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Chemical Compound Review

Vinylacetat     ethenyl ethanoate

Synonyms: Vinylazetat, Vinylacetaat, VyAc, VyAr, Acetoxyethene, ...
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Disease relevance of vinyl acetate


Psychiatry related information on vinyl acetate


High impact information on vinyl acetate


Chemical compound and disease context of vinyl acetate

  • METHODS: Paclitaxel-loaded ethylene vinyl acetate wraps were placed around the graft-vein anastomosis on one side, with control polymers being placed on the contralateral side in our pig model of arteriovenous graft stenosis [9].
  • The thermal inactivation of mesophilic Bacillus subtilis alpha-amylase modified by maleic anhydride/vinyl acetate copolymer has been studied at different polymer/enzyme ratios in the pH range of relevance to enzymatic catalysis [10].

Biological context of vinyl acetate

  • DPXL accumulation followed S-phase enzymatic kinetics, with a rate of formation of 1.1 DPXLs/plasmid molecule/mmol vinyl acetate/microgram microsomal protein/microgram DNA [8].
  • This is consistent with investigations on metabolism and pharmacokinetics of vinyl acetate which show that this compound, after entering the organism, is immediately split by blood esterases and thus may not be available for epoxidation to an ultimately carcinogenic metabolite [11].
  • PdCl(2) can catalyze the acetylation of primary and secondary alcohols with vinyl acetate [12].
  • Three microbial lipases have been used to deracemize trans-2-fluorocycloalkanols 2 both by hydrolysis of the corresponding acetates 3 or chloroacetates 4 and by esterification of the fluorohydrins 2 using vinyl acetate and vinyl chloroacetate, respectively [13].
  • [reaction: see text] Stereospecific 1,2-cis glycosylation of 2-O-vinyl thioglycosides, synthesized from the corresponding alcohols by Ir-catalyzed transvinylation with vinyl acetate, is achieved by iodine-mediated tethering of a range of primary and secondary carbohydrate acceptors, followed by intramolecular aglycon delivery (IAD) [14].

