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Sample records for additive butylated hydroxytoluene

  1. Safety assessment of butylated hydroxyanisole and butylated hydroxytoluene as antioxidant food additives.

    PubMed

    Williams, G M; Iatropoulos, M J; Whysner, J

    1999-01-01

    Butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) are widely used antioxidant food additives. They have been extensively studied for potential toxicities. This review details experimental studies of genotoxicity and carcinogenicity which bear on cancer hazard assessment of exposure to humans. We conclude that BHA and BHT pose no cancer hazard and, to the contrary, may be anticarcinogenic at current levels of food additive use.

  2. 21 CFR 182.3173 - Butylated hydroxytoluene.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Butylated hydroxytoluene. 182.3173 Section 182.3173 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... § 182.3173 Butylated hydroxytoluene. (a) Product. Butylated hydroxytoluene. (b) Tolerance....

  3. 21 CFR 182.3173 - Butylated hydroxytoluene.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Butylated hydroxytoluene. 182.3173 Section 182.3173 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... § 182.3173 Butylated hydroxytoluene. (a) Product. Butylated hydroxytoluene. (b) Tolerance....

  4. 21 CFR 182.3173 - Butylated hydroxytoluene.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Butylated hydroxytoluene. 182.3173 Section 182.3173 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... § 182.3173 Butylated hydroxytoluene. (a) Product. Butylated hydroxytoluene. (b) Tolerance....

  5. 21 CFR 582.3173 - Butylated hydroxytoluene.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Butylated hydroxytoluene. 582.3173 Section 582.3173 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... § 582.3173 Butylated hydroxytoluene. (a) Product. Butylated hydroxytol- uene. (b) Tolerance....

  6. 21 CFR 582.3173 - Butylated hydroxytoluene.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Butylated hydroxytoluene. 582.3173 Section 582.3173 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... § 582.3173 Butylated hydroxytoluene. (a) Product. Butylated hydroxytol- uene. (b) Tolerance....

  7. 21 CFR 582.3173 - Butylated hydroxytoluene.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Butylated hydroxytoluene. 582.3173 Section 582.3173 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... § 582.3173 Butylated hydroxytoluene. (a) Product. Butylated hydroxytol- uene. (b) Tolerance....

  8. 21 CFR 582.3173 - Butylated hydroxytoluene.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Butylated hydroxytoluene. 582.3173 Section 582.3173 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED... § 582.3173 Butylated hydroxytoluene. (a) Product. Butylated hydroxytol- uene. (b) Tolerance....

  9. 21 CFR 182.3173 - Butylated hydroxytoluene.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Butylated hydroxytoluene. 182.3173 Section 182.3173 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical Preservatives §...

  10. 21 CFR 582.3173 - Butylated hydroxytoluene.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Butylated hydroxytoluene. 582.3173 Section 582.3173 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical...

  11. Transcriptome analysis provides new insights into liver changes induced in the rat upon dietary administration of the food additives butylated hydroxytoluene, curcumin, propyl gallate and thiabendazole.

    PubMed

    Stierum, Rob; Conesa, Ana; Heijne, Wilbert; Ommen, Ben van; Junker, Karin; Scott, Mary P; Price, Roger J; Meredith, Clive; Lake, Brian G; Groten, John

    2008-08-01

    Transcriptomics was performed to gain insight into mechanisms of food additives butylated hydroxytoluene (BHT), curcumin (CC), propyl gallate (PG), and thiabendazole (TB), additives for which interactions in the liver can not be excluded. Additives were administered in diets for 28 days to Sprague-Dawley rats and cDNA microarray experiments were performed on hepatic RNA. BHT induced changes in the expression of 10 genes, including phase I (CYP2B1/2; CYP3A9; CYP2C6) and phase II metabolism (GST mu2). The CYP2B1/2 and GST expression findings were confirmed by real time RT-PCR, western blotting, and increased GST activity towards DCNB. CC altered the expression of 12 genes. Three out of these were related to peroxisomes (phytanoyl-CoA dioxygenase, enoyl-CoA hydratase; CYP4A3). Increased cyanide insensitive palmitoyl-CoA oxidation was observed, suggesting that CC is a weak peroxisome proliferator. TB changed the expression of 12 genes, including CYP1A2. In line, CYP1A2 protein expression was increased. The expression level of five genes, associated with p53 was found to change upon TB treatment, including p53 itself, GADD45alpha, DN-7, protein kinase C beta and serum albumin. These array experiments led to the novel finding that TB is capable of inducing p53 at the protein level, at least at the highest dose levels employed above the current NOAEL. The expression of eight genes changed upon PG administration. This study shows the value of gene expression profiling in food toxicology in terms of generating novel hypotheses on the mechanisms of action of food additives in relation to pathology.

  12. Differential modifying effects of food additive butylated hydroxytoluene toward radiation and 4-nitro-quinoline 1-oxide-induced genotoxicity in yeast.

    PubMed

    Anjaria, Kshiti B; Bhat, Nagesh N; Shirsath, Kapil B; Sreedevi, B

    2011-01-01

    The modifying effect of butylated hydroxytoluene (BHT) on 60Co gamma radiation and 4-nitro-quinoline 1-oxide-induced gene conversion and back mutation frequencies was investigated using diploid yeast Saccharomyces cerevisiae D7. Cells were exposed to 100 or 400 Gy in the presence of 0.025-0.25 mM BHT. BHT exhibited radioprotection and significantly reduced radiation-induced gene conversion and back mutation frequencies as well as cell killing. In another set of experiments, cells were simultaneously treated with 0.025-0.1 mM BHT and 0.5 μM 4-NQO. BHT significantly enhanced 4-NQO-induced gene conversion and back mutation frequencies. BHT post-treatment did not modify radiation-induced genetic events but enhanced 4-NQO-induced back mutation frequencies, indicating its potential to act as a tumor-promoting agent with 4-NQO.

  13. Dietary butylated hydroxytoluene protects against aflatoxicosis in Turkeys.

    PubMed

    Klein, Patrick J; Van Vleet, Terry R; Hall, Jeffery O; Coulombe, Roger A

    2002-07-01

    Turkeys are among the most sensitive species to the toxic effects of the mycotoxin aflatoxin B(1) (AFB(1)). In mammals, dietary antioxidants, such as butylated hydroxytoluene (BHT), have been shown to lessen the toxic effects of AFB(1) by various mechanisms. To test whether BHT protects against aflatoxicosis in turkeys, we supplemented the feed of 10-day-old male white turkeys with low (1000 ppm) and high (4000 ppm) BHT for 20 days. AFB(1) (1 ppm) was then added to the diets and continued for another 10 days. Birds in the AFB(1)-only group had a lower weight gain, a condition that had returned to near control in groups fed diets containing AFB(1) + BHT. Significant elevations in serum aspartate transaminase, alanine aminotransferase, and lactate dehydrogenase, which were evident in the AFB(1) group, were reversed in the AFB(1) + BHT groups. Histopathology revealed hepatic submassive necrotic lesions and biliary hyperplasia, the severity of which was lessened in the AFB(1) + BHT-treated birds. Hepatocellular hydropic degeneration was observed in the BHT-only group, but not in the AFB(1) + BHT groups. This condition associated with BHT treatment was found in a separate study to be reversible and without any long-term adverse effects. These results indicate that BHT counteracts many of the deleterious effects caused by AFB(1) and that this antioxidant may prove to be a viable feed additive for the reduction of aflatoxicosis in turkeys.

  14. Cytotoxicity and apoptosis induction by butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT).

    PubMed

    Saito, Masatoshi; Sakagami, Hiroshi; Fujisawa, Seiichiro

    2003-01-01

    The cytotoxicity and apoptosis-inducing activity of butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), and 2-tert-butyl-4-methylphenol (BMP) and the mixture of BHA and BHT (BHA/BHT) (1:1, molar ratio) were investigated, using human promeylocytic leukemia cell lines (HL-60) and human squamous cell carcinoma cell lines (HSC-2). The 50% cytotoxic concentration (CC50) declined in the order of BHA, BHT (0.2-0.3 mM) > BHA/BHT (0.04-0.07 mM) > BMP (0.02-0.05 mM). The addition of antioxidants (N-acetyl-Lcysteine, sodium ascorbate, catalase) reduced the cytotoxicity of BHA/BHT or BMP against HSC-2 cells, but not that of BHA or BHT, whereas the addition of NADH, a quinone reductase to BMP, enhanced the cytotoxicity. These findings suggested that the cytotoxicity of BHA/BHT and BMP might be caused by reactive intermediates. BHA-induced cytotoxicity was enhanced by horseradish peroxidases, suggesting that BHA was oxidizable and produced cytotoxic BHA radicals. Internucleosomal DNA fragmentation of HL-60 cells was preferably induced by BHA/BHT and BMP, followed by BHA. The MnSOD mRNA expression in HL-60 cells assayed by reverse transcriptase-polymerase chain reaction was highly inhibited by BHA/BHT or BMP, accompanied by the change in the electrophoretic mobility of MnSOD on polyacryamide gel. These compounds activated caspase-3, 8 and 9 in HL-60 cells. Activations of caspases, particularly caspase-3, declined in the order of BHA/BHT > BHA > BMP > BHT. The most cytotoxic BMP activated caspase-3 activity to the least extent, possibly in part due to the occurrence of necrosis. The great cytotoxicity and apoptosis induction by BHA/BHT may be due to reactive intermediates derived from the interaction between BHA phenoxyl radical and BHT or BHT phenoxyl radical.

  15. Voltammetric Determination of Dinonyl Diphenylamine and Butylated Hydroxytoluene in Mineral and Synthetic Oil

    PubMed Central

    Xiang, Yaling; Qian, Xuzheng; Hua, Meng; Cheng, Bingxue; Chen, Wu; Li, Jian

    2016-01-01

    ABSTRACT A method is reported for the determination of diphenylamine and butylated hydroxytoluene in mineral and synthetic oil. The procedure used differential pulse voltammetry with a glassy carbon electrode. This method was then used for determining these antioxidants in supporting electrolyte consisting of dilute sulfuric acid and sodium dodecyl sulfonate in ethanol. Anodic peaks were obtained for both analytes. Oxidation peaks at 250 mV were observed from a mixture of butylated hydroxytoluene and dinonyl diphenylamine, allowing their simultaneous determination. This approach was successfully used for the determination of dinonyl diphenylamine and butylated hydroxytoluene in fortified mineral and synthetic oils with good accuracy and precision. PMID:27365537

  16. Testing usability of butylated hydroxytoluene in conservation of goat semen.

    PubMed

    Khalifa, T A A; Lymberopoulos, A G; El-Saidy, B E

    2008-10-01

    The objective of this study was to investigate whether butylated hydroxytoluene (BHT) could be used as a suitable supporter or alternative of egg yolk during preservation of goat spermatozoa. Three in vitro experiments and a fertility test were conducted to evaluate the effect of BHT on viability of chilled-stored semen as well as motility and kidding rate of frozen-thawed spermatozoa. In the first two experiments, ejaculates (n = 30/experiment) were collected from 10 bucks, split, diluted with egg yolk-based and egg yolk-free extenders supplemented with or without 0.3, 0.6, 2, 5 and 8 mM BHT and stored at 5 degrees C for 168 h. In the third experiment, 30 ejaculates were collected from the above-mentioned bucks, split and diluted with egg yolk-free extenders supplemented with or without 0.3, 0.6 and 0.9 mM BHT and egg yolk-based extenders supplemented with or without 5 mM BHT. Diluted semen was cooled to 5 degrees C over a period of 4 h, frozen and thawed in the form of 0.3-ml pellets. In the fertility test, 75 ejaculates were collected from two proven fertile bucks, split, diluted with egg yolk-free extenders containing 0.6 mm BHT and egg yolk-based extenders supplemented with or without 5 mM BHT, frozen and thawed as described above. An insemination volume of 0.6 ml containing 120-140 x 10(6) progressively motile spermatozoa was used for a single cervical insemination of cloprostenol-synchronized does (n = 230). The results showed that addition of 5 mM BHT to egg yolk-deficient (2.5%) extenders significantly improved viability of chilled-stored semen together with motility (48.5%) and fertility (62.5%) of frozen-thawed spermatozoa. Replacement of egg yolk in semen extenders by 0.6 mm BHT could sustain not only viability of chilled-stored semen but also post-thaw motility (47.5%) and fertility (53.75%) of frozen-thawed spermatozoa. In conclusion, supplementation of semen diluents with BHT can ameliorate preservability of goat sperm.

  17. Freezing dog semen in presence of the antioxidant butylated hydroxytoluene improves postthaw sperm membrane integrity.

    PubMed

    Neagu, V R; García, B Macías; Sandoval, C Salazar; Rodríguez, A Morillo; Ferrusola, C Ortega; Fernández, L González; Tapia, J A; Peña, F J

    2010-03-15

    In an attempt to evaluate the protective effect of a lipid-soluble antioxidant (butylated hydroxytoluene; BHT), semen from four dogs (Canis familiaris) was frozen in two different extenders (Uppsala or INRA-96 plus glycerol) with or without 1mM BHT. Sperm membrane integrity using flow cytometry and motility using a computerized system were evaluated in each experimental group. The Uppsala extender was superior in all aspects of sperm function. The percentage of sperm membranes was significantly higher in semen samples frozen in presence of BHT. Our results suggest that the Uppsala extender can be improved with the addition of BHT.

  18. Oxidative stress response and morphological changes of Blakeslea trispora induced by butylated hydroxytoluene during carotene production.

    PubMed

    Nanou, Konstadina; Roukas, Triantafyllos

    2010-04-01

    The adaptive response of the fungus Blakeslea trispora to the oxidative stress induced by butylated hydroxytoluene (BHT) during carotene production in shake flask culture was investigated. The culture response to oxidative stress was studied by measuring the specific activities of catalase (CAT) and superoxide dismutase (SOD) and the micromorphology of the fungus using a computerized image analysis system. The addition of exogenous BHT to the medium caused changes of the morphology of microorganism from aggregates with large projected area to aggregates with small projected area. This morphological differentiation of the fungus was associated with high oxidative stress as evidenced by remarkable increase of the specific activities of CAT and SOD. The oxidative stress in B. trispora resulted in a fivefold increase of carotene production. The highest concentration of carotenes (125.0 mg/g dry biomass) was obtained in culture grown in medium supplemented with 20 mM of BHT.

  19. Tests for mutagenic effects of ammoniated glycyrrhizin, butylated hydroxytoluene, and gum arabic in roden germ cells

    SciTech Connect

    Sheu, C.W.; Cain, K.T.; Rushbrook, C.J.; Jorgenson, T.A.; Generoso, W.M.

    1986-01-01

    Ammoniated glycyrrhizin, butylated hydroxytoluene, and gum Arabic are generally recognized as safe (GRAS) substances that are used primarily as additives in foods. These substances were incorporated into rodent diets and fed to male rats and mice for 10 and 8 wk, respectively. The treated male mice and rats were then tested for dominant lethal effects. The mice were also tested for induced heritable translocation. Results of the rat studies indicated a statistically significant dominant lethal effect of each of the compounds tested; however, the biological significance of this response is not known. Results of the mouse dominant lethal and heritable translocation studies, on the other hand, indicated no adverse effects of the compounds tested.

  20. Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites.

    PubMed

    Fujisawa, Seiichiro; Kadoma, Yoshinori; Yokoe, Ichiro

    2004-07-01

    To clarify the radical-scavenging activity of butylated hydroxytoluene (BHT), a food additive, stoichiometric factors (n) and inhibition rate constants (kinh) were determined for 2,6-di-tert-butyl-4-methylphenol (BHT) and its metabolites 2,6-di-tert-butyl-p-benzoquinone (BHT-Q), 3,5-di-tert-butyl-4-hydroxybenzaldehyde (BHA-CHO) and 3,5-di-tert-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadiene-1-one (BHT-OOH). Values of n and kinh were determined from differential scanning calorimetry (DSC) monitoring of the polymerization of methyl methacrylate (MMA) initiated by 2,2'-azobis(isobutyronitrile) (AIBN) or benzoyl peroxide (BPO) at 70 degrees C in the presence or absence of antioxidants (BHT-related compounds). The n values declined in the order BHT (1-2) > BHT-CHO, BHT-OOH (0.1-0.3) > BHT-Q ( approximately 0). The n value for BHT with AIBN was approximately 1.0, suggesting dimerization of BHT. The kinh values declined in the order BHT-Q ((3.5-4.6) x 10(4) M(-1)s(-1)) > BHT-OOH (0.7-1.9 x 10(4) M(-1)s(-1)) > BHT-CHO ((0.4-1.7 x 10(4) M(-1)s(-1)) > BHT ((0.1-0.2 x 10(4) M(-1)s(-1)). The kinh for metabolites was greater than that for the parent BHT. Growing MMA radicals initiated by BPO were suppressed much more efficiently by BHT or BHT-Q compared with those initiated by AIBN. BHT was effective as a chain-breaking antioxidant. PMID:15172835

  1. Radical-scavenging activity of butylated hydroxytoluene (BHT) and its metabolites.

    PubMed

    Fujisawa, Seiichiro; Kadoma, Yoshinori; Yokoe, Ichiro

    2004-07-01

    To clarify the radical-scavenging activity of butylated hydroxytoluene (BHT), a food additive, stoichiometric factors (n) and inhibition rate constants (kinh) were determined for 2,6-di-tert-butyl-4-methylphenol (BHT) and its metabolites 2,6-di-tert-butyl-p-benzoquinone (BHT-Q), 3,5-di-tert-butyl-4-hydroxybenzaldehyde (BHA-CHO) and 3,5-di-tert-butyl-4-hydroperoxy-4-methyl-2,5-cyclohexadiene-1-one (BHT-OOH). Values of n and kinh were determined from differential scanning calorimetry (DSC) monitoring of the polymerization of methyl methacrylate (MMA) initiated by 2,2'-azobis(isobutyronitrile) (AIBN) or benzoyl peroxide (BPO) at 70 degrees C in the presence or absence of antioxidants (BHT-related compounds). The n values declined in the order BHT (1-2) > BHT-CHO, BHT-OOH (0.1-0.3) > BHT-Q ( approximately 0). The n value for BHT with AIBN was approximately 1.0, suggesting dimerization of BHT. The kinh values declined in the order BHT-Q ((3.5-4.6) x 10(4) M(-1)s(-1)) > BHT-OOH (0.7-1.9 x 10(4) M(-1)s(-1)) > BHT-CHO ((0.4-1.7 x 10(4) M(-1)s(-1)) > BHT ((0.1-0.2 x 10(4) M(-1)s(-1)). The kinh for metabolites was greater than that for the parent BHT. Growing MMA radicals initiated by BPO were suppressed much more efficiently by BHT or BHT-Q compared with those initiated by AIBN. BHT was effective as a chain-breaking antioxidant.

  2. Intake of butylated hydroxyanisole and butylated hydroxytoluene and stomach cancer risk: results from analyses in the Netherlands Cohort Study.

    PubMed

    Botterweck, A A; Verhagen, H; Goldbohm, R A; Kleinjans, J; van den Brandt, P A

    2000-07-01

    Both carcinogenic and anticarcinogenic properties have been reported for the synthetic antioxidants butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT). The association between dietary intake of BHA and BHT and stomach cancer risk was investigated in the Netherlands Cohort Study (NLCS) that started in 1986 among 120,852 men and women aged 55 to 69 years. A semi-quantitative food frequency questionnaire was used to assess food consumption. Information on BHA or BHT content of cooking fats, oils, mayonnaise and other creamy salad dressings and dried soups was obtained by chemical analysis, a Dutch database of food additives (ALBA) and the Dutch Compendium of Foods and Diet Products. After 6.3 years of follow-up, complete data on BHA and BHT intake of 192 incident stomach cancer cases and 2035 subcohort members were available for case-cohort analysis. Mean intake of BHA or BHT among subcohort members was 105 and 351 microg/day, respectively. For consumption of mayonnaise and other creamy salad dressings with BHA or BHT no association with stomach cancer risk was observed. A statistically non-significant decrease in stomach cancer risk was observed with increasing BHA and BHT intake [rate ratio (RR) highest/lowest intake of BHA = 0.57 (95% confidence interval (CI): 0.25-1.30] and BHT = 0.74 (95% CI: 0.38-1.43). In this study, no significant association with stomach cancer risk was found for usual intake of low levels of BHA and BHT.

  3. Levels of synthetic antioxidants (ethoxyquin, butylated hydroxytoluene and butylated hydroxyanisole) in fish feed and commercially farmed fish.

    PubMed

    Lundebye, A-K; Hove, H; Måge, A; Bohne, V J B; Hamre, K

    2010-12-01

    Several synthetic antioxidants are authorized for use as feed additives in the European Union. Ethoxyquin (EQ) and butylated hydroxytoluene (BHT) are generally added to fish meal and fish oil, respectively, to limit lipid oxidation. The study was conducted to examine the concentrations of EQ, BHT and butylated hydroxyanisole (BHA) in several commercially important species of farmed fish, namely Atlantic salmon, halibut and cod and rainbow trout, as well as concentrations in fish feed. The highest levels of BHT, EQ and BHA were found in farmed Atlantic salmon fillets, and were 7.60, 0.17 and 0.07 mg kg(-1), respectively. The lowest concentrations of the synthetic antioxidants found were in cod. The concentration of the oxidation product ethoxyquin dimer (EQDM) was more than ten-fold higher than the concentration of parent EQ in Atlantic salmon halibut and rainbow trout, whereas this dimer was not detected in cod fillets. The theoretical consumer exposure to the synthetic antioxidants EQ, BHA and BHT from the consumption of farmed fish was calculated. The contribution of EQ from a single portion (300 g) of skinned fillets of the different species of farmed fish would contribute at most 15% of the acceptable daily intake (ADI) for a 60 kg adult. The consumption of farmed fish would not contribute measurably to the intake of BHA; however, a 300 g portion of farmed Atlantic salmon would contribute up to 75% of the ADI for BHT.

  4. Oxidative DNA damage and apoptosis induced by metabolites of butylated hydroxytoluene.

    PubMed

    Oikawa, S; Nishino, K; Oikawa, S; Inoue, S; Mizutani, T; Kawanishi, S

    1998-08-01

    DNA damage by metabolites of a food additive, butylated hydroxytoluene (BHT), was investigated as a potential mechanism of carcinogenicity. The mechanism of DNA damage by 2,6-di-tert-butyl-p-benzoquinone (BHT-quinone), 2,6-di-tert-butyl-4-hydroperoxyl-4-methyl-2,5-cyclohexadienone (BHT-OOH), and 3,5-di-tert-butyl-4-hydroxybenzaldehyde (BHT-CHO) in the presence of metal ions was investigated by using 32P-labeled DNA fragments obtained from the c-Ha-ras-1 proto-oncogene and the p53 tumor suppressor gene. BHT-OOH caused DNA damage in the presence of Cu(II), whereas BHT-quinone and BHT-CHO did not. However, BHT-quinone did induce DNA damage in the presence of NADH and Cu(II). Bathocuproine inhibited Cu(II)-mediated DNA damage, indicating the participation of Cu(I) in the process. Catalase also inhibited DNA damage induced by BHT-quinone, but not that induced by BHT-OOH. The DNA cleavage pattern observed with BHT-quinone plus NADH was different from that seen with BHT-OOH. With BHT-quinone plus NADH, piperidine-labile sites could be generated at nucleotides other than adenine residue. BHT-OOH caused cleavage specifically at guanine residues. Pulsed field gel electrophoresis showed that BHT-OOH and BHT-quinone induced DNA strand breaks in cultured cells, whereas BHT-CHO did not. Both BHT-quinone and BHT-OOH induced internucleosomal DNA fragmentation, which is the characteristic of apoptosis. Furthermore, flow cytometry analysis revealed an increase of peroxides in cultured cells treated with BHT-OOH or BHT-quinone. These results suggest that BHT-OOH participates in oxidative DNA damage directly, whereas BHT-quinone causes DNA damage through H2O2 generation, which leads to internucleosomal DNA fragmentation. PMID:9744574

  5. Oxidative DNA damage and apoptosis induced by metabolites of butylated hydroxytoluene.

    PubMed

    Oikawa, S; Nishino, K; Oikawa, S; Inoue, S; Mizutani, T; Kawanishi, S

    1998-08-01

    DNA damage by metabolites of a food additive, butylated hydroxytoluene (BHT), was investigated as a potential mechanism of carcinogenicity. The mechanism of DNA damage by 2,6-di-tert-butyl-p-benzoquinone (BHT-quinone), 2,6-di-tert-butyl-4-hydroperoxyl-4-methyl-2,5-cyclohexadienone (BHT-OOH), and 3,5-di-tert-butyl-4-hydroxybenzaldehyde (BHT-CHO) in the presence of metal ions was investigated by using 32P-labeled DNA fragments obtained from the c-Ha-ras-1 proto-oncogene and the p53 tumor suppressor gene. BHT-OOH caused DNA damage in the presence of Cu(II), whereas BHT-quinone and BHT-CHO did not. However, BHT-quinone did induce DNA damage in the presence of NADH and Cu(II). Bathocuproine inhibited Cu(II)-mediated DNA damage, indicating the participation of Cu(I) in the process. Catalase also inhibited DNA damage induced by BHT-quinone, but not that induced by BHT-OOH. The DNA cleavage pattern observed with BHT-quinone plus NADH was different from that seen with BHT-OOH. With BHT-quinone plus NADH, piperidine-labile sites could be generated at nucleotides other than adenine residue. BHT-OOH caused cleavage specifically at guanine residues. Pulsed field gel electrophoresis showed that BHT-OOH and BHT-quinone induced DNA strand breaks in cultured cells, whereas BHT-CHO did not. Both BHT-quinone and BHT-OOH induced internucleosomal DNA fragmentation, which is the characteristic of apoptosis. Furthermore, flow cytometry analysis revealed an increase of peroxides in cultured cells treated with BHT-OOH or BHT-quinone. These results suggest that BHT-OOH participates in oxidative DNA damage directly, whereas BHT-quinone causes DNA damage through H2O2 generation, which leads to internucleosomal DNA fragmentation.

  6. Hydrolysis of the quinone methide of butylated hydroxytoluene in aqueous solutions.

    PubMed

    Willcockson, Maren Gulsrud; Toteva, Maria M; Stella, Valentino J

    2013-10-01

    Butylated hydroxytoluene or BHT is an antioxidant commonly used in pharmaceutical formulations. BHT upon oxidation forms a quinone methide (QM). QM is a highly reactive electrophilic species that can undergo nucleophilic addition. Here, the kinetic reactivity of QM with water at various apparent pH values in a 50% (v/v) water-acetonitrile solution at constant ionic strength of I = 0.5 (NaCl)4 , was studied. The hydrolysis of QM in the presence of added acid, base, sodium chloride, and phosphate buffer resulted in the formation of only one product--the corresponding 3,5-di-tert-butyl-4-hydroxybenzyl alcohol (BA). The rate of BA formation was catalyzed by the addition of acid and base, but not chloride and phosphate species. Nucleophilic excipients, used in the pharmaceutical formulation, or nucleophilic groups on active pharmaceutical ingredient molecule may form adducts with QM, the immediate oxidative product of BHT degradation, thus having implications for drug product impurity profiles. Because of these considerations, BHT should be used with caution in formulations containing drugs or excipients capable of acting as nucleophiles.

  7. Effects of butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) on the acetylation of 2-aminofluorene and DNA-2-aminofluorene adducts in the rat.

    PubMed

    Chung, J G

    1999-10-01

    The effects of the synthetic phenolic antioxidants (butylated hydroxyanisole and butylated hydroxytoluene) on the in vivo acetylation of 2-aminofluorene and formation of DNA-2-aminofluorene adducts were investigated in male Sprague-Dawley rats. For in vitro examination, cytosols and intact cells, with or without butylated hydroxyanisole and butylated hydroxytoluene co-treatment, showed different percentages of 2-aminofluorene acetylation and DNA-2-aminofluorene adducts. For in vivo examination, pre-treatment of male rats with butylated hydroxyanisole and butylated hydroxytoluene (10 mg/kg) 48 h prior to the administration of 2-aminofluorene (50 mg/kg) resulted in 34% and 18%, 29% and 20% decreases, respectively, in the urinary and fecal recovery of N-acetyl-2-aminofluorene, and 34% and 19% decreases, respectively, in the metabolic clearance of 2-aminofluorene to N-acetyl-2-aminofluorene. Following exposure of rats to the 2-aminofluorene, with or without pretreatment with butylated hydroxyanisole and butylated hydroxytoluene, DNA-2-aminofluorene adducts were observed in the target tissues of liver and bladder, and also in circulating leukocytes. The DNA-2-aminofluorene adducts in liver, bladder, and leukocytes were decreased by pretreatment with butylated hydroxyanisole and butylated hydroxytoluene. This is the first demonstration that synthetic phenolic antioxidants decrease the N-acetylation of carcinogens and formation of DNA-carcinogen adducts in vivo.

  8. Inhibition of somatic embryo maturation in Sitka spruce [Picea sitchensis (Bong.) Carr.] by butylated hydroxytoluene, a volatile antioxidant released by parafilm.

    PubMed

    Selby, C; McRoberts, W C; Hamilton, J T; Harvey, B M

    1996-12-01

    Head-space volatiles above embryogenicPicea sitchensis (Bong.) Carr. (Sitka spruce) tissues cultured in glass Petri dishes sealed with Parafilm M or cling-film, were captured on Tenax adsorption traps and analysed by gas chromatography / mass spectrometry. Each sealing system released a single major compound into the head-space; butylated hydroxytoluene from Parafilm M and 2-ethyl-1-hexanol from cling-film. After two weeks sealed under Parafilm M butylated hydroxytoluene accumulated to 1.1 μg g(-1) FW in tissues and subsequent somatic embryo maturation was prevented. When butylated hydroxytoluene was supplied via the head-space (100 μg/250 ml flask) 0.5 μg g(-1) FW accumulated in tissues after two weeks and no somatic embryo maturation occurred. Potentially phytotoxic metabolites of butylated hydroxytoluene included a substituted stilbenequinone, butylated hydroxytoluene quinone methide and butylated hydroxytoluene dimer.

  9. PRODUCTION OF NATURAL BUTYLATED HYDROXYTOLUENE AS AN ANTIOXIDANT BY FRESHWATER PHYTOPLANKTON(1).

    PubMed

    Babu, Bakthavachalam; Wu, Jiunn-Tzong

    2008-12-01

    Butylated hydroxytoluene (BHT) is one of the synthetic antioxidant agents commonly used for food additives. In the present study, we determined that four freshwater phytoplankton, including a green alga (Botryococcus braunii Kütz.) and three cyanobacteria [Cylindrospermopsis raciborskii (Wolłosz.) Seenaya et Sabba Raju, Microcystis aeruginosa (Kütz.) and Oscillatoria sp.] were capable of producing this compound. Hexane extracts from all the studied species exhibited various degrees of antioxidative properties when they were tested with the β-carotene-linoleate (β-CL) assay and the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical-scavenging assay. The highest antioxidant activity was observed in the crude extracts of M. aeruginosa and B. braunii, which displayed a similar activity to synthetic BHT. Gas chromatography/mass spectroscopy (GC-MS) analysis of the purified fractions revealed that the active compound was identical to synthetic BHT. Culturing under various irradiances gave rise to different magnitudes of BHT production in cyanobacterial cells, showing that more BHT was produced in the cells irradiated with a higher light intensity, and its production was irradiance dependent. Moreover, the quantity of cellular BHT displayed a positive correlation with the antioxidative activity of the tested species. The present study confirms the production of BHT in all four of the studied freshwater phytoplankton and suggests that these species constitute a potential source for producing natural BHT.

  10. Butylated hydroxytoluene is a ligand of urinary proteins derived from female mice.

    PubMed

    Kwak, Jae; Josue, Jesusa; Faranda, Adam; Opiekun, Maryanne Curran; Preti, George; Osada, Kazumi; Yamazaki, Kunio; Beauchamp, Gary K

    2011-06-01

    Mice secrete substantial amounts of protein, particularly proteins called the major urinary proteins (MUPs), in urine. One function of MUPs is to sequester volatile pheromone ligands, thereby delaying their release and providing a stable long-lasting signal. Previously, only MUPs isolated from male mice have been used to identify ligands. Here, we tested the hypothesis that MUPs derived from females may also sequester volatile organic compounds. We identified butylated hydroxytoluene (BHT), a synthetic antioxidant present in the laboratory rodent diet, as a major ligand bound to urinary proteins derived from C57BL/6J female urine. BHT was also bound to the male-derived proteins, but the binding was less prominent than that in female urine, even though males express approximately 4 times more proteins than females. We confirmed that the majority of BHT in female urine was associated with the high molecular weight fraction (>10 kDa) and the majority of the proteins that sequestered BHT were MUPs as determined by sodium dodecyl sulfate-polyacrylamide gel electrophoresis. The sequestration of BHT by MUPs was further confirmed by employing the recombinant MUP8 whose natural analogue has been reported in both sexes. Therefore, our data indicate that MUPs expressed in both sexes can bind, transport, and excrete xenobiotics into urine and raise the possibility that in addition to the known role in chemical communication, MUPs function as a defense mechanism against exogenous toxins.

  11. Neutrophils are required for 3-methylcholanthrene-initiated, butylated hydroxytoluene-promoted lung carcinogenesis.

    PubMed

    Vikis, Haris G; Gelman, Andrew E; Franklin, Andrew; Stein, Lauren; Rymaszewski, Amy; Zhu, Jihong; Liu, Pengyuan; Tichelaar, Jay W; Krupnick, Alexander S; You, Ming

    2012-12-01

    Multiple studies have shown a link between chronic inflammation and lung tumorigenesis. Inbred mouse strains vary in their susceptibility to methylcholanthrene (MCA)-initiated butylated hydroxytoluene (BHT)-promoted lung carcinogenesis. In the present study we investigated whether neutrophils play a role in strain dependent differences in susceptibility to lung tumor promotion. We observed a significant elevation in homeostatic levels of neutrophils in the lungs of tumor-susceptible BALB/cByJ (BALB) mice compared to tumor-resistant C57BL/6J (B6) mice. Additionally, BHT treatment further elevated neutrophil numbers as well as neutrophil chemoattractant keratinocyte-derived cytokine (KC)/chemokine (C-X-C motif) ligand 1 (Cxcl1) levels in BALB lung airways. Lung CD11c+ cells were a major source of KC expression and depletion of neutrophils in BALB mice resulted in a 71% decrease in tumor multiplicity. However, tumor multiplicity did not depend on the presence of T cells, despite the accumulation of T cells following BHT treatment. These data demonstrate that neutrophils are essential to promote tumor growth in the MCA/BHT two-step lung carcinogenesis model.

  12. Estimated daily intakes of butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and tert-butyl hydroquinone (TBHQ) antioxidants in Korea.

    PubMed

    Suh, H-J; Chung, M-S; Cho, Y-H; Kim, J-W; Kim, D-H; Han, K-W; Kim, C-J

    2005-12-01

    The study was conducted to establish the estimated daily intake (EDI) of antioxidants such as butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and tert-butyl hydroquinone (TBHQ) in Korea. The EDIs were obtained from two sources. One of the estimations was based on the analytical determination of BHA, BHT and TBHQ in 12 food categories (ten food categories for TBHQ) and on individual dietary intake data obtained from the National Health and Nutrition Survey in 1998 (n=11 525, age > 1 year). The other EDIs of BHA, BHT and TBHQ were based on the maximum permitted levels specified in national food standards in Korea and on individual dietary intake data obtained from the National Health and Nutrition Survey in 1998 (n=11 525, age > 1 year). To establish the EDIs based on the analytical determination and on individual dietary intake data, 133 food samples in 12 food categories were selected from the foods considered to be representative sources of BHA, BHT and TBHQ in the Korean diet. Selected samples were analysed by GC with FID. BHA was not detected in any of the samples analysed. BHT and TBHQ were detected in the samples, but the levels were significantly lower than their maximum limits. The EDIs1 of BHT, and TBHQ for average consumers were 0.0156(-3), and 0.0012(-3) mg kg(-1) body weight bw day(-1) and as a proportion of the ADI were 0.0052 and 0.0002%, respectively. For 95th percentile consumers, the EDIs of BHT and TBHQ were 0.0080 and 0.0006 mg kg(-1) bw day(-1), and as a proportion of the ADI were 2.67 and 0.09%, respectively. EDIs for BHA, BHT and TBHQ based on the maximum permitted levels and on individual dietary intake data were 0.04, 0.04 and 0.04 mg kg(-1) bw day(-1), respectively. The EDIs of BHA, BHT and TBHQ for average consumers ranged from 6.00 to 14.42% of the ADI of each antioxidant. According to these results, the EDIs of BHA, BHT and TBHQ in Korea were significantly lower than ADI of these antioxidants established by the JECFA.

  13. Comparative cytotoxicity between butylated hydroxytoluene and its methylcarbamate derivative, terbucarb, on isolated rat hepatocytes

    SciTech Connect

    Nakagawa, Y.; Yaguchi, K.; Suzuki, T. )

    1994-08-01

    Butylated hydroxytoluene (3,5-di-tert-butyl-4-hydroxytoluene; BHT) is widely used as phenolic antioxidant in processed foods, cosmetics and petroleum products. It is well known that high doses of BHT cause acute hepatic damage accompanied by centrilobular necrosis in rats. The hepatic damage is associated with prolonged depletion of glutathione (GSH). Terbucarb (2,6-di-tert-butyl-para-tolyl-methylcarbamate), which has a methylcarbamate group substituted for the phenol group on BHT, was developed as an insecticide and is also presently used as a herbicide on turfgrass. Despite the metabolic and toxicological details known about BHT in vivo and in vitro, no extensive studies have been reported on the metabolism and toxicity of Terbucarb. The isolated hepatocyte system provides a very useful system for the study of the temporal sequences leading to cell damage caused by chemicals and drugs. Here, using freshly isolated rat hepatocytes, we report on the comparative toxic effects of BHT and its methylcarbamate derivative, Terbucarb. 17 refs., 2 figs., 2 tabs.

  14. Enhanced tumor development by butylated hydroxytoluene (BHT) in liver, lung and gastrointestinal tract

    SciTech Connect

    Witschi, H.P.

    1986-04-03

    Continuous feeding of 0.5% or 0.05% of butylated hydroxytoluene (BHT) enhances the development of spontaneously occurring liver tumors in C3H mice, but not in BALB/c mice. In mouse lung, the tumor-enhancing effects of BHT vary with the carcinogen used and in the gastrointestinal tract of mice and rats BHT enhances development of dimethylhydrazine-induced tumors but is without effect on tumors produced by methylnitrosourea. Strain differences, effect upon various carcinogens, paradoxical dose-responses and mechanisms of action remain major questions in the toxicology of BHT. 14 refs., 2 tabs.

  15. Fertility of boar semen cryopreserved in extender supplemented with butylated hydroxytoluene.

    PubMed

    Trzcińska, Monika; Bryła, Magdalena; Gajda, Barbara; Gogol, Piotr

    2015-02-01

    The present study was to determine the effect of butylated hydroxytoluene (BHT) on quality and fertilizing ability of frozen-thawed boar semen. In the first experiment, five crossbreds of Polish Landrace and Large White boars (five ejaculates per boar) were frozen in 0.5 mL straws after dilution with lactose-egg yolk-glycerol extender supplemented with 0 (control), 0.5, 1.0, and 2.0 mM BHT. The sperm quality was verified based on the motility (computer-assisted sperm analysis; total motility, %; progressive motility, %), membrane integrity (YO-PRO-1/propidium iodide [PI] assay), acrosome integrity (fluorescein isothiocyanate-conjugated with peanut agglutinin/PI), and lipid peroxidation (chemiluminescence method) at 15 minutes postthaw. In the second experiment, the semen cryopreserved in extender supplemented with 1.0 and 2.0 mM BHT were selected for intrauterine artificial insemination of synchronized gilts. An intrauterine artificial insemination with low numbers of spermatozoa (500 × 10(6)) was surgically infused into each uterine horn. The highest (P < 0.001) progressive motility (%), membrane integrity, and acrosomal integrity were noted by the addition of 1.0 and 2.0 mM BHT to the freezing extender. Moreover, the various concentrations (0.5-2.0 mM) of BHT caused a considerable decrease in lipid peroxidation in relation to the control extender (P < 0.001). The highest reproductive performance of inseminated gilts (farrowing rate, 86.7%; litter size, 10.8 ± 1.6) was observed when semen was cryopreserved in extender supplemented with 1.0 mM BHT. These findings demonstrate that the addition of 1.0 mM BHT to the freezing extender efficiently improves the fertilizing ability of postthaw boar spermatozoa.

  16. Fertility of boar semen cryopreserved in extender supplemented with butylated hydroxytoluene.

    PubMed

    Trzcińska, Monika; Bryła, Magdalena; Gajda, Barbara; Gogol, Piotr

    2015-02-01

    The present study was to determine the effect of butylated hydroxytoluene (BHT) on quality and fertilizing ability of frozen-thawed boar semen. In the first experiment, five crossbreds of Polish Landrace and Large White boars (five ejaculates per boar) were frozen in 0.5 mL straws after dilution with lactose-egg yolk-glycerol extender supplemented with 0 (control), 0.5, 1.0, and 2.0 mM BHT. The sperm quality was verified based on the motility (computer-assisted sperm analysis; total motility, %; progressive motility, %), membrane integrity (YO-PRO-1/propidium iodide [PI] assay), acrosome integrity (fluorescein isothiocyanate-conjugated with peanut agglutinin/PI), and lipid peroxidation (chemiluminescence method) at 15 minutes postthaw. In the second experiment, the semen cryopreserved in extender supplemented with 1.0 and 2.0 mM BHT were selected for intrauterine artificial insemination of synchronized gilts. An intrauterine artificial insemination with low numbers of spermatozoa (500 × 10(6)) was surgically infused into each uterine horn. The highest (P < 0.001) progressive motility (%), membrane integrity, and acrosomal integrity were noted by the addition of 1.0 and 2.0 mM BHT to the freezing extender. Moreover, the various concentrations (0.5-2.0 mM) of BHT caused a considerable decrease in lipid peroxidation in relation to the control extender (P < 0.001). The highest reproductive performance of inseminated gilts (farrowing rate, 86.7%; litter size, 10.8 ± 1.6) was observed when semen was cryopreserved in extender supplemented with 1.0 mM BHT. These findings demonstrate that the addition of 1.0 mM BHT to the freezing extender efficiently improves the fertilizing ability of postthaw boar spermatozoa. PMID:25468554

  17. Effect of urethane, dimethylnitrosamine, paraquat, and butylated hydroxytoluene on the activities of glycolytic key enzymes in mouse lung

    SciTech Connect

    Arany, I.; Rady, P.; Bojan, I.; Kertai, P.

    1981-12-01

    Effects of carcinogens and noncarcinogenic pulmonary toxicants on the activities of glycolytic key enzymes in the mouse lung were investigated. The carcinogens urethane (URTH) and dimethylnitrosamine (DMN) permanently enhanced, and the noncarcinogenic pulmonary toxicants paraquat (PAR) and butylated hydroxytoluene (BHT) temporarily, enhanced the activities of hexokinase (HK), phosphofructokinase (PFK), and pyruvate kinase (PK) in the lungs of mice.

  18. Effect of butylated hydroxytoluene on cryopreservation of Boer goat semen in Tris egg yolk extender.

    PubMed

    Memon, Akeel Ahmed; Wahid, H; Rosnina, Y; Goh, Y M; Ebrahimi, M; Nadia, F M; Audrey, G

    2011-11-01

    The aim of this study was to determine the effect of butylated hydroxytoluene (BHT), a lipid-soluble anti-oxidant added in different concentrations to the Tris egg yolk extenders on semen cytological parameters pre freezing and post thawing (motility, morphology, viability, acrosome integrity and membrane integrity) of Boer goat spermatozoa. A total of 40 ejaculates from four Boer goat bucks were collected using an artificial vagina. Ten replicates of the ejaculates were diluted with a Tris egg yolk based extender which contained various concentrations (0.5mM, 1.0mM, 2.0mM and 3.0mM) of butylated hydroxytoluene while one sample was processed without supplementation of antioxidant and served as control. The diluted semen was cooled at 4°C and loaded into the straw and then stored in liquid nitrogen. It was evident that supplementation of BHT produces positive effect in terms of motility, membrane integrity and acrosome integrity in comparison with the control group in cooled and frozen Boer goat semen. Results showed significant differences in motility, membrane integrity, acrosome integrity and viability of cooled and frozen Boer goat spermatozoa at different concentrations. Motility, membrane integrity, acrosome integrity and viability was significantly higher in all treated groups than the control group (P<0.05) while there was no significant differences (P>0.05) in morphology trait between all group in cooled semen. However, improvement (P<0.05) was observed only in terms of the membrane integrity and acrosome integrity compared to the control and other treated groups in frozen semen. In conclusion, BHT can be used in cryopreservation of Boer goat semen in order to reduce the oxidative stress on spermatozoa.

  19. Survival and fertility of boar spermatozoa after freeze-thawing in extender supplemented with butylated hydroxytoluene.

    PubMed

    Roca, Jordi; Gil, Maria A; Hernandez, Marta; Parrilla, Inma; Vazquez, Juan M; Martinez, Emilio A

    2004-01-01

    This study evaluated the protective effect of butylated hydroxytoluene (BHT), a lipid-soluble antioxidant, against cryopreservation injuries to boar spermatozoa. In experiment 1, the lowest BHT concentrations able to reduce lipid peroxidation in boar spermatozoa were determined. Nine BHT concentrations (ranging from 0.025 to 3.2 mM) were evaluated, and the lowest (P <.05) production of malondialdehyde (MDA), as an indicator of lipid peroxidation, was obtained when BHT ranged from 0.2 to 1.6 mM. In experiment 2, sperm survivability was evaluated when BHT was added to a postthaw freezing extender by measuring the degree of sperm lipid peroxidation (using MDA production) and by measuring parameter such as motility, plasma membrane and acrosome integrity, and cell apoptosis. The ability of thawed spermatozoa to fertilize in vitro-matured oocytes and of embryos to develop to the blastocyst stage in vitro was also assessed. Pooled sperm-rich fractions collected from 3 mature Pietrain boars were frozen in 0.5-mL straws after dilution with lactose-egg yolk-glycerol-Orvus ES Paste extender supplemented with 0, 0.2, 0.4, 0.8, and 1.6 mM BHT. Postthaw sperm survival, evaluated 30 and 150 minutes after thawing, was higher in BHT-treated spermatozoa, being significant (P <.05) when the freezing extender was supplemented with 0.2, 0.4, and 0.8 mM BHT. The addition of BHT to the freezing extender resulted in a significant (P <.05) decrease in the MDA concentration in thawed spermatozoa, irrespective of the level of BHT used. BHT had no effect on oocyte cleavage rates, but the development to blastocyst was improved for embryos derived from spermatozoa frozen in extender supplemented with 0.4 mM BHT (16% vs 29% of blastocysts per total oocytes; P <.05). In conclusion, under the conditions tested in the present study, the addition of BHT to the freezing extender improved the overall efficiency of thawed boar spermatozoa.

  20. Visible-light promoted degradation of the commercial antioxidants butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT): a kinetic study.

    PubMed

    Criado, Susana; Allevi, Carolina; Ceballos, Claudio; García, Norman A

    2007-01-01

    Visible-light photo-irradiation of the commercial phenolic antioxidants (PhAs) butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT), in the presence of vitamin B2 (riboflavin, Rf), in methanolic solutions and under aerobic conditions, results in the photo-oxidation of the PhAs. The synthetic dye photosensitiser Rose Bengal was also employed for auxiliary experiments. With concentrations of riboflavin and PhAs of ca. 0.02 mM and < 1 mM, respectively, the excited triplet state of the vitamin (3Rf*) is quenched by BHT in a competitive fashion with dissolved ground state triplet oxygen. From the quenching of 3Rf*, the semireduced form of the pigment is generated through an electron transfer process from BHT, with the subsequent production of superoxide anion radical (O2*-) by reaction with dissolved molecular oxygen. In parallel, the species singlet molecular oxygen, O2(1delta(g)), is also generated. Both reactive oxygen species produce the photodegradation of BHT. In the case of BHA, the lack of any effect exerted by superoxide dismutase drives out a significant participation of a O2(*-)-mediated mechanism. BHA mainly interacts with O2(1delta(g)) and exhibits a desirable property as an antioxidant--a relatively high capacity for O2(1delta(g)) de-activation and a low photodegradation efficiency by the oxidative species. Electrochemical determinations support the proposed photodegradative mechanism.

  1. Effect of various concentrations of butylated hydroxyanisole and butylated hydroxytoluene on freezing capacity of Turkman stallion sperm.

    PubMed

    Seifi-Jamadi, Afshin; Kohram, Hamid; Zareh-Shahne, Ahmad; Dehghanizadeh, Parvaneh; Ahmad, Ejaz

    2016-07-01

    The present study aimed to determine the effect of different concentrations of butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) on post-thaw stallion sperm quality. The ejaculates collected from four healthy mature Turkmen stallions were pooled and divided into eight aliquots. The samples were diluted with extenders containing different concentrations (0.5, 1 or 2mM/mL) of BHA or BHT. The positive control (PC) samples were diluted with extender containing 0.5% ethanol (v/v) whereas; the negative control (NC) samples were diluted with basic extender only. Semen samples were frozen according to a standard protocol. After thawing of samples, sperm motility, viability, membrane integrity, total abnormality and lipid peroxidation were assessed. The greatest (P<0.05) values for total sperm motility, viability and plasma membrane functionality and least values for malonedialdehyde (MDA) concentration were observed in samples supplemented either with 1mM BHT or 2mM BHA. However, the progressive motility was greater (P<0.05) only in samples treated with 2mM BHA. In conclusion, the use of 1mM BHT or 2mM BHA in extender improves the freezing capacity of stallion sperm by reducing oxidative stress during freeze-thaw process.

  2. Mechanisms of butylated hydroxytoluene chemoprevention of aflatoxicosis-inhibition of aflatoxin B{sub 1} metabolism

    SciTech Connect

    Guarisco, John A.; Hall, Jeffery O.; Coulombe, Roger A.

    2008-03-15

    Chemoprevention of toxicoses and/or cancer through the use of nutrients or pharmacologic compounds is the subject of intense study. Among the many compounds examined, food additives such as antioxidants are being considered due to their ability to reduce disease formation by either induction or inhibition of key enzyme systems. One such compound, butylated hydroxytoluene (BHT), has been found to protect against cancer formation caused by exposure to aflatoxin B{sub 1} (AFB{sub 1}) in rodents. We have shown that dietary BHT protects against clinical signs of aflatoxicosis in turkeys, a species that is very susceptible to this mycotoxin. In this study, the effect of BHT on AFB{sub 1} metabolism and other cytochrome P450 (CYP)-related enzyme activities in turkey liver microsomes was examined to discern possible mechanisms of BHT-mediated protection against aflatoxicosis. Ethoxyresorufin O-deethylase (EROD), methoxyresorufin O-demethylase (MROD), prototype activities for CYP1A1 and 1A2, respectively, were decreased in the BHT fed (4000 ppm) animals, while oxidation of nifedipine, a prototype activity for CYP3A4, was increased. However, BHT added to microsomal incubations inhibited these CYP activities in a concentration-related manner. Importantly, BHT inhibited conversion of AFB{sub 1} to the reactive intermediate AFB{sub 1}-8,-9-epoxide (AFBO), exhibiting Michaelis-Menton competitive inhibition kinetics (Ki = 0.81 {mu}M). Likewise, microsomes prepared from turkeys fed BHT were significantly less active in AFBO formation compared to those from control birds. When turkeys were fed BHT for up to 40 days, residual BHT was present in liver, breast meat, thigh meat and abdominal fat in concentrations substantially below U.S. FDA guidelines for this antioxidant, but in concentrations greater than the Ki, likely sufficient to inhibit bioactivation of AFB{sub 1}in vivo. BHT-induced hydropic degeneration in the livers of BHT fed animals was significantly greater in birds that

  3. Mechanisms of butylated hydroxytoluene chemoprevention of aflatoxicosis--inhibition of aflatoxin B1 metabolism.

    PubMed

    Guarisco, John A; Hall, Jeffery O; Coulombe, Roger A

    2008-03-15

    Chemoprevention of toxicoses and/or cancer through the use of nutrients or pharmacologic compounds is the subject of intense study. Among the many compounds examined, food additives such as antioxidants are being considered due to their ability to reduce disease formation by either induction or inhibition of key enzyme systems. One such compound, butylated hydroxytoluene (BHT), has been found to protect against cancer formation caused by exposure to aflatoxin B1 (AFB1) in rodents. We have shown that dietary BHT protects against clinical signs of aflatoxicosis in turkeys, a species that is very susceptible to this mycotoxin. In this study, the effect of BHT on AFB1 metabolism and other cytochrome P450 (CYP)-related enzyme activities in turkey liver microsomes was examined to discern possible mechanisms of BHT-mediated protection against aflatoxicosis. Ethoxyresorufin O-deethylase (EROD), methoxyresorufin O-demethylase (MROD), prototype activities for CYP1A1 and 1A2, respectively, were decreased in the BHT fed (4000 ppm) animals, while oxidation of nifedipine, a prototype activity for CYP3A4, was increased. However, BHT added to microsomal incubations inhibited these CYP activities in a concentration-related manner. Importantly, BHT inhibited conversion of AFB1 to the reactive intermediate AFB1-8,-9-epoxide (AFBO), exhibiting Michaelis-Menton competitive inhibition kinetics (Ki=0.81 microM). Likewise, microsomes prepared from turkeys fed BHT were significantly less active in AFBO formation compared to those from control birds. When turkeys were fed BHT for up to 40 days, residual BHT was present in liver, breast meat, thigh meat and abdominal fat in concentrations substantially below U.S. FDA guidelines for this antioxidant, but in concentrations greater than the Ki, likely sufficient to inhibit bioactivation of AFB1in vivo. BHT-induced hydropic degeneration in the livers of BHT fed animals was significantly greater in birds that remained on BHT treatment for up to

  4. Estimates of the theoretical maximum daily intake of erythorbic acid, gallates, butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) in Italy: a stepwise approach.

    PubMed

    Leclercq, C; Arcella, D; Turrini, A

    2000-12-01

    The three recent EU directives which fixed maximum permitted levels (MPL) for food additives for all member states also include the general obligation to establish national systems for monitoring the intake of these substances in order to evaluate their use safety. In this work, we considered additives with primary antioxidant technological function for which an acceptable daily intake (ADI) was established by the Scientific Committee for Food (SCF): gallates, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and erythorbic acid. The potential intake of these additives in Italy was estimated by means of a hierarchical approach using, step by step, more refined methods. The likelihood of the current ADI to be exceeded was very low for erythorbic acid, BHA and gallates. On the other hand, the theoretical maximum daily intake (TMDI) of BHT was above the current ADI. The three food categories found to be main potential sources of BHT were "pastry, cake and biscuits", "chewing gums" and "vegetables oils and margarine"; they overall contributed 74% of the TMDI. Actual use of BHT in these food categories is discussed, together with other aspects such as losses of this substance in the technological process and percentage of ingestion in the case of chewing gums.

  5. Effects of butylated hydroxyanisole and butylated hydroxytoluene on DNA adduct formation and arylamines N-acetyltransferase activity in PC-3 cells (human prostate tumor) in vitro.

    PubMed

    Yeh, C C; Chung, J G; Wu, H C; Li, Y C; Lee, Y M; Hung, C F

    2000-11-01

    The effects of butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) on the N-acetyltransferase (NAT) activity and DNA adduct formation in PC-3 cells (human prostate tumor) was studied. PC-3 cells were placed into tissue culture flasks and grown in an incubator as cytosols and intact cells. The BHA or BHT were added to the cytosols and intact cells. The NAT activity in cytosol and intact PC-3 cells were measured by HPLC assaying exhibited for the amounts of N-acetyl-2-aminofluorene and N-acetyl-p-aminobenzoic acid, 2-aminofluorene and p-aminobenzoic acid. The NAT activity in PC-3 cells and cytosols were inhibited by BHA or BHT in a dose-dependent manner; that is, the higher the concentrations of BHA or BHT the higher inhibition of NAT activity. The NAT values of K(m) and V(max) from PC-3 cells were also decreased by BHA or BHT in both cytosols and intact cells. The data also demonstrated concomitant exposure to BHA or BHT decreased AF-DNA adduct formation which was seen in the PC-3 cells. In addition, the formation of DNA adduct was decreased after BHA or BHT exposure. These findings suggested the usefulness of using human cultured PC-3 cells for assessing arylamine-induced DNA adduct formation. Furthermore, the findings illustrate how effectively BHA or BHT reduce the adduct formation.

  6. Quantitative determination of butylated hydroxyanisole, butylated hydroxytoluene, and tert-butyl hydroquinone in oils, foods, and biological fluids by high-performance liquid chromatography with fluorometric detection.

    PubMed

    Yankah, V V; Ushio, H; Ohshima, T; Koizumi, C

    1998-11-01

    Concentrations of synthetic antioxidants butylated hydroxyanisole, butylated hydroxytoluene, and tert-butyl hydroquinone were quantified using a high-performance liquid chromatograph with spectrofluorometric detector. The antioxidants were separated and eluted on a reversed-phase column by gradient of a mixture of H2O/acetonitrile/acetic acid (66.5: 28.5:5, by vol) and a mixture of acetonitrile/acetic acid (95:5, vol/vol). The eluants were monitored at emission and excitation wavelengths of 310 and 280 nm, respectively. Calibration curves obtained using peak areas against concentration showed high coefficients of multiple determination (R2 > 0.99) for all antioxidants. Known concentrations of added antioxidant standards were recoverable within 98-99% from oils and over 93% from mouse blood. This method requires minimum sample extraction and purification before analysis and provides a relatively high percentage recovery. The method has been applied successfully for the measurement of antioxidant concentrations in oils, dried foods, and biological fluids.

  7. [Determination of antioxidants butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) in cosmetics by gas chromatography-mass spectrometry selected ion method].

    PubMed

    Zhang, Wei-Ya; Wu, Cai-Ying; Wang, Cheng-Yun; Yang, Zuo-Jun; Liu, Li

    2002-03-01

    A new method for the determination of butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) in cosmetics by gas chromatography-mass spectrometry selected ion storage (SIS) method was developed. The BHA and BHT in samples were extracted by methanol. The m/z 165 and m/z 205 were the monitoring ion for BHA and BHT respectively. The detection limits of BHA and BHT in samples were 2.5 micrograms/g and 0.5 microgram/g, respectively. The method is simple, rapid and accurate.

  8. The antiviral effectiveness of butylated hydroxytoluene on herpes cutaneous infections in hairless mice

    SciTech Connect

    Keith, A.D.; Arruda, D.; Snipes, W.; Frost, P.

    1982-06-01

    Hairless mice, cutaneously infected with herpes simplex virus type 1 (HSV-1), were treated topically with butylated hydroxytoluene (BHT). The effectiveness of BHT in shortening the duration of infections was assayed under three conditions. In the first experiments, mice undergoing primary infections with no prior immunity to HSV-1 were utilized. These animals tended to develop deep lesions that were not typical of recurrent HSV-1 infections in humans. A second set of experiments utilized mice that had recovered from a primary infection and that were immunosuppressed by ..gamma.. irradiation. Immunosuppression was essential for the full development of lesions upon reinfection. The lesions in these animals remained more localized with less tendency to spread into deep tissues. A third set of experiments utilized animals that were subcutaneously inoculated with human serum ..gamma..-globulin 24 hr prior to infection. Lesions on these animals also remained localized and did not penetrate into deep tissues. Under all three conditions, BHT was found to be effective in reducing the clearance time of HSV-1 cutaneous lesions when applied topically to the infected area.

  9. Potentiation of butylated hydroxytoluene-induced acute lung damage by oxygen: cell kinetics and collagen

    SciTech Connect

    Haschek, W.M.; Reiser, K.M.; Klein-Szanto, A.J.P.; Kehrer, J.P.; Smith, L.H.; Last, J.A.; Witschi, H.P.

    1983-01-01

    Changes in cell proliferation and in collagen synthesis were studied in young adult male BALB/c mice injected intraperitoneally with 400 mg/kg of butylated hydroxytoluene (BHT) in corn oil or corn oil alone and immediately exposed to 70% oxygen or air for 6 days. Mice received (/sup 3/H)thymidine either as a single injection 90 min before being killed or as a continual infusion via an osmotic minipump. Autoradiography was done 2 to 14 days after BHT injection, and cell kinetic studies were performed. In a similar experiment, mice were injected intraperitoneally with (/sup 3/H)proline 3 h before being killed, and type I/type III collagen ratio in newly synthesized lung collagen was determined. It was found that exposure to 70% oxygen immediately after the administration of BHT initially delayed the epithelial cell proliferation and the decrease in the percentage of newly synthesized type III collagen that occurred after BHT alone. Once the animals were removed from oxygen there was a compensatory burst of cell proliferation and a precipitous drop in the percentage of newly synthesized type III collagen. The proliferating cell population after removal from oxygen was primarily interstitial and not epithelial. When exposure to oxygen was delayed, cell proliferation was similar to that seen after BHT injection alone.

  10. Differential expression of forkhead box transcription factors following butylated hydroxytoluene lung injury.

    PubMed

    Kalinichenko, V V; Lim, L; Shin, B; Costa, R H

    2001-04-01

    The forkhead box (Fox) proteins are a growing family of transcription factors that have important roles in cellular proliferation and differentiation and in organ morphogenesis. The Fox family members hepatocyte nuclear factor (HNF)-3beta (Foxa2) and HNF-3/forkhead homolog (HFH)-8 (FREAC-1, Foxf1) are expressed in adult pulmonary epithelial and mesenchymal cells, respectively, but these cells display only low expression levels of the proliferation-specific HFH-11B gene (Trident, Foxm1b). The regulation of these Fox transcription factors in response to acute lung injury, however, has yet to be determined. We report here on the use of butylated hydroxytoluene (BHT)-mediated lung injury to demonstrate that HFH-11 protein and RNA levels were markedly increased throughout the period of lung repair. The maximum levels of HFH-11 were observed by day 2 following BHT injury when both bronchiolar and alveolar epithelial cells were undergoing extensive proliferation. Although BHT lung injury did not alter epithelial cell expression of HNF-3beta, a 65% reduction in HFH-8 mRNA levels was observed during the period of mesenchymal cell proliferation. HFH-8-expressing cells were colocalized with platelet endothelial cell adhesion molecule-1-positive alveolar endothelial cells and with alpha-smooth muscle actin-positive peribronchiolar smooth muscle cells.

  11. Understanding the chemistry behind the antioxidant activities of butylated hydroxytoluene (BHT): a review.

    PubMed

    Yehye, Wageeh A; Rahman, Noorsaadah Abdul; Ariffin, Azhar; Abd Hamid, Sharifah Bee; Alhadi, Abeer A; Kadir, Farkaad A; Yaeghoobi, Marzieh

    2015-08-28

    Hindered phenols find a wide variety of applications across many different industry sectors. Butylated hydroxytoluene (BHT) is a most commonly used antioxidant recognized as safe for use in foods containing fats, pharmaceuticals, petroleum products, rubber and oil industries. In the past two decades, there has been growing interest in finding novel antioxidants to meet the requirements of these industries. To accelerate the antioxidant discovery process, researchers have designed and synthesized a series of BHT derivatives targeting to improve its antioxidant properties to be having a wide range of antioxidant activities markedly enhanced radical scavenging ability and other physical properties. Accordingly, some structure-activity relationships and rational design strategies for antioxidants based on BHT structure have been suggested and applied in practice. We have identified 14 very sensitive parameters, which may play a major role on the antioxidant performance of BHT. In this review, we attempt to summarize the current knowledge on this topic, which is of significance in selecting and designing novel antioxidants using a well-known antioxidant BHT as a building-block molecule. Our strategy involved investigation on understanding the chemistry behind the antioxidant activities of BHT, whether through hydrogen or electron transfer mechanism to enable promising anti-oxidant candidates to be synthesized.

  12. Cell kinetics in mouse lung following administration of carcinogens and butylated hydroxytoluene

    SciTech Connect

    Witschi, H.P.; Morse, C.C.

    1985-01-01

    A series of experiments is described which was designed to test the hypothesis that, in mouse lung, enhancement of tumor development could occur independently of overall alveolar cell hyperplasia. Male A/J mice were given 1000 mg/kg of urethane or 10 mg/kg of 3-methylcholanthrene (MCA). Alveolar cells were labeled through continuous infusion of (TH)thymidine for 6 weeks after administration of the carcinogen. Urethane produced a significant hyperplasia of the type II alveolar cell population, whereas MCA had no such effect. Five repeated injections of 300 mg/kg of butylated hydroxytoluene (BHT), a procedure known to enhance lung tumor development, produced cell hyperplasia only during the first 2 weeks; later the mice became resistant to the action of BHT. In animals treated with piperonyl butoxide prior to BHT, cell proliferation was abolished. BHT still had a small but significant enhancing effect on tumor development. However, this effect was dwarfed by the observation that piperonyl butoxide alone greatly inhibited tumor development. The data do not allow exclusion of alveolar cell hyperplasia as a mechanism in BHT-mediated enhancement of mouse lung tumor development. 19 references, 4 figures, 3 tables.

  13. Effect of butylated hydroxytoluene on dog sperm longevity in chilling storage and cryopreservation.

    PubMed

    Sahashi, Yu; Otsuki, Tsubasa; Higaki, Shogo; Nagano, Masashi; Yamashita, Yasuhisa; Hishinuma, Mitsugu

    2011-07-01

    This study evaluated the effect of butylated hydroxytoluene (BHT), a lipid-soluble antioxidant, on dog sperm in chilling storage and cryopreservation. In Experiment 1, 0.2, 0.4, 0.8 and 1.6 mM BHT were added to egg yolk Tris extender (EYT), and sperm were stored at 4°C for 96 hr. Sperm motility, viability, acrosomal integrity and morphological abnormality in the BHT treatment groups were not different from those of the control (0 mM BHT). In Experiment 2, the effect of BHT in EYT containing 0.75% Equex STM paste and 5% glycerol on survivability of cryopreserved sperm was examined after culture at 39°C for 3 hr. Sperm motility, viability and acrosomal integrity in the 0.2 to 0.8 mM BHT treatment groups were not different from those of the control. However, sperm motility, viability and acrosomal integrity decreased when 1.6 mM BHT was added to the extender (P<0.05). In conclusion, supplementation of the extender with 0.2 to 0.8 mM BHT did not affect characteristics of dog sperm in chilling storage and cryopreservation. Supplementation of 1.6 mM BHT did not affect characteristics of chilled sperm but impaired longevity of cryopreserved sperm in the dog.

  14. Effects of dietary butylated hydroxytoluene on aflatoxin B1-relevant metabolic enzymes in turkeys.

    PubMed

    Klein, P J; Van Vleet, T R; Hall, J O; Coulombe, R A

    2003-05-01

    We have shown previously that the extreme sensitivity of turkeys to aflatoxin B(1) (AFB(1)) is due to a combination of efficient AFB(1) activation by cytochrome P450s (CYPs) 1A and deficient detoxification by glutathione S-transferases (GSTs). Phenolic antioxidants such as butylated hydroxytoluene (BHT) have been shown to be chemoprotective in some animal models due, in part, to modulation of AFB(1)-relevant phase I and/or phase II activities, and we wished to determine whether BHT has a similar effect in turkeys. Ten-day-old male turkeys were maintained on diets amended with 1000 or 4000 ppm of BHT for 10 days, then sampled. Hepatic microsomal CYP 1A activity as well as conversion of AFB(1) to the putative toxic metabolite, the exo-AFB(1)-8,9-epoxide (AFBO), were significantly lower compared with control. Conversely, dietary BHT significantly increased activities of several isoforms of hepatic cytosolic GST, as well quinone oxidoreductase (QOR). Western immunoblotting confirmed that dietary BHT increased expression of homologues to rodent GST isoforms Yc1, Yc2 and Ya. There was, however, no observable BHT-related increase in GST-mediated specific conjugation with microsomally-generated AFBO. In total, our data indicates that dietary BHT modulates a variety of AFB(1)-relevant phase I and phase II enzymes, while having no measurable effect towards specific AFB(1) detoxification by GST.

  15. Butylated hydroxytoluene analogs: synthesis and evaluation of their multipotent antioxidant activities.

    PubMed

    Yehye, Wageeh A; Abdul Rahman, Noorsaadah; Alhadi, Abeer A; Khaledi, Hamid; Weng, Ng Seik; Ariffin, Azhar

    2012-06-25

    A computer-aided predictions of antioxidant activities were performed with the Prediction Activity Spectra of Substances (PASS) program. Antioxidant activity of compounds 1, 3, 4 and 5 were studied using 1,1-diphenyl-2-picrylhydrazyl (DPPH) and lipid peroxidation assays to verify the predictions obtained by the PASS program. Compounds 3 and 5 showed more inhibition of DPPH stable free radical at 10⁻⁴ M than the well-known standard antioxidant, butylated hydroxytoluene (BHT). Compound 5 exhibited promising in vitro inhibition of Fe²⁺-induced lipid peroxidation of the essential egg yolk as a lipid-rich medium (83.99%, IC₅₀ 16.07 ± 3.51 μM/mL) compared to α-tocopherol (α-TOH, 84.6%, IC₅₀ 5.6 ± 1.09 μM/mL). The parameters for drug-likeness of these BHT analogues were also evaluated according to the Lipinski’s “rule-of-five” (RO5). All the BHT analogues were found to violate one of the Lipinski’s parameters (LogP > 5), even though they have been found to be soluble in protic solvents. The predictive polar surface area (PSA) and absorption percent (% ABS) data allow us to conclude that they could have a good capacity for penetrating cell membranes. Therefore, one can propose these new multipotent antioxidants (MPAOs) as potential antioxidants for tackling oxidative stress and lipid peroxidation processes.

  16. Antioxidant activity and cytotoxicity as mediators of the neutrophil chemiluminescence inhibition by butylated hydroxytoluene.

    PubMed

    Kabeya, L M; Kanashiro, A; Azzolini, A E C S; Santos, A C; Lucisano-Valim, Y M

    2008-01-01

    The tissue damage found in some inflammatory and autoimmune diseases has been shown to be mediated by an increased activation of neutrophil effector functions. In this study, we investigated the inhibitory effect of the phenolic compound butylated hydroxytoluene (BHT) on reactive oxygen species (ROS) generation by opsonized zymosan-stimulated neutrophils, assessed by luminol- and lucigenin-enhanced chemiluminescence (CL-lum and CL-luc, respectively), and some aspects of its mechanism of action. BHT showed concentration-dependent: (a) inhibitory effect on CL-lum and CL-luc; (b) cytotoxic effect, expressed by increased lactate dehydrogenase leakage by the cells; (c) interaction with neutrophil membranes; (d) ROS scavenger activity. These biological effects were observed in the same range of concentrations (0-5 x 10(-5) mol/l). Taken together, the results suggest that inhibition of neutrophil chemiluminescence by BHT was a result of multiple mechanisms, especially a cytotoxic effect probably mediated by BHT interaction with neutrophils membranes, and the ROS scavenging effect.

