Record Information
Creation date2015-10-09 22:27:59 UTC
Update date2017-01-19 02:36:12 UTC
FoodComEx IDPC000072
FoodDB RecordFDB008272
Chemical Information
Name2-Oxo-3-phenylpropanoic acid (Mixture oxo and keto)
DescriptionPhenylpyruvic 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 Number156-06-9
2-Hydroxy-3-phenyl-2-propenoic acid, 9CIdb_source
3-Phenyl-2-oxopropanoic acidChEBI
a-Hydroxycinnamic aciddb_source
a-Ketohydrocinnamic acidGenerator
a-oxo-Benzenepropanoic acidGenerator
a-Oxobenzenepropanoic acid, 9CIdb_source
alpha-Ketohydrocinnamic acidChEBI
alpha-oxo-Benzenepropanoic acidChEBI
b-Phenylpyruvic acidGenerator
beta-Phenylpyruvic acidChEBI
FEMA 3892db_source
keto-Phenylpyruvic acidGenerator
Phenylpyroracemic acidHMDB
Phenylpyruvic aciddb_source
α-ketohydrocinnamic acidGenerator
α-oxo-benzenepropanoic acidGenerator
β-phenylpyruvic acidGenerator
Chemical FormulaC9H8O3
IUPAC name2-oxo-3-phenylpropanoic acid
InChI IdentifierInChI=1S/C9H8O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,11,12)
Isomeric SMILESOC(=O)C(=O)CC1=CC=CC=C1
Average Molecular Weight164.158
Monoisotopic Molecular Weight164.047344122
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpyruvic acid derivatives
Direct ParentPhenylpyruvic acid derivatives
Alternative Parents
  • Phenylpyruvate
  • 3-phenylpropanoic-acid
  • Keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointMp 157° dec.DFC
Foods of Origin
FoodContent Range AverageReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 4 g
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez
Commercial Vendors
AKSci 7828AA
AKSci HMDB0000205
MetaSci HMDB0000205