Phenylpyruvic acid

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Phenylpyruvic acid
Phenylpyruvic acid.png
Names
IUPAC name
2-Oxo-3-phenylpropanoic acid
Other names
Phenylpyruvate; 3-Phenylpyruvic acid; Keto-phenylpyruvate; beta-Phenylpyruvic acid
Identifiers
156-06-9 YesY
ChEBI CHEBI:30851 N
ChemSpider 972 N
Jmol 3D model Interactive image
PubChem 997
Properties
C9H8O3
Molar mass 164.16 g·mol−1
Melting point 155 °C (311 °F; 428 K) (decomposes)
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

Phenylpyruvic acid is the organic compound with the formula C6H5CH2C(O)CO2H. It is a keto acid.

Occurrence and properties[edit]

The compound exists in equilibrium with its E- and Z-enol tautomers. It is a product from the oxidative deamination of phenylalanine.

Preparation[edit]

It is prepared by condensation of benzaldehyde and glycine derivatives to give phenylazlactone, which is then hydrolyzed with acid- or base-catalysis.[1] It can also be synthesized from benzyl chloride by double carbonylation.[2][3]

See also[edit]

References[edit]

  1. ^ Carpy, Alain J. M.; Haasbroek, Petrus P.; Oliver, Douglas W. "Phenylpyruvic acid derivatives as enzyme inhibitors: Therapeutic potential on macrophage migration inhibitory factor" Medicinal Chemistry Research 2004, volume 13, pp. 565-577.
  2. ^ Wolfram, Joachim. "Preparation of α-keto-carboxylic acids from acyl halides". Google Patents US4481368 & US4481369. Ethyl Corporation. 
  3. ^ Werner Bertleff, Michael Roeper, & Xavier Sava (2007). "Carbonylation". Ullmann's Encyclopedia of Industrial Chemistry: pg.19. doi:10.1002/14356007.a05_217.pub2.