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
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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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 (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

  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); Collective Volume, vol. 1, p. 241
  2. ↑ T. S. Oakwood and C. A. Weisgerber (1955). "Benzoylformic Acid". Organic Syntheses.; Collective Volume, vol. 3, p. 114
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