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4-Ethylphenol

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4-Ethylphenol
Names
Other names p-Ethylphenol
1-Ethyl-4-hydroxybenzene
1-Hydroxy-4-ethylbenzene
4-hydroxyphenylethane
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.181 Edit this at Wikidata
KEGG
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3Key: HXDOZKJGKXYMEW-UHFFFAOYSA-N
  • InChI=1/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3Key: HXDOZKJGKXYMEW-UHFFFAOYAF
SMILES
  • Oc1ccc(cc1)CC
Properties
Chemical formula C8H10O
Molar mass 122.16 g/mol
Appearance White solid
Melting point 42–45 °C
Boiling point 218 °C
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2 1 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

4-Ethylphenol, often abbreviated to 4-EP, is a phenolic compound with the molecular formula C8H10O. In wine and beer it is produced by the spoilage yeast Brettanomyces. When it reaches concentrations greater than the sensory threshold (140 µg/L) it can give the wine aromas described as barnyard, medicinal, band-aids, and mousy. In certain Belgian beer styles, a high 4-EP level may be desirable; however, very high levels of the compound in wine can render it undrinkable. The level of 4-ethylphenol is roughly proportional to Brettanomyces concentration and activity, and can therefore be used as an indicator of the yeast's presence. There are significant differences between strains of Brettanomyces in their ability to produce 4-ethylphenol.

Biochemistry

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.

The conversion of p-coumaric acid to 4-ethyphenol by Brettanomyces

See also

References

  1. 4-Ethylphenol MSDS
  2. Brettanomyces Monitoring by Analysis of 4-ethylphenol and 4-ethylguaiacol at etslabs.com

External links

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