Anatomical context of vinyl acetate


Associations of vinyl acetate with other chemical compounds


Gene context of vinyl acetate


Analytical, diagnostic and therapeutic context of vinyl acetate


  1. Challenging dogma: thresholds for genotoxic carcinogens? The case of vinyl acetate. Hengstler, J.G., Bogdanffy, M.S., Bolt, H.M., Oesch, F. Annu. Rev. Pharmacol. Toxicol. (2003) [Pubmed]
  2. Immunosuppression studies in foreign body tumorigenesis: no evidence for tumor-specific antigenicity. Michelich, V.J., Buoen, L.C., Brand, K.G. J. Natl. Cancer Inst. (1977) [Pubmed]
  3. Increased Enantioselectivity and Remarkable Acceleration of Lipase-Catalyzed Transesterification by Using an Imidazolium PEG-Alkyl Sulfate Ionic Liquid. Itoh, T., Matsushita, Y., Abe, Y., Han, S.H., Wada, S., Hayase, S., Kawatsura, M., Takai, S., Morimoto, M., Hirose, Y. Chemistry (Weinheim an der Bergstrasse, Germany) (2006) [Pubmed]
  4. A biologically based risk assessment for vinyl acetate-induced cancer and noncancer inhalation toxicity. Bogdanffy, M.S., Sarangapani, R., Plowchalk, D.R., Jarabek, A., Andersen, M.E. Toxicol. Sci. (1999) [Pubmed]
  5. Vinyl acetate casts of emphysematous rat lungs. Colombo, C., Colombo, S., Steinetz, B. Journal of pharmaceutical sciences. (1976) [Pubmed]
  6. N-heterocyclic carbenes as versatile nucleophilic catalysts for transesterification/acylation reactions. Grasa, G.A., Kissling, R.M., Nolan, S.P. Org. Lett. (2002) [Pubmed]
  7. Chromosome damage induced by vinyl acetate through in vitro formation of acetaldehyde in human lymphocytes and Chinese hamster ovary cells. Norppa, H., Tursi, F., Pfäffli, P., Mäki-Paakkanen, J., Järventaus, H. Cancer Res. (1985) [Pubmed]
  8. Reaction kinetics of DNA-histone crosslinking by vinyl acetate and acetaldehyde. Kuykendall, J.R., Bogdanffy, M.S. Carcinogenesis (1992) [Pubmed]
  9. Perivascular paclitaxel wraps block arteriovenous graft stenosis in a pig model. Kelly, B., Melhem, M., Zhang, J., Kasting, G., Li, J., Krishnamoorthy, M., Heffelfinger, S., Rudich, S., Desai, P., Roy-Chaudhury, P. Nephrol. Dial. Transplant. (2006) [Pubmed]
  10. Study on the thermal stability of alpha-amylase modified by maleic anhydride copolymer. Brissová, M., Augustín, J., Simonetti, M. Int. J. Biol. Macromol. (1994) [Pubmed]
  11. Vinyl acetate, a structural analog of vinyl carbamate, fails to induce enzyme-altered foci in rat liver. Laib, R.J., Bolt, H.M. Carcinogenesis (1986) [Pubmed]
  12. Palladium(II) chloride catalyzed selective acetylation of alcohols with vinyl acetate. Bosco, J.W., Saikia, A.K. Chem. Commun. (Camb.) (2004) [Pubmed]
  13. Synthesis of optically active vicinal fluorohydrins by lipase-catalyzed deracemization. Wölker, D., Haufe, G. J. Org. Chem. (2002) [Pubmed]
  14. Stereospecific synthesis of 1,2-cis glycosides by vinyl-mediated IAD. Chayajarus, K., Chambers, D.J., Chughtai, M.J., Fairbanks, A.J. Org. Lett. (2004) [Pubmed]
  15. Adherence of bacteria, yeast, blood cells, and latex spheres to large-porosity membrane filters. Zierdt, C.H. Appl. Environ. Microbiol. (1979) [Pubmed]
  16. Enzymatic desymmetrization of a meso polyol corresponding to the C(19)-C(27) segment of rifamycin S. Chênevert, R., Rose, Y.S. J. Org. Chem. (2000) [Pubmed]
  17. Vinyl acetate decreases intracellular pH in rat nasal epithelial cells. Lantz, R.C., Orozco, J., Bogdanffy, M.S. Toxicol. Sci. (2003) [Pubmed]
  18. Regioselective enzyme-catalyzed synthesis of sophorolipid esters, amides, and multifunctional monomers. Singh, S.K., Felse, A.P., Nunez, A., Foglia, T.A., Gross, R.A. J. Org. Chem. (2003) [Pubmed]
  19. Denatured collagen as support for a FGF-2 delivery system: physicochemical characterizations and in vitro release kinetics and bioactivity. Côté, M.F., Laroche, G., Gagnon, E., Chevallier, P., Doillon, C.J. Biomaterials (2004) [Pubmed]
  20. Cytotoxicity and DNA-protein crosslink formation in rat nasal tissues exposed to vinyl acetate are carboxylesterase-mediated. Kuykendall, J.R., Taylor, M.L., Bogdanffy, M.S. Toxicol. Appl. Pharmacol. (1993) [Pubmed]
  21. Impact of antinucleants on transdermal delivery of testosterone from a spray. Leichtnam, M.L., Rolland, H., W??thrich, P., Guy, R.H. Journal of pharmaceutical sciences (2007) [Pubmed]
  22. Kinetics of nasal carboxylesterase-mediated metabolism of vinyl acetate. Bogdanffy, M.S., Taylor, M.L. Drug Metab. Dispos. (1993) [Pubmed]
  23. Influence of spinline stress on release properties of a coaxial controlled release device based on EVA polymers. van Laarhoven, H., Veurink, J., Kruft, M.A., Vromans, H. Pharm. Res. (2004) [Pubmed]
  24. Validation of human physiologically based pharmacokinetic model for vinyl acetate against human nasal dosimetry data. Hinderliter, P.M., Thrall, K.D., Corley, R.A., Bloemen, L.J., Bogdanffy, M.S. Toxicol. Sci. (2005) [Pubmed]
  25. Polyvinyl alcohol plasma deposited nylon 4 membrane for hemodialysis. Shih, C.Y., Lai, J.Y. J. Biomed. Mater. Res. (1993) [Pubmed]
  26. Chronic toxicity studies of vinyl acetate in Fischer rats. Lijinsky, W., Reuber, M.D. Toxicol. Appl. Pharmacol. (1983) [Pubmed]
  27. Induction of micronuclei by vinyl acetate in mouse bone marrow cells and cultured human lymphocytes. Mäki-Paakkanen, J., Norppa, H. Mutat. Res. (1987) [Pubmed]
  28. Determination of vinyl acetate in air by gas chromatography. Sidhu, K.S. Journal of applied toxicology : JAT. (1981) [Pubmed]
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