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 ;
EC Number	210-278-7;
KEGG	C02137 ;
PubChem CID	11915;
UNII	2PZL5A0W0M ;
	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.^[1] An alternative synthesis involves hydrolysis of benzoyl cyanide.^[2]

References

↑ B. B. Corson, Ruth A. Dodge, S. A. Harris, and R. K. Hazen (1941). "Ethyl Benzoylformate". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=CV1P0241. ; Collective Volume, 1, pp. 241
↑ T. S. Oakwood and C. A. Weisgerber (1955). "Benzoylformic Acid". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv3p0114. ; Collective Volume, 3, pp. 114

0.00

(0 votes)

Original source: https://en.wikipedia.org/wiki/Phenylglyoxylic acid. Read more

[1] B. B. Corson, Ruth A. Dodge, S. A. Harris, and R. K. Hazen (1941). "Ethyl Benzoylformate". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=CV1P0241. ; Collective Volume, 1, pp. 241

[2] T. S. Oakwood and C. A. Weisgerber (1955). "Benzoylformic Acid". Organic Syntheses. http://www.orgsyn.org/demo.aspx?prep=cv3p0114. ; Collective Volume, 3, pp. 114

[1]

[2]

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
EC Number	210-278-7
KEGG	C02137^N
PubChem CID	11915
UNII	2PZL5A0W0M^Y
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

Phenylglyoxylic acid

Topic: Chemistry

References