4-Vinylphenol

4-Vinylphenol
IUPAC name 4-ethenylphenol
Other names p-Vinylphenol p-Hydroxystyrene 4-VP
Identifiers
CAS number	2628-17-3
PubChem	62453
UNII	OA7V1SM8YL Y
Jmol-3D images	Image 1
SMILES C=CC1=CC=C(C=C1)O
Properties
Molecular formula	C8H8O
Molar mass	120.15 g/mol
Exact mass	120.057515 u
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.^[1] 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. ^[2]

Biochemistry

The conversion of p-coumaric acid to 4-ethylphenol by Brettanomyces via 4-vinylphenol

4-Ethylphenol is produced from the precursor p-coumaric acid. Brettanomyces converts this to 4-vinylphenol via the enzyme cinnamate decarboxylase.^[3] 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.

See also

• 4-Ethylguaiacol
• Wine fault
• Wine chemistry
• Poly-4-vinylphenol (polyvinylphenol or PVP) is a plastic structurally similar to polystyrene.

References

1. ^ 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
2. ^ 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, INIST:2990913 (German)
3. ^ Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol at etslabs.com

External links

• 4-Ethylphenol oral toxicity data