4-Ethylphenol

A phenolic compound found in wine and other fermented products

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4-Ethylphenol is a phenolic compound with the chemical formula C₈H₁₀O. It is a derivative of phenol and is characterized by an ethyl group attached to the para position of the phenol ring.

Occurrence

4-Ethylphenol is commonly found in wine, where it is produced by the action of certain yeast and bacteria during the fermentation process. It is also present in other fermented products such as beer and cider.

Production

4-Ethylphenol can be synthesized from coumaric acid through a decarboxylation reaction. This process is often facilitated by microbial activity, particularly by species of the genus Brettanomyces.

Conversion of coumaric acid to 4-ethylphenol

Properties

4-Ethylphenol is a colorless liquid with a characteristic phenolic odor. It is slightly soluble in water but more soluble in organic solvents. The presence of 4-ethylphenol in wine is often associated with off-flavors described as "barnyard" or "medicinal".

Applications

While 4-ethylphenol is generally considered an undesirable compound in wine, it has applications in the synthesis of other chemical compounds. It can be used as an intermediate in the production of pharmaceuticals and fragrances.

Health Effects

Exposure to 4-ethylphenol can occur through the consumption of contaminated beverages. In small amounts, it is not considered harmful, but excessive exposure may lead to adverse health effects. It is important for winemakers to monitor and control the levels of 4-ethylphenol in their products.

Related pages

• Phenol
• Brettanomyces
• Wine chemistry
• Fermentation

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  P-Ethylphenol

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  Coumaric acid to 4-ethylphenol

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  Whiplash