Hippuric acid

Hippuric acid is an organic acid formed when benzoic acid combines with glycine. Humans and other mammals excrete it in urine.

Benzoic acid: Benzoic acid is an aromatic carboxylic acid found naturally and used as a food preservative. It supplies the benzoate that is conjugated to form hippuric acid.
Toluene: Toluene is an aromatic solvent and fuel component that the body metabolizes largely into benzoic acid. Toluene exposure can increase urinary hippuric acid after oxidation to benzoate.
Aromatic compound: An aromatic compound contains a cyclic, conjugated electron system with unusual stability. Hippuric acid contains a benzene ring inherited from its benzoate component.
Justus von Liebig: Justus von Liebig was a German chemist who helped establish modern organic and agricultural chemistry. Liebig investigated hippuric acid in urine and helped establish its chemical identity.
Glycine: Glycine is the simplest protein-building amino acid and a substrate in many metabolic pathways. Its amino group couples with benzoyl-CoA during hippuric acid synthesis.
Biomonitoring: Biomonitoring measures chemicals or their metabolites in biological samples to assess exposure. Urinary hippuric acid has been used as a biomarker of toluene exposure.
Carboxylic acid: A carboxylic acid is an organic compound containing a carbonyl group bonded to a hydroxyl group. Hippuric acid’s acidic behavior comes from its carboxyl group.
Uroscopy: Uroscopy is the historical examination of urine for signs of disease. Urine analysis provided the setting in which hippuric acid became a chemical object of study.
Benzoyl-CoA: Benzoyl-CoA is an activated form of benzoic acid bound to coenzyme A. This activated intermediate enables transfer of the benzoyl group to glycine.
Sodium benzoate: Sodium benzoate is the sodium salt of benzoic acid, used mainly as a food preservative. Its benzoate is metabolized to hippuric acid and can affect urinary levels.

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Benzoyl chlorideBroader topic: Benzoyl chloride can benzoylate glycine in preparations of this compound.