FComEx: Phenyllactic acid (PC000370)

Record Information

Version

1.0

Creation date

2015-10-09 22:30:16 UTC

Update date

2017-01-19 02:36:21 UTC

FoodComEx ID

PC000370

FoodDB Record

FDB022236

Chemical Information

Name

Phenyllactic acid

Description

Phenyllactic acid a product of phenylalanine catabolism, appearing prominently in the urine in individuals with phenylketonuria. Levels of several phenylalanine metabolites, including phenylacetate (PAA), phenyllactate (PLA), and phenylpyruvate (PPA)) are elevated in Phenylketonuria (PKU) (OMIM 261600). Phenyllactic acid is likely produced from phenylpyruvate via the action of lactate dehydrogenase. The D-form of this organic acid is typically derived from bacterial sources while the L-form is almost certainly endogenous. Levels of phenyllactate are normally very low in blood or urine. High levels of PLA in the urine or blood are often indicative of phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid (a precursor of phenylactate). In particular, excessive phenylalanine is typically metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid and then to phenyllactate through the action of lactate dehydrogenase. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. 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. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation. PMID: 10790306; OMIM: 261600 [HMDB]

CAS Number

828-01-3

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
2-Hydroxy-3-phenylpropanoate	hmdb
2-Hydroxy-3-phenylpropanoic acid	hmdb
2-Hydroxy-3-phenylpropionate	hmdb
2-Hydroxy-3-phenylpropionic acid	manual
3-Phenyl-2-hydroxypropanoate	hmdb
3-Phenyl-2-hydroxypropanoic acid	hmdb
3-Phenyllactate	hmdb
3-Phenyllactic acid	manual
a-Hydroxybenzenepropanoate	hmdb
a-Hydroxybenzenepropanoic acid	hmdb
alpha-Hydroxybenzenepropanoate	hmdb
alpha-Hydroxybenzenepropanoic acid	hmdb
b-Phenyllactate	hmdb
b-Phenyllactic acid	Generator
beta-Phenyllactate	hmdb
beta-Phenyllactic acid	manual
DL-2-Hydroxy-3-phenylpropionate	hmdb
DL-2-Hydroxy-3-phenylpropionic acid	hmdb
DL-3-Phenyllactate	hmdb
DL-3-Phenyllactic acid	manual
DL-b-Phenyllactate	hmdb
DL-b-Phenyllactic acid	hmdb
DL-beta-Phenyllactate	hmdb
DL-beta-Phenyllactic acid	manual
DL-β-phenyllactate	Generator
DL-β-phenyllactic acid	Generator
Phenyllactate	hmdb
β-phenyllactate	Generator
β-phenyllactic acid	Generator

Chemical Formula

C9H10O3

IUPAC name

2-hydroxy-3-phenylpropanoic acid

InChI Identifier

InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)

InChI Key

VOXXWSYKYCBWHO-UHFFFAOYSA-N

Isomeric SMILES

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

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Not Available

Direct Parent

Benzene and substituted derivatives

Alternative Parents