4-Vinylphenol

Production

Upon contact with iron oxide at 500 °C, 4-ethylphenol undergoes dehydrogenation to give 4-vinyllphenol: :C2H5C6H4OH → C2H3C6H4OH + H2

Natural occurrence

It is 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. In white wines vinylphenols are dominant (4-vinylphenol 70-1 150 μg/L, 4-vinylguaiacol 10-490 μg/L) whereas, in red wines, it is the corresponding ethyl phenols.

Biosynthesis

The enzyme cinnamate decarboxylase converts p-coumaric acid to 4-vinylphenol. 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.

References

References

1. (2000). "Phenol Derivatives".
2. 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, {{doi. 10.1039/P19960000735
3. 2990913 (German)
4. (1992). "The origin of ethylphenols in wines". Journal of the Science of Food and Agriculture.
5. link. (2008-02-19 at etslabs.com)