Phenylpyruvic acid
 | |
| Names | |
|---|---|
| IUPAC name
2-Oxo-3-phenylpropanoic acid | |
| Other names
Phenylpyruvate; 3-Phenylpyruvic acid; Keto-phenylpyruvate; beta-Phenylpyruvic acid | |
| Identifiers | |
156-06-9  | |
| 3D model (Jmol) | Interactive image |
| ChEBI | CHEBI:30851  |
| ChemSpider | 972 |
| ECHA InfoCard | 100.005.317 |
| 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). | |
| verify (what is ?) | |
| Infobox references | |
Phenylpyruvic acid is the organic compound with the formula C6H5CH2C(O)CO2H. It is a keto acid.
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
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
References
- ↑ 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.
- ↑ Wolfram, Joachim. "Preparation of α-keto-carboxylic acids from acyl halides". Google Patents US4481368 & US4481369. Ethyl Corporation.
- ↑ Werner Bertleff, Michael Roeper, & Xavier Sava (2007). "Carbonylation". Ullmann's Encyclopedia of Industrial Chemistry: pg.19. doi:10.1002/14356007.a05_217.pub2.
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