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4-Vinylphenol
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4-Vinylphenol : ウィキペディア英語版
4-Vinylphenol

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4-Vinylphenol is a phenolic compound found in wine and beer. It is produced by the spoilage yeast ''Brettanomyces''. When it reaches concentrations greater than the sensory threshold, it can give the wine aromas described as ''barnyard'', ''medicinal'', ''band-aids'', and ''mousy''. In wine, 4-vinylphenol can react with other molecules, such as anthocyanidins, to produce new chemical compounds.〔Structure of new anthocyanin-derived wine pigments. Hélène Fulcrand, Paulo-Jorge Cameira dos Santos, Pascale Sarni-Manchado, Véronique Cheynier and Jean Favre-Bonvin, J. Chem. Soc., Perkin Trans. 1, 1996, pages 735-739, 〕 In white wines vinylphenols are dominant (4-vinylphenol 70-1 150 μg/l, 4-vinylguajacol 10-490 μg/l) whereas, in red wines, it's the corresponding ethyl-phenols. 〔Flüchtige phenolische Verbindungen in Wein = Volatil phenolic compounds of wine. Rapp A. and Versini G., Deutsche Lebensmittel-Rundschau, 1996, vol. 92, no2, pages 42-48, (German)〕
== Biochemistry ==

4-Ethylphenol is produced from the precursor ''p''-coumaric acid. ''Brettanomyces'' converts this to 4-vinylphenol via the enzyme cinnamate decarboxylase.〔(Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol ) at etslabs.com〕 4-Vinylphenol is further reduced to 4-Ethylphenol by the enzyme vinyl phenol reductase. Coumaric acid is sometimes added to microbiological media, enabling the positive identification of ''Brettanomyces'' by smell.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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