  17. Butylated hydroxytoluene (BHT) induction of pulmonary inflammation: a role in tumor promotion.

    PubMed

    Bauer, A K; Dwyer-Nield, L D; Keil, K; Koski, K; Malkinson, A M

    2001-01-01

    Chronic pulmonary inflammatory diseases predispose towards lung cancer by unknown mechanisms. Butylated hydroxytoluene (BHT) administration to mice causes lung injury and a subsequent inflammatory response, and when administered chronically to certain inbred strains following carcinogen treatment, increases lung tumor multiplicity. We hypothesize that inflammation promotes lung tumor growth in this model system and have begun to examine this hypothesis by assessing inflammatory parameters in inbred strains that vary in their susceptibility to promotion. Positive correlations were found between susceptibilities to tumor promotion and BHT induction of alveolar macrophage and lymphocyte infiltration into alveolar airspaces, and increased vascular permeability (P < .03, P < .04, and P < .005, respectively). The amounts of pulmonary cyclooxygenase (COX)-1 and COX-2 did not strongly correlate with promotion. Because persistent elevation of macrophage content is the hallmark of a chronic inflammatory response, the alveolar macrophage population was depleted by adding chlorine to the drinking water prior to carcinogenesis. This treatment reduced lung tumor multiplicity following 2-stage carcinogenesis (P < .05). These correlations between inflammatory and tumorigenic responses to BHT, along with decreased tumorigenesis after macrophage depletion, are consistent with a role of inflammation in promotion. Inflammatory mediators may provide targets for early diagnosis and chemoprevention.

  18. Effect of butylated hydroxytoluene on bull spermatozoa frozen in egg yolk-citrate extender.

    PubMed

    Shoae, A; Zamiri, M J

    2008-03-01

    Effect of butylated hydroxytoluene (BHT) on the quality of frozen-thawed Holstein bull sperm in egg yolk-citrate extender was evaluated. High quality semen samples were diluted in egg yolk-citrate extenders containing 0, 0.5, 1, 2 and 4 mM BHT and subsequently frozen in liquid nitrogen. Pre-freeze and post-thaw progressive motility, and live/dead ratio and acrosomal integrity of 200 sperm per slide, stained with Eosin-Nigrosin and Giemsa, were evaluated at 0, 2 and 4 h after thawing. There was a significant decrease in forward motility, livability and acrosomal integrity up to 4 h after thawing the frozen sperm. Upon thawing, sperm progressive motility at 1 mM BHT was significantly (P<0.001) higher (11%) than other groups, but percentages of live sperm and live sperm with intact acrosomes were higher at 0.5 mM BHT. BHT at 4 mM BHT caused a significant decrease in motility, livability and acrosomal integrity during preparatory stages of freezing sperm. It is concluded that 0.5-1.0 mM BHT can be beneficial for freezing Holstein bull spermatozoa in egg yolk-citrate diluent, when inseminated immediately after thawing.

  19. Isotope effects on the metabolism and pulmonary toxicity of butylated hydroxytoluene in mice by deuteration of the 4-methyl group

    SciTech Connect

    Mizutani, T.; Yamamoto, K.; Tajima, K.

    1983-06-30

    A comparative test in mice for pulmonary toxicity between butylated hydroxytoluene (2,6-di-tert.-butyl-4-methylphenol, BHT) and 2,6-di-tert.-butyl-4-(alpha, alpha, alpha-2H3)methylphenol (BHT-d3) showed a significantly lower toxic potency of the latter. The rate of in vitro BHT metabolism to 2,6-di-tert.-butyl-4-methylene-2,5-cyclohexadienone (BHT-QM) was slowed by deuterating BHT in the 4-methyl group. On the other hand, the rate of in vitro metabolism to 2,6-di-tert.-butyl-4-hydroxy-4-methyl-2,5-cyclohexadienone (BHT-OH) was increased with the deuteration. A similar isotope effect of the deuterium substitution on the in vivo metabolic rates of BHT was observed. These observations support the concept that the lung damage caused by BHT is mediated by BHT-QM. The pulmonary toxicity of 2-tert.-butyl-4-ethylphenol (4-EP) and their deuterated analogs was also compared. 2-tert.-Butyl-4-(1,1-2H2)ethylphenol (4-EP-d2) showed a significantly lower toxic potency than 4-EP, whereas 2-tert.-butyl-4-(2,2,2-2H3)ethylphenol (4-EP-d3) showed a toxic potency comparable to that of 4-EP. This result is consistent with the hypothesis that a quinone methide metabolite is responsible for the onset of lung damage produced by 4-EP as well as BHT.

  20. Butylated hydroxytoluene inclusion in semen extender improves the post-thawed semen quality of Nili-Ravi buffalo (Bubalus bubalis).

    PubMed

    Ijaz, A; Hussain, A; Aleem, M; Yousaf, M S; Rehman, H

    2009-05-01

    The study was carried out to evaluate the potential impact of butylated hydroxytoluene (BHT) on the frozen-thawed semen quality of Nili-Ravi buffalo bulls. Ejaculated bull semen was extended in a Tris-citrate egg yolk extender containing various concentrations of BHT (0.5, 1.0, 2.0 and 3.0mM). Semen was frozen at -196 degrees C using 50 x 10(6) spermatozoa per 0.5 mL straws. Five straws from each treatment were thawed to assess the semen quality in terms of sperm motility, viability, plasma membrane integrity and acrosomal integrity. Post-thawed sperm motility was determined using a phase-contrast microscope. Viability, plasma membrane integrity and acrosomal integrity were evaluated by the supravital staining, hypo-osmotic swelling test and normal acrosomal reaction, respectively. The highest (P<0.05) motility, acrosomal integrity and hypo-osmotic swelling response of spermatozoa was achieved by addition of 1.0 and 2.0mM BHT to semen extender. However, highest (P<0.05) viability of spermatozoa was achieved by inclusion of 2.0mM BHT. The higher concentration of BHT (3.0mM) reduced the motility, acrosomal integrity, viability and hypo-osmotic swelling response of the spermatozoa compared to other concentration used. In conclusion, BHT when added in the semen extender can improve the semen quality of buffalo bulls.

  1. Butylated hydroxytoluene chemoprevention of aflatoxicosis - effects on aflatoxin B(1) bioavailability, hepatic DNA adduct formation, and biliary excretion.

    PubMed

    Guarisco, J A; Hall, J O; Coulombe, R A

    2008-12-01

    The extreme sensitivity of turkeys to aflatoxin B(1) (AFB(1)) is associated with efficient hepatic cytochrome P-450 (P450)-mediated bioactivation, and deficient glutathione S-transferase (GST) mediated detoxification. Butylated hydroxytoluene (BHT) protects against AFB(1) toxicity in turkeys through mechanisms that include competitive inhibition of P450-mediated AFB(1) bioactivation. To test whether dietary BHT alters hepatic AFB(1)-DNA adduct formation, excretion, and bioavailability of AFB(1)in vivo, turkeys were given diets with BHT (4000ppm) for 10 days, given a single oral dose of [(3)H]-AFB(1) (0.05microg/g; 0.02microCi/g), then sampled at intervals up to 24h. Radiolabel in serum, red blood cells, liver, and breast meat was frequently lower in BHT-treated compared to control. Hepatic AFB(1)-DNA adducts in BHT-treated turkeys were significantly lower at 12 and 24h. BHT-fed birds had significant higher bile efflux, though biliary radiolabel excretion was not different from control. The amount of aflatoxin M(1) (AFM(1)) excreted in the bile was lower than in control, but BHT had no effect on the biliary excretion of AFB(1), aflatoxin Q(1) or glucuronide and sulfate conjugates. Thus, the chemopreventive properties of BHT may also occur through a reduction in AFB(1) bioavailability in addition to inhibition of bioactivation.

  2. Protective effects of Ligustrum lucidum fruit extract on acute butylated hydroxytoluene-induced oxidative stress in rats.

    PubMed

    Lin, H M; Yen, F L; Ng, L T; Lin, C C

    2007-04-20

    Nuzhenzi, the fruit of Ligustrum lucidum Ait. (Oleaceae), is commonly used as tonic for kidney and liver in the traditional Chinese medicine prescription. The present study aimed to investigate the antioxidant activities of ethanol extract of Ligustrum lucidum fruits (ELL) and its effects on butylated hydroxytoluene (BHT)-induced oxidative stress in rats. Results showed that ELL possesses weak antioxidant activities. Compared to the BHT (1000mg/kg)-treated group, results showed that ELL at 250, 500 and 1000mg/kg significantly reduced the levels of blood urea nitrogen (BUN), serum glutamic pyruvic transaminase (sGPT), glutamic oxaloacetic transaminase (sGOT), alkaline phosphatase (sALP), lactate dehydrogenase (LDH), triglyceride (TG) and creatinine (Cr), as well as LDH in bronchoalveolar lavage fluid (BALF). It also significantly decreased the level of lipid peroxides in liver and lung. In addition, ELL significantly enhanced the levels of catalase (CAT), superoxide dismutase (SOD) and glutathione peroxidase (GPx) in these organs. Histopathological evaluation of the tissues revealed that ELL reduced the incidence of lung lesions, while the liver and kidney tissues were not affected by BHT administration. Taken together, the protective effect of ELL against acute BHT-induced oxidative stress in rats could be through the upregulation of antioxidant enzymes.

  3. Protective effects of Ligustrum lucidum fruit extract on acute butylated hydroxytoluene-induced oxidative stress in rats.

    PubMed

    Lin, H M; Yen, F L; Ng, L T; Lin, C C

    2007-04-20

    Nuzhenzi, the fruit of Ligustrum lucidum Ait. (Oleaceae), is commonly used as tonic for kidney and liver in the traditional Chinese medicine prescription. The present study aimed to investigate the antioxidant activities of ethanol extract of Ligustrum lucidum fruits (ELL) and its effects on butylated hydroxytoluene (BHT)-induced oxidative stress in rats. Results showed that ELL possesses weak antioxidant activities. Compared to the BHT (1000mg/kg)-treated group, results showed that ELL at 250, 500 and 1000mg/kg significantly reduced the levels of blood urea nitrogen (BUN), serum glutamic pyruvic transaminase (sGPT), glutamic oxaloacetic transaminase (sGOT), alkaline phosphatase (sALP), lactate dehydrogenase (LDH), triglyceride (TG) and creatinine (Cr), as well as LDH in bronchoalveolar lavage fluid (BALF). It also significantly decreased the level of lipid peroxides in liver and lung. In addition, ELL significantly enhanced the levels of catalase (CAT), superoxide dismutase (SOD) and glutathione peroxidase (GPx) in these organs. Histopathological evaluation of the tissues revealed that ELL reduced the incidence of lung lesions, while the liver and kidney tissues were not affected by BHT administration. Taken together, the protective effect of ELL against acute BHT-induced oxidative stress in rats could be through the upregulation of antioxidant enzymes. PMID:17157464

  4. Enhancement of allergic responses in vivo and in vitro by butylated hydroxytoluene

    SciTech Connect

    Yamaki, Kouya; Taneda, Shinji; Yanagisawa, Rie; Inoue, Ken-ichiro; Takano, Hirohisa; Yoshino, Shin

    2007-09-01

    The effect of butylated hydroxytoluene (BHT), which is used widely as an antioxidant, on IgE-dependent allergic responses in vivo and in vitro was investigated. For in vivo study, passive cutaneous anaphylaxis (PCA) was elicited in rats by i.d. injection of anti-DNP IgE and 48 h later by i.v. injection of DNP-HSA. BHT was i.p. given immediately after anti-DNP IgE injection. For in vitro studies, the rat mast cell line RBL2H3 sensitized with monoclonal anti-dinitrophenol (DNP) IgE was challenged with the multivalent antigen DNP-human serum albumin (DNP-HSA) in the presence or absence of BHT. {beta}-Hexosaminidase and histamine released from RBL2H3 cells, as indicators of degranulation of the cells, the concentration of intracellular Ca{sup 2+}, the level of phosphorylated-Akt, and global tyrosine phosphorylation as indicators of mast cell activation, were measured. The results showed that BHT given to anti-DNP IgE-sensitized rats augmented DNP-specific PCA in a dose-dependent manner. In the presence of BHT, IgE-induced releases of {beta}-hexosaminidase and histamine from RBL2H3 cells were increased. BHT also further elevated IgE-mediated increased concentrations of intracellular Ca{sup 2+} and the levels of phosphorylated-Akt, but did not affect global tyrosine phosphorylation, in RBL2H3 cells. Moreover, the PI3K inhibitor LY294002 inhibited IgE-dependent degranulation and its enhancement by BHT. These findings indicate that BHT may upregulate PCA by enhancing mast cell degranulation associated with enhancements of intracellular Ca{sup 2+} concentration and PI3K activation, suggesting that BHT might affect allergic diseases such as allergic rhinitis and asthma.

  5. PASS-assisted design, synthesis and antioxidant evaluation of new butylated hydroxytoluene derivatives.

    PubMed

    Ariffin, Azhar; Rahman, Noorsaadah Abdul; Yehye, Wageeh A; Alhadi, Abeer A; Kadir, Farkaad A

    2014-11-24

    New multipotent antioxidants (MPAOs), namely 1,3,4-thiadiazoles and 1,2,4-triazoles bearing the well-known free radical scavenger butylated hydroxytoluene (BHT), were designed and synthesized using an acid-(base-) catalyzed intramolecular dehydrative cyclization reaction of the corresponding 1-acylthiosemicarbazides. The structure-activity relationship (SAR) of the designed antioxidants was performed along with the prediction of activity spectra for substances (PASS) training set. Experimental studies based on antioxidant activity using DPPH and lipid peroxidation assays verified the predictions obtained by the PASS-assisted design strategy. Compounds 4a-b, 5a-b and 6a-b showed an inhibition of stable DPPH free radicals at a 10(-4) M more than the well-known standard antioxidant BHT. Compounds with p-methoxy substituents (4b, 5b and 6b) were more active than o-methoxy substituents (4a, 5a and 6a). With an IC50 of 2.85 ± 1.09 μM, compound 6b exhibited the most promising in vitro inhibition of lipid peroxidation, inhibiting Fe(2+)-induced lipid peroxidation of essential oils derived from the egg yolk-based lipid-rich medium by 86.4%. The parameters for the drug-likeness of these BHT derivatives were also evaluated according to Lipinski's 'rule-of-five'. All of the BHT derivatives were found to violate one of Lipinski's parameters (Log P ≥ 5) even though they have been found to be soluble in protic solvents. The predictive TPSA and %ABS data allow for the conclusion that these compounds could have a good capacity for penetrating cell membranes. Therefore, these novel MPAOs containing lipophilic and hydrophilic groups can be proposed as potential antioxidants for tackling oxidative stress and lipid peroxidation processes.

  6. Effect of butylated hydroxytoluene (BHT) on the cryopreservation of common carp (Cyprinus carpio) spermatozoa.

    PubMed

    Öğretmen, F; İnanan, B E

    2014-12-30

    The aim of the present study was to test the effects of butylated hydroxytoluene (BHT) on the cryopreservation of common carp spermatozoa. BHT is widely used in the cryopreservation of the spermatozoa of different animal species and successfully sustains the characteristics of spermatozoa during freezing and thawing, but it has not previously been used with fish. After sampling, common carp spermatozoa were diluted with an extender composed of modified Kurokura's extender, 10% DMSO, and 10% egg yolk containing 0.0001, 0.001, 0.01, 0.1, 1, 2.5, 5, or 10mM BHT and subsequently frozen in liquid nitrogen. The post-thaw spermatozoa characteristics (i.e., progressive motility percentage (%), duration of progressive motility (s), fertilization rate (%), and eyed-eggs rate (%)) were evaluated and compared with those of the control group. There were significant increases in the percentage of progressive motility and the duration of progressive motility at the concentrations of 0.1 and 0.001mM BHT (P<0.05). The duration of post-thawed spermatozoa progressive motility at 0.001mM BHT was significantly greater than that of the other groups (39.6±0.4s, P<0.05), and the fertilization rates and eyed-eggs rates were also higher following the 0.1 and 1mM BHT treatments. BHT at concentrations of more than 1mM caused sperm immobility during the preparatory stages of the sperm freezing. We concluded that 0.001-0.1mM BHT can be beneficial for the cryopreservation of common spermatozoa.

  7. Toll-like receptor 4 in butylated hydroxytoluene-induced mouse pulmonary inflammation and tumorigenesis.

    PubMed

    Bauer, Alison K; Dixon, Darlene; DeGraff, Laura M; Cho, Hye-Youn; Walker, Christopher R; Malkinson, Alvin M; Kleeberger, Steven R

    2005-12-01

    Because chronic pulmonary diseases predispose to lung neoplasia, the identification of the molecular mechanisms involved could provide novel preventive, diagnostic, and therapeutic strategies. Toll-like receptors (TLRs) transduce exogenous and endogenous signals into the production of inflammatory cytokines to coordinate adaptive immune responses. To determine the role of Tlr4 in chronic lung inflammation, we compared lung permeability, leukocyte infiltration, and nuclear factor kappa B (NFkappaB) and activator protein 1 (AP-1) DNA binding in butylated hydroxytoluene (BHT)-treated (four weekly injections of 125-200 mg/kg each) inbred mouse strains with functional Tlr4 (OuJ and BALB) and mutated Tlr4 (HeJ and BALB(Lps-d)). We also measured primary tumor formation in these mice after single-carcinogen injection (3-methylcholanthrene; 10 microg/kg), followed by BHT treatment (six weekly injections of 125-200 mg/kg each). Mice with functional Tlr4 had reduced lung permeability, leukocyte inflammation, and primary tumor formation (BALB(Lps-d), mean = 22.3 tumors/mouse, versus BALB, mean = 13.9 tumors/mouse, difference = 8.4 tumors/mouse, 95% confidence interval = 4.6 to 12.1 tumors/mouse; P = .025) compared with mice with mutated Tlr4. NFkappaB DNA binding activity was higher in OuJ than in HeJ mice; however, AP-1 activity was elevated in HeJ mice. To our knowledge, this is the first model to demonstrate a modulatory role for Tlr4 in chronic lung inflammation and tumorigenesis.

  8. Enhancement of allergic responses in vivo and in vitro by butylated hydroxytoluene.

    PubMed

    Yamaki, Kouya; Taneda, Shinji; Yanagisawa, Rie; Inoue, Ken-ichiro; Takano, Hirohisa; Yoshino, Shin

    2007-09-01

    The effect of butylated hydroxytoluene (BHT), which is used widely as an antioxidant, on IgE-dependent allergic responses in vivo and in vitro was investigated. For in vivo study, passive cutaneous anaphylaxis (PCA) was elicited in rats by i.d. injection of anti-DNP IgE and 48 h later by i.v. injection of DNP-HSA. BHT was i.p. given immediately after anti-DNP IgE injection. For in vitro studies, the rat mast cell line RBL2H3 sensitized with monoclonal anti-dinitrophenol (DNP) IgE was challenged with the multivalent antigen DNP-human serum albumin (DNP-HSA) in the presence or absence of BHT. beta-Hexosaminidase and histamine released from RBL2H3 cells, as indicators of degranulation of the cells, the concentration of intracellular Ca2+, the level of phosphorylated-Akt, and global tyrosine phosphorylation as indicators of mast cell activation, were measured. The results showed that BHT given to anti-DNP IgE-sensitized rats augmented DNP-specific PCA in a dose-dependent manner. In the presence of BHT, IgE-induced releases of beta-hexosaminidase and histamine from RBL2H3 cells were increased. BHT also further elevated IgE-mediated increased concentrations of intracellular Ca2+ and the levels of phosphorylated-Akt, but did not affect global tyrosine phosphorylation, in RBL2H3 cells. Moreover, the PI3K inhibitor LY294002 inhibited IgE-dependent degranulation and its enhancement by BHT. These findings indicate that BHT may upregulate PCA by enhancing mast cell degranulation associated with enhancements of intracellular Ca2+ concentration and PI3K activation, suggesting that BHT might affect allergic diseases such as allergic rhinitis and asthma.

  9. Binding properties of butylated hydroxytoluene with calf thymus DNA in vitro.

    PubMed

    Ma, Yadi; Pan, Junhui; Zhang, Guowen; Zhang, Yue

    2013-09-01

    The binding properties of butylated hydroxytoluene (BHT) with calf thymus DNA (ctDNA) in simulated physiological buffer (pH 7.4) were investigated using ethidium bromide (EB) dye as a fluorescence probe by various spectroscopic techniques including UV-vis absorption, fluorescence, circular dichroism (CD), and Fourier transform infrared (FT-IR) spectroscopy along with ctDNA melting studies and viscosity measurements. It was found that the binding of BHT to ctDNA could decrease the absorption intensity of ctDNA, significantly increase melting temperature and relative viscosity of ctDNA, and induce the changes in CD spectra. Moreover, the competitive binding studies showed that BHT was able to displace EB from the bound ctDNA-EB complex. All the experimental results indicated that the binding mode between BHT and ctDNA was an intercalation. The association constants between BHT and ctDNA were evaluated to be (4.78±0.04)×10(3), (2.86±0.02)×10(3) and (1.80±0.04)×10(3) L mol(-)(1) at 298, 304, 310K, respectively. Further, the FT-IR analysis revealed that BHT was more prone to interact with adenine and thymine base pairs, and no significant conformational transition of ctDNA occurred. Thermodynamic analysis of the binding data showed that the binding process was primarily driven by hydrogen bonds and van der Waals forces, as the values of the enthalpy change and the entropy change were calculated to be -62.47±0.07kJ mol(-)(1) and -139.22±0.22J mol(-)(1) K(-)(1), respectively.

  10. Consequences of butylated hydroxytoluene in the freezing extender on post-thaw characteristics of stallion spermatozoa in vitro.

    PubMed

    Morillo-Rodríguez, A; Macías-García, B; Tapia, J A; Ortega-Ferrusola, C; Peña, F J

    2012-05-01

    Ejaculates from six pure Spanish stallions were split, and one subsample frozen in a commercial extender supplemented with the lipid soluble antioxidant butylated hydroxytoluene (BHT), while the other subsample served as control. After at least 4 weeks of storage, samples were thawed and post-thaw sperm quality analysed: sperm motility and kinematics using a CASA system, membrane and acrosome integrity and mitochondrial membrane potential using flow cytometry. The outcome of cryopreservation varied significantly among stallions. However, the supplementation with 1 mm BHT had no significant effect on any of the sperm parameters evaluated post-thaw.

  11. Analysis of the antioxidant butylated hydroxytoluene (BHT) in water by means of solid phase extraction combined with GC/MS.

    PubMed

    Fries, Elke; Püttmann, Wilhelm

    2002-05-01

    The antioxidant 3,5-di-tert-butyl-4-hydroxy-toluene (BHT) is widely used as an additive to increase the tenability of food and plastics. BHT is degraded to 3,5-di-tert-butyl-4-hydroxybenzaldehyde (BHT-CHO) in mammals, as well as in the natural environment such as in water and soils. BHT-CHO has been studied extensively in terms of their potential toxicities. The present investigation was carried out to quantify BHT and BHT-CHO in river, ground, rain and drinking water obtained from several locations in Germany. Apart from the compounds mentioned above, 1,2-bis-(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (2-BHT), which is a dimer of BHT, was also detected in the extracts of some ground water samples. The applied analytical method is based on solid phase extraction (SPE) to concentrate trace compounds from water samples followed by gas chromatography/mass spectrometry (GC/MS) of the extracts. A total of 51 of the respective water samples were used for extraction purposes and analyte recoveries were all > or = 80%. The determination limit for BHT was 5 ng l(-1) and for BHT-CHO 16 ng l(-1). The standard deviations for the analytical procedure were 6% for BHT and 10% for BHT-CHO. The use of the antioxidant BHT in Germany has resulted in water concentrations of 7-791 ng l(-1) in the rivers Rhine, Elbe, Main, Oder, Nidda and Schwarzbach. The degradation product BHT-CHO was also detected in the river water samples at concentrations between 29 and 223 ng l(-1). The concentrations of BHT measured in German rivers are lower compared to values measured in the USA and Japan 20 years ago. In ground water, levels for BHT varied from non-detectable up to 2156 ng l(-1) and for BHT-CHO from non-detectable up to 674 ng l(-1). Both compounds were also detected in rain water in Frankfurt/Main at a concentration of 1797 ng l(-1) for BHT and 59 ng l(-1) for BHT-CHO. PMID:12108724

  12. Analysis of the antioxidant butylated hydroxytoluene (BHT) in water by means of solid phase extraction combined with GC/MS.

    PubMed

    Fries, Elke; Püttmann, Wilhelm

    2002-05-01

    The antioxidant 3,5-di-tert-butyl-4-hydroxy-toluene (BHT) is widely used as an additive to increase the tenability of food and plastics. BHT is degraded to 3,5-di-tert-butyl-4-hydroxybenzaldehyde (BHT-CHO) in mammals, as well as in the natural environment such as in water and soils. BHT-CHO has been studied extensively in terms of their potential toxicities. The present investigation was carried out to quantify BHT and BHT-CHO in river, ground, rain and drinking water obtained from several locations in Germany. Apart from the compounds mentioned above, 1,2-bis-(3,5-di-tert-butyl-4-hydroxyphenyl)ethane (2-BHT), which is a dimer of BHT, was also detected in the extracts of some ground water samples. The applied analytical method is based on solid phase extraction (SPE) to concentrate trace compounds from water samples followed by gas chromatography/mass spectrometry (GC/MS) of the extracts. A total of 51 of the respective water samples were used for extraction purposes and analyte recoveries were all > or = 80%. The determination limit for BHT was 5 ng l(-1) and for BHT-CHO 16 ng l(-1). The standard deviations for the analytical procedure were 6% for BHT and 10% for BHT-CHO. The use of the antioxidant BHT in Germany has resulted in water concentrations of 7-791 ng l(-1) in the rivers Rhine, Elbe, Main, Oder, Nidda and Schwarzbach. The degradation product BHT-CHO was also detected in the river water samples at concentrations between 29 and 223 ng l(-1). The concentrations of BHT measured in German rivers are lower compared to values measured in the USA and Japan 20 years ago. In ground water, levels for BHT varied from non-detectable up to 2156 ng l(-1) and for BHT-CHO from non-detectable up to 674 ng l(-1). Both compounds were also detected in rain water in Frankfurt/Main at a concentration of 1797 ng l(-1) for BHT and 59 ng l(-1) for BHT-CHO.

  13. The metabolism of 3,5-di-tert.-butyl-4-hydroxytoluene in the rat and in man

    PubMed Central

    Daniel, J. W.; Gage, J. C.; Jones, D. I.

    1968-01-01

    1. The major metabolites of 3,5-di-tert.-butyl-4-hydroxytoluene (BHT) in the rat are 3,5-di-tert.-butyl-4-hydroxybenzoic acid (BHT-acid), both free (9% of the dose) and as a glucuronide (15%), and S-(3,5-di-tert.-butyl-4-hydroxybenzyl)-N-acetylcysteine. 2. The mercapturic acid does not appear to derive from the usually accepted enzyme mechanism, and may involve a non-enzymic reaction between BHT free radical and cysteine. 3. The ester glucuronide and mercapturic acid found in rat urine are also the major metabolites in rat bile and must be responsible for the enterohepatic circulation. 4. Free BHT-acid is the main component in rat faeces. 5. In man, BHT-acid, free and conjugated, is a minor component in urine, and the mercapturic acid is virtually absent. The bulk of the radioactivity is excreted as the ether-insoluble glucuronide of a metabolite in which the ring methyl group and one tert.-butyl methyl group are oxidized to carboxyl groups, and a methyl group on the other tert.-butyl group is also oxidized, probably to an aldehyde group. 6. These differences in metabolism by the rat and by man are sufficient to account for the difference in excretion by the two species. PMID:5637363

  14. Protein damage from electrophiles and oxidants in lungs of mice chronically exposed to the tumor promoter butylated hydroxytoluene.

    PubMed

    Shearn, Colin T; Fritz, Kristofer S; Thompson, John A

    2011-07-15

    The food additive butylated hydroxytoluene (BHT) promotes tumorigenesis in mouse lung. Chronic BHT exposure is accompanied by pulmonary inflammation and several studies indicate that elevated levels of reactive oxygen species (ROS) are involved in its promoting activity. The link between BHT and elevated ROS involves formation of quinone methide (QM) metabolites; these electrophiles form adducts with a variety of lung proteins including several enzymes that protect cells from oxidative stress. Studies in vitro demonstrated that QM alkylation of cytoprotective enzymes is accompanied by inactivation, so an objective of the present investigation was to determine if inactivation also occurs in vivo. Two groups of mice were exposed to BHT by intraperitoneal injection, one for 10 days and the other for 24 days, and proteins from lung cytosols were examined for damage. Analysis by Western blotting demonstrated that BHT treatment caused substantial increases in protein carbonylation, nitration and adduction by 4-hydroxynonenal, confirming the occurrence of sustained oxidative and nitrosative stress over the treatment period required for tumor promotion. Effects of BHT on the activities and/or levels of a representative group of antioxidant/protective enzymes in mouse lung also were assessed; NAD(P)H:quinone reductase and glutathione reductase were unaffected, however carbonyl reductase activity decreased 50-60%. Superoxide dismutase and glutathione peroxidase activities increased 2- and 1.5-fold, respectively, and glutamate-cysteine ligase catalytic subunit expression increased 32-39% relative to untreated mice. Glutathione S-transferase (GST) activity decreased 50-60% but concentrations of the predominant isoforms, GSTM1 and P1, were not affected. GSTP1 was substantially more susceptible than M1 to adduction and inhibition by treatment with BHT-QM in vitro, suggesting that lower GST activity in mice after BHT treatment is due to adduction of the P1 isoform. The results of

  15. Selective induction of apoptosis in mouse and human lung epithelial cell lines by the tert-butyl hydroxylated metabolite of butylated hydroxytoluene: a proposed role in tumor promotion.

    PubMed

    Dwyer-Nield, L D; Thompson, J A; Peljak, G; Squier, M K; Barker, T D; Parkinson, A; Cohen, J J; Dinsdale, D; Malkinson, A M

    1998-09-15

    Butylated hydroxytoluene (BHT) causes lung injury in mice and promotes tumor formation. Hydroxylation of a tert-butyl group on BHT to yield the metabolite, 6-tert-butyl-2-[2'-(2'-hydroxymethyl)-propyl]-4-methylphenol (BHTOH), may be required. BHTOH is more potent than BHT on an equimolar basis in causing lung damage, enhancing lung tumor development, killing isolated bronchiolar non-ciliated Clara cells, and inhibiting lung epithelial gap junctional intercellular communication. One mechanism proposed for tumor promoting agents is selective cytotoxicity; killing normal cells allows uninhibited clonal expansion of neighboring initiated cells. We compared the abilities of BHT, BHTOH, and other BHT metabolites to kill non-tumorigenic and tumorigenic mouse and human lung cell lines, and examined the contribution of apoptosis to this cytotoxicity. These cells lack the cytochrome P450 2B isozyme necessary for converting BHT to BHTOH. BHTOH and 4-hydroperoxy-4-methyl-2,6-di-tert-butyl-2,5-cyclohex-adienone+ ++ (BHTOOH) were most toxic, BHT and 2,6-di-tert-butyl-1,4-benzoquinone (BHTQu) were less potent, and 4-methyl BHT metabolites that are not pneumotoxic were ineffective. BHTOH most strongly induced apoptosis, based on nuclear condensation and transmission electron microscopy. Non-tumorigenic cells were as susceptible to cell death as the neoplastic cell lines when apoptosis and necrosis are not distinguished, but more sensitive to BHTOH-induced apoptosis. An apoptotic mechanism may underlie the lung tumor promoting actions of BHTOH.

  16. Effects of the butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) on the arylamines N-acetyltransferase activity in rat white blood cells.

    PubMed

    Lu, H F; Wu, H C; Chang, W C; Chung, J G

    1999-01-01

    Butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) were used to determine any effects on the N-acetyltransferase (NAT) activity in rat whole blood and white blood cells as measured by high performance liquid chromatography assay for the amounts of N-acetyl-2-aminofluorene (AAF) and 2-aminofluorene (AF). Two assay systems were performed, one with cellular cytosols, the other with intact white blood cells. The NAT activity in the whole blood and white blood cell cytosols was suppressed by BHA and BHT in a dose-dependent manner, i.e. the higher the concentrations of BHA and BHT, the higher the inhibition of NAT activity. Time-course experiments showed that NAT activity measured from the intact white blood cells was inhibited by BHA and BHT up to 24 h. The results suggest that BHA and BHT suppressed AF acetylation in rat blood with intact white blood cells.

  17. Application of solid-phase microextraction combined with gas chromatography-mass spectrometry to the determination of butylated hydroxytoluene in bottled drinking water.

    PubMed

    Tombesi, Norma B; Freije, Hugo

    2002-07-19

    Butylated hydroxytoluene (BHT) is an antioxidant utilized as additive in foods and packaging plastic. Its presence in drinking water is possible if it is used as an antioxidant in the packaging plastic because it may migrate into the package's contents. A method for the determination of BHT in water by means of solid-phase microextraction and gas chromatography-mass spectrometry has been developed and evaluated with respect to the time of fiber exposure, limits of detection and quantitation, linearity and precision. Finally, the method was applied to evaluate the presence of this substance in samples of mineral and mineralized bottled drinking water, and it appeared to be present in seven out of a total of fifteen commercial brands.

  18. Enhancement of lung tumor formation in mice by dietary butylated hydroxytoluene: dose-time relationships and cell kinetics

    SciTech Connect

    Witschi, H.R.; Morse, C.C.

    1983-10-01

    Strain A/J mice given injections of 1000 mg urethan/kg and fed for 12 weeks a diet containing 0.75% of butylated hydroxytoluene (BHT) had significantly more tumors per lung 4 or 9 months later than animals given urethan and fed a control diet. A 2-week exposure to dietary BHT (0.75%) was sufficient to significantly enhance tumor development, and the lowest effective BHT concentration was 0.1%, fed for 8 weeks. Tumor development was also enhanced in animals treated once with 3-methylcholanthrene, benzo(a)pyrene, or N-nitrosodimethylamine and, beginning 24 hours later, fed BHT for 8 weeks. Cell kinetic studies showed that BHT given in the diet produced increased proliferation of type II alveolar cells during the first 2 weeks and that initial cell proliferation was delayed in urethan-treated animals.

  19. New analogues of butylated hydroxytoluene as anti-inflammatory and antioxidant agents.

    PubMed

    Ziakas, George N; Rekka, Eleni A; Gavalas, Antonios M; Eleftheriou, Phaedra T; Kourounakis, Panos N

    2006-08-15

    Amine or amide derivatives bearing the 2,6-di-tert-butyl phenol moiety are synthesised. Almost all are antioxidants, reduce acute inflammation and inhibit COX-1 and lipoxygenase activity. The most potent anti-inflammatory, COX-1 inhibitor and antioxidant agent, with low toxicity, is 2,6-di-tert-butyl-4-thiomorpholin-4-ylmethyl-phenol.

  20. Effects of butylated hydroxyanisole and butylated hydroxytoluene on DNA adduct formation and arylamine N-acetyltransferase activity in human bladder tumour cells.

    PubMed

    Lu, Hsueh-Fu; Wu, Hsi-Chin; Hsia, Te-Chun; Chen, Wen-Chi; Hung, Chi-Fu; Chung, Jing-Gung

    2002-01-01

    In this study, butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) were used to determine the inhibition of arylamine N-acetyltransferase (NAT) activity and DNA adduct formation in human bladder tumour cell line T-24. The activity of NAT was measured by high-performance liquid chromatography, assaying for the amounts of N-acetyl-2-aminofluorene and N-acetyl-p-aminobenzoic acid and remaining 2-aminofluorene and p-aminobenzoic acid. Human bladder tumour cell line T-24 cytosols and intact cells were used for examining NAT activity and carcinogen-DNA adduct formation. The results demonstrated that NAT activity and 2-aminofluorene-DNA adduct formation in human bladder tumour cells were inhibited and decreased by BHA and BHT in a dose-dependent manner. The effects of BHA and BHT on the values of the apparent K(m) and V(max) also were determined in both systems examined. The results indicated that BHA and BHT decreased the apparent values of K(m) and V(max) from human bladder tumour cells in both cytosol and intact cells.

  1. Effects of the butylated hydroxyanisole and butylated hydroxytoluene on the DNA adduct formation and arylamines N-acetyltransferase activity in human colon tumor cells.

    PubMed

    Chang, S H; Chen, G W; Yeh, C C; Hung, C F; Lin, S S; Chung, J G

    2001-01-01

    The effects of butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) on N-acetyltransferase (NAT) activity were examined using a human colon tumor cell line (colo 205). BHA or BHT were added to the cytosols or to the medium of human colon tumor cells: The NAT activity was measured by high performance liquid chromatography, assaying the amounts of acetylated 2-aminoflluorene (AAF), p aminobenzoic acid (N-Ac-PABA), nonacetylated 2 aminofluorene (AF) and p-aminobenzoic acid (PABA). The NAT activity in the human colon tumor cells and cytosols was suppressed by BHA or BHT in a dose-dependent manner. The apparent values of Km and Vmax of NAT of human colon tumor cells were also decreased by BHA or BHT in cytosols and in intact cells. BHA or BHT may act as a noncompetitive inhibitor. After the incubation of human colon tumor cells with AF in the presence of BHA or BHT, the cells were recovered and DNA was prepared and hydrolysed to nucleotides. Adducted nucleotides were extracted into butanol and AF-DNA adducts were analysed by HPLC. The results also demonstrated that when BHA or BHT was added to the media, a decrease in AF-DNA adduct formation was seen in the human colon tumor cells. The finding of AF-DNA adduct formation in cultured human colon tumor cells suggest the possibility of using cultured cells for assessing arylamine-induced DNA damage.

  2. Responses of tumorigenic and non-tumorigenic mouse lung epithelial cell lines to electrophilic metabolites of the tumor promoter butylated hydroxytoluene.

    PubMed

    Sun, Yude; Dwyer-Nield, Lori D; Malkinson, Alvin M; Zhang, Yan Ling; Thompson, John A

    2003-03-01

    A model system to investigate the promotion phase of pulmonary carcinogenesis involves chronic exposure of carcinogen-initiated mice to the food additive, butylated hydroxytoluene (BHT). Previous studies strongly suggested that this activity is due to the cytochrome p450-catalyzed formation of quinone methides 2,6-di-tert-butyl-4-methylenecyclohexa-2,5-dienone (BHT-QM) and 6-tert-butyl-2-(1',1'-dimethyl-2'-hydroxy)ethyl-4-methylenecyclohexa-2,5-dienone (BHTOH-QM). The effects of these electrophiles on non-tumorigenic C10 and E10 epithelial cell lines derived from a normal mouse lung explant were compared with effects on their corresponding neoplastic siblings, the A5 and E9 spontaneous transformants, respectively. The tumorigenic cells were more resistant to cell killing, with LC(50) values of 165-180 microM for BHT-QM and 12-22 microM for BHTOH-QM, versus LC(50) values in the non-tumorigenic cells of 105-118 microM and 5.0-6.0 microM, respectively. Constitutive glutathione (GSH) concentrations were 12-20 nmol/10(6) cells, and BHT-QM toxicity was enhanced >2-fold by depleting GSH with buthionine sulfoximine (BSO). Formation of the GSH conjugate of BHT-QM accounted for a substantial fraction of the cellular GSH lost by quinone methide exposure. Enhanced lipid peroxidation and superoxide formation occurred in all cell lines treated with BHT-QM, but both tumorigenic lines contained higher levels of GSH S-transferase and superoxide dismutase (SOD) activities. These data suggest the possibility that BHT-derived quinone methides may exert their promoting effects by inducing oxidative stress; such stress is better tolerated by tumorigenic cells, which have higher levels of antioxidant enzymes. Normal cells are destroyed more readily which allows neoplastic cells to expand their proliferation.

  3. Simultaneous determination of butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) in food samples using a carbon composite electrode modified with Cu(3)(PO(4))(2) immobilized in polyester resin.

    PubMed

    Freitas, Kellen Heloizy Garcia; Fatibello-Filho, Orlando

    2010-05-15

    A simple electrochemical method was developed for the single and simultaneous determination of butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT) in food samples using square-wave voltammetry (SWV). A carbon composite electrode modified (MCCE) with copper (II) phosphate immobilized in a polyester resin was proposed. The modified electrode allowed the detection of BHA and BHT at potentials lower than those observed at unmodified electrodes. A separation of about 430mV between the peak oxidation potentials of BHA and BHT in binary mixtures was obtained. The calibration curves for the simultaneous determination of BHA and BHT demonstrated an excellent linear response in the range from 3.4x10(-7) to 4.1x10(-5)molL(-1) for both compounds. The detection limits for the simultaneous determination of BHA and BHT were 7.2x10(-8) and 9.3x10(-8)molL(-1), respectively. In addition, the stability and repeatability of the electrode were determined. The proposed method was successfully applied in the simultaneous determination of BHA and BHT in several food samples, and the results obtained were found to be similar to those obtained using the high performance liquid chromatography method with agreement at 95% confidence level.

  4. Rejuvenescence and extension of an urochordate life span following a single, acute administration of an anti-oxidant, butylated hydroxytoluene.

    PubMed

    Voskoboynik, Ayelet; Reznick, Abraham Z; Rinkevich, Baruch

    2002-05-01

    Two commonly accepted metabolic theories of aging interpret senescence either in terms of the rate of living, where a fixed total metabolic potential is consumed over an expected lifetime (after which the organism wears out and dies) or, in terms of accumulative oxidative damage resulting in progressive and irreversible changes in metabolic pathways. Protocols based on restricted diets, chronically administered anti-oxidants and the use of established lines of organisms resistant to free radical damage support the metabolic theories of aging by revealing, in many cases, significant extensions of life spans or dramatic anti-aging effects. To test the universality of these metabolic hypotheses of aging, we acutely treated ramets (clonal replicates) from old, long-lived colonies of the urochordate Botryllus schlosseri with lethal doses of the anti-oxidant butylated hydroxytoluene (BHT). This group of organisms has a weekly cyclical and highly synchronized developmental process (blastogenesis), during which all existing zooids are removed by massive apoptosis and phagocytosis processes. In animals treated with BHT, blastogenesis was completely arrested and colonies deteriorated to a morphologically chaotic state. Rescued ramets resorbed BHT treated zooids, regenerated entirely new sets of zooids and then revealed: (1) rejuvenescence and enhanced growth rates and in many cases, (2) up to 4.6 times extension of post-treatment life expectancy. Both metabolic theories for senescence were therefore falsified in B. schlosseri. The possible existence of an aging clock that can be set by the environment is suggested.

  5. Release of butylated hydroxytoluene from an active film packaging to Asadero cheese and its effect on oxidation and odor stability.

    PubMed

    Soto-Cantú, C D; Graciano-Verdugo, A Z; Peralta, E; Islas-Rubio, A R; González-Córdova, A; González-León, A; Soto-Valdez, H

    2008-01-01

    Antioxidant active packaging consisting of coextruded films made of low density polyethylene (LDPE) added with 0, 8, and 14 mg/g of butylated hydroxytoluene (BHT) and polyamide 6/66 were fabricated. The release of BHT from the films to Asadero cheese was determined. Most of the BHT was diffused from the LDPE layer to the cheese during the first 20 d of storage at 5 degrees C. Diffusion coefficient for the diffusion of BHT from the films 8 and 14 to the cheese was calculated as 6.24E-12 and 6.26E-12 cm2/s, respectively. The release of BHT from the film added with 8 mg/g of the antioxidant in the LDPE layer complied with the legal limit established for food products. However, the film added with 14 mg/g of the antioxidant exceeded that limit. The film added with 8 mg/g of BHT maintained the same levels of oxidized odor from 20 to 100 d of storage.

  6. Influence of butylated hydroxytoluene-induced cell proliferation on mouse lung damage after x rays or fission neutrons

    SciTech Connect

    Ullrich, R.L.; Meyer, K.R.

    1982-02-01

    To examine the relative importance of endothelial cells vs type II alveolar cells in the development of lung damage, we irradiated the lungs of mice with X rays either 2 or 6 days after treatment with butylated hydroxytoluene (BHT) and determined LD/sub 50///sub 180/ values. LD/sub 50///sub 180/ was 959 rad when no BHT was given, 269 rad when 2 days elapsed after BHT treatment, and 1445 rad at 6 days after BHT. The pattern of response was similar after fission neutron irradiation to the thorax. LD/sub 50///sub 180/ after fission neutrons alone was 476 rad, but at 2 and 6 days after BHT, the LD/sub 50///sub 180/ values were 98 and 575 rad, respectively. Clearly 2 days after BHT, when radiation injury to type II cells predominated, the sensitivity to both X rays and fission neutrons increased markedly, suggesting that injury to alveolar epithelial cells may be of primary importance in the development of lung damage in the mouse. Further, since certain antineoplastic drugs may induce a proliferative response in the lung similar to that produced by BHT, these data stress the fact that the timing between chemotherapy and radiation may be critical in the treatment of some cancers to avoid serious complications.

  7. Comparison of antioxidant effects of milk mineral, butylated hydroxytoluene and sodium tripolyphosphate in raw and cooked ground pork.

    PubMed

    Jayasingh, Preetha; Cornforth, Daren P

    2004-01-01

    The antioxidant effects of 0.5-2.0% milk mineral (MM) was tested in raw and cooked ground pork stored at 2 °C or -20 °C, compared to butylated hydroxytoluene (BHT) and sodium tripolyphosphate (STP). TBA numbers were low and not different between raw meat treatments. TBA numbers were lower (P<0.01) for cooked treatments with MM or STP compared to controls or treatments with BHT. Experiments were also done to determine acceptability of pork samples with various TBA values, and to determine effect of holding time before serving on TBA values. Cooked pork patties held at 71 °C for 90 or 120 min had higher (P<0.05) TBA values than patties held for 0-60 min. Thus patties could be warmed for 60 min after cooking without significantly increasing TBA number. For paired-preference sensory testing, patties were cooked and stored at 2 °C for 0, 1, 2 and 3 days to obtain TBA numbers of 0.4, 1.5, 3.4 and 3.9 respectively. Panelists preferred (P<0.001) patties with TBA number <0.5, compared to patties with TBA numbers >1.4.

  8. Attenuation of the pulmonary inflammatory response following butylated hydroxytoluene treatment of cytosolic phospholipase A2 null mice.

    PubMed

    Meyer, Amy M; Dwyer-Nield, Lori D; Hurteau, Gregory; Keith, Robert L; Ouyang, Yanli; Freed, Brian M; Kisley, Lori R; Geraci, Mark W; Bonventre, Joseph V; Nemenoff, Raphael A; Malkinson, Alvin M

    2006-06-01

    Administration of butylated hydroxytoluene (BHT) to mice causes lung damage characterized by the death of alveolar type I pneumocytes and the proliferation and subsequent differentiation of type II cells to replace them. Herein, we demonstrate this injury elicits an inflammatory response marked by chemokine secretion, alveolar macrophage recruitment, and elevated expression of enzymes in the eicosanoid pathway. Cytosolic phospholipase A(2) (cPLA(2)) catalyzes release of arachidonic acid from membrane phospholipids to initiate the synthesis of prostaglandins and other inflammatory mediators. A role for cPLA(2) in this response was examined by determining cPLA(2) expression and enzymatic activity in distal respiratory epithelia and macrophages and by assessing the consequences of cPLA(2) genetic ablation. BHT-induced lung inflammation, particularly monocyte infiltration, was depressed in cPLA(2) null mice. Monocyte chemotactic protein-1 (MCP-1) content in bronchoalveolar lavage fluid increases after BHT treatment but before monocyte influx, suggesting a causative role. Bronchiolar Clara cells isolated from cPLA(2) null mice secrete less MCP-1 than Clara cells from wild-type mice, consistent with the hypothesis that cPLA(2) is required to secrete sufficient MCP-1 to induce an inflammatory monocytic response.

  9. Effect of butylated hydroxytoluene (E321) pretreatment versus L-arginine on liver injury after sub-lethal dose of endotoxin administration.

    PubMed

    Engin, Ayse Basak; Bukan, Neslihan; Kurukahvecioglu, Osman; Memis, Leyla; Engin, Atilla

    2011-11-01

    Aim of this study was to compare the effects of L-arginine (L-arg) and food-antioxidant butylated hydroxytoluene (BHT) against oxidative stress of Escherichia coli endotoxin (LPS) in liver. Ninety Wistar albino rats were assigned in three groups. Rats received one of the following pre-treatment previous to 5mg/kg LPS intraperitoneally: saline, L-arg (NO donor, 100mg/kg) or BHT (250 mg/kg/day), for 3 days. At second, fourth and sixth hours, plasma nitrite-plus-nitrate, circulating liver enzymes, glutathione levels, superoxide dismutase, glutathione peroxidase activities were measured. The most remarkable liver injury was evident in BHT pre-treated animals at all time points compared to L-arg pre-treated rats. While BHT enhanced superoxide dismutase activities following LPS, glutathione decreased simultaneously compared to L-arg group. Although the risk associated with the use of BHT alone in subthreshold doses appeared to be low, higher risk of liver toxicity should be considered when over-consuming this food additive in endotoxemic settings.

  10. Protective effect of butylated hydroxytoluene on ferric nitrilotriacetate induced hepatotoxicity and oxidative stress in mice.

    PubMed

    Ansar, S; Tabassum, H; Al Jameil, N

    2013-05-01

    The present study was undertaken to evaluate the possible ameliorating effect of butylated hydroxyl toluene (BHT), associated with ferric nitrilotriacetate (Fe-NTA)-induced oxidative stress and liver injury in mice. The treatment of mice with Fe-NTA alone enhances ornithine decarboxylase activity to 4.6 folds, protein carbonyl formation increased up to 2.9 folds and DNA synthesis expressed in terms of [(3)H] thymidine incorporation increased to 3.2 folds, and antioxidants and antioxidant enzymes decreased to 1.8-2.5 folds, compared with the corresponding saline-treated controls. These changes were reversed significantly (p < 0.001) in animals receiving a pretreatment of BHT. Our data show that BHT can reciprocate the toxic effects of Fe-NTA and can serve as a potent chemopreventive agent.

  11. Effect of butylated hydroxytoluene (BHT) on the aerobic biodegradation of a model vegetable oil in aquatic media.

    PubMed

    Salam, Darine A; Suidan, Makram T; Venosa, Albert D

    2012-06-19

    Antioxidants added to vegetable oils to prevent lipid oxidation significantly affect their biodegradation in impacted aquatic environments. In this study, the effect of butylated-hydroxytoluene (BHT) on the biodegradation of glyceryl trilinoleate, a model vegetable oil highly susceptible to autoxidation, was determined. Biodegradation experiments were conducted in respirometric microcosms at an oil loading of 333 gal acre(-1) (0.31 L m(-2)) and BHT concentrations ranging from 0 to 800 mg kg(-1) (0, 50, 100, 200, 400, and 800 mg kg(-1)). Competition between polymerization and biodegradation of the oil was observed at all BHT concentrations and was significant in the microcosms not supplemented with the antioxidant. In all microcosms, intractable rigid polymers unavailable for bacterial degradation were formed. Infrared analysis evidenced the advanced stages of the oil autoxidation. After 19 weeks of incubation, only about 41% of the oil was mineralized in the microcosms with no BHT. However, mineralization exceeded 67% in the microcosms with added antioxidant and did not significantly increase with increasing BHT concentrations. Biodegradation rate constants were calculated by nonlinear regression and were not significantly different in the microcosms with added BHT (k = 0.001 h(-1)). Higher k values were measured in the microcosms lacking the antioxidant (k = 0.0023 h(-1)), most likely due to the increased oxygen consumption associated with the autoxidation process in this case. No toxicity was detected in all biotic microcosms at the end of the incubation period, while high toxicity (EC(50) = 4.78%) was measured in the abiotic blanks with no antioxidant and was attributed to the accumulation of autoxidation products.

  12. Effect of butylated hydroxytoluene, curcumin, propyl gallate and thiabendazole on cytochrome P450 forms in cultured human hepatocytes.

    PubMed

    Price, R J; Scott, M P; Giddings, A M; Walters, D G; Stierum, R H; Meredith, C; Lake, B G

    2008-06-01

    1. The objective of this study was to investigate the effects of four food chemicals, namely butylated hydroxytoluene (BHT), curcumin (CC), propyl gallate (PG) and thiabendazole (TB), on cytochrome P450 (CYP) forms in cultured human hepatocytes. 2. Treatment of human hepatocytes for 72 h with 2-200 microM TB produced concentration-dependent increases in CYP1A2, CYP2B6 and CYP3A4 mRNA levels, whereas treatment with BHT increased CYP2B6 and CYP3A4 mRNA levels. CYP1A2, CYP2B6 and CYP3A4 mRNA levels were induced around 48-, 21- and 9-fold, respectively, by 200 microM TB, with CYP2B6 and CYP 3A4 mRNA levels being induced around 12- and 7-fold, respectively, by 200 microM BHT. 3. In contrast, the treatment of human hepatocytes for 72 h with PG and CC had little or no effect on CYP mRNA levels. 4. The treatment of human hepatocytes with TB also induced CYP1A-dependent 7-ethoxyresorufin O-deethylase activity, whereas BHT induced CYP3A-dependent testosterone 6beta-hydroxylase activity. 5. In summary, the results demonstrate that TB is a mixed inducer of CYP forms in human hepatocytes inducing CYP1A, CYP2B and CYP3A forms, whereas BHT is an inducer of CYP2B and CYP3A forms.

  13. Quantitative trait locus mapping of susceptibilities to butylated hydroxytoluene-induced lung tumor promotion and pulmonary inflammation in CXB mice.

    PubMed

    Malkinson, Alvin M; Radcliffe, Richard A; Bauer, Alison K

    2002-03-01

    We have reported previously [Bauer,A.K. et al. (2001) Exp. Lung Res., 27, 197-216] that the 13 CXB recombinant inbred mouse strains derived from BALB/cByJ and C57BL/6J progenitors vary in their responsiveness to both lung tumor promotion and pulmonary inflammation induced by chronic administration of butylated hydroxytoluene (BHT). Herein we have applied these data, along with markers known to be polymorphic among these strains, to conduct linkage analysis of these susceptibilities. This enabled us to assign provisional quantitative trait loci (QTL) that govern these strain variations in susceptibility as a genetic approach to assessing the influence of inflammation on tumorigenesis. A Chr 15 (39.1-55.6 cM) QTL regulated susceptibility to two-stage carcinogenesis, a protocol in which chronic BHT exposure followed a single urethane injection; a similar QTL on Chr 15 (46.7-61.7 cM) influenced BHT induction of cyclooxygenase-2 (COX-2) expression. A Chr 18 (37-41 cM) QTL modulated both the number of lung tumors induced by 3-methylcholanthrene (MCA) injection with subsequent treatment with BHT as well as BHT-induced ingress of macrophages into airways. Other chromosomal sites that affected either the degree of BHT-elicited macrophage infiltration, Chr 9 (48-61 cM), or COX-2 induction, Chr 10 (59-65 cM), were reported to influence susceptibility to lung tumorigenesis in other strains. The fact that common chromosomal locations regulate both inflammation and carcinogenesis suggests a pathogenic role of inflammatory mediators in tumor development that may be exploited for chemoprevention of lung cancer.

  14. Antioxidant effect of butylated hydroxytoluene on ferric nitrilotriacetate induced renal hyper proliferation and injury in rats.

    PubMed

    Ansar, S

    2013-08-01

    This study was designed to investigate the effect of butylated hydroxy toluene (BHT), a phenolic antioxidant used in foods, cosmetics and pharmaceutical products, on Fe-NTA-induced nephrotoxicity in rats. Fe-NTA (alone) treatment enhances ornithine decarboxylase activity to 5.3-fold, and [(3)H] thymidine incorporation in DNA to 3.5-fold compared with the corresponding saline treated control. The enhanced ornithine decarboxylase activity and DNA synthesis showed a reduction to 2.12-2.15-fold respectively at a higher dose of 2 mg BHT/day/animal, compared with the Fe-NTA treated group. Fe-NTA treatment also enhanced the renal microsomal lipid peroxidation to 2.0-fold and decreased the activities of glutathione and antioxidant enzymes to a range of 2.2-2.5-fold in kidney. These changes were reversed significantly in animals receiving a pretreatment of BHT. Present data suggests that BHT can prevent the toxic effects of Fe-NTA and can serve as a potent chemopreventive agent to suppress oxidant-induced tissue injury and nephrotoxicity in rats.

  15. Diffuse interstitial pulmonary fibrosis: pulmonary fibrosis in mice induced by treatment with butylated hydroxytoluene and oxygen

    SciTech Connect

    Haschek, W.M.; Brody, A.R.; Klein-Szanto, A.J.P.; Witschi, H.

    1981-12-01

    It is proposed that the pulmonary fibrosis induced in mice by treatment with BHT and oxygen is a good experimental model for human pulmonary fibrosis. The mechanism of synergistic and additive effects of various agents on pulmonary injury and the epithelial mesenchymal interactions occurring during the early and late phases of lung repair could be studied. This model could be used for study of the effects of various concentrations of oxygen on diffusely damaged lung and assessment of the efficacy of drugs in preventing or resolving excessive collagen accumulation in lung. In addition, the relationship between pulmonary fibrosis and emphysema could be studied.

  16. Activation of liver X receptor inhibits the development of pulmonary carcinomas induced by 3-methylcholanthrene and butylated hydroxytoluene in BALB/c mice.

    PubMed

    Wang, Qixue; Sun, Lei; Yang, Xiaoxiao; Ma, Xingzhe; Li, Qi; Chen, Yuanli; Liu, Ying; Zhang, Di; Li, Xiaoju; Xiang, Rong; Wei, Yuquan; Han, Jihong; Duan, Yajun

    2016-01-01

    We previously reported that LXR ligand, T0901317, inhibited the growth of inoculated Lewis lung carcinoma in C57BL/6 mice by activating IFN-γ production. However, the effects of T0901317 on carcinogen-induced pulmonary carcinomas remain unknown. In this study, we initially conducted a statistical analysis on the data of human lung cancer samples extracted from the TCGA database, and determined that survival rate/time of lung cancer patients and grade of lung adenocarcinoma were positively and negatively related to lung IFN-γ levels, respectively. We then determined the inhibitory effects of T0901317 on mouse pulmonary carcinomas induced by 3-methylcholanthrene (MCA) and butylated hydroxytoluene (BHT) or urethane. We found that T0901317 reduced morbidity and mortality in MCA/BHT-injected BALB/c mice by inhibiting lung adenocarcinoma. T0901317 also protected C57BL/6 mice, but not IFN-γ deficient (IFN-γ(-/-), C57BL/6 background) mice, against MCA/BHT-induced lung hyperplasia/inflammation. In addition, we determined that T0901317 inhibited urethane-induced lung tumors in BABL/c mice. Furthermore, we determined that T0901317 prevented metastasis of 4T1 breast cancer cells in BALB/c mice. Administration of T0901317 substantially increased serum IFN-γ levels and lung IFN-γ expression in BABL/c and C57BL/6 mice. Taken together, our study demonstrates that LXR inhibits MCA/BHT-induced pulmonary carcinomas in BABL/c mice and the inhibition is associated with induction of IFN-γ production. PMID:27250582

  17. Activation of liver X receptor inhibits the development of pulmonary carcinomas induced by 3-methylcholanthrene and butylated hydroxytoluene in BALB/c mice

    PubMed Central

    Wang, Qixue; Sun, Lei; Yang, Xiaoxiao; Ma, Xingzhe; Li, Qi; Chen, Yuanli; Liu, Ying; Zhang, Di; Li, Xiaoju; Xiang, Rong; Wei, Yuquan; Han, Jihong; Duan, Yajun

    2016-01-01

    We previously reported that LXR ligand, T0901317, inhibited the growth of inoculated Lewis lung carcinoma in C57BL/6 mice by activating IFN-γ production. However, the effects of T0901317 on carcinogen-induced pulmonary carcinomas remain unknown. In this study, we initially conducted a statistical analysis on the data of human lung cancer samples extracted from the TCGA database, and determined that survival rate/time of lung cancer patients and grade of lung adenocarcinoma were positively and negatively related to lung IFN-γ levels, respectively. We then determined the inhibitory effects of T0901317 on mouse pulmonary carcinomas induced by 3-methylcholanthrene (MCA) and butylated hydroxytoluene (BHT) or urethane. We found that T0901317 reduced morbidity and mortality in MCA/BHT-injected BALB/c mice by inhibiting lung adenocarcinoma. T0901317 also protected C57BL/6 mice, but not IFN-γ deficient (IFN-γ−/−, C57BL/6 background) mice, against MCA/BHT-induced lung hyperplasia/inflammation. In addition, we determined that T0901317 inhibited urethane-induced lung tumors in BABL/c mice. Furthermore, we determined that T0901317 prevented metastasis of 4T1 breast cancer cells in BALB/c mice. Administration of T0901317 substantially increased serum IFN-γ levels and lung IFN-γ expression in BABL/c and C57BL/6 mice. Taken together, our study demonstrates that LXR inhibits MCA/BHT-induced pulmonary carcinomas in BABL/c mice and the inhibition is associated with induction of IFN-γ production. PMID:27250582

  18. Carbonyl reductase inactivation may contribute to mouse lung tumor promotion by electrophilic metabolites of butylated hydroxytoluene: protein alkylation in vivo and in vitro.

    PubMed

    Shearn, Colin T; Fritz, Kristofer S; Meier, Brent W; Kirichenko, Oleg V; Thompson, John A

    2008-08-01

    Promotion of lung tumors in mice by the food additive butylated hydroxytoluene (BHT) is mediated by electrophilic metabolites produced in the target organ. Identifying the proteins alkylated by these quinone methides (QMs) is a necessary step in understanding the underlying mechanisms. Covalent adducts of the antioxidant enzymes peroxiredoxin 6 and Cu,Zn superoxide dismutase were detected previously in lung cytosols from BALB/c mice injected with BHT, and complimentary in vitro studies demonstrated that QM alkylation causes inactivation and enhances oxidative stress. In the present work, adducts of another protective enzyme, carbonyl reductase (CBR), were detected by Western blotting and mass spectrometry in mitochondria from lungs of mice one day after a single injection of BHT and throughout a 28-day period of weekly injections required to achieve tumor promotion. BHT treatment was accompanied by the accumulation of protein carbonyls in lung cytosol from sustained oxidative stress. Studies in vitro demonstrated that CBR activity in lung homogenates was susceptible to concentration- and time-dependent inhibition by QMs. Recombinant CBR underwent irreversible inhibition during QM exposure, and mass spectrometry was utilized to identify alkylation sites at Cys 51, Lys 17, Lys 189, Lys 201, His 28, and His 204. Except for Lys 17, all of these adducts were eliminated as a cause of enzyme inhibition either by chemical modification (cysteine) or site-directed mutagenesis (lysines and histidines). The data demonstrated that Lys 17 is the critical alkylation target, consistent with the role of this basic residue in NADPH binding. These data support the possibility that CBR inhibition occurs in BHT-treated mice, thereby compromising one pathway for inactivating lipid peroxidation products, particularly 4-oxo-2-nonenal. These data, in concert with previous evidence for the inactivation of antioxidant enzymes, provide a molecular basis to explain lung inflammation leading to

  19. Activation of liver X receptor inhibits the development of pulmonary carcinomas induced by 3-methylcholanthrene and butylated hydroxytoluene in BALB/c mice.

    PubMed

    Wang, Qixue; Sun, Lei; Yang, Xiaoxiao; Ma, Xingzhe; Li, Qi; Chen, Yuanli; Liu, Ying; Zhang, Di; Li, Xiaoju; Xiang, Rong; Wei, Yuquan; Han, Jihong; Duan, Yajun

    2016-06-02

    We previously reported that LXR ligand, T0901317, inhibited the growth of inoculated Lewis lung carcinoma in C57BL/6 mice by activating IFN-γ production. However, the effects of T0901317 on carcinogen-induced pulmonary carcinomas remain unknown. In this study, we initially conducted a statistical analysis on the data of human lung cancer samples extracted from the TCGA database, and determined that survival rate/time of lung cancer patients and grade of lung adenocarcinoma were positively and negatively related to lung IFN-γ levels, respectively. We then determined the inhibitory effects of T0901317 on mouse pulmonary carcinomas induced by 3-methylcholanthrene (MCA) and butylated hydroxytoluene (BHT) or urethane. We found that T0901317 reduced morbidity and mortality in MCA/BHT-injected BALB/c mice by inhibiting lung adenocarcinoma. T0901317 also protected C57BL/6 mice, but not IFN-γ deficient (IFN-γ(-/-), C57BL/6 background) mice, against MCA/BHT-induced lung hyperplasia/inflammation. In addition, we determined that T0901317 inhibited urethane-induced lung tumors in BABL/c mice. Furthermore, we determined that T0901317 prevented metastasis of 4T1 breast cancer cells in BALB/c mice. Administration of T0901317 substantially increased serum IFN-γ levels and lung IFN-γ expression in BABL/c and C57BL/6 mice. Taken together, our study demonstrates that LXR inhibits MCA/BHT-induced pulmonary carcinomas in BABL/c mice and the inhibition is associated with induction of IFN-γ production.

  20. Determination of butylated hydroxytoluene in food samples by high-performance liquid chromatography with ultraviolet detection and gas chromatography/mass spectrometry.

    PubMed

    Sanches-Silva, Ana; Cruz, José M; Sendón-García, Raquel; Paseiro-Losada, Perfecto

    2007-01-01

    A reversed-phase high-performance liquid chromatography (RP-HPLC) method was developed and compared with a gas chromatography/mass spectrometry (GC/MS) method for determining butylated hydroxytoluene (BHT) in foodstuffs as a result of migration from plastic packaging. Similar extraction procedures were used in both methods. BHT was quantitated using an external standard in the HPLC method and an internal standard in the GC/MS method. Both methods presented good linearity (r(2) > or = 0.9917) and low detection limits. Recoveries obtained with the HPLC method (chicken meat, 95.8%, and Gouda cheese, 83.9%) were better than with the GC/MS method (chicken meat, 85.6%, and Gouda cheese, 71.3%).

  1. Butylated hydroxytoluene can protect polyunsaturated fatty acids in dried blood spots from degradation for up to 8 weeks at room temperature

    PubMed Central

    2013-01-01

    Background Dried blood spots (DBS) from fingertip prick blood can enable high throughput fatty acid profiling but may be prone to lipid peroxidation during storage. The use of butylated hydroxytoluene (BHT) on chromatography paper can prevent polyunsaturated fatty acid (PUFA) loss but examinations on the length of storage times possible are not comprehensive. Method In the first study, venous whole blood was saturated on paper strips pre-soaked with 0, 2.5 or 5.0 mg/mL BHT and exposed to air for up to 28 days. In a second study, the effect of sealing DBS on 5.0 mg/mL BHT-soaked chromatography strips in capped test tubes or vacuum sealed polypropylene bags with and without nitrogen purging was examined over eight weeks. The fatty acid composition of the DBS were determined by gas chromatography and the effect of sample storage on omega-3 biomarkers were examined. Results PUFA and omega-3 biomarkers in DBS stored without BHT were dramatically reduced by day 3. In general, BHT delayed decreases in eicosapentaenoic + docosahexaenoic acid from baseline (3.2 ± 0.2 wt%) to 28 days (2.6 ± 0.03 wt%) of storage. In the % n-3 highly unsaturated fatty acids (HUFA) in total HUFA biomarker, BHT was more effective at preventing changes, particularly with 5.0 mg/mL BHT where no differences were detected up to 28 days. Sealed storage with BHT tended to increase the stability of the PUFA in DBS and nitrogen purging did not appear to provide additional benefits. The % n-3 HUFA in total HUFA biomarker also appeared to be more stable in the sealed storage study. Conclusions The storage of DBS in sealed containers with BHT may prevent PUFA degradation for up to 8 weeks. The % n-3 HUFA in total HUFA biomarker appears to provide a more consistent assessment of omega-3 status throughout storage as compared with other omega-3 blood biomarkers. PMID:23425563

  2. Sequestering ability of butylated hydroxytoluene, propyl gallate, resveratrol, and vitamins C and E against ABTS, DPPH, and hydroxyl free radicals in chemical and biological systems.

    PubMed

    Soares, Daniele G; Andreazza, Ana C; Salvador, Mirian

    2003-02-12

    The antioxidant capacity of butylated hydroxytoluene (BHT; 2,6-di-tert-butyl-p-cresol), propyl gallate (3,4,5-trihydroxybenzoic acid n-propyl ester), resveratrol (trans-3,4',5-trihydroxystilbene), and vitamins C (l-ascorbic acid) and E [(+)-alpha-tocopherol] was studied in chemical and biological systems. The chemical assays evaluated the capacity of these antioxidants to sequester 2,2'-azinobis(3-ethylbenzthiazoline-6-sulfonic acid) (ABTS.) and 1,1 diphenyl-2-picrylhydrazyl (DPPH.). A new colorimetric method to determine hydroxyl radical scavenging is also described. The biological tests use the eucaryotic cells of Saccharomyces cerevisiae treated with the antioxidants in the presence of the stressing agents apomorphine, hydrogen peroxide, and paraquat dichloride (methylviologen; 1,1'-dimethyl-4,4'-bipyridinium dichloride). The results in chemical systems showed that all of the antioxidants were able to significantly inhibit the oxidation of beta-carotene by hydroxyl free radicals. The assays in yeast showed that the antioxidant activity of the tested compounds depended on the stressing agent used and the mechanism of action of the antioxidant.

  3. Strain-dependent lung tumor formation in mice transplacentally exposed to 3-methylcholanthrene and post-natally exposed to butylated hydroxytoluene.

    PubMed

    Gressani, K M; Leone-Kabler, S; O'Sullivan, M G; Case, L D; Malkinson, A M; Miller, M S

    1999-11-01

    The carcinogenic effects of in utero exposure to 3-methylcholanthrene (MC) have been demonstrated in the tumor-resistant C57BL/6 (B6) and DBA (D2) strains of mice. In this study, we determined the effects of in utero exposure to MC in BALB/c mice, a strain which demonstrates greater susceptibility to lung tumor induction, and compared our findings with those previously found in [D2xB6D2F(1)]F(2) mice. In addition, we assessed the molecular pathogenesis of the chemically induced tumors and examined the effects of the putative lung tumor promoter butylated hydroxytoluene (BHT) in BALB/c mice. BALB/c mice were treated on day 17 of gestation with 5, 15 or 45 mg/kg MC and 6 weeks after birth with BHT for 6 consecutive weeks. Mice were killed at 6 months of age. Ki-ras, p16Ink4a and p19ARF gene loci were amplified from paraffin-embedded lung tumor tissue and screened for the presence of point mutations via allele-specific oligonucleotide hybridization and single strand conformation polymorphism (SSCP) analyses. Ki-ras point mutations were found in 56% (20/36) of BALB/c lung tumors, with 33% (2/6) of the hyperplasias, 58% (10/19) of the adenomas and 73% (8/11) of the carcinomas exhibiting point mutations at this gene locus. Similar incidences of Ki-ras mutations were previously found following transplacental exposure of [D2xB6D2F(1)]F(2) mice to MC and treatment of adult A/J mice with urethane. Interestingly, a strain-dependent difference was observed in the mutational spectrum. Sixty-two and 38% of the lung lesions in BALB/c mice exhibited G-->C and G-->T transversions, respectively, in contrast to the 13 and 84% incidences previously observed in [D2xB6D2F(1)]F(2) mice. SSCP analysis of the tumor suppressor gene p16Ink4a showed a 6% incidence of point mutations, consistent with that found in [D2xB6D2F(1)]F(2) mice. No mutations were found in exon 1beta of the p19ARF gene of either strain. BHT, a lung tumor promoter in adult mice, had no statistically significant effects

  4. Effects of butylated hydroxytoluene pretreatment on the metabolism and genotoxicity of aflatoxin B1 in primary cultures of adult rat hepatocytes: selective reduction of nucleic acid binding.

