Phenylpyruvic acid
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| Watchedfields = changed
| verifiedrevid = 393617427
| ImageFile =2-oxo-3-phenylpropanoic acid 200.svg
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| PIN =2-Oxo-3-phenylpropanoic acid
| OtherNames =Phenylpyruvate; 3-Phenylpyruvic acid; Keto-phenylpyruvate; beta-Phenylpyruvic acid
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo =156-06-9
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = X7CO62M413
| PubChem =997
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 30851
| SMILES = c1ccccc1CC(=O)C(=O)O
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = InChIKey=BTNMPGBKDVTSJY-UHFFFAOYSA-N
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 972
}}
|Section2={{Chembox Properties
| C=9 | H=8 | O=3
| Appearance =
| Density =
| MeltingPtC = 155
| MeltingPt_notes = (decomposes)
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|Section3={{Chembox Hazards
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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.{{cn|date=July 2024}} 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.{{cite journal|doi=10.15227/orgsyn.019.0077|title=Phenylpyruvic Acid|journal=Organic Syntheses|author=R. M. Herbst, D. Shemin|volume=19|pages=77|year=1939}} It has been prepared by condensation of benzaldehyde and glycine derivatives to give phenylazlactone, which is then hydrolyzed with acid- or base-catalysis.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. It can also be synthesized from benzyl chloride by double carbonylation.{{cite web|last1=Wolfram|first1=Joachim|title=Preparation of α-keto-carboxylic acids from acyl halides|url=https://patents.google.com/patent/US4481369?oq=4481369|website=Google Patents US4481368 & US4481369|publisher=Ethyl Corporation}}{{cite journal|author1=Werner Bertleff |author2=Michael Roeper |author3=Xavier Sava |title=Carbonylation|journal=Ullmann's Encyclopedia of Industrial Chemistry|date=2007|page=19|doi=10.1002/14356007.a05_217.pub2|isbn=978-3527306732 }}
Reductive amination of phenylpyruvic acid gives phenylalanine.