Phenylpyruvic acid

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

Phenylpyruvic acid

Names
Preferred IUPAC name 2-Oxo-3-phenylpropanoic acid
Other names Phenylpyruvate; 3-Phenylpyruvic acid; Keto-phenylpyruvate; beta-Phenylpyruvic acid
Identifiers
CAS Number	156-06-9 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:30851 N
ChemSpider	972 N
ECHA InfoCard	100.005.317
PubChem CID	997
UNII	X7CO62M413 Y
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) N Key: InChIKey=BTNMPGBKDVTSJY-UHFFFAOYSA-N N
SMILES c1ccccc1CC(=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). N verify (what is YN ?) Infobox references

Occurrence and properties

The compound exists in equilibrium with its (E)- and (Z)-enol tautomers.^{[citation needed]} It is a product from the oxidative deamination of phenylalanine.

When the activity of the enzyme phenylalanine hydroxylase is reduced, the amino acid phenylalanine accumulates and gets converted into phenylpyruvic acid (phenylpyruvate), which leads to 'Phenylketonuria (PKU)' instead of 'tyrosine' which is the normal product of phenylalanine hydroxylase.

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: 19. doi:10.1002/14356007.a05_217.pub2. ISBN 978-3527306732.