; Garcia, Megan; Kamel, Joseph; McCarthy, Caroline; Muth, Aaron; Phanstiel, Otto

2012-12-07

A series of O-(4-nitrophenyl)hydroxylamines were synthesized from their respective oximes using a pulsed addition of excess NaBH(3)CN at pH 3 in 65-75% yield. Steric hindrance near the oxime functional group played a key role in both the ease by which the oxime could be reduced and the subsequent reactivity of the respective hydroxylamine. Reaction of the respective hydroxylamines with pyruvic acid derivatives generated the desired amides in good yields. A comparison of phenethylamine systems bearing different leaving groups revealed significant differences in the rates of these systems and suggested that the leaving group ability of the N-OR substituent plays an important role in determining their reactivity with pyruvic acid. Competition experiments (in 68% DMSO/phosphate buffered saline) using 1 equiv of N-phenethyl-O-(4-nitrophenyl)hydroxylamine and 2 equiv of pyruvic acid in the presence of other nucleophiles such as glycine, cysteine, phenol, hexanoic acid, and lysine demonstrated that significant chemoselectivity is present in this reaction. The results suggest that this chemoselective reaction can occur in the presence of excess α-amino acids, phenols, acids, thiols, and amines.

Discovery of a new class of histone deacetylase inhibitors with a novel zinc binding group.

PubMed

Li, Youxuan; Woster, Patrick M

2015-04-01

Small molecules featuring a hydroxamic acid or a benzamide zinc binding group (ZBG) are the most thoroughly studied histone deacetylase (HDAC) inhibitors. However, concerns about the pharmacokinetic liabilities of the hydroxamic acid moiety and potential metabolic toxicity of the aniline portion of benzamide HDAC inhibitors have stimulated research efforts aimed at discovering alternative ZBGs. Here we report the 2-(oxazol-2-yl)phenol moiety as a novel ZBG that can be used to produce compounds that are potent HDAC inhibitors. A series of analogues with this novel ZBG have been synthesized, and these analogues exhibit selective inhibition against HDAC1 as well as the class IIb HDACs (HDAC6 and HDAC10). Compound 10 possesses an IC 50 value of 7.5 μM in the MV-4-11 leukemia cell line, and induces a comparable amount of acetylated histone 3 lysine 9 (H3K9) and p21Waf1/CIP1 as 0.5 μM of SAHA. Modeling of compound 10 in the active site of HDAC2 demonstrates that the 2-(oxazol-2-yl)phenol moiety has a zinc-binding pattern similar to benzamide HDAC inhibitors.

Carbonic anhydrase inhibitors: in vitro inhibition of α isoforms (hCA I, hCA II, bCA III, hCA IV) by flavonoids.

PubMed

Ekinci, Derya; Karagoz, Lutfi; Ekinci, Deniz; Senturk, Murat; Supuran, Claudiu T

2013-04-01

A series of flavonoids, such as quercetin, catechin, apigenin, luteolin, morin, were investigated for their inhibitory effects against the metalloenzyme carbonic anhydrase (CA). The compounds were tested against four α-CA isozymes purified from human and bovine (hCA I, hCA II, bCA III, hCA IV) tissues. The four isozymes showed quite diverse inhibition profiles with these compounds. The flavonoids inhibited hCA I with K(I)-s in the range of 2.2-12.8 μM, hCA II with K(I)-s in the range of 0.74-6.2 μM, bCA III with K(I)-s in the range of 2.2-21.3 μM, and hCA IV with inhibition constants in the range of 4.4-15.7, with an esterase assay using 4-nitrophenyl acetate as substrate. Some simple phenols/sulfonamides were also investigated as standard inhibitors. The flavonoids incorporate phenol moieties which inhibit these CAs through a diverse, not yet determined inhibition mechanism, compared to classic inhibitors such as the sulfonamide/sulfamate ones.

Soybean phenolic-rich extracts inhibit key-enzymes linked to type 2 diabetes (α-amylase and α-glucosidase) and hypertension (angiotensin I converting enzyme) in vitro.

PubMed

Ademiluyi, Adedayo O; Oboh, Ganiyu

2013-03-01

This study sought to assess the inhibitory activities of phenolic-rich extracts from soybean on α-amylase, α-glucosidase and angiotensin I converting enzyme (ACE) activities in vitro. The free phenolic extract of the soybean was obtained by extraction with 80% acetone, while that of the bound phenolic extract was done by extracting the alkaline and acid hydrolyzed residue with ethyl acetate. The inhibitory action of these extracts on the enzymes activity as well as their antioxidant properties was assessed. Both phenolic-rich extracts inhibited α-amylase, α-glucosidase and ACE enzyme activities in a dose dependent pattern. However, the bound phenolic extract exhibited significantly (P < 0.05) higher α-amylase and ACE inhibition while the free phenolic extract had significantly (P < 0.05) higher α-glucosidase inhibitory activity. Nevertheless, the free phenolic extract had higher α-glucosidase inhibitory activity when compared to that of α-amylase; this property confer an advantage on soybean phenolic-rich extracts over commercial antidiabetic drugs with little or no side effect. And inhibition of ACE suggests the antihypertension potential of soybean phenolic-rich extracts. Furthermore, the enzyme inhibitory activities of the phenolic-rich extracts were not associated with their phenolic content. Therefore, phenolic-rich extracts of soybean could inhibit key-enzyme linked to type 2 diabetes (α-amylase and α-glucosidase) and hypertension (ACE) and thus could explain in part the mechanism by which soybean renders these health promoting effect. Copyright © 2011 Elsevier GmbH. All rights reserved.

Accumulation of Phenolic Compounds and Expression Profiles of Phenolic Acid Biosynthesis-Related Genes in Developing Grains of White, Purple, and Red Wheat.

PubMed

Ma, Dongyun; Li, Yaoguang; Zhang, Jian; Wang, Chenyang; Qin, Haixia; Ding, Huina; Xie, Yingxin; Guo, Tiancai

2016-01-01

Polyphenols in whole grain wheat have potential health benefits, but little is known about the expression patterns of phenolic acid biosynthesis genes and the accumulation of phenolic acid compounds in different-colored wheat grains. We found that purple wheat varieties had the highest total phenolic content (TPC) and antioxidant activity. Among phenolic acid compounds, bound ferulic acid, vanillic, and caffeic acid levels were significantly higher in purple wheat than in white and red wheat, while total soluble phenolic acid, soluble ferulic acid, and vanillic acid levels were significantly higher in purple and red wheat than in white wheat. Ferulic acid and syringic acid levels peaked at 14 days after anthesis (DAA), whereas p-coumaric acid and caffeic acid levels peaked at 7 DAA, and vanillic acid levels gradually increased during grain filling and peaked near ripeness (35 DAA). Nine phenolic acid biosynthesis pathway genes (TaPAL1, TaPAL2, TaC3H1, TaC3H2, TaC4H, Ta4CL1, Ta4CL2, TaCOMT1, and TaCOMT2) exhibited three distinct expression patterns during grain filling, which may be related to the different phenolic acids levels. White wheat had higher phenolic acid contents and relatively high gene expression at the early stage, while purple wheat had the highest phenolic acid contents and gene expression levels at later stages. These results suggest that the expression of phenolic acid biosynthesis genes may be closely related to phenolic acids accumulation.

Accumulation of Phenolic Compounds and Expression Profiles of Phenolic Acid Biosynthesis-Related Genes in Developing Grains of White, Purple, and Red Wheat

PubMed Central

Ma, Dongyun; Li, Yaoguang; Zhang, Jian; Wang, Chenyang; Qin, Haixia; Ding, Huina; Xie, Yingxin; Guo, Tiancai

2016-01-01

Polyphenols in whole grain wheat have potential health benefits, but little is known about the expression patterns of phenolic acid biosynthesis genes and the accumulation of phenolic acid compounds in different-colored wheat grains. We found that purple wheat varieties had the highest total phenolic content (TPC) and antioxidant activity. Among phenolic acid compounds, bound ferulic acid, vanillic, and caffeic acid levels were significantly higher in purple wheat than in white and red wheat, while total soluble phenolic acid, soluble ferulic acid, and vanillic acid levels were significantly higher in purple and red wheat than in white wheat. Ferulic acid and syringic acid levels peaked at 14 days after anthesis (DAA), whereas p-coumaric acid and caffeic acid levels peaked at 7 DAA, and vanillic acid levels gradually increased during grain filling and peaked near ripeness (35 DAA). Nine phenolic acid biosynthesis pathway genes (TaPAL1, TaPAL2, TaC3H1, TaC3H2, TaC4H, Ta4CL1, Ta4CL2, TaCOMT1, and TaCOMT2) exhibited three distinct expression patterns during grain filling, which may be related to the different phenolic acids levels. White wheat had higher phenolic acid contents and relatively high gene expression at the early stage, while purple wheat had the highest phenolic acid contents and gene expression levels at later stages. These results suggest that the expression of phenolic acid biosynthesis genes may be closely related to phenolic acids accumulation. PMID:27148345

VUV/UV light inducing accelerated phenol degradation with a low electric input† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c6ra26043h Click here for additional data file.

PubMed Central

Li, Mengkai; Wen, Dong

2017-01-01

This study presents the first evidence for the accelerated degradation of phenol by Fenton's reagent in a mini-fluidic VUV/UV photoreaction system (MVPS). A low-pressure mercury lamp used in the MVPS led to a complete degradation of phenol within 4–6 min. The HO˙ and HO2˙ originating from both Fenton's reagent and VUV photolysis of water were identified with suitable radical scavengers. The effects of initial concentrations of phenol, H2O2 and Fe3+ as well as solution pH on phenol degradation kinetics were examined. Increasing the initial phenol concentration slowed down the phenol degradation, whereas increasing the initial H2O2 or Fe3+ concentration accelerated the phenol degradation. The optimal solution pH was 3.7. At both 254 and 185 nm, increasing phenol concentration enhanced its absorption for the incident photons. The reaction mechanism for the degradation of phenol was suggested consistent with the results obtained. This study indicates that the VUV/UV photo-Fenton process has potential applications in the treatment of industrial wastewater containing phenol and related aromatic pollutants. PMID:28496972

Changes of phenolic profiles and antioxidant activity in canaryseed (Phalaris canariensis L.) during germination.

PubMed

Chen, Zhijie; Yu, Lilei; Wang, Xinkun; Gu, Zhenxin; Beta, Trust

2016-03-01

Canaryseed is an important cereal crop in western Canada. The changes of the total phenolic content (TPC), antioxidant activities, phenolic acid profiles (free and bound) of canaryseed during germination were investigated in the present study. The growth properties also were investigated. Fresh weight, shoot length and root length increased, whereas dry mass of canaryseed decreased during germination. A 22.3% loss of dry matter was observed at 120h of germination. The total phenolic content and antioxidant activities of free and bound extracts showed a general trend of germinated seeds>raw seeds>soaked seeds. Free, bound and total phenolic content significantly increased 1042%, 120% and 741% at the end of germination as compared to raw seeds (p<0.05). DPPH, ABTS and ORAC assays were employed to evaluate the antioxidant activity of canaryseed. There were high correlations between total phenolic content and antioxidant activities. TPC and ORAC values showed the highest correlation (r=0.9984). Six phenolic acids in free phenolic extracts and seven phenolic acids in bound phenolic extracts were detected, respectively. Bound ferulic acid, the dominant phenolic acid in canaryseed, significantly increased during germination (p<0.05). Study showed that germination provided a new approach to further develop canaryseed as a functional food for human consumption. Copyright © 2015 Elsevier Ltd. All rights reserved.

Phenolic profiles and antioxidant activity of Turkish Tombul hazelnut samples (natural, roasted, and roasted hazelnut skin).

PubMed

Pelvan, Ebru; Olgun, Elmas Öktem; Karadağ, Ayşe; Alasalvar, Cesarettin

2018-04-01

The phenolic profiles and antioxidant status of hazelnut samples [natural (raw) hazelnut, roasted hazelnut, and roasted hazelnut skin] were compared. Free and bound (ester-linked and glycoside-linked) phenolic acids were examined using liquid chromatography-tandem mass spectrometry (LC-MS/MS). Comprehensive identification of phenolics was carried out using Q-exactive hybrid quadrupole-orbitrap mass spectrometer (Q-OT-MS). Samples were also assessed for their total phenolics and antioxidant activities using three different assays. Ten free and bound phenolic acids were quantified in hazelnut samples. Roasted hazelnut skin contained the highest content of total phenolic acids, followed by natural and roasted hazelnuts. The majority of phenolic acids were present in the bound form. Using a Q-OT-MS, 22 compounds were tentatively identified, 16 of which were identified for the first time in hazelnut samples. The newly identified compounds consisted of flavonoids, phenolic acids and related compounds, hydrolysable tannins and related compounds, and other phenolics. Three antioxidant assays demonstrated similar trends that roasted hazelnut skin rendered the highest activity. The present work suggests that roasted hazelnut skin is a rich source of phenolics and can be considered as a value-added co-product for use as functional food ingredient and antioxidant. Copyright © 2017 Elsevier Ltd. All rights reserved.

Wine phenolics.

PubMed

Waterhouse, Andrew L

2002-05-01

Wine contains many phenolic substances, most of which originate in the grape berry. The phenolics have a number of important functions in wine, affecting the tastes of bitterness and astringency, especially in red wine. Second, the color of red wine is caused by phenolics. Third, the phenolics are the key wine preservative and the basis of long aging. Lastly, since phenolics oxidize readily, they are the component that suffers owing to oxidation and the substance that turns brown in wine (and other foods) when exposed to air. Wine phenolics include the non-flavonoids: hydroxycinnamates, hydroxybenzoates and the stilbenes; plus the flavonoids: flavan-3-ols, the flavonols, and the anthocyanins. While polymeric condensed tannins and pigmented tannins constitute the majority of wine phenolics, their large size precludes absorption and thus they are not likely to have many health effects (except, perhaps, in the gut). The total amount of phenols found in a glass of red wine is on the order of 200 mg versus about 40 mg in a glass of white wine.

Development and UFLC-MS/MS Characterization of a Product-Specific Standard for Phenolic Quantification of Maple-Derived Foods.

PubMed

Liu, Yongqiang; Ma, Hang; Seeram, Navindra P

2016-05-04

The phenolic contents of plant foods are commonly quantified by the Folin-Ciocalteu assay based on gallic acid equivalents (GAEs). However, this may lead to inaccuracies because gallic acid is not always representative of the structural heterogeneity of plant phenolics. Therefore, product-specific standards have been developed for the phenolic quantification of several foods. Currently, maple-derived foods (syrup, sugar, sap/water, and extracts) are quantified for phenolic contents based on GAEs. Because lignans are the predominant phenolics present in maple, herein, a maple phenolic lignan-enriched standard (MaPLES) was purified (by chromatography) and characterized (by UFLC-MS/MS with lignans previously isolated from maple syrup). Using MaPLES and secoisolariciresinol (a commercially available lignan), the phenolic contents of the maple-derived foods increased 3-fold compared to GAEs. Therefore, lignan-based standards are more appropriate for phenolic quantification of maple-derived foods versus GAEs. Also, MaPLES can be utilized for the authentication and detection of fake label claims on maple products.

An adsorption-release-biodegradation system for simultaneous biodegradation of phenol and ammonium in phenol-rich wastewater.

