Phenylglyoxylic acid

Phenylglyoxylic acid
Names
	Preferred IUPAC name Oxo(phenyl)acetic acid
	Other names Benzoyl formate; Phenylglyoxalic acid; Phenylglyoxylate
Identifiers
CAS Number	611-73-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18280 ;
ChemSpider	11421 ;
ECHA InfoCard	100.009.345
EC Number	210-278-7;
KEGG	C02137 ;
PubChem CID	11915;
UNII	2PZL5A0W0M ;
CompTox Dashboard (EPA)	DTXSID80209993 ;
	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
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). verify (what is ?) 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⁺ ⇌ benzaldehyde + CO₂

It is a colourless solid with a melting point of 64–66 °C and is moderately acidic (pK_a = 2.15).

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

Names

Preferred IUPAC name Oxo(phenyl)acetic acid
Other names Benzoyl formate Phenylglyoxalic acid Phenylglyoxylate
Identifiers
CAS Number	611-73-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18280^N
ChemSpider	11421^N
ECHA InfoCard	100.009.345
EC Number	210-278-7
KEGG	C02137^N
PubChem CID	11915
UNII	2PZL5A0W0M^Y
CompTox Dashboard (EPA)	DTXSID80209993
InChI InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)^N Key: FAQJJMHZNSSFSM-UHFFFAOYSA-N^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
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). N verify (what is ^YN ?) Infobox references