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{{chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 451705270
| Watchedfields = changed
| Reference=
⚫ | verifiedrevid = 451981233
⚫ | Name = 4-Vinylphenol
| Reference =
⚫ | ImageFile = 4-Vinylphenol.svg
⚫ | Name = 4-Vinylphenol
⚫ | ImageName =
⚫ | ImageFile = 4-Vinylphenol.svg
⚫ | ImageSize = 100px
⚫ | ImageName =
| IUPACName = 4-ethenylphenol
⚫ | ImageSize = 100px
⚫ | OtherNames = p-Vinylphenol<br>p-Hydroxystyrene<br>4-VP
| PIN = 4-Ethenylphenol
⚫ | Section1 = {{Chembox Identifiers
⚫ | OtherNames = ''p''-Vinylphenol<br />''p''-Hydroxystyrene<br />4-VP
| CASNo_Ref =
⚫ |Section1={{Chembox Identifiers
⚫ | CASNo = 2628-17-3
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | PubChem = 62453
⚫ | CASNo = 2628-17-3
⚫ | SMILES = C=CC1=CC=C(C=C1)O
⚫ | PubChem = 62453
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | SMILES = C=CC1=CC=C(C=C1)O
| ChemSpiderID =
⚫ | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = | ChemSpiderID = 56234
| InChI = 1/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2
⚫ | UNII_Ref = {{fdacite|correct|FDA}}
| InChIKey = FUGYGGDSWSUORM-UHFFFAOYAQ
⚫ | UNII = OA7V1SM8YL
| KEGG_Ref = {{keggcite|correct|kegg}} | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2
⚫ | KEGG =
⚫ | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫ | InChI =
| StdInChIKey = FUGYGGDSWSUORM-UHFFFAOYSA-N
| InChIKey =

⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEMBL =
⚫ | ChEBI =
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| UNII_Ref = {{fdacite|correct|FDA}}
| StdInChI =
⚫ | UNII = OA7V1SM8YL
⚫ | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| StdInChIKey =
| RTECS = | KEGG =
⚫ | ChEMBL_Ref = {{ebicite|correct|EBI}}
⚫ }}
⚫ | ChEMBL =
⚫ | Section2 = {{Chembox Properties
| RTECS =
⚫ | Formula = C<sub>8</sub>H<sub>8</sub>O
⚫ }}
⚫ | MolarMass = 120.15 g/mol
⚫ |Section2={{Chembox Properties
| ExactMass = 120.057515 u
⚫ | Formula = C<sub>8</sub>H<sub>8</sub>O
| Appearance =
⚫ | MolarMass = 120.15 g/mol
| Solvent =
| Appearance = white sublimable solid
| MeltingPt =
| BoilingPt = | Solvent =
| MeltingPtC = 73.5
⚫ }}
| BoilingPt =
⚫ | Section7 = {{Chembox Hazards
⚫ }}
| EUClass =
⚫ |Section7={{Chembox Hazards
| NFPA-H =
| NFPA-F = | NFPA-H =
| NFPA-R = | NFPA-F =
| SPhrases = | NFPA-R =
⚫ }}
| SPhrases =
⚫ }}
}} }}
'''4-Vinylphenol''' is an ] with the formula C<sub>2</sub>H<sub>3</sub>C<sub>6</sub>H<sub>4</sub>OH. It is the most studied of the three isomeric ]s. It is a white volatile solid.
⚫ '''4-Vinylphenol''' is a ] compound found in ] and ]. It is produced by the spoilage ] '']''. When it reaches concentrations greater than the ], it can give the wine ]s described as ''barnyard'', ''medicinal'', '']s'', and ''mousy''. In wine, 4-vinylphenol can react with other molecules, such as ]s, to produce new chemical compounds.<ref>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}}</ref> In white wines vinylphenols are dominant (4-vinylphenol 70-1 150 μg/l, ] 10-490 μg/l) whereas, in red wines, it's the corresponding ]s. <ref>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)</ref>


==Biochemistry== ==Production==
Upon contact with iron oxide at 500 °C, ] undergoes ] to give 4-vinyllphenol:<ref>{{Ullmann |doi=10.1002/14356007.a19_313|title=Phenol Derivatives|year=2000|last1=Fiege|first1=Helmut|last2=Voges|first2=Heinz-Werner|last3=Hamamoto|first3=Toshikazu|last4=Umemura|first4=Sumio|last5=Iwata|first5=Tadao|last6=Miki|first6=Hisaya|last7=Fujita|first7=Yasuhiro|last8=Buysch|first8=Hans-Josef|last9=Garbe|first9=Dorothea|last10=Paulus|first10=Wilfried|isbn=3527306730}}</ref>
⚫ ] to ] by ''Brettanomyces'' via 4-vinylphenol]]
:C<sub>2</sub>H<sub>5</sub>C<sub>6</sub>H<sub>4</sub>OH → C<sub>2</sub>H<sub>3</sub>C<sub>6</sub>H<sub>4</sub>OH + H<sub>2</sub>
⚫ ] is produced from the precursor ]. ''Brettanomyces'' converts this to 4-vinylphenol via the enzyme ].<ref> at etslabs.com</ref> 4-Vinylphenol is further reduced to 4-Ethylphenol by the enzyme ]. Coumaric acid is sometimes added to ], enabling the positive identification of ''Brettanomyces'' by smell.


==See also== ==Natural occurrence==
⚫ It is found in ] and ]. It is produced by the spoilage ] '']''. When it reaches concentrations greater than the ], it can give the wine ]s described as ''barnyard'', ''medicinal'', ''band-aids'', and ''mousy''. In wine, 4-vinylphenol can react with other molecules, such as ]s, to produce new chemical compounds.<ref>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}}</ref> In white wines vinylphenols are dominant (4-vinylphenol 70-1 150 μg/L, ] 10-490 μg/L) whereas, in red wines, it is the corresponding ]s.<ref>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)</ref>

=== Biosynthesis===
⚫ ] to ] by ''Brettanomyces'' via 4-vinylphenol]]{{clear-left}}
⚫ The enzyme ] converts ] to 4-vinylphenol.<ref>{{cite journal|doi=10.1002/jsfa.2740600205|title=The origin of ethylphenols in wines|year=1992|last1=Chatonnet|first1=Pascal|last2=Dubourdie|first2=Denis|last3=Boidron|first3=Jean-Noël|last4=Pons|first4=Monique|journal=Journal of the Science of Food and Agriculture|volume=60|issue=2|pages=165–178}}</ref><ref> {{webarchive|url=https://web.archive.org/web/20080219204946/http://www.etslabs.com/scripts/ets/pagetemplate/blank.asp?pageid=193 |date=2008-02-19 }} at etslabs.com</ref> 4-Vinylphenol is further reduced to 4-ethylphenol by the enzyme ]. Coumaric acid is sometimes added to ], enabling the positive identification of ''Brettanomyces'' by smell.

== See also ==
* ] * ]
* ]
* ] * ]
* ] * ]
* ] (polyvinylphenol or PVP) is a plastic structurally similar to polystyrene. * ] (polyvinylphenol or PVP) is a plastic structurally similar to polystyrene.


==References== == References ==
<references/> <references/>

==External links==
*


{{DEFAULTSORT:Vinylphenol, 4-}} {{DEFAULTSORT:Vinylphenol, 4-}}
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