PubMed

Wang, Ying; Chen, Hu; Liu, Yu-Xiang; Ren, Rui-Peng; Lv, Yong-Kang

2016-07-01

The feasibility of simultaneous biodegradation of phenol and ammonium in phenol-rich wastewater was evaluated in a reusable system, which contained macroporous adsorption resin and Alcaligenes faecalis strain WY-01. In the system, up to 6000mg/L phenol could be completely degraded by WY-01; meanwhile, 99.03±3.95% of ammonium was removed from the initial concentration of 384mg/L. This is the first study to show the capability of single strain in simultaneous removal of ammonium and phenol in wastewater containing such high concentrations of phenol. Moreover, the resin was regenerated during the biodegradation process without any additional manipulations, indicating the system was reusable. Furthermore, enzyme assay, gene expression patterns, HPLC-MS and gas chromatography analysis confirmed that phenol biodegradation accompanied with aerobic nitrifier denitrification process. Results imply that the reusable system provides a novel strategy for more efficient biodegradation of phenol and ammonium contained in some particular industrial wastewater. Copyright © 2016 Elsevier Ltd. All rights reserved.

Effect of phenol on the mycelial growth and fructification in some of basidiomycetous fungi.

PubMed

Upadhyay, R C; Hofrichter, M

1993-01-01

Cometabolic growth studies with phenol were undertaken to screen 32 strains of white and brown rot fungi. All the cultures studied grew well up to 4 mM of phenol on Czapekdox agar except Agaricus bisporus (white button mushroom) and Pleurotus cystidiosus. Most of them could grow even up to 6 mM of phenol. Phenol induced a brown pigmentation of the culture medium. P. flabellatus and P. pulmonarius metabolized 67 and 64 mg/l phenol in 10 days. Studies have indicated that phenol (0.1 to 1.0 mM) incorporated in malt-extract agar has no inhibitory effect on fruitbody formation. Preliminary studies indicate that soaking of wheat straw with phenol solution up to 1600 mg/l give better mycelial growth and fructification of P. cornucopiae, P. ostreatus Z-15 and Calocybe indica than water soaked. Soaking of wheat straw in phenol inhibited the growth of common competitor weed fungi like Stachybotrys sp. and Coprinus sp.

Pulse seed germination improves antioxidative activity of phenolic compounds in stripped soybean oil-in-water emulsions.

PubMed

Xu, Minwei; Jin, Zhao; Peckrul, Allen; Chen, Bingcan

2018-06-01

The purpose of this study was to investigate antioxidative activity of phenolic compounds extracted from germinated pulse seed including chickpeas, lentils and yellow peas. Phenolic compounds were extracted at different germination time and total phenolic content was examined by Folin Ciocalteu's reaction. Antioxidative activity of extracts was characterized by in vitro assay including 2, 2-diphenyl-1-picrylhydrazyl radical scavenging capacity (DPPH), oxygen radical absorbance capacity (ORAC), iron-binding assay, and in stripped soybean oil-in-water emulsions. The results suggested that germination time is critical for phenolic compounds production. The form variation of phenolic compounds influenced the antioxidative activity of phenolic compounds both in vitro assay and in emulsion systems. Soluble bound phenolic compounds showed higher antioxidative ability in emulsion system with the order of chickpea > yellow pea > lentil. On the basis of these results, soluble bound phenolic compounds may be considered as a promising natural antioxidant to prevent lipid oxidation in foods. Copyright © 2018 Elsevier Ltd. All rights reserved.

Phenolic Polymer Solvation in Water and Ethylene Glycol, II: Ab Initio Computations.

PubMed

Bauschlicher, Charles W; Bucholz, Eric W; Haskins, Justin B; Monk, Joshua D; Lawson, John W

2017-04-06

Ab initio techniques are used to study the interaction of ethylene glycol and water with a phenolic polymer. The water bonds more strongly with the phenolic OH than with the ring. The phenolic OH groups can form hydrogen bonds between themselves. For more than one water molecule, there is a competition between water-water and water-phenolic interactions. Ethylene glycol shows the same effects as those of water, but the potential energy surface is further complicated by CH 2 -phenolic interactions, different conformers of ethylene glycol, and two OH groups on each molecule. Thus, the ethylene glycol-phenolic potential is more complicated than the water-phenolic potential. The results of the ab initio calculations are compared to those obtained using a force field. These calibration studies show that the water system is easier to describe than the ethylene glycol system. The calibration studies confirm the reliability of force fields used in our companion molecular dynamics study of a phenolic polymer in water and ethylene solutions.

Recycling of phenolic compounds in Borneo's tropical peat swamp forests.

PubMed

Yule, Catherine M; Lim, Yau Yan; Lim, Tse Yuen

2018-02-07

Tropical peat swamp forests (TPSF) are globally significant carbon stores, sequestering carbon mainly as phenolic polymers and phenolic compounds (particularly as lignin and its derivatives) in peat layers, in plants, and in the acidic blackwaters. Previous studies show that TPSF plants have particularly high levels of phenolic compounds which inhibit the decomposition of organic matter and thus promote peat accumulation. The studies of phenolic compounds are thus crucial to further understand how TPSF function with respect to carbon sequestration. Here we present a study of cycling of phenolic compounds in five forests in Borneo differing in flooding and acidity, leaching of phenolic compounds from senescent Macaranga pruinosa leaves, and absorption of phenolics by M. pruinosa seedlings. The results of the study show that total phenolic content (TPC) in soil and leaves of three species of Macaranga were highest in TPSF followed by freshwater swamp forest and flooded limestone forest, then dry land sites. Highest TPC values were associated with acidity (in TPSF) and waterlogging (in flooded forests). Moreover, phenolic compounds are rapidly leached from fallen senescent leaves, and could be reabsorbed by tree roots and converted into more complex phenolics within the leaves. Extreme conditions-waterlogging and acidity-may facilitate uptake and synthesis of protective phenolic compounds which are essential for impeded decomposition of organic matter in TPSF. Conversely, the ongoing drainage and degradation of TPSF, particularly for conversion to oil palm plantations, reverses the conditions necessary for peat accretion and carbon sequestration.

Comparison of adsorption and photo-Fenton processes for phenol and paracetamol removing from aqueous solutions: Single and binary systems

NASA Astrophysics Data System (ADS)

Rad, Leila Roshanfekr; Haririan, Ismaeil; Divsar, Faten

2015-02-01

In the present study, adsorption and photo-Fenton processes have been compared for the removal of phenol and paracetamol from aqueous solutions in a single and binary systems. NaX nanozeolites and cobalt ferrite nanoparticles were used during adsorption and photo-Fenton processes, respectively. Both nanoparticles were synthesized using microwave heating method. The synthesized nanoparticles were characterized using powder X-ray diffraction (XRD) and scanning electronic microscopy (SEM) analysis. Based on results, more than 99% removing percentages of phenol and paracetamol were obtained during photo-Fenton process at initial concentrations of 10, 20, 50, 100 and 200 mg/L of phenol and paracetamol. Moreover, the complete removing of phenol and paracetamol was only achieved at lower initial concentrations than 10 mg/L for phenol and paracetamol during adsorption process. The results showed a significant dependence of the phenol and paracetamol removing on the initial concentrations of phenol and paracetamol for selection of process. The photo-Fenton process could be considered an alternative method in higher initial concentrations of phenol and paracetamol. However, the adsorption process due to economical issue was preferred for phenol and paracetamol removing at lower initial concentrations. The kinetic data of photo-Fenton and adsorption processes were well described using first-order and pseudo-second-order kinetic models. The results of phenol and paracetamol removing in a binary system confirmed the obtained results of single removing of phenol and paracetamol in selection of process.

Hybridized Thermoplastic Aramids: Enabling Material Technology For Future Force Headgear

DTIC Science & Technology

2006-11-01

keeping the complete helmet weight the same. Design Material Rolled steel Hadfield Steel Kevlar 29/PVB Phenolic Kevlar 129/PVB...Material Rolled steel Hadfield Steel Kevlar 29/PVB Phenolic Kevlar 129/PVB phenolic Thermoplastic aramid Twaron/PVB phenolic ...Deflection RESULTS Improved Fiber, Fiber Architecture, and Matrix Materials Enable Performance Enhancement PASGT: 19 Ply S735 Kevlar with PVB Phenolic

Phenolic metabolites in carnivorous plants: Inter-specific comparison and physiological studies.

PubMed

Kováčik, Jozef; Klejdus, Bořivoj; Repčáková, Klára

2012-03-01

Despite intensive phytochemical research, data related to the accumulation of phenols in carnivorous plants include mainly qualitative reports. We have quantified phenolic metabolites in three species: Drosera capensis, Dionaea muscipula and Nepenthes anamensis in the "leaf" (assimilatory part) and the "trap" (digestive part). For comparison, commercial green tea was analysed. Phenylalanine ammonia-lyase (PAL) activities in Dionaea and Nepenthes were higher in the trap than in the leaf while the opposite was found in Drosera. Soluble phenols and majority of phenolic acids were mainly accumulated in the trap among species. Flavonoids were abundant in Drosera and Dionaea traps but not in Nepenthes. Phenolic acids were preferentially accumulated in a glycosidically-bound form and gallic acid was the main metabolite. Green tea contained more soluble phenols and phenolic acids but less quercetin. In vitro experiments with Drosera spathulata revealed that nitrogen deficiency enhances PAL activity, accumulation of phenols and sugars while PAL inhibitor (2-aminoindane-2-phosphonic acid) depleted phenols and some amino acids (but free phenylalanine and sugars were elevated). Possible explanations in physiological, biochemical and ecological context are discussed. Copyright © 2011 Elsevier Masson SAS. All rights reserved.

Plant phenolic compounds and oxidative stress: integrated signals in fungal-plant interactions.

PubMed

Shalaby, Samer; Horwitz, Benjamin A

2015-08-01

Upon invasion of a host, fungal pathogens are exposed to a variety of stresses. Plants release reactive oxygen species, and mount a variety of preformed and induced chemical defenses. Phenolic compounds are one example: they are ubiquitous in plants, and an invading pathogen encounters them already at the leaf surface, or for soil-borne pathogens, in the rhizosphere. Phenolic and related aromatic compounds show varying degrees of toxicity to cells. Some compounds are quite readily metabolized, and others less so. It was known already from classical studies that phenolic substrates induce the expression of the enzymes for their degradation. Recently, the ability to degrade phenolics was shown to be a virulence factor. Conversely, phenolic compounds can increase the effectiveness of antifungals. Phenolics are known antioxidants, yet they have been shown to elicit cellular responses that would usually be triggered to counter oxidant stress. Here, we review the evidence for a connection between the fungal response to phenolics as small-molecule signals, and the response to oxidants. The connections proposed here should enable genetic screens to identify specific fungal receptors for plant phenolics. Furthermore, understanding how the pathogen detects plant phenolic compounds as a stress signal may facilitate new antifungal strategies.

Influence of Various Phenolic Compounds on Properties of Gelatin Film Prepared from Horse Mackerel Trachurus japonicus Scales.

PubMed

Le, Thuy; Maki, Hiroki; Okazaki, Emiko; Osako, Kazufumi; Takahashi, Kigen

2018-06-15

Influence of various phenolic compounds on physical properties and antioxidant activity of gelatin film from horse mackerel Trachurus japonicus scales was investigated. Tensile strength (TS) of the film was enhanced whereas elongation at break was declined by adding 1% to 5% phenolic compounds. Rutin was the most effective to improve the TS compared to the other tested phenolic compounds including ferulic acid, caffeic acid, gallic acid, and catechin. Gelatin films with the phenolic compounds showed the excellent UV barrier properties. FTIR spectra exhibited that wavenumber of amide-A band of films decreased with formation of hydrogen bonding between amino groups of gelatin and hydroxyl groups of the phenolic compounds. Gelatin film incorporated with rutin which has the largest number of hydroxyl groups among the tested compounds demonstrated the lowest wavenumber for the amide-A peak. It is indicated that hydroxyl groups contained in the phenolic compounds contribute to formation of hydrogen bonds involved in improvement of the mechanical properties of the films. The incorporation of the phenolic compounds with gelatin films also led to the increasing of total phenolic contents and DPPH radical scavenging activities. Thus, it is concluded that phenolic compounds can promote the quality of gelatin film. Properties of gelatin film derived from horse mackerel scales can be improved by adding of phenolic compounds. Phenolic compounds containing a large number of hydroxyl groups should be selected to enhance physical properties of the gelatin film. A biodegradable film prepared from horse mackerel gelatin incorporated with phenolic compounds, which has good physical properties and antioxidant properties, can solve environmental problems caused by synthetic plastic materials. © 2018 Institute of Food Technologists®.

[Effect of soil phenolic acids on soil microbe of coal-mining depressed land after afforestation restoration by different tree species].

PubMed

Ji, Li; Yang, Li Xue

2017-12-01

Phenolic acids are one of the most important factors that influence microbial community structure. Investigating the dynamic changes of phenolic acids and their relationship with the microbial community structure in plantation soils with different tree species could contribute to better understanding and revealing the mechanisms of microbial community changes under afforestation restoration in coal-mining subsidence areas. In this study, plantations of three conifer and one deciduous species (Pinus koraiensis, Larix gmelinii, Pinus sylvestris var. mongolica, and Populus ussuriensis) were established on abandoned coal-mining subsidence areas in Baoshan District, Shuangyashan City. The contents of soil phenols, 11 types of phenolic acids, and microbial communities in all plots were determined. The results showed that the contents of soil complex phenol in plantations were significantly higher than that of abandoned land overall. Specifically, soils in larch and poplar plantations had higher contents of complex phenol, while soils in larch and Korean pine plantations had greater contents of total phenol. Moreover, soil in the P. koraiensis plantation had a higher content of water-soluble phenol compared with abandoned lands. The determination of 11 phenolic acids indicated that the contents of ferulic acid, abietic acid, β-sitosterol, oleanolic acid, shikimic acid, linoleic acid, and stearic acid were higher in plantation soils. Although soil phenol contents were not related with soil microbial biomass, the individual phenolic acids showed a significant relationship with soil microbes. Ferulic acid, abietic acid, and β-sitosterol showed significant promoting effects on soil microbial biomass, and they showed positive correlations with fungi and fungi/bacteria ratio. These three phenolic acids had higher contents in the poplar plantation, suggesting that poplar affo-restation had a beneficial effect on soil quality in coal-mining subsidence areas.

Analysis of phenolic compounds in different parts of pomegranate (Punica granatum) fruit by HPLC-PDA-ESI/MS and evaluation of their antioxidant activity: application to different Italian varieties.

PubMed

Russo, Marina; Fanali, Chiara; Tripodo, Giusy; Dugo, Paola; Muleo, Rosario; Dugo, Laura; De Gara, Laura; Mondello, Luigi

2018-06-01

The analysis of pomegranate phenolic compounds belonging to different classes in different fruit parts was performed by high-performance liquid chromatography coupled with photodiode array and mass spectrometry detection. Two different separation methods were optimized for the analysis of anthocyanins and hydrolyzable tannins along with phenolic acids and flavonoids. Two C 18 columns, core-shell and fully porous particle stationary phases, were used. The parameters for separation of phenolic compounds were optimized considering chromatographic resolution and analysis time. Thirty-five phenolic compounds were found, and 28 of them were tentatively identified as belonging to four different phenolic compound classes; namely, anthocyanins, phenolic acids, hydrolyzable tannins, and flavonoids. Quantitative analysis was performed with a mixture of nine phenolic compounds belonging to phenolic compound classes representative of pomegranate. The method was then fully validated in terms of retention time precision, expressed as the relative standard deviation, limit of detection, limit of quantification, and linearity range. Phenolic compounds were analyzed directly in pomegranate juice, and after solvent extraction with a mixture of water and methanol with a small percentage of acid in peel and pulp samples. The accuracy of the extraction method was also assessed, and satisfactory values were obtained. Finally, the method was used to study identified analytes in pomegranate juice, peel, and pulp of six different Italian varieties and one international variety. Differences in phenolic compound profiles among the different pomegranate parts were observed. Pomegranate peel samples showed a high concentration of phenolic compounds, ellagitannins being the most abundant ones, with respect to pulp and juice samples for each variety. With the same samples, total phenols and antioxidant activity were evaluated through colorimetric assays, and the results were correlated among them.