    PubMed

    Salocks, C B; Hsieh, D P; Byard, J L

    1984-12-01

    To elucidate biochemical mechanisms underlying the anticarcinogenic activity of butylated hydroxytoluene (BHT), studies were undertaken to characterize the influence of BHT pretreatment on the metabolism and genotoxicity of aflatoxin B1 (AFB1) in primary cultures of rat hepatocytes. During a 10-day pretreatment period, adult male rats were fed either a control diet or a diet supplemented with 0.5% BHT. Hepatocytes were subsequently isolated from each animal and cultured in chemically defined medium. Cultures prepared from rats which had been fed BHT metabolized AFB1 more rapidly than did controls. BHT pretreatment also enhanced oxidation of AFB1 to aflatoxin M1 (AFM1), and accelerated the rate of AFM1 conjugation. Covalent binding to DNA and RNA in BHT-pretreated cultures was reduced by 91 and 82%, respectively, while protein binding decreased by only 29%. AFB1 did not stimulate detectable DNA repair synthesis in BHT-pretreated cultures, although stimulation of DNA repair was clearly evident in control cultures. In a separate experiment, consistently higher baseline concentrations of reduced glutathione were observed in BHT-pretreated cells, indicating that BHT pretreatment may enhance formation of detoxified glutathione conjugates of AFB1. These findings suggest that the anticarcinogenic activity of BHT is due in part to preferential enhancement of hepatic detoxification mechanisms, with the result that intracellular concentrations of reactive metabolites are reduced and fewer covalently bound adducts are formed.

  5. Change in fluidity of brain endoplasmic reticulum membranes by oxygen free radicals: a protective effect of stobadine, alpha-tocopherol acetate, and butylated hydroxytoluene.

    PubMed

    Kaplán, P; Racay, P; Lehotský, J; Mézesová, V

    1995-07-01

    Effect of various oxygen free radical generating systems and an oxidant H2O2 on brain endoplasmic reticulum (ER) membrane fluidity was examined using fluorescent membrane probe 1,6-diphenyl-1,3,5-hexatriene, DPH. The relative potency of free radical generating systems to decrease membrane fluidity increased in this order: FeCl3-EDTA, FeSO4-EDTA, FeSO4-EDTA/hydrogen peroxide. Potency to decrease membrane fluidity correlated well with these systems' potencies to induce lipid peroxidation, as detected by conjugated diene formation. Treatment of ER membranes with H2O2 had no effect on fluidity or conjugated diene formation. Using the two most potent free radical generating systems, FeSO4-EDTA and FeSO4-EDTA/hydrogen peroxide, a protective effect of the novel antihypoxic and antiarrhytmic drug stobadine was tested. Stobadine and two well-known antioxidants, alpha-tocopherol acetate and butylated hydroxytoluene, demonstrated the ability to prevent free radical induced alterations in ER membrane fluidity. These results provide new evidence of stobadine's protective effect on membranes attacked by oxygen free radicals.

  6. Rational Design and Synthesis of New, High Efficiency, Multipotent Schiff Base-1,2,4-triazole Antioxidants Bearing Butylated Hydroxytoluene Moieties.

    PubMed

    Yehye, Wageeh A; Abdul Rahman, Noorsaadah; Saad, Omar; Ariffin, Azhar; Abd Hamid, Sharifah Bee; Alhadi, Abeer A; Kadir, Farkaad A; Yaeghoobi, Marzieh; Matlob, Abdulsalam A

    2016-06-28

    A new series of multipotent antioxidants (MPAOs), namely Schiff base-1,2,4-triazoles attached to the oxygen-derived free radical scavenging moiety butylated hydroxytoluene (BHT) were designed and subsequently synthesized. The structure-activity relationship (SAR) of the designed antioxidants was established alongside the prediction of activity spectra for substances (PASS). The antioxidant activities of the synthesized compounds 4-10 were tested by the DPPH bioassay. The synthesized compounds 4-10 inhibited stable DPPH free radicals at a level that is 10(-4) M more than the well-known standard antioxidant BHT. Compounds 8-10 with para-substituents were less active than compounds 4 and 5 with trimethoxy substituents compared to those with a second BHT moiety (compounds 6 and 7). With an IC50 of 46.13 ± 0.31 µM, compound 6 exhibited the most promising in vitro inhibition at 89%. Therefore, novel MPAOs containing active triazole rings, thioethers, Schiff bases, and BHT moieties are suggested as potential antioxidants for inhibiting oxidative stress processes and scavenging free radicals, hence, this combination of functions is anticipated to play a vital role in repairing cellular damage, preventing various human diseases and in medical therapeutic applications.

  7. Rational Design and Synthesis of New, High Efficiency, Multipotent Schiff Base-1,2,4-triazole Antioxidants Bearing Butylated Hydroxytoluene Moieties.

    PubMed

    Yehye, Wageeh A; Abdul Rahman, Noorsaadah; Saad, Omar; Ariffin, Azhar; Abd Hamid, Sharifah Bee; Alhadi, Abeer A; Kadir, Farkaad A; Yaeghoobi, Marzieh; Matlob, Abdulsalam A

    2016-01-01

    A new series of multipotent antioxidants (MPAOs), namely Schiff base-1,2,4-triazoles attached to the oxygen-derived free radical scavenging moiety butylated hydroxytoluene (BHT) were designed and subsequently synthesized. The structure-activity relationship (SAR) of the designed antioxidants was established alongside the prediction of activity spectra for substances (PASS). The antioxidant activities of the synthesized compounds 4-10 were tested by the DPPH bioassay. The synthesized compounds 4-10 inhibited stable DPPH free radicals at a level that is 10(-4) M more than the well-known standard antioxidant BHT. Compounds 8-10 with para-substituents were less active than compounds 4 and 5 with trimethoxy substituents compared to those with a second BHT moiety (compounds 6 and 7). With an IC50 of 46.13 ± 0.31 µM, compound 6 exhibited the most promising in vitro inhibition at 89%. Therefore, novel MPAOs containing active triazole rings, thioethers, Schiff bases, and BHT moieties are suggested as potential antioxidants for inhibiting oxidative stress processes and scavenging free radicals, hence, this combination of functions is anticipated to play a vital role in repairing cellular damage, preventing various human diseases and in medical therapeutic applications. PMID:27367658

  8. Non-Specific Inhibition of Ischemia- and Acidosis-Induced Intracellular Calcium Elevations and Membrane Currents by α-Phenyl-N-tert-butylnitrone, Butylated Hydroxytoluene and Trolox

    PubMed Central

    Katnik, Christopher; Cuevas, Javier

    2014-01-01

    Ischemia, and subsequent acidosis, induces neuronal death following brain injury. Oxidative stress is believed to be a key component of this neuronal degeneration. Acute chemical ischemia (azide in the absence of external glucose) and acidosis (external media buffered to pH 6.0) produce increases in intracellular calcium concentration ([Ca2+]i) and inward membrane currents in cultured rat cortical neurons. Two α-tocopherol analogues, trolox and butylated hydroxytoluene (BHT), and the spin trapping molecule α-Phenyl-N-tert-butylnitrone (PBN) were used to determine the role of free radicals in these responses. PBN and BHT inhibited the initial transient increases in [Ca2+]i, produced by ischemia, acidosis and acidic ischemia and increased steady state levels in response to acidosis and the acidic ischemia. BHT and PBN also potentiated the rate at which [Ca2+]i increased after the initial transients during acidic ischemia. Trolox inhibited peak and sustained increases in [Ca2+]i during ischemia. BHT inhibited ischemia induced initial inward currents and trolox inhibited initial inward currents activated by acidosis and acidic ischemia. Given the inconsistent results obtained using these antioxidants, it is unlikely their effects were due to elimination of free radicals. Instead, it appears these compounds have non-specific effects on the ion channels and exchangers responsible for these responses. PMID:24583849

  9. Effect of a low-density polyethylene film containing butylated hydroxytoluene on lipid oxidation and protein quality of Sierra fish (Scomberomorus sierra) muscle during frozen storage.

    PubMed

    Torres-Arreola, Wilfrido; Soto-Valdez, Herlinda; Peralta, Elizabeth; Cardenas-López, José Luis; Ezquerra-Brauer, Josafat Marina

    2007-07-25

    Fresh sierra fish (Scomberomorus sierra) fillets were packed in low-density polyethylene films with butylated hydroxytoluene (BHT-LDPE) added. Fillets packed in LDPE with no BHT were used as controls (LDPE). The packed fillets were stored at -25 degrees C for 120 days in which the film released 66.5% of the antioxidant. The influence of the antioxidant on lipid and protein quality, lipid oxidation, muscle structure changes, and shear-force resistance was recorded. As compared to LDPE films, fillets packed in BHT-LDPE films showed lower lipid oxidation, thiobarbituric acid values (4.20 +/- 0.52 vs 11.95 +/- 1.06 mg malonaldehyde/kg), peroxide values (7.20 +/- 1.38 vs 15.15 +/- 1.48 meq/kg), and free fatty acids (7.98 +/- 0.43 vs 11.83 +/- 1.26% of oleic acid). Fillets packed in BHT-LDPE films showed less tissue damage and lost less firmness than fillets packed in LDPE. A significant relationship between lipid oxidation and texture was detected (R2 adjusted, 0.70-0.73). BHT-LDPE films may be used not only to prevent lipid oxidation but also to minimize protein damage to prolong the shelf life of sierra fish.

  10. Non-specific inhibition of ischemia- and acidosis-induced intracellular calcium elevations and membrane currents by α-phenyl-N-tert-butylnitrone, butylated hydroxytoluene and trolox.

    PubMed

    Katnik, Christopher; Cuevas, Javier

    2014-02-27

    Ischemia, and subsequent acidosis, induces neuronal death following brain injury. Oxidative stress is believed to be a key component of this neuronal degeneration. Acute chemical ischemia (azide in the absence of external glucose) and acidosis (external media buffered to pH 6.0) produce increases in intracellular calcium concentration ([Ca2+]i) and inward membrane currents in cultured rat cortical neurons. Two α-tocopherol analogues, trolox and butylated hydroxytoluene (BHT), and the spin trapping molecule α-Phenyl-N-tert-butylnitrone (PBN) were used to determine the role of free radicals in these responses. PBN and BHT inhibited the initial transient increases in [Ca2+]i, produced by ischemia, acidosis and acidic ischemia and increased steady state levels in response to acidosis and the acidic ischemia. BHT and PBN also potentiated the rate at which [Ca2+]i increased after the initial transients during acidic ischemia. Trolox inhibited peak and sustained increases in [Ca2+]i during ischemia. BHT inhibited ischemia induced initial inward currents and trolox inhibited initial inward currents activated by acidosis and acidic ischemia. Given the inconsistent results obtained using these antioxidants, it is unlikely their effects were due to elimination of free radicals. Instead, it appears these compounds have non-specific effects on the ion channels and exchangers responsible for these responses.

  11. Selective inhibition and induction of CYP activity discriminates between the isoforms responsible for the activation of butylated hydroxytoluene and naphthalene in mouse lung.

    PubMed

    Verschoyle, R D; Martin, J; Dinsdale, D

    1997-08-01

    1. Selective induction and inhibition experiments have been used to identify the cytochrome P450 (CYP) isoforms responsible for butylated hydroxytoluene (BHT) bioactivation in mouse lung. 2. Pre-treatment of BALB/c mice with O,O,O-trimethylphosphorothioate (OOOMeP(S)), which prevented all the signs of toxicity observed following BHT treatment, inhibited the pulmonary activity of pentoxyresorufin O-dealkylase (PROD) and coumarin hydroxylase but not 4-nitrophenol hydroxylase. 3. Pulmonary coumarin hydroxylase activity was greater in DBA than in BALB/c mice but the severity of BHT-induced lung injury was similar. 4. Pre-treatment with pyrazole, which exacerbated BHT-induced lung injury, did not affect pulmonary coumarin hydroxylase or 4-nitrophenol hydroxylase activity but increased that of PROD. 5. Pre-treatment with OOOMeP(S) prevented the lethargy and weight-loss associated with naphthalene poisoning but not the pulmonary injury. Pre-treatment with pyrazole did not exacerbate naphthalene-induced injury. 6. Members of both CYP2F and 2B sub-families have been shown to exhibit PROD activity and 2F2 activates naphthalene in mouse lung. The current studies, however, indicate that 2F2 is unlikely to be a significant component of PROD activity in mouse lung. 2F2, like coumarin hydroxylase (2A5) and 4-nitrophenol hydroxylase (2E1), is not responsible for the pulmonary activation of BHT, which is largely attributable to an isoform of 2B, probably 2B10.

  12. Butylated hydroxytoluene does not protect Chinese hamster ovary cells from chromosomal damage induced by high-dose rate 192Ir irradiation.

    PubMed

    Grillo, C A; Dulout, F N

    2006-11-01

    Previous reports showed the protective effect of the synthetic antioxidant butylated hydroxytoluene (BHT) against the chromosomal damage induced by bleomycin (BLM), cadmium chloride and potassium dichromate. To test the hypothesis that this effect was exerted by inhibition and/or scavenging of reactive oxygen species (ROS), the effect of BHT on the chromosomal damage induced by a high dose-rate gamma rays (HDR (192)Ir). Experiments were carried out by irradiating G(1) CHO cells with nominal doses of 1, 2 or 3 Gy. BHT (doses of 1.0, 2.5 or 5.0 microg/ml) was added to the culture immediately before or immediately after irradiation. Cells were then incubated in the presence of BHT for 13 h until harvesting and fixation. Results obtained showed that BHT did not decrease the chromosomal damage induced by radiation in any consistent fashion. On the contrary, in cells post-treated with 5.0 microg/ml of BHT the yield of chromosomal aberrations increased in several experimental points. These results with ionizing radiation suggest that the previous observed protective effects of BHT on the chromosomal damage induced by chemical genotoxicants may not be mediated solely through the scavenging or inactivating reactive oxidative species. The decrease of the yield of chromosomal damage induced by BLM could be due to the union of BHT with a metallic ion, in this case Fe (II), required for the activation of BLM. In the same way, the protective effect of BHT on the chromosomal damage induced by cadmium chloride and potassium dichromate could be due to the decrease of the effective dose of both salts in the cell through the chelation of the cations by BHT.

  13. Butylated hydroxytoluene can reduce oxidative stress and improve quality of frozen-thawed bull semen processed in lecithin and egg yolk based extenders.

    PubMed

    Khumran, A M; Yimer, N; Rosnina, Y; Ariff, M O; Wahid, H; Kaka, Asmatullah; Ebrahimi, M; Sarsaifi, K

    2015-12-01

    The aims of this study were to evaluate the effects of anti-oxidant butylated hydroxytoluene (BHT), when added at different concentrations into lecithin-based Bioxcell(®) (BX) and two egg-yolk-based; Tris (TY) and citrate (CE) semen extenders, on post-thaw bull sperm quality and oxidative stress. A total of 30 ejaculates from three bulls were collected using an electro ejaculator. Ejaculates were extended with one of the BX, TY and CE extenders, which contained different concentrations (0.0 - control, 0.5, 1.0, 1.5, 2.0 and 3.0mM/ml) of BHT. The extended semen samples were chilled to 4 °C, and then frozen slowly to -196 °C in 0.25 ml straws before being stored in liquid nitrogen for 2 weeks. Results showed that supplementation of BHT improved (P<0.05) general motility, progressive motility, morphology, acrosome integrity, DNA integrity and malondialdehyde of sperm at 0.5mM/ml for BX and at 1-1.5mM/ml of BHT for TY and CE when compared with the control. However, greater concentrations of 2.0 and 3.0mM/ml of BHT had a detrimental (P<0.05) effect compared with the control with all extenders evaluated. In conclusion, BHT supplementation at lesser concentrations (0.5-1.5mM/ml) could improve frozen-thawed bull sperm quality by reducing oxidative stress produced during the freezing-thawing procedures in either lecithin or egg-yolk based extenders.

  14. Nrf3-deficient mice are not protected against acute lung and adipose tissue damages induced by butylated hydroxytoluene.

    PubMed

    Chevillard, Grégory; Nouhi, Zaynab; Anna, Derjuga; Paquet, Marilène; Blank, Volker

    2010-03-01

    We found that both wild type and Nrf3 (NF-E2-related factor 3) deficient mice are sensitive to BHT single administration exhibiting respiratory distress and considerably lose body weight following treatment. At time of sacrifice, the BHT-treated Nrf3-/- mice had lost significantly more body weight than their WT counterparts. In the lung, transcript levels of the transcription factors Nrf1, Nrf2 and Nrf3 were differentially regulated by BHT treatment. In addition, genes implicated in adipogenesis were repressed following BHT exposure in the white adipose tissue. Together, our data provide the first evidence that BHT exposure not only affects lung function but also leads to impaired adipogenesis in adipocytes.

  15. Studies using structural analogs and inbred strain differences to support a role for quinone methide metabolites of butylated hydroxytoluene (BHT) in mouse lung tumor promotion.

    PubMed

    Thompson, J A; Carlson, T J; Sun, Y; Dwyer-Nield, L D; Malkinson, A M

    2001-03-01

    Chronic treatment of BALB and GRS mice with BHT (2,6-di-tert-butyl-4-methylphenol) following a single urethane injection increases lung tumor multiplicity, but this does not occur in CXB4 mice. Previous data suggest that promotion requires the conversion of BHT to a tert-butyl-hydroxylated metabolite (BHTOH) in lung and the subsequent oxidation of this species to an electrophilic quinone methide. To obtain additional evidence for the importance of quinone methide formation, structural analogs that form less reactive quinone methides were tested and found to lack promoting activity in BHT-responsive mice. The possibility that promotion-unresponsive strains are unable to form BHTOH was tested by substituting this compound for BHT in the promotion protocol using CXB4 mice. No promotion occurred, and in-vitro work demonstrated that CXB4 mice are, in fact, capable of producing BHTOH and its quinone methide, albeit in smaller quantities. Incubations with BALB lung microsomes and radiolabeled substrates confirmed that more covalent binding to protein occurs with BHTOH than with BHT and, in addition, BHTOH quinone methide is considerably more toxic to mouse lung epithelial cells than BHT quinone methide. These data are consistent with the hypothesis that a two-step oxidation process, i.e. hydroxylation and quinone methide formation, is required for the promotion of mouse lung tumors by BHT.

  16. Butylate

    Integrated Risk Information System (IRIS)

    Butylate ; CASRN 2008 - 41 - 5 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogenic Effects

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

    Technology Transfer Automated Retrieval System (TEKTRAN)

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

  18. The lung tumor promoter, butylated hydroxytoluene (BHT), causes chronic inflammation in promotion-sensitive BALB/cByJ mice but not in promotion-resistant CXB4 mice.

    PubMed

    Bauer, A K; Dwyer-Nield, L D; Hankin, J A; Murphy, R C; Malkinson, A M

    2001-12-01

    An inflammatory response accompanies the reversible pneumotoxicity caused by butylated hydroxytoluene (BHT) administration to mice. Lung tumor formation is promoted by BHT administration following an initiating agent in BALB/cByJ mice, but not in CXB4 mice. To assess the contribution of inflammation to this differential susceptibility, we quantitatively characterized inflammation after one 150 mg/kg body weight, followed by three weekly 200 mg/kg ip injections of BHT into male mice of both strains. This examination included inflammatory cell infiltrate and protein contents in bronchoalveolar lavage (BAL) fluid, cyclooxygenase (COX)-1 and COX-2 expression in lung extracts, and PGE(2) and PGI(2) production by isolated bronchiolar Clara cells. BAL macrophage and lymphocyte numbers increased in BALB mice (P<0.0007 and 0.02, respectively), as did BAL protein content (P<0.05), COX-1 and COX-2 expression (P<0.05 for each), and PGI(2) production (P<0.05); conversely, these indices were not perturbed by BHT in CXB4 mice. BALB mice fed aspirin (400 mg/kg of chow) for two weeks prior to BHT treatment had reduced inflammatory cell infiltration. Our results support a hypothesis that resistance to BHT-induced inflammation in CXB4 mice accounts, at least in part, for the lack of effect of BHT on lung tumor multiplicity in this strain.

  19. Effect of. cap alpha. -tocopherol, butylated-hydroxytoluene and hydroxy-anisole on the activation and binding of aflatoxin B/sub 1/ to macromolecules

    SciTech Connect

    Ch'ih, J.J.; Biedrzycka, D.; Devlin, T.M.

    1987-05-01

    The anti-oxidants, ..cap alpha..-tocopherol(TPA), butylated-hydroxy-toluene(BHT) and hydroxyanisole(BHA) inhibit the carcinogenic and toxic effects of a variety of chemical compounds, their effect on aflatoxin B/sub 1/ (AFB/sub 1/) activation and binding was examined utilizing rat liver microsomes and cells. With a NADPH generating system, oxygen, microsomes, (/sup 3/H)-AFB/sub 1/, 2.2 pmoles/h/mg protein was activated and bound to macromolecules. In hepatocytes, 3.4 and 1.4 pmoles of AFB/sub 1/ per 10/sup 6/ cells were taken up and bound to macromolecules, whereas the nucleic acid fraction contained 0.19 pmoles of bound AFB/sub 1/. Moderate decreases of AFB/sub 1/ activation and binding were observed when TPA was present in both cell-free and hepatocytes systems. Only in hepatocytes, BHT inhibited the AFB/sub 1/ uptake and binding to nucleic acids. BHA, however, inhibited microsomal activation of AFB/sub 1/ by 73%; maximum inhibition was reached at 1 mM. AFB/sub 1/ uptake, and binding to nucleic acids were inhibited by 65% and 79% by BHA. GSH-transferase activity of cells treated with these agents was not altered. The effect of BHA at various concentrations on AFB activation was compared with cytochrome P-450 inhibitors; the ED/sub 50/ of SKF 525A, BHA and metyrapone was 9 uM, 80 uM and 380 uM respectively. The data suggest that TPA, BHA and BHT exert their effect by different mechanisms.

  20. Hepatic retention and toxicological responses during feeding and depuration periods in Atlantic salmon ( Salmo salar ) fed graded levels of the synthetic antioxidant, butylated hydroxytoluene.

    PubMed

    Holaas, Eivind; Bohne, Victoria B; Hamre, Kristin; Arukwe, Augustine

    2008-12-10

    The human safety aspects of seafood production require the expansion of vital knowledge of both nutrients and possible contaminants along the entire production chain. Thus, production of safer seafood can be achieved by using feed materials that are low in contaminants, while maintaining balanced nutrition, in order to secure optimal fish and consumer health. Our understanding of primary responses of fish health and production related diseases, as well as biological processes that influence carry-over and lowering of contaminants in farmed fish, will contribute to a sustainable production of safer seafood products. Therefore, we have studied the liver deposition and toxicological effects in salmon fed graded levels of BHT during a 12-week feeding followed by a 2-week depuration period using chemical, molecular, and catalytic assays. In general, our data showed that BHT was significantly retained in the liver and selectively modulated toxicological responses in the xenobiotic biotransformation pathways during the feeding period. Specifically, BHT produced consistent dose- and time-specific gene expression patterns for AhR2alpha, AhR2beta, CYP1A1, CYP3A, UGT1, and GSTpi. The effect of BHT on the gene expression of biotransformation enzyme did not parallel enzyme activity levels, suggesting a possible inhibition by parent BHT or its metabolites. As a safety precaution, the production of farmed Atlantic salmon in Norway requires a mandatory 2-week depuration period prior to slaughtering and market delivery to ensure the elimination of veterinary medicaments, additives, and other undesirable components. Comparison of feeding and depuration periods showed that BHT was highly retained in fish liver, as only 8-13% of fed BHT was eliminated during the 2-week depuration period. This is just a part of the total concentration in the whole fish, since BHT may have been distributed and accumulated in other organs. Since BHT or its metabolites putatively inhibited

  1. 21 CFR 182.3173 - Butylated hydroxytoluene.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... in food when the total content of antioxidants is not over 0.02 percent of fat or oil content, including essential (volatile) oil content of food, provided the substance is used in accordance with...

  2. Structure and generation mechanism of a novel degradation product formed by oxidatively induced coupling of miconazole nitrate with butylated hydroxytoluene in a topical ointment studied by HPLC-ESI-MS and organic synthesis.

    PubMed

    Zhang, Fa; Nunes, Mathews

    2004-02-01

    In a petrolatum based topical ointment formulation containing miconazole nitrate (1) as the active ingredient and 2,6-di-t-butyl-4-methylphenol (BHT) as a vehicle antioxidant, an oxidatively induced coupling reaction between miconazole nitrate and BHT occurred to form a novel adduct 1-(3,5-di-tert-butyl-4-hydroxy-benzyl)-3-[2-(2,4-dichloro-benzyloxy)-2-(2,4-dichloro-phenyl)-ethyl]-3H-imidazol-1-ium nitrate (2). The structure of 2 was established using high-performance liquid chromatography coupled with electrospray ionization mass spectrometry and was confirmed by comparing with a synthesized reference compound. The reaction proceeded through a quinone methide intermediate from BHT. Two synthetic methods were established for preparing 2.

  3. Addition of n-butyl cyanoacrylate to classic transarterial chemoembolization may improve the radiological response in patients with hepatocellular carcinoma

    PubMed Central

    Monsignore, Lucas Moretti; Elias-Junior, Jorge; Muglia, Valdair Francisco; Teixeira, Andreza Correa; Mente, Enio David; de Lourdes Candolo Martinelli, Ana; Abud, Daniel Giansante

    2015-01-01

    OBJECTIVE: Transarterial chemoembolization is the treatment of choice for intermediate-stage hepatocellular carcinoma. However, there are no clear data supporting transarterial chemoembolization vs. transarterial embolization or regarding the best chemotherapeutic agent, which may suggest a preponderant role of ischemia over chemotherapeutic action. This study sought to evaluate the radiological response and outcome of transarterial chemoembolization modified by n-butyl cyanoacrylate addition compared to conventional transarterial chemoembolization in hepatocellular carcinoma patients. MATERIALS AND METHODS: A retrospective review identified forty-seven patients who underwent modified chemoembolization and thirty-three who underwent conventional chemoembolization between June 2006 and December 2011. The radiological response was reassessed using the modified Response Evaluation Criteria in Solid Tumors. The sustained complete response, time to progression and overall survival rates were also analyzed. RESULTS: Complete response rates were significantly higher in patients who had undergone modified chemoembolization compared to those who had undergone conventional treatment (61.7% and 24.3%, respectively; p<0.001). The rate of sustained complete response was significantly higher in the modified chemoembolization group compared to the conventional chemoembolization group (median of 236 and 37 days, respectively; p<0.001). Time to progression was significantly higher in the modified chemoembolization group compared to the conventional chemoembolization group (median of 424 and 201 days, respectively; p=0.042). Overall survival rates revealed no difference between patients who received modified chemoembolization and conventional chemoembolization (median of 483 and 399 days, respectively; p=0.316). CONCLUSION: Transarterial chemoembolization modified by n-butyl cyanoacrylate addition was superior to conventional transarterial chemoembolization in terms of the

  4. Potential biofuel additive from renewable sources--Kinetic study of formation of butyl acetate by heterogeneously catalyzed transesterification of ethyl acetate with butanol.

    PubMed

    Ali, Sami H; Al-Rashed, Osama; Azeez, Fadhel A; Merchant, Sabiha Q

    2011-11-01

    Butyl acetate holds great potential as a sustainable biofuel additive. Heterogeneously catalyzed transesterification of biobutanol and bioethylacetate can produce butyl acetate. This route is eco-friendly and offers several advantages over the commonly used Fischer Esterification. The Amberlite IR 120- and Amberlyst 15-catalyzed transesterification is studied in a batch reactor over a range of catalyst loading (6-12 wt.%), alcohol to ester feed ratio (1:3 to 3:1), and temperature (303.15-333.15K). A butanol mole fraction of 0.2 in the feed is found to be optimum. Amberlite IR 120 promotes faster kinetics under these conditions. The transesterifications studied are slightly exothermic. The moles of solvent sorbed per gram of catalyst decreases (ethanol>butanol>ethyl acetate>butyl acetate) with decrease in solubility parameter. The dual site models, the Langmuir Hinshelwood and Popken models, are the most successful in correlating the kinetics over Amberlite IR 120 and Amberlyst 15, respectively.

  5. Ecotoxicological evaluation of the additive butylated hydroxyanisole using a battery with six model systems and eighteen endpoints.

    PubMed

    Jos, Angeles; Repetto, Guillermo; Ríos, Juan Carlos; del Peso, Ana; Salguero, Manuel; Hazen, María José; Molero, María Luisa; Fernández-Freire, Paloma; Pérez-Martín, Jose Manuel; Labrador, Verónica; Cameán, Ana

    2005-01-26

    The occurrence and fate of additives in the aquatic environment is an emerging issue in environmental chemistry. This paper describes the ecotoxicological effects of the commonly used additive butylated hydroxyanisole (BHA) using a test battery, comprising of several different organisms and in vitro test systems, representing a proportion of the different trophic levels. The most sensitive system to BHA was the inhibition of bioluminescence in Vibrio fischeri bacteria, which resulted in an acute low observed adverse effect concentration (LOAEC) of 0.28 microM. The next most sensitive system was the immobilization of the cladoceran Daphnia magna followed by: the inhibition of the growth of the unicellular alga Chlorella vulgaris; the endpoints evaluated in Vero (mammalian) cells (total protein content, LDH activity, neutral red uptake and MTT metabolization), mitotic index and root growth inhibition in the terrestrial plant Allium cepa, and finally, the endpoints used on the RTG-2 salmonid fish cell line (neutral red uptake, total protein content, MTS metabolization, lactate dehydrogenase leakage and activity, and glucose-6-phosphate dehydrogenase activity). Morphological alterations in RTG-2 cells were also assessed and these included loss of cells, induction of cellular pleomorphism, hydropic degeneration and induction of apoptosis at high concentrations. The results from this study also indicated that micronuclei were not induced in A.cepa exposed to BHA. The differences in sensitivity for the diverse systems that were used (EC50 ranged from 1.2 to >500 microM) suggest the importance for a test battery approach in the evaluation of the ecological consequences of chemicals. According to the results, the levels of BHA reported in industrial wastewater would elicit adverse effects in the environment. This, coupled with its potential to bioaccumulate, makes BHA a pollutant of concern not only for acute exposures, but also for the long-term. PMID:15642642

  6. Molecular dynamics simulations for the examination of mechanical properties of hydroxyapatite/ poly α-n-butyl cyanoacrylate under additive manufacturing.

    PubMed

    Wang, Yanen; Wei, Qinghua; Pan, Feilong; Yang, Mingming; Wei, Shengmin

    2014-01-01

    Molecular dynamics (MD) simulations emerged to be a helpful tool in the field of material science. In rapid prototyping artificial bone scaffolds process, the binder spraying volume and mechanism are very important for bone scaffolds mechanical properties. In this study, we applied MD simulations to investigating the binding energy of α-n-butyl cyanoacrylate (NBCA) on Hydroxyapatite (HA) crystallographic planes (001, 100 and 110), and to calculating and analyzing the mechanical properties and radial distribution function of the HA(110)/NBCA mixed system. The simulation results suggested that HA (110) has the highest binding energy with NBCA owing to the high planar atom density, and the mechanical properties of HA(110)/NBCA mixed system is stronger than pure HA system. Therefore, the multi-grade strength bone scaffold could be fabricated through spraying various volume NBCA binders during 3D printing process. By calculating the radial distribution function of HA(110)/NBCA, the essence of the interface interaction were successfully elucidated. The forming situation parameters can be referred to calculation results. There exists a strong interaction between HA crystallographic plane (110) and NBCA, it is mainly derived from the hydrogen bonds between O atoms which connect with C atoms of NBCA and H atoms in HA crystal. Furthermore, a strong adsorption effect can be demonstrated between HA and NBCA.

  7. Simultaneous determination of antioxidants, preservatives and sweeteners permitted as additives in food by mixed micellar electrokinetic chromatography.

    PubMed

    Boyce, M C

    1999-06-25

    A micellar electrokinetic chromatography method was developed to simultaneously analyse commonly used food additives. The additive mixture, comprising propyl gallate, octyl gallate, dodecyl gallate, butylated hydroxyanisole, butylated hydroxytoluene, tertiary butylhydroquinone, p-hydroxybenzoic acid methyl ester, p-hydroxybenzoic acid ethyl ester, benzoic acid, sorbic acid, saccharin, aspartame and acesulfame-K, was not resolved using single surfactant micellar systems consisting of sodium dodecyl sulfate (SDS), sodium cholate (SC) or sodium deoxycholate (SDC). The separation of these additives using mixed micellar systems, involving SDS/SC, SDS/SDC and SC/SDC, was investigated. Organic solvents were added to the mixed micellar phases to optimise the separation. The mixture was successfully separated using a 20 mM borate buffer with 35 mM SC, 15 mM SDS and 10% methanol added at pH 9.3. Additives in cola beverages and low-joule jam were investigated and quantified using this method.

  8. Analysis of baicalein, baicalin and wogonin in Scutellariae radix and its preparation by microemulsion electrokinetic chromatography with 1-butyl-3-methylimizolium tetrafluoborate ionic liquid as additive.

    PubMed

    Zhang, Huige; Tian, Kan; Tang, Jianghong; Qi, Shengda; Chen, Hongli; Chen, Xingguo; Hu, Zhide

    2006-10-01

    Microemulsion electrokinetic chromatography (MEEKC) using 1-butyl-3-methylimidazolium tetrafluoroborate (BMIM-BF4) ionic liquid (IL) as additive was developed for the analysis of baicalin, wogonin and baicalein in Scutellariae radix and its preparation. After conducting a series of optimizations, baseline separation was obtained for the analytes within 5min under the optimum conditions (sodium dodecyl sulfate (SDS) 0.88% (m/v) ethyl acetate 0.8% (v/v) butan-1-ol 0.2% (v/v) and the buffer composition were 25% acetonitrile (v/v), 7.5 mM BMIM-BF4 and 10 mM NaH2PO4, pH 8.2, applied voltage 17.5 kV and detection at 254 nm), the method has been successfully applied to the determination and quantification of the analytes in the extracts of S. radix (cooked), S. radix (raw) and Qingfeiyihuowan which was the preparation including S. radix. PMID:16952364

  9. Butylated hydroxyanisole and lung tumor development in A/J mice

    SciTech Connect

    Witschi, H.R.; Doherty, D.G.

    1984-01-01

    A diet containing 0.75% butylated hydroxyanisole (BHA) did not enhance the development of lung tumors in A/J mice if fed for 8 weeks after administration of urethane, benzo(a)pyrene (B(a)P), or dimethylnitrosamine (DMN). Prefeeding animals with BHA partially protected animals against the tumorigenic effect of urethane and B(a)P. Partial protection was also seen in animals given B(a)P and then exposed to BHA in the diet. The two isomers of BHA 3-tert.-butyl-4-hydroxyanisole and 2-tert.-butyl-4-hydroxyanisole) were synthesized and injected ip. They failed to enhance lung tumor development. It is concluded that BHA is not a promoting agent as is butylated hydroxytoluene (BHT) for lung tumors in mice. One possible explanation is that BHA in the diet does not produce the extensive cell proliferation seen in the lungs of mice fed BHT. 19 references, 5 tables.

  10. The Quantitative Determination of Butylated Hydroxytoluene in Chewing Gum Using GC--MS

    ERIC Educational Resources Information Center

    Witter, A. E.

    2005-01-01

    The experiment to measure concentration of Photophysical Characterization(BHT) and determine percent recovery in chewing gum is described. The results demonstrated that over time, the concentration of BHT in the extract decreased owing to aerial oxidation.

  11. Protective effect of butylated hydroxytoluene on sperm function in human spermatozoa cryopreserved by vitrification technique.

    PubMed

    Merino, O; Aguagüiña, W E; Esponda, P; Risopatrón, J; Isachenko, E; Isachenko, V; Sánchez, R

    2015-03-01

    Butylhydroxytoluene (BHT), a synthetic analogue of vitamin E, shows antioxidant and antiviral properties and has been successfully used for mammalian sperm cryopreservation. In this study, BHT was included in a vitrification solution to determine its cryoprotective effect on human spermatozoa. Spermatozoa were selected by swim-up and vitrified in close sealed straw using either a combination of human tubal fluid (HTF), sucrose and BHT 1 mm (VMBHT), or only HTF and sucrose (VM). The optimal concentration of BHT was determined by the observation of preserved progressive sperm motility (PSM) after warming and detection of plasma membrane (PMI), membrane mitochondrial potential (ΔΨm) and DNA integrity. The presence of reactive oxygen species (ROS) was also detected. The PSM was significantly higher in the VMBHT group (80.86 ± 5.41%) compared with the VM group (68.9 ± 3.67%) (P < 0.05). Butylhydroxytoluene significantly preserved DNA integrity (4.0 ± 0.1% versus 6.1 ± 1.6%; P < 0.05) and reduced ROS production (5.5 ± 2.2 versus 8.6 ± 1.8%; P < 0.05). Plasma membrane and ΔΨm showed no statistical differences. One millimolar BHT effectively maintained cell function and due to its antioxidant and antiviral properties could be used in semen cryopreservation of patients with viral infections transmitted by seminal plasma.

  12. Drugs, food additives and natural products as promoters in rat urinary bladder carcinogenesis.

    PubMed

    Ito, N; Fukushima, S; Shirai, T; Hagiwara, A; Imaida, K

    1984-01-01

    The promoting effects of various chemicals on urinary bladder carcinogenesis in rats initiated with N-butyl-N-(4-hydroxybutyl)nitrosamine (BBN) were studied. Male Fischer 344 rats were given BBN at 0.01% or 0.05% in their drinking-water for four weeks. One of the following chemicals was then administered in the diet for 32 or 34 weeks: acetazolamide, allopurinol, phenobarbital, phenacetin, ortho-phenylphenol, sodium ortho-phenylphenate, diphenyl, sodium L-ascorbate, butylated hydroxyanisole, butylated hydroxytoluene, sodium saccharin, aspartame, sodium cyclamate, stevioside, DL-tryptophan, quercetin, caffeine, nicotine and hippuric acid. Phenacetin, sodium ortho-phenylphenate, sodium L-ascorbate and butylated hydroxyanisole were significant promoters of urinary bladder neoplasia in rats initiated with BBN. Sodium saccharin, diphenyl, butylated hydroxytoluene, allopurinol, and DL-tryptophan caused moderate or slight promotion of neoplastic changes in the experimental animals. No change in tumour yield was observed after administration of the other chemicals.

  13. Decrease of droplet size of the reverse microemulsion 1-butyl-3-methylimidazolium tetrafluoroborate/Triton X-100/cyclohexane by addition of water.

    PubMed

    Gao, Yanan; Hilfert, Liane; Voigt, Andreas; Sundmacher, Kai

    2008-03-27

    In the present contribution, results concerning the role of small amounts of water in the 1-butyl-3-methylimidazolium tetrafluoroborate (bmimBF4)-in-cyclohexane ionic liquid (IL) reverse microemulsions are reported. Dynamic light scattering (DLS) revealed that the size of microemulsion droplets decreased remarkably with increasing water content although water is often used as a polar component to swell reverse microemulsions. It was thus deduced that the number of microemulsion droplets was increased which was confirmed by conductivity measurements. The states of dissolved water were investigated by Fourier transform IR (FTIR) spectroscopic analysis showing that water molecules mainly act as bound water. 1H NMR along with two-dimensional rotating frame nuclear Overhauser effect (NOE) experiments (ROESY) further revealed that water molecules were mainly located in the periphery of the polar core of the microemulsion droplets and behave like a chock being inserted in the palisade layer of the droplet. This increased the curvature of the surfactant film at the IL/cyclohexane interface and thus led to the decrease of the microemulsion droplet size. The order of surfactant molecules arranged in the interface film was increased and thus induced a loss of entropy. Isothermal titration calorimetry (ITC) indicated that an enthalpy increase compensates for the loss of entropy during the process of microstructural transition. PMID:18318531

  14. Synthesis, characterization, and evaluation of 10-undecenoic acid-based epithio derivatives as multifunctional additives.

    PubMed

    Geethanjali, Gorla; Padmaja, Korlipara V; Sammaiah, Arukali; Prasad, Rachapudi B N

    2014-11-26

    Novel epithio compounds from alkyl epoxy undecanoates (n-alkyl, C1, C4, and C6; isoalkyl, C3, C4, and C8) were synthesized using an ammonium thiocyanate in ionic liquid 1-methylimidazolium tetrafluoroborate/H2O (2:1) solvent system in 85-90% yields by gas chromatographic (GC) analysis. The synthesized products were characterized by (1)H and (13)C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy (FTIR), gas chromatography, and GC mass spectral (GC-MS) analyses and evaluated for their antioxidant, extreme pressure (EP), and antiwear (AW) properties in three different base oils, namely, epoxy jatropha fatty acid n-butyl esters (EJB), di-2-ethylhexyl sebacate (DOS), and mineral oil (S-105). Among the synthesized products, n-butyl epithio undecanoate exhibited superior antioxidant property (229.2 °C) compared to butylated hydroxytoluene (BHT, 193.8 °C) in base oil DOS and comparable performance in EJB and S-105 base oils. All of the epithio derivatives exhibited significantly enhanced weld point for the base oils EJB and DOS at 2 wt % level and displayed moderate enhancement in S-105 base oil. Methyl epithio undecanoate at 0.6% concentration exhibited considerable improvement in the wear scar of DOS base oil. The synthesized epithio derivatives have potential as multifunctional additives in lubricant formulations.

  15. Transition-metal-free synthesis of aryl-substituted tert-butyl ynol ethers through addition/elimination substitution at an sp centre.

    PubMed

    Gray, Vincent J; Slater, Ben; Wilden, Jonathan D

    2012-12-01

    Nucleophilic attack of an alkoxide on an alkynyl sulfonamide leads to displacement of the sulfonamide at the sp centre and isolation of the ynol ether in good yield in a single operation. The mechanistic pathway has been probed by the use of coordinating additives, (13)C-labelling experiments and ab initio calculations, which indicated that an addition/elimination mechanism is in operation. PMID:23086681

  16. Evaluation of certain food additives. Fifty-first report of the Joint FAO/WHO Expert Committee on Food Additives.

    PubMed

    2000-01-01

    This report presents the conclusions of a Joint FAO/WHO Expert Committee convened to evaluate the safety of various food additives, with a view to recommending Acceptable Daily Intakes (ADIs) for humans, and to prepare specifications for the identity and purity of food additives. The first part of the report contains a general discussion of the principles governing the toxicological evaluation of food additives, the assessment of intake of food additives, and the establishment and revision of specifications, including comments concerning enzyme preparations derived from genetically modified microorganisms and limits for heavy metals. A summary follows of the Committee's evaluations of toxicological data on specific food additives, including enzyme preparations (alpha-acetolactate decarboxylase and maltogenic amylase), flavouring agents (trans-anethole, furfural and menthol), food colours (curcumin and riboflavin from genetically modified Bacillus subtilis), glazing agents (medium- and low-viscosity mineral oils), preservatives (sulfur dioxide and sulfites), a sweetening agent (stevioside), thickening agents (carrageenan, processed Eucheuma seaweed and enzymatically hydrolysed sodium carboxymethyl cellulose), gamma-cyclodextrin, glucono-delta-lactone and the calcium, magnesium, potassium and sodium salts of gluconic acid, and polyglycitol syrup. The Committee also evaluated the safety of various groups of flavouring agents and assessed the intake of specific food additives, including benzoates, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), sulfites and tert-butylhydroquinone (TBHQ). Annexed to the report are tables summarizing the Committee's recommendations for ADIs of the food additives considered, changes in the status of specifications for these substances and specific flavouring agents, and further toxicological studies and other information required or desired. PMID:10876377

  17. Evaluation of certain food additives. Fifty-first report of the Joint FAO/WHO Expert Committee on Food Additives.

    PubMed

    2000-01-01

    This report presents the conclusions of a Joint FAO/WHO Expert Committee convened to evaluate the safety of various food additives, with a view to recommending Acceptable Daily Intakes (ADIs) for humans, and to prepare specifications for the identity and purity of food additives. The first part of the report contains a general discussion of the principles governing the toxicological evaluation of food additives, the assessment of intake of food additives, and the establishment and revision of specifications, including comments concerning enzyme preparations derived from genetically modified microorganisms and limits for heavy metals. A summary follows of the Committee's evaluations of toxicological data on specific food additives, including enzyme preparations (alpha-acetolactate decarboxylase and maltogenic amylase), flavouring agents (trans-anethole, furfural and menthol), food colours (curcumin and riboflavin from genetically modified Bacillus subtilis), glazing agents (medium- and low-viscosity mineral oils), preservatives (sulfur dioxide and sulfites), a sweetening agent (stevioside), thickening agents (carrageenan, processed Eucheuma seaweed and enzymatically hydrolysed sodium carboxymethyl cellulose), gamma-cyclodextrin, glucono-delta-lactone and the calcium, magnesium, potassium and sodium salts of gluconic acid, and polyglycitol syrup. The Committee also evaluated the safety of various groups of flavouring agents and assessed the intake of specific food additives, including benzoates, butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT), sulfites and tert-butylhydroquinone (TBHQ). Annexed to the report are tables summarizing the Committee's recommendations for ADIs of the food additives considered, changes in the status of specifications for these substances and specific flavouring agents, and further toxicological studies and other information required or desired.

  18. Evaluation of the antioxidant properties of Mediterranean and tropical fruits compared with common food additives.

    PubMed

    Murcia, M A; Jiménez, A M; Martínez-Tomé, M

    2001-12-01

    Several Mediterranean and tropical fruits have been analyzed in order to assess their antioxidant activity compared with that of common food additives (butylated hydroxyanisole [BHA], butylated hydroxytoluene [BHT] and propyl gallate). Among Mediterranean fruits, red grape and plum were more effective (P < 0.05) scavengers of peroxyl radicals than BHA, BHT, and propyl gallate. Of the tropical fruits, banana was the most effective scavenger of peroxyl radicals. Mediterranean and tropical fruits showed very good scavenger activity against hydroxy radicals (OH*), protecting deoxyribose better than BHA and BHT. The HOCI scavenging ability of Mediterranean fruits tested was, in decreasing order, lemon > plum > apricot > white grape > melon > red grape > mandarin > watermelon > peach > medlar > apple > orange > cherry > strawberry. However, the four varieties of pear were poor scavengers (P < 0.05). Among tropical fruits, the order of efficiency as HOCI scavengers was passion fruit > lime > passiflora > kumquat > avocado > pineapple > physalis > papaya fruit > carambola > mango > banana. All Mediterranean fruits showed an effect on hydrogen peroxide except peach. Tropical fruits also had a strong effect on hydrogen peroxide except avocado, which had no effect. The effect of Mediterranean and tropical fruits on the protection factor of refined olive oil, analyzed by the Rancimat method and compared with common food additives, was clear. Watermelon conferred a significantly (P < 0.05) greater protection than the other Mediterranean fruits. Among tropical fruits, physalis had the most stabilizing effect.

  19. Additives

    NASA Technical Reports Server (NTRS)

    Smalheer, C. V.

    1973-01-01

    The chemistry of lubricant additives is discussed to show what the additives are chemically and what functions they perform in the lubrication of various kinds of equipment. Current theories regarding the mode of action of lubricant additives are presented. The additive groups discussed include the following: (1) detergents and dispersants, (2) corrosion inhibitors, (3) antioxidants, (4) viscosity index improvers, (5) pour point depressants, and (6) antifouling agents.

  20. Butyl benzyl phthalate

    Integrated Risk Information System (IRIS)

    Butyl benzyl phthalate ; CASRN 85 - 68 - 7 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinog

  1. Comparative antioxidant effect of aqueous extracts of curry leaves, fenugreek leaves and butylated hydroxytoluene in raw chicken patties.

    PubMed

    Devatkal, Suresh K; Thorat, Pramod R; Manjunatha, M; Anurag, Rahul K

    2012-12-01

    Antioxidant properties and use of aqueous extracts of curry leaves (Murraya koenigii) and fenugreek leaves (Trigonella foenum-graecum) as source of natural antioxidant in raw chicken meat were evaluated. Four treatments viz., I. Control (meat +2% salt), II.BHT (meat +2% salt +0.1% BHT), III. CLE (meat +2% salt +2% curry leaves extract) and IV. FLE (meat +2% salt +2% fenugreek leaves extract) were compared for lipid oxidation during eight days refrigerated storage. The average phenolic content was 59.2 and 52.8 mg/g gallic acid equivalent in CLE and FLE respectively. Free radical scavenging activity was 61.4 and 64.2% in CLE and FLE, respectively. CLE had significantly (P < 0.05) higher reducing activity (2.4) as compared to FLE (2.2). Observation on lipid oxidation showed a significant (p < 0.05) higher TBARS values in control patties than other patties containing BHT, CLE and FLE. Overall percent increase during storage period was highest in control followed by BHT, CLE and FLE. Both synthetic antioxidants and natural extracts significantly (p < 0.05) decreased the TBARS values. The average percent decrease in TBARS values during storage was 18, 25.5 and 27.5 in BHT, CLE and FLE treatments, respectively. Therefore, it was concluded that water extracts obtained from curry leaves and fenugreek leaves could be explored as natural antioxidants in poultry meat and meat products. PMID:24293699

  2. Comparative antioxidant effect of aqueous extracts of curry leaves, fenugreek leaves and butylated hydroxytoluene in raw chicken patties.

    PubMed

    Devatkal, Suresh K; Thorat, Pramod R; Manjunatha, M; Anurag, Rahul K

    2012-12-01

    Antioxidant properties and use of aqueous extracts of curry leaves (Murraya koenigii) and fenugreek leaves (Trigonella foenum-graecum) as source of natural antioxidant in raw chicken meat were evaluated. Four treatments viz., I. Control (meat +2% salt), II.BHT (meat +2% salt +0.1% BHT), III. CLE (meat +2% salt +2% curry leaves extract) and IV. FLE (meat +2% salt +2% fenugreek leaves extract) were compared for lipid oxidation during eight days refrigerated storage. The average phenolic content was 59.2 and 52.8 mg/g gallic acid equivalent in CLE and FLE respectively. Free radical scavenging activity was 61.4 and 64.2% in CLE and FLE, respectively. CLE had significantly (P < 0.05) higher reducing activity (2.4) as compared to FLE (2.2). Observation on lipid oxidation showed a significant (p < 0.05) higher TBARS values in control patties than other patties containing BHT, CLE and FLE. Overall percent increase during storage period was highest in control followed by BHT, CLE and FLE. Both synthetic antioxidants and natural extracts significantly (p < 0.05) decreased the TBARS values. The average percent decrease in TBARS values during storage was 18, 25.5 and 27.5 in BHT, CLE and FLE treatments, respectively. Therefore, it was concluded that water extracts obtained from curry leaves and fenugreek leaves could be explored as natural antioxidants in poultry meat and meat products.

  3. Individual and combined in vitro (anti)androgenic effects of certain food additives and cosmetic preservatives.

    PubMed

    Pop, Anca; Drugan, Tudor; Gutleb, Arno C; Lupu, Diana; Cherfan, Julien; Loghin, Felicia; Kiss, Béla

    2016-04-01

    The individual and combined (binary mixtures) (anti)androgenic effect of butylparaben (BuPB), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and propyl gallate (PG) was evaluated using the MDA-kb2 cell line. Exposing these cells to AR agonists results in the expression of the reporter gene (encoding for luciferase) and luminescence can be measured in order to monitor the activity of the reporter protein. In case of the evaluation of the anti-androgenic effect, the individual test compounds or binary mixtures were tested in the presence of a fixed concentration of a strong AR agonist (1000 pM 5-alpha-dihydrotestosterone; DHT). Cell viability was assessed using a resazurin based assay. For PG, this is the first report in the literature concerning its (anti)androgenic activity. In case of both individual and mixture testing none of the compounds or binary combinations showed androgenic activity. When tested in the presence of DHT, BuPB, BHA and BHT proved to be weak anti-androgens and this was confirmed during the evaluation of binary mixtures (BuPB+BHA, BuPB+BHT and BHA+BHT). Besides performing the in vitro testing of the binary combinations, two mathematical models (dose addition and response addition) were evaluated in terms of accuracy of prediction of the anti-androgenic effect of the selected binary mixtures. The dose addition model guaranteed a good correlation between the experimental and predicted data. However, no estimation was possible in case of mixtures containing PG, due to the lack of effect of the compound in case of the individual testing.

  4. Individual and combined in vitro (anti)androgenic effects of certain food additives and cosmetic preservatives.

    PubMed

    Pop, Anca; Drugan, Tudor; Gutleb, Arno C; Lupu, Diana; Cherfan, Julien; Loghin, Felicia; Kiss, Béla

    2016-04-01

    The individual and combined (binary mixtures) (anti)androgenic effect of butylparaben (BuPB), butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and propyl gallate (PG) was evaluated using the MDA-kb2 cell line. Exposing these cells to AR agonists results in the expression of the reporter gene (encoding for luciferase) and luminescence can be measured in order to monitor the activity of the reporter protein. In case of the evaluation of the anti-androgenic effect, the individual test compounds or binary mixtures were tested in the presence of a fixed concentration of a strong AR agonist (1000 pM 5-alpha-dihydrotestosterone; DHT). Cell viability was assessed using a resazurin based assay. For PG, this is the first report in the literature concerning its (anti)androgenic activity. In case of both individual and mixture testing none of the compounds or binary combinations showed androgenic activity. When tested in the presence of DHT, BuPB, BHA and BHT proved to be weak anti-androgens and this was confirmed during the evaluation of binary mixtures (BuPB+BHA, BuPB+BHT and BHA+BHT). Besides performing the in vitro testing of the binary combinations, two mathematical models (dose addition and response addition) were evaluated in terms of accuracy of prediction of the anti-androgenic effect of the selected binary mixtures. The dose addition model guaranteed a good correlation between the experimental and predicted data. However, no estimation was possible in case of mixtures containing PG, due to the lack of effect of the compound in case of the individual testing. PMID:26812027

  5. Effect of Addition of Natural Antioxidants on the Shelf-Life of "Chorizo", a Spanish Dry-Cured Sausage.

    PubMed

    Pateiro, Mirian; Bermúdez, Roberto; Lorenzo, José Manuel; Franco, Daniel

    2015-01-01

    The dose effect of the addition of natural antioxidants (tea, chestnut, grape seed and beer extracts) on physicochemical, microbiological changes and on oxidative stability of dry-cured "chorizo", as well as their effect during the storage under vacuum conditions was evaluated. Color parameters were significantly (p < 0.05) affected by the addition of antioxidants so that samples that contained antioxidants were more effective in maintaining color. The improving effects were dose-dependent with highest values with the dose of 50 mg/kg during ripening and depend on the extract during vacuum packaging. Addition of antioxidants decreased (p < 0.05) the oxidation, showing thiobarbituric acid reactive substances (TBARS) values below 0.4 mg MDA/kg. Natural antioxidants matched or even improved the results obtained for butylated hydroxytoluene (BHT). Regarding texture profile analysis (TPA) analysis, hardness values significantly (p < 0.001) decreased with the addition of antioxidants, obtaining the lower results with the dose of 200 mg/kg both during ripening and vacuum packaging. Antioxidants reduced the counts of total viable counts (TVC), lactic acid bacteria (LAB), mold and yeast. Free fatty acid content during ripening and under vacuum conditions showed a gradual and significant (p < 0.05) release as a result of lipolysis. At the end of ripening, the addition of GRA1000 protected chorizos from oxidative degradation. PMID:26785337

  6. Toxicogenomics concepts and applications to study hepatic effects of food additives and chemicals

    SciTech Connect

    Stierum, Rob . E-mail: stierum@voeding.tno.nl; Heijne, Wilbert; Kienhuis, Anne; Ommen, Ben van; Groten, John

    2005-09-01

    Transcriptomics, proteomics and metabolomics are genomics technologies with great potential in toxicological sciences. Toxicogenomics involves the integration of conventional toxicological examinations with gene, protein or metabolite expression profiles. An overview together with selected examples of the possibilities of genomics in toxicology is given. The expectations raised by toxicogenomics are earlier and more sensitive detection of toxicity. Furthermore, toxicogenomics will provide a better understanding of the mechanism of toxicity and may facilitate the prediction of toxicity of unknown compounds. Mechanism-based markers of toxicity can be discovered and improved interspecies and in vitro-in vivo extrapolations will drive model developments in toxicology. Toxicological assessment of chemical mixtures will benefit from the new molecular biological tools. In our laboratory, toxicogenomics is predominantly applied for elucidation of mechanisms of action and discovery of novel pathway-supported mechanism-based markers of liver toxicity. In addition, we aim to integrate transcriptome, proteome and metabolome data, supported by bioinformatics to develop a systems biology approach for toxicology. Transcriptomics and proteomics studies on bromobenzene-mediated hepatotoxicity in the rat are discussed. Finally, an example is shown in which gene expression profiling together with conventional biochemistry led to the discovery of novel markers for the hepatic effects of the food additives butylated hydroxytoluene, curcumin, propyl gallate and thiabendazole.

  7. 21 CFR 172.270 - Sulfated butyl oleate.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... FOR HUMAN CONSUMPTION (CONTINUED) FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN... transesterification of an edible vegetable oil using 1-butanol. Following sulfation, the reaction mixture is washed... oleate reaction mixture meets the following specifications: (1) Not less than 90 percent butyl oleate....

  8. 21 CFR 172.270 - Sulfated butyl oleate.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN CONSUMPTION Coatings, Films and Related Substances...-butanol. Following sulfation, the reaction mixture is washed with water and neutralized with aqueous sodium or potassium hydroxide. Prior to sulfation, the butyl oleate reaction mixture meets the...

  9. 21 CFR 172.270 - Sulfated butyl oleate.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... FOR HUMAN CONSUMPTION (CONTINUED) FOOD ADDITIVES PERMITTED FOR DIRECT ADDITION TO FOOD FOR HUMAN... transesterification of an edible vegetable oil using 1-butanol. Following sulfation, the reaction mixture is washed... oleate reaction mixture meets the following specifications: (1) Not less than 90 percent butyl oleate....

  10. Octacoordinated Dioxo-Molybdenum Complex via Formal Oxidative Addition of Molecular Oxygen. Studies of Chemical Reactions Between M(CO)6 (M = Cr, Mo) and 2,4-Di-tert-butyl-6-(pyridin-2-ylazo)-phenol.

    PubMed

    Chatterjee, Ipsita; Saha Chowdhury, Nabanita; Ghosh, Pradip; Goswami, Sreebrata

    2015-06-01

    Reactions of M(CO)6 (M = Mo, Cr) and 2 mol of 2,4-di-tert-butyl-6-(pyridin-2-ylazo)-phenol ligand (HL) in air yielded [Mo(VI)O2(L(1)¯)2], 1, and [Cr(III)(L(1)¯)(L(•2)¯)], 2, respectively, in high yields. Formation of the Cr-complex is a substitution reaction, which is associated with electron transfer, while that of Mo is an example of molecular oxygen activation. Isolated monoradical chromium complex 2 is susceptible to oxidation. Accordingly the reaction of 2 with the oxidant, I2 produces a cationic nonradical complex of chemical composition [Cr(III)(L(1)¯)2]I3, [2]I3 in almost quantitative yield. All the isolated complexes are primarily characterized by various spectroscopic techniques and magnetic measurements. While the molybdenum complex is diamagnetic, the two chromium complexes behave as simple paramagnets: μeff (295 K), 2.81 μB and 3.79 μB for 2 and [2]I3, respectively. Single-crystal three-dimensional X-ray structures of 1, 2, [2]I3 are reported. The geometry of the Mo-complex is square antiprism (octacoordination), and that of the Cr-complexes is distorted octahedral. Redox properties of the complexes are studied by cyclic voltammetry and constant potential coulometry. The data are analyzed based on density functional theoretical calculations of molecular orbitals of redox isomers of the Cr complexes. The results indicated that the redox events in the complexes occur at the ligand center. The oxidation state of Cr in 2 is further assessed by XPS measurements and compared with the reported systems.

  11. Sprayed Coating Renews Butyl Rubber

    NASA Technical Reports Server (NTRS)

    Martin, R. B.

    1982-01-01

    Damaged butyl rubber products are renewed by spray technique originally developed for protective suits worn by NASA workers. A commercial two-part adhesive is mixed with Freon-113 (or equivalent) trichlorotrifluoroethane to obtain optimum viscosity for spraying. Mix is applied with an external-air-mix spray gun.

  12. Effect of Addition of Natural Antioxidants on the Shelf-Life of “Chorizo”, a Spanish Dry-Cured Sausage

    PubMed Central

    Pateiro, Mirian; Bermúdez, Roberto; Lorenzo, José Manuel; Franco, Daniel

    2015-01-01

    The dose effect of the addition of natural antioxidants (tea, chestnut, grape seed and beer extracts) on physicochemical, microbiological changes and on oxidative stability of dry-cured “chorizo”, as well as their effect during the storage under vacuum conditions was evaluated. Color parameters were significantly (p < 0.05) affected by the addition of antioxidants so that samples that contained antioxidants were more effective in maintaining color. The improving effects were dose-dependent with highest values with the dose of 50 mg/kg during ripening and depend on the extract during vacuum packaging. Addition of antioxidants decreased (p < 0.05) the oxidation, showing thiobarbituric acid reactive substances (TBARS) values below 0.4 mg MDA/kg. Natural antioxidants matched or even improved the results obtained for butylated hydroxytoluene (BHT). Regarding texture profile analysis (TPA) analysis, hardness values significantly (p < 0.001) decreased with the addition of antioxidants, obtaining the lower results with the dose of 200 mg/kg both during ripening and vacuum packaging. Antioxidants reduced the counts of total viable counts (TVC), lactic acid bacteria (LAB), mold and yeast. Free fatty acid content during ripening and under vacuum conditions showed a gradual and significant (p < 0.05) release as a result of lipolysis. At the end of ripening, the addition of GRA1000 protected chorizos from oxidative degradation. PMID:26785337

  13. Chronic pulmonary dysfunction following acute inhalation of butyl acrylate.

    PubMed

    Bhardwaj, Ravindra; Ducatman, Alan; Finkel, Mitchell S; Petsonk, Edward; Hunt, Janet; Beto, Robert J

    2012-01-01

    Butyl Acrylate (BA) (2-propionic acid; CH2 = CHCOOC4H9) is a colorless liquid commonly used in impregnation agents and adhesives. Dermal contact with BA has previously been reported to cause moderate skin irritation with skin sensitizing potential in humans. Health effects of inhalation of BA have not been previously reported. Accordingly, we document the health conditions of a bystander, first responder and landfill worker exposed to butyl acrylate (BA) released to the atmosphere following a collision and roadside spill in October 1998. Retrospective data were collected via chart review and analyzed for exposure, symptoms, physical findings and radiological, laboratory and spirometry results over a ten-year period. All three patients had similar respiratory symptoms including a dramatic hacking cough and dyspnea. Findings included abnormal pulmonary function tests and breath sounds. These data underscore the potential hazards of BA inhalational exposure and the need to wear additional protective equipment. PMID:23472539

  14. Reactivities of Substituted α-Phenyl-N-tert-butyl Nitrones

    PubMed Central

    2015-01-01

    In this work, a series of α-phenyl-N-tert-butyl nitrones bearing one, two, or three substituents on the tert-butyl group was synthesized. Cyclic voltammetry (CV) was used to investigate their electrochemical properties and showed a more pronounced substituent effect for oxidation than for reduction. Rate constants of superoxide radical (O2•–) reactions with nitrones were determined using a UV–vis stopped-flow method, and phenyl radical (Ph•) trapping rate constants were measured by EPR spectroscopy. The effect of N-tert-butyl substitution on the charge density and electron density localization of the nitronyl carbon as well as on the free energies of nitrone reactivity with O2•– and HO2• were computationally rationalized at the PCM/B3LYP/6-31+G**//B3LYP/6-31G* level of theory. Theoretical and experimental data showed that the rates of the reaction correlate with the nitronyl carbon charge density, suggesting a nucleophilic nature of O2•– and Ph• addition to the nitronyl carbon atom. Finally, the substituent effect was investigated in cell cultures exposed to hydrogen peroxide and a correlation between the cell viability and the oxidation potential of the nitrones was observed. Through a combination of computational methodologies and experimental methods, new insights into the reactivity of free radicals with nitrone derivatives have been proposed. PMID:24968285

  15. Anaerobic degradation of methyl tert-butyl ether (MTBE) and tert-butyl alcohol (TBA).

    PubMed

    Finneran, K T; Lovley, D R

    2001-05-01

    The potential for anaerobic degradation of methyl tert-butyl ether (MTBE) and tert-butyl alcohol (TBA) was investigated in laboratory incubations of sediments from a petroleum-contaminated aquifer and in aquatic sediments. The addition of humic substances (HS) stimulated the anaerobic degradation of MTBE in aquifer sediments in which Fe(III) was available as an electron acceptor. This is attributed to the fact that HS and other extracellular quinones can stimulate the activity of Fe(III)-reducing microorganisms by acting as an electron shuttle between Fe(III)-reducing microorganisms and insoluble Fe(III) oxides. MTBE was not degraded in aquifer sediments without Fe(III) and HS. [14C]-MTBE added to aquatic sediments adapted for anaerobic MTBE degradation was converted to 14CO2 in the presence or absence of HS or the HS analog, anthraquione-2,6-disulfonate. Unamended aquatic sediments produced 14CH4 as well as 14CO2 from [14C]-MTBE. The aquatic sediments also rapidly consumed TBA under anaerobic conditions and converted [14C]-TBA to 14CH4 and 14CO2. An adaptation period of ca. 250-300 days was required prior to the most rapid anaerobic MTBE degradation in both sediment types, whereas TBA was metabolized in the aquatic sediments without a lag. These results demonstrate that, under the appropriate conditions, MTBE and TBA can be degraded in the absence of oxygen. This suggests that it may be possible to design strategies for the anaerobic remediation of MTBE in petroleum-contaminated subsurface environments.

  16. Accelerated aging of EPDM and butyl elastomers

    SciTech Connect

    Wilson, M.H.

    1996-06-01

    This study was composed of three parts: a post cure study to optimize final properties of an ethylene-propylene-diene (EPDM) formulation, an accelerated aging study to compare the stress relaxation behavior of a butyl and an EPDM elastomer under compression, and a cursory evaluation of a new 70 Shore A EPDM. The optimum postcure for the EPDM was found to be 2 to 4 hours at 182{degrees}C in a vacuum. The EPDM was also shown to have superior aging characteristics compared to the butyl and is recommended for use instead of the butyl material. The physical properties for new 70 Shore A EPDM are satisfactory, and the stress relaxation behavior was only slightly inferior to the other EPDM.

  17. Free radical scavenging abilities of flavonoids as mechanism of protection against mutagenicity induced by tert-butyl hydroperoxide or cumene hydroperoxide in Salmonella typhimurium TA102.

    PubMed

    Edenharder, R; Grünhage, D

    2003-09-01

    Mutagenicity induced by tert-butyl hydroperoxide (BHP) or cumene hydroperoxide (CHP) in Salmonella typhimurium TA102 was effectively reduced by flavonols with 3',4'-hydroxyl groups such as fisetin, quercetin, rutin, isoquercitrin, hyperoxide, myricetin, myricitrin, robinetin, and to a lesser extent also by morin and kaempferol (ID50=0.25-1.05 micromol per plate). With the exception of isorhamnetin, rhamnetin, morin, and kaempferol, closely similar results were obtained with both peroxides. Hydrogenation of the double bond between carbons 2 and 3 (dihydroquercetin, dihydrorobinetin) as well as the additional elimination of the carbonyl function at carbon 4 (catechins) resulted in a loss of antimutagenicity with the notable exception of catechin itself. Again, all flavones and flavanones tested were inactive except luteolin, luteolin-7-glucoside, diosmetin, and naringenin. The typical radical scavenger butylated hydroxytoluene also showed strong antimutagenicity against CHP (ID50=5.4 micromol per plate) and BHP (ID50=11.4 micromol per plate). Other lipophilic scavengers such as alpha-tocopherol and N,N'-diphenyl-1,4-phenylenediamine exerted only moderate effects, the hydrophilic scavenger trolox was inactive. The metal chelating agent 1,10-phenanthroline strongly reduced mutagenicities induced by CHP and BHP (ID50=2.75 and 2.5 micromol per plate) at low concentrations but induced mutagenic activities at higher concentrations. The iron chelator deferoxamine mesylate, however, was less effective in both respects. The copper chelator neocuproine effectively inhibited mutagenicity induced by BHP (ID50=39.7 micromol per plate) and CHP (ID50=25.9 micrommol per plate), the iron chelator 2,2'-dipyridyl was less potent (ID50=6.25 mmol per plate against BHP, 0.42 mmol per plate against CHP). In the absence of BHP and CHP, yet not in the presence of these hydroperoxides, quercetin, rutin, catechin, epicatechin, and naringenin induced strong mutagenic activities in S

  18. 40 CFR 721.4925 - Methyl n-butyl ketone.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Methyl n-butyl ketone. 721.4925... Substances § 721.4925 Methyl n-butyl ketone. (a) Chemical substance and significant new use subject to reporting. (1) The chemical substance methyl n-butyl ketone, CAS Number 591-78-6, is subject to...

  19. 40 CFR 721.4925 - Methyl n-butyl ketone.

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Methyl n-butyl ketone. 721.4925... Substances § 721.4925 Methyl n-butyl ketone. (a) Chemical substance and significant new use subject to reporting. (1) The chemical substance methyl n-butyl ketone, CAS Number 591-78-6, is subject to...

  20. 40 CFR 721.3438 - Chlorohydroxyalkyl butyl ether (generic).

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Chlorohydroxyalkyl butyl ether... Specific Chemical Substances § 721.3438 Chlorohydroxyalkyl butyl ether (generic). (a) Chemical substance... chlorohydroxyalkyl butyl ether (PMN P-99-1295) is subject to reporting under this section for the significant new...

  1. 40 CFR 721.3438 - Chlorohydroxyalkyl butyl ether (generic).

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Chlorohydroxyalkyl butyl ether... Specific Chemical Substances § 721.3438 Chlorohydroxyalkyl butyl ether (generic). (a) Chemical substance... chlorohydroxyalkyl butyl ether (PMN P-99-1295) is subject to reporting under this section for the significant new...

  2. Methyl tert-butyl ether (MTBE)

    Integrated Risk Information System (IRIS)

    Methyl tert - butyl ether ( MTBE ) ; CASRN 1634 - 04 - 4 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments f

  3. 21 CFR 582.3169 - Butylated hydroxyanisole.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Butylated hydroxyanisole. 582.3169 Section 582.3169 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical...

  4. 21 CFR 182.3169 - Butylated hydroxyanisole.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Butylated hydroxyanisole. 182.3169 Section 182.3169 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical Preservatives §...

  5. 21 CFR 582.3169 - Butylated hydroxyanisole.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Butylated hydroxyanisole. 582.3169 Section 582.3169 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical...

  6. 21 CFR 182.3169 - Butylated hydroxyanisole.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Butylated hydroxyanisole. 182.3169 Section 182.3169 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical...

  7. 21 CFR 582.3169 - Butylated hydroxyanisole.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Butylated hydroxyanisole. 582.3169 Section 582.3169 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical...

  8. 21 CFR 182.3169 - Butylated hydroxyanisole.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Butylated hydroxyanisole. 182.3169 Section 182.3169 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical...

  9. 21 CFR 182.3169 - Butylated hydroxyanisole.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Butylated hydroxyanisole. 182.3169 Section 182.3169 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) FOOD FOR HUMAN CONSUMPTION (CONTINUED) SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical...

  10. 21 CFR 582.3169 - Butylated hydroxyanisole.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Butylated hydroxyanisole. 582.3169 Section 582.3169 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical...

  11. 21 CFR 582.3169 - Butylated hydroxyanisole.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Butylated hydroxyanisole. 582.3169 Section 582.3169 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS SUBSTANCES GENERALLY RECOGNIZED AS SAFE Chemical...

