Phenylacetic Acid

Description

Phenylacetic acid, also known by various synonyms, is an organic compound containing a phenyl functional group and a carboxylic acid functional group. It is a white solid with a strong honey-like odor. Endogenously, it is a catabolite of phenylalanine.

As a commercial chemical, it can be used in the illicit production of phenylacetone (used in the manufacture of substituted amphetamines), it is subject to controls in countries including the United States and China.

Occurrence

Phenylacetic acid has been found to be an active auxin (a type of plant hormone), found predominantly in fruits. However, its effect is much weaker than the effect of the basic auxin molecule indole-3-acetic acid. In addition the molecule is naturally produced by the metapleural gland of most ant species and used as an antimicrobial. It is also the oxidation product of phenethylamine in humans following metabolism by monoamine oxidase and subsequent metabolism of the intermediate product, phenylacetaldehyde, by the aldehyde dehydrogenase enzyme; these enzymes are also found in many other organisms. Crypto Mining Hardware

Preparation

This compound may be prepared by the hydrolysis of benzyl cyanide:

Applications

Phenylacetic acid is used in some perfumes, as it possesses a honey-like odor even in low concentrations. It is also used in penicillin G production and diclofenac production. It is also employed to treat type II hyperammonemia to help reduce the amounts of ammonia in a patient’s bloodstream by forming phenylacetyl-CoA, which then reacts with nitrogen-rich glutamine to form phenylacetylglutamine. This compound is then excreted from the patient’s body. It’s also used in the illicit production of phenylacetone, which is used in the manufacture of methamphetamine.

Synonym(s):

2-Phenylethanoic acid
α-Toluic acid
Benzeneacetic acid
2-Phenylacetic acid
β-Phenylacetic acid
PAA
α-Tolylic acid