Inhibited phenol ionization in reverse micelles: confinement effect at the nanometer scale.

PubMed

Silva, O Fernando; Fernández, Mariana A; Silber, Juana J; de Rossi, Rita H; Correa, N Mariano

2012-01-16

We found that the absorption spectra of 2-acetylphenol (2-HAP), 4-acetylphenol (4-HAP), and p-nitrophenol (p-NPh) in water/sodium 1,4-bis(2-ethylhexyl)sulfosuccinate (AOT)/n-heptane reverse micelles (RMs) at various W(0) (W(0) = [H(2)O]/[surfactant]) values studied changed with time if (-)OH ions were present in the RM water pool. There is an evolution of ionized phenol (phenolate) bands to nonionized phenol absorption bands with time and this process is faster at low W(0) values and with phenols with higher bulk water pK(a) values. That is, in bulk water and at the hydroxide anion concentration used, only phenolate species are observed, whereas in AOT RMs at this fixed hydroxide anion concentration, ionized phenols convert into nonionized phenol species over time. Furthermore, we demonstrate that, independent of the (-)OH concentration used to prepare the AOT RMs, the nonionized phenols are the more stable species in the RM media. We explain our results by considering that strong hydrogen-bonding interactions between phenols and the AOT polar head groups result in the existence of only nonionized phenols at the AOT RM interface. The situation is quite different when the phenols are dissolved in cationic benzyl-n-hexadecyldimethylammonium chloride RMs. Therein, only phenolates species are present at the (-)OH concentrations used. The results clearly demonstrate that the classical definition of pH does not apply in a confined environment, such as in the interior of RMs and challenge the general idea that pH can be determined inside RMs. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Phenolic acids in the flowers of Althaea rosea var. nigra.

PubMed

Dudek, Marlena; Matławska, Irena; Szkudlarek, Maurycy

2006-01-01

Distribution of phenolic acids in the flowers of Althaea rosea var. nigra has been studied by 2D-TLC and HPLC methods. The phenolic acids occurring in these fractions have been identified as ferulic, vanillic, syringic, p-coumaric, p-hydroxybenzoic, p-hydroxyphenylacetic and caffeic acids. By means of the HPLC methods the contents of major phenolic acids were estimated. From among the phenolic acids analyzed the syringic, p-hydroxybenzoic and p-coumaric acids are dominant. Total content of phenolic acids was determined by the Arnov's method.

The reactivity of phenolic and non-phenolic residual kraft lignin model compounds with Mn(II)-peroxidase from Lentinula edodes.

PubMed

Crestini, C; D'Annibale, A; Sermanni, G G; Saladino, R

2000-02-01

Three phenolic model compounds representing bonding patterns of residual kraft lignin were incubated with manganese peroxidase from Lentinula edodes. Extensive degradation of all the phenolic models, mainly occurring via side-chain benzylic oxidation, was observed. Among the tested model compounds the diphenylmethane alpha-5 phenolic model was found to be the most reactive, yielding several products showing oxidation and fragmentation at the bridging position. The non-phenolic 5-5' biphenyl and 5-5' diphenylmethane models were found unreactive.

Monochloro non-bridged half-metallocene-type zirconium complexes containing phosphine oxide-(thio)phenolate chelating ligands as efficient ethylene polymerization catalysts.

PubMed

Tang, Xiao-Yan; Wang, Yong-Xia; Liu, San-Rong; Liu, Jing-Yu; Li, Yue-Sheng

2013-01-14

A series of novel monochloro half-zirconocene complexes containing phosphine oxide-(thio)phenolate chelating ligands of the type, ClCp'Zr[X-2-R(1)-4-R(2)-6-(Ph(2)P=O)C(6)H(2)](2) (Cp' = C(5)H(5), 2a: X = O, R(1) = Ph, R(2) = H; 2b: X = O, R(1) = F, R(2) = H; 2c: X = O, R(1) = (t)Bu, R(2) = H; 2d: X = O, R(1) = R(2) = (t)Bu; 2e: X = O, R(1) = SiMe(3), R(2) = H; 2f: X = S, R(1) = SiMe(3), R(2) = H; Cp' = C(5)Me(5), 2g: X = O, R(1) = SiMe(3), R(2) = H), have been synthesized in high yields. These complexes were identified by (1)H {(13)C} NMR and elemental analyses. Structures for 2b, 2c and 2f were further confirmed by X-ray crystallography. Structural characterization of these complexes reveals crowded environments around the zirconium. Complexes 2b and 2c adopt six-coordinate, distorted octahedral geometry around the zirconium center, in which the equatorial positions are occupied by three oxygen atoms of two chelating phosphine oxide-bridged phenolate ligands and a chlorine atom. The cyclopentadienyl ring and one oxygen atom of the ligand are coordinated on the axial position. Complex 2f also folds a six-coordinate, distorted octahedral geometry around the Zr center, consisting of a Cp-Zr-O (in P=O) axis [177.16°] and a distorted plane of two sulfur atoms and one oxygen atom of two chelating phosphine oxide-bridged thiophenolate ligands as well as a chlorine atom. When activated by modified methylaluminoxane (MMAO), all the complexes exhibited high activities towards ethylene polymerization at high temperature (75 °C), giving high molecular weight polymers with unimodal molecular weight distribution. The formation of 14-electron, cationic metal alkyl species might come from the Zr-O (in phenol ring) bond cleavage based on the DFT calculations study.

Influence of different nominal molecular weight fractions of humic acids on phenol oxidation by permanganate.

PubMed

He, Di; Guan, Xiaohong; Ma, Jun; Yu, Min

2009-11-01

The effects of humic acid (HA) and its different nominal molecular weight (NMW) fractions on the phenol oxidation by permanganate were studied. Phenol oxidation by permanganate was enhanced by the presence of HA at pH 4-8, while slightly inhibited at pH 9-10. The effects of HA on phenol oxidation by permanganate were dependent on HA concentration and permanganate/phenol molar ratios. The high NMW fractions of HA enhanced phenol oxidation by permanganate at pH 7 more significantly than the low fractions of HA. The apparent second-order rate constants of phenol oxidation by permanganate in the presence of HA correlated well with their specific ultraviolet absorption (SUVA) at 254 nm and specific violet absorption (SVA) at 465 or 665 nm. High positive correlation coefficients (R(2) > 0.72) implied that pi-electrons of HA strongly influenced the reactivity of phenol towards permanganate oxidation which agreed well with the information provided by fluorescence spectroscopy. The FTIR analysis indicated that the HA fractions rich in aliphatic character, polysaccharide-like substances, and the amount of carboxylate groups had less effect on phenol oxidation by permanganate. The negative correlation between the rate constants of phenol oxidation by permanganate and O/C ratios suggested that the oxidation of phenol increased with a decrease in the content of oxygen-containing functional groups.

Phenolic content variability and its chromosome location in tritordeum

PubMed Central

Navas-Lopez, José F.; Ostos-Garrido, Francisco J.; Castillo, Almudena; Martín, Antonio; Gimenez, Maria J.; Pistón, Fernando

2014-01-01

For humans, wheat is the most important source of calories, but it is also a source of antioxidant compounds that are involved in the prevention of chronic disease. Among the antioxidant compounds, phenolic acids have great potential to improve human health. In this paper we evaluate the effect of environmental and genetic factors on the phenolics content in the grain of a collection of tritordeums with different cytoplasm and chromosome substitutions. To this purpose, tritordeum flour was used for extraction of the free, conjugates and bound phenolic compounds. These phenolic compounds were identified and quantified by RP-HPLC and the results were analyzed by univariate and multivariate methods. This is the first study that describes the composition of phenolic acids of the amphiploid tritordeum. As in wheat, the predominant phenolic compound is ferulic acid. In tritordeum there is great variability for the content of phenolic compounds and the main factor which determines its content is the genotype followed by the environment, in this case included in the year factor. Phenolic acid content is associated with the substitution of chromosome DS1D(1Hch) and DS2D(2Hch), and the translocation 1RS/1BL in tritordeum. The results show that there is high potential for further improving the quality and quantity of phenolics in tritordeum because this amphiploid shows high variability for the content of phenolic compounds. PMID:24523725

The toxicity of binary mixture of Cu (II) ion and phenols on Tetrahymena thermophila.

PubMed

Luo, Hui; Li, Xi; Fang, Tingting; Liu, Peng; Zhang, Chaocan; Xie, Hao; Sun, Enjie

2015-03-01

The toxicity of binary mixture of Cu(2+) and phenols (phenol; o-nitrophenol; m-nitrophenol; p-nitrophenol) was evaluated using Tetrahymena thermophila as the model organism, by microcalorimetry, optical density, field emission scanning electron microscope (FESEM) and attenuated total reflection-Fourier transform infrared spectroscopy (ATR-FTIR). The growth curves and metabolic properties of Tetrahymena exposed to Cu(2+) and phenols were monitored by microcalorimetry. Binary mixture toxicity changed with the concentration of Cu(2+)/phenols and the order of toxicity was Cu(2+)/phenol

Obtention and characterization of phenolic extracts from different cocoa sources.

PubMed

Ortega, Nàdia; Romero, Maria-Paz; Macià, Alba; Reguant, Jordi; Anglès, Neus; Morelló, José-Ramón; Motilva, Maria-Jose

2008-10-22

The aim of this study was to evaluate several cocoa sources to obtain a rich phenol extract for use as an ingredient in the food industry. Two types of phenolic extracts, complete and purified, from different cocoa sources (beans, nibs, liquor, and cocoa powder) were investigated. UPLC-MS/MS was used to identify and quantify the phenolic composition of the extracts, and the Folin-Ciocalteu and vanillin assays were used to determine the total phenolic and flavan-3-ol contents, respectively. The DPPH and ORAC assays were used to measure their antioxidant activity. The results of the analysis of the composition of the extracts revealed that the major fraction was procyanidins, followed by flavones and phenolic acids. From the obtained results, the nib could be considered the most interesting source for obtaining a rich phenolic cocoa extract because of its rich phenolic profile content and high antioxidant activity in comparison with the other cocoa sources.

Testing Electrostatic Complementarity in Enzyme Catalysis: Hydrogen Bonding in the Ketosteroid Isomerase Oxyanion Hole

PubMed Central

Kraut, Daniel A; Sigala, Paul A; Pybus, Brandon; Liu, Corey W; Ringe, Dagmar; Petsko, Gregory A

2006-01-01

A longstanding proposal in enzymology is that enzymes are electrostatically and geometrically complementary to the transition states of the reactions they catalyze and that this complementarity contributes to catalysis. Experimental evaluation of this contribution, however, has been difficult. We have systematically dissected the potential contribution to catalysis from electrostatic complementarity in ketosteroid isomerase. Phenolates, analogs of the transition state and reaction intermediate, bind and accept two hydrogen bonds in an active site oxyanion hole. The binding of substituted phenolates of constant molecular shape but increasing p K a models the charge accumulation in the oxyanion hole during the enzymatic reaction. As charge localization increases, the NMR chemical shifts of protons involved in oxyanion hole hydrogen bonds increase by 0.50–0.76 ppm/p K a unit, suggesting a bond shortening of ˜0.02 Å/p K a unit. Nevertheless, there is little change in binding affinity across a series of substituted phenolates (ΔΔG = −0.2 kcal/mol/p K a unit). The small effect of increased charge localization on affinity occurs despite the shortening of the hydrogen bonds and a large favorable change in binding enthalpy (ΔΔH = −2.0 kcal/mol/p K a unit). This shallow dependence of binding affinity suggests that electrostatic complementarity in the oxyanion hole makes at most a modest contribution to catalysis of ˜300-fold. We propose that geometrical complementarity between the oxyanion hole hydrogen-bond donors and the transition state oxyanion provides a significant catalytic contribution, and suggest that KSI, like other enzymes, achieves its catalytic prowess through a combination of modest contributions from several mechanisms rather than from a single dominant contribution. PMID:16602823

Determination of 4-nonylphenol in water samples using 4-(2,6-dimethylhept-3-yl)phenol as new internal standard.

PubMed

Fischer, Axel R; Lan, Nham Thi Phuong; Wiedemann, Cornelia; Heide, Petra; Werner, Peter; Schmidt, Arndt W; Theumer, Gabriele; Knölker, Hans-Joachim

2010-04-23

A new method for determining the endocrine disrupting substance 4-nonylphenol (technical grade=mixture of isomers, 4-NP) from water samples has been developed by using 4-(2,6-dimethylhept-3-yl)phenol (4-sec-NP) as model compound. This branched monoalkylphenol is shown to serve as internal standard (IS) for the determination of technical 4-nonylphenol. To the best of our knowledge, 4-(2,6-dimethylhept-3-yl)phenol (racemic mixture) is a newly synthesized 4-nonylphenol isomer and has not been described elsewhere. Recoveries have been determined by analyzing spiked water samples from distilled water, river water and wastewater. Following acetylation, the compounds were enriched via solid phase extraction (SPE). Analyses of the compounds were performed by capillary column gas chromatography/mass spectrometry (GC/MS), operating in selected ion-monitoring (SIM) mode. The recovery of technical 4-NP using either the newly prepared 4-sec-NP or 4-n-nonylphenol (4-n-NP) as IS have been compared. 4-sec-NP showed slightly better results. However, in the first series of experiments using wastewater, the yields for the derivatization of the two standard compounds were remarkably different. The yield for derivatization of 4-n-NP was approximately 20%, probably due to the difficult matrix of the wastewater. In contrast, the yield for the derivatization of 4-sec-NP was considerably higher (approximately 63%). This problem can be solved by increasing the concentration of the reagent used for derivatization. For better control of the clean-up process, we recommend application of 4-sec-NP as internal standard, at least in water samples with complex matrices (e.g., high content of hydroxylated compounds). Copyright 2010 Elsevier B.V. All rights reserved.

