FComEx: 2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto) (PC000072)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:59 UTC

Update date

2017-01-19 02:36:12 UTC

FoodComEx ID

PC000072

FoodDB Record

FDB008272

Chemical Information

Name

2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto)

Description

Phenylpyruvic acid, also known as keto-phenylpyruvate or a-ketohydrocinnamate, belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid. Phenylpyruvic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylpyruvic acid exists in all living species, ranging from bacteria to humans. Within humans, phenylpyruvic acid participates in a number of enzymatic reactions. In particular, phenylpyruvic acid and L-glutamic acid can be biosynthesized from L-phenylalanine and oxoglutaric acid; which is mediated by the enzyme aspartate aminotransferase, cytoplasmic. In addition, phenylpyruvic acid can be biosynthesized from L-phenylalanine through the action of the enzyme L-amino-acid oxidase. In humans, phenylpyruvic acid is involved in the metabolic disorder called tyrosinemia type 3 (tyro3). Phenylpyruvic acid is a potentially toxic compound. Phenylpyruvic acid, with regard to humans, has been found to be associated with the diseases such as primary biliary cirrhosis; phenylpyruvic acid has also been linked to the inborn metabolic disorder phenylketonuria. High levels of phenylpyruvic acid can be found in the urine of individuals with phenylketonuria (PKU), an inborn error of metabolism. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid. Metabolites of this transamination reaction include phenylacetate, Phenylpyruvic acid and phenethylamine. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed.

CAS Number

156-06-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
2-Hydroxy-3-phenyl-2-propenoic acid, 9CI	db_source
2-oxo-3-Phenylpropanoate	HMDB
3-Phenyl-2-oxopropanoate	ChEBI
3-Phenyl-2-oxopropanoic acid	ChEBI
3-PHENYLPYRUVate	Generator
3-PHENYLPYRUVIC ACID	ChEBI
a-Hydroxycinnamic acid	db_source
a-Ketohydrocinnamate	Generator
a-Ketohydrocinnamic acid	Generator
a-oxo-Benzenepropanoate	Generator
a-oxo-Benzenepropanoic acid	Generator
a-Oxobenzenepropanoic acid, 9CI	db_source
alpha-Ketohydrocinnamate	Generator
alpha-Ketohydrocinnamic acid	ChEBI
alpha-oxo-Benzenepropanoate	Generator
alpha-oxo-Benzenepropanoic acid	ChEBI
b-Phenylpyruvate	Generator
b-Phenylpyruvic acid	Generator
beta-Phenylpyruvate	Generator
beta-Phenylpyruvic acid	ChEBI
FEMA 3892	db_source
keto-Phenylpyruvate	ChEBI
keto-Phenylpyruvic acid	Generator
Phenylbrenztraubensaeure	ChEBI
Phenylpyroracemate	HMDB
Phenylpyroracemic acid	HMDB
Phenylpyruvic acid	db_source
α-ketohydrocinnamate	Generator
α-ketohydrocinnamic acid	Generator
α-oxo-benzenepropanoate	Generator
α-oxo-benzenepropanoic acid	Generator
β-phenylpyruvate	Generator
β-phenylpyruvic acid	Generator

Chemical Formula

C9H8O3

IUPAC name

2-oxo-3-phenylpropanoic acid

InChI Identifier

InChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)

InChI Key

BTNMPGBKDVTSJY-UHFFFAOYSA-N

Isomeric SMILES

OC(=O)C(=O)CC1=CC=CC=C1

Average Molecular Weight

164.158

Monoisotopic Molecular Weight

164.047344122

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpyruvic acid derivatives. Phenylpyruvic acid derivatives are compounds containing a phenylpyruvic acid moiety, which consists of a phenyl group substituted at the second position by an pyruvic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Phenylpyruvic acid derivatives

Direct Parent

Phenylpyruvic acid derivatives

Alternative Parents