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Ethylphenol

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Ethylphenol

4-Ethylphenol[1]
Identifiers
CAS number  YesY
ChemSpider  YesY
UNII  YesY
KEGG  YesY
ChEBI  YesY
ChEMBL  YesY
Jmol-3D images Image 1
Properties
Molecular formula 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
EU classification Irritant Xi
S-phrases S7/9 S26 S36/37/39 S45
NFPA 704
1
2
0
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 YesY   YesY/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.[2] 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

  • 4-Ethylphenol oral toxicity data
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