Phenylpyruvic acid

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

Phenylpyruvic acid

Names
IUPAC name 2-Oxo-3-phenylpropanoic acid
Other names Phenylpyruvate; 3-Phenylpyruvic acid; Keto-phenylpyruvate; beta-Phenylpyruvic acid
Identifiers
CAS Number	156-06-9
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30851
ChemSpider	972
ECHA InfoCard	100.005.317
PubChem CID	997
UNII	X7CO62M413
CompTox Dashboard (EPA)	DTXSID1042281
InChI InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12) Key: InChIKey=BTNMPGBKDVTSJY-UHFFFAOYSA-N
SMILES C1=CC=C(C=C1)CC(=O)C(=O)O
Properties
Chemical formula	C9H8O3
Molar mass	164.160 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

Occurrence and properties

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

Preparation and reactions

It can be prepared by many methods. Classically it is produced from aminocinnamic acid derivatives.[1] It has been prepared by condensation of benzaldehyde and glycine derivatives to give phenylazlactone, which is then hydrolyzed with acid- or base-catalysis.[2] It can also be synthesized from benzyl chloride by double carbonylation.[3][4]

Reductive amination of phenylpyruvic acid gives phenylalanine.

See also

• Phenylpyruvate decarboxylase
• Phenylpyruvate tautomerase
• Phenylketonuria

References

1. R. M. Herbst, D. Shemin (1939). "Phenylpyruvic Acid". Organic Syntheses. 19: 77. doi:10.15227/orgsyn.019.0077.
2. 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.
3. Wolfram, Joachim. "Preparation of α-keto-carboxylic acids from acyl halides". Google Patents US4481368 & US4481369. Ethyl Corporation.
4. Werner Bertleff; Michael Roeper; Xavier Sava (2007). "Carbonylation". Ullmann's Encyclopedia of Industrial Chemistry: pg.19. doi:10.1002/14356007.a05_217.pub2. ISBN 978-3527306732. |page(s)= has extra text (help)