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4-Ethylphenol

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4-Ethylphenol[1]
Names
Preferred IUPAC name
4-Ethylphenol
Other names
p-Ethylphenol (no longer recommended[2])
1-Ethyl-4-hydroxybenzene
1-Hydroxy-4-ethylbenzene
4-hydroxyphenylethane
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.181 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3 checkY
    Key: HXDOZKJGKXYMEW-UHFFFAOYSA-N checkY
  • InChI=1/C8H10O/c1-2-7-3-5-8(9)6-4-7/h3-6,9H,2H2,1H3
    Key: HXDOZKJGKXYMEW-UHFFFAOYAF
  • Oc1ccc(cc1)CC
Properties
C8H10O
Molar mass 122.16 g/mol
Appearance White solid
Melting point 42 to 45 °C (108 to 113 °F; 315 to 318 K)
Boiling point 218 °C (424 °F; 491 K)
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 [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

4-Ethylphenol, often abbreviated to 4-EP, is a phenolic compound.

Natural occurrences

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.

It is also a component of castoreum, the exudate from the castor sacs of the mature North American beaver (Castor canadensis) and the European beaver (Castor fiber), used in perfumery.

Biochemistry

4-Ethylphenol is produced from the precursor p-coumaric acid. Brettanomyces converts this to 4-vinylphenol via the enzyme cinnamate decarboxylase.[3] 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. ^ Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 690. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4. Only one name is retained, phenol, for C6H5-OH, both as a preferred name and for general nomenclature. The structure is substitutable at any position. Locants 2, 3, and 4 are recommended, not o, m, and p.
  3. ^ 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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