4-Vinylphenol

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4-Vinylphenol
4-Vinylphenol.svg
Names
Preferred IUPAC name
4-Ethenylphenol
Other names
p-Vinylphenol
p-Hydroxystyrene
4-VP
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.018.276 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2 X mark.svgN
    Key: FUGYGGDSWSUORM-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C8H8O/c1-2-7-3-5-8(9)6-4-7/h2-6,9H,1H2
    Key: FUGYGGDSWSUORM-UHFFFAOYAQ
  • C=CC1=CC=C(C=C1)O
Properties
C8H8O
Molar mass 120.15 g/mol
Appearancewhite 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 [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

Production

Upon contact with iron oxide at 500 °C, 4-ethylphenol undergoes dehydrogenation to give 4-vinyllphenol: [1]

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. [2] 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. [3]

Biosynthesis

The conversion of p-coumaric acid to 4-ethylphenol by Brettanomyces via 4-vinylphenol Coumaric acid to 4-ethyphenol.svg
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] [5] 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

Related Research Articles

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<span class="mw-page-title-main">Yeast</span> Informal group of fungi

Yeasts are eukaryotic, single-celled microorganisms classified as members of the fungus kingdom. The first yeast originated hundreds of millions of years ago, and at least 1,500 species are currently recognized. They are estimated to constitute 1% of all described fungal species.

<i>Brettanomyces</i> Genus of fungi

Brettanomyces is a non-spore forming genus of yeast in the family Saccharomycetaceae, and is often colloquially referred to as "Brett". The genus name Dekkera is used interchangeably with Brettanomyces, as it describes the teleomorph or spore forming form of the yeast, but is considered deprecated under the one fungus, one name change. The cellular morphology of the yeast can vary from ovoid to long "sausage" shaped cells. The yeast is acidogenic, and when grown on glucose rich media under aerobic conditions, produces large amounts of acetic acid. Brettanomyces is important to both the brewing and wine industries due to the sensory compounds it produces.

<span class="mw-page-title-main">Ferulic acid</span> Chemical compound

Ferulic acid is a hydroxycinnamic acid, an organic compound with the formula (CH3O)HOC6H3CH=CHCO2H. The name is derived from the genus Ferula, referring to the giant fennel (Ferula communis). Classified as a phenolic phytochemical, ferulic acid is an amber colored solid. Esters of ferulic acid are found in plant cell walls, covalently bonded to hemicellulose such as arabinoxylans.

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<span class="mw-page-title-main">3-Methylbutanoic acid</span> Carboxylic acid with chemical formula (CH3)2CHCH2CO2H CH3CH2

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<i>p</i>-Coumaric acid Chemical compound

p-Coumaric acid is an organic compound with the formula HOC6H4CH=CHCO2H. It is one of the three isomers of hydroxycinnamic acid. It is a white solid that is only slightly soluble in water but very soluble in ethanol and diethyl ether.

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4-Ethylguaiacol Chemical compound

4-Ethylguaiacol, often abbreviated to 4-EG, is a phenolic compound with the molecular formula C9H12O2. It can be produced in wine and beer by Brettanomyces. It is also frequently present in bio-oil produced by pyrolysis of lignocellulosic biomass.

Gentisic acid Chemical compound

Gentisic acid is a dihydroxybenzoic acid. It is a derivative of benzoic acid and a minor (1%) product of the metabolic break down of aspirin, excreted by the kidneys.

2-Methoxy-4-vinylphenol Chemical compound

2-Methoxy-4-vinylphenol is an aromatic substance used as a flavoring agent. It is one of the compounds responsible for the natural aroma of buckwheat.

Phenolic content in wine Wine chemistry

The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, color and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids.

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<span class="mw-page-title-main">Wine chemistry</span> Chemistry of wine

Wine is a complex mixture of chemical compounds in a hydro-alcoholic solution with a pH around 4. The chemistry of wine and its resultant quality depend on achieving a balance between three aspects of the berries used to make the wine: their sugar content, acidity and the presence of secondary compounds. Vines store sugar in grapes through photosynthesis, and acids break down as grapes ripen. Secondary compounds are also stored in the course of the season. Anthocyanins give grapes a red color and protection against ultraviolet light. Tannins add bitterness and astringency which acts to defend vines against pests and grazing animals.

Vinylphenol reductase is an enzyme that catalyses the reaction :

Phloretic acid Chemical compound

Phloretic acid is an organic compound with the formula HOC6H4(CH2)2CO2H. It is a white solid. The compound contains both phenol and carboxylic acid functional groups. It is sometimes called Desaminotyrosine (DAT) because it is identical to the common alpha amino acid tyrosine except for the absence of the amino functional group on the alpha carbon.

4-Hydroxycinnamate decarboxylase is an enzyme that uses p-coumaric acid to produce 4-ethylphenol.

2-Ethylphenol Chemical compound

2-Ethylphenol is an organic compound with the formula C2H5C6H4OH. It is one of three isomeric ethylphenols. A colorless liquid, it occurs as an impurity in xylenols and as such is used in the production of commercial phenolic resins. It is produced by ethylation of phenol using ethylene or ethanol in the presence of aluminium phenolate.

References

  1. Fiege, Helmut; Voges, Heinz-Werner; Hamamoto, Toshikazu; Umemura, Sumio; Iwata, Tadao; Miki, Hisaya; Fujita, Yasuhiro; Buysch, Hans-Josef; Garbe (2000). "Phenol Derivatives". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_313.
  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