  12. Methyl tert-butyl ether and tert-butyl alcohol degradation by Fusarium solani.

    PubMed

    Magaña-Reyes, Miguel; Morales, Marcia; Revah, Sergio

    2005-11-01

    Fusarium solani degraded methyl tert-butyl ether (MTBE) and other oxygenated compounds from gasoline including tert-butyl alcohol (TBA). The maximum degradation rate of MTBE was 16 mg protein h and 46 mg/g protein h for TBA. The culture transformed 77% of the total carbon to 14CO2. The estimated yield for MTBE was 0.18 g dry wt/g MTBE. PMID:16314973

  13. Short synthesis of tert-butyl-hydroxylated 3,5-di-tert-butyl-4-hydroxybenzaldehyde: Synthesis of tert-butyl-hydroxylated S-2474.

    PubMed

    Inagaki, Masanao; Matsumoto, Saichi; Tsuri, Tatsuo

    2003-02-01

    We have developed a very short synthesis of tert-butyl-hydroxylated di-tert-butyl-4-hydroxybenzaldehyde in which the HBr-DMSO system is used as an effective oxidant (overall yield of 45% for the entire four-step process from 2-tert-butyl-p-cresol). We also accomplished the synthesis of a major metabolite of the antiarthritic drug candidate S-2474. PMID:12558443

  14. DERMAL, ORAL AND INHALATION PHARMACOKINETICS OF METHYL TERTIARY-BUTYL ETHER (MTBE) IN HUMAN VOLUNTEERS

    EPA Science Inventory


    Methyl tertiary butyl ether (MTBE), a gasoline additive used to increase octane and reduce carbon monoxide emissions and ozone precursors, has contaminated drinking water and can lead to exposure by oral, inhalation, and dermal routes. To determine its dermal, oral, and inhal...

  15. DERMAL, ORAL, AND INHALATION PHARMACOKINETICS OF METHYL TERTIARY BUTYL ETHER (MTBE) IN HUMAN VOLUNTEERS

    EPA Science Inventory

    Methyl tertiary butyl ether (MTBE), a gasoline additive, used to increase octane and reduce carbon monoxide emissions and ozone precursors has contaminated drinking water leading to exposure by oral, inhalation, and dermal routes. To determine its dermal, oral, and inhalation ki...

  16. PHYSIOLOGICALLY BASED PHARMACOKINETIC MODEL FOR HUMAN EXPOSURES TO METHYL TERTIARY-BUTYL ETHER

    EPA Science Inventory

    Humans can be exposed by inhalation, ingestion, or dermal absorption to methyl tertiary-butyl ether (MTBE), an oxygenated fuel additive, from contaminated water sources. The purpose of this research was to develop a physiologically based pharmacokinetic model describing in human...

  17. OCCURRENCE OF METYL TERT-BUTYL ETHER (MTBE) AT FIVE MARINAS IN LAKE TEXOMA

    EPA Science Inventory



    Occurrence of methyl tert-butyl ether (MTBE) in five marinas was monitored between June 1999 and November 2000 in Lake Texoma located on the border of Oklahoma and Texas. MTBE is a commonly used gasoline additive and a suspected carcinogen. Lake water was collected at loc...

  18. ATTENUATION OF METHYL TERT-BUTYL ETHER IN WATER USING SUNLIGHT AND A PHOTOCATALYST

    EPA Science Inventory

    The use of methyl tert-butyl ether (MTBE) as a gasoline additive has resulted in increasing pollution of ground water. Most of the conventional treatment technologies are inefficient or costly when the initial concentration of MTBE is low (<200 ug/L). In order to find an eco-frie...

  19. Changes in oxygen consumption induced by t-butyl hydroperoxide in perfused rat liver. Effect of free-radical scavengers.

    PubMed Central

    Videla, L A; Villena, M I; Donoso, G; Giulivi, C; Boveris, A

    1984-01-01

    The addition of t-butyl hydroperoxide to perfused rat liver elicited a biphasic effect on hepatic respiration. A rapid fall in liver oxygen consumption was initially observed, followed by a recovery phase leading to respiratory rates higher than the initial steady-state values of oxygen uptake. This overshoot in hepatic oxygen uptake was abolished by free-radical scavengers such as (+)-cyanidanol-3 or butylated hydroxyanisole at concentrations that did not alter mitochondrial respiration. (+)-Cyanidanol-3 was also able to facilitate the recovery of respiration, the diminution in the calculated rate of hydroperoxide utilization and the decrease in liver GSH content produced by two consecutive pulses of t-butyl hydroperoxide. It is suggested that the t-butyl hydroperoxide-induced overshoot in liver respiration is related to increased utilization of oxygen for lipid peroxidation as a consequence of free radicals produced in the scission of the hydroperoxide by cellular haemoproteins. PMID:6508746

  20. Tetra­butyl­ammonium butyl­tetra­chlorido­stannate(IV)

    PubMed Central

    Diop, Tidiane; van der Lee, Arie; Diop, Libasse

    2013-01-01

    In the title compound, [N(C4H9)4][Sn(C4H9)Cl4], the SnIV atom of the stannate anion has a trigonal-bipyramidal coordination sphere by two Cl atoms and one butyl chain in the equatorial plane and by two Cl atoms in the apical positions. Two of the four butyl chains of the tetra­butyl­ammonium cation are partially disordered, each with refined site occupancies of 0.691 (6):0.309 (6). Weak C—H⋯Cl hydrogen-bonding inter­actions help to consolidate the crystal packing, as well as a short Cl⋯Cl inter­action of 3.295 (2) Å. PMID:24098187

  1. Physical-mechanical properties of Bis-EMA based root canal sealer with different fillers addition

    PubMed Central

    de Souza, Marcela Oliveira; Branco Leitune, Vicente Castelo; Bohn, Priscila Veit; Werner Samuel, Susana Maria; Collares, Fabrício Mezzomo

    2015-01-01

    Aim: To evaluate influence of three different filler particles on an experimental Bisphenol A ethoxylated dimethacrylate (Bis-EMA) based root filling material. Materials and Methods: Resin-based endodontic sealers were produced using Bis-EMA, camphorquinone, ethyl 4-dimethylaminobenzoate (EDAB), N, N-dihydroxyethyl-p-toluidine (DHEPT), butylated hydroxytoluene (BHT), and benzoyl peroxide. The experimental groups were formulated adding 10, 20, 30, 40, and 50% of calcium tungstate (CaWO4), ytterbium trifluoride(YbF3), and tantalum oxide(Ta2O5). Flow, thickness, and radiopacity tests were conducted in accordance with ISO 6876. Sorption and solubility (SL) tests were conducted in accordance with ISO 4049, pH was measured with a pH meter, and degree of conversion (DC) was evaluated with Fourier transform infrared spectroscopy (FTIR). For radiopacity, two-way analysis of variance (ANOVA) and Tukey's multiple comparison test was performed. For DC analysis, one-way ANOVA and Tukey's multiple comparison test was performed. All statistical analyses were performed with a significance level of 5%. Results: All groups showed lower flow with increased filler concentration. All groups showed film thickness values lower than 50μm, as ISO recommends, except CaWO450% group (76.7μm). pH values varied from 5.95 (± 0.07) in YbF340% group to 6.90 (± 0.07) in Ta2O540% group. In the radiopacity test, YbF330%, Ta2O540%, and Ta2O550% groups showed no statistical significant difference to 3mmAl. Ta2O5 and YbF3 groups in 10, 20, and 30% concentrations presented sorption and SL values as ISOrecommendation. Addition ofTa2O5 and CaWO4 decreased DC after 14 days. YbF3 addition showed no difference in DC from control group. Conclusion: YbF3 filler addition promoted higher properties compared to CaWO4 and Ta2O5 on Bis-EMA based root canal sealer. PMID:26069410

  2. Automatic mechanism generation for pyrolysis of di-tert-butyl sulfide.

    PubMed

    Class, Caleb A; Liu, Mengjie; Vandeputte, Aäron G; Green, William H

    2016-08-01

    The automated Reaction Mechanism Generator (RMG), using rate parameters derived from ab initio CCSD(T) calculations, is used to build reaction networks for the thermal decomposition of di-tert-butyl sulfide. Simulation results were compared with data from pyrolysis experiments with and without the addition of a cyclohexene inhibitor. Purely free-radical chemistry did not properly explain the reactivity of di-tert-butyl sulfide, as the previous experimental work showed that the sulfide decomposed via first-order kinetics in the presence and absence of the radical inhibitor. The concerted unimolecular decomposition of di-tert-butyl sulfide to form isobutene and tert-butyl thiol was found to be a key reaction in both cases, as it explained the first-order sulfide decomposition. The computer-generated kinetic model predictions quantitatively match most of the experimental data, but the model is apparently missing pathways for radical-induced decomposition of thiols to form elemental sulfur. Cyclohexene has a significant effect on the composition of the radical pool, and this led to dramatic changes in the resulting product distribution. PMID:27431650

  3. Theoretical calculations of hyperfine coupling constants for muoniated butyl radicals.

    PubMed

    Chen, Ya Kun; Fleming, Donald G; Wang, Yan Alexander

    2011-04-01

    The hyperfine coupling constants (HFCCs) of all the butyl radicals that can be produced by muonium (Mu) addition to butene isomers (1- and 2-butene and isobutene) have been calculated, to compare with the experimental results for the muon and proton HFFCs for these radicals reported in paper II (Fleming, D. G.; et al. J. Phys. Chem. A 2011, 10.1021/jp109676b) that follows. The equilibrium geometries and HFCCs of these muoniated butyl radicals as well as their unsubstituted isotopomers were treated at both the spin-unrestricted MP2/EPR-III and B3LYP/EPR-III levels of theory. Comparisons with calculations carried out for the EPR-II basis set have also been made. All calculations were carried out in vacuo at 0 K only. A C-Mu bond elongation scheme that lengthens the equilibrium C-H bond by a factor of 1.076, on the basis of recent quantum calculations of the muon HFCCs of the ethyl radical, has been exploited to determine the vibrationally corrected muon HFCCs. The sensitivity of the results to small variations around this scale factor was also investigated. The computational methodology employed was "benchmarked" in comparisons with the ethyl radical, both with higher level calculations and with experiment. For the β-HFCCs of interest, compared to B3LYP, the MP2 calculations agree better with higher level theories and with experiment in the case of the eclipsed C-Mu bond and are generally deemed to be more reliable in predicting the equilibrium conformations and muon HFCCs near 0 K, in the absence of environmental effects. In some cases though, the experimental results in paper II demonstrate that environmental effects enhance the muon HFCC in the solid phase, where much better agreement with the experimental muon HFCCs near 0 K is found from B3LYP than from MP2. This seemingly better level of agreement is probably fortuitous, due to error cancellations in the DFT calculations, which appear to mimic these environmental effects. For the staggered proton HFCCs of the

  4. Estimation of the dietary intake of 13 priority additives in France, Italy, the UK and Ireland as part of the FACET project.

    PubMed

    Vin, Karine; Connolly, Aileen; McCaffrey, Tracy; McKevitt, Aideen; O'Mahony, Cian; Prieto, Miguel; Tennant, David; Hearty, Aine; Volatier, Jean Luc

    2013-01-01

    The aim of this study was to assess the dietary exposure of 13 priority additives in four European countries (France, Italy, the UK and Ireland) using the Flavourings, Additives and Contact Materials Exposure Task (FACET) software. The studied additives were benzoates (E210-213), nitrites (E249-250) and sulphites (E220-228), butylated hydroxytoluene (E321), polysorbates (E432-436), sucroses esters and sucroglycerides (E473-474), polyglycerol esters of fatty acids (E475), stearoyl-lactylates (E481-482), sorbitan esters (E493-494 and E491-495), phosphates (E338-343/E450-452), aspartame (E951) and acesulfame (E950). A conservative approach (based on individual consumption data combined with maximum permitted levels (Tier 2)) was compared with more refined estimates (using a fitted distribution of concentrations based on data provided by the food industry (Tier 3)). These calculations demonstrated that the estimated intake is below the acceptable daily intake (ADI) for nine of the studied additives. However, there was a potential theoretical exceedance of the ADI observed for four additives at Tier 3 for high consumers (97.5th percentile) among children: E220-228 in the UK and Ireland, E432-436 and E481-482 in Ireland, Italy and the UK, and E493-494 in all countries. The mean intake of E493-494 could potentially exceed the ADI for one age group of children (aged 1-4 years) in the UK. For adults, high consumers only in all countries had a potential intake higher than the ADI for E493-494 at Tier 3 (an additive mainly found in bakery wares). All other additives examined had an intake below the ADI. Further refined exposure assessments may be warranted to provide a more in-depth investigation for those additives that exceeded the ADIs in this paper. This refinement may be undertaken by the introduction of additive occurrence data, which take into account the actual presence of these additives in the different food groups.

  5. Holographic Recording in Methacrylate Photopolymer Film Codoped with Benzyl n-Butyl Phthalate and Silica Nanoparticles

    NASA Astrophysics Data System (ADS)

    Takahashi, Hiroshi; Naito, Takahiro; Tomita, Yasuo

    2006-06-01

    Transmission volume holograms recorded in methacrylate photopolymer films codoped with benzyl n-butyl phthalate (BBP) and silica nanoparticles are studied. It is found that BBP, which is a well-known plasticizer, can be directly mixed with methacrylate monomer and that a refractive index modulation as high as ˜0.006 is recorded with a BBP concentration of 36 vol %. It is also found that the additional dispersion of silica nanoparticles substantially suppresses polymerization shrinkage without increasing optical scattering loss.

  6. DECISION-MAKING, SCIENCE AND GASOLINE ADDITIVES

    EPA Science Inventory


    Methyl-tert butyl ether (MTBE) has been used as a gasoline additive to serve two major purposes. The first use was as an octane-enhancer to replace organic lead, beginning in 1979. The second use, which began about 1992, was as an oxygenated additive to meet requirements ...

  7. Toxic effects of butyl elastomers on aerobic methane oxidation

    NASA Astrophysics Data System (ADS)

    Niemann, Helge; Steinle, Lea I.; Blees, Jan H.; Krause, Stefan; Bussmann, Ingeborg; Lehmann, Moritz F.; Treude, Tina

    2013-04-01

    Large quantities of the potent greenhouse gas methane are liberated into the water column of marine and lacustrine environments where it may be consumed by aerobic methane oxidising bacteria before reaching the atmosphere.The reliable quantification of aerobic methane oxidation (MOx) rates is consequently of paramount importance for estimating methane budgets and to understand the controls on water column methane cycling. A widely used set of methods for measuring MOx rates is based on the incubation of water samples during which the consumption of methane is monitored, for instance with radio-tracer assays. Typically, incubation vessels are sealed with butyl rubber stoppers because these elastomers are essentially impermeable for gases at the relevant time scales. We tested the effect of different stopper materials (unmodified- and halogenated butyl rubber) on MOx activity in environmental samples and in cultures of methane oxidising bacteria. MOx rates in samples sealed with unmodified butyl rubber were > 75% lower compared to parallel incubations with halogenated butyl rubber seals, suggesting inhibiting/toxic effects associated with the use of unmodified butyl elastomers. To further explore the cause of these effects, we analysed aqueous extracts of the different stoppers. Halogenated butyl rubber stoppers appeared to bleed off comparably little amounts of organics. In stark contrast, extracts of unmodified butyl rubber were contaminated with various organic compounds including potential bactericides such as benzyltoluenes, phenylalkanes and benzuothiazoles. We also found tetramethylthiourea, a scavenger of active oxygen species, which may inhibit the MOx pathway.

  8. MEASUREMENT OF EXHALED BREATH AND VENOUS BLOOD TO DEVELOP A PHYSIOLOGICALLY BASED PHARMACOKINETIC MODEL FOR HUMAN EXPOSURE TO METHYL TERTIARY-BUTYL ETHER AND THE PRODUCTION OF THE BIOMARKER TERTIARY-BUTYL ALCOHOL

    EPA Science Inventory

    Methyl tertiary-butyl ether (MTBE) is a common fuel additive used to increase the availability of oxygen in gasoline to reduce winter-time carbon monoxide emissions from automobiles. Also, MTBE boosts gasoline "octane" rating and, as such, allows reduction of benzene...

  9. WATER QUALITY AT FIVE MARINAS IN LAKE TEXOMA AS RELATED TO METHYL TERT-BUTYL ETHER (MTBE)

    EPA Science Inventory

    Occurrence of methyl tert-butyl ether (MTBE) in five marinas was monitored between June 1999 and November 2000 in Lake Texoma located on the border of Oklahoma and Texas. MTBE is a commonly used gasoline additive and a suspected carcinogen. Lake water was collected at locations i...

  10. Bioremediation of methyl tertiary-butyl ether (MTBE) by an innovative biofilter.

    PubMed

    Hu, C; Acuna-Askar, K; Englande, A J

    2004-01-01

    Methyl tertiary-butyl ether (MTBE) is a synthetic chemical used in unleaded gasoline as an additive to reduce levels of ozone and carbon monoxide from auto exhaust. Due to its chemical and recalcitrant properties, MTBE has caused groundwater contamination worldwide. A laboratory-scale biofilter made of a natural fiber (kenaf) mat and inoculated with MTBE-degrading microorganisms, was evaluated for MTBE removal efficiency. Operational parameters of oxygen flow rate, hydraulic retention time (HRT), yeast extract and initial MTBE concentration were varied and MTBE removal efficiencies determined. Four kinetic models were evaluated to describe the MTBE removal in the reactor. Formaldehyde and tertiary butyl alcohol (the most two reported MTBE biodegradation byproducts) were not found in the effluent; instead, carbon dioxide was monitored as the end product based on the results of a metabolic mass balance evaluation. Toxicity of treated effluent was evaluated by employing the Microtox acute toxicity test and comparing that to the influent.

  11. The oxidation of 2,6-di-tert-butyl-4-methylphenol

    USGS Publications Warehouse

    Yohe, G.R.; Dunbar, J.E.; Pedrotti, R.L.; Scheidt, F.M.; Lee, F.G.H.; Smith, E.C.

    1956-01-01

    The products formed in the oxidation of 2,6-di-tert-butyl-4-methylphenol with oxygen and sodium hydroxide at about 100?? are 3,5-di-tert-butyl-4-hydroxybenzaldehyde, trimethylacetic acid, an acidic compound C14H22O3, and probably 2,6-di-tert-butylbenzoquinone (which was actually isolated in the similar oxidation of the above-named benzaldehyde), in addition to compounds previously reported. Some of the properties of C14H22O3 are given, and the oxidation of it to 2,3-di-tert-butylsuccinic anhydride is described, but assignment of structure is reserved pending the completion of more experimental work.

  12. Bio-Source of di-n-butyl phthalate production by filamentous fungi

    NASA Astrophysics Data System (ADS)

    Tian, Congkui; Ni, Jinren; Chang, Fang; Liu, Sitong; Xu, Nan; Sun, Weiling; Xie, Yuan; Guo, Yongzhao; Ma, Yanrong; Yang, Zhenxing; Dang, Chenyuan; Huang, Yuefei; Tian, Zhexian; Wang, Yiping

    2016-02-01

    Although DBP (di-n-butyl phthalate) is commonly encountered as an artificially-synthesized plasticizer with potential to impair fertility, we confirm that it can also be biosynthesized as microbial secondary metabolites from naturally occurring filamentous fungi strains cultured either in an artificial medium or natural water. Using the excreted crude enzyme from the fungi for catalyzing a variety of substrates, we found that the fungal generation of DBP was largely through shikimic acid pathway, which was assembled by phthalic acid with butyl alcohol through esterification. The DBP production ability of the fungi was primarily influenced by fungal spore density and incubation temperature. This study indicates an important alternative natural waterborne source of DBP in addition to artificial synthesis, which implied fungal contribution must be highlighted for future source control and risk management of DBP.

  13. Bio-Source of di-n-butyl phthalate production by filamentous fungi.

    PubMed

    Tian, Congkui; Ni, Jinren; Chang, Fang; Liu, Sitong; Xu, Nan; Sun, Weiling; Xie, Yuan; Guo, Yongzhao; Ma, Yanrong; Yang, Zhenxing; Dang, Chenyuan; Huang, Yuefei; Tian, Zhexian; Wang, Yiping

    2016-01-01

    Although DBP (di-n-butyl phthalate) is commonly encountered as an artificially-synthesized plasticizer with potential to impair fertility, we confirm that it can also be biosynthesized as microbial secondary metabolites from naturally occurring filamentous fungi strains cultured either in an artificial medium or natural water. Using the excreted crude enzyme from the fungi for catalyzing a variety of substrates, we found that the fungal generation of DBP was largely through shikimic acid pathway, which was assembled by phthalic acid with butyl alcohol through esterification. The DBP production ability of the fungi was primarily influenced by fungal spore density and incubation temperature. This study indicates an important alternative natural waterborne source of DBP in addition to artificial synthesis, which implied fungal contribution must be highlighted for future source control and risk management of DBP. PMID:26857605

  14. Bio-Source of di-n-butyl phthalate production by filamentous fungi

    PubMed Central

    Tian, Congkui; Ni, Jinren; Chang, Fang; Liu, Sitong; Xu, Nan; Sun, Weiling; Xie, Yuan; Guo, Yongzhao; Ma, Yanrong; Yang, Zhenxing; Dang, Chenyuan; Huang, Yuefei; Tian, Zhexian; Wang, Yiping

    2016-01-01

    Although DBP (di-n-butyl phthalate) is commonly encountered as an artificially-synthesized plasticizer with potential to impair fertility, we confirm that it can also be biosynthesized as microbial secondary metabolites from naturally occurring filamentous fungi strains cultured either in an artificial medium or natural water. Using the excreted crude enzyme from the fungi for catalyzing a variety of substrates, we found that the fungal generation of DBP was largely through shikimic acid pathway, which was assembled by phthalic acid with butyl alcohol through esterification. The DBP production ability of the fungi was primarily influenced by fungal spore density and incubation temperature. This study indicates an important alternative natural waterborne source of DBP in addition to artificial synthesis, which implied fungal contribution must be highlighted for future source control and risk management of DBP. PMID:26857605

  15. Emulsion Polymerization of Butyl Acrylate: Spin Trapping and EPR Study

    NASA Technical Reports Server (NTRS)

    Kim, S.; Westmoreland, D.

    1994-01-01

    The propagating radical in the emulsion polymerization reaction of butyl acrylate was detected by Electron Paramagnetic Resonance spectroscopy using two spin trapping agents, 2-methyl-2nitrosopropane and alpha -N-tert-butylnitrone.

  16. 21 CFR 172.270 - Sulfated butyl oleate.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... transesterification of an edible vegetable oil using 1-butanol. Following sulfation, the reaction mixture is washed... oleate reaction mixture meets the following specifications: (1) Not less than 90 percent butyl oleate....

  17. 21 CFR 172.270 - Sulfated butyl oleate.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... edible vegetable oil using 1-butanol. Following sulfation, the reaction mixture is washed with water and neutralized with aqueous sodium or potassium hydroxide. Prior to sulfation, the butyl oleate reaction...

  18. Quantification of hypoglycin A as butyl ester.

    PubMed

    Sander, Johannes; Terhardt, Michael; Sander, Stefanie; Janzen, Nils

    2016-09-01

    L-α-amino-methylenecyclopropyl propionic acid (Hypoglycin A, HGA) has been found to be the toxic compound in fruits of the Sapindaceae family causing acute intoxication when ingested as food or feed. Clinical symptoms are consistent with acquired multiple acyl-CoA dehydrogenase deficiency (MADD). Ultra performance liquid chromatography-tandem mass spectrometry was used to measure HGA after butylation. Sample volumes were 10μL for serum and 20μL for urine. Internal standard for HGA was d3-leucine, samples were plotted on a 7-point linear calibration curve. Coefficients of variation were <15% at 0.01μmol HGA/L and ≤4.1% at 10μmol/L. R(2) values for linearity were ≥0.995. In order to quantify non-metabolized HGA together with some of its metabolites plus a spectrum of acyl glycines and acyl carnitines typical for acquired MADD in one single analysis HGA measurement was integrated into a method which we previously developed for metabolites of HGA and acyl conjugates. The new method is suitable for biochemical diagnosis of Ackee fruit poisoning or atypical myopathy in horses and for forensic purposes in cases of suspected HGA poisoning. PMID:27433981

  19. Quantification of hypoglycin A as butyl ester.

    PubMed

    Sander, Johannes; Terhardt, Michael; Sander, Stefanie; Janzen, Nils

    2016-09-01

    L-α-amino-methylenecyclopropyl propionic acid (Hypoglycin A, HGA) has been found to be the toxic compound in fruits of the Sapindaceae family causing acute intoxication when ingested as food or feed. Clinical symptoms are consistent with acquired multiple acyl-CoA dehydrogenase deficiency (MADD). Ultra performance liquid chromatography-tandem mass spectrometry was used to measure HGA after butylation. Sample volumes were 10μL for serum and 20μL for urine. Internal standard for HGA was d3-leucine, samples were plotted on a 7-point linear calibration curve. Coefficients of variation were <15% at 0.01μmol HGA/L and ≤4.1% at 10μmol/L. R(2) values for linearity were ≥0.995. In order to quantify non-metabolized HGA together with some of its metabolites plus a spectrum of acyl glycines and acyl carnitines typical for acquired MADD in one single analysis HGA measurement was integrated into a method which we previously developed for metabolites of HGA and acyl conjugates. The new method is suitable for biochemical diagnosis of Ackee fruit poisoning or atypical myopathy in horses and for forensic purposes in cases of suspected HGA poisoning.

  20. Radiation degradation of spent butyl rubbers

    NASA Astrophysics Data System (ADS)

    Telnov, A. V.; Zavyalov, N. V.; Khokhlov, Yu. A.; Sitnikov, N. P.; Smetanin, M. L.; Tarantasov, V. P.; Shadrin, D. N.; Shorikov, I. V.; Liakumovich, A. L.; Miryasova, F. K.

    2002-03-01

    Radiation methods of materials modification applied in technological chains can have significant economical and ecological advantages as compared to the established chemical, thermal and mechanical methods. Each year the problems of nature resources economy through the use of production and consumption wastes acquire a more significant value, as it allows to solve also ecological issues along with economical ones. This is mostly acute in relation to polymeric systems based on saturated rubbers, for example butyl rubber (BR) used in the tyre industry, as due to their high resistance to the action of oxygen, ozone, solar radiation and bacteria, they contaminate the environment for rather a long period. At VNIIEF and KSPU experiments were carried out on application of electron beams with energy from 6 to 10 MeV for radiation destruction of spent rubber based on BR. The radiation-degraded material was tested for re-use in the formulation of initial diaphragm mixture, rubber mixture for producing rubberized fabric and roofing.

  1. Embryolethality of butyl benzyl phthalate in rats

    SciTech Connect

    Ema, N.; Itami, T.; Kawasaki, H. )

    1991-03-15

    The developmental toxicity of butyl benzyl phthalate (BBP) was studied in Wistar rats. Pregnant rats were given BBP at a dosage of 0, 0.25, 0.5, 1.0 or 2.0% in the diet from day 0 to day 20 of pregnancy. Morphological examinations of the fetuses revealed no evidence of teratogenesis. In the 2.0% group, all dams exhibited complete resorption of all the implanted embryos, and their food consumption, body weight gain and adjusted weight gain during pregnancy were markedly lowered. To determine whether the embryolethality was the result of reduced food consumption during pregnancy, a pair-feeding study was performed in which the pregnant rats received the same amount of diet consumed by the 2.0% BBP-treated pregnant rats. The pair-fed and 2.0 % BBP-treated pregnant rats showed significant and comparable reductions in the adjusted weight gain. The number of live fetuses was lowered in the pair-fed group. However, the complete resorption of all the implanted embryos was not found in any of the pair-fed pregnant rats. The data suggest that the embryolethality observed in the 2.0 % BBP-treated pregnant rats is attributable to the effects o dietary BBP.

  2. Enhancement of ethylenethiourea recoveries in food analyses by addition of cysteine hydrochloride.

    PubMed

    Sack, C A

    1995-01-01

    The effectiveness of cysteine hydrochloride (Cys-HCl) as a preservative of ethylenethiourea (ETU) in product matrixes and during analysis was studied. ETU recoveries were adversely affected by certain product matrixes when fortified directly into the product. Recoveries in 8 selected food items were 0-92% when analyzed 30 min after fortification and 0-51% when analyzed after 24 h. When Cys-HCl was added to product prior to fortification, recoveries increased to 71-95% even after frozen storage for 2-4 weeks. Cys-HCl was added during analysis of 53 untreated items. Recoveries improved an average of 15% with Cys-HCl. Without Cys-HCl, recoveries were erratic (20-98%), but with Cys-HCl, recoveries were 68-113%. Other antioxidants (sodium sulfite, butylated hydroxyanisole, butylated hydroxytoluene, and vitamins A and C) also were evaluated as ETU preservatives. When lettuce was treated first with sodium sulfite and then fortified with ETU, recoveries averaged 86%; without sodium sulfite, they averaged 1%. The other antioxidants were less effective for preserving ETU in lettuce, giving only 8-46% recoveries. The effect of oxidizers (potassium bromate, sodium hypochlorite, and hydrogen peroxide) on ETU recovery was also determined. Recovery of ETU from a baby food product (pears and pineapple) was 82%; with oxidizers, recoveries were 0-8%.

  3. Degradation mechanism of t-butyl methyl ether (MTBE) in atmospheric droplets.

    PubMed

    Guillard, Chantal; Charton, Nathalie; Pichat, Pierre

    2003-11-01

    The aim of this study was to obtain information about the degradation of t-butyl methyl ether (MTBE; (CH(3))(3)C-O-CH(3)) in atmospheric water droplets (rain, clouds, fog). These water droplets contain hydrogen peroxide and iron ions, which are a source of the powerful oxidising radical OH degrees, particularly under solar irradiation (photo-Fenton reaction). MTBE was chosen for this work because of its current use as an oxygenated additive in gasoline. In this study we found that MTBE is not stable in the atmosphere. More than 15 intermediate products were identified, five of which were quantified (t-butyl formate (TBF), methyl acetate (MA), t-butyl alcohol (TBA), acetone (AC), formaldehyde). The evaluation of the disappearance kinetic of the main intermediate compounds shows the following activity pattern k((TBA))>k((MTBE))>k((TBF)),k>((AC)). Acetone was found to be about 15 times more stable than MTBE in atmospheric conditions. The degradation pathways are discussed on the basis of these identifications and on the degradation of the main intermediate products in similar conditions to MTBE.

  4. n-Butyl cyanoacrylate synthesis. A new quality step using microwaves.

    PubMed

    Carriles, Yaquelin Ramos; Brito, Rubén Alvarez; Sánchez, Ricardo Martínez; Acevedo, Elayma Sánchez; Domínguez, Paola Rodríguez; Mueller, Wolf-Dieter

    2014-05-15

    Alkyl cyanoacrylates are interesting products for use in industry because of their properties enabling them to stick together a wide range of substrates. n-Butyl cyanoacrylate is one of the most successfully used tissue adhesives in the field of medicine because it exhibits bacteriostatic and haemostatic characteristics, in addition to its adhesive properties. At present, its synthesis is performed with good yields via Knoevenagel condensation using conventional sources of heating, but this requires a long processing time. The aim of this work was to look for a new way of synthesising n-butyl cyanoacrylate using microwave irradiation as the source of heating. This non-conventional source of heating most likely reduces the process time of the synthesis. In comparison with a conventional heating source, such as an oil bath, the results showed the advantages of this method whereby the n-butyl cyanoacrylate gave the same yield and quality with a reduction in the reaction time by a factor of 3-5-fold.

  5. Protective effect of butylated hydroxylanisole against hydrogen peroxide-induced apoptosis in primary cultured mouse hepatocytes

    PubMed Central

    Hwang, Geun Hye; Jeon, Yu Jin; Han, Ho Jae; Park, Soo Hyun; Baek, Kyoung Min; Chang, Woochul; Kim, Joong Sun; Kim, Lark Kyun; Lee, You-Mie; Lee, Sangkyu; Bae, Jong-Sup; Jee, Jun-Goo

    2015-01-01

    Butylated hydroxyanisole (BHA) is a synthetic phenolic compound consisting of a mixture of two isomeric organic compounds: 2-tert-butyl-4-hydroxyanisole and 3-tert-butyl-4-hydroxyanisole. We examined the effect of BHA against hydrogen peroxide (H2O2)-induced apoptosis in primary cultured mouse hepatocytes. Cell viability was significantly decreased by H2O2 in a dose-dependent manner. Additionally, H2O2 treatment increased Bax, decreased Bcl-2, and promoted PARP-1 cleavage in a dose-dependent manner. Pretreatment with BHA before exposure to H2O2 significantly attenuated the H2O2-induced decrease of cell viability. H2O2 exposure resulted in an increase of intracellular reactive oxygen species (ROS) generation that was significantly inhibited by pretreatment with BHA or N-acetyl-cysteine (NAC, an ROS scavenger). H2O2-induced decrease of cell viability was also attenuated by pretreatment with BHA and NAC. Furthermore, H2O2-induced increase of Bax, decrease of Bcl-2, and PARP-1 cleavage was also inhibited by BHA. Taken together, results of this investigation demonstrated that BHA protects primary cultured mouse hepatocytes against H2O2-induced apoptosis by inhibiting ROS generation. PMID:25798044

  6. Attenuation of methyl tert-butyl ether in water using sunlight and a photocatalyst.

    PubMed

    Sahle-Demessie, E; Enriquez, J; Gupta, G

    2002-01-01

    The use of methyl tert-butyl ether (MTBE) as a gasoline additive has resulted in increasing pollution of groundwater. Most of the conventional treatment technologies are inefficient or costly when the initial concentration of MTBE is low (< 200 microg/L). To find an ecology friendly and inexpensive method for MTBE remediation, we used solar radiation with titanium dioxide (TiO2) as a photocatalyst. For synthetic samples, almost complete degradation (99+%) of MTBE was observed at the end of 5-hour test run with 0.05 g/L of slurry TiO2. Intermediate products detected were tertiary butyl formate, tertiary butyl alcohol, and trace amounts of acetone. Studies conducted using contaminated groundwater samples with TiO2 and sunlight showed that aromatic organic species benzene, toluene, ethylbenzene, and xylenes (BTEX) were degraded up to a factor of 10 times faster than MTBE. However, dissolved metals (Fe2+) and chloride ions in contaminated waters decreased the photo-activity of TiO2 for the degradation of MTBE. Reducing the pH of the groundwater samples increased the MTBE degradation rate threefold. Photocatalysis accelerates the solar degradation of MTBE and reduces its half-life by more than 3 orders of magnitude. The study indicated that solar degradation is a low-cost and effective alternative to attenuate MTBE in drinking water supplies.

  7. 75 FR 31749 - International Standard-Setting Activities

    Federal Register 2010, 2011, 2012, 2013, 2014

    2010-06-04

    ... President, pursuant to Proclamation No. 6780 of March 23, 1995 (60 FR 15845), designated the U.S. Department... antioxidants (butylated hydroxyanisole, butylated hydroxytoluene, propyl gallate, and...

  8. Isotope effects and the temperature dependences of the hyperfine coupling constants of muoniated sec-butyl radicals in condensed phases.

    PubMed

    Fleming, Donald G; Bridges, Michael D; Arseneau, Donald J; Chen, Ya Kun; Wang, Yan Alexander

    2011-04-01

    Reported here is the first μSR study of the muon (A(μ)) and proton (A(p)) β-hyperfine coupling constants (Hfcc) of muoniated sec-butyl radicals, formed by muonium (Mu) addition to 1-butene and to cis- and trans-2-butene. The data are compared with in vacuo spin-unrestricted MP2 and hybrid DFT/B3YLP calculations reported in the previous paper (I), which played an important part in the interpretation of the data. The T-dependences of both the (reduced) muon, A(μ)′(T), and proton, A(p)(T), Hfcc are surprisingly well explained by a simple model, in which the calculated Hfcc from paper I at energy minima of 0 and near ±120° are thermally averaged, assuming an energy dependence given by a basic 2-fold torsional potential. Fitted torsional barriers to A(μ)′(T) from this model are similar (~3 kJ/mol) for all muoniated butyl radicals, suggesting that these are dominated by ZPE effects arising from the C−Mu bond, but for A(p)(T) exhibit wide variations depending on environment. For the cis- and trans-2-butyl radicals formed from 2-butene, A(μ)′(T) exhibits clear discontinuities at bulk butene melting points, evidence for molecular interactions enhancing these muon Hfcc in the environment of the solid state, similar to that found in earlier reports for muoniated tert-butyl. In contrast, for Mu−sec-butyl formed from 1-butene, there is no such discontinuity. The muon hfcc for the trans-2-butyl radical are seemingly very well predicted by B3LYP calculations in the solid phase, but for sec-butyl from 1-butene, showing the absence of further interactions, much better agreement is found with the MP2 calculations across the whole temperature range. Examples of large proton Hfcc near 0 K are also reported, due to eclipsed C−H bonds, in like manner to C−Mu, which then also exhibit clear discontinuities in A(p)(T) at bulk melting points. The data suggest that the good agreement found between theory and experiment from the B3LYP calculations for eclipsed bonds in

  9. Decreased toxicity to terrestrial plants associated with a mixture of methyl tert-butyl ether and its metabolite tert-butyl alcohol.

    PubMed

    An, Youn-Joo; Lee, Woo-Mi

    2007-08-01

    The influence of the main fuel oxygenate methyl tert-butyl ether (MTBE) and its key metabolite, tert-butyl alcohol (TBA), on the growth of a plant seedling was studied separately and in combination. The test plants were mung bean (Phaseolus radiatus), cucumber (Cucumis sativus), wheat (Triticum aestivum), sorghum (Sorghum bicolor), kale (Brassica alboglabra), Chinese cabbage (Brassica campestris), and sweet corn (Zea mays). The growth of all the plants was adversely affected by TBA and MTBE. The 5-d median effective concentration (EC50) for the plants exposed to MTBE and TBA were in the range of 680 to 1,000 mg MTBE/kg soil (dry wt) and 1,200 to 3,500 mg TBA/kg soil (dry wt), respectively. The relative order of the sensitivity rankings is almost the same for MTBE and TBA. Methyl tert-butyl ether is more toxic than TBA to most of the test species. Based on the EC50 values, MTBE is approximately 1.5 to 3 times more potent than TBA. The sum of the toxic unit (TU) at 50% inhibition of the mixture (EC50mix) was calculated from the dose (TU-based)-response relationships using the trimmed Spearman-Karber method. The combined effect of MTBE + TBA on the plant growth was less than additive because the EC50mix values were greater than I TU. This phenomenon may be due to the competition of MTBE and TBA in terms of their intake by plants. The combined effects of MTBE and TBA should be taken into account to assess their risk in gasoline-contaminated sites.

  10. Microbial degradation of methyl tert-butyl ether and tert-butyl alcohol in the subsurface.

    PubMed

    Schmidt, Torsten C; Schirmer, Mario; Weiss, Holger; Haderlein, Stefan B

    2004-06-01

    The fate of fuel oxygenates such as methyl tert-butyl ether (MTBE) in the subsurface is governed by their degradability under various redox conditions. The key intermediate in degradation of MTBE and ethyl tert-butyl ether (ETBE) is tert-butyl alcohol (TBA) which was often found as accumulating intermediate or dead-end product in lab studies using microcosms or isolated cell suspensions. This review discusses in detail the thermodynamics of the degradation processes utilizing various terminal electron acceptors, and the aerobic degradation pathways of MTBE and TBA. It summarizes the present knowledge on MTBE and TBA degradation gained from either microcosm or pure culture studies and emphasizes the potential of compound-specific isotope analysis (CSIA) for identification and quantification of degradation processes of slowly biodegradable pollutants such as MTBE and TBA. Microcosm studies demonstrated that MTBE and TBA may be biodegradable under oxic and nearly all anoxic conditions, although results of various studies are often contradictory, which suggests that site-specific conditions are important parameters. So far, TBA degradation has not been shown under methanogenic conditions and it is currently widely accepted that TBA is a recalcitrant dead-end product of MTBE under these conditions. Reliable in situ degradation rates for MTBE and TBA under various geochemical conditions are not yet available. Furthermore, degradation pathways under anoxic conditions have not yet been elucidated. All pure cultures capable of MTBE or TBA degradation isolated so far use oxygen as terminal electron acceptor. In general, compared with hydrocarbons present in gasoline, fuel oxygenates biodegrade much slower, if at all. The presence of MTBE and related compounds in groundwater therefore frequently limits the use of in situ biodegradation as remediation option at gasoline-contaminated sites. Though degradation of MTBE and TBA in field studies has been reported under oxic

  11. Conversion of Lignocellulosic Biomass to Ethanol and Butyl Acrylate

    SciTech Connect

    Binder, Thomas; Erpelding, Michael; Schmid, Josef; Chin, Andrew; Sammons, Rhea; Rockafellow, Erin

    2015-04-10

    Conversion of Lignocellulosic Biomass to Ethanol and Butyl Acrylate. The purpose of Archer Daniels Midlands Integrated Biorefinery (IBR) was to demonstrate a modified acetosolv process on corn stover. It would show the fractionation of crop residue to distinct fractions of cellulose, hemicellulose, and lignin. The cellulose and hemicellulose fractions would be further converted to ethanol as the primary product and a fraction of the sugars would be catalytically converted to acrylic acid, with butyl acrylate the final product. These primary steps have been demonstrated.

  12. Effect of thyme/cumin essential oils and butylated hydroxyl anisole/butylated hydroxyl toluene on physicochemical properties and oxidative/microbial stability of chicken patties.

    PubMed

    Sariçoban, Cemalettin; Yilmaz, Mustafa Tahsin

    2014-02-01

    In this study, effects of thyme/cumin essential oils (EO) and butylated hydroxyl anisole (BHA)/butylated hydroxyl toluene (BHT) on physicochemical properties and storage stability of chicken patties were compared in different storage periods (0, 3, 7, 14, 21, and 28 d). It was found that there were significant (P < 0.05) differences between physicochemical properties of patty samples treated with EO and the synthetic antioxidants. The EO showed similar performance to those of BHA and BHT in limiting TBARS values of chicken patty samples. Similarity in performance was also the case for microbial stability (total aerobic mesophilic, psychrotrophic, lactic acid, and coliform bacteria as well as molds and yeasts); namely, their effects were significant (P < 0.05). Effect of thyme EO was significant (P < 0.05) and remarkable, not allowing any coliform bacteria to grow in the samples. Given that EO were obtained from natural sources, the data suggested that the EO might be more useful than their synthetic counterparts, BHA and BHT, as additives for chicken patties to maintain oxidative/microbial stability and increase shelf life.

  13. 40 CFR 180.576 - Cyhalofop-butyl; tolerances for residues.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... of cyhalofop-butyl, including its metabolites and degradates, in or on the commodities listed in the... cyhalofop butyl , cyhalofop acid , and the di-acid metabolite . Commodity Parts per million Rice, grain...

  14. 40 CFR 180.576 - Cyhalofop-butyl; tolerances for residues.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... of cyhalofop-butyl, including its metabolites and degradates, in or on the commodities listed in the... cyhalofop butyl , cyhalofop acid , and the di-acid metabolite . Commodity Parts per million Rice, grain...

  15. 40 CFR 180.576 - Cyhalofop-butyl; tolerances for residues.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... of cyhalofop-butyl, including its metabolites and degradates, in or on the commodities listed in the... cyhalofop butyl , cyhalofop acid , and the di-acid metabolite . Commodity Parts per million Rice, grain...

  16. Recycling of gamma irradiated inner tubes in butyl based rubber compounds

    NASA Astrophysics Data System (ADS)

    Karaağaç, Bağdagül; Şen, Murat; Deniz, Veli; Güven, Olgun

    2007-12-01

    Recycling of gamma irradiated inner tubes made of butyl rubber in butyl based rubber compounds was studied. Gamma irradiated inner tube wastes and commercial butyl rubber crumbs devulcanized by conventional methods were replaced with butyl rubber up to 15 phr in the compound recipe. The rheological and mechanical properties and carbon black dispersion degree for both types of compounds were measured and then compared to those of virgin butyl rubber compound. It is well known that mechanical properties are deteriorated when rubber crumb is added to the virgin compound. The deterioration in the mechanical properties for the compounds prepared by recycling of irradiated inner tubes at 120 kGy is much lower than the compounds prepared by using commercial butyl crumbs. It has been observed that gamma irradiated used inner tubes were compatible with butyl rubber and could be recycled within butyl based rubber compounds.

  17. 27 CFR 21.100 - n-Butyl alcohol.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2014-04-01 2014-04-01 false n-Butyl alcohol. 21.100 Section 21.100 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY ALCOHOL FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants §...

  18. 27 CFR 21.101 - tert-Butyl alcohol.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2011-04-01 2011-04-01 false tert-Butyl alcohol. 21.101 Section 21.101 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY LIQUORS FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants §...

  19. 27 CFR 21.100 - n-Butyl alcohol.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2010-04-01 2010-04-01 false n-Butyl alcohol. 21.100 Section 21.100 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY LIQUORS FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants §...

  20. 27 CFR 21.101 - tert-Butyl alcohol.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2013-04-01 2013-04-01 false tert-Butyl alcohol. 21.101 Section 21.101 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY ALCOHOL FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants §...

  1. 27 CFR 21.101 - tert-Butyl alcohol.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2014-04-01 2014-04-01 false tert-Butyl alcohol. 21.101 Section 21.101 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY ALCOHOL FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants §...

  2. 27 CFR 21.101 - tert-Butyl alcohol.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2012-04-01 2012-04-01 false tert-Butyl alcohol. 21.101 Section 21.101 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY LIQUORS FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants §...

  3. 27 CFR 21.101 - tert-Butyl alcohol.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2010-04-01 2010-04-01 false tert-Butyl alcohol. 21.101 Section 21.101 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY LIQUORS FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants §...

  4. 27 CFR 21.100 - n-Butyl alcohol.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2011-04-01 2011-04-01 false n-Butyl alcohol. 21.100 Section 21.100 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY LIQUORS FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants §...

  5. 27 CFR 21.100 - n-Butyl alcohol.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2013-04-01 2013-04-01 false n-Butyl alcohol. 21.100 Section 21.100 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY ALCOHOL FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants §...

  6. 27 CFR 21.100 - n-Butyl alcohol.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 27 Alcohol, Tobacco Products and Firearms 1 2012-04-01 2012-04-01 false n-Butyl alcohol. 21.100 Section 21.100 Alcohol, Tobacco Products and Firearms ALCOHOL AND TOBACCO TAX AND TRADE BUREAU, DEPARTMENT OF THE TREASURY LIQUORS FORMULAS FOR DENATURED ALCOHOL AND RUM Specifications for Denaturants §...

  7. Distribution of methyl tert-butyl ether (MTBE) and selected water-quality constituents in the surficial aquifer at the Dover National Test Site, Dover Air Force Base, Delaware, 2001

    USGS Publications Warehouse

    Stewart, Marie; Guertal, William R.; Barbaro, Jeffrey R.; McHale, Timothy J.

    2004-01-01

    A joint study by the Dover National Test Site, Dover Air Force Base, Delaware, and the U.S. Geological Survey was conducted from June 27 through July 18, 2001, to determine the spatial distribution of the gasoline oxygenate additive methyl tert-butyl ether and selected water-quality constituents in the surficial aquifer underlying the Dover National Test Site. This report provides a summary assessment of the distribution of methyl tert-butyl ether and a preliminary screening of selected constituents that may affect natural attenuation and remediation demonstrations at the Dover National Test Site. The information gathered during this study is designed to assist potential remedial investigators who are considering conducting a methyl tert-butyl ether remedial demonstration at the test site. In addition, the study supported a planned enhanced bioremediation demonstration and assisted the Dover National Test Site in identifying possible locations for future methyl tert-butyl ether remediation demonstrations. A direct-push drill rig was used to collect a total of 147 ground-water samples (115 VOC samples and 32 quality-assurance samples) at varying depths. Volatile organic compounds were above the method reporting limits in 59 of the 115 ground-water samples. The concentrations ranged from below detection limits to maximum values of 12.4 micrograms per liter of cis-1,2-dichloro-ethene, 1.14 micrograms per liter of trichloro-ethene, 2.65 micrograms per liter of tetrachloro-ethene, 1,070 micrograms per liter of methyl tert-butyl ether, 4.36 micrograms per liter of benzene, and 1.8 micrograms per liter of toluene. Vinyl chloride, ethylbenzene, p,m-xylene, and o-xylene were not detected in any of the samples collected during this investigation. Methyl tert-butyl ether was detected in 47 of the 115 ground-water samples. The highest concentrations of methyl tert-butyl ether were detected in the surficial aquifer from ?4.6 to 6.4 feet mean sea level; however, methyl tert-butyl

  8. Forensic analysis of tertiary-butyl alcohol (TBA) detections in a hydrocarbon-rich groundwater basin.

    PubMed

    Quast, Konrad W; Levine, Audrey D; Kester, Janet E; Fordham, Carolyn L

    2016-04-01

    Tertiary-butyl alcohol (TBA), a high-production volume (HPV) chemical, was sporadically detected in groundwater and coalbed methane (CBM) wells in southeastern Colorado's hydrocarbon-rich Raton Basin. TBA concentrations in shallow water wells averaged 75.1 μg/L, while detections in deeper CBM wells averaged 14.4 μg/L. The detection of TBA prompted a forensic investigation to try to identify potential sources. Historic and recent data were reviewed to determine if there was a discernable pattern of TBA occurrence. Supplemental samples from domestic water wells, monitor wells, CBM wells, surface waters, and hydraulic fracturing (HF) fluids were analyzed for TBA in conjunction with methyl tertiary-butyl ether (MTBE) and ethyl tertiary-butyl ether (ETBE), proxies for evidence of contamination from reformulated gasoline or associated oxygenates. Exploratory microbiological sampling was conducted to determine if methanotrophic organisms co-occurred with TBA in individual wells. Meaningful comparisons of historic TBA data were limited due to widely varying reporting limits. Mapping of TBA occurrence did not reveal any spatial patterns or physical associations with CBM operations or contamination plumes. Additionally, TBA was not detected in HF fluids or surface water samples. Given the widespread use of TBA in industrial and consumer products, including water well completion materials, it is likely that multiple diffuse sources exist. Exploratory data on stable isotopes, dissolved gases, and microbial profiling provide preliminary evidence that methanotrophic activity may be producing TBA from naturally occurring isobutane. Reported TBA concentrations were significantly below a conservative risk-based drinking water screening level of 8000 μg/L derived from animal toxicity data. PMID:26946495

  9. Forensic analysis of tertiary-butyl alcohol (TBA) detections in a hydrocarbon-rich groundwater basin.

    PubMed

    Quast, Konrad W; Levine, Audrey D; Kester, Janet E; Fordham, Carolyn L

    2016-04-01

    Tertiary-butyl alcohol (TBA), a high-production volume (HPV) chemical, was sporadically detected in groundwater and coalbed methane (CBM) wells in southeastern Colorado's hydrocarbon-rich Raton Basin. TBA concentrations in shallow water wells averaged 75.1 μg/L, while detections in deeper CBM wells averaged 14.4 μg/L. The detection of TBA prompted a forensic investigation to try to identify potential sources. Historic and recent data were reviewed to determine if there was a discernable pattern of TBA occurrence. Supplemental samples from domestic water wells, monitor wells, CBM wells, surface waters, and hydraulic fracturing (HF) fluids were analyzed for TBA in conjunction with methyl tertiary-butyl ether (MTBE) and ethyl tertiary-butyl ether (ETBE), proxies for evidence of contamination from reformulated gasoline or associated oxygenates. Exploratory microbiological sampling was conducted to determine if methanotrophic organisms co-occurred with TBA in individual wells. Meaningful comparisons of historic TBA data were limited due to widely varying reporting limits. Mapping of TBA occurrence did not reveal any spatial patterns or physical associations with CBM operations or contamination plumes. Additionally, TBA was not detected in HF fluids or surface water samples. Given the widespread use of TBA in industrial and consumer products, including water well completion materials, it is likely that multiple diffuse sources exist. Exploratory data on stable isotopes, dissolved gases, and microbial profiling provide preliminary evidence that methanotrophic activity may be producing TBA from naturally occurring isobutane. Reported TBA concentrations were significantly below a conservative risk-based drinking water screening level of 8000 μg/L derived from animal toxicity data.

  10. CONCENTRATIONS, SOURCES, AND FATE OF THE GASOLINE OXYGENATE METHYL TERT-BUTYL ETHER (MTBE) IN A MULTIPLE-USE LAKE. (R826282)

    EPA Science Inventory

    Discovery of the fuel additive methyl tert-butyl ether (MTBE) in
    drinking water supplies is of concern to public health officials, water
    suppliers, and the public. Despite recent policy decisions, few published
    studies exist on the concentrations, sources, a...

  11. Room Temperature Aging Study of Butyl O-rings

    SciTech Connect

    Mark Wilson

    2009-08-07

    During testing under the Enhanced Surveillance Campaign in 2001, preliminary data detected a previously unknown and potentially serious concern with recently procured butyl o-rings. All butyl o-rings molded from a proprietary formulation throughout the period circa 1999 through 2001 had less than a full cure. Tests showed that sealing force values for these suspect o-rings were much lower than expected and their physical properties were very sensitive to further post curing at elevated temperatures. Further testing confirmed that these o-rings were approximately 50% cured versus the typical industry standard of > 90% cured. Despite this condition, all suspect o-rings fully conformed to their QC acceptance requirements, including their individual product drawing requirements.

  12. Biodegradation of Methyl tert-Butyl Ether by Co-Metabolism with a Pseudomonas sp. Strain.

    PubMed

    Li, Shanshan; Wang, Shan; Yan, Wei

    2016-01-01

    Co-metabolic bioremediation is supposed to be an impressive and promising approach in the elimination technology of methyl tert-butyl ether (MTBE), which was found to be a common pollutant worldwide in the ground or underground water in recent years. In this paper, bacterial strain DZ13 (which can co-metabolically degrade MTBE) was isolated and named as Pseudomonas sp. DZ13 based on the result of 16S rRNA gene sequencing analysis. Strain DZ13 could grow on n-alkanes (C₅-C₈), accompanied with the co-metabolic degradation of MTBE. Diverse n-alkanes with different carbon number showed a significant influence on the degradation rate of MTBE and accumulation of tert-butyl alcohol (TBA). When Pseudomonas sp. DZ13 co-metabolically degraded MTBE with n-pentane as the growth substrate, a higher MTBE-degrading rate (Vmax = 38.1 nmol/min/mgprotein, Ks = 6.8 mmol/L) and lower TBA-accumulation was observed. In the continuous degradation experiment, the removal efficiency of MTBE by Pseudomonas sp. Strain DZ13 did not show an obvious decrease after five times of continuous addition. PMID:27608032

  13. Biodegradation of Methyl tert-Butyl Ether by Co-Metabolism with a Pseudomonas sp. Strain

    PubMed Central

    Li, Shanshan; Wang, Shan; Yan, Wei

    2016-01-01

    Co-metabolic bioremediation is supposed to be an impressive and promising approach in the elimination technology of methyl tert-butyl ether (MTBE), which was found to be a common pollutant worldwide in the ground or underground water in recent years. In this paper, bacterial strain DZ13 (which can co-metabolically degrade MTBE) was isolated and named as Pseudomonas sp. DZ13 based on the result of 16S rRNA gene sequencing analysis. Strain DZ13 could grow on n-alkanes (C5-C8), accompanied with the co-metabolic degradation of MTBE. Diverse n-alkanes with different carbon number showed a significant influence on the degradation rate of MTBE and accumulation of tert-butyl alcohol (TBA). When Pseudomonas sp. DZ13 co-metabolically degraded MTBE with n-pentane as the growth substrate, a higher MTBE-degrading rate (Vmax = 38.1 nmol/min/mgprotein, Ks = 6.8 mmol/L) and lower TBA-accumulation was observed. In the continuous degradation experiment, the removal efficiency of MTBE by Pseudomonas sp. Strain DZ13 did not show an obvious decrease after five times of continuous addition. PMID:27608032

  14. n-Butyl cyanoacrylate-induced multiple retinal arteriolar occlusions.

    PubMed

    Naithani, Prashant; Khanduja, Sumeet; Sinha, Subijoy; Khanduja, Neha; Naithani, Preeti

    2013-10-01

    We report a case of multiple retinal arteriolar occlusions due to delayed embolisation of N-butylcyanoacrylate glue, initially injected in the external carotid artery for the management of Carotid body tumour. Ocular massage and anterior chamber paracentesis were unfruitful and patient suffered irreversible visual loss in the affected eye. Embolisation of N-butyl cyanoacrylate glue into the retinal vasculature after intratumoral injection should be kept in mind as a rare but possible complication by radiologists and ophthalmologists.

  15. Optimized butyl butyrate synthesis catalyzed by Thermomyces lanuginosus lipase.

    PubMed

    Martins, Andréa B; Friedrich, John L R; Rodrigues, Rafael C; Garcia-Galan, Cristina; Fernandez-Lafuente, Roberto; Ayub, Marco A Z

    2013-01-01

    Butyl butyrate is an ester present in pineapple flavor, which is very important for the food and beverages industries. In this work, the optimization of the reaction of butyl butyrate synthesis catalyzed by the immobilized lipase Lipozyme TL-IM was performed. n-Hexane was selected as the most appropriate solvent. Other reaction parameters such as temperature, substrate molar ratio, biocatalyst content and added water, and their responses measured as yield, were evaluated using a fractional factorial design, followed by a central composite design (CCD) and response surface methodology. In the fractional design 2(4-1) , the four variables were tested and temperature and biocatalyst content were statistically significant and then used for optimization on CCD. The optimal conditions for butyl butyrate synthesis were found to be 48°C; substrate molar ratio 3:1 (butanol:butyric acid); biocatalyst content of 40% of acid mass. Under these conditions, over 90% of yield was obtained in 2 h. Enzyme reuse was tested by washing the biocatalyst with n-hexane or by direct reuse. The direct reuse produced a rapid decrease on enzyme activity, while washing with n-hexane allowed reusing the enzyme for five reactions cycles keeping approximately 85% of its activity.

  16. HIGH LEVELS OF MONOAROMATIC COMPOUNDS LIMIT THE USE OF SOLID-PHASE MICROEXTRACTION OF METHYL TERTIARY BUTYL ETHER AND TERTIARY BUTYL ALCOHOL

    EPA Science Inventory

    Recently, two papers reported the use of solid-phase microextraction (SPME) with polydimethylsiloxane(PDMS)/Carboxen fibers to determine trace levels of methyl tertiary butyl ether (MTBE) and tertiary butyl alcohol (tBA) in water. Attempts were made to apply this technique to th...

  17. Butyl rubber O-ring seals: Revision of test procedures for stockpile materials

    SciTech Connect

    Domeier, L.A.; Wagter, K.R.

    1996-12-01

    Extensive testing showed little correlation between test slab and O-ring performance. New procedures, comparable to those used with the traditional test slabs, were defined for hardness, compression set, and tensile property testing on sacrificial O-ring specimens. Changes in target performance values were made as needed and were, in one case, tightened to reflect the O-ring performance data. An additional study was carried out on O-ring and slab performance vs cure cycle and showed little sensitivity of material performance to large changes in curing time. Aging and spectra of certain materials indicated that two sets of test slabs from current vendor were accidently made from EPDM rather than butyl rubber. Random testing found no O-rings made from EPDM. As a result, and additional spectroscope test will be added to the product acceptance procedures to verify the type of rubber compound used.

  18. Analysis of Oxygenated Component (butyl Ether) and Egr Effect on a Diesel Engine

    NASA Astrophysics Data System (ADS)

    Choi, Seung-Hun; Oh, Young-Taig

    Potential possibility of the butyl ether (BE, oxygenates of di-ether group) was analyzed as an additives for a naturally aspirated direct injection diesel engine fuel. Engine performance and exhaust emission characteristics were analyzed by applying the commercial diesel fuel and oxygenates additives blended diesel fuels. Smoke emission decreased approximately 26% by applying the blended fuel (diesel fuel 80 vol-% + BE 20vol-%) at the engine speed of 25,000 rpm and with full engine load compared to the diesel fuel. There was none significant difference between the blended fuel and the diesel fuel on the power, torque, and brake specific energy consumption rate of the diesel engine. But, NOx emission from the blended fuel was higher than the commercial diesel fuel. As a counter plan, the EGR method was employed to reduce the NOx. Simultaneous reduction of the smoke and the NOx emission from the diesel engine was achieved by applying the BE blended fuel and the cooled EGR method.

  19. Phytochemical Screening: Antioxidant and Antibacterial Properties of Potamogeton Species in Order to Obtain Valuable Feed Additives.

    PubMed

    Lupoae, Paul; Cristea, Victor; Borda, Daniela; Lupoae, Mariana; Gurau, Gabriela; Dinica, Rodica Mihaela

    2015-01-01

    The alcoholic extracts from three submerged perennial plants Potamogeton crispus L., P. pusillus L. and P. pectinatus L. were analyzed by gas chromatography-mass spectrometry coupled with solid phase microextraction (SPME-GC/MS) and by High Performance Liquid Chromatography (HPLC) and their volatile fingerprint and polyphenols composition was mutually compared. Twenty-nine chemical compounds were detected and identified in ethanolic and methanolic extracts; the highest abundance (over 5%) in descending order, was detected for 9,9-dimethyl-8,10- dioxapentacyclo (5,3,0(2,5) 0(3,5,)0 (3,6) decane (21.65%), phenol 2,6 bis (1,1 dimethyletyl) 4-1-methylpropil (20.8%), pentadecanoic acid (14.3%), 2-(5-chloro-2-Methoxyphenyl) pyrrole (8.66%), propanedioic (malonic) acid 2-(4-methylphenyl) sulfonyl ethylidene (5.77%), 2 hydroxy-3 tert butyl-5-isopropyl-6 methyl phenyl ketone (5.76%). The highest total polyphenols and flavonoids content was found in the methanolic extract of P. crispus (112.5±0.5 mg tannic acid/g dry extract; 64.2±1.2 mg quercitin/g dry extract). Antioxidant activities (2,2-difenil-1-picrilhidrazil, hydrogen peroxide and reducing power assays) of obtained extracts are comparable with the standard compounds, butylated hydroxytoluene, rutin and ascorbic acid. Antibacterial efficiency of methanolic extracts was notably demonstrated against Gram negative (Escherichia coli, Enterobacter hormaechei) and Gram positive bacteria (Enterococcus casseliflavus). The data reported for the first time for Romanian Potamogeton species, provides extensive support for the chemical investigations of these plants of the aquatic anthropogene ecosystems in order to obtain valuable bioadditives for animal feed and/or pharmaceutical/food industry.

  20. Enantioselective degradation and chiral stability of the herbicide fluazifop-butyl in soil and water.

    PubMed

    Qi, Yanli; Liu, Donghui; Luo, Mai; Jing, Xu; Wang, Peng; Zhou, Zhiqiang

    2016-03-01

    The stereoselective degradation and transformation of the enantiomers of the herbicide fluazifop-butyl in soil and water were studied to investigate the environmental behavior and chiral stability of the optical pure product. Its main chiral metabolite fluazifop was also monitored. LC/MS/MS with Chiralpak IC chiral column was used to separate the enantiomers of fluazifop-butyl and fluazifop. Validated enantioselective residue analysis methods were established with recoveries ranging from 77.1 to 115.4% and RSDs from 0.85 to 8.9% for the enantiomers. It was found the dissipation of fluazifop-butyl was rapid in the three studied soils (Beijing, Harbin and Anhui soil), and the degradation half-lives of the enantiomers ranged from 0.136 to 2.7 d. Enantioselective degradations were found in two soils. In Beijing soil, R-fluazifop-butyl was preferentially degraded leading to relative enrichment of S-enantiomer, but in Anhui soil, S-fluazifop-butyl dissipated faster. There was no conversion of the R-fluazifop-butyl into S-fluazifop-butyl or vice versa in the soils. The formation of fluazifop in the soils was rapidly accompanied with the fast degradation of fluazifop-butyl, and the enantioselectivity and the transformation of S-fluazifop to R-fluazifop were found. The degradation of fluazifop-butyl in water was also quick, with half-lives of the enantiomers ranging from 0.34 to 2.52 d, and there was no significant enantioselectivity of the degradation of fluazifop-butyl and the formation of fluazifop. The effects of pH on the degradation showed fluazifop-butyl enantiomers degraded faster in alkaline conditions. This study showed an evidence of enantioselective behavior and enantiomerization of the chiral herbicide fluazifop-butyl.

  1. Enantioselective degradation and chiral stability of the herbicide fluazifop-butyl in soil and water.

    PubMed

    Qi, Yanli; Liu, Donghui; Luo, Mai; Jing, Xu; Wang, Peng; Zhou, Zhiqiang

    2016-03-01

    The stereoselective degradation and transformation of the enantiomers of the herbicide fluazifop-butyl in soil and water were studied to investigate the environmental behavior and chiral stability of the optical pure product. Its main chiral metabolite fluazifop was also monitored. LC/MS/MS with Chiralpak IC chiral column was used to separate the enantiomers of fluazifop-butyl and fluazifop. Validated enantioselective residue analysis methods were established with recoveries ranging from 77.1 to 115.4% and RSDs from 0.85 to 8.9% for the enantiomers. It was found the dissipation of fluazifop-butyl was rapid in the three studied soils (Beijing, Harbin and Anhui soil), and the degradation half-lives of the enantiomers ranged from 0.136 to 2.7 d. Enantioselective degradations were found in two soils. In Beijing soil, R-fluazifop-butyl was preferentially degraded leading to relative enrichment of S-enantiomer, but in Anhui soil, S-fluazifop-butyl dissipated faster. There was no conversion of the R-fluazifop-butyl into S-fluazifop-butyl or vice versa in the soils. The formation of fluazifop in the soils was rapidly accompanied with the fast degradation of fluazifop-butyl, and the enantioselectivity and the transformation of S-fluazifop to R-fluazifop were found. The degradation of fluazifop-butyl in water was also quick, with half-lives of the enantiomers ranging from 0.34 to 2.52 d, and there was no significant enantioselectivity of the degradation of fluazifop-butyl and the formation of fluazifop. The effects of pH on the degradation showed fluazifop-butyl enantiomers degraded faster in alkaline conditions. This study showed an evidence of enantioselective behavior and enantiomerization of the chiral herbicide fluazifop-butyl. PMID:26735732

  2. N-Butyl acrylate polymer composition for solar cell encapsulation and method

    NASA Technical Reports Server (NTRS)

    Gupta, Amitava (Inventor); Ingham, John D. (Inventor); Yavrouian, Andre H. (Inventor)

    1983-01-01

    A polymer syrup for encapsulating solar cell assemblies. The syrup includes uncrosslinked poly(n-butyl)acrylate dissolved in n-butyl acrylate monomer. Preparation of the poly(n-butyl)acrylate and preparation of the polymer syrup is disclosed. Methods for applying the polymer syrup to solar cell assemblies as an encapsulating pottant are described. Also included is a method for solar cell construction utilizing the polymer syrup as a dual purpose adhesive and encapsulating material.

  3. Molecular recognition study of Carbamazepine, antiseizure drug, by p-t-butyl calix(8)arene.

    PubMed

    Meenakshi, C; Jayabal, P; Ramakrishnan, V

    2014-03-25

    The formation of inclusion complex of Carbamazepine, a antiseizure drug molecule, with the supra molecule, p-t-butyl calix(8)arene was studied. p-t-Butyl calix(8)arene was the host molecule and Carbamazepine was the guest molecule. Optical absorption spectral studies were carried out to study the molecular recognition properties of p-t-butyl calix(8)arene with Carbamazepine. The stochiometry of the host-guest complex and the binding constant were determined.

  4. Inducing PLA/starch compatibility through butyl-etherification of waxy and high amylose starch.

    PubMed

    Wokadala, Obiro Cuthbert; Emmambux, Naushad Mohammad; Ray, Suprakas Sinha

    2014-11-01

    In this study, waxy and high amylose starches were modified through butyl-etherification to facilitate compatibility with polylactide (PLA). Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectroscopy and wettability tests showed that hydrophobic butyl-etherified waxy and high amylose starches were obtained with degree of substitution values of 2.0 and 2.1, respectively. Differential scanning calorimetry, tensile testing, and scanning electron microscopy (SEM) demonstrated improved PLA/starch compatibility for both waxy and high amylose starch after butyl-etherification. The PLA/butyl-etherified waxy and high amylose starch composite films had higher tensile strength and elongation at break compared to PLA/non-butyl-etherified composite films. The morphological study using SEM showed that PLA/butyl-etherified waxy starch composites had a more homogenous microstructure compared to PLA/butyl-etherified high amylose starch composites. Thermogravimetric analysis showed that PLA/starch composite thermal stability decreased with starch butyl-etherification for both waxy and high amylose starches. This study mainly demonstrates that PLA/starch compatibility can be improved through starch butyl-etherification.

  5. Inducing PLA/starch compatibility through butyl-etherification of waxy and high amylose starch.

    PubMed

    Wokadala, Obiro Cuthbert; Emmambux, Naushad Mohammad; Ray, Suprakas Sinha

    2014-11-01

    In this study, waxy and high amylose starches were modified through butyl-etherification to facilitate compatibility with polylactide (PLA). Fourier transform infrared spectroscopy, proton nuclear magnetic resonance spectroscopy and wettability tests showed that hydrophobic butyl-etherified waxy and high amylose starches were obtained with degree of substitution values of 2.0 and 2.1, respectively. Differential scanning calorimetry, tensile testing, and scanning electron microscopy (SEM) demonstrated improved PLA/starch compatibility for both waxy and high amylose starch after butyl-etherification. The PLA/butyl-etherified waxy and high amylose starch composite films had higher tensile strength and elongation at break compared to PLA/non-butyl-etherified composite films. The morphological study using SEM showed that PLA/butyl-etherified waxy starch composites had a more homogenous microstructure compared to PLA/butyl-etherified high amylose starch composites. Thermogravimetric analysis showed that PLA/starch composite thermal stability decreased with starch butyl-etherification for both waxy and high amylose starches. This study mainly demonstrates that PLA/starch compatibility can be improved through starch butyl-etherification. PMID:25129738

  6. California`s cleaner burning gasoline and methyl tertiary butyl ether

    SciTech Connect

    Denton, J.; Mazur, L.

    1995-12-31

    As of June 1, 1996, California is required to use cleaner-burning gasoline to help meet federal ambient air quality standards and reduce ambient air toxics. Cleaner-burning gasoline reduces smog-forming emissions from motor vehicles by 15% and air pollution by over three million pounds per day. This is equivalent to removing 3.5 million cars from California`s roads. To enhance combustion and thus reduce emissions, California cleaner burning gasoline is required to contain 2.0% oxygen by weight. This is achieved by addition of oxygenates, such as methyl tertiary butyl ether (MTBE). Ambient air data of MTBE derived from motor vehicle emissions and refueling activities has been measured in several pilot studies and at 22 urban sites as part of California`s Air Resources Board statewide toxics monitoring network. These activities have only recently been initiated and this paper will describe data collected to date.

