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

Natural phenol

Natural phenols, bioavailable phenols, plant phenolics, low molecular weight phenols or phenoloids are a class of natural products. They are small molecules containing one or more phenolic group. These molecules are smaller in size than polyphenols, containing less than 12 phenolic groups...

 compound with the molecular formula C₈H₁₀O. In wine

Wine

Wine is an alcoholic beverage, made of fermented fruit juice, usually from grapes. The natural chemical balance of grapes lets them ferment without the addition of sugars, acids, enzymes, or other nutrients. Grape wine is produced by fermenting crushed grapes using various types of yeast. Yeast...

 and beer

Beer

Beer is the world's most widely consumed andprobably oldest alcoholic beverage; it is the third most popular drink overall, after water and tea. It is produced by the brewing and fermentation of sugars, mainly derived from malted cereal grains, most commonly malted barley and malted wheat...

 it is produced by the spoilage yeast

Yeast

Yeasts are eukaryotic micro-organisms classified in the kingdom Fungi, with 1,500 species currently described estimated to be only 1% of all fungal species. Most reproduce asexually by mitosis, and many do so by an asymmetric division process called budding...

 Brettanomyces

Brettanomyces

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. The cellular morphology of...

. When it reaches concentrations greater than the sensory threshold

Sensory threshold

Sensory threshold is a theoretical concept used in psychophysics. A stimulus that is less intense than the sensory threshold will not elicit any sensation...

 (140 µg/L) it can give the wine aromas described as barnyard, medicinal, band-aid

Band-Aid

Band-Aid is a brand name for Johnson & Johnson's line of adhesive bandages and related products. It has also become a genericized trademark for any adhesive bandage in Australia, Brazil, Canada, India and the United States....

s, 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

Coumaric acid

Coumaric acid is a hydroxycinnamic acid, an organic compound that is a hydroxy derivative of cinnamic acid. There are three isomers, o-coumaric acid, m-coumaric acid, and p-coumaric acid, that differ by the position of the hydroxy substitution of the phenyl group...

. Brettanomyces converts this to 4-vinylphenol

4-Vinylphenol

4-Vinylphenol is a phenolic compound 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...

 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

Growth medium

A growth medium or culture medium is a liquid or gel designed to support the growth of microorganisms or cells, or small plants like the moss Physcomitrella patens.There are different types of media for growing different types of cells....

, enabling the positive identification of Brettanomyces by smell.

External links

• 4-Ethylphenol oral toxicity data