Structure and photocatalytic activity studies of TiO{sub 2}-supported over Ce-modified Al-MCM-41

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

Krishna Reddy, Jakkidi; Durgakumari, Valluri, E-mail: durgakumari@iict.res.in; Subrahmanyam, Machiraju

2009-07-01

Ce-Al-MCM-41, TiO{sub 2}/Al-MCM-41 and TiO{sub 2}/Ce-Al-MCM-41 materials with varying contents of Ce (by impregnation) and TiO{sub 2} loaded (by solid-state dispersion) on Al-MCM-41 support are prepared. The Ce modified and TiO{sub 2} loaded composite systems are characterized by X-ray diffraction (XRD), transmission electron microscopy (TEM), UV-vis diffuse reflectance spectra (DRS) and X-ray photoelectron spectroscopy (XPS) techniques. The DRS and XPS of low Ce content (0.2-0.5 wt.%) modified Al-MCM-41 samples are showing more characteristic of Ce{sup 3+} species wherein cerium in interaction with Al-MCM-41 and that of high Ce (0.8, 3.0 wt.%) content modified samples are showing the characteristic of bothmore » Ce{sup 4+}and Ce{sup 3+}species. A series of Ce-modified Al-MCM-41 and TiO{sub 2} loaded composite catalysts are evaluated for photocatalytic degradation of phenol under UV irradiation. Low Ce content in Ce{sup 3+} state on Al-MCM-41 is showing good photoactivity in comparison with high Ce content samples and pure ceria. The composite TiO{sub 2}/Ce-Al-MCM-41 is showing enhanced degradation activity due decreased rate of electron-hole recombination on TiO{sub 2} surface by the redox properties of cerium. The photocatalyst TiO{sub 2}/Ce-Al-MCM-41 with an optimum of 10 wt.% TiO{sub 2} and 0.3 wt.% Ce is showing maximum phenol degradation activity. The possible mechanism of phenol degradation on the composite photocatalyst is proposed.« less

Prospecting Russula senecis: a delicacy among the tribes of West Bengal

PubMed Central

Khatua, Somanjana; Dutta, Arun Kumar

2015-01-01

Russula senecis, a worldwide distributed mushroom, is exclusively popular among the tribal communities of West Bengal for food purposes. The present study focuses on its reliable taxonomic identification through macro- and micro-morphological features, DNA barcoding, confirmation of its systematic placement by phylogenetic analyses, myco-chemicals and functional activities. For the first time, the complete Internal Transcribed Spacer region of R. senecis has been sequenced and its taxonomic position within subsection Foetentinae under series Ingratae of the subgen. Ingratula is confirmed through phylogenetic analysis. For exploration of its medicinal properties, dried basidiocarps were subjected for preparation of a heat stable phenol rich extract (RusePre) using water and ethanol as solvent system. The antioxidant activity was evaluated through hydroxyl radical scavenging (EC50 5 µg/ml), chelating ability of ferrous ion (EC50 0.158 mg/ml), DPPH radical scavenging (EC50 1.34 mg/ml), reducing power (EC50 2.495 mg/ml) and total antioxidant activity methods (13.44 µg ascorbic acid equivalent/mg of extract). RusePre exhibited antimicrobial potentiality against Listeria monocytogenes, Bacillus subtilis, Pseudomonas aeruginosa and Staphylococcus aureus. Furthermore, different parameters were tested to investigate its chemical composition, which revealed the presence of appreciable quantity of phenolic compounds, along with carotenoids and ascorbic acid. HPLC-UV fingerprint indicated the probable existence of at least 13 phenolics, of which 10 were identified (pyrogallol > kaempferol > quercetin > chlorogenic acid > ferulic acid, cinnamic acid > vanillic acid > salicylic acid > p-coumaric acid > gallic acid). Result from the present work suggests that the fraction, RusePre, may open novel prospect as a functional ingredient in antioxidant supplements and in drugs to treat infectious disease. PMID:25780764

Analysis of Substrate Access to Active Sites in Bacterial Multicomponent Monooxygenase Hydroxylases: X-ray Crystal Structure of Xenon-Pressurized Phenol Hydroxylase from Pseudomonas sp. OX1†,‡

PubMed Central

McCormick, Michael S.; Lippard, Stephen J.

2011-01-01

In all structurally characterized bacterial multicomponent monooxygenase (BMM) hydroxylase proteins, a series of hydrophobic cavities in the α-subunit trace a conserved path from the protein exterior to the carboxylate-bridged diiron active site. The present study examines these cavities as a potential route for dioxygen transport to the active site by crystallographic characterization of a xenon-pressurized sample of the hydroxylase component of phenol hydroxylase from Pseudomonas sp. OX1. Computational analyses of the hydrophobic cavities in the hydroxylase α-subunits of phenol hydroxylase (PHH), toluene/o-xylene monooxygenase (ToMOH), and soluble methane monooxygenase (sMMOH) are also presented. The results, together with previous findings from crystallographic studies of xenon-pressurized sMMO hydroxylase, clearly identify the propensity for these cavities to bind hydrophobic gas molecules in the protein interior. This proposed functional role is supported by recent stopped flow kinetic studies of ToMOH variants (Song, et al., 2011). In addition to information about the Xe sites, the structure determination revealed significantly reduced regulatory protein binding to the hydroxylase in comparison to the previously reported structure of PHH, as well as the presence of a newly identified metal binding site in the α-subunit that adopts a linear coordination environment consistent with Cu(I), and a glycerol molecule bound to Fe1 in a fashion that is unique among hydrocarbon-diiron site adducts reported to date in BMM hydroxylase structures. Finally, a comparative analysis of the α-subunit structures of MMOH, ToMOH, and PHH details proposed routes for the other three BMM substrates, the hydrocarbon, electrons, and protons, comprising cavities, channels, hydrogen-bonding networks, and pores in the structures of their α-subunits. PMID:22136180

Combination of ozonation and photocatalysis for pharmaceutical wastewater treatment

NASA Astrophysics Data System (ADS)

Ratnawati, Enjarlis, Slamet

2017-11-01

The chemical oxygen demand (COD) and phenol removal from pharmaceutical wastewater were investigated using configuration of two circulation batch reactors in a series with ozonation and photocatalytic processes. The ozonation is conducted with O3/granulated activated carbon (O3/GAC), whereas photocatalysis with TiO2 that immobilized on pumice stone (PS-TiO2). The effect of circulation flow rate (10; 12; 15 L/min) and the amount PS-TiO2 (200 g, 250 g, 300 g) were examined. Wastewater of 20 L was circulated pass through the pipe that injected with O3 by the ozone generator, and subsequently flow through two GAC columns, and finally, go through photoreactor that contains photocatalyst PS-TiO2 which equipped with mercury lamp as a photon source. At a time interval, COD and phenol concentration were measured to assess the performance of the process. FESEM imaging confirmed that TiO2 was successfully impregnated on PS, as corroborated by EDX spectra. Meanwhile, degradation process indicated that the combined ozonation and photocatalytic processes (O3/GAC-TiO2) is more efficient compared to the ozonation and photocatalysis alone. For combination process with the circulation flow rate of 10 L/min and 300 g of PS-TiO2,the influent COD of around 1000 ppm are effectively degraded to a final effluent COD of 290 ppm (71% removal) and initial phenol concentration of 4.75 ppm down to 0 ppm for 4 h which this condition fulfill the discharge standards quality. Therefore, this portable prototype reactor is effective that can be used in the pharmaceutical wastewater treatment. For the future, this process condition will be developed for orientation on the industrial applications (portable equipment) since pharmaceutical industries produce wastewater relatively in the small amount.

3D-printed and CNC milled flow-cells for chemiluminescence detection.

PubMed

Spilstead, Kara B; Learey, Jessica J; Doeven, Egan H; Barbante, Gregory J; Mohr, Stephan; Barnett, Neil W; Terry, Jessica M; Hall, Robynne M; Francis, Paul S

2014-08-01

Herein we explore modern fabrication techniques for the development of chemiluminescence detection flow-cells with features not attainable using the traditional coiled tubing approach. This includes the first 3D-printed chemiluminescence flow-cells, and a milled flow-cell designed to split the analyte stream into two separate detection zones within the same polymer chip. The flow-cells are compared to conventional detection systems using flow injection analysis (FIA) and high performance liquid chromatography (HPLC), with the fast chemiluminescence reactions of an acidic potassium permanganate reagent with morphine and a series of adrenergic phenolic amines. Copyright © 2014 Elsevier B.V. All rights reserved.

Molecular design of anti-MRSA agents based on the anacardic acid scaffold.

PubMed

Green, Ivan R; Tocoli, Felismino E; Lee, Sang Hwa; Nihei, Ken-Ichi; Kubo, Isao

2007-09-15

A series of anacardic acid analogues possessing different side chains viz. phenolic, branched, and alicyclic were synthesized and their antibacterial activity tested against methicillin-resistant Staphylococcus aureus (MRSA). The maximum activity against this bacterium occurred with the branched side-chain analogue, 6-(4',8'-dimethylnonyl)salicylic acid, and the alicyclic side-chain analogue, 6-cyclododecylmethyl salicylic acid, with the minimum inhibitory concentration (MIC) of 0.39 microg/mL, respectively. This activity was superior to that of the most potent antibacterial anacardic acid isolated from the cashew Anacardium occidentale (Anacardiaceae), apple and nut, that is, the 6-[8'(Z),11'(Z),14'-pentadecatrienyl]salicylic acid.

Thermally-generated reactive intermediates: Trapping of the parent ferrocene-based o-quinodimethane and reactions of diradicals generated by hydrogen-atom transfers

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

Ferguson, John Michael

1993-09-01

Ferrocenocyclobutene is prepared by flash vacuum pyrolysis (FVP) of the N-amino-2-phenylaziridine hydrazone of 2-methylferrocenealdehyde. In the second section of this dissertation, a series of hydrocarbon rearrangements were observed. FVP of o-allyltoluene at 0.1 Torr (700--900 C) gives 2-methylindan and indene, accompanied by o-propenyltoluene. FVP of 2-methyl-2`-vinylbiphenyl gives 9-methyl-9,10-dihydrophenanthrene, which fits the proposed mechanism. However, FVP of 2-(o-methylbenzyl)styrene gives mainly anthracene and 1-methylanthracene. This cyclization reaction was also successful with o-allylphenol and o-(2-methylallyl)phenol.

Maple syrup-production, composition, chemistry, and sensory characteristics.

PubMed

Perkins, Timothy D; van den Berg, Abby K

2009-01-01

Maple syrup is made from sap exuded from stems of the genus Acer during the springtime. Sap is a dilute solution of primarily water and sucrose, with varying amounts of amino and organic acids and phenolic substances. When concentrated, usually by heating, a series of complex reactions produce a wide variety of flavor compounds that vary due to processing and other management factors, seasonal changes in sap chemistry, and microbial contamination. Color also forms during thermal evaporation. Flavor and color together are the primary factors determining maple syrup grade, and syrup can range from very light-colored and delicate-flavored to very dark-colored and strong-flavored.

Flammability and Photo-Stability of Selected Polymer Systems

DTIC Science & Technology

1981-06-01

modifications. The 13. following methods have been used(2 8 ) : 1. Etherification or esterification of the phenolic hydroxyl groups, 2. Complex...is initiated with a view to making modifications of the flammability behaviors of phenolic resin by using substituted phenols. Also. esterification of...n-substituted phenolic resins. Modification by esterification has also been reported by Lei(29) in the synthesis of n-chloro- phenolic fiber. The

Phenolic Composition and Evaluation of the Antimicrobial Activity of Free and Bound Phenolic Fractions from a Peruvian Purple Corn (Zea mays L.) Accession.

PubMed

Gálvez Ranilla, Lena; Christopher, Ashish; Sarkar, Dipayan; Shetty, Kalidas; Chirinos, Rosana; Campos, David

2017-12-01

Beneficial effects on overall gut health by phenolic bioactives-rich foods are potentially due to their modulation of probiotic gut bacteria and antimicrobial activity against pathogenic bacteria. Based on this rationale, the effect of the free and bound phenolic fractions from a Peruvian purple corn accession AREQ-084 on probiotic lactic acid bacteria such as Lactobacillus helveticus and Bifidobacterium longum and the gastric cancer-related pathogen Helicobacter pylori was evaluated. The free and bound phenolic composition was also determined by ultra-performance liquid chromatography. Anthocyanins were the major phenolic compounds (310.04 mg cyanidin-3-glucoside equivalents/100 g dry weight, DW) in the free phenolic fraction along with hydroxycinnamic acids such as p-coumaric acid derivatives, followed by caffeic and ferulic acid derivatives. The bound phenolic form had only hydroxycinnamic acids such as ferulic acid, p-coumaric acid, and a ferulic acid derivative with ferulic acid being the major phenolic compound (156.30 mg/100 g DW). These phenolic compounds were compatible with beneficial probiotic lactic acid bacteria such as L. helveticus and B. longum as these bacteria were not inhibited by the free and bound phenolic fractions at 10 to 50 mg/mL and 10 mg/mL of sample doses, respectively. However, the pathogenic H. pylori was also not inhibited by both purple corn phenolic forms at same above sample doses. This study provides the preliminary base for the characterization of phenolic compounds of Peruvian purple corn biodiversity and its potential health benefits relevant to improving human gut health. This study provides insights that Peruvian purple corn accession AREQ-084 can be targeted as a potential source of health-relevant phenolic compounds such as anthocyanins along with hydroxycinnamic acids linked to its dietary fiber fraction. Additionally, these phenolic fractions did not affect the gut health associated beneficial bacteria nor the pathogenic H. pylori. Purple corn can be targeted for design of probiotic functional foods integrated with their anthocyanin linked-coloring properties. © 2017 Institute of Food Technologists®.

Treatment of wastewater containing phenol using a tubular ceramic membrane bioreactor.

PubMed

Ersu, C B; Ong, S K

2008-02-01

The performance of a membrane bioreactor (MBR) with a tubular ceramic membrane for phenol removal was evaluated under varying hydraulic retention times (HRT) and a fixed sludge residence time (SRT) of 30 days. The tubular ceramic membrane was operated with a mode of 15 minutes of filtration followed by 15 seconds of permeate backwashing at a flux of 250 l m(-2)hr(-1) along with an extended backwashing of 30 seconds every 3 hours of operation, which maintained the transmembrane pressure (TMP) below 100 kPa. Using a simulated municipal wastewater with varying phenol concentrations, the chemical oxygen demand (COD) and phenol removals observed were greater than 88% with excellent suspended solids (SS) removal of 100% at low phenol concentrations (approx. 100 mg l(-1) of phenol). Step increases in phenol concentration showed that inhibition was observed between 600 to 800 mg l(-1) of phenol with decreased sludge production rate, mixed liquor suspended solids (MLSS) concentration, and removal performance. The sludge volume index (SVI) of the biomass increased to about 450 ml g(-1) for a phenol input concentration of 800 mg l(-1). When the phenol concentration was decreased to 100 mg l(-1), the ceramic tubular MBR was found to recover rapidly indicating that the MBR is a robust system retaining most of the biomass. Experimental runs using wastewater containing phenol indicated that the MBR can be operated safely without upsets for concentrations up to 600 mg l(-1) of phenol at 2-4 hours HRT and 30 days SRT.

Synthesis and characterization of catalysts for the selective transformation of biomass-derived materials

NASA Astrophysics Data System (ADS)

Ghampson, Isaac Tyrone

The experimental work in this thesis focuses on generating catalysts for two intermediate processes related to the thermal conversion of lignocellulosic biomass: the synthesis and characterization of mesoporous silica supported cobalt catalysts for the Fischer-Tropsch reaction, and an exploration of the reactivity of bulk and supported molybdenum-based nitride catalysts for the hydrodeoxygenation (HDO) of guaiacol, a lignin model compound. The first section of the work details the synthesis of a series of silica-supported cobalt Fischer-Tropsch catalysts with pore diameters ranging from 2-23 nm. Detailed X-ray diffraction measurements were used to determine the composition and particle diameters of the metal fraction, analyzed as a three-phase system containing Cofcc, Cohcp and CoO particles. Catalyst properties were determined at three stages in catalyst history: (1) after the initial calcination step to thermally decompose the catalyst precursor into Co3O4, (2) after the hydrogen reduction step to activate the catalyst to Co and (3) after the FT reaction. From the study, it was observed that larger pore diameters supported higher turnover frequency; smaller pore diameters yielded larger mole fraction of CoO; XRD on post-reduction and post-FTS catalyst samples indicated significant changes in dispersivity after reduction. In the next section, the catalytic behaviors of unsupported, activated carbon-, alumina-, and SBA-15 mesoporous silica-supported molybdenum nitride catalysts were evaluated for the hydrodeoxygenation of guaiacol (2-methoxy phenol) at 300°C and 5 MPa. The nitride catalysts were prepared by thermal decomposition of bulk and supported ammonium heptamolybdate to form MoO 3 followed by nitridation in either flowing ammonia or a nitrogen/hydrogen mixture. The catalytic properties were strongly affected by the nitriding and purging treatment as well as the physical and chemical properties of support. The overall reaction was influenced by the crystalline phase present in the catalyst, dispersion of molybdenum nitride/oxynitride, and the porosity of the support. The hydrodeoxygenation of guaiacol followed two proposed reaction pathways: demethylation (DME) of guaiacol to form catechol, followed by dehydroxylation to form phenol; or a direct demethoxylation (DMO) to form phenol. The selectivity of the reaction was expressed in terms of the phenol/catechol ratio. Phenol was the predominant product for all the catalysts studied, except for the alumina-supported catalysts (an effect of the alumina support). The results from this thesis are encouraging for the application of Mo nitride based catalysts for hydrodeoxygenation of whole pyrolysis oil.

Breads enriched with guava flour as a tool for studying the incorporation of phenolic compounds in bread melanoidins.

