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Phenylglyoxylic acid

From Wikipedia, the free encyclopedia
Phenylglyoxylic acid
Names
Preferred IUPAC name
Oxo(phenyl)acetic acid
Other names
Benzoyl formate
Phenylglyoxalic acid
Phenylglyoxylate
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.009.345 Edit this at Wikidata
EC Number
  • 210-278-7
KEGG
UNII
  • 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
  • C1=CC=C(C=C1)C(=O)C(=O)O
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]
  1. ^ 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.
  2. ^ T. S. Oakwood and C. A. Weisgerber (1955). "Benzoylformic Acid". Organic Syntheses; Collected Volumes, vol. 3, p. 114.