4-Vinylphenol

4-Vinylphenol

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Names
IUPAC name 4-ethenylphenol
Other names p-Vinylphenol p-Hydroxystyrene 4-VP
Identifiers
CAS Number	2628-17-3 Y
ChemSpider	56234
Jmol 3D model	Interactive image
PubChem	62453
UNII	OA7V1SM8YL Y
InChI InChI=1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2 Key: FUGYGGDSWSUORM-UHFFFAOYSA-N InChI=1/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2 Key: FUGYGGDSWSUORM-UHFFFAOYAQ
SMILES C=CC1=CC=C(C=C1)O
Properties
Chemical formula	C8H8O
Molar mass	120.15 g/mol
Vapor pressure	{{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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. 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.

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

External links

• 4-Ethylphenol oral toxicity data