PubMed

Alves, Genilton; Perrone, Daniel

2015-10-15

In the present study we aimed at studying, for the first time, the incorporation of phenolic compounds into bread melanoidins. Fermentation significantly affected the phenolics profile of bread doughs. Melanoidins contents continuously increased from 24.1 mg/g to 71.9 mg/g during baking, but their molecular weight decreased at the beginning of the process and increased thereafter. Enrichment of white wheat bread with guava flour increased the incorporation of phenolic compounds up to 2.4-fold. Most phenolic compounds showed higher incorporation than release rates during baking, leading to increases from 3.3- to 13.3-fold in total melanoidin-bound phenolics. Incorporation patterns suggested that phenolic hydroxyls, but not glycosidic bonds of melanoidin-bound phenolics are cleaved during thermal processing. Antioxidant capacity of bread melanoidins increased due to enrichment with guava flour and increasing baking periods and was partially attributed to bound phenolics. Moreover, FRAP assay was more sensitive to measure this parameter than TEAC assay. Copyright © 2015 Elsevier Ltd. All rights reserved.

Fermentation and complex enzyme hydrolysis for improving the total soluble phenolic contents, flavonoid aglycones contents and bio-activities of guava leaves tea.

PubMed

Wang, Lu; Luo, You; Wu, Yanan; Liu, Yan; Wu, Zhenqiang

2018-10-30

There are both soluble and insoluble-bound forms of phenolics in tea-leaf products. In order to increase total soluble phenolics contents, guava leaves tea (GLT) was first fermented with Monascus anka and Saccharomyces cerevisiae, and then hydrolyzed with complex enzymes. The changes in phenolics profiles, antioxidant activities and inhibitory effect on α-glucosidase in processed GLT were investigated. Compared with the un-fermented GLT, fermentation and complex enzymatic processing (FE) significantly increased the total phenolics, total flavonoids, quercetin and kaempferol contents by 2.1, 2.0, 13.0 and 6.8 times, respectively. After the FE, a major proportion of phenolics existed in the soluble form. Quercetin was released in the highest amount among different phenolics. In addition, soluble phenolic extracts from GLT following FE exhibited a highest antioxidant activity and inhibitory effect on α-glucosidase. The paper suggested an improved method for processing GLT into high-value products rich in phenolics and flavonoids aglycones with enhanced health benefits. Copyright © 2018 Elsevier Ltd. All rights reserved.

Dynamic Changes in Phenolics and Antioxidant Capacity during Pecan (Carya illinoinensis) Kernel Ripening and Its Phenolics Profiles.

PubMed

Jia, Xiaodong; Luo, Huiting; Xu, Mengyang; Zhai, Min; Guo, Zhongren; Qiao, Yushan; Wang, Liangju

2018-02-16

Pecan ( Carya illinoinensis ) kernels have a high phenolics content and a high antioxidant capacity compared to other nuts-traits that have attracted great interest of late. Changes in the total phenolic content (TPC), condensed tannins (CT), total flavonoid content (TFC), five individual phenolics, and antioxidant capacity of five pecan cultivars were investigated during the process of kernel ripening. Ultra-performance liquid chromatography coupled with quadruple time-of-flight mass (UPLC-Q/TOF-MS) was also used to analyze the phenolics profiles in mixed pecan kernels. TPC, CT, TFC, individual phenolics, and antioxidant capacity were changed in similar patterns, with values highest at the water or milk stages, lowest at milk or dough stages, and slightly varied at kernel stages. Forty phenolics were tentatively identified in pecan kernels, of which two were first reported in the genus Carya , six were first reported in Carya illinoinensis , and one was first reported in its kernel. The findings on these new phenolic compounds provide proof of the high antioxidant capacity of pecan kernels.

Determination of free, esterified, glycosylated and insoluble-bound phenolics composition in the edible part of araticum fruit (Annona crassiflora Mart.) and its by-products by HPLC-ESI-MS/MS.

PubMed

Arruda, Henrique Silvano; Pereira, Gustavo Araujo; de Morais, Damila Rodrigues; Eberlin, Marcos Nogueira; Pastore, Glaucia Maria

2018-04-15

Phenolics present in the free, esterified, glycosylated and insoluble-bound forms of araticum pulp, peel and seed were for the first time characterized and quantified using HPLC-ESI-MS/MS. Levels of total phenolics, flavonoids, condensed tannins and antioxidant activities from araticum fruit followed the order peel > pulp > seed. Overall, insoluble-bound and esterified phenolics were the dominant forms of phenolics from araticum fruit parts and the highest contributors to their antioxidant activities. Extracts were found to contain contrasting levels of phenolics that were specific to each fruit part. From 10 phenolics quantified in araticum fruit, catechin and epicatechin were the major ones from pulp and peel, whereas seed displayed caffeic acid, catechin and epicatechin as its main phenolics. Araticum fruit was found to provide a good source of phenolics, and the full exploitation of this fruit may find applications in the food, cosmetic and pharmaceutical industries. Copyright © 2017 Elsevier Ltd. All rights reserved.

In-Depth Two-Year Study of Phenolic Profile Variability among Olive Oils from Autochthonous and Mediterranean Varieties in Morocco, as Revealed by a LC-MS Chemometric Profiling Approach.

PubMed

Bajoub, Aadil; Medina-Rodríguez, Santiago; Olmo-García, Lucía; Ajal, El Amine; Monasterio, Romina P; Hanine, Hafida; Fernández-Gutiérrez, Alberto; Carrasco-Pancorbo, Alegría

2016-12-28

Olive oil phenolic fraction considerably contributes to the sensory quality and nutritional value of this foodstuff. Herein, the phenolic fraction of 203 olive oil samples extracted from fruits of four autochthonous Moroccan cultivars ("Picholine Marocaine", "Dahbia", "Haouzia" and "Menara"), and nine Mediterranean varieties recently introduced in Morocco ("Arbequina", "Arbosana", "Cornicabra", "Frantoio", "Hojiblanca", "Koroneiki", "Manzanilla", "Picholine de Languedoc" and "Picual"), were explored over two consecutive crop seasons (2012/2013 and 2013/2014) by using liquid chromatography-mass spectrometry. A total of 32 phenolic compounds (and quinic acid), belonging to five chemical classes (secoiridoids, simple phenols, flavonoids, lignans and phenolic acids) were identified and quantified. Phenolic profiling revealed that the determined phenolic compounds showed variety-dependent levels, being, at the same time, significantly affected by the crop season. Moreover, based on the obtained phenolic composition and chemometric linear discriminant analysis, statistical models were obtained allowing a very satisfactory classification and prediction of the varietal origin of the studied oils.

Effects of Vinification Techniques Combined with UV-C Irradiation on Phenolic Contents of Red Wines.

PubMed

Tahmaz, Hande; Söylemezoğlu, Gökhan

2017-06-01

Red wines are typically high in phenolic and antioxidant capacity and both of which can be increased by vinification techniques. This study employed 3 vinification techniques to assess the increase in phenolic compounds and antioxidant capacity. Wines were obtained from Boğazkere grape cultivar by techniques of classical maceration, cold maceration combined with ultraviolet light (UV) irradiation, and thermovinification combined with UV irradiation and changes in phenolic contents were examined. Total phenolic and anthocyanin contents and trolox equivalent antioxidant capacity of wines were measured spectrophotometrically and phenolic contents (+)-catechin, (-)-epicatechin, rutin, quercetin, trans-resveratrol, and cis-resveratrol were measured by High Pressure Liquid Chromatography with Diode Array Detection (HPLC-DAD). As a result of the study, the highest phenolic content except for quercetin was measured in the wines obtained by thermovinification combined with UV irradiation. We demonstrated that the highest phenolic compounds with health effect, total phenolic compounds, total anthocyanin, and antioxidant activity were obtained from thermovinification with UV-C treatment than classical wine making. © 2017 Institute of Food Technologists®.

The impact of drying techniques on phenolic compound, total phenolic content and antioxidant capacity of oat flour tarhana.

PubMed

Değirmencioğlu, Nurcan; Gürbüz, Ozan; Herken, Emine Nur; Yıldız, Aysun Yurdunuseven

2016-03-01

In this study, the changes in phenolic composition, total phenolic content, and antioxidant capacity of tarhanas supplemented with oat flour (OF) at the levels of 20-100% (w/w) after three drying treatments (sun-, oven-, and microwave drying) were investigated. A total of seventeen phenolic standards have been screened in tarhanas, and the most abundant flavonol and phenolic acid compounds were kaempferol (23.62mg/g) and 3-hydroxy-4-metoxy cinnamic acid (9.60mg/g). The total phenolic content amount gradually increased with the addition of OF to tarhana, but decidedly higher total phenolic content was found in samples oven dried at 55°C as compared with other methods. The microwave- and oven dried tarhana samples showed higher TEACDPPH and TEACABTS values than those dried with the other methods, respectively, in higher OF amounts. Consequently, oven- and microwave-drying can be recommended to retain the highest for phenolic compounds as well as maximal antioxidant capacity in OF supplemented tarhana samples. Copyright © 2015 Elsevier Ltd. All rights reserved.

Comprehensive Characterization of Extractable and Nonextractable Phenolic Compounds by High-Performance Liquid Chromatography-Electrospray Ionization-Quadrupole Time-of-Flight of a Grape/Pomegranate Pomace Dietary Supplement.

PubMed

Pérez-Ramírez, Iza F; Reynoso-Camacho, Rosalía; Saura-Calixto, Fulgencio; Pérez-Jiménez, Jara

2018-01-24

Grape and pomegranate are rich sources of phenolic compounds, and their derived products could be used as ingredients for the development of functional foods and dietary supplements. However, the profile of nonextractable or macromolecular phenolic compounds in these samples has not been evaluated. Here, we show a comprehensive characterization of extractable and nonextractable phenolic compounds of a grape/pomegranate pomace dietary supplement using high-performance liquid chromatography-electrospray ionization-quadrupole time-of-flight (HPLC-ESI-QTOF) and matrix-assisted laser desorption/ionization (MALDI)-TOF techniques. The main extractable phenolic compounds were several anthocyanins (principally malvidin 3-O-glucoside) as well as gallotannins and gallagyl derivatives; some phenolic compounds were reported in grape or pomegranate for the first time. Additionally, there was a high proportion of nonextractable phenolic compounds, including vanillic acid, and dihydroxybenzoic acid. Unidentified polymeric structures were detected by MALDI-TOF MS analysis. This study shows that mixed grape and pomegranate pomaces are a source of different classes of phenolic compounds including a high proportion of nonextractable phenolic compounds.

Biodegradation of Phenolic Contaminants: Current Status and Perspectives

NASA Astrophysics Data System (ADS)

Zhao, Lin; Wu, Qi; Ma, Aijin

2018-01-01

Phenolic compounds, a class of toxic pollutants in water, come mainly from a variety of industrial processes. The industrial application for biodegradation has become an important topic in recent years. In this review, we discuss the present situation, properties, and pollution characteristics of phenolic contaminants, factors affecting the degradation of phenols, microbial species and biodegradation methods. The challenges and opportunities in developing biodegradation processes of phenolic contaminants are also discussed.

U-Shape Suppressive Effect of Phenol Red on the Epileptiform Burst Activity via Activation of Estrogen Receptors in Primary Hippocampal Culture

PubMed Central

Liu, Xu; Chen, Ben; Chen, Lulan; Ren, Wan-Ting; Liu, Juan; Wang, Guoxiang; Fan, Wei; Wang, Xin; Wang, Yun

2013-01-01

Phenol red is widely used in cell culture as a pH indicator. Recently, it also has been reported to have estrogen-like bioactivity and be capable of promoting cell proliferation in different cell lines. However, the effect of phenol red on primary neuronal culture has never been investigated. By using patch clamp technique, we demonstrated that hippocampal pyramidal neurons cultured in neurobasal medium containing no phenol red had large depolarization-associated epileptiform bursting activities, which were rarely seen in neurons cultured in phenol red-containing medium. Further experiment data indicate that the suppressive effect of the phenol red on the abnormal epileptiform burst neuronal activities was U-shape dose related, with the most effective concentration at 28 µM. In addition, this concentration related inhibitory effect of phenol red on the epileptiform neuronal discharges was mimicked by 17-β-estradiol, an estrogen receptor agonist, and inhibited by ICI-182,780, an estrogen receptor antagonist. Our results suggest that estrogen receptor activation by phenol red in the culture medium prevents formation of abnormal, epileptiform burst activity. These studies highlight the importance of phenol red as estrogen receptor stimulator and cautions of careful use of phenol red in cell culture media. PMID:23560076

Breeding Vegetables with Increased Content in Bioactive Phenolic Acids.

PubMed

Kaushik, Prashant; Andújar, Isabel; Vilanova, Santiago; Plazas, Mariola; Gramazio, Pietro; Herraiz, Francisco Javier; Brar, Navjot Singh; Prohens, Jaime

2015-10-09

Vegetables represent a major source of phenolic acids, powerful antioxidants characterized by an organic carboxylic acid function and which present multiple properties beneficial for human health. In consequence, developing new varieties with enhanced content in phenolic acids is an increasingly important breeding objective. Major phenolic acids present in vegetables are derivatives of cinnamic acid and to a lesser extent of benzoic acid. A large diversity in phenolic acids content has been found among cultivars and wild relatives of many vegetable crops. Identification of sources of variation for phenolic acids content can be accomplished by screening germplasm collections, but also through morphological characteristics and origin, as well as by evaluating mutations in key genes. Gene action estimates together with relatively high values for heritability indicate that selection for enhanced phenolic acids content will be efficient. Modern genomics and biotechnological strategies, such as QTL detection, candidate genes approaches and genetic transformation, are powerful tools for identification of genomic regions and genes with a key role in accumulation of phenolic acids in vegetables. However, genetically increasing the content in phenolic acids may also affect other traits important for the success of a variety. We anticipate that the combination of conventional and modern strategies will facilitate the development of a new generation of vegetable varieties with enhanced content in phenolic acids.

[Role of NO signal in ABA-induced phenolic acids accumulation in Salvia miltiorrhiza hairy roots].

PubMed

Shen, Lihong; Ren, Jiahui; Jin, Wenfang; Wang, Ruijie; Ni, Chunhong; Tong, Mengjiao; Liang, Zongsuo; Yang, Dongfeng

2016-02-01

To investigate roles of nitric oxide (NO) signal in accumulations of phenolic acids in abscisic.acid (ABA)-induced Salvia miltiorrhiza hairy roots, S. miltiorrhiza hairy roots were treated with different concentrations of sodium nitroprusside (SNP)-an exogenous NO donor, for 6 days, and contents of phenolic acids in the hairy roots are determined. Then with treatment of ABA and NO scavenger (2-(4-carboxy-2-phenyl)-4,4,5,5-tetramethylimidazoline-1- oxyl-3-oxide, c-PTIO) or NO synthase inhibitor (NG-nitro-L-arginine methyl ester, L-NAME), contents of phenolic acids and expression levels of three key genes involved in phenolic acids biosynthesis were detected. Phenolic acids production in S. miltiorrhiza hairy roots was most significantly improved by 100 µmoL/L SNP. Contents of RA and salvianolic acid B increased by 3 and 4 folds. ABA significantly improved transcript levels of PAL (phenylalanine ammonia lyase), TAT (tyrosine aminotransferase) and RAS (rosmarinic acid synthase), and increased phenolic acids accumulations. However, with treatments of ABA+c-PTIO or ABA+L-NAME, accumulations of phenolic acids and expression levels of the three key genes were significantly inhibited. Both NO and ABA can increase accumulations of phenolic acids in S. miltiorrhiza hairy roots. NO signal probably mediates the ABA-induced phenolic acids production.

Changes of the phenolic compounds and antioxidant activities in germinated adlay seeds.

