Phenylglyoxalic acid
From Wikipedia, the free encyclopedia
| Phenylglyoxalic acid | |
|---|---|
 |
|
| IUPAC name | 2-Oxo-2-phenylacetic acid |
| Other names | Benzoyl formate Phenylglyoxalate |
| Identifiers | |
| CAS number | [611-73-4] |
| PubChem | |
| SMILES | C1=CC=C(C=C1)C(=O)C(=O)O |
| Properties | |
| Molecular formula | C8H6O3 |
| Molar mass | 150.13 g/mol |
| Melting point |
64–66 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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Phenylglyoxalic acid is the organic compound with the formula C6H5C(O)CO2H. The conjugate base, known as benzoyl formate is the substrate of benzoylformate decarboxylase, a thiamine diphosphate-dependent enzyme:
- benzoylformate + H+
benzaldehyde + CO2
It is a colourless solid, m.p. 64–66 °C.
Phenylglyoxalic acid can be synthetized by oxidation of mandelic acid with potassium permanganate.[1] An alternative synthesis involves hydrolysis of benzoyl cyanide.[2]
[edit] References
- ^ B. B. Corson, Ruth A. Dodge, S. A. Harris, and R. K. Hazen (1941). "Ethyl Benzoylformate". Org. Synth.; Coll. Vol. 1: 241.
- ^ T. S. Oakwood and C. A. Weisgerber (1955). "Benzoylformic Acid". Org. Synth.; Coll. Vol. 3: 114.
