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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-}}
] ]
] ]
]

Latest revision as of 10:13, 21 October 2024

4-Vinylphenol
Names
Preferred IUPAC name 4-Ethenylphenol
Other names p-Vinylphenol
p-Hydroxystyrene
4-VP
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.276 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2Key: FUGYGGDSWSUORM-UHFFFAOYSA-N
  • InChI=1/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2Key: FUGYGGDSWSUORM-UHFFFAOYAQ
SMILES
  • C=CC1=CC=C(C=C1)O
Properties
Chemical formula C8H8O
Molar mass 120.15 g/mol
Appearance white sublimable solid
Melting point 73.5 °C (164.3 °F; 346.6 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

4-Vinylphenol is an organic compound with the formula C2H3C6H4OH. It is the most studied of the three isomeric vinylphenols. It is a white volatile solid.

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

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.

See also

References

  1. Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe, Dorothea; Paulus, Wilfried (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313. ISBN 3527306730.
  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. 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)
  4. Chatonnet, Pascal; Dubourdie, Denis; Boidron, Jean-Noël; Pons, Monique (1992). "The origin of ethylphenols in wines". Journal of the Science of Food and Agriculture. 60 (2): 165–178. doi:10.1002/jsfa.2740600205.
  5. Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol Archived 2008-02-19 at the Wayback Machine at etslabs.com
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