  7. Degradation of methyl tert-butyl ether (MTBE) in water by glow discharge plasma.

    PubMed

    Tong, Shaoping; Ni, Yanyan; Shen, Chensi; Wen, Yuezhong; Jiang, Xuanzhen

    2011-01-01

    This study evaluated the ability of the glow discharge plasma (GDP) technique to degrade methyl tert-butyl ether (MTBE) in an aqueous solution. The results showed that a large amount of hydrogen peroxide and highly active *OH free radicals were produced during the treatment. Various experimental parameters including discharge current, initial MTBE concentration and initial pH played significant roles on MTBE degradation. In addition, Fe2+ had a catalytic effect on the degradation of MTBE, which is potentially attributable to the reaction between Fe3+ and the hydrated electron. It was also confirmed that GDP was comparable to electrocatalytic oxidation and high-density plasma and more efficient than photocatalytic degradation techniques. These results suggest that GDP may become a competitive MTBE wastewater treatment technology. PMID:22049704

  8. Study on antibacterial dental resin using tri-n-butyl(4-vinylbenzyl)phosphonium chloride.

    PubMed

    Kurata, Shigeaki; Hamada, Nobushiro; Kanazawa, Akihiko; Endo, Takeshi

    2011-01-01

    The antibacterial properties of a polymeric phosphonium salt were studied to determine its suitability as an additive to develop an antibacterial dental resin. The phosphonium salt monomer studied was tri-n-butyl(4-vinylbenzyl)phosphonium chloride (VP), and acrylic acid (AC) and methacryloyloxyethyl trimethyl ammonium chloride (MA) were used as controls. The antibacterial activity of these monomers and their corresponding polymers (PVP, PAC, and PMA) against Streptococcus mutans (S. mutans) was examined. When incubating S. mutans in a medium containing 10 μmol/mL for 24 hours, the antibacterial activity of PVP against S. mutans was high, while the antibacterial activity of PMA and VP was lower. AC, PAC and PMA exhibited the lowest antibacterial activity. The mechanical properties of the copolymers of methyl methacrylate, 2-hydroxyethyl methacrylate, and VP decreased as VP content increased, and were lower than those of poly(methyl methacrylate).

  9. Dangerous and cancer-causing properties of products and chemicals in the oil-refining and petrochemical industry--Part XXII: Health hazards from exposure to gasoline containing methyl tertiary butyl ether: study of New Jersey residents.

    PubMed

    Mehlman, M A

    1996-01-01

    Methyl tertiary butyl ether has caused the following cancers in rats and mice: kidney, testicular, liver, lymphomas, and leukemias. Thus, in the absence of adequate data on humans, it is biologically plausible and prudent to regard methyl tertiary butyl ether-for which there is sufficient evidence of carcinogenicity in experimental animals-as a probable human carcinogen. This means that some humans are at extreme risk of contracting cancers resulting from their exposure to oxygenated gasoline containing methyl tertiary butyl ether. Immediately after the introduction of methyl tertiary butyl ether into gasoline, many consumers of this product in New Jersey, New York, Alaska, Maine, Pennsylvania, Colorado, Arizona, Montana, Massachusetts, California, and other areas, experienced a variety of neurotoxic, allergic, and respiratory illnesses. These illnesses were similar to those suffered by refinery workers from the Oil, Chemical, and Atomic Workers Union who mixed methyl tertiary butyl ether with gasoline. Additionally, these illnesses occurred following exposure to extremely low levels of methyl tertiary butyl ether in gasoline, particularly when compared to the adverse health effects that occurred only after exposure to very high levels of conventional gasoline. Thus, gasoline containing methyl tertiary butyl ether exhibited substantially more toxicity in humans than gasoline without this additive. A number of oil industry-sponsored or influenced reports alleged that these illnesses were either unrelated to exposure to reformulated gasoline or were characteristic of some yet-to-be-identified communicable disease. These studies further alleged that the widespread concern was not about illness, but was merely a reaction to the odor and the five cent increase in the price of gasoline. To clarify the significance of this issue, it is important to note that consumers have been using gasoline for many decades, with complaints only occurring following exposure to high

  10. Evaluation of subchronic neurotoxicity of n-butyl acetate vapor.

    PubMed

    David, R M; Tyler, T R; Ouellette, R; Faber, W D; Banton, M I; Garman, R H; Gill, M W; O'Donoghue, J L

    1998-12-01

    n-Butyl acetate, a common industrial solvent, was selected by the US EPA as a chemical of concern for neurotoxicity as part of the Multisubstance Rule for the Testing of Neurotoxicity. The neurotoxic potential of n-butyl acetate was investigated in Sprague-Dawley rats using a functional observational battery, motor activity, neurohistopathology, and schedule-controlled operant behavior (SCOB) as indicators of neurotoxicity. Animals were exposed to concentrations of 0, 500, 1500, or 3000 ppm of n-butyl acetate for 6 hours per day for 65 exposures over 14 weeks. Functional observational battery and motor activity values for ad libitum-fed male and female rats were measured during Weeks -1, 4, 8, and 13. SCOB testing of food-restricted animals, using a multiple fixed ratio/fixed interval schedule, was conducted daily prior to each exposure to maintain the operant behavior; the data from Weeks -1, 4, 8, and 13 were evaluated for evidence of neurotoxicity. Transient signs of sedation and hypoactivity were observed only during exposure to the 1500 and 3000 ppm concentrations. The only signs of systemic toxicity were reduced body weights for the 3000 ppm ad libitum-fed groups and occasionally for the female 1500 ppm ad libitum-fed group. No evidence of neurotoxicity was seen during the functional observational battery examinations. Motor activity for the 3000 ppm male group was significantly (p < or = 0.05) higher than for the control group only during Week 4. No significant differences were observed among groups for Weeks 8 and 13. No significant differences in motor activity values were observed for female rats. No significant differences were seen in operant behavior at any test vapor concentration. Microscopic evaluations of sections from the brain, spinal cord (cervical and lumbar regions), dorsal and ventral spinal roots, dorsal root ganglia, sciatic nerve, and tibial nerve of animals in the control and 3000 ppm groups did not indicate any treatment-related effects

  11. The rotational spectrum of tertiary-butyl alcohol

    NASA Astrophysics Data System (ADS)

    Cohen, E. A.; Drouin, B. J.; Valenzuela, E. A.; Woods, R. C.; Caminati, W.; Maris, A.; Melandri, S.

    2010-03-01

    The rotational spectrum of tertiary-butyl alcohol has been recorded in selected regions between 8 and 500 GHz. Early data from the University of Wisconsin in the 8-40 GHz region have been combined with recent measurements from the University of Bologna and the Jet Propulsion Laboratory in the millimeter and submillimeter wavelength regions. The spectrum was fit over a wide range of J's and K's using a common set of parameters for both the A and E states. This paper describes the initial assignment at Wisconsin and the final procedure used to assign and fit the higher rotational states. The resulting molecular constants and their interpretation are discussed.

  12. Food additives

    PubMed Central

    Spencer, Michael

    1974-01-01

    Food additives are discussed from the food technology point of view. The reasons for their use are summarized: (1) to protect food from chemical and microbiological attack; (2) to even out seasonal supplies; (3) to improve their eating quality; (4) to improve their nutritional value. The various types of food additives are considered, e.g. colours, flavours, emulsifiers, bread and flour additives, preservatives, and nutritional additives. The paper concludes with consideration of those circumstances in which the use of additives is (a) justified and (b) unjustified. PMID:4467857

  13. Retrospective study of possible alpha-2 mu-globulin nephropathy and associated cell proliferation in male Fischer 344 rats dosed with t-butyl alcohol.

    PubMed Central

    Takahashi, K; Lindamood, C; Maronpot, R R

    1993-01-01

    Tert-butyl alcohol, an important commodity chemical, additive to unleaded gasoline, and contaminant of drinking water, was evaluated for toxicity and was found to enhance nephropathy in male Fischer 344 rats. Because male rats treated with t-butyl alcohol for 2 years had a low incidence of renal cortical tumors, additional renal sections for the 90-day toxicity study were examined for the presence of hyaline droplet accumulation, nephropathy, and evidence of replicative DNA synthesis (S-phase nuclei) to indirectly and retrospectively investigate a possible role of alpha-2 mu-globulin in the pathogenesis of the nephropathy. Dose levels for t-butyl alcohol were 0, 0.25, 0.5, 1, 2, and 4% (w/v) administered in drinking water. Significant body weight gain depressions were observed in all treated males, and there was an absolute weight loss in the 4% male group, none of which survived to the end of the study. Except for the 4% dose group, there was a treatment-related increase in hyaline droplet accumulation in the renal proximal tubules with crystalline, rectangular, and rhomboid forms of the protein evident. The severity of nephropathy was enhanced in treated rats, except for the 4% dose group. Replicative DNA synthesis, as measured by immunohistochemical staining for proliferating cell nuclear antigen, was increased in proximal tubules of rats dosed with 2% t-butyl alcohol. It is concluded that t-butyl alcohol exacerbated nephropathy in male Fischer 344 rats and increased renal accumulation of hyaline protein material consistent with alpha-2 mu-globulin deposition. Images FIGURE 2. FIGURE 3. FIGURE 4. FIGURE 5. FIGURE 7. PMID:7516874

  14. Effect of Parameters on Oxychlorination of Tert-Butyl Ethers

    PubMed Central

    Gaca, Jerzy; Gackowska, Alicja; Belt, Natalia

    2008-01-01

    The effect of concentration, molar ratios of reagents, pH, and temperature on formation of chloro-organic products in reaction of tert-butyl ethers with chloride ions and hydrogen peroxide has been determined. A significant effect of Cl− ions and H2O2 molar ratios on the rate of chloro-organic product formation has been observed. Studies on oxychlorination of tert-butylethyl ether (ETBE) at pH 7, 3.5, and 2.5 have been carried out. It was found that introduction of hydronium ions into the reaction system considerably hastened the process of chloro-organic product formation. Hydronium ions contribute to the formation of the reactive tert-butyl carbocation, which undergoes secondary reactions in the presence of reactive forms of chlorine and oxygen. Moreover, the effect of temperature on ETBE (tert-butylethyl ether) and MTBE (tert-butylmethyl ether) conversions was verified. The reactions of MTBE and ETBE oxychlorination were carried out at temperatures of 5°C, 20°C, and 35°C. PMID:19696944

  15. Production of butyl solvents from lignocellulose: An economic analysis

    SciTech Connect

    Wright, J D; Daling, R; Sandel, R L; Fitzpatrick, S W

    1986-11-01

    A process is described that produces butyl solvents, butanol, isopropanol, and ethanol from wood or other lignocellulosic feedstock. Two new elements of technology introduced are the processing batch reactor developed at SERI that produces high yields of fermentable sugars (hexoses and pentoses) at the appropriate concentration for the butyl solvents fermentation and a novel method of separating products using liquid-liquid extraction, which reduces the separation energy required to about 30% of energy required in the conventional batch method. Economic analysis suggests that the project is attractive at a feedstock capacity of 400,000 dry MTA or larger (178 million lb/yr solvents). There are, however, uncertainties associated with the project because of the relatively early stage of development of the key elements of the process technology and the sensitivity of the DCFIROR to estimated capital cost. A further conclusion is that the process economics would benefit greatly from reduced capital cost of the fermentation section. This could perhaps be accomplished by developing a continuous fermentation process. Such fermentation technology has been demonstrated on laboratory scale, but as far as is known, has not been developed to pilot scale. 21 refs., 4 figs., 3 tabs.

  16. The Rotational Spectrum of Tertiary-Butyl Alcohol

    NASA Astrophysics Data System (ADS)

    Cohen, E. A.; Drouin, B. J.; Valenzuela, E. A.; Woods, R. C.; Caminati, W.; Maris, A.; Melandri, S.

    2009-06-01

    Tertiary-butyl alcohol is a nearly spherical rotor for which the internal rotation axis of the t-butyl group is close to the c molecular axis in the ac plane. Methyl group torsional spittings are not observed in the ground state. Its 8 to 40 GHz rotational spectrum was reported at this meeting by Valenzuela and Woods in 1974 and in more detail in 1975. The parameters derived at that time from a fit to the E states with J,K≤ 20 have provided the basis for extending the measurements to > 500 GHz. The combined data set extends to J,K > 50 and is fit with the program SPFIT using a common set of parameters for both the A and E states. The general features of the spectrum and the fitting procedure will be described. The resulting molecular constants and their interpretation will be discussed. E.A. Valenzuela, and R. C. Woods, Abstract MF6, International Symposium on Molecular Spectroscopy, Columbus, OH, 1974 E.A. Valenzuela, and R. C. Woods, Abstract RG15, International Symposium on Molecular Spectroscopy, Columbus, OH, 1975 E.A. Valenzuela, Ph.D. Thesis, University of Wisconsin-Madison, 1975. H. M. Pickett, J. Mol. Spectrosc. 148 (1991) 271-377.

  17. [Chemical analytical aspects of hygiene safety of the use of methyl tertiary-butyl ether in the production of gasoline].

    PubMed

    Malysheva, A G; Rastyannikov, E G; Kozlova, N Yu; Artyushina, I Yu

    2014-01-01

    There was developed, certified and recommended for the practical application the technique for control in the water used as a high-octane oxygenated gasoline additive methyl tert-butyl ether with the use of chromatography-mass spectrometry method with a sensitivity of (0.005 mg/dm3) below the level of existing foreign regulations. Technique is introduced into the Federal Information Fund to ensure the unity of measurements. The possibility of applying the proposed method of analysis for monitoring chemical contamination of water sources and the quality control and safety of drinking water has been shown.

  18. Heats of formation of t-butyl peroxy radical and t-butyl diazyl ion: RRKM vs SSACM rate theories in systems with kinetic and competitive shifts.

    PubMed

    Shuman, Nicholas S; Bodi, Andras; Baer, Tomas

    2010-01-14

    The dissociations of energy-selected di-t-butyl peroxide and di-t-butyl diazene ions have been studied by threshold photoelectron-photoion coincidence (TPEPICO) spectroscopy. Di-t-butyl peroxide ions dissociate via two parallel channels: (1) methyl loss at a 0 K onset (E0) of 9.58 +/- 0.04 eV followed by a sequential dissociation of the daughter ion to produce C4H9O+ and acetone; and (2) the dominant dissociation channel, producing t-butyl ion and t-butyl peroxy radical at an E0 of 9.758 +/- 0.020 eV. Di-t-butyl diazene ions dissociate through three parallel channels: (1) a rearrangement to form isobutene ion; (2) C-N bond cleavage with the charge staying on the t-butyl diazyl species (E0 = 8.069 +/- 0.050 eV); and (3) C-N bond cleavage with the charge instead on the t-butyl (E0 = 8.122 +/- 0.050 eV); the coproduct for this latter channel is a weakly, or possibly unbound, N2...t-butyl structure. Both the peroxide and diazene ion dissociations produce metastable daughters, and the dissociation rates are modeled with two rate theories: the Rice-Ramsperger-Kassel-Marcus (RRKM) theory and a simplified version of the statistical adiabatic channel model (SSACM). Due to a large kinetic shift, RRKM incorrectly models the peroxide ion rate curve. Using SSACM, the heat of formation of t-butyl peroxy radical is determined to be DeltaH0Kdegrees = - 81.1 +/- 3.9 kJ mol-1, and, using B3LYP/6-311++G(d,p) thermal energy, DeltaH298Kdegrees = - 109.7 +/- 3.9 kJ mol-1. Due to a competitive shift of the higher energy channel onsets, RRKM also incorrectly models the diazene rate curves. The 298 K heat of formation of the t-butyl diazyl ion, which is bound by 14 kJ mol-1, is determined to be 701.2 +/- 5.9 kJ mol-1.

  19. 40 CFR 721.6920 - Butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... 40 Protection of Environment 31 2014-07-01 2014-07-01 false Butyl acrylate, polymer with... acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted silane. (a... butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

  20. 40 CFR 721.6920 - Butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... 40 Protection of Environment 32 2012-07-01 2012-07-01 false Butyl acrylate, polymer with... acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted silane. (a... butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

  1. 40 CFR 721.6920 - Butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... 40 Protection of Environment 32 2013-07-01 2013-07-01 false Butyl acrylate, polymer with... acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted silane. (a... butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

  2. 40 CFR 721.10418 - 1,2-Cyclohexanedicarboxylic acid, 1-butyl 2-(phenylmethyl) ester.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ...-butyl 2-(phenylmethyl) ester. 721.10418 Section 721.10418 Protection of Environment ENVIRONMENTAL...-(phenylmethyl) ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance is identified as 1,2-cyclohexanedicarboxylic acid, 1-butyl 2-(phenylmethyl) ester (PMN...

  3. 40 CFR 721.10418 - 1,2-Cyclohexanedicarboxylic acid, 1-butyl 2-(phenylmethyl) ester.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ...-butyl 2-(phenylmethyl) ester. 721.10418 Section 721.10418 Protection of Environment ENVIRONMENTAL...-(phenylmethyl) ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance is identified as 1,2-cyclohexanedicarboxylic acid, 1-butyl 2-(phenylmethyl) ester (PMN...

  4. 40 CFR 721.10418 - 1,2-Cyclohexanedicarboxylic acid, 1-butyl 2-(phenylmethyl) ester.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ...-butyl 2-(phenylmethyl) ester. 721.10418 Section 721.10418 Protection of Environment ENVIRONMENTAL...-(phenylmethyl) ester. (a) Chemical substance and significant new uses subject to reporting. (1) The chemical substance is identified as 1,2-cyclohexanedicarboxylic acid, 1-butyl 2-(phenylmethyl) ester (PMN...

  5. REDUCTIVE ACTIVATION OF DIOXYGEN FOR DEGRADATION OF METHYL TERT-BUTYL ETHER BY BIFUNCTION

    EPA Science Inventory

    Bifunctional aluminum is prepared by sulfating aluminum metal with sulfuric acid. The use of bifunctional aluminum to degrade methyl tert-butyl ether (MTBE) in the presence of dioxygen has been examined using batch systems. Primary degradation products were tert-butyl alcohol, ...

  6. 40 CFR 721.6920 - Butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... 40 Protection of Environment 31 2011-07-01 2011-07-01 false Butyl acrylate, polymer with... acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted silane. (a... butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

  7. 40 CFR 721.6920 - Butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

    Code of Federal Regulations, 2010 CFR

    2010-07-01

    ... 40 Protection of Environment 30 2010-07-01 2010-07-01 false Butyl acrylate, polymer with... acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted silane. (a... butyl acrylate, polymer with substituted methyl styrene, methyl methacrylate, and substituted...

  8. Subchronic exposure to ethyl tertiary butyl ether resulting in genetic damage in Aldh2 knockout mice.

    PubMed

    Weng, Zuquan; Suda, Megumi; Ohtani, Katsumi; Mei, Nan; Kawamoto, Toshihiro; Nakajima, Tamie; Wang, Rui-Sheng

    2013-09-15

    Ethyl tertiary butyl ether (ETBE) is biofuel additive recently used in Japan and some other countries. Limited evidence shows that ETBE has low toxicity. Acetaldehyde (AA), however, as one primary metabolite of ETBE, is clearly genotoxic and has been considered to be a potential carcinogen. The aim of this study was to evaluate the effects of ALDH2 gene on ETBE-induced genotoxicity and metabolism of its metabolites after inhalation exposure to ETBE. A group of wild-type (WT) and Aldh2 knockout (KO) C57BL/6 mice were exposed to 500ppm ETBE for 1-6h, and the blood concentrations of ETBE metabolites, including AA, tert-butyl alcohol and 2-methyl-1,2-propanediol, were measured. Another group of mice of WT and KO were exposed to 0, 500, 1750, or 5000ppm ETBE for 6h/day with 5 days per weeks for 13 weeks. Genotoxic effects of ETBE in these mice were measured by the alkaline comet assay, 8-hydroxyguanine DNA-glycosylase modified comet assay and micronucleus test. With short-term exposure to ETBE, the blood concentrations of all the three metabolites in KO mice were significantly higher than the corresponding concentrations of those in WT mice of both sexes. After subchronic exposure to ETBE, there was significant increase in DNA damage in a dose-dependent manner in KO male mice, while only 5000ppm exposure significantly increased DNA damage in male WT mice. Overall, there was a significant sex difference in genetic damage in both genetic types of mice. These results showed that ALDH2 is involved in the detoxification of ETBE and lack of enzyme activity may greatly increase the sensitivity to the genotoxic effects of ETBE, and male mice were more sensitive than females. PMID:23810710

  9. Methyl tert-butyl ether (MTBE) degradation by a microbial consortium.

    PubMed

    Fortin, N Y; Morales, M; Nakagawa, Y; Focht, D D; Deshusses, M A

    2001-06-01

    The widespread use of methyl tert-butyl ether (MTBE) as a gasoline additive has resulted in a large number of cases of groundwater contamination. Bioremediation is often proposed as the most promising alternative after treatment. However, MTBE biodegradation appears to be quite different from the biodegradation of usual gasoline contaminants such as benzene, toluene, ethyl benzene and xylene (BTEX). In the present paper, the characteristics of a consortium degrading MTBE in liquid cultures are presented and discussed. MTBE degradation rate was fast and followed zero order kinetics when added at 100 mg l(-1). The residual MTBE concentration in batch degradation experiments ranged from below the detection limit (1 microg l(-1)) to 50 microg l(-1). The specific activity of the consortium ranged from 7 to 52 mgMTBE g(dw)(-1) h(-1) (i.e. 19-141 mgCOD g(dw) (-1) h(-1)). Radioisotope experiments showed that 79% of the carbon-MTBE was converted to carbon-carbon dioxide. The consortium was also capable of degrading a variety of hydrocarbons, including tert-butyl alcohol (TBA), tert-amyl methyl ether (TAME) and gasoline constituents such as benzene, toluene, ethylbenzene and xylene (BTEX). The consortium was also characterized by a very slow growth rate (0.1 d(-1)), a low overall biomass yield (0.11 gdw g(-1)MTBE; i.e. 0.040 gdw gCOD(-1)), a high affinity for MTBE and a low affinity for oxygen, which may be a reason for the slow or absence of MTBE biodegradation in situ. Still, the results presented here show promising perspectives for engineering the in situ bioremediation of MTBE.

  10. Methyl tert butyl ether targets developing vasculature in zebrafish (Danio rerio) embryos

    PubMed Central

    Bonventre, Josephine A.; White, Lori A.; Cooper, Keith R.

    2015-01-01

    Disruption of vascular endothelial growth factor (VEGF) signaling during early development results in abnormal angiogenesis and increased vascular lesions. Embryonic exposure to 0.625 to 10 mM methyl tert butyl ether (MTBE), a highly water soluble gasoline additive, resulted in a dose dependent increase in pooled blood in the common cardinal vein (CCV), cranial hemorrhages and abnormal intersegmental vessels (ISVs). The EC50s for the lesions ranked in terms of likelihood to occur with MTBE exposure were: pooled blood in the CCV, 3.2 mM [95 % CI: 2.2 – 4.7] > cranial hemorrhage, 11 mM [5.9 – 20.5] > abnormal ISV, 14.5 mM [6.5 – 32.4]. Organ systems other than the vascular system appear to develop normally, which suggests MTBE toxicity targets developing blood vessels. Equal molar concentrations (0.625 to 10 mM) of the primary metabolites, tertiary butyl alcohol (TBA) and formaldehyde, did not result in vascular lesions, which suggested that the parent compound is responsible for the toxicity. Stage specific exposures were carried out to determine the developmental period most sensitive to MTBE vascular disruption. Embryos treated until 6-somites or treated after Prim-5 stages did not exhibit a significant increase in lesions, while embryos treated between 6-somites and Prim-5 had a significant increase in vascular lesions (p ≤ 0.05). During the critical window for MTBE-induced vascular toxicity, expression of vegfa, vegfc, and flk1/kdr were significantly decreased 50, 70 and 40%, respectively. This is the first study to characterize disruption in vascular development following embryonic exposure to MTBE. The unique specificity of MTBE to disrupt angiogenesis may be mediated by the down regulation of critical genes in the VEGF pathway. PMID:21684239

  11. 40 CFR 799.1560 - Diethylene glycol butyl ether and diethylene glycol butyl ether acetate.

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... with control females, and males and females administered the high dose shall be cohabited. Endpoints to... Days 4, 7, 14, and 21. Litters shall be standardized on day 4 in accordance with the reproductive and.... An additional 20 males and 40 females will have to be added to the subchronic study for this test....

  12. 40 CFR 799.1560 - Diethylene glycol butyl ether and diethylene glycol butyl ether acetate.

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... with control females, and males and females administered the high dose shall be cohabited. Endpoints to... Days 4, 7, 14, and 21. Litters shall be standardized on day 4 in accordance with the reproductive and.... An additional 20 males and 40 females will have to be added to the subchronic study for this test....

  13. 40 CFR 799.1560 - Diethylene glycol butyl ether and diethylene glycol butyl ether acetate.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ... with control females, and males and females administered the high dose shall be cohabited. Endpoints to... Days 4, 7, 14, and 21. Litters shall be standardized on day 4 in accordance with the reproductive and.... An additional 20 males and 40 females will have to be added to the subchronic study for this test....

  14. 40 CFR 799.1560 - Diethylene glycol butyl ether and diethylene glycol butyl ether acetate.

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... with control females, and males and females administered the high dose shall be cohabited. Endpoints to... Days 4, 7, 14, and 21. Litters shall be standardized on day 4 in accordance with the reproductive and.... An additional 20 males and 40 females will have to be added to the subchronic study for this test....

  15. Reaction products and mechanisms for the reaction of n-butyl vinyl ether with the oxidants OH and Cl: Atmospheric implications

    NASA Astrophysics Data System (ADS)

    Colmenar, Inmaculada; Martín, Pilar; Cabañas, Beatriz; Salgado, Sagrario; Tapia, Araceli; Martínez, Ernesto

    2015-12-01

    A reaction product study for the degradation of butyl vinyl ether (CH3(CH2)3OCHdbnd CH2) by reaction with chlorine atoms (Cl) and hydroxyl radicals (OH) has been carried out using Fourier Transform Infrared absorption spectroscopy (FTIR) and/or Gas Chromatography-Mass Spectrometry with a Time of Flight analyzer (GC-TOFMS). The rate coefficient for the reaction of butyl vinyl ether (BVE) with chlorine atoms has also been evaluated for the first time at room temperature (298 ± 2) K and atmospheric pressure (708 ± 8) Torr. The rate coefficient obtained was (9.9 ± 1.5) × 10-10 cm3 molecule-1 s-1 and this indicates the high reactivity of butyl vinyl ether with Cl atoms. However, this value may be affected by the dark reaction of BVE with Cl2. The results of a qualitative study of the Cl reaction show that the main oxidation products are butyl formate (CH3(CH2)3OC(O)H), butyl chloroacetate (CH3(CH2)3OC(O)CH2Cl and formyl chloride (HCOCl). Individual yields in the ranges ∼16-40% and 30-70% in the absence and presence of NOx, respectively, have been estimated for these products. In the OH reaction, butyl formate and formic acid were identified as the main products, with yields of around 50 and 20%, respectively. Based on the results of this work and a literature survey, the addition of OH radicals and Cl atoms at the terminal C atom of the double bond in CH3(CH2)3OCHdbnd CH2 has been proposed as the first step in the reaction mechanism for both of the studied oxidants. The tropospheric lifetime of butyl vinyl ether is very short and, as a consequence, it will be rapidly degraded and will only be involved in tropospheric chemistry at a local level. The degradation products of these reactions should be considered when evaluating the atmospheric impact.

  16. Complexes of tetra-tert-butyl-tetraazaporphine with Al(III) and Zr(IV) cations as fluoride selective ionophores.

    PubMed

    Górski, Lukasz; Mroczkiewicz, Monika; Pietrzak, Mariusz; Malinowska, Elzbieta

    2009-02-01

    In this work, complexes of Zr(IV) and Al(III) cations with 2,7,12,17-tetra-tert-butyl-5,10,15,20-tetraazaporphine (TAP) were tested as ionophores in plasticized PVC membranes of ion-selective electrodes. It was found that both tested ionophores show enhanced affinity towards fluoride anion. High fluoride selectivity was observed in the presence of anionic or cationic additives in the membrane, which indicates that proposed compounds work according to charged or neutral carrier mechanism, depending on membrane composition and pretreatment. tert-Butyl substituents, present in the structure of tested compounds, were supposed to prevent formation of ionophore dimers within the membrane phase. This process was found to be responsible for some unfavorable potentiometric properties of electrodes based on complexes of Zr(IV) and Al(III) cations with porphyrins (compounds closely related to tetra-tert-butyl-5,10,15,20-tetraazaporphine). As it was shown using spectrophotometrical measurements, Al(III)-TAP was not susceptible to dimerization, while dimer formation was observed for Zr(IV)-TAP. In full agreement with these observations, electrodes with membranes containing Al(III)-TAP responded in near-Nernstian and fast manner towards fluoride anion, while the employment of Zr(IV)-TAP as ionophore resulted in super-Nernstian and sluggish response. Plasticized PVC membranes doped with Al(III)-TAP and 20mol% of lipophilic anionic additives shown remarkable F(-) selectivity, with selectivity coefficients, logK(F-pot.).(Y-), as follows: -4.4 (Y(-)Br(-)), -4.3 (Cl(-)), -4.2 (NO(3)(-)), -3.6 (SCN(-)), -2.9 (ClO(4)(-)). PMID:19166721

  17. Interactions between water and 1-butyl-1-methylpyrrolidinium ionic liquids

    SciTech Connect

    Fadeeva, Tatiana A.; DeVine, Jessalyn A.; Castner, Edward W.; Husson, Pascale; Costa Gomes, Margarida F.; Greenbaum, Steven G.

    2015-08-14

    We report experimental results on the diffusivity of water in two ionic liquids obtained using the pulsed-gradient spin-echo NMR method. Both ionic liquids have the same cation, 1-butyl-1-methylpyrrolidinium, but different trifluoromethyl-containing anions. One has a strongly hydrophobic anion, bis(trifluoromethylsulfonyl)amide, while the second has a hydrophilic anion, trifluoromethylsulfonate. Transport of water in these ionic liquids is much faster than would be predicted from hydrodynamic laws, indicating that the neutral water molecules experience a very different friction than the anions and cations at the molecular level. Temperature-dependent viscosities, conductivities, and densities are reported as a function of water concentration to further analyze the properties of the ionic liquid-water mixtures. These results on the properties of water in ionic liquids should be of interest to researchers in diverse areas ranging from separations, solubilizing biomass and energy technologies.

  18. Picosecond photoexcitation dynamics in poly(3-butyl-thiophene) films

    NASA Astrophysics Data System (ADS)

    Frolov, S. V.; Wei, X.; Gellermann, W.; Vardeny, Z. V.; Ehrenfreund, E.

    1998-02-01

    We have studied photoexcitation dynamics in thin films of poly(3-butyl-thiophene) [P3BT] using ps transient and cw photomodulation techniques, streak camera imaging, electroabsorption and optically detected magnetic resonance spectroscopies. We have determined that intrachain excitons are the primary photoexcitations with a characteristic transient photomodulation spectrum consisting of two photoinduced absorption bands in the near IR spectral range and a broad stimulated emission band in the visible spectral region. The photogenerated excitons are relatively short-lived (150 ps) and can subsequently decay into polaron pairs and triplets, which are longer-lived excitations with lifetimes of order ms. We do not find stimulated emission in very thin P3BT films and this is attributed to high defect concentration close to the film surface.

  19. Interactions between water and 1-butyl-1-methylpyrrolidinium ionic liquids.

    PubMed

    Fadeeva, Tatiana A; Husson, Pascale; DeVine, Jessalyn A; Costa Gomes, Margarida F; Greenbaum, Steven G; Castner, Edward W

    2015-08-14

    We report experimental results on the diffusivity of water in two ionic liquids obtained using the pulsed-gradient spin-echo NMR method. Both ionic liquids have the same cation, 1-butyl-1-methylpyrrolidinium, but different trifluoromethyl-containing anions. One has a strongly hydrophobic anion, bis(trifluoromethylsulfonyl)amide, while the second has a hydrophilic anion, trifluoromethylsulfonate. Transport of water in these ionic liquids is much faster than would be predicted from hydrodynamic laws, indicating that the neutral water molecules experience a very different friction than the anions and cations at the molecular level. Temperature-dependent viscosities, conductivities, and densities are reported as a function of water concentration to further analyze the properties of the ionic liquid-water mixtures. These results on the properties of water in ionic liquids should be of interest to researchers in diverse areas ranging from separations, solubilizing biomass and energy technologies. PMID:26277141

  20. Interactions between water and 1-butyl-1-methylpyrrolidinium ionic liquids.

    PubMed

    Fadeeva, Tatiana A; Husson, Pascale; DeVine, Jessalyn A; Costa Gomes, Margarida F; Greenbaum, Steven G; Castner, Edward W

    2015-08-14

    We report experimental results on the diffusivity of water in two ionic liquids obtained using the pulsed-gradient spin-echo NMR method. Both ionic liquids have the same cation, 1-butyl-1-methylpyrrolidinium, but different trifluoromethyl-containing anions. One has a strongly hydrophobic anion, bis(trifluoromethylsulfonyl)amide, while the second has a hydrophilic anion, trifluoromethylsulfonate. Transport of water in these ionic liquids is much faster than would be predicted from hydrodynamic laws, indicating that the neutral water molecules experience a very different friction than the anions and cations at the molecular level. Temperature-dependent viscosities, conductivities, and densities are reported as a function of water concentration to further analyze the properties of the ionic liquid-water mixtures. These results on the properties of water in ionic liquids should be of interest to researchers in diverse areas ranging from separations, solubilizing biomass and energy technologies.

  1. Modeling Low Density Polyethylene with Precisely Placed Butyl Branches

    NASA Astrophysics Data System (ADS)

    Rojas, Giovanni; Wagener, Kenneth B.

    Polyethylene (PE) is a commodity produced on a massive scale and also is one of the most studied macromolecules. Crystallinity can be controlled by copolymerizing ethylene with α-olefins, producing a wide range of material responses. Physical properties of PE, obtained via α olefin copolymerization, depend on the branch content that is directly related to the comonomer incorporation into the PE backbone. Materials with unknown primary structures are produced via chaingrowth chemistry, because unwanted side reactions generate defects in the main backbone that alter the morphological behavior and thermal response. Acyclic diene metathesis (ADMET) polymerization/hydrogenation methodology produce perfect sequenced copolymers of ethylene with α-olefins. Synthesis and thermal properties of PE with butyl branches precisely placed along the polymer backbone using ADMET chemistry is described within.

  2. Endocrine disrupting effects of butylated hydroxyanisole (BHA - E320)

    PubMed Central

    POP, ANCA; KISS, BELA; LOGHIN, FELICIA

    2013-01-01

    Butylated hydroxyanisole (BHA) is extensively used as antioxidant in foods, food packaging, cosmetics and pharmaceuticals. In the past years, it raised concerns regarding its possible endocrine disrupting effect. The existing in vitro studies indicate that BHA presents a weak estrogenic effect and also anti-androgenic properties while an in vivo study found it to have antiestrogenic properties. There is no sufficient data available at the moment to draw a conclusion regarding the safety of BHA when referring to its endocrine disrupting effect. Since a fraction of the population might be exposed to doses superior to the acceptable daily intake (ADI), it is important to gather more in vitro and in vivo data concerning the potential effects that BHA might have alone, but also in mixtures with natural hormones or other endocrine disrupting compounds. PMID:26527908

  3. New MTBE design now commercial. [Methyl tertiary butyl ether

    SciTech Connect

    Smith, L.A.; Huddleston, M.N.

    1982-03-01

    MTBE is considered by many to be the most promising octane booster to replace lead in gasoline during the 1980s. MTBE (methyl tetriary butyl ether) is made by combining methanol and isobutylene. The economic attractiveness for making this gasoline component is greatly improved by using a patented catalyst support system to give simultaneous reaction and distillation in a standard carbon steel distillation tower. The description of the process is accompanied by a simplified flow diagram and followed by the description of process variables affecting good reaction kinetics, catalyst life, and corrosion prevention. It is demonstrated that by using the technology described the production of high purity MTBE from dilute refinery streams is now economically feasible.

  4. Biocompatibility of wollastonite-poly(N-butyl-2-cyanoacrylate) composites.

    PubMed

    de Sena, Lídia Ágata; de Almeida, Marcelo Sanmartin; de Oliveira Fernandes, Gustavo V; Guerra Bretaña, Rosa M; Castro-Silva, Igor Iuco; Granjeiro, José Mauro; Achete, Carlos Alberto

    2014-08-01

    Wollastonite-poly(n-butyl-2-cyanoacrylate) composite (W-BCA) has been proposed to immobilize anatomically bone fragments in order to achieve an optimal healing process. The present study evaluated the in vitro and in vivo behavior of three types of fillers: powdered natural wollastonite (Wn), synthetic pseudowollastonite powder (Ws), and synthetic pseudowollastonite powder coated with 5% acetyl tributyl citrate (Wst). The Wst-BCA composite underwent a higher degradability in the real-time degradation test and a superior cytotoxic effect; whereas the Wn-BCA composite showed a higher degradability in the accelerated test with no cytotoxicity. The formation of an extracellular collagenous matrix deposit on its surface and the most favorable new bone formation on Wn-BCA indicate its potential for bone adhesive use in unstable orthopedic traumas.

  5. Use of butyl-2-cyanoacrylate in rabbit auricular cartilage.

    PubMed

    Fung, R Q; Ronis, M L; Mohr, R M

    1985-07-01

    Since the nonsuture repair of blood vessels with methyl-2-cyanoacrylate was described in 1960, the advantages of a tissue adhesive over conventional sutures became evident. A survey of 115 otolaryngology programs showed that cyanoacrylates, mainly butyl-2-cyanoacrylate (B2C), are used more extensively than indicated in the literature. Cartilage grafts are commonly used in facial plastic procedures. In a study comparing B2C with conventional suture techniques in securing rabbit auricular cartilage autografts, sutures were used in the left control ear and B2C was used in the right experimental ear. Rabbits sacrificed at two weeks to 12 months showed graft viability in all samples and no statistically significant histologic difference between the grafts secured by either method.

  6. Hydrogen Atom Reactivity toward Aqueous tert-Butyl Alcohol

    SciTech Connect

    Lymar S. V.; Schwarz, H.A.

    2012-02-09

    Through a combination of pulse radiolysis, purification, and analysis techniques, the rate constant for the H + (CH{sub 3}){sub 3}COH {yields} H{sub 2} + {sm_bullet}CH{sub 2}C(CH{sub 3}){sub 2}OH reaction in aqueous solution is definitively determined to be (1.0 {+-} 0.15) x 10{sup 5} M{sup -1} s{sup -1}, which is about half of the tabulated number and 10 times lower than the more recently suggested revision. Our value fits on the Polanyi-type, rate-enthalpy linear correlation ln(k/n) = (0.80 {+-} 0.05){Delta}H + (3.2 {+-} 0.8) that is found for the analogous reactions of other aqueous aliphatic alcohols with n equivalent abstractable H atoms. The existence of such a correlation and its large slope are interpreted as an indication of the mechanistic similarity of the H atom abstraction from {alpha}- and {beta}-carbon atoms in alcohols occurring through the late, product-like transition state. tert-Butyl alcohol is commonly contaminated by much more reactive secondary and primary alcohols (2-propanol, 2-butanol, ethanol, and methanol), whose content can be sufficient for nearly quantitative scavenging of the H atoms, skewing the H atom reactivity pattern, and explaining the disparity of the literature data on the H + (CH{sub 3}){sub 3}COH rate constant. The ubiquitous use of tert-butyl alcohol in pulse radiolysis for investigating H atom reactivity and the results of this work suggest that many other previously reported rate constants for the H atom, particularly the smaller ones, may be in jeopardy.

  7. Phosphazene additives

    DOEpatents

    Harrup, Mason K; Rollins, Harry W

    2013-11-26

    An additive comprising a phosphazene compound that has at least two reactive functional groups and at least one capping functional group bonded to phosphorus atoms of the phosphazene compound. One of the at least two reactive functional groups is configured to react with cellulose and the other of the at least two reactive functional groups is configured to react with a resin, such as an amine resin of a polycarboxylic acid resin. The at least one capping functional group is selected from the group consisting of a short chain ether group, an alkoxy group, or an aryloxy group. Also disclosed are an additive-resin admixture, a method of treating a wood product, and a wood product.

  8. Potlining Additives

    SciTech Connect

    Rudolf Keller

    2004-08-10

    In this project, a concept to improve the performance of aluminum production cells by introducing potlining additives was examined and tested. Boron oxide was added to cathode blocks, and titanium was dissolved in the metal pool; this resulted in the formation of titanium diboride and caused the molten aluminum to wet the carbonaceous cathode surface. Such wetting reportedly leads to operational improvements and extended cell life. In addition, boron oxide suppresses cyanide formation. This final report presents and discusses the results of this project. Substantial economic benefits for the practical implementation of the technology are projected, especially for modern cells with graphitized blocks. For example, with an energy savings of about 5% and an increase in pot life from 1500 to 2500 days, a cost savings of $ 0.023 per pound of aluminum produced is projected for a 200 kA pot.

  9. Exposure to methyl tertiary-butyl ether from oxygenated gasoline in Stamford, Connecticut

    SciTech Connect

    White, M.C.; Johnson, C.A.; Ashley, D.L.

    1995-05-01

    In 1993, state health officials in Connecticut invited the Centers for Disease Control and Prevention (CDC) to assist in an investigation of exposure to methyl tertiary-butyl ether in oxygenated gasoline in Stamford, Connecticut. Venous blood samples were collected from 14 commuters and from 30 other persons who worked in the vicinity of traffic or automobiles, and the samples were analyzed for methyl tertiary-butyl ether, tertiary-butyl alcohol, benzene, m-/p-xylene, o-xylene, and toluene. The highest levels of methyl tertiary-butyl ether in blood were measured among gasoline service station attendants (median = 15 {mu}g/l, range = 7.6-28.9 {mu}g/l). Blood levels of methyl tertiary-butyl ether were highly variable among persons who worked in car-repair shops (median = 1.73 {mu}g/l, range = 0.17-36.7 {mu}/l) and were generally lowest among commuters (median = 0.11 {mu}g/l, range = <0.05-2.60 {mu}g/l). Blood levels of methyl tertiary-butyl ether were correlated strongly with personal-breathing-zone samples of methyl tertiary-butyl ether and blood levels of other volatile organic compounds. This exposure information should prove useful to a future risk analysis of this high-volume chemical. 18 refs., 5 figs., 2 tabs.

  10. Studies on the Conformational Landscape of Tert-Butyl Acetate Using Microwave Spectroscopy and Quantum Chemical Calculations

    NASA Astrophysics Data System (ADS)

    Zhao, YueYue; Mouhib, Halima; Li, Guohua; Stahl, Wolfgang; Kleiner, Isabelle

    2014-06-01

    The tert-Butyl acetate molecule was studied using a combination of quantum chemical calculations and molecular beam Fourier transform microwave spectroscopy in the 9 to 14 GHz range. Due to its rather rigid frame, the molecule possesses only two different conformers: one of Cs and one of C1 symmetry. According to ab initio calculations, the Cs conformer is 46 kJ/mol lower in energy and is the one observed in the supersonic jet. We report on the structure and dynamics of the most abundant conformer of tert-butyl acetate, with accurate rotational and centrifugal distortion constants. Additionally, the barrier to internal rotation of the acetyl methyl group was determined. Splittings due to the internal rotation of the methyl group of up to 1.3 GHz were observed in the spectrum. Using the programs XIAM and BELGI-Cs, we determine the barrier height to be about 113 cm-1 and compare the molecular parameters obtained from these two codes. Additionally, the experimental rotational constants were used to validate numerous quantum chemical calculations. This study is part of a larger project which aims at determining the lowest energy conformers of organic esters and ketones which are of interest for flavor or perfume synthetic applications Project partly supported by the PHC PROCOPE 25059YB.

  11. Two-year drinking water carcinogenicity study of methyl tertiary-butyl ether (MTBE) in Wistar rats.

    PubMed

    Dodd, Darol; Willson, Gabrielle; Parkinson, Horace; Bermudez, Edilberto

    2013-07-01

    Methyl tertiary-butyl ether (MTBE) has been used as a gasoline additive to reduce tailpipe emissions and its use has been discontinued. There remains a concern that drinking water sources have been contaminated with MTBE. A two-year drinking water carcinogenicity study of MTBE was conducted in Wistar rats (males, 0, 0.5, 3, 7.5 mg ml(-1); and females, 0, 0.5, 3, and 15 mg ml(-1)). Body weights were unaffected and water consumption was reduced in MTBE-exposed males and females. Wet weights of male kidneys were increased at the end of two years of exposure to 7.5 mg ml(-1) MTBE. Chronic progressive nephropathy was observed in males and females, was more severe in males, and was exacerbated in the high MTBE exposure groups. Brain was the only tissue with a statistically significant finding of neoplasms. One astrocytoma (1/50) was found in a female rat (15 mg ml(-1)). The incidence of brain astrocytomas in male rats was 1/50, 1/50, 1/50 and 4/50 for the 0, 0.5, 3 and 7.5 mg ml(-1) exposure groups, respectively. This was a marginally significant statistical trend, but not statistically significant when pairwise comparisons were made or when multiple comparisons were taken into account. The incidence of astrocytoma fell within historical control ranges for Wistar rats, and the brain has not been identified as a target organ following chronic administration of MTBE, ethyl tert-butyl ether, or tertiary butyl alcohol (in drinking water) to mice and rats. We conclude that the astrocytomas observed in this study are not associated with exposure to MTBE.

  12. Sorption of methyl tert-butyl ether (MTBE) and tert-butyl alcohol (TBA) to synthetic resins.

    PubMed

    Bi, Erping; Haderlein, Stefan B; Schmidt, Torsten C

    2005-10-01

    Methyl tert-butyl ether (MTBE) is a widely used gasoline oxygenate. Contamination of MTBE and its major degradation product tert-butyl alcohol (TBA) in groundwater and surface water has received great attention. However, sorption affinity and sorption mechanisms of MTBE and TBA to synthetic resins, which can be potentially used in removal of these contaminants from water, in passive sampling, or in enrichment of bacteria, have not been studied systemically. In this study, kinetic and equilibrium sorption experiments (single solute and binary mixtures) on four synthetic resins were conducted. The sorption affinity of the investigated sorbents for MTBE and TBA decreases in the order Ambersorb 563>Optipore L493>Amberlite XAD4>Amberlite XAD7, and all show higher sorption affinity for MTBE than for TBA. Binary experiments with o-xylene, a major compound of gasoline as co-contaminant, imply that all resins preferentially sorb o-xylene over MTBE or TBA, i.e., there is sorption competition. In the equilibrium aqueous concentration (Ceq) range (0.1-139.0 mg/L for MTBE, and 0.01-48.4 mg/L for TBA), experimental and modeling results as well as sorbent characteristics indicate that micropore filling and/or some other type of adsorption process (e.g., adsorption to specific sites of high sorption potential at low concentrations) rather than partitioning were the dominant sorption mechanisms. Optipore L493 has favourable sorption and desorption characteristics, and is a suitable sorbent, e.g., in bacteria enrichment or passive sampling for moderately polar compounds. However, for highly polar compounds such as TBA, Ambersorb 563 might be a better choice, especially in water treatment.

  13. 21 CFR 172.115 - BHT.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... BHT (butylated hydroxytoluene), alone or in combination with other antioxidants permitted in this... antioxidant in foods, as follows: Food Limitations (total BHA and BHT) parts per million Dehydrated...

  14. Understanding the redox shuttle stability of 3,5-di-tert-butyl-1,2-dimethoxybenzene for overcharge protection of lithium-ion batteries.

    SciTech Connect

    Zhang, Z.; Zhang, L.; Schlueter, J. A.; Redfern, P. C.; Curtiss, L.; Amine, K.

    2010-01-01

    3,5-di-tert-butyl-1,2-dimethoxybenzene (DBDB) has been synthesized as a new redox shuttle additive for overcharge protection of lithium-ion batteries. DBDB can easily dissolve in carbonate-based electrolytes, which facilitates its practical use in lithium-ion batteries; however, it has poor electrochemical stability compared to 2,5-di-tert-butyl-1,4-dimethoxybenzene (DDB). The structures of DBDB and DDB were investigated using X-ray crystallography and density functional calculations. The structures differ in the conformations of the alkoxy bonds probably due to the formation of an intramolecular hydrogen bond in the case of DBDB. We investigated reaction energies for decomposition pathways of neutral DBDB and DDB and their radical cations and found little difference in the reaction energies, although it is clear that kinetically, decomposition of DBDB is more favorable.

  15. Identification of volatile butyl rubber thermal-oxidative degradation products by cryofocusing gas chromatography/mass spectrometry (cryo-GC/MS).

    SciTech Connect

    Smith, Jonell Nicole; White, Michael Irvin; Bernstein, Robert; Hochrein, James Michael

    2013-02-01

    Chemical structure and physical properties of materials, such as polymers, can be altered as aging progresses, which may result in a material that is ineffective for its envisioned intent. Butyl rubber formulations, starting material, and additives were aged under thermal-oxidative conditions for up to 413 total days at up to 124 ÀC. Samples included: two formulations developed at Kansas City Plant (KCP) (#6 and #10), one commercially available formulation (#21), Laxness bromobutyl 2030 starting material, and two additives (polyethylene AC-617 and Vanax MBM). The low-molecular weight volatile thermal-oxidative degradation products that collected in the headspace over the samples were preconcentrated, separated, and detected using cryofocusing gas chromatography mass spectrometry (cryo-GC/MS). The majority of identified degradation species were alkanes, alkenes, alcohols, ketones, and aldehydes. Observations for Butyl #10 aged in an oxygen-18 enriched atmosphere (18O2) were used to verify when the source of oxygen in the applicable degradation products was from the gaseous environment rather than the polymeric mixture. For comparison purposes, Butyl #10 was also aged under non-oxidative thermal conditions using an argon atmosphere.

  16. Biotransformation at 10 C of di-n-butyl phthalate in subsurface microcosms

    SciTech Connect

    Chauret, C.; Inniss, W.E.; Mayfield, C.I.

    1996-09-01

    Di-n-butyl phthalate (DBP) was found to be transformed by microorganisms under aerobic and anaerobic conditions at 10 C in microcosms simulating the Canadian Forces Base (CFB) Borden subsurface environment. Biotransformation of DBP was observed under aerobic, nitrate-reducing, Fe(III)-reducing, and sulfate-reducing conditions. The biotransformation of DBP in the microcosms was significantly decrease3d as the redox potential was lowered, especially under sulfate-reducing conditions. However, other factors such as nutrient depletion and buildup of toxic intermediates could have affected the biotransformation rates. The highest DBP biotransformation rate (0.57 {micro}g DBP{center_dot}g sediment{sup {minus}1}{center_dot}day{sup {minus}1}) was under sulfate-reducing conditions. Biotransformation of DBP at 10 C was significantly enhanced by the addition of 10 mM NaNO{sub 3} suggesting that both the addition of nitrate and high redox conditions favor its biotransformation in subsurface environments.

  17. Determination of low level methyl tert-butyl ether, ethyl tert-butyl ether and methyl tert-amyl ether in human urine by HS-SPME gas chromatography/mass spectrometry.

    PubMed

    Scibetta, Licia; Campo, Laura; Mercadante, Rosa; Foà, Vito; Fustinoni, Silvia

    2007-01-01

    Methyl tert-butyl ether (MTBE), ethyl tert-butyl ether (ETBE) and tert-amyl methyl ether (TAME) are oxygenated compounds added to gasoline to enhance octane rating and to improve combustion. They may be found as pollutants of living and working environments. In this work a robotized method for the quantification of low level MTBE, ETBE and TAME in human urine was developed and validated. The analytes were sampled in the headspace of urine by SPME in the presence of MTBE-d12 as internal standard. Different fibers were compared for their linearity and extraction efficiency: carboxen/polydimethylsiloxane, polydimethylsiloxane/divinylbenzene, and polydimethylsiloxane. The first, although highly efficient, was discarded due to deviation of linearity for competitive displacement, and the polydimethylsiloxane/divinylbenzene fiber was chosen instead. The analysis was performed by GC/MS operating in the electron impact mode. The method is very specific, with range of linearity 30-4600 ng L(-1), within- and between-run precision, as coefficient of variation, <22 and <16%, accuracy within 20% the theoretical level, and limit of detection of 6 ng L(-1) for all the analytes. The influence of the matrix on the quantification of these ethers was evaluated analysing the specimens of seven traffic policemen exposed to autovehicular emissions: using the calibration curve and the method of standard additions comparable levels of MTBE (68-528 ng L(-1)), ETBE (<6 ng L(-1)), and TAME (<6 ng L(-1)) were obtained.

  18. Cerebral and splenic infarctions after injection of N-butyl-2-cyanoacrylate in esophageal variceal bleeding.

    PubMed

    Myung, Dae-Seong; Chung, Cho-Yun; Park, Hyung-Chul; Kim, Jong-Sun; Cho, Sung-Bum; Lee, Wan-Sik; Choi, Sung-Kyu; Joo, Young-Eun

    2013-09-14

    Variceal bleeding is the most serious complication of portal hypertension, and it accounts for approximately one fifth to one third of all deaths in liver cirrhosis patients. Currently, endoscopic treatment remains the predominant method for the prevention and treatment of variceal bleeding. Endoscopic treatments include band ligation and injection sclerotherapy. Injection sclerotherapy with N-butyl-2-cyanoacrylate has been successfully used to treat variceal bleeding. Although injection sclerotherapy with N-butyl-2-cyanoacrylate provides effective treatment for variceal bleeding, injection of N-butyl-2-cyanoacrylate is associated with a variety of complications, including systemic embolization. Herein, we report a case of cerebral and splenic infarctions after the injection of N-butyl-2-cyanoacrylate to treat esophageal variceal bleeding.

  19. Enhanced cometabolic degradation of methyl tert-butyl ether by a Pseudomonas sp. strain grown on n-pentane

    NASA Astrophysics Data System (ADS)

    Li, S. S.; Wang, S.; Yan, W.

    2016-08-01

    When methyl tert-butyl ether (MTBE) is added as oxygenates it increases the octane number and decreases the release of nitric oxide from the incomplete combustion of reformulated gasoline. The extensive use of MTBE allowed it to be detectable as a pollutant in both ground-level and underground water worldwide. The present study focuses on the isolation and characterization of MTB-degrading microorganisms by cometabolism based on the results of growth on different carbon sources. It also focuses on the kinetic analysis and the continuous degradation of MTBE. A bacterial strain WL1 that can grow on both n-alkanes (C5-C8) and aromatics was isolated and named Pseudomonas sp. WL1 according to the 16S rDNA sequencing analysis. Strain WL1 could cometabolically degrade MTBE in the presence of n-alkanes with a desirable degradation rate. Diverse n-alkanes with different lengths of carbon chains showed significant influence on the degradation rate of MTBE and accumulation of tert-butyl alcohol (TBA). When strain WL1 cometabolically degraded MTBE in the presence of n-pentane, higher MTBE-degrading rate and lower TBA-accumulation were observed (Vmax = 38.1 nmol/min/mgprotei, Ks = 6.8 mmol/L). In the continuous degrading experiment, the removal efficiency of MTBE by Pseudomonas sp. WL1 did not show any obvious decrease after five subsequent additions.

  20. Tert-butyl benzoquinone: mechanism of biofilm eradication and potential for use as a topical antibiofilm agent

    PubMed Central

    Ooi, N.; Eady, E. A.; Cove, J. H.; O'Neill, A. J.

    2016-01-01

    Objectives Tert-butyl benzoquinone (TBBQ) is the oxidation product of tert-butyl hydroquinone (TBHQ), an antimicrobial food additive with >40 years of safe use. TBBQ displays potent activity against Staphylococcus aureus biofilms in vitro. Here, we report on studies to further explore the action of TBBQ on staphylococcal biofilms, and provide a preliminary preclinical assessment of its potential for use as a topical treatment for staphylococcal infections involving a biofilm component. Methods The antibacterial properties of TBBQ were assessed against staphylococci growing in planktonic culture and as biofilms in the Calgary Biofilm Device. Established assays were employed to measure the effects of TBBQ on biofilm structure and bacterial membranes, and to assess resistance potential. A living-skin equivalent was used to evaluate the effects of TBBQ on human skin. Results TBBQ eradicated biofilms of S. aureus and other staphylococcal species at concentrations ≤64 mg/L. In contrast to other redox-active agents exhibiting activity against biofilms, TBBQ did not cause substantial destructuring of the biofilm matrix; instead, the antibiofilm activity of the compound was attributed to its ability to kill slow- and non-growing cells via membrane perturbation. TBBQ acted synergistically with gentamicin, did not damage a living-skin equivalent following topical application and exhibited low resistance potential. Conclusions The ability of TBBQ to eradicate biofilms appears to result from its ability to kill bacteria regardless of growth state. Preliminary evaluation suggests that TBBQ represents a promising candidate for development as a topical antibiofilm agent. PMID:27121399

  1. Occupational exposures to new dry cleaning solvents: High-flashpoint hydrocarbons and butylal.

    PubMed

    Ceballos, Diana M; Whittaker, Stephen G; Lee, Eun Gyung; Roberts, Jennifer; Streicher, Robert; Nourian, Fariba; Gong, Wei; Broadwater, Kendra

    2016-10-01

    The dry cleaning industry is moving away from using perchloroethylene. Occupational exposures to two alternative dry cleaning solvents, butylal and high-flashpoint hydrocarbons, have not been well characterized. We evaluated four dry cleaning shops that used these alternative solvents. The shops were staffed by Korean- and Cantonese-speaking owners, and Korean-, Cantonese-, and Spanish-speaking employees. Because most workers had limited English proficiency we used language services in our evaluations. In two shops we collected personal and area air samples for butylal. We also collected air samples for formaldehyde and butanol, potential hydrolysis products of butylal. Because there are no occupational exposure limits for butylal, we assessed employee health risks using control banding tools. In the remaining two shops we collected personal and area air samples for high-flashpoint hydrocarbon solvents. In all shops the highest personal airborne exposures occurred when workers loaded and unloaded the dry cleaning machines and pressed dry cleaned fabrics. The air concentrations of formaldehyde and butanol in the butylal shops were well below occupational exposure limits. Likewise, the air concentrations of high-flashpoint hydrocarbons were also well below occupational exposure limits. However, we saw potential skin exposures to these chemicals. We provided recommendations on appropriate work practices and the selection and use of personal protective equipment. These recommendations were consistent with those derived using control banding tools for butylal. However, there is insufficient toxicological and health information to determine the safety of butylal in occupational settings. Independent evaluation of the toxicological properties of these alternative dry cleaning solvents, especially butylal, is urgently needed. PMID:27105306

  2. Methyl t-Butyl Ether Mineralization in Surface-Water Sediment Microcosms under Denitrifying Conditions

    USGS Publications Warehouse

    Bradley, P.M.; Chapelle, F.H.; Landmeyer, J.E.

    2001-01-01

    Mineralization of [U-14C] methyl t-butyl ether (MTBE) to 14CO2 without accumulation of t-butyl alcohol (TBA) was observed in surface-water sediment microcosms under denitrifying conditions. Methanogenic activity and limited transformation of MTBE to TBA were observed in the absence of denitrification. Results indicate that bed sediment microorganisms can effectively degrade MTBE to nontoxic products under denitrifying conditions.

  3. Kinetics of the partial oxidation of tert-butyl alcohol on a multicomponent catalyst

    SciTech Connect

    Tyurin, Yu.N.; Lebedeva, E.M.; Korchak, V.N.

    1988-10-01

    The process of partial oxidation of tert-butyl alcohol on a multicomponent catalyst consisting of compounds of molybdenum, cobalt, bismuth, iron, antimony, and potassium, was investigated under gradientless conditions in the 593-653 K temperature interval. The results indicate that the conversion of tert-butyl alcohol to oxidation products follows an oxidation-reduction mechanism. The kinetic equations that were found satisfactorily describe the experimental results.

  4. Enhanced astaxanthin production from Haematococcus pluvialis using butylated hydroxyanisole.

    PubMed

    Shang, Minmin; Ding, Wei; Zhao, Yongteng; Xu, Jun-Wei; Zhao, Peng; Li, Tao; Ma, Huixian; Yu, Xuya

    2016-10-20

    Haematococcus pluvialis is a promising natural source of high-value antioxidant astaxanthin under stress conditions. Biotic or abiotic elicitors are effective strategies for improving astaxanthin production in H. pluvialis. Butylated hydroxyanisole (BHA) was identified as an effective inducer for H. pluvialis LUGU. Under a treatment of 2mgL(-1) BHA (BHA2), astaxanthin content reached a maximum of 29.03mgg(-1) dry weight (DW) (2.03-fold of that in the control) after 12day of the mid-exponential growth phase. Subsequently, H. pluvialis LUGU was subjected to BHA2 at different growth phases because an appropriate time node for adding elicitors is vital for the entire production to succeed. As a result, the highest astaxanthin content (29.3mgg(-1) DW) was obtained in cells on day 14 (BHA2 14) of the late-exponential growth phase. Furthermore, the samples treated with BHA2 14 and the control group were compared in terms of the transcriptional expression of seven carotenogenesis genes, fatty acid composition, and total accumulated astaxanthin. All selected genes exhibited up-regulated expression profiles, with chy, crtO, and bkt exhibiting higher maximum transcriptional levels than the rest. Oleic acid content increased 33.15-fold, with acp, fad, and kas expression being enhanced on the day when astaxanthin was produced rapidly. PMID:27590093

  5. Cyhalofop-p-butyl mobility and distribution of residues in soil at various depths.

    PubMed

    Khare, Rishi Raj; Sondhia, Shobha

    2014-01-01

    This study was conducted to evaluate cyhalofop-p-butyl mobility in a sandy loam soil and subsequent distribution of residues at various depths under field conditions. Soil samples were taken from 0 to 150 cm depths at 3-90 d after rains in lysemeter of 1 and 2 m depths. Cyhalofop-p-butyl application at two rates and subsequent precipitation had a significant impact on soil, physico-chemical properties and herbicide mobility. Precipitation caused substantial mobility of cyhalofop-p-butyl in the soil and 1.1-7.6 μg L(-1) of cyhalofop-p-butyl was found in leachates. Cyhalofop-p-butyl residues in the leachates were probably due to preferential flow through the soil. Cyhalofop-p-butyl residues were detected in significant amounts from the soil up to 10 d, later, residues were found below the detection limit but its three transformation products viz., cyhalofop acid, diacid, and phenol were detected. PMID:24762176

  6. Application of the two-film model to the volatilization of acetone and t-butyl alcohol from water as a function of temperature

    USGS Publications Warehouse

    Rathbun, R.E.; Tai, D.Y.

    1988-01-01

    The two-film model is often used to describe the volatilization of organic substances from water. This model assumes uniformly mixed water and air phases separated by thin films of water and air in which mass transfer is by molecular diffusion. Mass-transfer coefficients for the films, commonly called film coefficients, are related through the Henry's law constant and the model equation to the overall mass-transfer coefficient for volatilization. The films are modeled as two resistances in series, resulting in additive resistances. The two-film model and the concept of additivity of resistances were applied to experimental data for acetone and t-butyl alcohol. Overall mass-transfer coefficients for the volatilization of acetone and t-butyl alcohol from water were measured in the laboratory in a stirred constant-temperature bath. Measurements were completed for six water temperatures, each at three water mixing conditions. Wind-speed was constant at about 0.1 meter per second for all experiments. Oxygen absorption coefficients were measured simultaneously with the measurement of the acetone and t-butyl alcohol mass-transfer coefficients. Gas-film coefficients for acetone, t-butyl alcohol, and water were determined by measuring the volatilization fluxes of the pure substances over a range of temperatures. Henry's law constants were estimated from data from the literature. The combination of high resistance in the gas film for solutes with low values of the Henry's law constants has not been studied previously. Calculation of the liquid-film coefficients for acetone and t-butyl alcohol from measured overall mass-transfer and gas-film coefficients, estimated Henry's law constants, and the two-film model equation resulted in physically unrealistic, negative liquid-film coefficients for most of the experiments at the medium and high water mixing conditions. An analysis of the two-film model equation showed that when the percentage resistance in the gas film is large and

  7. Thermal and photochemistry of tert-butyl iodide on ice films

    NASA Astrophysics Data System (ADS)

    Sohn, Youngku; Wei, Wei; White, John M.

    2008-08-01

    The thermal and photochemistry of tert-butyl iodide ( t-buI) on ice films grown on Cu(111) at 100 K were studied using time-of-flight (TOF) temperature programmed desorption (TPD) mass spectroscopy and X-ray photoelectron spectroscopy (XPS). The thermal reaction products include isobutane ( i-C 4H 10), isobutene ( i-C 4H 8) and minor t-butyl alcohol. In the rising edge of the water desorption at ˜145 K, the parent t-buI molecule desorbs from the ice as well as other thermal reaction products. Above the falling edge of the water desorption at ˜180 K, the reaction products and the parent molecule desorb from the Cu(111). For t-buI on bare Cu(111) dosed at 100 K, dominant i-C 4H 8, some i-C 4H 10 and tiny t-buI desorption peaks were observed. This indicates that t-buI promptly dissociates on Cu(111) to form C 4H 9 and chemisorbed I at 100 K. The C 4H 9 quickly rearranges, followed by C-H scission to form mainly i-C 4H 8, or abstracts H to form some i-C 4H 10. The I directly chemisorbs on the Cu(111), evidenced by I(3d) XPS peaks. On ice layer, the most dominant i-C 4H 10 desorption peak indicates that the C 4H 9 abstracts H from ice to form C 4H 10. For photoirradiation of t-buI on ice, we observed an enhanced t-buI dissociation followed by ejection of reaction products, evidenced by decrease in TPD and C(1s) XPS intensities. No ejection of I-containing molecules was observed. We attribute the t-buI dissociation to solvated electrons in ice. During photoirradiation, I radicals seem to diffuse into the bulk ice to chemisorb on Cu(111), plausibly due to self-diffusion of water. In addition, a preferential desorption of C 4H 10 and/or an enhanced reaction channel to i-C 4H 8 by photoirradiation is evidenced by a faster TPD decay rate of C 4H 10 with photoirradiation time. An increased i-C 4H 8 TPD peak at 113 K and an appearance of 2 amu desorption could indicate the enhanced channel to i-C 4H 8.

  8. Gene mdpC plays a regulatory role in the methyl-tert-butyl ether degradation pathway of Methylibium petroleiphilum strain PM1

    PubMed Central

    Joshi, Geetika; Schmidt, Radomir; Scow, Kate M.; Denison, Michael S.; Hristova, Krassimira R.

    2015-01-01

    Among the few bacteria known to utilize methyl tert-butyl ether (MTBE) as a sole carbon source, Methylibium petroleiphilum PM1 is a well-characterized organism with a sequenced genome; however, knowledge of the genetic regulation of its MTBE degradation pathway is limited. We investigated the role of a putative transcriptional activator gene, mdpC, in the induction of MTBE-degradation genes mdpA (encoding MTBE monooxygenase) and mdpJ (encoding tert-butyl alcohol hydroxylase) of strain PM1 in a gene-knockout mutant mdpC−. We also utilized quantitative reverse transcriptase PCR assays targeting genes mdpA, mdpJ and mdpC to determine the effects of the mutation on transcription of these genes. Our results indicate that gene mdpC is involved in the induction of both mdpA and mdpJ in response to MTBE and tert-butyl alcohol (TBA) exposure in PM1. An additional independent mechanism may be involved in the induction of mdpJ in the presence of TBA. PMID:25724531

  9. Biodegradation of Methyl tert-Butyl Ether by a Bacterial Pure Culture

    PubMed Central

    Hanson, Jessica R.; Ackerman, Corinne E.; Scow, Kate M.

    1999-01-01

    A bacterial strain, PM1, which is able to utilize methyl tert-butyl ether (MTBE) as its sole carbon and energy source, was isolated from a mixed microbial consortium in a compost biofilter capable of degrading MTBE. Initial linear rates of MTBE degradation by 2 × 106 cells ml−1 were 0.07, 1.17, and 3.56 μg ml−1 h−1 for initial concentrations of 5, 50, and 500 μg MTBE ml−1, respectively. When incubated with 20 μg of uniformly labeled [14C]MTBE ml−1, strain PM1 converted 46% to 14CO2 and 19% to 14C-labeled cells within 120 h. This yield is consistent with the measurement of protein accumulation at different MTBE concentrations from which was estimated a biomass yield of 0.18 mg of cells mg MTBE−1. Strain PM1 was inoculated into sediment core material collected from a contaminated groundwater plume at Port Hueneme, California, in which there was no evidence of MTBE degradation. Strain PM1 readily degraded 20 μg of MTBE ml−1 added to the core material. The rate of MTBE removal increased with additional inputs of 20 μg of MTBE ml−1. These results suggest that PM1 has potential for use in the remediation of MTBE-contaminated environments. PMID:10543787

  10. Microscopy of thin polymer blend films of polystyrene and poly-n-butyl-methacrylate

    NASA Astrophysics Data System (ADS)

    Schmitt, T.; Guttmann, P.; Schmidt, O.; Müller-Buschbaum, P.; Stamm, M.; Schönhense, G.; Schmahl, G.

    2000-05-01

    The structure of thin polymer blend films of polystyrene (PS) and poly-n-butyl-methacrylate (PnBMA) was examined with Transmission X-ray Microscopy (TXM), Scanning Force Microscopy (SFM), X-Ray Photoemission Electron Microscopy (X-PEEM) and Optical Microscopy (OM). Thin films were prepared by spin casting of a toluene solution of the polymer mixture onto silicon wafers retaining the native oxide. Depending on blend composition and annealing conditions smooth films with and without holes or films with well pronounced surface features (ribbons or islands) were produced. By TXM measurements a high lateral resolution study of the as cast and the annealed polymer blend samples was performed. The contrast in TXM is due to different absorption of x-radiation of the used polymers and due to variation in thickness. With X-PEEM the lateral distribution of the two polymers near the surface was mapped by employing the characteristic Near Edge X-ray Absorption Fine Structure (NEXAFS) spectra of the polymers. The TXM technique is a microscopic method integrating over the total film thickness, whereas the X-PEEM technique is a highly surface sensitive method. TXM and X-PEEM are therefore complementary methods which provide important information on the structure of thin polymer blend films additional to the standard techniques SFM and OM.

  11. Environmental behavior and fate of methyl tert-butyl ether (MTBE)

    USGS Publications Warehouse

    Squillace, Paul J.; Pankow, James F.; Korte, Nic E.; Zogorski, John S.

    1996-01-01

    When gasoline that has been oxygenated with methyl tert-butyl ether (MTBE) comes in contact with water, large amounts of MTBE can dissolve; at 25 degrees Celsius the water solubility of MTBE is about 5,000 milligrams per liter for a gasoline that is 10 percent MTBE by weight. In contrast, for a nonoxygenated gasoline, the total hydrocarbon solubility in water is typically about 120 milligrams per liter. MTBE sorbs only weakly to soil and aquifer materials; therefore, sorption will not significantly retard MTBE's transport by ground water. In addition, MTBE generally resists degradation in ground water. The half-life of MTBE in the atmosphere can be as short as 3 days in a regional airshed. MTBE in the air tends to partition into atmospheric water, including precipitation. However, washout of gas-phase MTBE by precipitation would not, by itself, greatly alter the gas-phase concentration of the compound in the air. The partitioning of MTBE to precipitation is nevertheless strong enough to allow for up to 3 micrograms per liter or more inputs of MTBE to surface and ground water.

  12. Bioremediation of endocrine disruptor di-n-butyl phthalate ester by Deinococcus radiodurans and Pseudomonas stutzeri.

    PubMed

    Liao, Chien-Sen; Chen, Lung-Chieh; Chen, Bing-Sheng; Lin, Sin-Hsien

    2010-01-01

    Di-n-butyl phthalate (DBP) is a group of phthalate esters (PAEs) that are widely used in cosmetics, perfumes, and plasticizers. Due to its high production and application figures, DBP is commonly found in wastewater, sewage sludge, and aquatic environments. It has been classified as suspected endocrine disruptors by most countries. In this study, we isolated two DBP degradable strains from activated sludge. The strains were identified with their 16S rRNA as Deinococcus radiodurans and Pseudomonas stutzeri. We constructed the optimal condition of DBP degradation by using different kinds of incubation factors such as temperature, initial pH, yeast extract and surfactants. The optimal conditions of DBP degradation for these two strains are: 30 degrees C, pH 7.5 and static culture. Besides, addition of 0.23 mM of Triton X-100 could enhance the DBP degradation for D. radiodurans. In the end, we amended these two strains into the origin activated sludge and analyzed the whole microbial community structure of mixed cultures by PCR-DGGE technique. The result showed that only D. radiodurans could survive in the activated sludge after 7d of incubation. Based on this work, we hope that these findings could provide some useful information for applying the bioremediation of DBP in our environment.

