Phenylglyoxylic acid
Appearance
(Redirected from Phenylglyoxalic acid)
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Names | |
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Preferred IUPAC name
Oxo(phenyl)acetic acid | |
Other names
Benzoyl formate
Phenylglyoxalic acid Phenylglyoxylate | |
Identifiers | |
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ECHA InfoCard | 100.009.345 |
EC Number |
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PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C8H6O3 | |
Molar mass | 150.13 g/mol |
Appearance | colorless solid |
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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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+ ⇌ benzaldehyde + CO2
It is a colourless solid with a melting point of 64–66 °C and is moderately acidic (pKa = 2.15).
Phenylglyoxylic acid can be synthesized by oxidation of mandelic acid with potassium permanganate.[1] An alternative synthesis involves hydrolysis of benzoyl cyanide.[2]
References
[edit]- ^ B. B. Corson, Ruth A. Dodge, S. A. Harris, and R. K. Hazen (1941). "Ethyl Benzoylformate". Organic Syntheses
{{cite journal}}
: CS1 maint: multiple names: authors list (link); Collected Volumes, vol. 1, p. 241. - ^ T. S. Oakwood and C. A. Weisgerber (1955). "Benzoylformic Acid". Organic Syntheses; Collected Volumes, vol. 3, p. 114.