Phenylglyoxylic acid

Phenylglyoxylic acid

Names
IUPAC name 2-Oxo-2-phenylacetic acid
Other names Benzoyl formate Phenylglyoxalic acid Phenylglyoxylate
Identifiers
CAS Number	611-73-4
ChEBI	CHEBI:18280
ChemSpider	11421
EC Number	210-278-7
Jmol interactive 3D	Image
KEGG	C02137
PubChem	11915
InChI InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11) Key: FAQJJMHZNSSFSM-UHFFFAOYSA-N InChI=1/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11) Key: FAQJJMHZNSSFSM-UHFFFAOYAS
SMILES C1=CC=C(C=C1)C(=O)C(=O)O
Properties
Chemical formula	C8H6O3
Molar mass	150.13 g/mol
Melting point	64 to 66 °C (147 to 151 °F; 337 to 339 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Phenylglyoxylic acid is the organic compound with the formula C₆H₅C(O)CO₂H. The conjugate base, known as benzoylformate is the substrate of benzoylformate decarboxylase, a thiamine diphosphate-dependent enzyme:

benzoylformate + H⁺ $\rightleftharpoons$ benzaldehyde + CO₂

It is a colourless solid, m.p. 64–66 °C.

Phenylglyoxylic acid can be synthesized by oxidation of mandelic acid with potassium permanganate.^[1] An alternative synthesis involves hydrolysis of benzoyl cyanide.^[2]

References

1. B. B. Corson, Ruth A. Dodge, S. A. Harris, and R. K. Hazen (1941). "Ethyl Benzoylformate". Org. Synth.; Coll. Vol. 1, p. 241
2. T. S. Oakwood and C. A. Weisgerber (1955). "Benzoylformic Acid". Org. Synth.; Coll. Vol. 3, p. 114