Benzoylformate

Benzoylformate refers to the conjugate base of benzoylformic acid (phenylglyoxylic acid) and to the salts and esters derived from that acid. In common usage, the term most often denotes the benzoylformate anion, Ph-CO-COO−, or its metal or ammonium salts. The neutral acid form is benzoylformic acid.

Chemical identity and structure: Benzoylformate is a beta-keto carboxylate, containing an adjacent pair of carbonyl groups (a benzoyl carbonyl linked to a carboxylate). This arrangement gives the compound reactive properties typical of beta-keto acids and their salts, including tendency to decarboxylate under certain conditions.

Preparation and occurrence: It can be prepared by deprotonation of benzoylformic acid with base to give the corresponding salt. In biology and chemistry, benzoylformate appears as an intermediate or substrate in thiamine diphosphate–dependent reactions and related decarboxylation processes.

Uses and relevance: Benzoylformate is used as a substrate in enzymatic decarboxylation studies, notably with benzoylformate decarboxylase, and as a source of benzaldehyde in synthetic transformations. Its properties as a polar, water-soluble salt support aqueous biocatalytic applications and investigations of mechanistic aspects of enzyme-catalyzed decarboxylation.

Safety and handling: As a salt or salt solution of a beta-keto carboxylate, benzoylformate is handled under standard laboratory safety practices. It can undergo decarboxylation upon heating, yielding benzaldehyde and carbon dioxide. Synonyms include phenylglyoxylate and benzoylformic acid salt forms.