  13. Biodegradation of Di-n-Butyl Phthalate by a Newly Isolated Halotolerant Sphingobium sp.

    PubMed Central

    Jin, Decai; Kong, Xiao; Cui, Bingjian; Bai, Zhihui; Zhang, Hongxun

    2013-01-01

    A Gram-negative strain (TJ) capable of growing aerobically on mixed phthalate esters (PAEs) as the sole carbon and energy source was isolated from the Haihe estuary, Tianjin, China. It was identified as belonging to the Sphingobium genus on the basis of morphological and physiological characteristics and 16S rRNA and gyrb gene sequencing. The batch tests for biodegradation of di-n-butyl phthalate (DBP) by the Sphingobium sp. TJ showed that the optimum conditions were 30 °C, pH 7.0, and the absence of NaCl. Stain TJ could tolerate up to 4% NaCl in minimal salt medium supplemented with DBP, although the DBP degradation rates slowed as NaCl concentration increased. In addition, substrate tests showed that strain TJ could utilize shorter side-chained PAEs, such as dimethyl phthalate and diethyl phthalate, but could not metabolize long-chained PAEs, such as di-n-octyl phthalate, diisooctyl phthalate, and di-(2-ethyl-hexyl) phthalate. To our knowledge, this is the first report on the biodegradation characteristics of DBP by a member of the Sphingobium genus. PMID:24336064

  14. Preparation of cellulose/polyvinyl alcohol biocomposite films using 1-n-butyl-3-methylimidazolium chloride.

    PubMed

    Abdulkhani, Ali; Hojati Marvast, Ebrahim; Ashori, Alireza; Hamzeh, Yahya; Karimi, Ali Naghi

    2013-11-01

    This study has been focused on developing cellulose/polyvinyl alcohol (PVA), a biocomposite film, pretreated with 1-n-butyl-3-methylimidazolium chloride ([bmim]Cl). The dissolved polymers were blended and their biocomposite films including cellulose and cellulose/PVA were prepared. The effect of PVA composition with cellulose was evaluated by comparing the physical, mechanical, chemical and thermal characteristics of produced films with neat cellulosic film. The results showed that the ionic liquid had a great capability in dissolving the polymers. Furthermore, in composition of the raw cellulose some chemical bonds were incorporated between the two components. Water uptake, thickness swelling and water vapor permeability of blend films were increased comparing to cellulosic film. Mechanical strength and Young's modulus of the films made of cellulose/PVA were decreased while the strain at break was increased. The optical transparency and thermal properties of the blend films were almost the same as neat cellulosic film. This work demonstrated a promising route for the preparation of biodegradable green composites. In addition, this biocomposite film is composed of sustainable biodegradable resources, which is suitable for release to the environment. The biocomposite films showed good optical transparency, thermal stabilities properties.

  15. Molecular dynamics simulation of tri-n-butyl-phosphate liquid: a force field comparative study.

    PubMed

    Cui, Shengting; de Almeida, Valmor F; Hay, Benjamin P; Ye, Xianggui; Khomami, Bamin

    2012-01-12

    Molecular dynamics (MD) simulations were conducted to compare the performance of four force fields in predicting thermophysical properties of tri-n-butyl-phosphate (TBP) in the liquid phase. The intramolecular force parameters used were from the Assisted Model Building with Energy Refinement (AMBER) force field model. The van der Waals parameters were based on either the AMBER or the Optimized Potential for Liquid Simulation (OPLS) force fields. The atomic partial charges were either assigned by performing quantum chemistry calculations or utilized previously published data, and were scaled to approximate the average experimental value of the electric dipole moment. Canonical ensemble computations based on the aforementioned parameters were performed near atmospheric pressure and temperature to obtain the electric dipole moment, mass density, and self-diffusion coefficient. In addition, the microscopic structure of the liquid was characterized via pair correlation functions between selected atoms. It has been demonstrated that the electric dipole moment can be approximated within 1% of the average experimental value by virtue of scaled atomic partial charges. The liquid mass density can be predicted within 0.5-1% of its experimentally determined value when using the corresponding charge scaling. However, in all cases, the predicted self-diffusion coefficient is significantly smaller than a commonly quoted experimental measurement; this result is qualified by the fact that the uncertainty of the experimental value was not available. PMID:22126596

  16. Ethyl-tertiary-butyl-ether (ETBE) as an aviation fuel: Eleventh international symposium on alcohol fuels

    SciTech Connect

    Maben, G.D.; Shauck, M.E.; Zanin, M.G.

    1996-12-31

    This paper discusses the preliminary flight testing of an aircraft using neat burning ethyl-tertiary-butyl-ether (ETBE) as a fuel. No additional changes were made to the fuel delivery systems which had previously been modified to provide the higher fuel flow rates required to operate the engine on neat ethanol. Air-fuel ratios were manually adjusted with the mixture control. This system allows the pilot to adjust the mixture to compensate for changes in air density caused by altitude, pressure and temperature. The engine was instrumented to measure exhaust gas temperatures (EGT), cylinder head temperatures (CHT), and fuel flows, while the standard aircraft instruments were used to collect aircraft performance data. Baseline engine data for ETBE and Avgas are compared. Preliminary data indicates the technical and economic feasibility of using ETBE as an aviation fuel for the piston engine fleet. Furthermore, the energy density of ETBE qualifies it as a candidate for a turbine engine fuel of which 16.2 billion gallons are used in the US each year.

  17. Potential ecotoxicological implication of methyl tert-butyl ether (MTBE) spills in the environment.

    PubMed

    Bonjar, G H Shahidi

    2004-10-01

    Streptomyceticidal activity of Methyl tert-butyl ether (MTBE) elucidated for the first time. Adverse effect of MTBE, the gasoline additive, against 11 soil inhabitant Streptomyces spp. isolates was investigated. MTBE, an octane enhancer is added to gasoline to reduce atmospheric concentrations of carbon monoxide and ozone. It contaminates soil and groundwater by fuel leaks and spills. Streptomyces spp. are of the major contributors to the biological buffering of soils by exerting beneficial and antagonistic activity against wide range of bacteria and fungi. To evaluate anti-streptomycetidal activity of MTBE, it was tested against 11 soil isolates of Streptomyces isolates and also a plant-root bacterial pathogen, Erwinia carotovora and a plant-root fungal pathogen, Fusarium solani. MTBE did not reveal any growth inhibitory activity against E. carotovora and F. solani, but showed strong inhibitory effect against Streptomyces isolates. The Minimum Inhibitory Concentration (MIC) on Streptomyces isolates was 1/800 of the original MTBE. Fuel leaks and spills have the potential to suppress or eliminate the Streptomyces role in the soil causing alteration in the balance of soil micro flora. This change can promote the domination of microorganisms with adverse biological or ecotoxicological effects.

  18. Biodegradation of methyl tert-butyl ether by a bacterial pure culture.

    PubMed

    Hanson, J R; Ackerman, C E; Scow, K M

    1999-11-01

    A bacterial strain, PM1, which is able to utilize methyl tert-butyl ether (MTBE) as its sole carbon and energy source, was isolated from a mixed microbial consortium in a compost biofilter capable of degrading MTBE. Initial linear rates of MTBE degradation by 2 x 10(6) cells ml(-1) were 0.07, 1.17, and 3.56 microg ml(-1) h(-1) for initial concentrations of 5, 50, and 500 microg MTBE ml(-1), respectively. When incubated with 20 microg of uniformly labeled [(14)C]MTBE ml(-1), strain PM1 converted 46% to (14)CO(2) and 19% to (14)C-labeled cells within 120 h. This yield is consistent with the measurement of protein accumulation at different MTBE concentrations from which was estimated a biomass yield of 0.18 mg of cells mg MTBE(-1). Strain PM1 was inoculated into sediment core material collected from a contaminated groundwater plume at Port Hueneme, California, in which there was no evidence of MTBE degradation. Strain PM1 readily degraded 20 microg of MTBE ml(-1) added to the core material. The rate of MTBE removal increased with additional inputs of 20 microg of MTBE ml(-1). These results suggest that PM1 has potential for use in the remediation of MTBE-contaminated environments.

  19. Transcatheter Embolotherapy with N-Butyl Cyanoacrylate for Ectopic Varices

    SciTech Connect

    Choi, Jin Woo; Kim, Hyo-Cheol Jae, Hwan Jun Jung, Hyun-Seok; Hur, Saebeom; Lee, Myungsu; Chung, Jin Wook

    2015-04-15

    PurposeTo address technical feasibility and clinical outcome of transcatheter embolotherapy with N-butyl cyanoacrylate (NBCA) for bleeding ectopic varices.MethodsThe institutional review board approved this retrospective study and waived informed consent. From January 2004 to June 2013, a total of 12 consecutive patients received transcatheter embolotherapy using NBCA for bleeding ectopic varices in our institute. Clinical and radiologic features of the endovascular procedures were comprehensively reviewed.ResultsPreprocedural computed tomography images revealed ectopic varices in the jejunum (n = 7), stoma (n = 2), rectum (n = 2), and duodenum (n = 1). The 12 procedures consisted of solitary embolotherapy (n = 8) and embolotherapy with portal decompression (main portal vein stenting in 3, transjugular intrahepatic portosystemic shunt in 1). With regard to vascular access, percutaneous transhepatic access (n = 7), transsplenic access (n = 4), and transjugular intrahepatic portosystemic shunt tract (n = 1) were used. There was no failure in either the embolotherapy or the vascular accesses (technical success rate, 100 %). Two patients died within 1 month from the procedure from preexisting fatal medical conditions. Only one patient, with a large varix that had been partially embolized by using coils and NBCA, underwent rebleeding 5.5 months after the procedure. The patient was retreated with NBCA and did not undergo any bleeding afterward for a follow-up period of 2.5 months. The remaining nine patients did not experience rebleeding during the follow-up periods (range 1.5–33.2 months).ConclusionTranscatheter embolotherapy using NBCA can be a useful option for bleeding ectopic varices.

  20. Effects of simulant mixed waste on EPDM and butyl rubber

    SciTech Connect

    Nigrey, P.J.; Dickens, T.G.

    1997-11-01

    The authors have developed a Chemical Compatibility Testing Program for the evaluation of plastic packaging components which may be used in transporting mixed waste forms. In this program, they have screened 10 plastic materials in four liquid mixed waste simulants. These plastics were butadiene-acrylonitrile copolymer (Nitrile) rubber, cross-linked polyethylene, epichlorohydrin rubber, ethylene-propylene (EPDM) rubber, fluorocarbons (Viton and Kel-F{trademark}), polytetrafluoro-ethylene (Teflon), high-density polyethylene, isobutylene-isoprene copolymer (Butyl) rubber, polypropylene, and styrene-butadiene (SBR) rubber. The selected simulant mixed wastes were (1) an aqueous alkaline mixture of sodium nitrate and sodium nitrite; (2) a chlorinated hydrocarbon mixture; (3) a simulant liquid scintillation fluid; and (4) a mixture of ketones. The screening testing protocol involved exposing the respective materials to approximately 3 kGy of gamma radiation followed by 14-day exposures to the waste simulants at 60 C. The rubber materials or elastomers were tested using Vapor Transport Rate measurements while the liner materials were tested using specific gravity as a metric. The authors have developed a chemical compatibility program for the evaluation of plastic packaging components which may be incorporated in packaging for transporting mixed waste forms. From the data analyses performed to date, they have identified the thermoplastic, polychlorotrifluoroethylene, as having the greatest chemical compatibility after having been exposed to gamma radiation followed by exposure to the Hanford Tank simulant mixed waste. The most striking observation from this study was the poor performance of polytetrafluoroethylene under these conditions. In the evaluation of the two elastomeric materials they have concluded that while both materials exhibit remarkable resistance to these environmental conditions, EPDM has a greater resistance to this corrosive simulant mixed waste.

  1. Comparison and Characterisation of Regenerated Chitosan from 1-Butyl-3-methylimidazolium Chloride and Chitosan from Crab Shells.

    PubMed

    Islam, Saniyat; Arnold, Lyndon; Padhye, Rajiv

    2015-01-01

    Chitosan is a biopolymer derived from chitin which is naturally occurring in the exoskeleton of crustaceans. This paper reports dissolution and regeneration of chitosan by directly dissolving in an ionic liquid solvent, 1-butyl-3-methylimidazolium chloride (BMIMCl). This will provide an ideal platform to solubilise these kinds of polymers to achieve the dissolution. The current study dissolved chitosan from crab shell utilising BMIMCl as a solvent and characterised the resultant regenerated polymer. The regenerated chitosan showed increased hydrogen bonding when characterised by Fourier transform infrared (FTIR) spectral analysis. In addition, the study also compared the characteristics of regenerated and generic chitosan. The regenerated chitosan was also evaluated for antimicrobial properties and showed to possess antibacterial features similar to the commercial grade. This method can be utilised in future for blending of polymers with chitosan in a dissolved phase.

  2. Comparison and Characterisation of Regenerated Chitosan from 1-Butyl-3-methylimidazolium Chloride and Chitosan from Crab Shells

    PubMed Central

    Arnold, Lyndon

    2015-01-01

    Chitosan is a biopolymer derived from chitin which is naturally occurring in the exoskeleton of crustaceans. This paper reports dissolution and regeneration of chitosan by directly dissolving in an ionic liquid solvent, 1-butyl-3-methylimidazolium chloride (BMIMCl). This will provide an ideal platform to solubilise these kinds of polymers to achieve the dissolution. The current study dissolved chitosan from crab shell utilising BMIMCl as a solvent and characterised the resultant regenerated polymer. The regenerated chitosan showed increased hydrogen bonding when characterised by Fourier transform infrared (FTIR) spectral analysis. In addition, the study also compared the characteristics of regenerated and generic chitosan. The regenerated chitosan was also evaluated for antimicrobial properties and showed to possess antibacterial features similar to the commercial grade. This method can be utilised in future for blending of polymers with chitosan in a dissolved phase. PMID:26090452

  3. Understanding the large solubility of lidocaine in 1-n-butyl-3-methylimidazolium based ionic liquids using molecular simulation

    NASA Astrophysics Data System (ADS)

    Ley, Ryan T.; Paluch, Andrew S.

    2016-02-01

    Room temperature ionic liquids have been proposed as replacement solvents in a wide range of industrial separation processes. Here, we focus on the use of ionic liquids as solvents for the pharmaceutical compound lidocaine. We show that the solubility of lidocaine in seven common 1-n-butyl-3-methylimidazolium based ionic liquids is greatly enhanced relative to water. The predicted solubility is greatest in [BMIM]+[CH3CO2]-, which we find results from favorable hydrogen bonding between the lidocaine amine hydrogen and the [CH3CO2]- oxygen, favorable electrostatic interactions between the lidocaine amide oxygen with the [BMIM]+ aromatic ring hydrogens, while lidocaine does not interfere with the association of [BMIM]+ with [CH3CO2]-. Additionally, by removing functional groups from the lidocaine scaffold while maintaining the important amide group, we found that as the van der Waals volume increases, solubility in [BMIM]+[CH3CO2]- relative to water increases.

  4. Arbuscular mycorrhizal fungi in a wetland constructed for benzene-, methyl tert-butyl ether- and ammonia-contaminated groundwater bioremediation

    PubMed Central

    Fester, Thomas

    2013-01-01

    Arbuscular mycorrhizal fungi (AMF), which are present in most natural environments, have demonstrated capacity to promote biodegradation of organic pollutants in the greenhouse. However, it is not certain whether AMF can spontaneously establish in phytoremediation systems constructed to decontaminate groundwater, because of the unusual conditions during the construction and operation of such systems. To assess this possibility, root samples from a wetland constructed for the phytoremediation of groundwater contaminated with benzene, methyl tert-butyl ether and ammonia were analysed. Substantial AMF colonization was observed in plant roots sampled close to the inlet of a basin filled with fine gravel and planted with Phragmites australis. In addition, analysis of a fragment of the nuclear large ribosomal subunit, amplified by nested PCR, revealed the presence of AMF molecular operational taxonomic units closely related to Funneliformis mosseae and Rhizophagus irregularis in the samples. These findings demonstrate the capacity of generalist AMF strains to establish spontaneously, rapidly and extensively in groundwater bioremediation technical installations. PMID:22846140

  5. Understanding the large solubility of lidocaine in 1-n-butyl-3-methylimidazolium based ionic liquids using molecular simulation.

    PubMed

    Ley, Ryan T; Paluch, Andrew S

    2016-02-28

    Room temperature ionic liquids have been proposed as replacement solvents in a wide range of industrial separation processes. Here, we focus on the use of ionic liquids as solvents for the pharmaceutical compound lidocaine. We show that the solubility of lidocaine in seven common 1-n-butyl-3-methylimidazolium based ionic liquids is greatly enhanced relative to water. The predicted solubility is greatest in [BMIM](+)[CH3CO2](-), which we find results from favorable hydrogen bonding between the lidocaine amine hydrogen and the [CH3CO2](-) oxygen, favorable electrostatic interactions between the lidocaine amide oxygen with the [BMIM](+) aromatic ring hydrogens, while lidocaine does not interfere with the association of [BMIM](+) with [CH3CO2](-). Additionally, by removing functional groups from the lidocaine scaffold while maintaining the important amide group, we found that as the van der Waals volume increases, solubility in [BMIM](+)[CH3CO2](-) relative to water increases. PMID:26931706

  6. Simultaneous Clostridial fermentation, lipase-catalyzed esterification, and ester extraction to enrich diesel with butyl butyrate.

    PubMed

    van den Berg, Corjan; Heeres, Arjan S; van der Wielen, Luuk A M; Straathof, Adrie J J

    2013-01-01

    The recovery of 1-butanol from fermentation broth is energy-intensive since typical concentrations in fermentation broth are below 20 g L(-1). To prevent butanol inhibition and high downstream processing costs, we aimed at producing butyl esters instead of 1-butanol. It is shown that it is possible to perform simultaneously clostridial fermentation, esterification of the formed butanol to butyl butyrate, and extraction of this ester by hexadecane. The very high partition coefficient of butyl butyrate pulls the esterification towards the product side even at fermentation pH and relatively low butanol concentrations. The hexadecane extractant is a model diesel compound and is nontoxic to the cells. If butyl butyrate enriched diesel can directly be used as car fuel, no product recovery is required. A proof-of-principle experiment for the one-pot bio-ester production from glucose led to 5 g L(-1) butyl butyrate in the hexadecane phase. The principle may be extended to a wide range of esters, especially to longer chain ones.

  7. Human gallbladder morphology after gallstone dissolution with methyl tert-butyl ether.

    PubMed

    vanSonnenberg, E; Zakko, S; Hofmann, A F; D'Agostino, H B; Jinich, H; Hoyt, D B; Miyai, K; Ramsby, G; Moossa, A R

    1991-06-01

    The effects of methyl tert-butyl ether exposure on the human gallbladder in five patients who were treated for gallstones by contact dissolution is described. Two patients underwent cholecystectomy within 1 week of methyl tert-butyl ether treatment, one patient 2 weeks after, another 10 weeks after, and one 12 weeks after. Indications for cholecystectomy were bilirubinate stones (resistant to methyl tert-butyl ether), catheter dislodgement, bile leakage, and gallstone recurrence (2 patients). Gallstones were dissolved completely in three patients, there was approximately 50% stone reduction in one patient, and no dissolution occurred in the fifth patient. Each gallbladder was examined grossly and histologically. Electron microscopic evaluation was performed in one cases. Typical inflammatory findings of chronic cholecystitis were observed in each gallbladder and were most conspicuous in the submucosa; the mucosal and serosal surfaces were intact. Mild acute inflammatory changes were noted in the submucosa in the two patients with the shortest interval between methyl tert-butyl ether administration and cholecystectomy. There were no ulcerations in the mucosa and no unusual wall thickening or fibrosis in any patient. These observations support the safety of methyl tert-butyl ether perfusion in the human gallbladder; the mild acute changes may be a transient and reversible phenomenon.

  8. Simultaneous Clostridial fermentation, lipase-catalyzed esterification, and ester extraction to enrich diesel with butyl butyrate.

    PubMed

    van den Berg, Corjan; Heeres, Arjan S; van der Wielen, Luuk A M; Straathof, Adrie J J

    2013-01-01

    The recovery of 1-butanol from fermentation broth is energy-intensive since typical concentrations in fermentation broth are below 20 g L(-1). To prevent butanol inhibition and high downstream processing costs, we aimed at producing butyl esters instead of 1-butanol. It is shown that it is possible to perform simultaneously clostridial fermentation, esterification of the formed butanol to butyl butyrate, and extraction of this ester by hexadecane. The very high partition coefficient of butyl butyrate pulls the esterification towards the product side even at fermentation pH and relatively low butanol concentrations. The hexadecane extractant is a model diesel compound and is nontoxic to the cells. If butyl butyrate enriched diesel can directly be used as car fuel, no product recovery is required. A proof-of-principle experiment for the one-pot bio-ester production from glucose led to 5 g L(-1) butyl butyrate in the hexadecane phase. The principle may be extended to a wide range of esters, especially to longer chain ones. PMID:22833369

  9. Radiation-induced degradation of butyl rubber vulcanized by three different crosslinking systems

    NASA Astrophysics Data System (ADS)

    Scagliusi, Sandra R.; Cardoso, Elisabeth C. L.; Lugao, Ademar B.

    2012-08-01

    Butyl rubber (IIR) is an isobutylene/isoprene copolymer and is provided with good properties including low permeability to gases, good thermal stability and high resistance to oxygen and ozone action, among others. It is well known that the major effect of ionizing radiations on butyl rubber is chain scission accompanied with a significant reduction in molar mass. This work aimed to study the effects of gamma radiation on the properties of butyl rubbers vulcanized by three different curing systems, such as, the ones based on sulfur, sulfur donor and phenolic resin to identify which curing system is the most stable under irradiation. The butyl rubber vulcanized by three different systems was gamma irradiated with doses of 25 kGy, 50 kGy, 100 kGy, 150 kGy and 200 kGy. Irradiated and non-irradiated samples were characterized by the following techniques: tensile, elongation and hardness. It was observed that doses higher than 150 kGy practically destroy the assessed properties for all butyl compounds, irrespective of the vulcanization system used; however compounds cured with phenolic resin showed a decrease in properties proportional to the dose.

  10. Hydrogen bonded rings, chains and lassos: the case of t-butyl alcohol clusters

    NASA Astrophysics Data System (ADS)

    Zimmermann, D.; Häber, Th.; Schaal, H.; Suhm, M. A.

    Infrared OH stretching spectra of hydrogen bonded 2-methyl-propan-2-ol (t-butyl alcohol) clusters are investigated by ragout-jet FTIR spectroscopy. A spectral difference technique is used to discriminate approximately between neighbouring cluster sizes. Dimers, trimers and cyclic tetramers can be detected along with larger clusters, which exhibit a surprisingly structured vibrational fingerprint. Comparison is made to the spectra of related alcohols and to energetic and harmonic vibrational predictions from electronic structure calculations. The experimentally observed 32% increase in OH stretching wavenumber shift from methanol dimer to t-butyl alcohol dimer is reproduced at the HF/3-21G level (+ 33%). It is also qualitatively correct at the MP2/6-31+ G* level (+ 15%), whereas it has the wrong sign at the B3LYP/6-31+ G* level (-5%) and is negligible at the HF/6-31+ G* level, disregarding anharmonic effects. The cyclic tetramer of t-butyl alcohol is found to be particularly stable due to a favourable up-down alternation of the bulky t-butyl groups. Beyond the t-butyl alcohol tetramer, lasso structures are found to be energetically competitive with simple ring structures. A many-body decomposition shows that this is due to a reduced cooperativity in the sterically hindered pentamer ring. The resulting thermodynamic and kinetic relevance of cyclic tetramers is discussed.

  11. The electrospinning of the copolymer of styrene and butyl acrylate for its application as oil absorbent.

    PubMed

    Xu, Naiku; Cao, Jipeng; Lu, Yuyao

    2016-01-01

    Electrospun polystyrene materials have been employed as oil absorbents, but they have visible drawbacks such as poor strength at low temperature and unreliable integrity because of brittleness and insufficient cohesive force among fibers. Butyl acrylate can polymerize into flexible chains, and its polymer can be used as elastomer and adhesive material. Thereby it is possible to obtain the material that has better performance in comparison with electrospun polystyrene material through the electrospinning of the copolymer of styrene and butyl acrylate. In this work, a polymer was synthesized through suspension polymerization by using styrene and butyl acrylate as comonomers. The synthesis of the copolymer of styrene and butyl acrylate was verified through dissolution and hydrolysis experimental data; as well through nuclear magnetic resonance spectrometry. The viscous flow activation energy of the solution consisting of copolymer and N, N-dimethylformamide was determined via viscosity method and then adopted to establish the entanglement characteristics of butyl acrylate's chain segments. Finally, in order to electrospin the copolymer solution into fibrous membrane, the effects of monomer feed ratio and spinning parameters were investigated. The prepared fibrous membrane was found to have a potential use as oil absorbent. PMID:27610302

  12. Methyl tert-butyl ether biodegradation by indigenous aquifer microorganisms under natural and artificial oxic conditions

    USGS Publications Warehouse

    Landmeyer, J.E.; Chapelle, F.H.; Herlong, H.H.; Bradley, P.M.

    2001-01-01

    Microbial communities indigenous to a shallow groundwater system near Beaufort, SC, degraded milligram per liter concentrations of methyl tert-butyl ether (MTBE) under natural and artificial oxic conditions. Significant MTBE biodegradation was observed where anoxic, MTBE-contaminated groundwater discharged to a concrete-lined ditch. In the anoxic groundwater adjacent to the ditch, concentrations of MTBE were > 1 mg/L. Where groundwater discharge occurs, dissolved oxygen (DO) concentrations beneath the ditch exceeded 1.0 mg/L to a depth of 1.5 m, and MTBE concentrations decreased to <1 ??g/L prior to discharge. MTBE mass flux calculations indicate that 96% of MTBE mass loss occurs in the relatively small oxic zone prior to discharge. Samples of a natural microbial biofilm present in the oxic zone beneath the ditch completely degraded [U-14C]MTBE to [14C]CO2 in laboratory liquid culture studies, with no accumulation of intermediate compounds. Upgradient of the ditch in the anoxic, MTBE and BTEX-contaminated aquifer, addition of a soluble oxygen release compound resulted in oxic conditions and rapid MTBE biodegradation by indigenous microorganisms. In an observation well located closest to the oxygen addition area, DO concentrations increased from 0.4 to 12 mg/L in <60 days and MTBE concentrations decreased from 20 to 3 mg/L. In the same time period at a downgradient observation well, DO increased from <0.2 to 2 mg/L and MTBE concentrations decreased from 30 to <5 mg/L. These results indicate that microorganisms indigenous to the groundwater system at this site can degrade milligram per liter concentrations of MTBE under natural and artificial oxic conditions.

  13. Methyl tert-butyl ether biodegradation by indigenous aquifer microorganisms under natural and artificial oxic conditions.

    PubMed

    Landmeyer, J E; Chapelle, F H; Herlong, H H; Bradley, P M

    2001-03-15

    Microbial communities indigenous to a shallow groundwater system near Beaufort, SC, degraded milligram per liter concentrations of methyl tert-butyl ether (MTBE) under natural and artificial oxic conditions. Significant MTBE biodegradation was observed where anoxic, MTBE-contaminated groundwater discharged to a concrete-lined ditch. In the anoxic groundwater adjacent to the ditch, concentrations of MTBE were > 1 mg/L. Where groundwater discharge occurs, dissolved oxygen (DO) concentrations beneath the ditch exceeded 1.0 mg/Lto a depth of 1.5 m, and MTBE concentrations decreased to <1 microg/L prior to discharge. MTBE mass flux calculations indicate that 96% of MTBE mass loss occurs in the relatively small oxic zone prior to discharge. Samples of a natural microbial biofilm present in the oxic zone beneath the ditch completely degraded [U-14C]MTBE to [14C]CO2 in laboratory liquid culture studies, with no accumulation of intermediate compounds. Upgradient of the ditch in the anoxic, MTBE- and BTEX-contaminated aquifer, addition of a soluble oxygen release compound resulted in oxic conditions and rapid MTBE biodegradation by indigenous microorganisms. In an observation well located closest to the oxygen addition area, DO concentrations increased from 0.4 to 12 mg/L in <60 days and MTBE concentrations decreased from 20 to 3 mg/L. In the same time period at a downgradient observation well, DO increased from <0.2 to 2 mg/L and MTBE concentrations decreased from 30 to <5 mg/L. These results indicate that microorganisms indigenous to the groundwater system at this site can degrade milligram per liter concentrations of MTBE under natural and artificial oxic conditions. PMID:11347923

  14. Miniemulsion polymerizations of n-butyl cyanoacrylate via two routes: towards a control of particle degradation.

    PubMed

    Hansali, F; Poisson, G; Wu, M; Bendedouch, D; Marie, E

    2011-11-01

    This study aimed at determining the influence of the mechanism of polymerization on the molar mass and degradation of poly(n-butyl cyanoacrylate) (PBCA) nanoparticles obtained by miniemulsion polymerization. Therefore, nanoparticles of poly(n-butyl cyanoacrylate) were synthesized via radical and/or anionic miniemulsion polymerization stabilized by Brij®78, a POE based surfactant. Polymerization conditions had little influence on the final diameter while it severely affected the final molar masses of PBCA. An increase of the temperature and of the pH of the continuous phase led to higher molar masses. A further increase was observed when a radical initiator was added in the monomer. The evolution of the molar mass of the synthesized poly(n-butyl cyanoacrylate) was followed as a function of time at pH 7.4 by Size Exclusion Chromatography. As expected, the degradation kinetics strongly depended on the polymerization mechanism (anionic or radical).

  15. Method for determination of methyl tert-butyl ether and its degradation products in water

    USGS Publications Warehouse

    Church, C.D.; Isabelle, L.M.; Pankow, J.F.; Rose, D.L.; Tratnyek, P.G.

    1997-01-01

    An analytical method is described that can detect the major alkyl ether compounds that are used as gasoline oxygenates (methyl tert-butyl ether, MTBE; ethyl tert-butyl ether, ETBE; and tert-amyl methyl ether, TAME) and their most characteristic degradation products (tert-butyl alcohol, TBA; tert-butyl formate, TBF; and tert-amyl alcohol, TAA) in water at sub-ppb concentrations. The new method involves gas chromatography (GC) with direct aqueous injection (DAI) onto a polar column via a splitless injector, coupled with detection by mass spectrometry (MS). DAI-GC/MS gives excellent agreement with conventional purge-and-trap methods for MTBE over a wide range of environmentally relevant concentrations. The new method can also give simultaneous identification of polar compounds that might occur as degradation products of gasoline oxygenates, such as TBA, TBF, TAA, methyl acetate, and acetone. When the method was applied to effluent from a column microcosm prepared with core material from an urban site in New Jersey, conversion of MTBE to TBA was observed after a lag period of 35 days. However, to date, analyses of water samples from six field sites using the DAI-GC/MS method have not produced evidence for the expected products of in situ degradation of MTBE.An analytical method is described that can detect the major alkyl ether compounds that are used as gasoline oxygenates (methyl tert-butyl ether, MTBE; ethyl tert-butyl ether, ETBE; and tert-amyl methyl ether, TAME) and their most characteristic degradation products (tert-butyl alcohol, TBA; tert-butyl formate, TBF; and tert-amyl alcohol, TAA) in water at sub-ppb concentrations. The new method involves gas chromatography (GC) with direct aqueous injection (DAI) onto a polar column via a splitless injector, coupled with detection by mass spectrometry (MS). DAI-GC/MS gives excellent agreement with conventional purge-and-trap methods for MTBE over a wide range of environmentally relevant concentrations. The new method

  16. Splenic infarction after N-butyl-2-cyanoacrylate injection for gastric varices: why does it happen?

    PubMed

    Köksal, Aydin S; Kayaçetin, Ertuğrul; Torun, Serkan; Erkan, Vedat; Ökten, Riza S

    2013-10-01

    Recent guidelines and consensus reports recommend endoscopic injection therapy with N-butyl-2-cyanoacrylate as the first-line treatment for bleeding-isolated gastric varices and gastroesophageal varices types 1 and 2. Embolization is a rare but serious complication of cyanoacrylate injection, which may be fatal in some cases. Herein, we present a patient who developed splenic infarction after N-butyl-cyanoacrylate injection for gastroesophageal varices type 2 and discuss the potential reasons and tips to prevent the occurence of embolization.

  17. Direct puncture embolization using N-butyl cyanoacrylate for a hepatic artery pseudoaneurysm.

    PubMed

    Yoshida, Rie Yagi; Kariya, Shuji; Nakatani, Miyuki; Komemushi, Atsushi; Kono, Yumiko; Tanigawa, Noboru

    2014-03-01

    Massive hemobilia caused by hepatic artery pseudoaneurysm is an uncommon but potentially fatal complication that can occur after biliary intervention. Previous intervention or surgery, atherosclerotic disease, inflammation and even anatomic variants may make the pseudoaneurysm inaccessible to transcatheter approach, therefore it is not always feasible. The present report describes a case of successful embolization of a hepatic artery pseudoaneurysm with N-butyl cyanoacrylate via direct puncture as an alternative approach. The case presentation is followed by the technical points and the properties of N-butyl cyanoacrylate that are particularly advantageous for use in direct puncture procedures.

  18. Reaction of phenanthrene with tert-butylating agents under Friedel-Craft conditions

    SciTech Connect

    Pozdnyakovich, Yu.V.

    1988-10-20

    The alkylation of phenanthrene with tert-butyl alcohol in the presence of trifluoroacetic acid or with tert-butyl chloride, catalyzed by the TiCl/sub 4/, FeCl/sub 3/-CH/sub 3/NO/sub 2/, and AlCl/sub 3/-CH/sub 3/NO/sub 2/, leads to formation of 2- and 3-tert-butylphenanthrene and also 2,6-, 2,7-, and 3,6-di-tert-butylphenanthrene. The exhaustive alkylation of phenanthrene leads to the formation of the above-mentioned isomeric di-tert-butylphenanthrenes, the ratios of which depend on the nature of the catalyst.

  19. [Determination of decomposition products of di-t-butyl peroxide by gas chromatography].

    PubMed

    Zhou, H; Liu, J; Wang, Y; Wu, Y

    1997-07-01

    In this work we found that there were five decomposition products of di-t-butyl peroxide at 320 degrees C by GC-MS. The peak area of acetone as a chief product in the thermal decomposition was related to di-t-butyl peroxide concentration in a linear manner. The range was from 22.91 to 114.93 microg (r=0.9997, n=4). By use of the calibration, we can possibly determine the content of the peroxide rapidly. The present method is more suitable for the determination of peroxide that is liable to decompose and difficult to be vaporized.

  20. 40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

    Code of Federal Regulations, 2012 CFR

    2012-07-01

    ... ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2... 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2'-(1,2-diazenediyl)bis - and...

  1. Microbial toxicity of methyl tert-butyl ether (MTBE) determined with fluorescent and luminescent bioassays.

    PubMed

    Roslev, Peter; Lentz, Trine; Hesselsoe, Martin

    2015-02-01

    The inhibitory effects of the fuel additive methyl tert-butyl ether (MTBE) and potential degradation products tert-butanol (TBA) and formaldehyde was examined using mixed microbial biomass, and six strains of bioluminescent bacteria and yeast. The purpose was to assess microbial toxicity with quantitative bioluminescent and fluorescent endpoints, and to identify sensitive proxies suitable for monitoring MTBE contamination. Bioluminescent Aliivibrio fischeri DSM 7151 (formerly Vibrio fischeri) appeared highly sensitive to MTBE exposure, and was a superior test organisms compared to lux-tagged Escherichia coli DH5α, Pseudomonas fluorescens DF57-40E7 and Saccharomyces cerevisiae BLYR. EC10 and EC50 for acute MTBE toxicity in A. fischeri were 1.1 and 10.9 mg L(-1), respectively. Long term (24h) MTBE exposure resulted in EC10 values of 0.01 mg L(-1). TBA was significantly less toxic with EC10 and EC50 for acute and chronic toxicity >1000 mg L(-1). Inhibition of bioluminescence was generally a more sensitive endpoint for MTBE toxicity than measuring intracellular ATP levels and heterotrophic CO2 assimilation. A weak estrogenic response was detected for MTBE at concentrations ⩾ 3.7 g L(-1) using an estrogen inducible bioluminescent yeast strain (S. cerevisiae BLYES). Microbial hydrolytic enzyme activity in groundwater was affected by MTBE with EC10 values of 0.5-787 mg L(-1), and EC50 values of 59-3073 for alkaline phosphatase, arylsulfatase, beta-1,4-glucanase, N-acetyl-beta-d-glucosaminidase, and leucine-aminopeptidase. Microbial alkaline phosphatase and beta-1,4-glucanase activity were most sensitive to MTBE exposure with EC50 ⩽ 64.8 mg L(-1). The study suggests that bioassays with luminescent A. fischeri, and fluorescent assays targeting hydrolytic enzyme activity are good candidates for monitoring microbial MTBE toxicity in contaminated water.

  2. More about Interactions of Rhodamine 19 Butyl Ester with Rat Liver Mitochondria.

    PubMed

    Rogov, A G; Trendeleva, T A; Aliverdieva, D A; Zvyagilskaya, R A

    2016-04-01

    Oxidative stress is one of the major factors underlying mitochondrial dysfunctions. One of the most promising approaches for alleviating or preventing oxidative stress is the use of cationic uncouplers that accumulate in mitochondria in accordance to the level of the membrane potential, producing "mild" uncoupling. Based on this theoretical background, cationic rhodamine 19 butyl ester (C4R1) was synthesized and tested within the framework of the research project guided by V. P. Skulachev. The results of these tests were presented (Khailova et al. (2014) Biochim. Biophys. Acta, 1837, 1739-1747), but one publication could not accommodate all data on interactions of C4R1 with isolated mitochondria. In addition to previously presented data, we found that the effect of C4R1 on the rate of oxygen uptake is subject to temporal variations, which probably reflects variable rates of C4R1 entry into the mitochondria. Consequently, transient stimulation of respiration can be followed by inhibition. C4R1 was found not to shunt electron flow from complex I of the respiratory chain; it largely acted as an inhibitor of complex I in the respiratory chain and showed antioxidant activity. C4R1 taken at low, non-uncoupling concentrations enhanced the uncoupling activity of fatty acids (e.g. palmitate). Relatively low C4R1 concentrations stimulated opening of a nonspecific Ca2+/Pi-dependent pore. ATP synthesis and hydrolysis were substantially inhibited by C4R1 at low concentrations that had no appreciable effects on respiration in states 4 and 3 and only slightly decreased the membrane potential. Besides, conditions were revealed allowing correct evaluation of the membrane potential generated at the inner mitochondrial membrane with safranin O upon oxidation of both succinate and NAD-dependent substrates in the presence of C4R1. PMID:27293102

  3. U.S. Geological Survey laboratory method for methyl tert-Butyl ether and other fuel oxygenates

    USGS Publications Warehouse

    Raese, Jon W.; Rose, Donna L.; Sandstrom, Mark W.

    1995-01-01

    Methyl tert-butyl ether (MTBE) was found in shallow ground-water samples in a study of 8 urban and 20 agricultural areas throughout the United States in 1993 and 1994 (Squillace and others, 1995, p. 1). The compound is added to gasoline either seasonally or year round in many parts of the United States to increase the octane level and to reduce carbon monoxide and ozone levels in the air. The U.S. Geological Survey (USGS) National Water Quality Laboratory (NWQL), near Denver, uses state-of-the-art technology to analyze samples for MTBE as part of the USGS water-quality studies. In addition, the NWQL offers custom analyses to determine two other fuel oxygenates--ethyl tert-butyl ether (ETBE) and tert-amyl methyl ether (TAME). The NWQL was not able to obtain a reference standard for tert-amyl ethyl ether (TAEE), another possible fuel oxygenate (Shelley and Fouhy, 1994, p. 63). The shallow ground-water samples were collected as part of the USGS National Water-Quality Assessment Program. These samples were collected from 211 urban wells or springs and 562 agricultural wells sampled by the USGS in 1993 and 1994. The wells were keyed to specific land-use areas to assess the effects of different uses on ground-water quality (Squillace and others, 1995, p. 2). Ground-water samples were preserved on site to pH less than or equal to 2 with a solution of 1:1 hydrochloric acid. All samples were analyzed at the NWQL within 2 weeks after collection. The purpose of this fact sheet is to explain briefly the analytical method implemented by the USGS for determining MTBE and other fuel oxygenates. The scope is necessarily limited to an overview of the analytical method (instrumentation, sample preparation, calibration and quantitation, identification, and preservation of samples) and method performance (reagent blanks, accuracy, and precision).

  4. Carbon isotopic fractionation during anaerobic biotransformation of methyl tert-butyl ether and tert-amyl methyl ether.

    PubMed

    Somsamak, Piyapawn; Richnow, Hans H; Häggblom, Max M

    2005-01-01

    The fuel oxygenate methyl tert-butyl ether (MTBE) has been frequently detected in groundwater and surface water. Since contaminated sites are often subsurface, anaerobic degradation of MTBE will likely be significant for remediation. As traditional approaches to evaluate biodegradation generally involve laboratory microcosm studies which require time and resources, innovative approaches are needed to demonstrate active in situ biodegradation of MTBE. This study was conducted to gather information at the laboratory level to evaluate the potential of applying carbon isotope fractionation as an indicator for in situ biodegradation of the fuel oxygenates MTBE and tert-amyl methyl ether (TAME). In this study, MTBE utilization was observed in a methanogenic sediment microcosm after a lengthy lag period of about 400 days. MTBE utilization was sustained upon refeeding and subculturing. tert-Butyl alcohol (TBA) was found to accumulate after propagation of cultures. The MTBE-grown cultures also utilized TAME and produced tert-amyl alcohol (TAA). The detection of TBA and TAA indicated that ether bond cleavage was the initial step in degradation for both compounds. Carbon isotope fractionation during anaerobic MTBE and TAME degradation was studied, and isotopic enrichment factors (epsilon) with 95% confidence intervals of -15.6 +/-4.1% and -13.7+/-4.5% were estimated for anaerobic MTBE and TAME degradation, respectively. Addition of 2-bromoethanesulfonic acid, an inhibitor of methanogenesis, substantially prolonged the lag period before transformation, but did not influence carbon isotope fractionation. Our experiment provided strong evidence of significant carbon isotope fractionation during anaerobic MTBE and TAME degradation, demonstrating that this technique can be used as an indicator for in situ MTBE and TAME degradation.

  5. Separation of methyl t-butyl ether from close boiling C[sub 5] hydrocarbons by extractive distillation

    SciTech Connect

    Berg, L.

    1993-07-20

    A method for recovering methyl t-butyl ether from a mixture of methyl t-butyl ether and 1-pentene which comprises distilling a mixture of methyl t-butyl ether and 1-pentene in the presence of about one part of an extractive agent per part of methyl t-butyl ether -- 1-pentene mixture, recovering the 1-pentene as overhead product and obtaining the methyl t-butyl ether and the extractive agent from the still pot, wherein said extractive agent consists of one material selected from the group consisting of sulfolane, nitroethane, t-butanol, ethylene glycol diacetate, 1-methoxy-2-propanol acetate, methyl isoamyl ketone, ethylene glycol methyl ether, propylene glycol phenyl ether and diethyl malonate.

  6. Regioisomer-Free C 4h β-Tetrakis(tert-butyl)metallo-phthalocyanines: Regioselective Synthesis and Spectral Investigations.

    PubMed

    Iida, Norihito; Tanaka, Kenta; Tokunaga, Etsuko; Takahashi, Hiromi; Shibata, Norio

    2015-04-01

    Metal β-tetrakis(tert-butyl)phthalocyanines are the most commonly used phthalocyanines due to their high solubility, stability, and accessibility. They are commonly used as a mixture of four regioisomers, which arise due to the tert-butyl substituent on the β-position, and to the best of our knowledge, their regioselective synthesis has yet to be reported. Herein, the C 4h -selective synthesis of β-tetrakis(tert-butyl)metallophthalocyanines is disclosed. Using tetramerization of α-trialkylsilyl phthalonitriles with metal salts following acid-mediated desilylation, the desired metallophthalocyanines were obtained in good yields. Upon investigation of regioisomer-free zinc β-tetrakis(tert-butyl)phthalocyanine using spectroscopy, the C 4h single isomer described here was found to be distinct in the solid state to zinc β-tetrakis(tert-butyl)phthalocyanine obtained by a conventional method.

  7. Double-Balloon-Assisted n-Butyl-2-Cyanoacrylate Embolization of Intrahepatic Arterioportal Shunt Prior to Chemoembolization of Hepatocellular Carcinoma.

    PubMed

    Takao, Hidemasa; Shibata, Eisuke; Ohtomo, Kuni

    2016-10-01

    A case of multiple hepatocellular carcinomas with a severe intrahepatic arterioportal shunt that was successfully embolized with n-butyl-2-cyanoacrylate with coaxial double-balloon occlusion prior to transcatheter arterial chemoembolization is presented. A proximal balloon positioned at the proper hepatic artery was used for flow control, and a coaxial microballoon, positioned in the closest of three arterial feeding branches to the arterioportal shunt, was used to control the delivery of n-butyl-2-cyanoacrylate. This coaxial double-balloon technique can prevent proximal embolization and distal migration of n-butyl-2-cyanoacrylate and enable precise control of the distribution of n-butyl-2-cyanoacrylate. It could also be applicable to n-butyl-2-cyanoacrylate embolization for other than intrahepatic arterioportal shunt.

  8. Health studies indicate MTBE is safe gasoline additive

    SciTech Connect

    Anderson, E.V.

    1993-09-01

    Implementation of the oxygenated fuels program by EPA in 39 metropolitan areas, including Fairbanks and Anchorage, Alaska, in the winter of 1992, encountered some unexpected difficulties. Complaints of headaches, dizziness, nausea, and irritated eyes started in Fairbanks, jumped to Anchorage, and popped up in various locations in the lower 48 states. The suspected culprit behind these complaints was the main additive for oxygenation of gasoline is methyl tert-butyl ether (MTBE). A test program, hastily organized in response to these complaints, has indicated that MTBE is a safe gasoline additive. However, official certification of the safety of MTBE is still awaited.

  9. Acute toxicity of gasoline and some additives.

    PubMed Central

    Reese, E; Kimbrough, R D

    1993-01-01

    The acute toxicity of gasoline; its components benzene, toluene, and xylene; and the additives ethanol, methanol, and methyl tertiary butyl ether are reviewed. All of these chemicals are only moderately to mildly toxic at acute doses. Because of their volatility, these compounds are not extensively absorbed dermally unless the exposed skin is occluded. Absorption through the lungs and the gastrointestinal tract is quite efficient. After ingestion, the principal danger for a number of these chemicals, particularly gasoline, is aspiration pneumonia, which occurs mainly in children. It is currently not clear whether aspiration pneumonia would still be a problem if gasoline were diluted with ethanol or methanol. During the normal use of gasoline or mixtures of gasoline and the other solvents as a fuel, exposures would be much lower than the doses that have resulted in poisoning. No acute toxic health effects would occur during the normal course of using automotive fuels. PMID:8020435

  10. Acute toxicity of gasoline and some additives

    SciTech Connect

    Reese, E.; Kimbrough, R.D.

    1993-12-01

    The acute toxicity of gasoline; its components benzene, toluene, and xylene; and the additives ethanol, methanol, and methyl tertiary butyl ether are reviewed. All of these chemicals are only moderately to mildly toxic at acute doses. Because of their volatility, these compounds are not extensively absorbed dermally unless the exposed skin is occluded. Absorption through the lungs and the gastrointestinal tract is quite efficient. After ingestion, the principal danger for a number of these chemicals, particularly gasoline, is aspiration pneumonia, which occurs mainly in children. It is currently not clear whether aspiration pneumonia would still be a problem if gasoline were diluted with ethanol or methanol. During the normal use of gasoline or mixtures of gasoline and the other solvents as a fuel, exposures would be much lower than the doses that have resulted in poisoning. No acute toxic health effects would occur during the normal course of using automotive fuels. 128 refs., 7 tabs.

  11. 40 CFR 721.10193 - 1-Butanaminium, N-(3-aminopropyl)-N-butyl-N-(2-carboxyethyl)-, N-coco acyl derivs., inner salts.

    Code of Federal Regulations, 2011 CFR

    2011-07-01

    ...-butyl-N-(2-carboxyethyl)-, N-coco acyl derivs., inner salts. 721.10193 Section 721.10193 Protection of...-aminopropyl)-N-butyl-N-(2-carboxyethyl)-, N-coco acyl derivs., inner salts. (a) Chemical substance and...-aminopropyl)-N-butyl-N-(2-carboxyethyl)-, N-coco acyl derivs., inner salts (PMN P-06-263, Chemical B; CAS...

  12. INHALATION EXPOSURE TO METHYL TERT-BUTYL ETHER (MTBE) AND DIBROMOCHLOROMETHANE (DBCM) USING CONTINUOUS BREATH ANALYSIS

    EPA Science Inventory

    The oxygenate methyl tert-butyl ether (MTBE) has been added to gasoline to help meet national ambient air quality standards in those parts of the U.S. that are non-compliant for carbon monoxide. Although MTBE has provided important health benefits in terms of reduced haza...

  13. Characterization of cellulose II nanoparticles regenerated from ionic liquid, 1-butyl-3-methylimidazolium chloride

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Regenerated cellulose nanoparticles (RCNs) including both elongated fiber and spherical structures were prepared from microcrystalline cellulose (MCC)and cotton using 1-butyl-3-methylimidazolium chloride followed by high-pressure homogenization. The crystalline structure of RCNs was cellulose II in ...

  14. A direct and sustainable synthesis of tertiary butyl esters enabled by flow microreactors.

    PubMed

    Degennaro, Leonardo; Maggiulli, Daniela; Carlucci, Claudia; Fanelli, Flavio; Romanazzi, Giuseppe; Luisi, Renzo

    2016-08-01

    Tertiary butyl esters find large applications in synthetic organic chemistry. A straightforward method for the direct introduction of the tert-butoxycarbonyl group into a variety of organic compounds has been developed using flow microreactor systems. The resultant flow process was more efficient, versatile and sustainable compared to the batch.

  15. IRIS Toxicological Review of Ethyl Tertiary Butyl Ether (Etbe) (Public Comment Draft)

    EPA Science Inventory

    In September 2016, the U.S. Environmental Protection Agency's (USEPA) released the draft Integrated Risk Information System (IRIS) Toxicological Review of Ethyl Tertiary Butyl Ether (ETBE). Consistent with the 2013 IRIS Enhancements, draft IRIS assessments are released prior to e...

  16. N-Butyl 2-Cyanoacrylate Embolization of Spinal Dural Arteriovenous Fistula

    PubMed Central

    Kwon, B.J.; Kim, T.-K.; Seo, S.I.; Kyung, J.B.; Seol, H.Y.; Han, M.H.

    2005-01-01

    Summary We report an unusual case of spinal dural arteriovenous fistula (SDAVF) presenting with subarachnoid haemorrhage (SAH). Cure was achieved with endovascular treatment with n-butyl 2-cyanoacrylate (NBCA). A review of the literature revealed five cases of cervical SDAVF that presented with SAH. None of these cases were treated with NBCA. PMID:20584439

  17. Enhanced diisobutene production in the presence of methyl tertiary butyl ether

    DOEpatents

    Smith, Jr., Lawrence A.

    1983-01-01

    In the liquid phase reaction of isobutene in the presence of resin cation exchange resins with itself in a C.sub.4 hydrocarbon stream to form dimers, the formation of higher polymers, oligomers, and co-dimer by-products is suppressed by the presence of 0.0001 to 1 mole per mole of isobutene of methyl tertiary butyl ether.

  18. STRUCTURES AND BINDING ENERGIES OF METHYL TERT-BUTYL ETHER-WATER COMPLEXES

    EPA Science Inventory

    Methyl tert-butyl ether (MTBE) is a well-known environmental contaminant owing to its high solubility in water. Since the early 1990s, MTBE has been added to gasoline to improve air quality in some metropolitan areas of the United States. Improved air quality was, however, achiev...

  19. Enhanced diisobutene production in the presence of methyl tertiary butyl ether

    DOEpatents

    Smith, L.A. Jr.

    1983-03-01

    In the liquid phase reaction of isobutene in the presence of resin cation exchange resins with itself in a C[sub 4] hydrocarbon stream to form dimers, the formation of higher polymers, oligomers, and co-dimer by-products is suppressed by the presence of 0.0001 to 1 mole per mole of isobutene of methyl tertiary butyl ether. 1 fig.

  20. PHOTOCATALYTIC OXIDATION OF METHYL-TERT-BUTYL ETHER FOR DRINKING WATER TREATMENT

    EPA Science Inventory

    The photo-oxidation of methyl tert-butyl ether (MTBE) in water was investigated to determine the feasibility of using photocatalysis for the treatment of MTBE-contaminated drinking water. The feasibility assessment was conducted using slurries of titanium dioxide in both a photo-...

  1. IRIS Toxicological Review of Ethyl Tertiary Butyl Ether (Etbe) (Interagency Science Consultation Draft)

    EPA Science Inventory

    In September 2016, EPA released the draft IRIS Toxicological Review of Ethyl Tertiary Butyl Ether (ETBE) for public comment and discussion. The draft assessment was reviewed internally by EPA and by other federal agencies and White House Offices before public release. Consistent ...

  2. tert-Butyl 6-amino-5-cyano-2-(2-meth-oxy-eth-yl)nicotinate.

    PubMed

    Chen, Yi-Ning; Zhao, Xing-Dong; Deng, Jie; Li, Qin-Geng

    2012-05-01

    The title compound, C(14)H(19)N(3)O(3), was synthesized by the reaction of 3-meth-oxy-propionitrile, tert-butyl bromo-acetate and eth-oxy-methyl-enemalononitrile. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into chains propagating along the b axis.

  3. IRIS Toxicological Review of Tert-Butyl Alcohol (Tert-Butanol) (Public Comment Draft)

    EPA Science Inventory

    EPA is developing an Integrated Risk Information System (IRIS) assessment of tert-butyl Alcohol (tert-butanol) and has released the public comment draft assessment for public comment and external peer review. When final, the assessment will appear on the IRIS databa...

  4. MONITORED NATURAL ATTENUATION OF TERTIARY BUTYL ALCOHOL (TBA) IN GROUND WATER AT GASOLINE SPILL SITES

    EPA Science Inventory

    The state agencies that implement the Underground Storage Tank program rely heavily on Monitored Natural Attenuation (MNA) to clean up contaminants such as benzene and methyl tertiary butyl ether (MTBE) at gasoline spill sites. This is possible because the contaminants are biolo...

  5. Aerobic mineralization of MTBE and tert-butyl alcohol by stream-bed sediment microorganisms

    USGS Publications Warehouse

    Bradley, P.M.; Landmeyer, J.E.; Chapelle, F.H.

    1999-01-01

    Microorganisms indigenous to the stream-bed sediments at two gasoline- contaminated groundwater sites demonstrated significant mineralization of the fuel oxygenates, methyl tert-butyl ether (MTBE) and tert-butyl alcohol (TBA). Up to 73% of [U-14C]-MTBE and 84% of [U-14C]-TBA were degraded to 14CO2 under mixed aerobic/anaerobic conditions. No significant mineralization was observed under strictly anaerobic conditions. The results indicate that, under the mixed aerobic/anaerobic conditions characteristic of stream-bed sediments, microbial processes may provide a significant environmental sink for MTBE and TBA delivered to surface water bodies by contaminated groundwater or by other sources.Microorganisms indigenous to the stream-bed sediments at two gasoline-contaminated groundwater sites demonstrated significant mineralization of the fuel oxygenates, methyl tert-butyl ether (MTBE) and tert-butyl alcohol (TBA). Up to 73% of [U-14C]-MTBE and 84% of [U-14C]-TBA were degraded to 14CO2 under mixed aerobic/anaerobic conditions. No significant mineralization was observed under strictly anaerobic conditions. The results indicate that, under the mixed aerobic/anaerobic conditions characteristic of stream-bed sediments, microbial processes may provide a significant environmental sink for MTBE and TBA delivered to surface water bodies by contaminated groundwater or by other sources.

  6. IRIS Toxicological Review of Tert-Butyl Alcohol (Tert-Butanol) (Interagency Science Consultation Draft)

    EPA Science Inventory

    On April 29, 2016, the Toxicological Review of tert-Butyl Alcohol (tert-Butanol) (Public Comment Draft) was released for public comment. The draft Toxicological Review and charge were reviewed internally by EPA and by other federal agencies and the Executive Office ...

  7. The antioxidant butylated hydroxyanisole potentiates the toxic effects of propylparaben in cultured mammalian cells.

    PubMed

    Pérez Martín, José Manuel; Fernández Freire, Paloma; Daimiel, Lidia; Martínez-Botas, Javier; Sánchez, Covadonga Martín; Lasunción, Miguel Ángel; Peropadre, Ana; Hazen, María José

    2014-10-01

    Butylated hydroxyanisole and propylparaben are phenolic preservatives commonly used in food, pharmaceutical and personal care products. Both chemicals have been subjected to extensive toxicological studies, due to the growing concern regarding their possible impacts on environmental and human health. However, the cytotoxicity and underlying mechanisms of co-exposure to these compounds have not been explored. In this study, a set of relevant cytotoxicity endpoints including cell viability and proliferation, oxidative stress, DNA damage and gene expression changes were analyzed to assess whether the antioxidant butylated hydroxyanisole could prevent the pro-oxidant effects caused by propylparaben in Vero cells. We demonstrated that binary mixtures of both chemicals induce greater cytotoxic effects than those reported after single exposureto each compound. Simultaneous treatment with butylated hydroxyanisole and propylparaben caused G0/G1 cell cycle arrest as a result of enhanced generation of oxidative stress and DNA double strand breaks. DNA microarray analysis revealed that a cross-talk between transforming growth factor beta (TGFβ) and ataxia-telangiectasia mutated kinase (ATM) pathways regulates the response of Vero cells to the tested compounds in binary mixture. Our findings indicate that butylated hydroxyanisole potentiates the pro-oxidant effects of propylparaben in cultured mammalian cells and provide useful information for their safety assessment.

  8. 76 FR 46796 - Butylate; Registration Review Proposed Decision; Notice of Availability

    Federal Register 2010, 2011, 2012, 2013, 2014

    2011-08-03

    ... Register on July 28, 2010 (75 FR 44240; FRL-8835-2). For the remaining butylate product registrations... published in the Federal Register on March 23, 2011 (76 FR 16147, FRL-8867-8). Due to the cancellation... perform its intended function without unreasonable adverse effects on human health or the...

  9. tert-Butyl Sulfoxide as a Starting Point for the Synthesis of Sulfinyl Containing Compounds.

    PubMed

    Wei, Juhong; Sun, Zhihua

    2015-11-01

    Sulfoxides bearing a tert-butyl group can be activated using N-bromosuccinimide (NBS) under acidic conditions and then subsequently treated with a variety of nitrogen, carbon, or oxygen nucleophiles to afford a wide range of the corresponding sulfinic acid amides, new sulfoxides, and sulfinic acid esters. PMID:26502058

  10. IRIS Toxicological Review of Ethyl Tertiary Butyl Ether (Etbe) (External Review Draft, 2009)

    EPA Science Inventory

    EPA is conducting a peer review and public comment of the scientific basis supporting the human health hazard and dose-response assessment of ethyl tertiary butyl ether (ETBE) that when finalized will appear on the Integrated Risk Information System (IRIS) database.

  11. TREATMENT OF METHYL TERT-BUTYL ETHER CONTAMINATED WATER USING PHOTOCATALYSIS

    EPA Science Inventory

    The feasibility of photo-oxidation treatment of methyl tert-butyl ether (MTBE) in water was investigated in three ways, 1) using a slurry falling film photo-reactor, 2) a batch solar reactor system, and 3) a combination of air-stripping and gas phase photooxidation system. MTBE-c...

  12. Draft Genome Sequence of Sphingobium yanoikuyae TJ, a Halotolerant Di-n-Butyl-Phthalate-Degrading Bacterium

    PubMed Central

    Jin, Decai; Zhu, Ying; Wang, Xinxin; Kong, Xiao; Liu, Huijun; Wang, Yafeng

    2016-01-01

    Sphingobium yanoikuyae TJ is a halotolerant di-n-butyl-phthalate-degrading bacterium, isolated from the Haihe estuary in Bohai Bay, Tianjin, China. Here, we report the 5.1-Mb draft genome sequence of this strain, which will provide insights into the diversity of Sphingobium spp. and the mechanism of phthalate ester degradation in the estuary. PMID:27313307

  13. REFINED PBPK MODEL OF AGGREGATE EXPOSURE TO METHYL TERTIARY-BUTYL ETHER

    EPA Science Inventory

    Aggregate (multiple pathway) exposures to methyl tertiary-butyl ether (MTBE) in air and water occur via dermal, inhalation, and oral routes. Previously, physiologically-based pharmacokinetic (PBPK) models have been used to quantify the kinetic behavior of MTBE and its primary met...

  14. IRIS Toxicological Review of Ethylene Glycol Mono-Butyl Ether (EGBE) (Interagency Science Discussion Draft)

    EPA Science Inventory

    EPA is releasing the draft report, Toxicological Review for Ethylene Glycol Mono-Butyl Ether , that was distributed to Federal agencies and White House Offices for comment during the Science Discussion step of the IRIS Assessme...

  15. BIODEGRADATION OF METHYL TERT-BUTYL ETHER USING AN INNOVATIVE BIOMASS CONCENTRATOR REACTOR

    EPA Science Inventory

    The aerobic biodegradation of methyl tert-butyl ether (MTBE) was investigated using a pilot-scale Biomass Concentrator Reactor (BCR). The reactor was operated for a year at a flow rate of 2500 L/d of Cincinnati dechlorinated tap water and an influent MTBE concentration o...

  16. BIODEGRADATION OF METHYL TERT-BUTYL ETHER AND BTEX AT VARYING HYDRAULIC RETENTION TIMES

    EPA Science Inventory

    The feasibility of biologically degrading methyl tert-butyl ether (MTBE) contaminated groundwater is dependent on the ability to degrade MTBE and its byproducts in the presence of other gasoline contaminants. This study investigates a mixed culture degrading both MTBE and benzene...

  17. Posttraumatic High-Flow Priapism Treated byN-Butyl-Cyanoacrylate Embolization

    SciTech Connect

    Numan, Fueruzan; Cakirer, Sinan; Islak, Civan; Oabguet, Guenduez; Kadioabglu, Ates; Cayan, Selahittin; Tellaloabglu, Sedat

    1996-04-15

    A patient with high-flow priapism was treated by transcatheter embolization of a posttraumatic left cavernosal arteriovenous fistula using N-butyl-cyanoacrylate (NBCA), resulting in complete detumescence. Erectile function has been preserved during a 3-month follow-up. Only two patients with NBCA embolization for high-flow priapism have been reported previously.

  18. AN EVALUATION OF THE HUMAN CARCINOGENIC POTENTIAL OF ETHYLENE GLYCOL BUTYL ETHER (EGBE)

    EPA Science Inventory

    Background

    The position paper, An Evaluation of the Human Carcinogenic Potential of Ethylene Glycol Butyl Ether, was developed in support of the Agency's evaluation of a petition from the...

  19. A thermal lensing study of a photolysis of di- t-butyl peroxide

    NASA Astrophysics Data System (ADS)

    Fuke, K.; Hasegawa, A.; Ueda, M.; Itoh, M.

    1981-11-01

    A photolysis of di- t-butyl peroxide (BOOB) was studied by using a thermal lensing technique. This technique is found to be applicable to the determination Of the rate Constants of the decay of t-butoxy radical (BO ) and the hydrogen abstraction reaction.

  20. Energetic Materials Center Report--Small-Scale Safety and Thermal Testing Evaluation of Butyl Nitrate

    SciTech Connect

    Hsu, Peter C.; Reynolds, John G.

    2013-04-26

    Butyl Nitrate (BN) was examined by Small-Scale Safety and Thermal (SSST) Testing techniques to determine its sensitivity to impact, friction, spark and thermal exposure simulating handling and storage conditions. Under the conditions tested, the BN exhibits thermal sensitivity above 150 °C, and does not exhibit sensitive to impact, friction or spark.

  1. Palladium-catalyzed oxidative carbonylation of ethylene and propylene by butyl nitrite and carbon monoxide

    SciTech Connect

    Brechot, P.; Chauvin, Y.; Commereuc, D.; Saussine, L. )

    1990-01-01

    In the oxidative carbonylation of ethylene by carbon monoxide and butyl nitrite catalyzed by PdCl{sub 2}(PhCN){sub 2} in the presence of triphenylphosphine, the pentacoordinated tetravalent palladium complex PdCl{sub 2}(COOBu)NO(PPh{sub 3}) has been isolated and has proved to be an intermediate in the catalytic cycle.

  2. INFLUENCE OF METHYL TERT-BUTYL ETHER (MTBE) ON LAKE WATER ALGAE

    EPA Science Inventory

    Methyl tert-butyl ether (MTBE) has been used as an octane booster in gasoline in the United States since the 1970s. MTBE use increased greatly in the 1990s with the implementation of the Clean Air Act Amendments of 1990. The MTBE enhanced a more complete combustion of fuel hydroc...

  3. Impact of activation methods on persulfate oxidation of methyl tert-butyl ether.

    PubMed

    Deng, Dayi; Peng, Libin; Guan, Mengyun; Kang, Yuan

    2014-01-15

    To provide guidance on the selection of proper persulfate processes for the remediation of MTBE contaminated groundwater, MTBE aqueous solutions were treated with three common field persulfate processes including heat activated persulfate, Fe(III)-EDTA activated persulfate and alkaline persulfate, respectively. The results were compared with MTBE oxidation by Fenton's reagent and persulfate alone at 25°C. The impact of the activating conditions on the fate of MTBE and its daughter products was investigated. Heat activation at 40°C offered the most rapid removal of MTBE and its daughter products, while Fe(III)-EDTA activation showed higher efficiency of MTBE removal but low removal efficiency of its daughter products. On the other hand, alkaline persulfate showed slower kinetics for the removal of MTBE and less accumulation of the daughter products. Furthermore, tert-butyl alcohol and acetone were observed as the main purgeable daughter products along with a small amount of tert-butyl formate in persulfate oxidation of MTBE, while tert-butyl formate, tert-butyl alcohol and acetone were the main products in Fenton oxidation. Mechanistic analysis suggests that degradation of MTBE by persulfate most likely happens via non-oxygen demand pathways, different from the dominant oxygen demand degradation pathways observed in Fenton oxidation.

  4. Lipid peroxidation and haemoglobin degradation in red blood cells exposed to t-butyl hydroperoxide. The relative roles of haem- and glutathione-dependent decomposition of t-butyl hydroperoxide and membrane lipid hydroperoxides in lipid peroxidation and haemolysis.

    PubMed

    Trotta, R J; Sullivan, S G; Stern, A

    1983-06-15

    Red cells exposed to t-butyl hydroperoxide undergo lipid peroxidation, haemoglobin degradation and hexose monophosphate-shunt stimulation. By using the lipid-soluble antioxidant 2,6-di-t-butyl-p-cresol, the relative contributions of t-butyl hydroperoxide and membrane lipid hydroperoxides to oxidative haemoglobin changes and hexose monophosphate-shunt stimulation were determined. About 90% of the haemoglobin changes and all of the hexose monophosphate-shunt stimulation were caused by t-butyl hydroperoxide. The remainder of the haemoglobin changes appeared to be due to reactions between haemoglobin and lipid hydroperoxides generated during membrane peroxidation. After exposure of red cells to t-butyl hydroperoxide, no lipid hydroperoxides were detected iodimetrically, whether or not glucose was present in the incubation. Concentrations of 2,6-di-t-butyl-p-cresol, which almost totally suppressed lipid peroxidation, significantly inhibited haemoglobin binding to the membrane but had no significant effect on hexose monophosphate shunt stimulation, suggesting that lipid hydroperoxides had been decomposed by a reaction with haem or haem-protein and not enzymically via glutathione peroxidase. The mechanisms of lipid peroxidation and haemoglobin oxidation and the protective role of glucose were also investigated. In time-course studies of red cells containing oxyhaemoglobin, methaemoglobin or carbonmono-oxyhaemoglobin incubated without glucose and exposed to t-butyl hydroperoxide, haemoglobin oxidation paralleled both lipid peroxidation and t-butyl hydroperoxide consumption. Lipid peroxidation ceased when all t-butyl hydroperoxide was consumed, indicating that it was not autocatalytic and was driven by initiation events followed by rapid propagation and termination of chain reactions and rapid non-enzymic decomposition of lipid hydroperoxides. Carbonmono-oxyhaemoglobin and oxyhaemoglobin were good promoters of peroxidation, whereas methaemoglobin relatively spared the

  5. Distribution of 1-Butyl-3-methylimidazolium Bistrifluoromethylsulfonimide in Mesoporous Silica as a Function of Pore Filling

    SciTech Connect

    Han, Kee Sung; Wang, Xiqing; Hagaman, Edward {Ed} W; Dai, Sheng

    2013-01-01

    Rotational dynamics of the ionic liquid (IL) 1-butyl-3-methlyimidazolium bistrifluoromethylsulfonimide, [C4mim][Tf2N], 1, as a neat liquid and confined in mesoporous silica were investigated by 1H spin-spin (T2) and spin-lattice (T1) relaxation measurements and 13C NMR spectroscopy. Translational dynamics (self-diffusion) were monitored via the diffusion coefficient, D, obtained with 1H pulsed field gradient NMR measurements. These data were used to determine the distribution of 1 in the pores of KIT-6, a mesoporous silica with a bicontinuous gyroid pore structure, as a function of filling fraction. Relaxation studies performed as a function of filling factor and temperature, reveal a dynamic heterogeneity in both translational and rotational motions for 1 at filling factors, f, = 0.2-1.0 (f = 1 corresponds to fully filled pores). Spin-lattice and spin-spin relaxation times reveal the motion of 1 in silica mesopores conform to that expected for a two-dimensional relaxation model. The relaxation dynamics are interpreted using a two-state, fast exchange model for all motions; a slow rotation (and translation) of molecules in contact with the surface and a faster motion approximated by the values for bulk relaxation and diffusion. 1 retains liquid like behavior at all filling factors and temperatures that extend to ca. 50 degrees below the bulk melting point. Translational motion in these systems, interpreted with MD-simulated diffusivity limits, confirms the high propensity of 1 to form a monolayer film on the silica surface at low filling factors.. The attractive interaction of 1 with the surface is greater than that for self-association of 1. The trends in diffusion data at short and long diffusion time suggest that the population of surface-bound 1 is in intimate contact with 1 in the pores. This condition is most easily met at higher filling fractions with successive additions of 1 increasing the layer thickness built up on the surface layer.