PubMed

Xu, Lei; Wang, Pei; Ali, Barkat; Yang, Na; Chen, Yisheng; Wu, Fengfeng; Xu, Xueming

2017-09-01

Over the years, germinated adlay products have been used as both food source and folk medicine. This study investigated the changes of total phenolic content (TPC), total flavonoid content (TFC), antioxidant activities, and phenolic acid profiles of adlay seed during germination. Results revealed that phenolic compounds and antioxidant activities varied with the germination stages. Germination significantly increased the free form phenolic and flavonoid contents by 112.5% and 168.3%, respectively. However, both of the bound form phenolic and flavonoid contents significantly decreased after germination. Phenolic acid compositions were quantified via HPLC analysis, and the levels of vanillic, p-coumaric, caffeic, hydroxybenzoic and protocatechuic acids in the free phenolic extracts were found to be significantly increased. The improvement of the free and total phenolic and flavonoid contents by the germination process led to a significant enhancement of the antioxidant activities (evaluated by the ABTS, FRAP and ORAC assays). The TPC showed the highest correlation with ORAC values (r = 0.9979). Germinated adlay had higher free and total phenolic and flavonoid contents, and antioxidant activities than ungerminated adlay. This study indicates that germinated adlay could be a promising functional food, more suitable for human consumption. © 2017 Society of Chemical Industry. © 2017 Society of Chemical Industry.

Peroxidase extraction from jicama skin peels for phenol removal

NASA Astrophysics Data System (ADS)

Chiong, T.; Lau, S. Y.; Khor, E. H.; Danquah, M. K.

2016-06-01

Phenol and its derivatives exist in various types of industrial effluents, and are known to be harmful to aquatic lives even at low concentrations. Conventional treatment technologies for phenol removal are challenged with long retention time, high energy consumption and process cost. Enzymatic treatment has emerged as an alternative technology for phenol removal from wastewater. These enzymes interact with aromatic compounds including phenols in the presence of hydrogen peroxide, forming free radicals which polymerize spontaneously to produce insoluble phenolic polymers. This work aims to extract peroxidase from agricultural wastes materials and establish its application for phenol removal. Peroxidase was extracted from jicama skin peels under varying extraction conditions of pH, sample-to-buffer ratio (w/v %) and temperature. Experimental results showed that extraction process conducted at pH 10, 40% w/v and 25oC demonstrated a peroxidase activity of 0.79 U/mL. Elevated temperatures slightly enhanced the peroxidase activities. Jicama peroxidase extracted at optimum extraction conditions demonstrated a phenol removal efficiency of 87.5% at pH 7. Phenol removal efficiency was ∼ 97% in the range of 30 - 40oC, and H2O2 dosage has to be kept below 100 mM for maximum removal under phenol concentration tested.

Biofilm coupled with UV irradiation for phenol degradation and change of its community structure.

PubMed

Xia, Siqing; Yan, Ning; Zhu, Jun; Zhang, Yongming

2011-06-01

The extensive use of phenol compounds and the inability to remove these compounds during wastewater treatment have resulted in the widespread occurrence of phenols in the natural environment. Phenols have been linked to serious risks to human and environmental health. Hence, the need to develop technologies that can effectively remove phenols from wastewater and source waters is a pressing challenge. In this study, light ceramic particles were immersed in activated sludge acclimated to degrade phenol, and microorganisms were allowed to attach to the particles surface to form biofilm. Then the ceramic particles with biofilm were moved into the photolytic circulating-bed biofilm reactor made of quartz glass, which was used for the degradation of phenol by three protocols: photolysis with UV light alone (P), biodegradation alone (B), and the two mechanisms operating simultaneously (photobiodegradation, P&B). The experimental results indicated that phenol removal rate was quickest by B experiment. However, P&B experiment gave more complete mineralization of phenol than that by other protocols. During P&B experiment, the microorganisms grown on porous ceramic carrier still kept the bioactivity degrading phenol, even under UV light irradiation. However, the dominant members of the bacterial community changed dramatically after the intimately coupled photobiodegradation, according to molecular biological analysis to the biofilm. Whereas Beijerinckia sp. was the dominant strain in the inoculum, it was replaced by Thauera sp. MZ1T that played a main role on degrading phenol during P&B experiment.

Phenolics content and antioxidant activity of tartary buckwheat from different locations.

PubMed

Guo, Xu-Dan; Ma, Yu-Jie; Parry, John; Gao, Jin-Ming; Yu, Liang-Li; Wang, Min

2011-11-25

Two tartary buckwheat samples (Xingku No.2 and Diqing) grown at three locations were analyzed for free and bound phenolic content and antioxidant properties. Moreover, the relative contributions of variety and growing environment to phenolic content and antioxidant properties were determined, as well as correlations of these properties to growing conditions. The total phenolic contents varied from 5,150 to 9,660 μmol of gallic acid equivalents per 100 gram of dry weight (DW) of tartary buckwheat and the free phenolics accounted for 94% to 99%. Rutin content was in the range from 518.54 to 1,447.87 mg per 100 gram of DW of tartary buckwheat. p-Hydroxybenzoic, ferulic and protocatechuic acids were the prominent phenolic acids and other phenolics, including p-coumaric, gallic, caffeic, vanillic and syringic acids were also detected. Tartary buckwheat exhibited higher DPPH· and ABTS·+ scavenging activities and was more effective at preventing the bleaching of β-carotene in comparison with reference antioxidant and plant phenolics constituents. Additionally, growing conditions and the interaction between variety and environment may have more contribution than variety to individual phenolics and antioxidant properties of tartary buckwheat. Environmental parameters such as higher altitudes may also have an increasing effect on rutin and phenolic acids. This study suggests that tartary buckwheat has potential health benefits because of its high phenolic content and antioxidant properties. These components could also be enhanced by optimizing the growing conditions of a selected variety.

Influence of rye flour enzymatic biotransformation on the antioxidant capacity and transepithelial transport of phenolic acids.

PubMed

de Lima, Fabíola Aliaga; Martins, Isabela Mateus; Faria, Ana; Calhau, Conceição; Azevedo, Joana; Fernandes, Iva; Mateus, Nuno; Macedo, Gabriela Alves

2018-03-01

Phenolic acids have been reported to play a role on the antioxidant activity and other important biological activities. However, as most polyphenolics in food products are either bound to cellular matrices or present as free polymeric forms, the way they are absorbed has not been totally clear until now. Hydrolytic enzymes may act to increase functionalities in polyphenolic-rich foods, enhancing the bioaccessibility of phenolic compounds and minerals from whole grains. The aim of this study was to evaluate the action of tannin acyl hydrolase (tannase) on the total phenols, phenolic acid profile, antioxidant capacity and in vitro bioaccessibility of phenolic acids found in whole rye flour (RF). Besides increasing total phenols and the antioxidant capacity, tannase treatment increased the amounts of ferulic, sinapic and vanillic acids identified in RF, evidencing a new type of feruloyl esterase catalytic action of tannase. Vanillic and sinapic acids in tannase-treated whole rye flour (RFT) were higher than RF after in vitro gastrointestinal digestion, and higher amounts of transported vanillic acid through the Caco-2 monolayer were detected in RFT. However, the bioaccessibility and the transport efficiency of RF phenolic acids were higher than RFT. Underutilized crops like rye and rye-derived products may be an important source of phenolic acids. The tannase biotransformation, even influencing the total phenolics and antioxidant capacity of RF, did not increase the bioaccessibility of phenolic acids under the experimental conditions of this study.

Impact of boiling on free and bound phenolic profile and antioxidant activity of commercial gluten-free pasta.

PubMed

Rocchetti, Gabriele; Lucini, Luigi; Chiodelli, Giulia; Giuberti, Gianluca; Montesano, Domenico; Masoero, Francesco; Trevisan, Marco

2017-10-01

Cooking by boiling dry pasta could have varying degrees of influence on nutritional and functional components. In the present study, its effect on total phenolic content and antioxidant capacity, as well as on the comprehensive profile of free and bound phenolics, was investigated in six commercial gluten-free (GF) pasta products. Overall, the heat treatment caused a significant reduction (P<0.01) of the total phenolic content as well as FRAP reducing power and ORAC radical scavenging, with significant differences among the pasta samples considered. The highest values were recorded in free phenolic fraction remaining in black rice (41mggallic acid equivalents100g -1 and 25mmolTrolox Equivalents100g -1 ) and quinoa (24mggallic acid equivalents100g -1 and 14mmolTrolox Equivalents100g -1 ) cooked GF pasta. Significant correlations (P<0.01) could be found between total phenolics and both the antioxidant capacity assays performed. UHPLC-ESI/QTOF-MS mass profiling allowed confirming the spectrophotometric results, while identifying the amount of free and bound fractions. Among phenolic classes, lignans exhibited the highest decrease during the cooking process, followed by stilbenes and flavonoids. However, phenolic acids and other phenolics showed the highest stability. Furthermore, cooking by boiling strongly lowered the bound-to-free ratio of phenolic compounds, by an averaged factor ranging from 14-folds for flavonoids to 5-folds for other classes of phenolics. Copyright © 2017 Elsevier Ltd. All rights reserved.

Process for preparing phenolic formaldehyde resole resin products derived from fractionated fast-pyrolysis oils

DOEpatents

Chum, Helena L.; Kreibich, Roland E.

1992-01-01

A process for preparing phenol-formaldehyde resole resins and adhesive compositions in which portions of the phenol normally contained in said resins are replaced by a phenol/neutral fractions extract obtained from fractionating fast-pyrolysis oils.

Enhancing charge storage of conjugated polymer electrodes with phenolic acids

NASA Astrophysics Data System (ADS)

Wagner, Michal; Rębiś, Tomasz; Inganäs, Olle

2016-01-01

We here present studies of electrochemical doping of poly(1-aminoanthraquinone) (PAAQ) films with three structurally different phenolic acids. The examined phenolic acids (sinapic, ferulic and syringic acid) were selected due to their resemblance to redox active groups, which can be found in lignin. The outstanding electrochemical stability of PAAQ films synthesized for this work enabled extensive cycling of phenolic acid-doped PAAQ films. Potentiodynamic and charge-discharge studies revealed that phenolic acid-doped PAAQ films exhibited enhanced capacitance in comparison to undoped PAAQ films, together with appearance of redox activity characteristics specific for each dopant. Electrochemical kinetic studies performed on microelectrodes affirmed the fast electron transfer for hydroquinone-to-quinone reactions with these phenolic compounds. These results imply the potential application of phenolic acids in cheap and degradable energy storage devices.

Efficacy of topical phenol decontamination strategies on severity of acute phenol chemical burns and dermal absorption: in vitro and in vivo studies in pig skin.

PubMed

Monteiro-Riviere, N A; Inman, A O; Jackson, H; Dunn, B; Dimond, S

2001-05-01

Pure phenol is colorless and used in the manufacture of phenolic resins, plastics, explosives, fertilizers, paints, rubber, textiles, adhesives, pharmaceuticals, paper, soap, and wood preservatives. The purpose of this study was to compare the efficacy of several phenol decontamination strategies following dermal exposure using the pig as a model for human exposure, and then assess the effect of the two best treatments on phenol absorption in the isolated perfused porcine skin flap (IPPSF). Six anesthetized Yorkshire pigs were exposed to 89% aqueous phenol for 1 min using Hilltop chambers (10 skin sites/pig; 400 microl/site). Exposure to phenol was followed by one of 10 different decontamination procedures: 1-, 5-, 15-, and 30-min water wash; Ivory soap solution; polyethylene glycol (PEG 400); PEG 400/industrial methylated spirits (IMS); PEG 400/ethanol (EtOH); polyvinyl pyrrolidone (PVP)/70% isopropanol (IPA); and 70% IPA. For each of the last five strategies, 1-min treatment washes were repeatedly alternated with 1-min water washes for a total of 15 min. Evaluation was based on scoring of erythema, edema, and histological parameters such as intracellular and intercellular epidermal edema, papillary dermal edema, perivascular infiltrates, pyknotic stratum basale cells, and epidermal-dermal separation. It was concluded that PEG 400 and 70% IPA were superior to the other treatments investigated and equally efficacious in the reduction of phenol-induced skin damage. In addition, phenol absorption was assessed utilizing the two most effective in vivo treatments in the IPPSF. The assessment of percutaneous absorption of phenol found the PEG 400, 70% IPA, and 15-min water treatments significantly (P < 0.05) reduced phenol absorption relative to no treatment.

Comparison of antioxidant activity, anthocyanins, carotenoids, and phenolics of three native fresh and sun-dried date (Phoenix dactylifera L.) varieties grown in Oman.

PubMed

Al-Farsi, Mohamed; Alasalvar, Cesarettin; Morris, Anne; Baron, Mark; Shahidi, Fereidoon

2005-09-21

Fresh and sun-dried dates of three native varieties from Oman, namely, Fard, Khasab, and Khalas, were examined for their antioxidant activity and total contents of anthocyanins, carotenoids, and phenolics, as well as free and bound phenolic acids. All results are expressed as mean value +/- standard deviation (n = 3) on a fresh weight basis. Fresh date varieties were found to be a good source of antioxidants (11687-20604 micromol of Trolox equiv/g), total contents of anthocyanins (0.24-1.52 mg of cyanidin 3-glucoside equiv/100 g), carotenoids (1.31-3.03 mg/100 g), phenolics (134-280 mg of ferulic acid equiv/100 g), free phenolic acids (2.61-12.27 mg/100 g), and bound phenolic acids (6.84-30.25 mg/100 g). A significant (p < 0.05) amount of antioxidants and carotenoids was lost after sun-drying of dates, whereas the total content of phenolics and free and bound phenolic acids increased significantly (p < 0.05). Anthocyanins were detected only in fresh dates. Date varieties had different levels and patterns of phenolic acids. Four free phenolic acids (protocatechuic acid, vanillic acid, syringic acid, and ferulic acid) and nine bound phenolic acids (gallic acid, protocatechuic acid, p-hydroxybenzoic acid, vanillic acid, caffeic acid, syringic acid, p-coumaric acid, ferulic acid, and o-coumaric acid) were tentatively identified. Of the date varieties studied, Khalas, which is considered to be premium quality, had higher antioxidant activity, total carotenoids, and bound phenolic acids than other varieties. These results suggest that all date varieties serve as a good source of natural antioxidants and could potentially be considered as a functional food or functional food ingredient, although some of their antioxidant constituents are lost during sun-drying.

From Olive Fruits to Olive Oil: Phenolic Compound Transfer in Six Different Olive Cultivars Grown under the Same Agronomical Conditions.

PubMed

Talhaoui, Nassima; Gómez-Caravaca, Ana María; León, Lorenzo; De la Rosa, Raúl; Fernández-Gutiérrez, Alberto; Segura-Carretero, Antonio

2016-03-04

Phenolic compounds are responsible of the nutritional and sensory quality of extra-virgin olive oil (EVOO). The composition of phenolic compounds in EVOO is related to the initial content of phenolic compounds in the olive-fruit tissues and the activity of enzymes acting on these compounds during the industrial process to produce the oil. In this work, the phenolic composition was studied in six major cultivars grown in the same orchard under the same agronomical and environmental conditions in an effort to test the effects of cultivars on phenolic composition in fruits and oils as well as on transfer between matrices. The phenolic fractions were identified and quantified using high-performance liquid chromatography-diode array detector-time-of-flight-mass spectrometry. A total of 33 phenolic compounds were determined in the fruit samples and a total of 20 compounds in their corresponding oils. Qualitative and quantitative differences in phenolic composition were found among cultivars in both matrices, as well as regarding the transfer rate of phenolic compounds from fruits to oil. The results also varied according to the different phenolic groups evaluated, with secoiridoids registering the highest transfer rates from fruits to oils. Moreover, wide-ranging differences have been noticed between cultivars for the transfer rates of secoiridoids (4.36%-65.63% of total transfer rate) and for flavonoids (0.18%-0.67% of total transfer rate). 'Picual' was the cultivar that transferred secoiridoids to oil at the highest rate, whereas 'Changlot Real' was the cultivar that transferred flavonoids at the highest rates instead. Principal-component analysis confirmed a strong genetic effect on the basis of the phenolic profile both in the olive fruits and in the oils.

