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| | {{chembox |
| | | verifiedrevid = 374826361 |
| | |ImageFile=Phenylglyoxalic acid.png |
| | |ImageSize=200px |
| | |IUPACName=2-Oxo-2-phenylacetic acid |
| | |OtherNames=Benzoyl formate<br>Phenylglyoxalic acid<br>Phenylglyoxylate |
| | |Section1= {{Chembox Identifiers |
| | | CASNo_Ref = {{cascite|correct|CAS}} |
| | | CASNo=611-73-4 |
| | | PubChem=11915 |
| | | SMILES=C1=CC=C(C=C1)C(=O)C(=O)O |
| | }} |
| | |Section2= {{Chembox Properties |
| | | Formula=C<sub>8</sub>H<sub>6</sub>O<sub>3</sub> |
| | | MolarMass=150.13 g/mol |
| | | Appearance= |
| | | Density= |
| | | MeltingPt=64–66 °C |
| | | BoilingPt= |
| | | Solubility= |
| | }} |
| | |Section3= {{Chembox Hazards |
| | | MainHazards= |
| | | FlashPt= |
| | | Autoignition= |
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| | '''Phenylglyoxylic acid''' is the [[organic compound]] with the formula C<sub>6</sub>H<sub>5</sub>C(O)CO<sub>2</sub>H. The conjugate base, known as benzoyl formate is the substrate of [[benzoylformate decarboxylase]], a [[thiamine diphosphate]]-dependent [[enzyme]]: |
| | :benzoylformate + H<sup>+</sup> <math>\rightleftharpoons</math> [[benzaldehyde]] + CO<sub>2</sub> |
| | It is a colourless solid, m.p. 64–66 °C. |
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| | Phenylglyoxylic acid can be synthesized by oxidation of [[mandelic acid]] with [[potassium permanganate]].<ref>{{OrgSynth | author = B. B. Corson, Ruth A. Dodge, S. A. Harris, and R. K. Hazen | title = Ethyl Benzoylformate | collvol = 1 | collvolpages = 241| year = 1941 | prep = CV1P0241}}</ref> An alternative synthesis involves [[hydrolysis]] of benzoyl cyanide.<ref>{{OrgSynth | author = T. S. Oakwood and C. A. Weisgerber | title = Benzoylformic Acid | collvol = 3 | collvolpages = 114| year = 1955 | prep = cv3p0114}}</ref> |
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| | ==References== |
| | <references/> |
| | |
| | [[Category:Carboxylic acids]] |
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Phenylglyoxylic 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.
Phenylglyoxylic acid can be synthesized by oxidation of mandelic acid with potassium permanganate.[1] An alternative synthesis involves hydrolysis of benzoyl cyanide.[2]
References