  6. Molecular Simulation of Water Extraction into a Tri-n-Butyl-Phosphate/n-Dodecane Solution

    SciTech Connect

    de Almeida, Valmor F; Ye, Xianggui; Cui, Shengting; Khomami, Bamin

    2013-01-01

    Abstract: Molecular dynamics simulations were performed to investigate water extraction into a solution of 30 vol% tri-n-butyl-phosphate (TBP) in n-dodecane. This solvent extraction mixture is commonly used in hydrometallurgical and nuclear fuel recycling operations for recovering metals from aqueous streams. It is known that water is coextracted in the organic phase and that it competes with metal ions for the available extractant agent (TBP). Therefore investigating pure water extraction provides a realistic prototype to test molecular simulation methods for the first time in this area. Our computational results indicate that the TBP electric dipole moment has a significant effect on the predicted water solubility. A larger TBP dipole moment decreases the aqueous-organic interfacial tension, leading to increased roughness of the aqueous-organic interface. Interfacial roughness has a significant effect on disrupting the interfacial water hydrogen bonding structure, resulting in a greater number of dangling water molecules at the interface. This enhances the probability of water molecules to break away from the aqueous phase and to migrate into the bulk of the organic phase. Therefore, the magnitude of the TBP dipole moment is a crucial factor in controlling water hydrogen bond breaking at the aqueous-organic interface. By slightly lowering the atomic partial charges of the TBP atoms, to produce a dipole moment that better agrees with experimental data, we were able to predict water solubility in close agreement with experimental measurements. Hence we demonstrate that a molecular modeling and simulation approach may provide quantitative support to experimental programs in this area. In addition, our simulation results shed light into the molecular mechanism of water extraction, the critical role of TBP, and the structural forms of water molecules both at the interface and in the bulk of the organic phase. Specifically, it is found that water molecules are

  7. MICROWAVE-ASSISTED PREPARATION OF 1-BUTYL-3-METHYLIMIDAZOLIUM TETRACHLOROGALLATE AND ITS CATALYTIC USE IN ACETAL FORMATION UNDER MILD CONDITIONS

    EPA Science Inventory

    1-Butyl-3-methylimidazolium tetrachlorogallate, [bmim][GaCl4], prepared via microwave-assisted protocol, is found to be an active catalyst for the efficient acetalization of aldehydes under mild conditions.

  8. Portal Hypertension Secondary to Spontaneous Arterio-Portal Venous Fistulas: Transcatheter Arterial Embolization with n-Butyl Cyanoacrylate and Microcoils

    SciTech Connect

    Yamagami, Takuji; Nakamura, Toshiyuki; Nishimura, Tsunehiko

    2000-09-15

    We report a 73-year-old man with recurrent variceal bleeding due to portal hypertension caused by multiple intrahepatic arterio-portal venous fistulas, which were successfully occluded by embolization with n-butyl cyanoacrylate and micro-coils.

  9. ATOM TRANSFER RADICAL POLYMERIZATION OF N-BUTYL METHACRYLATE IN AQUEOUS DISPERSED SYSTEMS: A MINIEMULSION APPROACH. (R826735)

    EPA Science Inventory

    Ultrasonication was applied in combination with a hydrophobe for the copper-mediated atom transfer radical polymerization of n-butyl methacrylate in an aqueous dispersed system. A controlled polymerization was successfully achieved, as demonstrated by a linear correlation between...

  10. Transcatheter Embolization of a Coronary Fistula Originating from the Left Anterior Descending Artery by Using N-Butyl 2-Cyanoacrylate

    SciTech Connect

    Karagoz, Tevfik; Celiker, Alpay E-mail: tkaraqoz@hacettepe.edu.tr; Cil, Barbaros; Cekirge, Saruhan

    2004-11-15

    In this report, we describe a successful percutaneous transcatheter n-butyl 2-cyanoacrylate embolization of a coronary fistula originating from the left anterior descending artery in an adolescent with unexpected recurrent attacks of myocardial ischemia.

  11. Butyl hydroxy toluene antagonizes the gastric toxicity but not the pharmacological activity of acetylsalicylic acid in rats.

    PubMed

    van Kolfschoten, A A; Hagelen, F; van Noordwijk, J

    1984-03-01

    Butyl hydroxy toluene reduced gastric erosion due to acetylsalicylic acid in the rat, but not the antiinflammatory, anti-pyretic and analgesic activity. By itself, BHT exhibited activity only in the test on analgesia. PMID:6728039

  12. No Promoting Effect of Ethyl Tertiary-butyl Ether (ETBE) on Rat Urinary Bladder Carcinogenesis Initiated with N-Butyl-N-(4-hydroxybutyl)nitrosamine.

    PubMed

    Hagiwara, Akihiro; Imai, Norio; Doi, Yuko; Suguro, Mayuko; Kawabe, Mayumi; Furukawa, Fumio; Nagano, Kasuke; Fukushima, Shoji

    2013-12-01

    The effects of ethyl tertiary-butyl ether (ETBE) on two-stage urinary bladder carcinogenesis in male F344 rats initiated with N-butyl-N-(4-hydroxybutyl)nitrosamine (BBN) were investigated at various dose levels with regard to possible promoting activity. Groups of 30 rats were given drinking water containing 500 ppm BBN, as an initiator, for 4 weeks and starting one week thereafter received ETBE by gavage (daily, 7 days/week) at dose levels of 0 (control), 100, 300, 500 or 1000 mg/kg/day until experimental week 36. No statistically significant differences in incidences of preneoplastic lesions, papillomas, and carcinomas of the urinary bladder were evident in rats treated with 100-1000 mg/kg/day ETBE as compared with control values. Furthermore, the average numbers of preneoplastic or neoplastic lesions per unit length of basement membrane in rats given 100-1000 mg/kg/day ETBE were also comparable to control values. However, papillomatosis of the urinary bladder was found in 4 out of 30 rats (13%) in the group given 1000 mg/kg/day ETBE, and soft stones in the urinary bladder were found in 3 out of these 4 rats. The results thus demonstrated that ETBE did not exert promotional activity on urinary bladder carcinogenesis. However, papillomatosis of the urinary bladder developed in small numbers of the rats given ETBE at 1000 mg/kg/day but not in rats given 500 mg/kg/day or lower doses.

  13. No Promoting Effect of Ethyl Tertiary-butyl Ether (ETBE) on Rat Urinary Bladder Carcinogenesis Initiated with N-Butyl-N-(4-hydroxybutyl)nitrosamine

    PubMed Central

    Hagiwara, Akihiro; Imai, Norio; Doi, Yuko; Suguro, Mayuko; Kawabe, Mayumi; Furukawa, Fumio; Nagano, Kasuke; Fukushima, Shoji

    2013-01-01

    The effects of ethyl tertiary-butyl ether (ETBE) on two-stage urinary bladder carcinogenesis in male F344 rats initiated with N-butyl-N-(4-hydroxybutyl)nitrosamine (BBN) were investigated at various dose levels with regard to possible promoting activity. Groups of 30 rats were given drinking water containing 500 ppm BBN, as an initiator, for 4 weeks and starting one week thereafter received ETBE by gavage (daily, 7 days/week) at dose levels of 0 (control), 100, 300, 500 or 1000 mg/kg/day until experimental week 36. No statistically significant differences in incidences of preneoplastic lesions, papillomas, and carcinomas of the urinary bladder were evident in rats treated with 100–1000 mg/kg/day ETBE as compared with control values. Furthermore, the average numbers of preneoplastic or neoplastic lesions per unit length of basement membrane in rats given 100–1000 mg/kg/day ETBE were also comparable to control values. However, papillomatosis of the urinary bladder was found in 4 out of 30 rats (13%) in the group given 1000 mg/kg/day ETBE, and soft stones in the urinary bladder were found in 3 out of these 4 rats. The results thus demonstrated that ETBE did not exert promotional activity on urinary bladder carcinogenesis. However, papillomatosis of the urinary bladder developed in small numbers of the rats given ETBE at 1000 mg/kg/day but not in rats given 500 mg/kg/day or lower doses. PMID:24526807

  14. Effects of in utero di-butyl phthalate and butyl benzyl phthalate exposure on offspring development and male reproduction of rat.

    PubMed

    Ahmad, Rahish; Gautam, A K; Verma, Y; Sedha, S; Kumar, Sunil

    2014-02-01

    The study was conducted to assess the effects of in utero di-butyl phthalate (DBP) and butyl benzyl phthalate (BBP) exposure during late gestation on offspring's development and reproductive system of male rats. Pregnant rats were treated orally with DBP (2, 10, 50 mg/kg), BBP (4, 20, 100 mg/kg), and diethylstilbestrol (DES) 6 μg/kg (positive control) from GD14 to parturition. A significant reduction in dams' body weight on GD21 in DBP-, BBP-, and DES-treated groups was observed. The gestation length was considerably elevated in the treated groups. Decline in male pups' body weight was significant at PND75 in DBP- (50 mg/kg), BBP- (20,100 mg/kg), and DES-treated groups. The weight of most of the reproductive organs and sperm quality parameters was impaired significantly in DBP- (50 mg/kg) and BBP- (100 mg/kg) treated groups. Further, a non-significant decline in testicular spermatid count and daily sperm production was also monitored in treated groups. A significant reduction in serum testosterone level in BBP (100 mg/kg), whereas the testicular activity of 17β-HSD was declined non-significantly in the treated groups with respect to control. The data suggests that DBP and BBP exposure during late gestation period might have adverse effects on offspring's development, spermatogenesis, and steroidogenesis in adult rats.

  15. Combined toxicities of methyl tert-butyl ether and its metabolite tert-butyl alcohol on earthworms via different exposure routes.

    PubMed

    Lee, Woo-Mi; Yoon, Youngdae; An, Youn-Joo

    2015-06-01

    Methyl tert-butyl ether (MTBE) and tert-butyl alcohol (TBA) are among the major soil contaminants that threaten the health of soil ecosystems. Many MTBE-contaminated sites accumulate TBA, because TBA is the intermediate of MTBE biodegradation. To access the risk of MTBE and TBA in soil, we investigated the combined toxicities of MTBE and TBA using two earthworm species, Perionyx excavatus and Eisenia andrei, as well as the toxic effects via different exposure routes. The combined toxicity showed weak antagonistic effects (LC50mix values were slightly greater than 1.0), and sensitivity toward same pollutants differed in the two earthworm species. Moreover, the toxicity of MTBE and TBA was also affected by the exposure route; both filter paper and artificial soil tests showed that dermal-only exposure to MTBE had an even greater toxic effect than combined dermal and oral exposure. Thus, we suggest that diverse environmental factors including organic materials, the physicochemical properties of the contact media, and the exposure routes of the organism, should be taken into consideration when assessing the effects of pollutants on organisms in diverse environmental systems.

  16. New blends of ethylene-butyl acrylate copolymers with thermoplastic starch. Characterization and bacterial biodegradation.

    PubMed

    Morro, A; Catalina, F; Corrales, T; Pablos, J L; Marin, I; Abrusci, C

    2016-09-20

    Ethylene-butyl acrylate copolymer (EBA) with 13% of butyl acrylate content was used to produce blends with 10, 30 and 60% of thermoplastic starch (TPS) plasticized with glycerol. Ethylene-acrylic acid copolymer (EAA) was used as compatibilizer at 20% content with respect to EBA. The blends were characterized by X-ray diffraction, ATR-Fourier Transform Infrared Spectroscopy (ATR-FTIR), Scanning Electron Microscopy (SEM), water-Contact Angle measurements (CA), Differential Scanning Calorimetry (DSC) and Stress-strain mechanical tests. Initiated autoxidation of the polymer blends was studied by chemiluminescence (CL) confirming that the presence of the polyolefin-TPS interphase did not substantially affect the oxidative thermostability of the materials. Three bacterial species have been isolated from the blend films buried in soil and identified as Bacillus subtilis, Bacillus borstelensis and Bacillus licheniformis. Biodegradation of the blends (28days at 45°C) was evaluated by carbon dioxide measurement using the indirect impedance technique. PMID:27261731

  17. Biotransformation of methyl tert-butyl ether by human cytochrome P450 2A6.

    PubMed

    Shamsipur, Mojtaba; Miran Beigi, Ali Akbar; Teymouri, Mohammad; Poursaberi, Tahereh; Mostafavi, S Mojtaba; Soleimani, Parviz; Chitsazian, Fereshteh; Tash, Shahram Abolhassan

    2012-04-01

    Methyl tert-butyl ether (MTBE) is widely used as gasoline oxygenate and octane number enhancer for more complete combustion in order to reduce the air pollution caused by motor vehicle exhaust. The possible adverse effects of MTBE on human health are of major public concern. However, information on the metabolism of MTBE in human tissues is scarce. The present study demonstrates that human cytochrome P450 2A6 is able to metabolize MTBE to tert-butyl alcohol (TBA), a major circulating metabolite and marker for exposure to MTBE. As CYP2A6 is known to be constitutively expressed in human livers, we infer that it may play a significant role in metabolism of gasoline ethers in liver tissue. PMID:21915685

  18. Aging of Weapon Seals – An Update on Butyl O-ring Issues

    SciTech Connect

    Wilson, Mark H.

    2011-07-13

    During testing under the Enhanced Surveillance Campaign in 2001, preliminary data detected a previously unknown and potentially serious concern with recently procured butyl o-rings on several programs. All butyl o-rings molded from a proprietary formulation throughout the period circa 1999 through 2001 had less than a full cure. Engineering judgment was that under curing is detrimental and could possibly lead to sub-optimum performance or, in the worst case, premature seal failure. An aging study was undertaken to ensure that suspect o-rings installed in the stockpile will retain sufficient sealing force for a minimum ten-year service life. A new prediction model developed for this study indicates suspect o-rings do not need to be replaced before the ten-year service life. Long-term testing results are reported on a yearly basis to validate the prediction model. This report documents the aging results for the period September 2002 to January 2011.

  19. Recanalization of Splenic Artery Aneurysm After Transcatheter Arterial Embolization Using N-Butyl Cyanoacrylate

    SciTech Connect

    Matsumoto, Keiji; Ushijima, Yasuhiro Tajima, Tsuyoshi; Nishie, Akihiro; Hirakawa, Masakazu; Ishigami, Kousei; Yamaji, Yukiko; Honda, Hiroshi

    2010-02-15

    A 65-year-old woman who had been diagnosed as having microscopic polyangiitis developed sudden abdominal pain and entered a state of shock. Abdominal CT showed massive hemoperitoneum, and emergent angiography revealed a ruptured splenic artery aneurysm. After direct catheterization attempts failed due to tortuous vessels and angiospasm, transcatheter arterial embolization using an n-butyl cyanoacrylate (NBCA)-lipiodol mixture was successfully performed. Fifty days later, the patient developed sudden abdominal pain again. Repeated angiography demonstrated recanalization of the splenic artery and splenic artery aneurysm. This time, the recanalized aneurysm was embolized using metallic coils with the isolation method. Physicians should keep in mind that recanalization can occur after transcatheter arterial embolization using N-butyl cyanoacrylate, which has been used as a permanent embolic agent.

  20. Crystal structure of the co-crystal butyl-paraben-isonicotinamide (1/1).

    PubMed

    Bhardwaj, Rajni M; Yang, Huaiyu; Florence, Alastair J

    2016-01-01

    The title 1:1 co-crystal, C11H14O3·C6H6N2O [systematic name: butyl 4-hy-droxy-benzoate-isonicotinamide (1/1)], crystallizes with one mol-ecule of butyl-paraben (BPN) and one mol-ecule of isonicotinamide (ISN) in the asymmetric unit. In the crystal, BPN and ISN mol-ecules form hydrogen-bonded (O-H⋯N and N-H⋯O) dimers of paired BPN and ISN mol-ecules. These dimers are further connected to each other via N-H⋯O=C hydrogen bonds, creating ribbons in [011] which further stack along the a axis to form a layered structure with short C⋯C contacts of 3.285 (3) Å. Packing inter-actions within the crystal structure were assessed using PIXEL calculations. PMID:26870584

  1. Crystal structure of the co-crystal butyl­paraben–isonicotinamide (1/1)

    PubMed Central

    Bhardwaj, Rajni M.; Yang, Huaiyu; Florence, Alastair J.

    2016-01-01

    The title 1:1 co-crystal, C11H14O3·C6H6N2O [systematic name: butyl 4-hy­droxy­benzoate–isonicotinamide (1/1)], crystallizes with one mol­ecule of butyl­paraben (BPN) and one mol­ecule of isonicotinamide (ISN) in the asymmetric unit. In the crystal, BPN and ISN mol­ecules form hydrogen-bonded (O—H⋯N and N—H⋯O) dimers of paired BPN and ISN mol­ecules. These dimers are further connected to each other via N—H⋯O=C hydrogen bonds, creating ribbons in [011] which further stack along the a axis to form a layered structure with short C⋯C contacts of 3.285 (3) Å. Packing inter­actions within the crystal structure were assessed using PIXEL calculations. PMID:26870584

  2. Crystal structure of the co-crystal butyl-paraben-isonicotinamide (1/1).

    PubMed

    Bhardwaj, Rajni M; Yang, Huaiyu; Florence, Alastair J

    2016-01-01

    The title 1:1 co-crystal, C11H14O3·C6H6N2O [systematic name: butyl 4-hy-droxy-benzoate-isonicotinamide (1/1)], crystallizes with one mol-ecule of butyl-paraben (BPN) and one mol-ecule of isonicotinamide (ISN) in the asymmetric unit. In the crystal, BPN and ISN mol-ecules form hydrogen-bonded (O-H⋯N and N-H⋯O) dimers of paired BPN and ISN mol-ecules. These dimers are further connected to each other via N-H⋯O=C hydrogen bonds, creating ribbons in [011] which further stack along the a axis to form a layered structure with short C⋯C contacts of 3.285 (3) Å. Packing inter-actions within the crystal structure were assessed using PIXEL calculations.

  3. 21 CFR 526.820 - Erythromycin.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... (as the base), 0.45 milligram of butylated hydroxyanisole, and 0.45 milligram of butylated... (as the base), 0.90 milligram of butylated hydroxyanisole, and 0.90 milligram of butylated hydroxytoluene. (3) The vehicle is triglyceride of saturated fatty acids from coconut oil. (4) The drug may...

  4. 21 CFR 526.820 - Erythromycin.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... (as the base), 0.45 milligram of butylated hydroxyanisole, and 0.45 milligram of butylated... (as the base), 0.90 milligram of butylated hydroxyanisole, and 0.90 milligram of butylated hydroxytoluene. (3) The vehicle is triglyceride of saturated fatty acids from coconut oil. (4) The drug may...

  5. Enantioselective nitrile anion cyclization to substituted pyrrolidines. A highly efficient synthesis of (3S,4R)-N-tert-butyl-4-arylpyrrolidine-3-carboxylic acid.

    PubMed

    Chung, John Y L; Cvetovich, Raymond; Amato, Joseph; McWilliams, J Christopher; Reamer, Robert; DiMichele, Lisa

    2005-04-29

    [reaction: see text] A practical asymmetric synthesis of N-tert-butyl disubstituted pyrrolidines via a nitrile anion cyclization strategy is described. The five-step chromatography-free synthesis of (3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylic acid (2) from 2-chloro-1-(2,4-difluorophenyl)-ethanone achieved a 71% overall yield. The cyclization substrate was prepared via a catalytic CBS asymmetric reduction, t-butylamine displacement of the chlorohydrin, and a conjugate addition of the hindered secondary amine to acrylonitrile. The key nitrile anion 5-exo-tet cyclization concomitantly formed the pyrrolidine ring with clean inversion of the C-4 center to afford 1,3,4-trisubstituted chiral pyrrolidine in >95% yield and 94-99% ee. Diethyl chlorophosphate and lithium hexamethyldisilazide were shown to be the respective optimum activating group and base in this cyclization. The trans-cis mixture of the pyrrolidine nitrile undergoes a kinetically controlled epimerization/ saponification to afford the pure trans-pyrrolidine carboxylic acid target compound in >99.9% chemical and optical purity. This chemistry was also shown to be applicable to both electronically neutral and rich substituted phenyl substrates.

  6. Protective Effects of Rooibos (Aspalathus linearis) and/or Red Palm Oil (Elaeis guineensis) Supplementation on tert-Butyl Hydroperoxide-Induced Oxidative Hepatotoxicity in Wistar Rats

    PubMed Central

    Ajuwon, Olawale R.; Katengua-Thamahane, Emma; Van Rooyen, Jacques; Oguntibeju, Oluwafemi O.; Marnewick, Jeanine L.

    2013-01-01

    The possible protective effects of an aqueous rooibos extract (Aspalathus linearis), red palm oil (RPO) (Elaeis guineensis), or their combination on tert-butyl-hydroperoxide-(t-BHP-)induced oxidative hepatotoxicity in Wistar rats were investigated. tert-butyl hydroperoxide caused a significant (P < 0.05) elevation in conjugated dienes (CD) and malondialdehyde (MDA) levels, significantly (P < 0.05) decreased reduced glutathione (GSH) and GSH : GSSG ratio, and induced varying changes in activities of catalase, superoxide dismutase, glutathione peroxidase, and glutathione reductase in the blood and liver. This apparent oxidative injury was associated with histopathological changes in liver architecture and elevated levels of serum alanine aminotransferase (ALT), aspartate aminotransferase (AST), and lactate dehydrogenase (LDH). Supplementation with rooibos, RPO, or their combination significantly (P < 0.05) decreased CD and MDA levels in the liver and reduced serum level of ALT, AST, and LDH. Likewise, changes observed in the activities of antioxidant enzymes and impairment in redox status in the erythrocytes and liver were reversed. The observed protective effects when rooibos and RPO were supplemented concomitantly were neither additive nor synergistic. Our results suggested that rooibos and RPO, either supplemented alone or combined, are capable of alleviating t-BHP-induced oxidative hepatotoxicity, and the mechanism of this protection may involve inhibition of lipid peroxidation and modulation of antioxidants enzymes and glutathione status. PMID:23690869

  7. The chemical behavior of terminally tert-butylated polyolefins.

    PubMed

    Klein, Dagmar; Hopf, Henning; Jones, Peter G; Dix, Ina; Hänel, Ralf

    2015-01-01

    The chemical behavior of various oligoenes 2 has been studied. The catalytic hydrogenation of diene 3 yielded monoene 4. Triene 7 was hydrogenated to diene 8, monoene 9 and saturated hydrocarbon 10. Bromine addition to 3 and 7 yielded the dibromides 17 and 18, respectively, i.e., the oligoene system has been attacked at its terminal olefinic carbon atoms. Analogously, the higher vinylogs 19 and 20 yielded the 1,8- and 1,10-bromine adduts 23 and 24, respectively, when less than 1 equivalent of bromine was employed. Treatment of tetraene 19 with excess bromine provided tetrabromide 25. In epoxidation reactions, both with meta-chloroperbenzoic acid (MCPBA) and dimethyldioxirane (DMDO) two model oligoenes were studied: triene 7 and tetraene 19. Whereas 7 furnished the rearrangement product 31 with MCPBA, it yielded the symmetrical epoxide 32 with DMDO. Analogously, 19 was converted to mono-epoxide 33 with MCPBA and to 34 with DMDO. Diels-Alder addition of 7 with N-phenyltriazolinedione (PTAD) did not take place. Extension of the conjugated π-system to the next higher vinylog, 19, caused NPTD-addition to the symmetrical adduct 37 in good yield. Comparable results were observed on adding NPTD (equivalent amount) to pentaene 20 and hexaene 21. Using 36 in excess provided the 2:1-adduct 40 from 21 and led to a complex mixture of adducts from heptaene 22. With tetracyanoethylene (TCNE) as the dienophile, tetraolefin 19 yielded the symmetrical adduct 43, although the reaction temperature had to be increased. Pentaene 20 and hexaene 21 led to corresponding results, adducts 44 and 45 being produced in acceptable yields. With nonaene 42 and TCNE the 2:1-adduct 48 was generated according to its spectroscopic data. Exploratory photochemical studies were carried out with tetraene 19 as the model compound. On irradiation this reacted with oxygen to the stable endo-peroxide 52.

  8. 2,6-Di-tert-butyl-4-(morpholinometh­yl)­phenol monohydrate

    PubMed Central

    Zeng, Tao; Ren, Wan-Zhong

    2008-01-01

    In the title compound, C19H31NO2·H2O, the morpholine ring adopts a chair conformation, while the phenolic hydroxyl group is sterically hindered by the adjacent tert-butyl groups. The crystal structure is stabilized by a number of O—H⋯O, O—H⋯N and C—H⋯O hydrogen-bonding inter­actions, involving both the organic and the solvent mol­ecules. PMID:21201434

  9. The antioxidant methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate.

    PubMed

    Li, Xiang; Wang, Zhi-Gang; Chen, Hou-He; Liu, Sheng-Gao

    2014-11-01

    The title compound, C18H28O3, was prepared by the reaction of 2,6-di-tert-butylphenol with methyl acrylate under basic conditions using dimethyl sulfoxide as the promoter. The structure of this antioxidant indicates significant strain between the ortho tert-butyl substituents and the phenolic OH group. In spite of the steric crowding of the OH group, it participates in intermolecular hydrogen bonding with the ester carbonyl O atom. PMID:25370105

  10. Crystal structures of three complexes of zinc chloride with tri-tert-butyl­phosphane

    PubMed Central

    Finke, Aaron D.; Gray, Danielle L.; Moore, Jeffrey S.

    2016-01-01

    Under anhydrous conditions and in the absence of a Lewis-base solvent, a zinc chloride complex with tri-tert-butyl­phosphane as the μ-bridged dimer is formed, viz. di-μ-chlorido-bis­[chlorido­bis­(tri-tert-butyl­phosphane)zinc], [ZnCl4(C12H27P)2], (1), which features a nearly square-shaped (ZnCl)2 cyclic core and whose Cl atoms inter­act weakly with C—H groups on the phosphane ligand. In the presence of THF, monomeric di­chlorido­(tetra­hydro­furan-κO)(tri-tert-butyl­phosphane-κP)zinc, [ZnCl2(C4H8O)(C12H27P)] or [P(tBu3)(THF)ZnCl2], (2), is formed. This slightly distorted tetra­hedral Zn complex has weak C—H⋯Cl inter­actions between the Cl atoms and phosphane and THF C—H groups. Under ambient conditions, the hydrolysed complex tri-tert-butyl­phospho­nium aqua­tri­chlorido­zincate 1,2-di­chloro­ethane monosolvate, (C12H28P)[ZnCl3(H2O)]·C2H4Cl2 or [HPtBu3]+ [(H2O)ZnCl3]−·C2H4Cl2, (3), is formed. This complex forms chains of [(H2O)ZnCl3]− anions from hydrogen-bonding inter­actions between the water H atoms and Cl atoms that propagate along the b axis. PMID:26870580

  11. Synthesis of sulfonic acid derivatives by oxidative deprotection of thiols using tert-butyl hypochlorite.

    PubMed

    Joyard, Yoann; Papamicaël, Cyril; Bohn, Pierre; Bischoff, Laurent

    2013-05-01

    Starting from alkyl halides or Michael acceptors, thioacetates were prepared in situ and further treated with t-BuOCl, affording the corresponding sulfonyl chlorides which were trapped with nucleophiles such as water, alcohol, or amines. The three steps can be achieved in a one-pot procedure. Oxidative deprotection also proved to be efficient with S-trityl and S-tert-butyl groups, making it a convenient route toward cysteic acid derivatives.

  12. The antioxidant methyl 3-(3,5-di-tert-butyl-4-hydroxyphenyl)propionate.

    PubMed

    Li, Xiang; Wang, Zhi-Gang; Chen, Hou-He; Liu, Sheng-Gao

    2014-11-01

    The title compound, C18H28O3, was prepared by the reaction of 2,6-di-tert-butylphenol with methyl acrylate under basic conditions using dimethyl sulfoxide as the promoter. The structure of this antioxidant indicates significant strain between the ortho tert-butyl substituents and the phenolic OH group. In spite of the steric crowding of the OH group, it participates in intermolecular hydrogen bonding with the ester carbonyl O atom.

  13. Reverse osmosis performance with solutions containing tri-n-butyl phosphate

    SciTech Connect

    Siler, J.L.

    1991-10-22

    Tests were conducted to determine whether the reverse osmosis (RO) units at the F/H Effluent Treatment Facility (ETF) at the Savannah River could be made to process solutions containing tri-n-butyl phosphate (TBP). It was desired to test whether operation at a feed pH other than neutral would improve performance. Test results are discussed in this report and indicate that little improvement in the water flux can be expected at other pH values.

  14. Use of a Balloon and N-Butyl-2-Cyanoacrylate for Treatment of Arteriovenous Fistula

    SciTech Connect

    Doenmez, Halil Mavili, Ertugrul; Toker, Birguel; Oztuerk, M. Halil; Soylu, Serra O.; Hekimoglu, Baki

    2008-07-15

    We report a patient who developed a large arteriovenous fistula in right lower extremity after gunshot injury. Because other endovascular methods failed, the patient was successfully treated with concomitant use of detachable latex balloon and N-butyl-2-cyanoacrylate (NBCA). The combination of detachable balloon and NBCA can be effectively used for endovascular treatment of peripheral arteriovenous fistulas in selected cases when effective embolization could not be achieved with other embolizing agents or their various combinations.

  15. Free radical involvement in the oxidative phenomena induced by tert-butyl hydroperoxide in erythrocytes.

    PubMed

    Thornalley, P J; Trotta, R J; Stern, A

    1983-08-23

    Free radical involvement in the oxidative events induced by tert-butyl hydroperoxide in erythrocytes has been demonstrated by the use of the electron spin resonance technique of spin trapping with the spin trap 5.5-dimethyl-1-pyrroline-N-oxide (DMPO). The reactions of tert-butyl hydroperoxide with haemoglobins and intact cell systems were studied. Oxyhaemoglobin-containing system showed exclusive production of the t-butyloxy radical spin adduct of DMPO (DMPO-OBut), indicating t-butyloxy radical production. Methaemoglobin-containing systems showed the production of an oxidised derivative of DMPO, 5,5-dimethyl-2-ketopyrrolidino-1-oxyl (DMPOX)-previously associated with the generation of highly oxidised haem-iron. Carbon monoxyhaemoglobin-containing systems show the production of both DMPO-OBut and DMPOX but markedly slower than in either of the other haemoglobin systems. Generally, free radical production in haemoglobin systems was faster than in intact cell systems, indicating a membrane transport rate-limiting step for the tert-butyl hydroperoxide-mediated effects. Data from the use of free radical scavengers to inhibit DMPO-OBut production was consistent with the known reactivities of the scavengers toward t-butyloxy radicals. These and previously reported results (Trotta, R. J., Sullivan, S. G. and Stern, A. (1981) Biochim. Biophys. Acta 679, 230-237 and (1982) Biochem. J. 204, 405-415) implicate important roles for t-butyloxy radicals and haem intermediates in tert-butyl hydroperoxide-induced lipid peroxidation and haemoglobin oxidation in erythrocytes, respectively.

  16. 40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

    Code of Federal Regulations, 2013 CFR

    2013-07-01

    ... ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2...-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2′-(1,2-diazenediyl)bis - and 2,2... butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2),...

  17. 40 CFR 721.10326 - 2-Propenoic acid, 2-methyl-, methyl ester, polymer with butyl 2-propenoate, ethyl 2-propenoate...

    Code of Federal Regulations, 2014 CFR

    2014-07-01

    ... ester, polymer with butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2...-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2), 2,2′-(1,2-diazenediyl)bis - and 2,2... butyl 2-propenoate, ethyl 2-propenoate, zinc 2-methyl-2-propenoate (1:2) and zinc 2-propenoate (1:2),...

  18. Identification of tert-Butyl Cations in Zeolite H-ZSM-5: Evidence from NMR Spectroscopy and DFT Calculations.

    PubMed

    Dai, Weili; Wang, Chuanming; Yi, Xianfeng; Zheng, Anmin; Li, Landong; Wu, Guangjun; Guan, Naijia; Xie, Zaiku; Dyballa, Michael; Hunger, Michael

    2015-07-20

    Experimental evidence for the presence of tert-butyl cations, which are important intermediates in acid-catalyzed heterogeneous reactions, on solid acids has still not been provided to date. By combining density functional theory (DFT) calculations with (1)H/(13)C magic-angle-spinning NMR spectroscopy, the tert-butyl cation was successfully identified on zeolite H-ZSM-5 upon conversion of isobutene by capturing this intermediate with ammonia. PMID:26096840

  19. Fragrance material review on 2-methyl-4-phenyl-2-butyl acetate.

    PubMed

    McGinty, D; Letizia, C S; Api, A M

    2012-09-01

    A toxicologic and dermatologic review of 2-methyl-4-phenyl-2-butyl acetate when used as a fragrance ingredient is presented. 2-Methyl-4-phenyl-2-butyl acetate is a member of the fragrance structural group Aryl Alkyl Alcohol Simple Acid Esters (AAASAE). The AAASAE fragrance ingredients are prepared by reacting an aryl alkyl alcohol with a simple carboxylic acid (a chain of 1-4 carbons) to generate formate, acetate, propionate, butyrate, isobutyrate and carbonate esters. This review contains a detailed summary of all available toxicology and dermatology papers that are related to this individual fragrance ingredient and is not intended as a stand-alone document. Available data for 2-methyl-4-phenyl-2-butyl acetate were evaluated then summarized and includes physical properties, acute toxicity, skin irritation, skin sensitization, and elicitation data. A safety assessment of the entire AAASAE will be published simultaneously with this document. Please refer to Belsito et al. (2012) for an overall assessment of the safe use of this material and all AAASAE in fragrances.

  20. Comprehensive testing to measure the response of butyl rubber to Hanford tank waste simulant

    SciTech Connect

    NIGREY,PAUL J.

    2000-05-01

    This report presents the findings of the Chemical Compatibility Program developed to evaluate plastic packaging components that may be incorporated in packaging mixed-waste forms for transportation. Consistent with the methodology outlined in this report, the authors performed the second phase of this experimental program to determine the effects of simulant Hanford tank mixed wastes on packaging seal materials. That effort involved the comprehensive testing of five plastic liner materials in an aqueous mixed-waste simulant. The testing protocol involved exposing the materials to {approximately}143, 286, 571, and 3,670 krad of gamma radiation and was followed by 7-, 14-, 28-, 180-day exposures to the waste simulant at 18, 50, and 60 C. Butyl rubber samples subjected to the same protocol were then evaluated by measuring seven material properties: specific gravity, dimensional changes, mass changes, hardness, compression set, vapor transport rates, and tensile properties. From the analyses, they determined that butyl rubber has relatively good resistance to radiation, this simulant, and a combination of these factors. These results suggest that butyl rubber is a relatively good seal material to withstand aqueous mixed wastes having similar composition to the one used in this study.

  1. Antiproliferative effects of n-butyl-β-D-fructofuranoside from Kangaisan on Bel-7402 cells

    PubMed Central

    Lu, Ping; Li, Miao; Lou, Yiceng; Su, Fengping; Li, Hongling; Zhao, Xiang; Cheng, Yali

    2014-01-01

    Aims: Kangaisan is a powdered compound prescription of Traditional Chinese Medicine which has been used in cancers for many years in Hubei province, China. The purpose of this study was to investigate the antitumor effects of Kangaisan and screen bioactive components. Materials and Methods: 3-(4,5-Dimethythiazol-2-yl)-2,5 diphenyl-tetrazolium bromide (MTT) assay, flow cytometry, DNA (Deoxyribonucleic acid) fragmentation assay, Western blot, and real time-polymerase chain reaction were used to investigate the antiproliferation effect of n-butyl-β-D-fructofuranoside on Bel-7402 cells. Statistical Analysis: All experiments were performed in triplicate and the results were expressed as mean ± standard deviation. Statistical analysis was performed with analysis of variance using Origin 8.0 software. Results: It was illustrated that treatment of Bel-7402 cells with various concentrations of n-butyl-β-D-fructofuranoside resulted in growth inhibition in both a dose-dependent and time-dependent manner. The arrest of G0/G1 phase was also induced (P < 0.05). The increasing of sub-G1 cell population indicated the apoplectic characteristic (P < 0.05). Furthermore, the emerging of DNA fragmentation and the increase of Bax/Bcl-2 ratio and p53 expression suggested the possible mitochondrial apoptotic pathway (P < 0.05). Conclusions: The results illustrate that Kangaisan showed anticancer effects and n-butyl-β-D-fructofuranoside extracted from Kangaisan can suppress Bel-7402 cells via interfering cell cycle and by inducing apoptosis. PMID:24550588

  2. Identification of mercury methylation product by tert-butyl compounds in aqueous solution under light irradiation.

    PubMed

    Chen, Baowei; Chen, Ping; He, Bin; Yin, Yongguang; Fang, Linchuan; Wang, Xiaowei; Liu, Hongtao; Yang, Lihua; Luan, Tiangang

    2015-09-15

    The methylation of mercury (Hg) is of great concern as methylmercury (MeHg), the most toxic species, is produced. This study examined the possibilities of tert-butyl compounds (tert-butyl alcohol (TBA) and tert-butyl hydroperoxide (TBH)) and other alcohols serving as methyl donors for Hg photo-methylation under light irradiation. The yield of MeHg varied among the methyl donors, and it was also significantly influenced by salinity and pH. MeHg could be generated in the presence of TBH under visible light irradiation. The hydroxyl radical (OH) was found to promote MeHg production at low levels, but degrade MeHg in excess. The photo-production of MeHg was tentatively proposed via the complexation of Hg and methyl donors, the formation of an intermediate (O(Hg)C(CH3)3), and the intramolecular methyl transfer from methyl donors to Hg. This study implicates photoreactions between Hg and organic pollutants in understanding the fate and transformation of Hg in the aquatic environment.

  3. Experimental study on the enhancement of the neurotoxicity of methyl n-butyl ketone by non-neurotoxic aliphatic monoketones.

    PubMed Central

    Misumi, J; Nagano, M

    1985-01-01

    The neurotoxicity of methyl n-butyl ketone is known to be enhanced by combination with methyl ethyl ketone. This study was conducted to clarify the potentiating effect of aliphatic monoketones on the neurotoxicity of methyl n-butyl ketone. Rats were subcutaneously injected in the back with 4 mmol/kg/day of methyl ethyl ketone, methyl n-propyl ketone, methyl n-amyl ketone, or methyl n-hexyl ketone mixed with an equimolar dose of methyl n-butyl ketone five days a week for 20 weeks. The maximum motor fibre conduction velocity and the distal latency were measured every two weeks in the tail nerves of the treated animals and controls. All the monoketones tested enhanced the neurotoxicity of methyl n-butyl ketone. Of the compounds tested, methyl n-hexyl ketone, which had the longest carbon chain, enhanced the neurotoxicity of methyl n-butyl ketone most strongly. These results suggest that the length of the carbon chain of the aliphatic monoketones combined with methyl n-butyl ketone was related to the enhancement of the neurotoxicity of the neurotoxic compound. PMID:3970879

  4. Soil adsorption studies of a rice herbicide, cyhalofop-butyl, in two texturally different soils of India.

    PubMed

    Sondhia, Shobha; Khare, Rishi Raj

    2014-10-01

    The ability of herbicides to be adsorbed by the soil and sediment and their tendency to be desorbed are some of the most important factors affecting soil and water contamination. Therefore, a sorption study was conducted to evaluate the adsorption of cyhalofop-butyl, butyl (2R)-2-[4-(4-cyano-2-fluorophenoxy) phenoxy] propanoate, in the sandy clay loam and clayey soils using a batch equilibrium method. The adsorption of cyhalofop-butyl was found positively related with the clay and organic carbon content. Freundlich constants (Kf) of cyhalofop-butyl in the clayey and sandy clay loam were found to be 13.39 and 2.21, respectively. Sorption coefficients (Koc) and distribution coefficients (Kd) were found to be 265.38 and 2,092.79, and 1.38 and 11.48, for sandy clay loam and clayey soils, respectively. The adsorption isotherm suggested a relatively higher affinity of cyhalofop-butyl to the adsorption sites at low equilibrium concentrations. The low value of the soil organic carbon partition coefficient (Koc) of cyhalofop-butyl in the sandy loam soil suggested its weaker adsorption in soil and thus increased its risk of mobility into water sources; hence, it should be used judiciously to prevent groundwater contamination.

  5. Soil adsorption studies of a rice herbicide, cyhalofop-butyl, in two texturally different soils of India.

    PubMed

    Sondhia, Shobha; Khare, Rishi Raj

    2014-10-01

    The ability of herbicides to be adsorbed by the soil and sediment and their tendency to be desorbed are some of the most important factors affecting soil and water contamination. Therefore, a sorption study was conducted to evaluate the adsorption of cyhalofop-butyl, butyl (2R)-2-[4-(4-cyano-2-fluorophenoxy) phenoxy] propanoate, in the sandy clay loam and clayey soils using a batch equilibrium method. The adsorption of cyhalofop-butyl was found positively related with the clay and organic carbon content. Freundlich constants (Kf) of cyhalofop-butyl in the clayey and sandy clay loam were found to be 13.39 and 2.21, respectively. Sorption coefficients (Koc) and distribution coefficients (Kd) were found to be 265.38 and 2,092.79, and 1.38 and 11.48, for sandy clay loam and clayey soils, respectively. The adsorption isotherm suggested a relatively higher affinity of cyhalofop-butyl to the adsorption sites at low equilibrium concentrations. The low value of the soil organic carbon partition coefficient (Koc) of cyhalofop-butyl in the sandy loam soil suggested its weaker adsorption in soil and thus increased its risk of mobility into water sources; hence, it should be used judiciously to prevent groundwater contamination. PMID:24875347

  6. N-Butyl sulfide as an attractant and coattractant for male and female codling moth (Lepidoptera: Tortricidae).

    PubMed

    Landolt, Peter J; Ohler, Bonnie; Lo, Peter; Cha, Dong; Davis, Thomas S; Suckling, David M; Brunner, Jay

    2014-04-01

    Research to discover and develop attractants for the codling moth, Cydia pomonella L., has involved identification of the chemicals eliciting moth orientation to conspecific female moths, host fruits, fermented baits, and species of microbes. Pear ester, acetic acid, and N-butyl sulfide are among those chemicals reported to attract or enhance attractiveness to codling moth. We evaluated the trapping of codling moth with N-butyl sulfide alone and in combination with acetic acid and pear ester in apple orchards. Acetic acid was attractive in two tests and N-butyl sulfide was attractive in one of two tests. N-Butyl sulfide increased catches of codling moth when used with acetic acid to bait traps. N-Butyl sulfide also increased catches of codling moth when added to traps baited with the combination of acetic acid and pear ester. Male and female codling moth both responded to these chemicals and chemical combinations. These results provide a new three-component lure comprising N-butyl sulfide, acetic acid, and pear ester that is stronger for luring codling moth females than other attractants tested.

  7. Enhanced ozonation degradation of di-n-butyl phthalate by zero-valent zinc in aqueous solution: performance and mechanism.

    PubMed

    Wen, Gang; Wang, Sheng-Jun; Ma, Jun; Huang, Ting-Lin; Liu, Zheng-Qian; Zhao, Lei; Su, Jun-Feng

    2014-01-30

    Enhanced ozonation degradation of di-n-butyl phthalate (DBP) by zero-valent zinc (ZVZ) has been investigated using a semi-continuous reactor in aqueous solution. The results indicated that the combination of ozone (O3) and ZVZ showed an obvious synergetic effect, i.e. an improvement of 54.8% on DBP degradation was obtained by the O3/ZVZ process after 10min reaction compared to the cumulative effect of O3 alone and O2/ZVZ. The degradation efficiency of DBP increased gradually with the increase of ZVZ dosage, enhanced as solution pH increasing from 2.0 to 10.0, and more amount of DBP was degraded with the initial concentration of DBP arising from 0.5 to 2.0mgL(-1). Recycling use of ZVZ resulted in the enhancement of DBP degradation, because the newly formed zinc oxide took part in the reaction. The mechanism investigation demonstrated that the enhancement effect was attributed to the introduction of ZVZ, which could promote the utilization of O3, enhance the formation of superoxide radical by reducing O2 via one-electron transfer, accelerate the production of hydrogen peroxide and the generation of hydroxyl radical. Additionally, the newly formed zinc oxide on ZVZ surface also contributed to the enhancement of DBP degradation in the recycling use of ZVZ. Most importantly, the O3/ZVZ process was also effective in enhanced ozonation degradation of DBP under the background of actual waters.

  8. Photodynamic Therapy with Hexa(sulfo-n-butyl)[60]Fullerene Against Sarcoma In Vitro and In Vivo.

    PubMed

    Yu, Chi; Avci, Pinar; Canteenwala, Taizoon; Chiang, Long Y; Chen, Bao J; Hamblin, Michael R

    2016-01-01

    The hydrophilic molecular micellar hexa(sulfo-n-butyl)[60]fullerene (FC₄S), first synthesized in 1998 as a photosensitizer (PS) has been reported to exhibit high efficacy for singlet oxygen generation and antimicrobial photodynamic inactivation. The purpose of this study was to investigate the effects of photoactivated FC₄S for free radical generation and to mediate photodynamic therapy (PDT) of cancer in vitro and in vivo. The results demonstrated that following light irradiation, FC4S produced singlet oxygen, but after addition of electron donors such as ferrocytochrome c or NADH, FC4S also produced superoxide. The combination of FC4S with light irradiation was able to induce cytotoxicity to human fibrosarcoma cells and murine sarcoma 180 cells in vitro. Cell-killing was proportional to fluence as well as FC4S concentration. Photoirradiation by argon-ion laser after intraperitoneal injection of FC4S also resulted in inhibition of S180 tumor growth in vivo (up to 80% reduction of tumor volume). Hematological and blood biochemistry parameters of the cancer-bearing mice were improved by PDT. Based on these findings, we conclude that FC₄S has a great potential as a nanomedicine in PDT for cancer. PMID:27398442

  9. Aldh2 knockout mice were more sensitive to DNA damage in leukocytes due to ethyl tertiary butyl ether exposure.

    PubMed

    Weng, Zuquan; Suda, Megumi; Ohtani, Katsumi; Mei, Nan; Kawamoto, Toshihiro; Nakajima, Tamie; Wang, Rui-Sheng

    2011-01-01

    To clarify the genotoxicity of ethyl tertiary butyl ether (ETBE), a gasoline additive, male and female C57BL/6 mice of Aldh2+/+ and Aldh2-/- genotypes, aged 8 wk, were exposed to 0, 500, 1,750, or 5,000 ppm ETBE for 6 h/day, 5 d per week for 13 wk. DNA damage in leukocytes was measured by the alkaline comet assay and expressed quantitatively as Tail Intensity (TI). For male mice, TI was significantly higher in all three groups exposed to ETBE than in those without exposure within Aldh2-/- mice, whereas within Aldh2+/+ mice, TI increased only in those exposed to 5,000 ppm of ETBE as compared with mice without exposure. For female mice, a significant increase in TI values was observed in the group exposed to 5,000 ppm of ETBE as compared with those without exposure within Aldh2-/- mice; TI in Aldh2-/- mice exposed to 1,750 and 5,000 ppm was significantly higher than in Aldh2+/+ mice without exposure. TI did not significantly increase in any of the groups exposed to ETBE within female Aldh2+/+ mice. Based on the results we suggest that Aldh2-/- mice are more sensitive to DNA damage caused by ETBE than Aldh2+/+ mice and that males seem more susceptible to this effect than females. PMID:21372431

  10. Health Risk Assessment for Inhalation Exposure to Methyl Tertiary Butyl Ether at Petrol Stations in Southern China.

    PubMed

    Hu, Dalin; Yang, Jianping; Liu, Yungang; Zhang, Wenjuan; Peng, Xiaowu; Wei, Qinzhi; Yuan, Jianhui; Zhu, Zhiliang

    2016-02-01

    Methyl tertiary butyl ether (MTBE), a well known gasoline additive, is used in China nationwide to enhance the octane number of gasoline and reduce harmful exhaust emissions, yet little is known regarding the potential health risk associated with occupational exposure to MTBE in petrol stations. In this study, 97 petrol station attendants (PSAs) in southern China were recruited for an assessment of the health risk associated with inhalation exposure to MTBE. The personal exposure levels of MTBE were analyzed by Head Space Solid Phase Microextraction GC/MS, and the demographic characteristics of the PSAs were investigated. Cancer and non-cancer risks were calculated with the methods recommended by the United States Environmental Protection Agency. The results showed that the exposure levels of MTBE in operating workers were much higher than among support staff (p < 0.01) and both were lower than 50 ppm (an occupational threshold limit value). The calculated cancer risks (CRs) at the investigated petrol stations was 0.170 to 0.240 per 10⁶ for operating workers, and 0.026 to 0.049 per 10⁶ for support staff, which are below the typical target range for risk management of 1 × 10(-6) to 1 × 10(-4); The hazard quotients (HQs) for all subjects were <1. In conclusion, our study indicates that the MTBE exposure of PSAs in southern China is in a low range which does not seem to be a significant health risk. PMID:26861375

  11. The efficient photocatalytic degradation of methyl tert-butyl ether under Pd/ZnO and visible light irradiation.

    PubMed

    Seddigi, Zaki S; Ahmed, Saleh A; Bumajdad, Ali; Danish, Ekram Y; Shawky, Ahmed M; Gondal, Mohammed A; Soylak, Mustafa

    2015-01-01

    Methyl tert-butyl ether is a commonly used fuel oxygenate that is present in gasoline. It was introduced to eliminate the use of leaded gasoline and to improve the octane quality because it aids in the complete combustion of fuel by supplying oxygen during the combustion process. Over the past decade, the use of MTBE has increased tremendously worldwide. For obvious reasons relating to accidental spillage, MTBE started to appear as an environmental and human health threat because of its nonbiodegradable nature and carcinogenic potential, respectively. In this work, MTBE was degraded with the help of an advanced oxidation process through the use of zinc oxide as a photocatalyst in the presence of visible light. A mixture of 200 mg of zinc oxide in 350 mL of 50 ppm MTBE aqueous solution was irradiated with visible light for a given time. The complete degradation of MTBE was recorded, and approximately 99% photocatalytic degradation of 100 ppm MTBE solution was observed. Additionally, the photoactivity of 1% Pd-doped ZnO was tested under similar conditions to understand the effect of Pd doping on ZnO. Our results obtained under visible light irradiation are very promising, and they could be further explored for the degradation of several nondegradable environmental pollutants.

  12. Construction of wettability gradient surface on copper substrate by controlled hydrolysis of poly(methyl methacrylate-butyl acrylate) films

    NASA Astrophysics Data System (ADS)

    Zhang, Yong; Cheng, Jiang; Yang, Zhuo-ru

    2014-10-01

    We report a gradient wettability surface on copper slide prepared by a simple controlled ester group hydrolysis procedure of poly(methyl methacrylate-butyl acrylate) [P (MMA-BA)] films coated on the copper substrate. In the method, sodium hydroxide solutions are selected to prepare surface gradient wettability on P (MMA-BA) films. The P (MMA-BA) copolymers with different MMA contents are first synthesized by a conventional free atom radical solution polymerization method. The transfer of surface chemical composition from the ester group to acid salt is achieved by hydrolysis in NaOH solution. The effects of different concentrations of NaOH solution and reaction times on the physicochemical properties of the resulting surfaces are studied. The field-emission scanning electron microscopy (FESEM), atomic force microscopy (AFM) and X-ray photoelectron spectroscopy (XPS) results show that the varying concentration along the substrate length is only attributed to the hydrolysis reaction of ester groups. The hydrolysis causes insignificant change on the morphology of the original film on the copper substrate. In addition, it is found that the MMA copolymer content has a significant influence on the concentration of ester groups on the outermost surface and thus important for forming the slope gradients.

  13. Health Risk Assessment for Inhalation Exposure to Methyl Tertiary Butyl Ether at Petrol Stations in Southern China.

    PubMed

    Hu, Dalin; Yang, Jianping; Liu, Yungang; Zhang, Wenjuan; Peng, Xiaowu; Wei, Qinzhi; Yuan, Jianhui; Zhu, Zhiliang

    2016-02-06

    Methyl tertiary butyl ether (MTBE), a well known gasoline additive, is used in China nationwide to enhance the octane number of gasoline and reduce harmful exhaust emissions, yet little is known regarding the potential health risk associated with occupational exposure to MTBE in petrol stations. In this study, 97 petrol station attendants (PSAs) in southern China were recruited for an assessment of the health risk associated with inhalation exposure to MTBE. The personal exposure levels of MTBE were analyzed by Head Space Solid Phase Microextraction GC/MS, and the demographic characteristics of the PSAs were investigated. Cancer and non-cancer risks were calculated with the methods recommended by the United States Environmental Protection Agency. The results showed that the exposure levels of MTBE in operating workers were much higher than among support staff (p < 0.01) and both were lower than 50 ppm (an occupational threshold limit value). The calculated cancer risks (CRs) at the investigated petrol stations was 0.170 to 0.240 per 10⁶ for operating workers, and 0.026 to 0.049 per 10⁶ for support staff, which are below the typical target range for risk management of 1 × 10(-6) to 1 × 10(-4); The hazard quotients (HQs) for all subjects were <1. In conclusion, our study indicates that the MTBE exposure of PSAs in southern China is in a low range which does not seem to be a significant health risk.

  14. Speciated hydrocarbon and carbon monoxide emissions from an internal combustion engine operating on methyl tertiary butyl ether-containing fuels.

    PubMed

    Poulopoulos, S G; Philippopoulos, C J

    2001-07-01

    In the present work, engine and tailpipe (after a three-way catalytic converter) emissions from an internal combustion engine operating on two oxygenated blend fuels [containing 2 and 11% weight/weight (w/w) methyl tertiary butyl ether (MTBE)] and on a nonoxygenated base fuel were characterized. The engine (OPEL 1.6 L) was operated under various conditions, in the range of 0-20 HP. Total unburned hydrocarbons, carbon monoxide, methane, hexane, ethylene, acetaldehyde, acetone, 2-propanol, benzene, toluene, 1,3-butadiene, acetic acid, and MTBE were measured at each engine operating condition. As concerns the total HC emissions, the use of MTBE was beneficial from 1.90 to 3.81 HP, which were by far the most polluting conditions. Moreover, CO emissions in tailpipe exhaust were decreased in the whole operation range with increasing MTBE in the fuel. The greatest advantage of MTBE addition to gasoline was the decrease in ethylene, acetaldehyde, benzene, toluene, and acetic acid emissions in engine exhaust, especially when MTBE content in the fuel was increased to 11% w/w. In tailpipe exhaust, the catalyst operation diminished the observed differences. Ethylene, methane, and acetaldehyde were the main compounds present in exhaust gases. Ethylene was easily oxidized over the catalyst, while acetaldehyde and methane were quite resistant to oxidation.

  15. The genotoxic and cytotoxic effects of 1-butyl-3-methylimidazolium chloride in soil on Vicia faba seedlings.

    PubMed

    Liu, Tong; Zhu, Lusheng; Wang, Jinhua; Wang, Jun; Xie, Hui

    2015-03-21

    Although considered as "green" solvents, the toxic effects of ionic liquids (ILs) on organisms have been widely investigated in recent years. However, studies on the toxic effects of ILs on plants all focus on toxicity in nutrient solution. In the present paper, the toxic effects of 1-butyl-3-methylimidazolium chloride ([C4mim]Cl) on Vicia faba seedlings in soil at 0, 500, 1500, and 2500 mg kg(-1) on day 10 were studied. The present results showed that the growth of V. faba seedlings may be seriously inhibited when the IL concentrations were higher than 500 mg kg(-1). The EC50 values for shoot length, root length, and dry weight were 3886, 2483, and 3359 mg kg(-1), respectively. In addition, [C4mim]Cl caused lipid peroxidation and DNA damage at 500 mg kg(-1) and oxidative stress at 1500 mg kg(-1), which indicated that [C4mim]Cl may have genotoxicity and cytotoxicity on V. faba seedlings. Moreover, oxidative damage may be the main toxic mechanism of ILs.

  16. Fast detection of methyl tert-butyl ether from water using solid phase microextraction and ion mobility spectrometry.

    PubMed

    Nousiainen, Marjaana; Holopainen, Sanna; Puton, Jaroslaw; Sillanpää, Mika

    2011-05-15

    Methyl tert-butyl ether (MTBE) is commonly used as chemical additive to increase oxygen content and octane rating of reformulated gasoline. Despite its impact on enhancing cleaner combustion of gasoline, MTBE poses a threat to surface and ground water when gasoline is released into the environment. Methods for onsite analysis of MTBE in water samples are also needed. A less common technique for MTBE detection from water is ion mobility spectrometry (IMS). We describe a method for fast sampling and screening of MTBE from water by solid phase microextraction (SPME) and IMS. MTBE is adsorbed from the head space of a sample to the coating of SPME fiber. The interface containing a heated sample chamber, which couples SPME and IMS, was constructed and the SPME fiber was introduced into the sample chamber for thermal desorption and IMS detection of MTBE vapors. The demonstrated SPME-IMS method proved to be a straightforward method for the detection of trace quantities of MTBE from waters including surface and ground water. We determined the relative standard deviation of 8.3% and detection limit of 5 mg L(-1) for MTBE. Because of short sampling, desorption, and detection times, the described configuration of combined SPME and IMS is a feasible method for the detection of hazardous substances from environmental matrices.

  17. Percutaneous absorption of 2,6-di-tert-butyl-4-nitrophenol (DBNP) in isolated perfused porcine skin.

    PubMed

    Inman, Alfred O; Still, Kenneth R; Jederberg, Warren W; Carpenter, Robert L; Riviere, Jim E; Brooks, James D; Monteiro-Riviere, Nancy A

    2003-06-01

    DBNP (2,6-di-tert-butyl-4-nitrophenol) has been reported as a potential contaminant in submarines. This yellow substance forms when lubrication oil mist containing the antioxidant additive 2,6-di-tert-butylphenol passes through an electrostatic precipitator and is nitrated. Percutaneous absorption of 14C-DBNP was assessed in the isolated perfused porcine skin flap (IPPSF). Four treatments were studied (n=4 flaps/treatment): 40.0 microgram/cm(2) in 100% ethanol; 40.0 microgram/cm(2) in 85% ethanol/15% H(2)O; 4.0 microgram/cm(2) in 100% ethanol; and 4.0 microgram/cm(2) in 85% ethanol/15% water. DBNP absorption was minimal across all treatment groups, with the highest absorption detected being only 1.08% applied dose in an aqueous ethanol group. The highest mass of 14C-DBNP absorbed was only 0.5 microgram. The majority of the applied dose remained on the surface of the skin. This suggests that there is minimal dermal exposure of DBNP when exposed topically to skin.

  18. Synthesis and characterization of perfluoro-tert-butyl semifluorinated amphiphilic polymers and their potential application in hydrophobic drug delivery

    PubMed Central

    Decato, Sarah; Bemis, Troy; Madsen, Eric; Mecozzi, Sandro

    2014-01-01

    Semifluorinated polymer surfactants, composed of a monomethyl poly(ethylene glycol) (mPEG) hydrophilic head group and either 1, 2, or 3 perfluoro-tert-butyl (PFtB) groups as the fluorophilic tail, were synthesized, and their aqueous self-assemblies were investigated as a potential design for theranostic nanoparticles. Polymers with three PFtB groups (PFtBTRI) solely formed stable, spherical micelles, approximately 12 nm in size. These PFtBTRI surfactants demonstrate similar characteristics with those of polymers with linear perfluorocarbon tails, despite large differences in tail structure. For example, PFtB polymer solutions stably emulsified 20 v/v% sevoflurane with perfluorooctyl bromide (PFOB) as a stabilizer. However, these PFtB polymers have the additional potential to serve as F-MRI contrast agents. PFtBTRI micelles gave one narrow 19F-NMR signal in D2O, with T1 and T2 parameters of approximately 500 and 100 ms, respectively. 19F-MR images of PFtB polymer solutions at 1 mM gave intense signal at 4.7 T without sensitizers or selective excitation sequences. These preliminary data demonstrate the potential of PFtB polymers as a basic design, which can be further modified to serve as dual drug-delivery and imaging vehicles. PMID:25383100

  19. Anaerobic Methyl tert-Butyl Ether-Degrading Microorganisms Identified in Wastewater Treatment Plant Samples by Stable Isotope Probing

    PubMed Central

    Sun, Weimin; Sun, Xiaoxu

    2012-01-01

    Anaerobic methyl tert-butyl ether (MTBE) degradation potential was investigated in samples from a range of sources. From these 22 experimental variations, only one source (from wastewater treatment plant samples) exhibited MTBE degradation. These microcosms were methanogenic and were subjected to DNA-based stable isotope probing (SIP) targeted to both bacteria and archaea to identify the putative MTBE degraders. For this purpose, DNA was extracted at two time points, subjected to ultracentrifugation, fractioning, and terminal restriction fragment length polymorphism (TRFLP). In addition, bacterial and archaeal 16S rRNA gene clone libraries were constructed. The SIP experiments indicated bacteria in the phyla Firmicutes (family Ruminococcaceae) and Alphaproteobacteria (genus Sphingopyxis) were the dominant MTBE degraders. Previous studies have suggested a role for Firmicutes in anaerobic MTBE degradation; however, the putative MTBE-degrading microorganism in the current study is a novel MTBE-degrading phylotype within this phylum. Two archaeal phylotypes (genera Methanosarcina and Methanocorpusculum) were also enriched in the heavy fractions, and these organisms may be responsible for minor amounts of MTBE degradation or for the uptake of metabolites released from the primary MTBE degraders. Currently, limited information exists on the microorganisms able to degrade MTBE under anaerobic conditions. This work represents the first application of DNA-based SIP to identify anaerobic MTBE-degrading microorganisms in laboratory microcosms and therefore provides a valuable set of data to definitively link identity with anaerobic MTBE degradation. PMID:22327600

  20. Structural studies of 1-butyl-3-methylimidazolium tetrafluoroborate/TX-100/ p-xylene ionic liquid microemulsions.

    PubMed

    Gao, Yan'an; Zhang, Jin; Xu, Hongyan; Zhao, Xueyan; Zheng, Liqiang; Li, Xinwei; Yu, Li

    2006-07-17

    The ionic liquid (IL) 1-butyl-3-methylimidazolium tetrafluoroborate (bmimBF4) forms nonaqueous microemulsions with p-xylene, with the aid of the nonionic surfactant TX-100. The phase behavior of the ternary system is investigated, and three microregions of the microemulsions-ionic liquid-in-oil (IL/O), bicontinuous, and oil-in-ionic liquid (O/IL)-are identified by conductivity measurements, according to percolation theory. On the basis of a phase diagram, a series of IL/O microemulsions are chosen and characterized by dynamic light scattering (DLS). The size of aggregates increases on increasing the amount of added polar component (bmimBF(4)), which is a similar phenomenon to that observed for typical water-in-oil (W/O) microemulsions, suggesting the formation of IL/O microemulsions. The microstructural characteristics of the microemulsions are investigated by FTIR and 1H NMR spectroscopy. The results indicate that the interaction between the electronegative oxygen atoms of the oxyethylene (OE) units in TX-100 and the electropositive imidazolium ring may be the driving force for the solubilization of bmimBF4 into the core of the TX-100 aggregates. In addition, the micropolarity of the microemulsions is investigated by using methyl orange (MO) as a UV/Vis spectroscopic probe. A relatively constant polarity of the microemulsion droplets is obtained in the IL microemulsion. Finally, a plausible structure for the IL/O microemulsion is presented. PMID:16789041

  1. Seasonal and daily variations in concentrations of methyl-tertiary-butyl ether (MTBE) at Cranberry Lake, New Jersey

    USGS Publications Warehouse

    Toran, L.; Lipka, C.; Baehr, A.; Reilly, T.; Baker, R.

    2003-01-01

    Methyl-tertiary-butyl ether (MTBE), an additive used to oxygenate gasoline, has been detected in lakes in northwestern New Jersey. This occurrence has been attributed to the use of gasoline-powered watercraft. This paper documents and explains both seasonal and daily variations in MTBE concentrations at Cranberry Lake. During a recent boating season (late April to September 1999), concentrations of MTBE typically exceeded 20??g/L. MTBE concentrations varied daily from 12 to 24??g/L over a 2-week period that included the Labor Day holiday. Concentrations were highest on weekends when there is more boat traffic, which had an immediate effect on MTBE mass throughout the lake. MTBE concentrations decreased to about 2??g/L shortly after the end of the summer recreational season. The loss of MTBE can be accounted for by volatilization, with a half-life on the order of 10 days. The volatilization rate was modeled with the daily decrease in MTBE then the modeled rate was validated using the data from the seasonal decline. ?? 2003 Elsevier Science Ltd. All rights reserved.

  2. Quantifying Dimer and Trimer Formation by Tri-n-butyl Phosphates in n-Dodecane: Molecular Dynamics Simulations.

    PubMed

    Vo, Quynh N; Dang, Liem X; Nilsson, Mikael; Nguyen, Hung D

    2016-07-21

    Tri-n-butyl phosphate (TBP), a representative of neutral organophosphorous ligands, is an important extractant used in the solvent extraction process for the recovery of uranium and plutonium from spent nuclear fuel. Microscopic pictures of TBP isomerism and its behavior in n-dodecane diluent were investigated utilizing MD simulations with previously optimized force field parameters for TBP and n-dodecane. Potential mean force (PMF) calculations on a single TBP molecule show seven probable TBP isomers. Radial distribution functions (RDFs) of TBP suggest the existence of TBP trimers at high TBP concentrations in addition to dimers. 2D PMF calculations were performed to determine the angle and distance criteria for TBP trimers. The dimerization and trimerization constants of TBP in n-dodecane were obtained and match our own experimental values using the FTIR technique. The new insights into the conformational behaviors of the TBP molecule as a monomer and as part of an aggregate could greatly aid in the understanding of the complexation between TBP and metal ions in a solvent extraction system. PMID:27398866

  3. Determination of the solubility parameter of ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate by inverse gas chromatography.

    PubMed

    Ma, Xiaohong; Wang, Qiang; Li, Xiaoping; Tang, Jun; Zhang, Zhengfang

    2015-11-01

    Thermodynamic properties of ionic liquid 1-butyl-3-methylimidazolium tetrafluoroborate ([BMIM] BF4) were determined via inverse gas chromatography (IGC). Two groups of solvents with different chemical natures and polarities were used to obtain information about [BMIM] BF4-solvent interactions. The specific retention volume, molar heat of sorption, weight fraction activity coefficient, Flory-Huggins interaction parameter as well as solubility parameter were also determined in a temperature range of 333 - 373 K. The results showed that the selected solvents n-C10 to n-C12, carbon tetrachloride, cyclohexane and toluene were poor solvents for [BMIM] BF4, while dichloromethane, acetone, chloroform, methyl acetate, ethanol and methanol were favorite solvents for [BMIM] BF4. In addition, the solubility parameter of [ BMIM] BF4 was determined as 23.39 (J/cm3)0.5 by the extrapolation at 298 K. The experiment proved that IGC was a simple and accurate method to obtain the thermodynamic properties of ionic liquids. This study could be used as a reference to the application and research of the ionic liquids. PMID:26939366

  4. Methyl tert-butyl ether (MTBE) in public and private wells in New Hampshire: occurrence, factors, and possible implications.

    PubMed

    Ayotte, Joseph D; Argue, Denise M; McGarry, Frederick J; Degnan, James R; Hayes, Laura; Flanagan, Sarah M; Helsel, Dennis R

    2008-02-01

    Methyl tert-butyl ether (MTBE) concentrations > or = 0.2 /microg/L were found in samples of untreated water in 18% of public-supply wells (n = 284) and 9.1% of private domestic wells (n = 264) sampled in 2005 and 2006 in New Hampshire. In counties that used reformulated gasoline (RFG), MTBE occurred at or above 0.2 microg/L in 30% of public- and 17% of private-supply wells. Additionally, 52% of public-supply wells collocated with fuel storage and 71% of mobile home park wells had MTBE. MTBE occurrence in public-supply wells was predicted by factors such as proximity to sources of fuel, land use, and population density, as well as low pH and distance from mapped lineaments. RFG use, land-use variables, and pH were important predictors of private-well MTBE occurrence. Variables representing sources of MTBE, such as the distance to known fuel sources, were not significant predictors of MTBE occurrence in private-supply wells. It is hypothesized that private wells may become contaminated from the collective effects of sources in high population areas and from undocumented incidental releases from onsite or proximal gasoline use. From 2003 to 2005, MTBE occurrence decreased in 63 public-supply wells and increased in 60 private-supply wells, but neither trend was statistically significant.

  5. Methyl tert-butyl ether (MTBE) in public and private wells in New Hampshire: Occurrence, factors, and possible implications

    USGS Publications Warehouse

    Ayotte, J.D.; Argue, D.M.; McGarry, F.J.; Degnan, J.R.; Hayes, L.; Flanagan, S.M.; Helsel, D.R.

    2008-01-01

    Methyl tert-butyl ether (MTBE) concentrations ???0.2 ??g/L were found in samples of untreated water in 18% of public-supply wells (n = 284) and 9.1% of private domestic wells (n = 264) sampled in 2005 and 2006 in New Hampshire. In counties that used reformulated gasoline (RFG), MTBE occurred at or above 0.2 ??g/L in 30% of public- and 17% of private-supply wells. Additionally, 52% of public-supply wells collocated with fuel storage and 71% of mobile home park wells had MTBE. MTBE occurrence in public-supply wells was predicted by factors such as proximity to sources of fuel, land use, and population density, as well as low pH and distance from mapped lineaments. RFG use, land-use variables, and pH were important predictors of private-well MTBE occurrence. Variables representing sources of MTBE, such as the distance to known fuel sources, were not significant predictors of MTBE occurrence in private-supply wells. It is hypothesized that private wells may become contaminated from the collective effects of sources in high population areas and from undocumented incidental releases from onsite or proximal gasoline use. From 2003 to 2005, MTBE occurrence decreased in 63 public-supply wells and increased in 60 private-supply wells, but neither trend was statistically significant. ?? 2008 American Chemical Society.

  6. Health Risk Assessment for Inhalation Exposure to Methyl Tertiary Butyl Ether at Petrol Stations in Southern China

    PubMed Central

    Hu, Dalin; Yang, Jianping; Liu, Yungang; Zhang, Wenjuan; Peng, Xiaowu; Wei, Qinzhi; Yuan, Jianhui; Zhu, Zhiliang

    2016-01-01

    Methyl tertiary butyl ether (MTBE), a well known gasoline additive, is used in China nationwide to enhance the octane number of gasoline and reduce harmful exhaust emissions, yet  little is known regarding the potential health risk associated with occupational exposure to MTBE in petrol stations. In this study, 97 petrol station attendants (PSAs) in southern China were recruited for an assessment of the health risk associated with inhalation exposure to MTBE. The personal exposure levels of MTBE were analyzed by Head Space Solid Phase Microextraction GC/MS, and the demographic characteristics of the PSAs were investigated. Cancer and non-cancer risks were calculated with the methods recommended by the United States Environmental Protection Agency. The results showed that the exposure levels of MTBE in operating workers were much higher than among support staff (p < 0.01) and both were lower than 50 ppm (an occupational threshold limit value). The calculated cancer risks (CRs) at the investigated petrol stations was 0.170 to 0.240 per 106 for operating workers, and 0.026 to 0.049 per 106 for support staff, which are below the typical target range for risk management of 1 × 10−6 to 1 × 10−4; The hazard quotients (HQs) for all subjects were <1. In conclusion, our study indicates that the MTBE exposure of PSAs in southern China is in a low range which does not seem to be a significant health risk. PMID:26861375

  7. Enhanced ozonation degradation of di-n-butyl phthalate by zero-valent zinc in aqueous solution: performance and mechanism.