Demonstration of x-ray fluorescence imaging of a high-energy-density plasma.

PubMed

MacDonald, M J; Keiter, P A; Montgomery, D S; Biener, M M; Fein, J R; Fournier, K B; Gamboa, E J; Klein, S R; Kuranz, C C; LeFevre, H J; Manuel, M J-E; Streit, J; Wan, W C; Drake, R P

2014-11-01

Experiments at the Trident Laser Facility have successfully demonstrated the use of x-ray fluorescence imaging (XRFI) to diagnose shocked carbonized resorcinol formaldehyde (CRF) foams doped with Ti. One laser beam created a shock wave in the doped foam. A second laser beam produced a flux of vanadium He-α x-rays, which in turn induced Ti K-shell fluorescence within the foam. Spectrally resolved 1D imaging of the x-ray fluorescence provided shock location and compression measurements. Additionally, experiments using a collimator demonstrated that one can probe specific regions within a target. These results show that XRFI is a capable alternative to path-integrated measurements for diagnosing hydrodynamic experiments at high energy density.

Data for the synthesis of resorcinol-formaldehyde aerogels in acidic and basic media.

PubMed

Molina-Campos, Daniel F; Fonseca-Correa, Rafael A; Vargas-Delgadillo, Diana P; Giraldo, Liliana; Moreno-Piraján, Juan Carlos

2017-06-01

The aim of this research is to synthesise carbon aerogels and to compare the differences in their textural, morphological and chemical properties when synthesised in basic and acidic media, and with two different types of pretreatment carbonization and activation with CO 2 . Four samples are prepared and characterised using TGA-DTA, SEM, DRX, isotherm determination of N 2 adsorption-desorption at -196 °C and immersion calorimetry. The data for pore distribution are reported using non-local density functional theory and quenched solid density functional theory. Finally, with the immersion calorimetry data, the consistency between the results using this technique and those obtained using the nitrogen isotherms is analysed.

Antioxidative properties of hydroxycinnamic acid derivatives and a phenylpropanoid glycoside. A pulse radiolysis study

NASA Astrophysics Data System (ADS)

Lin, Weizhen; Navaratnam, Suppiah; Yao, Side; Lin, Nianyun

1998-10-01

Spectral and redox properties of the phenoxyl radicals from hydroxycinnamic acid derivatives and one selected component of phenylpropanoid glycosides, verbascoside, were studied using pulse radiolysis techniques. On the basis of the pH dependence of phenoxyl radical absorptions, the p Ka values for deprotonation of sinapic acid radical and ferulic acid radical are 4.9 and 5.2. The rate constants of one electron oxidation of those antioxidants by azide radical and bromide radical ion were determined at pH 7. The redox potentials of those antioxidants were determined as 0.59-0.71 V vs NHE at pH 7 with reference standard 4-methoxyphenol and resorcinol.

Infrared spectroscopy of copper-resveratrol complexes: A joint experimental and theoretical study

NASA Astrophysics Data System (ADS)

Chiavarino, B.; Crestoni, M. E.; Fornarini, S.; Taioli, S.; Mancini, I.; Tosi, P.

2012-07-01

Infrared multiple-photon dissociation spectroscopy has been used to record vibrational spectra of charged copper-resveratrol complexes in the 3500-3700 cm-1 and 1100-1900 cm-1 regions. Minimum energy structures have been determined by density functional theory calculations using plane waves and pseudopotentials. In particular, the copper(I)-resveratrol complex presents a tetra-coordinated metal bound with two carbon atoms of the alkenyl moiety and two closest carbons of the adjoining resorcinol ring. For these geometries vibrational spectra have been calculated by using linear response theory. The good agreement between experimental and calculated IR spectra for the selected species confirms the overall reliability of the proposed geometries.

Changes in Phenolic Acid Content in Maize during Food Product Processing.

PubMed

Butts-Wilmsmeyer, Carrie J; Mumm, Rita H; Rausch, Kent D; Kandhola, Gurshagan; Yana, Nicole A; Happ, Mary M; Ostezan, Alexandra; Wasmund, Matthew; Bohn, Martin O

2018-04-04

The notion that many nutrients and beneficial phytochemicals in maize are lost due to food product processing is common, but this has not been studied in detail for the phenolic acids. Information regarding changes in phenolic acid content throughout processing is highly valuable because some phenolic acids are chemopreventive agents of aging-related diseases. It is unknown when and why these changes in phenolic acid content might occur during processing, whether some maize genotypes might be more resistant to processing induced changes in phenolic acid content than other genotypes, or if processing affects the bioavailability of phenolic acids in maize-based food products. For this study, a laboratory-scale processing protocol was developed and used to process whole maize kernels into toasted cornflakes. High-throughput microscale wet-lab analyses were applied to determine the concentrations of soluble and insoluble-bound phenolic acids in samples of grain, three intermediate processing stages, and toasted cornflakes obtained from 12 ex-PVP maize inbreds and seven hybrids. In the grain, insoluble-bound ferulic acid was the most common phenolic acid, followed by insoluble-bound p-coumaric acid and soluble cinnamic acid, a precursor to the phenolic acids. Notably, the ferulic acid content was approximately 1950 μg/g, more than ten-times the concentration of many fruits and vegetables. Processing reduced the content of the phenolic acids regardless of the genotype. Most changes occurred during dry milling due to the removal of the bran. The concentration of bioavailable soluble ferulic and p-coumaric acid increased negligibly due to thermal stresses. Therefore, the current dry milling based processing techniques used to manufacture many maize-based foods, including breakfast cereals, are not conducive for increasing the content of bioavailable phenolics in processed maize food products. This suggests that while maize is an excellent source of phenolics, alternative or complementary processing methods must be developed before this nutritional resource can be utilized.

Fruit Phenolic Profiling: A New Selection Criterion in Olive Breeding Programs

PubMed Central

Pérez, Ana G.; León, Lorenzo; Sanz, Carlos; de la Rosa, Raúl

2018-01-01

Olive growing is mainly based on traditional varieties selected by the growers across the centuries. The few attempts so far reported to obtain new varieties by systematic breeding have been mainly focused on improving the olive adaptation to different growing systems, the productivity and the oil content. However, the improvement of oil quality has rarely been considered as selection criterion and only in the latter stages of the breeding programs. Due to their health promoting and organoleptic properties, phenolic compounds are one of the most important quality markers for Virgin olive oil (VOO) although they are not commonly used as quality traits in olive breeding programs. This is mainly due to the difficulties for evaluating oil phenolic composition in large number of samples and the limited knowledge on the genetic and environmental factors that may influence phenolic composition. In the present work, we propose a high throughput methodology to include the phenolic composition as a selection criterion in olive breeding programs. For that purpose, the phenolic profile has been determined in fruits and oils of several breeding selections and two varieties (“Picual” and “Arbequina”) used as control. The effect of three different environments, typical for olive growing in Andalusia, Southern Spain, was also evaluated. A high genetic effect was observed on both fruit and oil phenolic profile. In particular, the breeding selection UCI2-68 showed an optimum phenolic profile, which sums up to a good agronomic performance previously reported. A high correlation was found between fruit and oil total phenolic content as well as some individual phenols from the two different matrices. The environmental effect on phenolic compounds was also significant in both fruit and oil, although the low genotype × environment interaction allowed similar ranking of genotypes on the different environments. In summary, the high genotypic variance and the simplified procedure of the proposed methodology for fruit phenol evaluation seems to be convenient for breeding programs aiming at obtaining new cultivars with improved phenolic profile. PMID:29535752

Fruit Phenolic Profiling: A New Selection Criterion in Olive Breeding Programs.

PubMed

Pérez, Ana G; León, Lorenzo; Sanz, Carlos; de la Rosa, Raúl

2018-01-01

Olive growing is mainly based on traditional varieties selected by the growers across the centuries. The few attempts so far reported to obtain new varieties by systematic breeding have been mainly focused on improving the olive adaptation to different growing systems, the productivity and the oil content. However, the improvement of oil quality has rarely been considered as selection criterion and only in the latter stages of the breeding programs. Due to their health promoting and organoleptic properties, phenolic compounds are one of the most important quality markers for Virgin olive oil (VOO) although they are not commonly used as quality traits in olive breeding programs. This is mainly due to the difficulties for evaluating oil phenolic composition in large number of samples and the limited knowledge on the genetic and environmental factors that may influence phenolic composition. In the present work, we propose a high throughput methodology to include the phenolic composition as a selection criterion in olive breeding programs. For that purpose, the phenolic profile has been determined in fruits and oils of several breeding selections and two varieties ("Picual" and "Arbequina") used as control. The effect of three different environments, typical for olive growing in Andalusia, Southern Spain, was also evaluated. A high genetic effect was observed on both fruit and oil phenolic profile. In particular, the breeding selection UCI2-68 showed an optimum phenolic profile, which sums up to a good agronomic performance previously reported. A high correlation was found between fruit and oil total phenolic content as well as some individual phenols from the two different matrices. The environmental effect on phenolic compounds was also significant in both fruit and oil, although the low genotype × environment interaction allowed similar ranking of genotypes on the different environments. In summary, the high genotypic variance and the simplified procedure of the proposed methodology for fruit phenol evaluation seems to be convenient for breeding programs aiming at obtaining new cultivars with improved phenolic profile.

Complex enzyme hydrolysis releases antioxidative phenolics from rice bran.

PubMed

Liu, Lei; Wen, Wei; Zhang, Ruifen; Wei, Zhencheng; Deng, Yuanyuan; Xiao, Juan; Zhang, Mingwei

2017-01-01

In this study, phenolic profiles and antioxidant activity of rice bran were analyzed following successive treatment by gelatinization, liquefaction and complex enzyme hydrolysis. Compared with gelatinization alone, liquefaction slightly increased the total amount of phenolics and antioxidant activity as measured by ferric reducing antioxidant power (FRAP) and oxygen radical absorbance capacity (ORAC) assays. Complex enzyme hydrolysis significantly increased the total phenolics, flavonoids, FRAP and ORAC by 46.24%, 79.13%, 159.14% and 41.98%, respectively, compared to gelatinization alone. Furthermore, ten individual phenolics present in free or soluble conjugate forms were also analyzed following enzymatic processing. Ferulic acid experienced the largest release, followed by protocatechuic acid and then quercetin. Interestingly, a major proportion of phenolics existed as soluble conjugates, rather than free form. Overall, complex enzyme hydrolysis releases phenolics, thus increasing the antioxidant activity of rice bran extract. This study provides useful information for processing rice bran into functional beverage rich in phenolics. Copyright © 2016 Elsevier Ltd. All rights reserved.

Structural Analysis of the Phenol-Responsive Sensory Domain of the Transcription Activator PoxR.

PubMed

Patil, Vinod Vikas; Park, Kwang-Hyun; Lee, Seung-Goo; Woo, Euijeon

2016-04-05

Positive phenol-degradative gene regulator (PoxR) is a σ(54)-dependent AAA+ ATPase transcription activator that regulates the catabolism of phenols. The PoxR sensory domain detects phenols and relays signals for the activation of transcription. Here we report the first structure of the phenol sensory domain bound to phenol and five derivatives. It exists as a tightly intertwined homodimer with a phenol-binding pocket buried inside, placing two C termini on the same side of the dimer. His102 and Trp130 interact with the hydroxyl group of the phenol in a cavity surrounded by rigid hydrophobic residues on one side and a flexible region on the other. Each monomer has a V4R fold with a unique zinc-binding site. A shift at the C-terminal helix suggests that there is a possible conformational change upon ligand binding. The results provide a structural basis of chemical effector binding for transcriptional regulation with broad implications for protein engineering. Copyright © 2016 Elsevier Ltd. All rights reserved.

ODC-Free Solvent Implementation for Phenolics Cleaning

NASA Technical Reports Server (NTRS)

Wurth, Laura; Biegert, Lydia; Lamont, DT; McCool, Alex (Technical Monitor)

2001-01-01

During phenolic liner manufacture, resin-impregnated (pre-preg) bias tape of silica, glass, or carbon cloth is tape-wrapped, cured, machined, and then wiped with 1,1,1 tri-chloroethane (TCA) to remove contaminants that may have been introduced during machining and handling. Following the TCA wipe, the machined surface is given a resin wet-coat and over-wrapped with more prepreg and cured. A TCA replacement solvent for these wiping operations must effectively remove both surface contaminants, and sub-surface oils and greases while not compromising the integrity of this interface. Selection of a TCA replacement solvent for phenolic over-wrap interface cleaning began with sub-scale compatibility tests with cured phenolics. Additional compatibility tests included assessment of solvent retention in machined phenolic surfaces. Results from these tests showed that, while the candidate solvent did not degrade the cured phenolics, it was retained in higher concentrations than TCA in phenolic surfaces. This effect was most pronounced with glass and silica cloth phenolics with steep ply angles relative to the wiped surfaces.

Synthesis, characterization, bioactivity and potential application of phenolic acid grafted chitosan: A review.

PubMed

Liu, Jun; Pu, Huimin; Liu, Shuang; Kan, Juan; Jin, Changhai

2017-10-15

In recent years, increasing attention has been paid to the grafting of phenolic acid onto chitosan in order to enhance the bioactivity and widen the application of chitosan. Here, we present a comprehensive overview on the recent advances of phenolic acid grafted chitosan (phenolic acid-g-chitosan) in many aspects, including the synthetic method, structural characterization, biological activity, physicochemical property and potential application. In general, four kinds of techniques including carbodiimide based coupling, enzyme catalyzed grafting, free radical mediated grafting and electrochemical methods are frequently used for the synthesis of phenolic acid-g-chitosan. The structural characterization of phenolic acid-g-chitosan can be determined by several instrumental methods. The physicochemical properties of chitosan are greatly altered after grafting. As compared with chitosan, phenolic acid-g-chitosan exhibits enhanced antioxidant, antimicrobial, antitumor, anti-allergic, anti-inflammatory, anti-diabetic and acetylcholinesterase inhibitory activities. Notably, phenolic acid-g-chitosan shows potential applications in many fields as coating agent, packing material, encapsulation agent and bioadsorbent. Copyright © 2017 Elsevier Ltd. All rights reserved.

LC-MS analysis of phenolic compounds and antioxidant activity of buckwheat at different stages of malting.

PubMed

Terpinc, Petra; Cigić, Blaž; Polak, Tomaž; Hribar, Janez; Požrl, Tomaž

2016-11-01

The impact of malting on the profile of the phenolic compounds and the antioxidant properties of two buckwheat varieties was investigated. The highest relative increases in phenolic compounds were observed for isoorientin, orientin, and isovitexin, which are consequently major inducible phenolic compounds during malting. Only a minor relative increase was observed for the most abundant phenolic compound, rutin. The radical-scavenging activity of buckwheat seeds was evaluated using ABTS and DPPH assays. A considerable increase in total phenolic compounds and higher antioxidant activity were observed after 64h of germination, whereas kilning resulted in decreased total phenolic compounds and antioxidant activity. Higher antioxidant activities for extracts were found for buffered solvents than for pure methanol and water. Changes in the composition of the phenolic compounds and increased antioxidant content were confirmed by several methods, indicating that buckwheat malt can be used as a food rich in antioxidants. Copyright © 2016 Elsevier Ltd. All rights reserved.

Effects of different cellulases on the release of phenolic acids from rice straw during saccharification.

