4-Ethylphenol

4-Ethylphenol
4-Ethylphenol[1]
Identifiers
CAS number 123-07-9 YesY
ChemSpider 28982 YesY
UNII AGG7E6G0ZC YesY
KEGG C13637 YesY
ChEBI CHEBI:49584 YesY
ChEMBL CHEMBL108475 YesY
Jmol-3D images Image 1
Properties
Molecular formula C8H10O
Molar mass 122.16 g/mol
Appearance White solid
Melting point

42-45 °C

Boiling point

218 °C

Hazards
EU classification Irritant Xi
S-phrases S7/9 S26 S36/37/39 S45
NFPA 704
NFPA 704.svg
1
2
0
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.

Contents

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


Wikimedia Foundation. 2010.

Игры ⚽ Поможем написать реферат

Look at other dictionaries:

  • ethylphenol — noun Any of three isomeric ethyl derivatives of phenol, but especially 4 ethylphenol, which is responsible for a musty smell in some wines …   Wiktionary

  • Ethylphenole — Name 2 Ethylphenol 3 Ethylphenol 4 Ethylphenol Andere Namen 2 Ethylhydroxybenzol 3 Ethylhydroxybenzol 4 Ethylhydroxybenzol Strukturformel …   Deutsch Wikipedia

  • 4-Vinylphenol — IUPAC name 4 ethenylphenol …   Wikipedia

  • 4-Ethylguajacol — Strukturformel Allgemeines Name 4 Ethylguajacol Andere Namen …   Deutsch Wikipedia

  • Coumaric acid — p Coumaric acid …   Wikipedia

  • 4-Ethylguaiacol — IUPAC name 4 Ethyl 2 methoxy phenol …   Wikipedia

  • Phenolic content in wine — The phenolic compounds in Syrah grapes contribute to the taste, color and mouthfeel of the wine. The phenolic compounds natural phenol and polyphenols in wine include a large group of several hundred chemical compounds that affect the taste,… …   Wikipedia

  • Wine — This article is about the beverage. For other uses, see Wine (disambiguation) …   Wikipedia

  • Brettanomyces — Scientific classification Kingdom: Fungi Phylum …   Wikipedia

  • Creosote — For other uses, see Creosote (disambiguation). Creosote is the portion of chemical products obtained by the distillation of a tar that remains heavier than water, notably useful for its anti septic and preservative properties.[1] It is produced… …   Wikipedia

Share the article and excerpts

Direct link
Do a right-click on the link above
and select “Copy Link”