    PubMed

    Wen, Gang; Wang, Sheng-Jun; Ma, Jun; Huang, Ting-Lin; Liu, Zheng-Qian; Zhao, Lei; Su, Jun-Feng

    2014-01-30

    Enhanced ozonation degradation of di-n-butyl phthalate (DBP) by zero-valent zinc (ZVZ) has been investigated using a semi-continuous reactor in aqueous solution. The results indicated that the combination of ozone (O3) and ZVZ showed an obvious synergetic effect, i.e. an improvement of 54.8% on DBP degradation was obtained by the O3/ZVZ process after 10min reaction compared to the cumulative effect of O3 alone and O2/ZVZ. The degradation efficiency of DBP increased gradually with the increase of ZVZ dosage, enhanced as solution pH increasing from 2.0 to 10.0, and more amount of DBP was degraded with the initial concentration of DBP arising from 0.5 to 2.0mgL(-1). Recycling use of ZVZ resulted in the enhancement of DBP degradation, because the newly formed zinc oxide took part in the reaction. The mechanism investigation demonstrated that the enhancement effect was attributed to the introduction of ZVZ, which could promote the utilization of O3, enhance the formation of superoxide radical by reducing O2 via one-electron transfer, accelerate the production of hydrogen peroxide and the generation of hydroxyl radical. Additionally, the newly formed zinc oxide on ZVZ surface also contributed to the enhancement of DBP degradation in the recycling use of ZVZ. Most importantly, the O3/ZVZ process was also effective in enhanced ozonation degradation of DBP under the background of actual waters. PMID:24333716

  8. Simultaneous determination of methyl tert.-butyl ether and its degradation products, other gasoline oxygenates and benzene, toluene, ethylbenzene and xylenes in Catalonian groundwater by purge-and-trap-gas chromatography-mass spectrometry.

    PubMed

    Rosell, Mònica; Lacorte, Sílvia; Ginebreda, Antoni; Barceló, Damià

    2003-05-01

    In Catalonia (northeast Spain), a monitoring program was carried out to determine methyl tert.-butyl ether (MTBE), its main degradation products, tert.-butyl alcohol (TBA), tert.-butyl formate (TBF), and other gasoline additives, the oxygenate dialkyl ethers ethyl tert.-butyl ether, tert.-amyl methyl ether and diisopropyl ether and the aromatic compounds benzene, toluene, ethylbenzene and xylene (BTEX) in 21 groundwater wells that were located near different gasoline point sources (a gasoline spill and underground storage tank leakage). Purge-and-trap coupled to gas chromatography-mass spectrometry was optimised for the simultaneous determination of the above mentioned compounds and enabled to detect concentrations at ng/l or sub-microg/l concentrations. Special attention was given to the determination of polar MTBE degradation products, TBA and TBF, since not much data on method performance and environmental levels are given on these compounds in groundwater. All samples analysed contained MTBE at levels between 0.3 and 70 microg/l. Seven contaminated hot spots were identified with levels up to US Environmental Protection Agency drinking water advisory (20-40 microg/l) and a maximum concentration of 670 microg/l (doubling the Danish suggested toxicity level of 350 microg/l). Samples with high levels of MTBE contained 0.1-60 microg/l of TBA, indicating (but not proving) in situ degradation of parent compound. In all cases, BTEX was at low concentrations or not detected showing less solubility and persistence than MTBE. This fact confirms the suitability of MTBE as a tracer or indicator of long-term gasoline contamination than the historically used BTEX.

  9. Spin dynamics of neutral radical pairs in single crystals of di-tert-butyl-pryrocatechol doped with tetrakis( t-butyl)-phenoxazin

    NASA Astrophysics Data System (ADS)

    Lazarev, G. G.; Kuskov, V. L.; Laukenmann, K.; Angerhofer, A.

    1993-12-01

    The electron spin relaxation in radical pairs formed by photolysis of single crytals of 3,5-di-tert-butylpyrocatechol, doped with 10 -2 M 1-H-2,4,6,8-tetrakis( t-butyl)phenoxazine-1-one was studied by pulsed and stationary EPR in X-band in the temperature range 10-90 K. The relaxation patterns were partly biexponential and were interpreted within the frame of the four-level model of the radical pair, demonstrating the importance of the singlet level in the spin relaxation process. Angular dependencies of the characteristic relaxation times T1 and T2 were measured as well as the temperature dependence of T1. In three cases asymmetric relaxation was found. Excitation spectra of the EPR signals show that different radical pairs (RP) may be distinguished by their action spectra.

  10. Sublethal concentrations of di-n-butyl phthalate promote biochemical changes and DNA damage in juvenile Nile tilapia (Oreochromis niloticus).

    PubMed

    Khalil, Samah R; Abd Elhakim, Yasser; El-Murr, Abd Elhakeem

    2016-02-01

    Increase in consumption of consumer items such as plasticizers have resulted in a sharp rise in the presence of xenobiotics like phthalic acid esters (PEs) in freshwater and marine environments due to contaminated runoff and improper release of effluents. The sublethal toxicity of Di-n-butyl phthalate (DBP) was investigated in juvenile Nile tilapia, Oreochromis niloticus, in an attempt to determine the biological effect of exposure to 1/2 and 1/3 median lethal concentration (96-h LC50) which, in our study was experimentally determined to be 11.8 mg/l. Following four days of exposure, indices of the oxidative potential [Malondialdehyde content (MDA)], antioxidant parameters [superoxide dismutase activity (SOD) and reduced glutathione level (GSH)] and DNA damage were evaluated by single-cell gel electrophoresis (Comet assay). Hepato-renal markers [alanine aminotransferase activity (ALT), creatinine and urea level] and cortisol levels were also quantified in serum. Additionally, histopathological investigations of liver, kidney and gill tissues were conducted. Comparative results between the 1/2 96-h LC50 group and the 1/3 96-h LC50 group clearly showed that there was a significant elevation in MDA levels and a marked increase in DNA damage in addition to inhibition of antioxidant barriers as represented by attenuation of SOD activity and GSH level in the group that was exposed to higher concentration of DBP (1/2 96-h LC50). The hepatorenal markers and cortisol levels were also observed to be elevated. Histopathological examination of the liver, kidney and gills showed pathological alterations that could be correlated with changes in the biochemical profile of the exposed fish. Additionally, anomalous clinical signs were noted. Based on these findings, we conclude from our study that exposure of juvenile O. niloticus to DBP has the potential to induce biochemical as well as tissue morphological alterations associated with oxidative injury and DNA damage. PMID:27348890

  11. Synthesis, structural characterization, electronic spectroscopy, and microfluidic detection of Cu+2 and UO2+2 [di-tert-butyl-salphenazine] complexes†

    PubMed Central

    Maynard, B. A.; Brooks, J. C.; Hardy, E. E.; Easley, C. J.; Gorden, A. E. V.

    2015-01-01

    Metal templation by condensation of 2,3-diaminophenazine with 3,5-di-tert-butyl-2-hydroxybenzaldehyde around the metal centers [M = Cu(ii), and UO2(vi)] affords a new class of M[di-tert-butyl sal-phenazine] metal complexes. Reported here is the synthesis, single crystal X-ray structural characterization, electronic spectroscopy, and microfluidic detection of the formation of these M[di-tert-butyl sal-phenazine] complexes. PMID:25657039

  12. The metabolism of di-(3,5-di-tert.-butyl-4-hydroxybenzyl) ether (Ionox 201) in the rat.

    PubMed

    Wright, A S; Crowne, R S; Hathway, D E

    1967-01-01

    1. Up to one-third of a single oral dose of Ionox 201 was absorbed in rats. 2. In rats dosed with [(14)C]Ionox 201 86.8-97.2% of the label is excreted in the faeces in 24 days (much of this is eliminated in the first 4 days after dosage), 5.6% in the urine and not more than 0.8% in the exhaled air; 5.0% of (14)C is present in the carcass and viscera after removal of the gut, and most of this is in the fatty tissues. 3. About 65.0% of (14)C in the faeces is due to unchanged antioxidant, 30.0% to 3,5-di-tert.-butyl-4-hydroxybenzoic acid, 3.5% to unidentified polar constituent(s), 1.4% to 3,5-di-tert.-butyl-4-hydroxybenzaldehyde and 0.1% to 3,3',5,5'-tetra-tert.-butyl-4-,4'-stilbenequinone. A variable proportion of (14)C in the urine is due to 3,5-di-tert.-butyl-4-hydroxybenzoic acid (40-60%) and the remainder (60-40%) to the ester glucuronide, when the animals were treated with different doses of antioxidant. In eight individual animals dosed with 6.78mg. of [(14)C]Ionox 201, one-third of (14)C in the bile is due to the free acid, 45% to the ester glucuronide, 20% to an unidentified constituent and 2% to unchanged antioxidant, and, in two animals dosed with 13.56mg., there is a small proportion of free acid and a larger proportion of ester glucuronide. About 80% of (14)C in the body fat is due to unchanged antioxidant, 19% to the free acid and 1% to 3,5-di-tert.-butyl-4-hydroxybenzaldehyde. 4. At least 36.2% of a single oral dose of Ionox 201 is metabolized: 3,5-di-tert.-butyl-4-hydroxybenzoic acid accounts for 30.2% of a dose, (3,5-di-tert.-butyl-4-hydroxybenzoyl beta-d-glucopyranosid)uronic acid for 1.4%, 3,5-di-tert.-butyl-4-hydroxybenzaldehyde for 1.3%, 3,3',5,5'-tetra-tert.-butyl-4,4'-stilbenequinone for 0.1% and unidentified polar metabolite(s) for 3.2%. 5. The metabolism of Ionox 201 in vivo is closely related to its antioxidant action in vitro. PMID:6030293

  13. The metabolism of di-(3,5-di-tert.-butyl-4-hydroxybenzyl) ether (Ionox 201) in the rat

    PubMed Central

    Wright, A. S.; Crowne, R. S.; Hathway, D. E.

    1967-01-01

    1. Up to one-third of a single oral dose of Ionox 201 was absorbed in rats. 2. In rats dosed with [14C]Ionox 201 86·8–97·2% of the label is excreted in the faeces in 24 days (much of this is eliminated in the first 4 days after dosage), 5·6% in the urine and not more than 0·8% in the exhaled air; 5·0% of 14C is present in the carcass and viscera after removal of the gut, and most of this is in the fatty tissues. 3. About 65·0% of 14C in the faeces is due to unchanged antioxidant, 30·0% to 3,5-di-tert.-butyl-4-hydroxybenzoic acid, 3·5% to unidentified polar constituent(s), 1·4% to 3,5-di-tert.-butyl-4-hydroxybenzaldehyde and 0·1% to 3,3′,5,5′-tetra-tert.-butyl-4-,4′-stilbenequinone. A variable proportion of 14C in the urine is due to 3,5-di-tert.-butyl-4-hydroxybenzoic acid (40–60%) and the remainder (60–40%) to the ester glucuronide, when the animals were treated with different doses of antioxidant. In eight individual animals dosed with 6·78mg. of [14C]Ionox 201, one-third of 14C in the bile is due to the free acid, 45% to the ester glucuronide, 20% to an unidentified constituent and 2% to unchanged antioxidant, and, in two animals dosed with 13·56mg., there is a small proportion of free acid and a larger proportion of ester glucuronide. About 80% of 14C in the body fat is due to unchanged antioxidant, 19% to the free acid and 1% to 3,5-di-tert.-butyl-4-hydroxybenzaldehyde. 4. At least 36·2% of a single oral dose of Ionox 201 is metabolized: 3,5-di-tert.-butyl-4-hydroxybenzoic acid accounts for 30·2% of a dose, (3,5-di-tert.-butyl-4-hydroxybenzoyl β-d-glucopyranosid)uronic acid for 1·4%, 3,5-di-tert.-butyl-4-hydroxybenzaldehyde for 1·3%, 3,3′,5,5′-tetra-tert.-butyl-4,4′-stilbenequinone for 0·1% and unidentified polar metabolite(s) for 3·2%. 5. The metabolism of Ionox 201 in vivo is closely related to its antioxidant action in vitro. PMID:6030293

  14. Effects of butylated hydroxyanisole on the metabolism and mutagenic and transformation potentials of benzo(a)-pyrene in cultured mammalian cells

    SciTech Connect

    Chen, D.J.; Okinaka, R.T.; Strniste, G.F.

    1982-01-01

    The mechanism by which butylated hydroxyanisole (BHA) inhibits benzo(a)pyrene (BaP)-induced neoplasia in vivo and mutagenicity in vitro has been the subject of a number of investigations. In this study the effect of BHA on BaP metabolism in Syrian hamster embryonic (SHE) cells was studied. In addition, a SHE cell-mediated Chinese hamster ovary (CHO) cell mutagenesis and a SHE cell transformation assay have been used to study the biological effects of BHA. The results indicate that BHA reduces the metabolism of BaP in SHE cells, suppresses BaP-induced mutagenicity in target CHO cells and reduces morphological transformation by BaP in SHE cells. (ACR)

  15. Preparation and electrochemical properties of gel polymer electrolytes using triethylene glycol diacetate-2-propenoic acid butyl ester copolymer for high energy density lithium-ion batteries

    NASA Astrophysics Data System (ADS)

    Fan, Huanhuan; Li, Hongxiao; Fan, Li-Zhen; Shi, Qiao

    2014-03-01

    Gel polymer electrolytes (GPE) composed of triethylene glycol diacetate (TEGDA)-2-propenoic acid butyl ester (BA) copolymer and commercial used liquid organic electrolyte are prepared via in situ polymerization. The ionic conductivity of the as-prepared GPE can reach 5.5 × 10-3 S cm-1 with 6 wt% monomers and 94 wt% liquid electrolyte at 25 °C. Additionally, the temperature dependence of the ionic conductivity is consistent with an Arrhenius temperature behavior in a temperature range of 20-90 °C. Furthermore, the electrochemical stability window of the GPE is 5 V at 25 °C. A Li|GPE|(Li[Li1/6Ni1/4Mn7/12]O2) cell has been fabricated, which shows good charge-discharge properties and stable cycle performance compared to liquid electrolyte under the same test conditions.

  16. Hydrogen oxidation catalysis by a nickel diphosphine complex with pendant tert-butyl amines

    SciTech Connect

    Yang, Jenny Y.; Chen, Shentan; Dougherty, William G.; Kassel, W. Scott; Bullock, R. Morris; DuBois, Daniel L.; Raugei, Simone; Rousseau, Roger; Dupuis, Michel; DuBois, M. Rakowski

    2010-01-01

    A bis-diphosphine nickel complex with tert-butyl functionalized pendant amines [Ni(PCy2Nt-Bu2)2]2+ has been synthesized. It is a highly active electrocatalyst for the oxidation of hydrogen in the presence of base. Finally, the turnover rate of 50 s-1 under 1.0 atm H2 at a potential of -0.77 V vs. the ferrocene couple is 5 times faster than the rate reported heretofore for any other synthetic molecular H2 oxidation catalyst.

  17. Chemoselective Nitration of Phenols with tert-Butyl Nitrite in Solution and on Solid Support

    PubMed Central

    Koley, Dipankar; Colón, Olvia C.; Savinov, Sergey N

    2009-01-01

    tert-Butyl nitrite was identified as a safe and chemoselective nitrating agent that provides preferentially mononitro derivatives of phenolic substrates in the presence of potentially competitive functional groups. On the basis of our control experiments, we propose that the reaction proceeds through the formation of O-nitrosyl intermediates prior to C-nitration via homolysis and oxidation. The reported nitration method is compatible with tyrosine-containing peptides on solid support in the synthesis of fluorogenic substrates for characterization of proteases. PMID:19697919

  18. Repair of Traumatic Abdominal Aortic Pseudoaneurysm Using N-Butyl-2-Cyano-Acrylate Embolization

    SciTech Connect

    Kawai, Nobuyuki; Sato, Morio Tanihata, Hirohiko; Sahara, Shinya; Takasaka, Isao; Minamiguchi, Hiroki; Nakai, Motoki

    2010-04-15

    Embolization using N-butyl-2-cyano-acrylate (NBCA) has been highly regarded for treating pseudoaneurysm, arteriovenous malformation, and hemorrhage of the visceral arteries. We report the case of a patient who fell from a cliff and sustained hemorrhagic shock with blunt abdominal aortic rupture and who underwent embolization using NBCA. This treatment achieved immediate hemostasis and stabilization of vital signs. Although the long-term durability of NBCA is unknown, it appears that certain types of acute aortic hemorrhage with narrow-necked pseudoaneurysm can be controlled by embolization using NBCA.

  19. Holmium Nitrate Complexation with Tri-n-butyl Phosphate in Supercritical Carbon Dioxide

    SciTech Connect

    Robert V. Fox; R. Duane Ball; Peter de B. Harrington; Harry W. Rollins; Chien M. Wai

    2005-12-01

    Holmium nitrate pentahydrate was reacted with tri-n-butyl phosphate in supercritical carbon dioxide at 308 K. The products of the complexation reaction were measured under supercritical fluid conditions using UV-vis spectroscopy. The solubility of the metal complexes in the supercritical fluid phase was measured. The mole-ratio titration method was used to determine the stoichiometry of the soluble complexes. Conditional extraction coefficients were calculated from spectral data using least-squares regression and hard-equilibria models. Data indicate that the holmium nitrate-tributyl phosphate system forms 1:2 and 1:4 holmium-tributyl phosphate complexes.

  20. Determination of n-butylated trialkyllead compounds by gas chromatography with microwave plasma emission detection

    SciTech Connect

    Estes, S.A.; Uden, P.C.; Barnes, R.M.

    1982-12-01

    An analytical gas chromatographic procedure is described for the determination of trialkyllead compounds in aqueous media. The analyte compounds are extracted into benzene from an aqueous solution saturated with sodium chloride. They are then quantitatively converted into n-butyltrialkyllead derivatives by reaction with an n-butyl Grignard reagent. Precolumn Tenax trap enrichment of the derived trialkylbutylleads enables determination to low parts per billion levels to be carried out. Also investigated are extraction efficiencies and injection split ratios onto a fused silica capillary column. Lead specific detection is by atmospheric pressure microwave induced plasma spectrometric emission. Data are presented for a wastewater effluent sample. 3 figures.

  1. Isobaric vapor-liquid equilibria in the system methyl propanoate + n-butyl alcohol

    SciTech Connect

    Susial, P.; Ortega, J. . Lab. de Termodinamica y Fisicoquimica)

    1993-10-01

    Isobaric vapor-liquid equilibria were determined at 74.66, 101.32, and 127.99 kPa for binary mixtures containing methyl propanoate + n-butyl alcohol by using a dynamic still with vapor and liquid circulation. No azeotrope was detected. The data were found to be thermodynamically consistent according to the point to point test. Application of the group-contribution models ASOG, UNIFAC, and modified UNIFAC to the activity coefficients at the three pressures studied gives average errors of less than 10%, 11%, and 3%, respectively.

  2. The role of n-butyl-2-cyanoacrylate in the repair of traumatic diaphragmatic injuries.

    PubMed

    Bas, Gurhan; Ozkan, Orhan Veli; Alimoglu, Orhan; Eryilmaz, Ramazan; Sahin, Mustafa; Okan, Ismail; Cevikbas, Ugur

    2015-01-01

    Diaphragmatic injuries either by blunt or penetrating trauma require prompt surgical intervention and are often exigent to repair. N-butyl-2-cyanoacrylate (n-butyl-2-CA) is a tissue adhesive which has gained wide application in many areas of surgery including emergency. To repair the extensive injuries of the diaphragm it may be necessary the use of synthetic mesh by fixing it with sutures or staples. The use of tissue adhesives may circumvent the potential problems associated with mesh fixation. This study aimed to evaluate the efficacy and safety of tissue adhesives usage for mesh fixation in diaphragmatic injury repair. Twenty-four rats were divided into 3 groups each of them containing 8 rats. A 1- cm diaphragmatic defect was created in all rats. The defect was repaired by polypropylene suture in Group I, by mesh fixed with sutures in group II and by mesh fixed with n-butyl-2-CA in group III. The rats were sacrificed after 1 month. The episode of hernia and the adhesions were assessed by adhesion density score. Also, the abscess and inflammation in the repaired tissue were evaluated microscopically. The Kruskal-Wallis test was performed for the histopathological analysis. No diaphragmatic hernia was detected in any group. While Group III had higher adhesion density scores than group I (P: 0.027), there were no differences between group III and II (P: 0.317) and group II and I (P = 0.095) regarding adhesion density scores. The inflammation grade was higher in group III than group I and II (P < 0.001) and was higher in group II than group I (P < 0.05). There was no differences between each groups, concerning microabcsess formation (P > 0.05). Repair of traumatic diaphragmatic injury in penetrating wound, with polypropylene mesh fixed by n-butyl-2-CA in rats appears to be as efficacious and safe as conventional methods in early period. However, further experimental and clinical study are needed to compare the long-term results of adhesive mesh repair with those of

  3. Percutaneous Direct Puncture Embolization with N-butyl-cyanoacrylate for High-flow Priapism.

    PubMed

    Tokue, Hiroyuki; Shibuya, Kei; Ueno, Hiroyuki; Tokue, Azusa; Tsushima, Yoshito

    2016-09-01

    There are many treatment options in high-flow priapism. Those mentioned most often are watchful waiting, Doppler-guided compression, endovascular highly selective embolization, and surgery. We present a case of high-flow priapism in a 57-year-old man treated by percutaneous direct puncture embolization of a post-traumatic left cavernosal arteriovenous fistula using N-butyl-cyanoacrylate. Erectile function was preserved during a 12-month follow-up. No patients with percutaneous direct puncture embolization for high-flow priapism have been reported previously. Percutaneous direct puncture embolization is a potentially useful and safe method for management of high-flow priapism.

  4. Postcatheterization Femoral Arteriovenous Fistula: Endovascular Treatment with N-Butyl-Cyanoacrylate Embolization

    SciTech Connect

    Onal, Baran Ilgit, Erhan T.; Akpek, Sergin; Coskun, Bilgen

    2006-04-15

    We report a case of an iatrogenic femoral arteriovenous fistula (AVF) in a 67-year-old man presenting with right femoral bruit on the day after sheath removal for cardiac catheterization. This was successfully treated with embolization using N-butyl-cynoacrylate (NBCA) through a coaxial microcatheter. Transcatheter embolization of iatrogenic femoral AVFs with NBCA in selected cases may be a safe and effective treatment in the presence of long fistula tracts. It is then easy to perform in experienced hands and relatively inexpensive.

  5. Intra-operative N-butyl cyanoacrylate embolization arrest of uncontrollable hemorrhage during meningioma resection.

    PubMed

    Gordhan, Ajeet

    2016-01-01

    During the surgical resection of a convexity meningioma in a 63-year-old woman, an uncontrollable active hemorrhage from the operative bed was arrested with microcatheter N-butyl cyanoacrylate (NBCA) embolization after superselective angiography. To date, an uncontrollable neurosurgical intraprocedural hemorrhage terminated by NBCA embolization has not been previously reported. The embolization risk relative to the benefit needs to be carefully considered prior to the surgical removal of a meningioma. This report emphasizes the potential value of embolization with NBCA for arresting active bleeding intraoperatively.

  6. [Biodegradation of di-n-butyl phthalate by mangrove microorganism Rhodococcus ruber 1K].

    PubMed

    Li, Kuixiao; Gu, Jidong

    2005-08-01

    A di-n-butyl phthalate (DBP)degrading bacterium Rhodococcus ruber was isolated from mangrove soil, and its degrading characteristics were studied. The results showed that the bacterium could grow well on the substrate with DBP as the sole source of carbon and energy, and the DBP of 50 mg x L(-1) could be completely degraded after 48 h. Under aerobic condition, the tentative pathway proposed for DBP degradation was through monoester initially, then phthalic acid, and finally CO2 and H2O.

  7. Lipase-catalyzed synthesis of butyl butyrate by alcoholysis in an integrated liquid-vapor system.

    PubMed

    Paiva, Ana L; van Rossum, Diman; Malcata, F Xavier

    2003-01-01

    This paper reports experimental work pertaining to alcoholysis between butanol and ethyl butanoate, catalyzed by an immobilized lipase in a liquid-vapor system where chemical reaction and physical separation are simultaneously carried out. The processing setup was tested for various compositions of the starting feedstock and operated under reduced pressure. Samples were withdrawn both from the boiler and the condenser, and they were chromatographically assayed for butyl butyrate. The integrated configuration tested is quite effective toward improvement of the final yield of the desired product.

  8. Measurement of methyl-tert-butyl-ether (MTBE) in raw drinking water

    SciTech Connect

    Davisson, M L; Koester, C J; Moran, J E

    1999-10-14

    In order to assess the pathways for human exposure to methyl-tert-butyl-ether (MTBE) and to understand the extent of MTBE contamination in watersheds, a purge and trap gas chromatographic mass spectrometric method to measure part-per-trillion (ppt) concentrations of MTBE in environmental waters was developed. A variety of California's raw drinking waters were analyzed. No detectable MTBE was found in deep groundwater (>1000 feet). However shallow groundwater ({approx}250 feet) contained MTBE concentrations of non-detect to 1300 ppt. MTBE concentrations measured in rivers and lakes ranged from non-detect to 3500 ppt. East (San Francisco) Bay area rain water contained approximately 80 ppt MTBE.

  9. Role of solubilized water in the reverse ionic liquid microemulsion of 1-butyl-3-methylimidazolium tetrafluoroborate/TX-100/benzene.

    PubMed

    Gao, Yan'an; Li, Na; Zheng, Liqiang; Bai, Xiangtao; Yu, Li; Zhao, Xueyan; Zhang, Jin; Zhao, Mingwei; Li, Zhen

    2007-03-15

    The ionic liquid (IL) 1-butyl-3-methylimidazolium tetrafluoroborate (bmimBF4) can form nonaqueous microemulsions with benzene by the aid of nonionic surfactant TX-100. The effect of water on ionic liquid-in-oil (IL/O) microemulsions was studied, and it was shown that the addition of small amount of water to the IL microemulsion contributed to the stability of microemulsion and thus increased the amount of solubilized bmimBF4 in the microemulsion. The conductivity measurements also showed that the attractive interactions between IL microdroplets were weakened, that is, the IL/O microemulsion becomes more stable in the present of some water. Fourier transform IR was carried out to analyze the states of the added water, and the result showed that these water molecules mainly behaved as bound water and trapped water, indicating that the water molecules are located in the palisade layers of the IL/O microemulsion. Furthermore, 1H NMR and 19F NMR spectra suggested that the added water molecules built the hydrogen binding network of imidazolium cations and H2O, BF4- anion and H2O, and at the same time the electronegative oxygen atoms of the oxyethylene units of TX-100 and water in the palisade layers, which made the palisade layers more firm and thus increased the stability of the microemulsion. The study can help in further understanding the formation mechanism of microemulsions. In addition, the characteristic solubilization behavior of the added water can provide an aqueous interface film for hydrolysis reactions and therefore may be used as an ideal medium to prepare porous or hollow nanomaterials. PMID:17305388

  10. Amended final report of the safety assessment of t-Butyl Alcohol as used in cosmetics.

    PubMed

    Chen, Melody

    2005-01-01

    t-Butyl Alcohol (t-BuOH) is a tertiary aliphatic alcohol that is used as a solvent or an alcohol denaturant and as a perfume carrier in cosmetics. t-BuOH was reported as an ingredient in 32 formulations of eye makeup, fragrance, and shaving preparations, at concentrations ranging from 0.00001% and 0.3%. There is little acute oral toxicity in animals; e.g., the acute oral LD(50) in rats was 3.0 to 3.7 g/kg. In short-term oral studies in rats, t-BuOH at 2% (w/v) or less in drinking water did not cause gross organ or tissue damage in mice, although weight loss was reported and microscopic damage to livers and kidney and alterations such as centrilobular necrosis, vacuolation in hepatocytes, and loss of hepatic architecture were noted. Subchronic oral dosing with t-BuOH increased the mineralization of the kidney, nephropathy, and urinary bladder transitional cell epithelial hyperplasia in rats; and liver damage, chronic inflammation, hyperplasia of transitional cell epithelium urinary, and proliferative changes including hyperplasia and neoplasia in the thyroid in mice. Male rats exposed to t-BuOH were susceptible to alpha 2mu-globulin nephropathy. t-BuOH (99.9%) was a moderate to severe ocular irritant to rabbits and caused mild to moderate dermal irritation to rabbits. It was not considered to be a primary dermal irritant to rabbits. In animal studies, fetotoxicity generally increased with concentration, and fetal weights were slightly depressed at concentrations of 0.5% to 1% t-BuOH. t-BuOH produced a significant increase in the number of resorptions per litter. There was also a significant decrease in the number of live fetuses per litter. t-BuOH reduced maternal weight gain, litter sizes, birth weights, and weights at weaning, and increased perinatal and postnatal mortality. t-BuOH was not mutagenic in several bacterial and mammalian test systems. The principal effects from 2 years of exposure to t-BuOH in drinking water (up to 10 mg/ml for rats and 20 mg/ml for

  11. Dosimetric measurements of an n-butyl cyanoacrylate embolization material for arteriovenous malformations

    SciTech Connect

    Labby, Zacariah E.; Chaudhary, Neeraj; Gemmete, Joseph J.; Pandey, Aditya S.; Roberts, Donald A.

    2015-04-15

    Purpose: The therapeutic regimen for cranial arteriovenous malformations often involves both stereotactic radiosurgery and endovascular embolization. Embolization agents may contain tantalum or other contrast agents to assist the neurointerventionalists, leading to concerns regarding the dosimetric effects of these agents. This study investigated dosimetric properties of n-butyl cyanoacrylate (n-BCA) plus lipiodol with and without tantalum powder. Methods: The embolization agents were provided cured from the manufacturer with and without added tantalum. Attenuation measurements were made for the samples and compared to the attenuation of a solid water substitute using a 6 MV photon beam. Effective linear attenuation coefficients (ELAC) were derived from attenuation measurements made using a portal imager and derived sample thickness maps projected in an identical geometry. Probable dosimetric errors for calculations in which the embolized regions are overridden with the properties of water were calculated using the ELAC values. Interface effects were investigated using a parallel plate ion chamber placed at set distances below fixed samples. Finally, Hounsfield units (HU) were measured using a stereotactic radiosurgery CT protocol, and more appropriate HU values were derived from the ELAC results and the CT scanner’s HU calibration curve. Results: The ELAC was 0.0516 ± 0.0063 cm{sup −1} and 0.0580 ± 0.0091 cm{sup −1} for n-BCA without and with tantalum, respectively, compared to 0.0487 ± 0.0009 cm{sup −1} for the water substitute. Dose calculations with the embolized region set to be water equivalent in the treatment planning system would result in errors of −0.29% and −0.93% per cm thickness of n-BCA without and with tantalum, respectively. Interface effects compared to water were small in magnitude and limited in distance for both embolization materials. CT values at 120 kVp were 2082 and 2358 HU for n-BCA without and with tantalum, respectively

  12. Acid-Assisted Ball Milling of Cellulose as an Efficient Pretreatment Process for the Production of Butyl Glycosides.

    PubMed

    Boissou, Florent; Sayoud, Nassim; De Oliveira Vigier, Karine; Barakat, Abdellatif; Marinkovic, Sinisa; Estrine, Boris; Jérôme, François

    2015-10-12

    Ball milling of cellulose in the presence of a catalytic amount of H2SO4 was found to be a promising pre-treatment process to produce butyl glycosides in high yields. Conversely to the case of water, n-butanol has only a slight effect on the recrystallization of ball-milled cellulose. As a result, thorough depolymerization of cellulose prior the glycosylation step is no longer required, which is a pivotal aspect with respect to energy consumption. This process was successfully transposed to wheat straw from which butyl glycosides and xylosides were produced in good yields. Butyl glycosides and xylosides are important chemicals as they can be used as hydrotropes but also as intermediates in the production of valuable amphiphilic alkyl glycosides.

  13. Acid-Assisted Ball Milling of Cellulose as an Efficient Pretreatment Process for the Production of Butyl Glycosides.

    PubMed

    Boissou, Florent; Sayoud, Nassim; De Oliveira Vigier, Karine; Barakat, Abdellatif; Marinkovic, Sinisa; Estrine, Boris; Jérôme, François

    2015-10-12

    Ball milling of cellulose in the presence of a catalytic amount of H2SO4 was found to be a promising pre-treatment process to produce butyl glycosides in high yields. Conversely to the case of water, n-butanol has only a slight effect on the recrystallization of ball-milled cellulose. As a result, thorough depolymerization of cellulose prior the glycosylation step is no longer required, which is a pivotal aspect with respect to energy consumption. This process was successfully transposed to wheat straw from which butyl glycosides and xylosides were produced in good yields. Butyl glycosides and xylosides are important chemicals as they can be used as hydrotropes but also as intermediates in the production of valuable amphiphilic alkyl glycosides. PMID:26346950

  14. Molecular recognition of curcumin (Indian Ayurvedic medicine) by the supramolecular probe, p-t-butyl calix(8)arene

    NASA Astrophysics Data System (ADS)

    Meenakshi, C.; Jayabal, P.; Ramakrishnan, V.

    2014-06-01

    The thermodynamic property of the host-guest complexes formed between the curcumin, component of Indian Ayurvedic medicine turmeric, a drug molecule, with the supra molecule, p-t-butyl calix(8)arene was studied. p-t-Butyl calix(8)arene has been used as a host molecule and curcumin as a guest molecule. Optical absorption spectral studies were carried out to investigate the molecular recognition properties of p-t-butyl calix(8)arene with curcumin. The stochiometry of the host-guest complexes formed and the binding constant were determined. An interesting 1:1 and 4:1 stochiometric host-guest complexes were formed. Job's continuous method of variation and Benesi-Hildebrand expression were used for the determination of binding constant and the stochiometry of the host-guest complex formed.

  15. Molecular recognition of curcumin (Indian Ayurvedic medicine) by the supramolecular probe, p-t-butyl calix(8)arene.

    PubMed

    Meenakshi, C; Jayabal, P; Ramakrishnan, V

    2014-06-01

    The thermodynamic property of the host-guest complexes formed between the curcumin, component of Indian Ayurvedic medicine turmeric, a drug molecule, with the supra molecule, p-t-butyl calix(8)arene was studied. p-t-Butyl calix(8)arene has been used as a host molecule and curcumin as a guest molecule. Optical absorption spectral studies were carried out to investigate the molecular recognition properties of p-t-butyl calix(8)arene with curcumin. The stochiometry of the host-guest complexes formed and the binding constant were determined. An interesting 1:1 and 4:1 stochiometric host-guest complexes were formed. Job's continuous method of variation and Benesi-Hildebrand expression were used for the determination of binding constant and the stochiometry of the host-guest complex formed.

  16. "Oxidative addition" of halogens to uranium(IV) bis(amidophenolate) complexes.

    PubMed

    Matson, Ellen M; Opperwall, Stacey R; Fanwick, Phillip E; Bart, Suzanne C

    2013-06-17

    A series of U(IV) complexes, ((R)ap)2U(THF)2 [R = tert-butyl (t-Bu) (1), adamantyl (Ad) (2), diisopropylphenyl (dipp) (3)], supported by the redox-active 4,6-di-tert-butyl-2-(R)amidophenolate ligand, have been synthesized by salt metathesis of 2 equiv of the alkali metal salt of the ligand, M2[(R)ap] [M = K (1 and 2), Na (3)], with UCl4. Exposure of these uranium complexes to 1 equiv of PhICl2 results in oxidative addition to uranium, forming the bis-(4,6-di-tert-butyl-2-(R)iminosemiquinone) ([(R)isq](1-)) uranium(IV) dichloride dimer, [((R)isq)2UCl]2(μ(2)-Cl)2 [R = t-Bu (4), Ad (5), dipp (6)]. The addition of iodine to 1 forms ((tBu)isq)2UI2(THF) (7), while the reactivity of I2 with 2 and 3 results in decomposition. Complexes 1-7 have been characterized by (1)H NMR and electronic absorption spectroscopies. X-ray crystallography was employed to elucidate structural parameters of 2, 3, 5, and 7.

  17. Novel di-tertiary-butyl phenylhydrazones as dual cyclooxygenase-2/5-lipoxygenase inhibitors: synthesis, COX/LOX inhibition, molecular modeling, and insights into their cytotoxicities.

    PubMed

    Ghatak, Shibnath; Vyas, Alok; Misra, Suniti; O'Brien, Paul; Zambre, Ajit; Fresco, Victor M; Markwald, Roger R; Swamy, K Venkateshwara; Afrasiabi, Zahra; Choudhury, Amitava; Khetmalas, Madhukar; Padhye, Subhash

    2014-01-01

    Although dual inhibition of Cyclooxygenase-2 (COX-2) and 5-Lipoxygenase (5-LOX) enzymes is highly effective than targeting COX or LOX alone, there are only a few reports of examining such compounds in case of colorectal cancers (CRC). In the present work we report that the novel di-tert-butyl phenol-based dual inhibitors DTPSAL, DTPBHZ, DTPINH, and DTPNHZ exhibit significant cytotoxicity against human CRC cell lines. Molecular docking studies revealed a good fit of these compounds in the COX-2 and 5-LOX protein cavities. The inhibitors show significant inhibition of COX-2 and 5-LOX activities and are effective against a panel of human colon cancer cell lines including HCA-7, HT-29, SW480 and intestinal Apc10.1 cells as well as the hyaluronan synthase-2 (Has2) enzyme over-expressing colon cancer cells, through inhibition of the Hyaluronan/CD44v6 cell survival pathway. Western blot analysis and qRT-PCR analyses indicated that the di-tert-butyl phenol-based dual inhibitors reduce the expression of COX-2, 5-LOX, and CD44v6 in human colon cancer HCA-7 cells, while the combination of CD44v6shRNA and DTPSAL has an additional inhibitory effect on CD44v6 mRNA expression. The synergistic inhibitory effect of Celecoxib and Licofelone on CD44v6 mRNA expression suggests that the present dual inhibitors down-regulate cyclooxygenase and lipoxygenase enzymes through CD44v6. The compounds also exhibited enhanced antiproliferative potency compared to standard dual COX/LOX inhibitor, viz. Licofelone. Importantly, the HA/CD44v6 antagonist CD44v6shRNA in combination with synthetic compounds had a sensitizing effect on the cancer cells which enhanced their antiproliferative potency, a finding which is crucial for the anti-proliferative potency of the novel synthetic di-tert-butyl phenol based dual COX-LOX inhibitors in colon cancer cells.

  18. Novel di-tertiary-butyl phenylhydrazones as dual cyclooxygenase-2/5-lipoxygenase inhibitors: synthesis, COX/LOX inhibition, molecular modeling, and insights into their cytotoxicities.

    PubMed

    Ghatak, Shibnath; Vyas, Alok; Misra, Suniti; O'Brien, Paul; Zambre, Ajit; Fresco, Victor M; Markwald, Roger R; Swamy, K Venkateshwara; Afrasiabi, Zahra; Choudhury, Amitava; Khetmalas, Madhukar; Padhye, Subhash

    2014-01-01

    Although dual inhibition of Cyclooxygenase-2 (COX-2) and 5-Lipoxygenase (5-LOX) enzymes is highly effective than targeting COX or LOX alone, there are only a few reports of examining such compounds in case of colorectal cancers (CRC). In the present work we report that the novel di-tert-butyl phenol-based dual inhibitors DTPSAL, DTPBHZ, DTPINH, and DTPNHZ exhibit significant cytotoxicity against human CRC cell lines. Molecular docking studies revealed a good fit of these compounds in the COX-2 and 5-LOX protein cavities. The inhibitors show significant inhibition of COX-2 and 5-LOX activities and are effective against a panel of human colon cancer cell lines including HCA-7, HT-29, SW480 and intestinal Apc10.1 cells as well as the hyaluronan synthase-2 (Has2) enzyme over-expressing colon cancer cells, through inhibition of the Hyaluronan/CD44v6 cell survival pathway. Western blot analysis and qRT-PCR analyses indicated that the di-tert-butyl phenol-based dual inhibitors reduce the expression of COX-2, 5-LOX, and CD44v6 in human colon cancer HCA-7 cells, while the combination of CD44v6shRNA and DTPSAL has an additional inhibitory effect on CD44v6 mRNA expression. The synergistic inhibitory effect of Celecoxib and Licofelone on CD44v6 mRNA expression suggests that the present dual inhibitors down-regulate cyclooxygenase and lipoxygenase enzymes through CD44v6. The compounds also exhibited enhanced antiproliferative potency compared to standard dual COX/LOX inhibitor, viz. Licofelone. Importantly, the HA/CD44v6 antagonist CD44v6shRNA in combination with synthetic compounds had a sensitizing effect on the cancer cells which enhanced their antiproliferative potency, a finding which is crucial for the anti-proliferative potency of the novel synthetic di-tert-butyl phenol based dual COX-LOX inhibitors in colon cancer cells. PMID:24295787

  19. Production of fatty acid butyl esters using the low cost naturally immobilized Carica papaya lipase.

    PubMed

    Su, Erzheng; Wei, Dongzhi

    2014-07-01

    In this work, the low cost naturally immobilized Carica papaya lipase (CPL) was investigated for production of fatty acid butyl esters (FABE) to fulfill the aim of reducing the lipase cost in the enzymatic butyl-biodiesel process. The CPL showed specificities to different alcohol acyl acceptors. Alcohols with more than three carbon atoms did not have negative effects on the CPL activity. The CPL catalyzed butanolysis for FABE production was systematically investigated. The reaction solvent, alcohol/oil molar ratio, enzyme amount, reaction temperature, and water activity all affected the butanolysis process. Under the optimized conditions, the highest conversion of 96% could be attained in 24 h. These optimal conditions were further applied to CPL catalyzed butanolysis of other vegetable oils. All of them showed very high conversion. The CPL packed-bed reactor was further developed, and could be operated continuously for more than 150 h. All of these results showed that the low cost Carica papaya lipase can be used as a promising lipase for biodiesel production.

  20. Degradation of n-butyl benzyl phthalate using TiO2/UV.

    PubMed

    Xu, Xiang-Rong; Li, Shen-Xin; Li, Xiao-Yan; Gu, Ji-Dong; Chen, Feng; Li, Xiang-Zhong; Li, Hua-Bin

    2009-05-30

    n-Butyl benzyl phthalate (BBP) has been classified as endocrine disrupting compound and priority pollutant. Effects of TiO(2) dosage, pH, initial BBP concentration and co-existing substances on the degradation of BBP by TiO(2)/UV process were investigated. The optimal TiO(2) dosage and pH value for the BBP degradation were 2.0gL(-1) and 7.0, respectively. The degradation rate of BBP by TiO(2)/UV process could be fitted pseudo-first-order kinetics. The effects of co-existing substances on the degradation rate of BBP revealed that some anions (such as BrO(3)(-), ClO(4)(-) and Cr(2)O(7)(2-)) could enhance BBP degradation, and other anions would restrain BBP degradation. The sequence of inhibition was PO(4)(3-)>CO(3)(2-)>NO(3)(-)>SO(4)(2-)>Cl(-). The cations K(+), Na(+), Mg(2+) and Ca(2+) had the restrained effect on the BBP degradation, and the effect of Ca(2+) was the strongest among four cations tested. The organic compounds acetone and methanol decreased the degradation rate of BBP. The major intermediates of BBP degradation were identified as mono-butyl phthalate, mono-benzyl phthalate and phthalic acid, and a primary degradation mechanism was proposed.

  1. Effect of butyl paraben on the development and microbial composition of periphyton.

    PubMed

    Song, Chaofeng; Lin, Juan; Huang, Xiaolong; Wu, Yonghong; Liu, Jiantong; Wu, Chenxi

    2016-03-01

    Parabens are extensively used as preservatives and bactericides in personal care and other consumer products, and are commonly found in wastewater and surface water as contaminants. However, few data are currently available on the ecotoxicity of parabens. Periphyton biofilm, a widely distributed microbial aggregate of ecological importance in aquatic environment, is frequently used for water quality monitoring, ecological restoration, and toxicity assessment. In this work, the effects of butyl paraben on the development and microbial composition of periphyton biofilm was studied in a laboratory experiment for 32 days using flow through channels. No effect was observed at the environmental relevant concentration level (0.5 μg L(-1)) during the experiment. At the highest tested concentration level (5000 μg L(-1)), following effects were noted: (1) inhibition on algae growth at the end of the experiment as indicated by the chlorophyll a and total biovolume; (2) inhibition of photosynthetic efficiency on day 24 as suggested by the maximal Photosystem II quantum yield (Fv/Fm); (3) decrease of the algal diversity on day 24 and 32 as reflected by the Pielou and Shannon-Weiner indices. Bacteria were less sensitive than algae in the periphyton biofilm, which showed no difference at all tested concentration levels as illustrated by the Biolog EcoPlates™ analysis. Therefore, we conclude that environmental residues of butyl paraben have a very low risk to periphyton in aquatic ecosystems. PMID:26590928

  2. Electrodeposition of germanium from the ionic liquid 1-butyl-1-methylpyrrolidinium dicyanamide.

    PubMed

    Wu, Minxian; Brooks, Neil R; Schaltin, Stijn; Binnemans, Koen; Fransaer, Jan

    2013-04-14

    The electrodeposition of germanium from the ionic liquid 1-butyl-1-methylpyrrolidinium dicyanamide ([BMP][DCA]) and a mixture of [BMP][DCA] and 1-butyl-1-methylpyrrolidinium chloride ([BMP]Cl) was studied using cyclic voltammetry and using an electrochemical quartz crystal microbalance (EQCM). [GeCl4(BuIm)2] (BuIm = N-butylimidazole) was used as germanium source as it has a solubility of 0.47 M, up to 13 times the solubility of GeCl4 in [BMP][DCA]. Cyclic voltammograms show an irreversible electrochemical behavior and two reduction waves were observed. The wave at the more positive potential was assigned to the reduction of Ge(4+) to Ge(2+). The wave at the more negative potential was attributed to the formation of Ge(0). The diffusion coefficient of Ge(4+) in [BMP][DCA] containing 0.1 M [GeCl4(BuIm)2] is 1.1 × 10(-12) m(2) s(-1), and the exchange current density is 2 × 10(-4) A m(-2) at 50 °C. Polymerization of dicyanamide anions took place at the anode in the solution of [BMP][DCA]. The polymerization reaction could be avoided by using an equimolar [BMP]Cl-[BMP][DCA] mixture as electrolyte. Smooth, porous germanium films were electrodeposited on both copper and silicon substrates.

  3. Determination of methacrylic acid in food simulants by pyrolytic butylation-gas chromatography.

    PubMed

    Huang, Zhongping; Qiu, Ruofeng; Liu, Tingfei; Huang, Yilei; Zhu, Zuoyi; Wang, Lili

    2016-07-01

    An on-line pyrolytic butylation approach was proposed to determine methacrylic acid (MA) in food simulants by gas chromatography (GC) without an expensive pyrolyzer. MA in food simulants was converted into butyl methacrylate in the presence of tetrabutylammonium hydroxide (TBAH) without any pretreatment at 330°C in the injection-port, contributing to high GC signal response. The derivatizing conditions for the proposed method were optimized, namely the injection-port temperature, type and amount of the organic alkaline used for derivatization. A series of standard solutions of MA in the range of 1.0-50mg/kg were analyzed with correlation coefficient r≥0.9975. The limits of detection (LODs) were less than 0.15mg/kg for MA in four matrix simulants (distilled water, 3%w/v acetic acid, 10%v/v ethanol, and isooctane). Relative standard deviations (RSDs) for retention time, peak height and peak area were all less than 3.88%. The technique was successfully applied to the analysis of MA migrating from plastic cup samples, with recoveries of added MA in the range of 96.5-123.0%. Direct injection of the simulants into the GC system after migration tests, without any pretreatment step, makes the developed method of great value for rapid screening analysis of samples in bulks. PMID:27262371

  4. Crystal structure of 1,2-bis-[(2-tert-butyl-phen-yl)imino]-ethane.

    PubMed

    Silvino, Alexandre C; Torres, Juliana M

    2015-06-01

    The whole molecule of the title compound, C22H28N2, (I), is generated by inversion symmetry. The mol-ecule is rather similar to that of 2,3-bis-[(2-tert-butyl-phen-yl)imino]-butane, (II), a di-imine ligand comprising similar structural features [Ferreira et al. (2006 ▶). Acta Cryst. E62, o4282-o4284]. Both ligands crystallize with the -N=C(R)-C(R)=N- group around an inversion centre, in a trans configuration. Comparing the two structures, it may be noted that the independent planar groups in both mol-ecules [the central link, -N=C(R)-C(R)=N-, and the terminal aromatic ring] subtend an angle of 69.6 (1)° in (II) and 49.4 (2)° in (I). Ferreira and co-workers proposed that such angle deviation may be ascribed to the presence of two non-classical intra-molecular hydrogen bonds and steric factors. In fact, in (I), similar non-classical hydrogen bonds are observed, and the larger angular deviation in (II) may be assigned to the presence of methyl groups in the di-imino fragment, which can cause steric hindrance due to the presence of bulky tert-butyl substituents in the aromatic rings. The C=N bond lengths are similar in both compounds and agree with comonly accepted values. PMID:26090180

  5. Pressure dependence of butyl nitrate formation in the reaction of butylperoxy radicals with nitrogen oxide.

    PubMed

    Butkovskaya, N I; Kukui, A; Le Bras, G; Rayez, M-T; Rayez, J-C

    2015-05-14

    The yield of 1- and 2-butyl nitrates in the gas-phase reactions of NO with n-C4H9O2 and sec-C4H9O2, obtained from the reaction of F atoms with n-butane in the presence of O2, was determined over the pressure range of 100-600 Torr at 298 K using a high-pressure turbulent flow reactor coupled with a chemical ionization quadrupole mass spectrometer. The yield of butyl nitrates was found to increase linearly with pressure from about 3% at 100 Torr to about 8% at 600 Torr. The results obtained are compared with the available data concerning nitrate formation from NO reaction with other small alkylperoxy radicals. These results are also discussed through the topology of the lowest potential energy surface mainly obtained from DFT(B3LYP/aug-cc-pVDZ) calculations of the RO2 + NO reaction paths. The formation of alkyl nitrates, due essentially to collision processes, is analyzed through a model that points out the pertinent physical parameters of this system. PMID:25380343

  6. The interaction of 1-butyl iodide with the Mo 2C/Mo( 1 0 0 ) surface

    NASA Astrophysics Data System (ADS)

    Bugyi, L.; Oszkó, A.; Solymosi, F.

    2004-07-01

    The adsorption and dissociation of 1-butyl iodide and the reactions of butyl species have been investigated on the Mo 2C/Mo(1 0 0) surface by thermal desorption spectroscopy (TDS), X-ray photoelectron spectroscopy (XPS) and high resolution electron energy loss spectroscopy (HREELS) in the temperature-range of 100-1200 K. 1-Butyl iodide adsorbed molecularly on the clean Mo 2C/Mo(1 0 0) surface at 100 K. A fraction of the C 4H 9I (a) desorbed in two peaks at 166 and 280 K, characteristic of condensed and weakly adsorbed layers, respectively. XPS data indicated that the scission of the C-I bond in C 4H 9I (a) started at as low temperature as 140 K and was completed at 280-300 K. The promotion of rupture of the C-I bond in the adsorbed 1-butyl iodide was achieved by UV irradiation even at 100 K. The dissociation process was not accompanied by any significant changes in the HREEL spectra. Among the reaction products, the thermal desorption of butane was characterized by Tp=246-290 K and that of butene by Tp=246 and 322 K, suggesting the disproportionation reaction of butyl groups. The release of both compounds was a reaction-rate limited process, as confirmed by the separate determination of their bonding to the Mo 2C/Mo(1 0 0) surface. A very limited coupling of butyl species was indicated by the desorption of octane with Tp˜415 K. Heating the adsorbed layer to 470 K the formation of adsorbed butylidyne group was detected, which decomposed to carbon and hydrogen above 600 K.

  7. A cytotoxic principle of Tamarindus indica, di-n-butyl malate and the structure-activity relationship of its analogues.

    PubMed

    Kobayashi, A; Adenan, M I; Kajiyama, S; Kanzaki, H; Kawazu, K

    1996-01-01

    Bioassay-guided fractionation of the methanolic extract of Tamarindus indica fruits led to the isolation of L-(-)-di-n-butyl malate which exhibited a pronounced cytotoxic activity against sea urchin embryo cells. In order to study structure-activity relationships, close-structure relatives of di-n-butyl malate were synthesized using D-(+)- and L-(-)-malic acid as starting materials, and their cytotoxic activities were examined for the sea urchin embryo assay. L-(-)-Di-n-pentyl malate was the most effective inhibitor to the development of the fertilized eggs. Significant inhibitory activity was not seen in the esters of D-(-)-isomer.

  8. Direct synthesis of sulfonated dihydroisoquinolinones from N-allylbenzamide and arylsulfinic acids via TBHP-promoted cascade radical addition and cyclization.

    PubMed

    Xia, Dong; Li, Yang; Miao, Tao; Li, Pinhua; Wang, Lei

    2016-10-01

    A novel synthesis of sulfonated dihydroisoquinolinones via cascade radical addition and cyclization was developed in the presence of tert-butyl hydroperoxide (TBHP). The reactions generated the desired sulfonated dihydroisoquinolinones in good yields from readily available arylsulfinic acids and N-allylbenzamides under metal-free conditions. PMID:27604055

  9. Inhibition of Ca2+ release from Trypanosoma brucei acidocalcisomes by 3,5-dibutyl-4-hydroxytoluene: role of the Na+/H+ exchanger.

    PubMed Central

    Vercesi, A E; Grijalba, M T; Docampo, R

    1997-01-01

    Acidocalcisomes are acidic vacuoles present in trypanosomatids that contain a considerable fraction of intracellular Ca2+. They possess a vacuolar-type H+-ATPase for H+ uptake, a Ca2+/H+ countertransporting ATPase for Ca2+ uptake and a Ca2+/nH+ antiporter for Ca2+ release. Trypanosoma brucei procyclic trypomastigotes acidocalcisomes possess, in addition, an Na+/H+ antiporter that may participate in Ca2+ release from these organelles. In this work we show that the hydrophobic antioxidant 3,5-dibutyl-4-hydroxy toluene (BHT), at concentrations in the range 1-20 microM, inhibits Na+-induced Ca2+ release from the acidocalcisomes of digitonin-permeabilized procyclic trypomastigotes in a concentration-dependent manner. This effect supports the notion that Ca2+ release from this compartment is regulated by the activity of the Na+/H+ antiporter. In the presence of BHT, Ca2+ release could still be obtained by nigericin-mediated alkalinization of the acidocalcisomes, clearly demonstrating that the action of BHT is not at the level of the Ca2+/nH+ antiporter but on that of the Na+/H+ antiporter. In the same range of concentrations and depending on the preincubation time, BHT had an stimulatory or an inhibitory effect on the vacuolar H+-ATPase present in T. brucei acidocalcisomes. Since these effects of BHT were obtained at concentrations which are commonly used for its antioxidant properties, these results indicate that care should be exercised when attributing effects of BHT to only these properties. PMID:9371704

  10. The Epoxidation of 2,5-Di-tert-butyl-1,4-benzoquinone: A Consecutive Reaction for the Physical Chemistry Laboratory.

    ERIC Educational Resources Information Center

    Hairfield, E. M.; And Others

    1985-01-01

    Reports a consecutive first-order reaction for which the concentrations of reactant, intermediate, and products can be determined simulataneously. This reaction is the epoxidation of 2,5-di-tert-butyl-1,4-benzoquinone (I) by alkaline hydroperoxidation using tert-butyl hydroperoxide and benzyltrimethylammonium hydroxide (Triton B) catalyst.…

  11. A PHYSIOLOGICALLY-BASED PHARMACOKINETIC MODEL FOR INTRAVENOUS AND INHALATION-ROUTE PHARMACOKINETICS OF BUTYL ACETATE AND METABOLITES N-BUTANOL AND N-BUTYRIC ACID

    EPA Science Inventory

    Risk assessment for n-butyl acetate and metabolites n-butanol and n-butyric acid (the butyl series) can be accomplished with limited toxicity data and pharmacokinetic data for each compound through application of the "family approach" (Barton et al., 2000). The necessary quantita...

  12. Neutral lipid biosynthesis in engineered Escherichia coli: jojoba oil-like wax esters and fatty acid butyl esters.

    PubMed

    Kalscheuer, Rainer; Stöveken, Tim; Luftmann, Heinrich; Malkus, Ursula; Reichelt, Rudolf; Steinbüchel, Alexander

    2006-02-01

    Wax esters are esters of long-chain fatty acids and long-chain fatty alcohols which are of considerable commercial importance and are produced on a scale of 3 million tons per year. The oil from the jojoba plant (Simmondsia chinensis) is the main biological source of wax esters. Although it has a multitude of potential applications, the use of jojoba oil is restricted, due to its high price. In this study, we describe the establishment of heterologous wax ester biosynthesis in a recombinant Escherichia coli strain by coexpression of a fatty alcohol-producing bifunctional acyl-coenzyme A reductase from the jojoba plant and a bacterial wax ester synthase from Acinetobacter baylyi strain ADP1, catalyzing the esterification of fatty alcohols and coenzyme A thioesters of fatty acids. In the presence of oleate, jojoba oil-like wax esters such as palmityl oleate, palmityl palmitoleate, and oleyl oleate were produced, amounting to up to ca. 1% of the cellular dry weight. In addition to wax esters, fatty acid butyl esters were unexpectedly observed in the presence of oleate. The latter could be attributed to solvent residues of 1-butanol present in the medium component, Bacto tryptone. Neutral lipids produced in recombinant E. coli were accumulated as intracytoplasmic inclusions, demonstrating that the formation and structural integrity of bacterial lipid bodies do not require specific structural proteins. This is the first report on substantial biosynthesis and accumulation of neutral lipids in E. coli, which might open new perspectives for the biotechnological production of cheap jojoba oil equivalents from inexpensive resources employing recombinant microorganisms.

  13. Characterization of the influence of 1-butyl-3-methylimidazolium chloride on the structure and thermal stability of green fluorescent protein

    SciTech Connect

    Heller, William T; O'Neill, Hugh Michael; Zhang, Qiu; Baker, Gary A

    2010-01-01

    Ionic liquids (ILs) are finding a vast array of applications as novel solvents for a wide variety of processes that include enzymatic chemistry, particularly as more biocompatible ILs are designed and discovered. While it is assumed that a native or near-native structure is required for enzymatic activity, there is some evidence that ILs alter protein structure and oligomerization states in a manner than can negatively impact function. The IL 1-butyl-3-methylimidazolium chloride, [bmim]Cl, is a well-studied, water-miscible member of the popular 1-alkyl-3-methylimidazolium IL family. To improve our understanding of the impact of water-miscible ILs on proteins, we have characterized the structure and oligomerization state of green fluorescent protein (GFP) in aqueous solutions containing 25 and 50 vol % [bmim]Cl using a combination of optical spectroscopy and small-angle neutron scattering (SANS). Measurements were also performed as a function of temperature to provide insight into the effect of the IL on the thermal stability of GFP. While GFP exists as a dimer in water, the presence of 25 vol % [bmim]Cl causes GFP to transition to a monomeric state. The SANS data indicate that GFP is a great deal less compact in 50 vol % [bmim]Cl than in neat water, indicative of unfolding from the native structure. The oligomerization state of the protein in IL-containing aqueous solution changes from a dimer to a monomer in response to the IL, but does not change as a function of temperature in the IL-containing solution. The SANS and spectroscopic results also demonstrate that the addition of [bmim]Cl to the solution decreases the thermal stability of GFP, allowing the protein to unfold at lower temperatures than in aqueous solution.

  14. Effects of endocrine disruptor di-n-butyl phthalate on the growth of Bok choy (Brassica rapa subsp. chinensis).

    PubMed

    Liao, Chien-Sen; Yen, Jui-Hung; Wang, Yei-Shung

    2006-12-01

    The effects of the endocrine disrupter, di-n-butyl phthalate (DBP), on the growth of leaf vegetable Bok choy (Brassica rapa subsp. chinensis, white stem Bok choy) were investigated. The results showed that leaves of Bok choy became white in color with the occurrence of chlorosis and necrosis upon treating with 30 mg l(-1) DBP for 42 days. Transmission electron microscopic images revealed that changes in the chloroplast structures accompanied the chlorosis. In addition, a decrease in biomass and chlorophyll, and accumulation of DBP, were found in DBP-treated Bok choy. The growth and morphology of Bok choy showed a significant dose-response relationship upon treatment with DBP in a hydroponic culture medium. The proteome of the leaf tissue was analyzed using two-dimensional gel electrophoresis (2-DE) and mass spectrometry (MS). Six protein spots were identified in 2-DE that showed reproducible differences in expression between the normal control and the DBP-treated sample. Based on proteome level studies two protein spots increased and were identified as superoxide dismutase (SOD) and peroxidase 21 precursor. These proteins are believed to increase in expression in response to free radical exposure as a detoxification mechanism. The other four protein spots that disappeared on treatment with DBP were identified as heat shock cognate protein 80, protein disulfide isomerase precursor, apocytochrome f precursor, and RNA polymerase beta subunit. The first two play an important role in polypeptide folding, the third is associated with electron transport, and the last has a critical function in DNA transcription. This study indicated that DBP affects the proteome formation as well as the physiology and the morphology of Bok choy during growth. The decrease in those four proteins might be related to the growth and development of a plant.

  15. Neutral Lipid Biosynthesis in Engineered Escherichia coli: Jojoba Oil-Like Wax Esters and Fatty Acid Butyl Esters

    PubMed Central

    Kalscheuer, Rainer; Stöveken, Tim; Luftmann, Heinrich; Malkus, Ursula; Reichelt, Rudolf; Steinbüchel, Alexander

    2006-01-01

    Wax esters are esters of long-chain fatty acids and long-chain fatty alcohols which are of considerable commercial importance and are produced on a scale of 3 million tons per year. The oil from the jojoba plant (Simmondsia chinensis) is the main biological source of wax esters. Although it has a multitude of potential applications, the use of jojoba oil is restricted, due to its high price. In this study, we describe the establishment of heterologous wax ester biosynthesis in a recombinant Escherichia coli strain by coexpression of a fatty alcohol-producing bifunctional acyl-coenzyme A reductase from the jojoba plant and a bacterial wax ester synthase from Acinetobacter baylyi strain ADP1, catalyzing the esterification of fatty alcohols and coenzyme A thioesters of fatty acids. In the presence of oleate, jojoba oil-like wax esters such as palmityl oleate, palmityl palmitoleate, and oleyl oleate were produced, amounting to up to ca. 1% of the cellular dry weight. In addition to wax esters, fatty acid butyl esters were unexpectedly observed in the presence of oleate. The latter could be attributed to solvent residues of 1-butanol present in the medium component, Bacto tryptone. Neutral lipids produced in recombinant E. coli were accumulated as intracytoplasmic inclusions, demonstrating that the formation and structural integrity of bacterial lipid bodies do not require specific structural proteins. This is the first report on substantial biosynthesis and accumulation of neutral lipids in E. coli, which might open new perspectives for the biotechnological production of cheap jojoba oil equivalents from inexpensive resources employing recombinant microorganisms. PMID:16461689

  16. Effects of endocrine disruptor di-n-butyl phthalate on the growth of Bok choy (Brassica rapa subsp. chinensis).

    PubMed

    Liao, Chien-Sen; Yen, Jui-Hung; Wang, Yei-Shung

    2006-12-01

    The effects of the endocrine disrupter, di-n-butyl phthalate (DBP), on the growth of leaf vegetable Bok choy (Brassica rapa subsp. chinensis, white stem Bok choy) were investigated. The results showed that leaves of Bok choy became white in color with the occurrence of chlorosis and necrosis upon treating with 30 mg l(-1) DBP for 42 days. Transmission electron microscopic images revealed that changes in the chloroplast structures accompanied the chlorosis. In addition, a decrease in biomass and chlorophyll, and accumulation of DBP, were found in DBP-treated Bok choy. The growth and morphology of Bok choy showed a significant dose-response relationship upon treatment with DBP in a hydroponic culture medium. The proteome of the leaf tissue was analyzed using two-dimensional gel electrophoresis (2-DE) and mass spectrometry (MS). Six protein spots were identified in 2-DE that showed reproducible differences in expression between the normal control and the DBP-treated sample. Based on proteome level studies two protein spots increased and were identified as superoxide dismutase (SOD) and peroxidase 21 precursor. These proteins are believed to increase in expression in response to free radical exposure as a detoxification mechanism. The other four protein spots that disappeared on treatment with DBP were identified as heat shock cognate protein 80, protein disulfide isomerase precursor, apocytochrome f precursor, and RNA polymerase beta subunit. The first two play an important role in polypeptide folding, the third is associated with electron transport, and the last has a critical function in DNA transcription. This study indicated that DBP affects the proteome formation as well as the physiology and the morphology of Bok choy during growth. The decrease in those four proteins might be related to the growth and development of a plant. PMID:16824579

  17. Kinetics of the phthalate metabolites mono-2-ethylhexyl phthalate (MEHP) and mono-n-butyl phthalate (MnBP) in male subjects after a single oral dose.

    PubMed

    Mittermeier, Astrid; Völkel, Wolfgang; Fromme, Hermann

    2016-06-11

    Humans have been exposed to dialkyl ortho-phthalates for decades. Due to degradation the phthalate monoesters, responsible for the toxic effects, are additionally found in environmental media as well as food samples. Nevertheless, the toxicokinetic properties of the monoesters are not known. Therefore, metabolism of the phthalate monoesters mono-2-ethylhexyl phthalate (MEHP) and mono-n-butyl phthalate (MnBP) was studied in four male volunteers (23-58 years of age) after ingestion of a single dose of 50μg/kg bw D4-MEHP or 10μg/kg bw D4-MnBP. The main metabolites in urine were determined up to 46h after administration. In the MEHP-study, more than 90% of each metabolite appeared in the urine within the first 22h, and the average excreted amount of D4-MEHP and its four secondary metabolites was 62% of the administered dose. The highest value of 15% was observed for mono-2-ethyl-5-carboxy-pentyl phthalate (D4-5cx-MEPP). The mean elimination half-life of D4-MEHP was estimated to be 3.5±1.4h. In the MnBP-study, the total recovered values of D4-MnBP and its secondary metabolites ranged from 52% to 130%. The monoester itself, with a half-life of 1.9±0.5h, accounted for the majority of the ingested dose (92%), while the secondary metabolites D4-mono-3-hydroxy-n-butyl phthalate (D4-3OH-MnBP) and D4-3-carboxy-mono-propyl phthalate (D4-3cx-MPP) represented only 7.1% and 1.0% of the ingested dose, respectively. Overall, this study determined that the kinetics of the phthalate monoesters MEHP and MnBP after oral dosage are comparable to the properties of their diesters.

  18. Kinetics of the phthalate metabolites mono-2-ethylhexyl phthalate (MEHP) and mono-n-butyl phthalate (MnBP) in male subjects after a single oral dose.

    PubMed

    Mittermeier, Astrid; Völkel, Wolfgang; Fromme, Hermann

    2016-06-11

    Humans have been exposed to dialkyl ortho-phthalates for decades. Due to degradation the phthalate monoesters, responsible for the toxic effects, are additionally found in environmental media as well as food samples. Nevertheless, the toxicokinetic properties of the monoesters are not known. Therefore, metabolism of the phthalate monoesters mono-2-ethylhexyl phthalate (MEHP) and mono-n-butyl phthalate (MnBP) was studied in four male volunteers (23-58 years of age) after ingestion of a single dose of 50μg/kg bw D4-MEHP or 10μg/kg bw D4-MnBP. The main metabolites in urine were determined up to 46h after administration. In the MEHP-study, more than 90% of each metabolite appeared in the urine within the first 22h, and the average excreted amount of D4-MEHP and its four secondary metabolites was 62% of the administered dose. The highest value of 15% was observed for mono-2-ethyl-5-carboxy-pentyl phthalate (D4-5cx-MEPP). The mean elimination half-life of D4-MEHP was estimated to be 3.5±1.4h. In the MnBP-study, the total recovered values of D4-MnBP and its secondary metabolites ranged from 52% to 130%. The monoester itself, with a half-life of 1.9±0.5h, accounted for the majority of the ingested dose (92%), while the secondary metabolites D4-mono-3-hydroxy-n-butyl phthalate (D4-3OH-MnBP) and D4-3-carboxy-mono-propyl phthalate (D4-3cx-MPP) represented only 7.1% and 1.0% of the ingested dose, respectively. Overall, this study determined that the kinetics of the phthalate monoesters MEHP and MnBP after oral dosage are comparable to the properties of their diesters. PMID:27091076

  19. Groundwater remediation by an in situ biobarrier: a bench scale feasibility test for methyl tert-butyl ether and other gasoline compounds.

    PubMed

    Saponaro, Sabrina; Negri, Marco; Sezenna, Elena; Bonomo, Luca; Sorlini, Claudia

    2009-08-15

    Most gasoline contains high percentages of methyl tert-butyl ether (MTBE) as an additive. The physico-chemical properties of this substance (high water solubility, low sorption in soil) result in high mobility and dissolved concentrations in soil. In situ permeable biological barriers (biobarriers, BBs) can remediate MTBE polluted groundwater by allowing pure cultures or microbial consortia to degrade MTBE when aerobic conditions are present, either by direct metabolism or cometabolism. Lab-scale batch and column tests were carried out to assess a selected microbial consortium in biodegrading MTBE and other gasoline compounds (benzene B, toluene T, ethylbenzene E, xylenes X) and to measure the parameters affecting the efficacy of a BB treatment of polluted groundwater. During the aerobic phase of the batch tests, the simultaneous biodegradation of MTBE, tert-butyl alcohol (TBA), B, T, E and o-X was observed. The rapid biodegradation of BTEXs resulted in decreased oxygen availability, but MTBE degradation was nevertheless measured in the presence of BTEXs. Stationary concentrations of MTBE and TBA were measured when anoxic conditions occurred in the systems. Values for a first order kinetic removal process were obtained for MTBE (0.031+/-0.001 d(-1)), B (0.045+/-0.002 d(-1)) and T (0.080+/-0.004 d(-1)) in the inoculated column tests. The estimate of the BB design parameters suggested that inoculation could significantly modify (double) the longitudinal dispersivity value of the biomass support medium. No effect was observed in the retardation factors for MTBE, B and T. PMID:19200654

  20. Groundwater remediation by an in situ biobarrier: a bench scale feasibility test for methyl tert-butyl ether and other gasoline compounds.

    PubMed

    Saponaro, Sabrina; Negri, Marco; Sezenna, Elena; Bonomo, Luca; Sorlini, Claudia

    2009-08-15

    Most gasoline contains high percentages of methyl tert-butyl ether (MTBE) as an additive. The physico-chemical properties of this substance (high water solubility, low sorption in soil) result in high mobility and dissolved concentrations in soil. In situ permeable biological barriers (biobarriers, BBs) can remediate MTBE polluted groundwater by allowing pure cultures or microbial consortia to degrade MTBE when aerobic conditions are present, either by direct metabolism or cometabolism. Lab-scale batch and column tests were carried out to assess a selected microbial consortium in biodegrading MTBE and other gasoline compounds (benzene B, toluene T, ethylbenzene E, xylenes X) and to measure the parameters affecting the efficacy of a BB treatment of polluted groundwater. During the aerobic phase of the batch tests, the simultaneous biodegradation of MTBE, tert-butyl alcohol (TBA), B, T, E and o-X was observed. The rapid biodegradation of BTEXs resulted in decreased oxygen availability, but MTBE degradation was nevertheless measured in the presence of BTEXs. Stationary concentrations of MTBE and TBA were measured when anoxic conditions occurred in the systems. Values for a first order kinetic removal process were obtained for MTBE (0.031+/-0.001 d(-1)), B (0.045+/-0.002 d(-1)) and T (0.080+/-0.004 d(-1)) in the inoculated column tests. The estimate of the BB design parameters suggested that inoculation could significantly modify (double) the longitudinal dispersivity value of the biomass support medium. No effect was observed in the retardation factors for MTBE, B and T.