PubMed

Xue, Yiyun; Wang, Xiahui; Chen, Xingxuan; Hu, Jiajun; Gao, Min-Tian; Li, Jixiang

2017-06-01

Effects of different cellulases on the release of phenolic acids from rice straw during saccharification were investigated in this study. All cellulases tested increased the contents of phenolic acids during saccharification. However, few free phenolic acids were detected, as they were present in conjugated form after saccharification when the cellulases from Trichoderma reesei, Trichoderma viride and Aspergillus niger were used. On the other hand, phenolic acids were present in free form when the Acremonium cellulolyticus cellulase was used. Assays of enzyme activity showed that, besides high cellulase activity, the A. cellulolyticus cellulase exhibited high feruloyl esterase (FAE) activity. A synergistic interaction between FAE and cellulase led to the increase in free phenolic acids, and thus an increase in antioxidative and antiradical activities of the phenolic acids. Moreover, a cost estimation demonstrated the feasibility of phenolic acids as value-added products to reduce the total production cost of ethanol. Copyright © 2017 Elsevier Ltd. All rights reserved.

Solid state fermentation of Trichoderma viride for enhancement phenolic content, antioxidant and antimicrobial activities in ginger.

PubMed

Saleh, Rashad M; Kabli, Saleh A; Al-Garni, Saleh M; Al-Ghamdi, Maryam A; Abdel-Aty, Azza M; Mohamed, Saleh A

2018-05-04

The phenolic content of methanolic and water extracts of ginger fermented by Trichoderma spp. during solid state fermentation (SSF) was detected as compared with unfermented ginger. The total phenolic content of fermented ginger increased several times. The highest phenolic content of ginger was detected after SSF by T. viride. The optimal physiological conditions for the maximum production of the phenolic content and β-glucosidase activity of fermented ginger by T. viride were detected at day 7 incubation, pH 6.0, 30°C and 30% moisture. There are consistent between the maximum production of β-glucosidase and phenolic content. The SSF of ginger by T. viride greatly enhanced the antioxidant potency of phenolic compounds by using DPPH and ABTS assays. Potent antibacterial activity was appeared by phenolic compounds of fermented ginger against all the tested human-pathogenic bacteria. This article is protected by copyright. All rights reserved. This article is protected by copyright. All rights reserved.

Phenolic content and antioxidant and antimutagenic activities in tomato peel, seeds, and byproducts.

PubMed

Valdez-Morales, Maribel; Espinosa-Alonso, Laura Gabriela; Espinoza-Torres, Libia Citlali; Delgado-Vargas, Francisco; Medina-Godoy, Sergio

2014-06-11

The phenolic content and antioxidant and antimutagenic activities from the peel and seeds of different tomato types (grape, cherry, bola and saladette type), and simulated tomato industrial byproducts, were studied. Methanolic extracts were used to quantify total phenolic content, groups of phenolic compounds, antioxidant activities, and the profile of phenolic compounds (by HPLC-DAD). Antimutagenic activity was determined by Salmonella typhimurium assay. The total phenolic content and antioxidant activity of tomato and tomato byproducts were comparable or superior to those previously reported for whole fruit and tomato pomace. Phenolic compounds with important biological activities, such as caffeic acid, ferulic acid, chlorogenic acids, quercetin-3-β-O-glycoside, and quercetin, were quantified. Differences in all phenolic determinations due to tomato type and part of the fruit analyzed were observed, peel from grape type showing the best results. Positive antimutagenic results were observed in all samples. All evaluated materials could be used as a source of potential nutraceutical compounds.

Phenolic profile and effect of growing area on Pistacia lentiscus seed oil.

PubMed

Mezni, Faten; Slama, Awatef; Ksouri, Riadh; Hamdaoui, Ghaith; Khouja, Mohamed Larbi; Khaldi, Abdelhamid

2018-08-15

In this investigation, we aimed to study, for the first time, the phenolic composition of Pistacia lentiscus seed oils from different growing areas. Extraction of the phenolic fraction from oils was done by methanol/water. Phenolic profiles were determined using chromatographic analysis by High Performance Liquid Chromatography (HPLC-DAD/MSD) and its quantification was done using an internal standard which is unidentified in the studied oil (syringic acid). Forty phenolic compounds were quantified and only eighteen of them were identified. The eight studied oils showed different phenolic profiles. The total phenols amount varied from 538.03 mg/kg oil in Jbel Masour oils to 4260.57 mg/kg oil in oils from Kef Erraai. The highest amount of secoiridoids was reached by Bouchoucha oil containing 366.71 mg/kg oil of Oleuropein aglycon. Oils from Kef Erraai locality contained the highest concentrations in flavonols (377.44 mg/kg oil) and in phenolic acids (2762.67 mg/kg oil). Copyright © 2018 Elsevier Ltd. All rights reserved.

Determination of the major phenolic compounds in pomegranate juices by HPLC−DAD−ESI-MS.

PubMed

Gómez-Caravaca, Ana María; Verardo, Vito; Toselli, Moreno; Segura-Carretero, Antonio; Fernández-Gutiérrez, Alberto; Caboni, Maria Fiorenza

2013-06-05

Traditionally, pomegranate (Punica granatum L.) has been consumed as fresh fruit or as pomegranate juice. In this study, the main phenolic compounds of 12 pomegranate varieties and 5 pomegranate clones were determined by HPLC−DAD−ESI-MS. Two chromatographic methods with a fused-core C18 column and a classical HPLC system were developed. Thirteen anthocyanins and fourteen other phenolic compounds were determined in the pomegranate juices. As far as we are concerned, a new flavonol-glycoside, phellatin or its isomer amurensin, has been tentatively identified for the first time in pomegranate juices. Total phenolic content ranged from 580.8 to 2551.3 mg/L of pomegranate juice. Anthocyanins varied between 20 to 82% of total phenolic content. Flavonoids were 1.6-23.6% of total phenolic compounds, while phenolic acids and ellagitannins were in the range 16.4-65.8%. The five clones reported a phenolic content comparable with that of the other pomegranate samples.

Factors Affecting Selectivity of Brilliant Green-Phenol Red Agar for Salmonellae

PubMed Central

Moats, W. A.; Kinner, J. A.

1974-01-01

Commercial brilliant green (BG)-sulfa agar was found to be nonselective toward a test series of Enterobacteriaceae. Various formulations of BG were prepared by using Trypticase soy agar (BBL) as a base. Results were more reproducible when BG dye was added after sterilization than before. Sulfonamides improved selectivity as compared with brilliant green alone. Sulfanilamide (SN) was slightly more selective for salmonellae than other sulfonamides tested. Bile salts and sodium dodecyl sulfate markedly reduced the toxicity of BG to all the test bacteria. Enterobacter strains were most difficult to inhibit. A combination of 5 mg of BG and 1 g of SN/liter prevented growth of Proteus mirabilis and Escherichia coli and retarded growth of Enterobacter strains. The BG-SN agars were superior in selectivity to a series of commercial agars tested, and numbers of salmonellae recovered on BG-SN agar and Trypticase soy agar (BBL) were the same. Brilliant green agars with various degrees of selectivity are described. PMID:4589120

Synthesis and antiangiogenic activity study of new hop chalcone Xanthohumol analogues.

PubMed

Nuti, Elisa; Bassani, Barbara; Camodeca, Caterina; Rosalia, Lea; Cantelmo, AnnaRita; Gallo, Cristina; Baci, Denisa; Bruno, Antonino; Orlandini, Elisabetta; Nencetti, Susanna; Noonan, Douglas M; Albini, Adriana; Rossello, Armando

2017-09-29

Angiogenesis induction is a hallmark of cancer. Antiangiogenic properties of Xanthohumol (XN), a naturally occurring prenylated chalcone from hops, have been widely reported. Here we describe the synthesis and study the antiangiogenic activity in vitro of a series of XN derivatives, where different substituents on the B-ring of the chalcone scaffold were inserted. The new XN derivatives inhibited human umbilical-vein endothelial cell (HUVEC) proliferation, adhesion, migration, invasion and their ability to form capillary-like structures in vitro at 10 μM concentration. The preliminary results indicate that the phenolic OH group in R, present in natural XN, is not necessary for having antiangiogenic activity. In fact, the most effective compound from this series, 13, was characterized by a para-methoxy group in R and a fluorine atom in R 2 on B-ring. This study paves the way for future development of synthetic analogues of XN to be used as cancer angiopreventive and chemopreventive agents. Copyright © 2017 Elsevier Masson SAS. All rights reserved.

Physiological and functional diversity of phenol degraders isolated from phenol-grown aerobic granules: Phenol degradation kinetics and trichloroethylene co-metabolic activities.

PubMed

Zhang, Yi; Tay, Joo Hwa

2016-03-15

Aerobic granule is a novel form of microbial aggregate capable of degrading toxic and recalcitrant substances. Aerobic granules have been formed on phenol as the growth substrate, and used to co-metabolically degrade trichloroethylene (TCE), a synthetic solvent not supporting aerobic microbial growth. Granule formation process, rate limiting factors and the comprehensive toxic effects of phenol and TCE had been systematically studied. To further explore their potential at the level of microbial population and functions, phenol degraders were isolated and purified from mature granules in this study. Phenol and TCE degradation kinetics of 15 strains were determined, together with their TCE transformation capacities and other physiological characteristics. Isolation in the presence of phenol and TCE exerted stress on microbial populations, but the procedure was able to preserve their diversity. Wide variation was found with the isolates' kinetic behaviors, with the parameters often spanning 3 orders of magnitude. Haldane kinetics described phenol degradation well, and the isolates exhibited actual maximum phenol-dependent oxygen utilization rates of 9-449 mg DO g DW(-1) h(-1), in phenol concentration range of 4.8-406 mg L(-1). Both Michaelis-Menten and Haldane types were observed for TCE transformation, with the actual maximum rate of 1.04-21.1 mg TCE g DW(-1) h(-1) occurring between TCE concentrations of 0.42-4.90 mg L(-1). The TCE transformation capacities and growth yields on phenol ranged from 20-115 mg TCE g DW(-1) and 0.46-1.22 g DW g phenol(-1), respectively, resulting in TCE transformation yields of 10-70 mg TCE g phenol(-1). Contact angles of the isolates were between 34° and 82°, suggesting both hydrophobic and hydrophilic cell surface. The diversity in the isolates is a great advantage, as it enables granules to be versatile and adaptive under different operational conditions. Copyright © 2015 Elsevier Ltd. All rights reserved.

Verification of the electron/proton coupled mechanism for phenolic H-atom transfer using a triplet π,π ∗ carbonyl

NASA Astrophysics Data System (ADS)

Yamaji, Minoru; Oshima, Juro; Hidaka, Motohiko

2009-06-01

Evidence for the coupled electron/proton transfer mechanism of the phenolic H-atom transfer between triplet π,π ∗ 3,3'-carbonylbis(7-diethylaminocoumarin) and phenol derivatives is obtained by using laser photolysis techniques. It was confirmed that the quenching rate constants of triplet CBC by phenols having positive Hammett constants do not follow the Rehm-Weller equation for electron transfer while those by phenols with negative Hammett constants do it. From the viewpoint of thermodynamic parameters for electron transfer, the crucial factors for phenolic H-atom transfer to π,π ∗ triplet are discussed.

Inhibitory effects of benzimidazole containing new phenolic Mannich bases on human carbonic anhydrase isoforms hCA I and II.

PubMed

Gul, Halise Inci; Yazici, Zehra; Tanc, Muhammet; Supuran, Claudiu T

2016-12-01

New phenolic mono and bis Mannich bases incorporating benzimidazole, such as 2-(aminomethyl)-4-(1H-benzimidazol-2-yl)phenol and 2,6-bis(aminomethyl)-4-(1H-benzimidazol-2-yl)phenol were synthesized starting from 4-(1H-benzimidazol-2-yl)phenol. Amines used for the synthesis included dimethylamine, pyrrolidine, piperidine, N-methylpiperazine and morpholine. The CA inhibitory properties of these compounds were tested on the human carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I and hCA II. These new compounds, as many phenols show moderate CA inhibitory properties.

Antibacterial activity of sphagnum acid and other phenolic compounds found in Sphagnum papillosum against food-borne bacteria.

PubMed

Mellegård, H; Stalheim, T; Hormazabal, V; Granum, P E; Hardy, S P

2009-07-01

To identify the phenolic compounds in the leaves of Sphagnum papillosum and examine their antibacterial activity at pH appropriate for the undissociated forms. Bacterial counts of overnight cultures showed that whilst growth of Staphylococcus aureus 50084 was impaired in the presence of milled leaves, the phenol-free fraction of holocellulose of S. papillosum had no bacteriostatic effect. Liquid chromatography-mass spectrometry analysis of an acetone-methanol extract of the leaves detected eight phenolic compounds. Antibacterial activity of the four dominating phenols specific to Sphagnum leaves, when assessed in vitro as minimal inhibitory concentrations (MICs), were generally >2.5 mg ml(-1). MIC values of the Sphagnum-specific compound 'sphagnum acid' [p-hydroxy-beta-(carboxymethyl)-cinnamic acid] were >5 mg ml(-1). No synergistic or antagonistic effects of the four dominating phenols were detected in plate assays. Sphagnum-derived phenolics exhibit antibacterial activity in vitro only at concentrations far in excess of those found in the leaves. We have both identified the phenolic compounds in S. papillosum and assessed their antibacterial activity. Our data indicate that phenolic compounds in isolation are not potent antibacterial agents and we question their potency against food-borne pathogens.

Effect of nutrients on Chlorella pyrenoidosa for treatment of phenolic effluent of coal gasification plant.

PubMed

Stephen, Dayana Priyadharshini; Ayalur, Bakthavatsalam Kannappan

2017-05-01

The ability of Chlorella pyrenoidosa, a freshwater microalga, to degrade phenolic effluent of coal-based producer gas plant under ambient conditions was investigated. C. pyrenoidosa was able to grow in high-strength phenolic effluent. Major contaminant present in the effluent was phenol (C 6 H 5 OH). The effluent has 1475.3 ± 68 mg/L of initial total phenolic concentration. The effect of nutrients used for algal cultivation in phenol degradation was analyzed by inoculating four different concentrations, viz.,1, 2, 3, and 4 g of wet biomass/L of raw effluent of C. pyrenoidosa mixed with effluent into two batches (with and without nutrients). C. pyrenoidosa was able to degrade more than 95% of the phenol (C 6 H 5 OH) concentration with the algal concentrations of 3 and 4 g/L when supplemented with nutrients. With effluent devoid of nutrients, the average percent reduction in total phenolic compounds was observed to a maximum of 46%. No physical changes in the C. pyrenoidosa were observed during degradation. C. pyrenoidosa was able to consume the organic carbon present in the phenolic compounds as carbon source for its growth despite the inorganic carbon supplemented externally.

Standardization of the carbon-phenolic materials and processes. Vol. 1: Experimental studies

NASA Technical Reports Server (NTRS)

Hall, William B.

1988-01-01

Carbon-phenolic composite materials are used as ablative material in the solid rocket motor nozzle of the Space Shuttle. The nozzle is lined with carbon cloth-phenolic resin composites. The nominal effects of the completely consumed solid propellant on the carbon-phenolic material are given. The extreme heat and erosion of the burning propellant are controlled by the carbon-phenolic composite by ablation, the heat and mass transfer process in which a large amount of heat is absorbed by sacrificially removing material from the nozzle surface. Phenolic materials ablate with the initial formation of a char. The depth of the char is a function of the heat conduction coefficient of the composite. The char layer is a very poor heat conductor so it protects the underlying phenolic composite from the high heat of the burning propellant. The nozzle component ablative liners (carbon cloth-phenolic composites) are tape wrapped, hydroclave and/or autoclave cured, machined, and assembled. The tape consists of a prepreg broadcloth. The materials flow sheet for the nozzle ablative liners is shown. The prepreg is a three component system: phenolic resin, carbon cloth, and carbon filler. This is Volume 1 of two, Experimental Studies.