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L-3-Phenyllactic acid (PC000464)

Record Information
Version1.0
Creation date2015-10-09 22:30:49 UTC
Update date2017-01-19 02:36:25 UTC
FoodComEx IDPC000464
FoodDB RecordFDB022220
Chemical Information
NameL-3-Phenyllactic acid
DescriptionL-3-Phenyllactic acid (or PLA) is a chiral aromatic compound involved in phenylalanine metabolism. It 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. [HMDB]
CAS Number20312-36-1
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(-)-2-Hydroxy-3-phenylpropanoatehmdb
(-)-2-Hydroxy-3-phenylpropanoic acidhmdb
(-)-2-Hydroxy-3-phenylpropionatehmdb
(-)-2-Hydroxy-3-phenylpropionic acidhmdb
(-)-3-Phenyllactatehmdb
(-)-3-Phenyllactic acidhmdb
(-)-b-phenyllactatehmdb
(-)-b-phenyllactic acidhmdb
(-)-beta-phenyllactatehmdb
(-)-beta-phenyllactic acidhmdb
(2S)-2-hydroxy-3-phenylpropanoatehmdb
(2S)-2-hydroxy-3-phenylpropanoic acidhmdb
(2S)-2-Hydroxy-3-phenylpropionatehmdb
(2S)-2-Hydroxy-3-phenylpropionic acidhmdb
(R)-PhenyllactateChEBI
(R)-Phenyllactic acidGenerator
(S)-3-phenyl-Lactatehmdb
(S)-3-phenyl-Lactic acidhmdb
(S)-3-phenyllactic acidhmdb
(s)-a-hydroxy-benzenepropanoatehmdb
(s)-a-hydroxy-benzenepropanoic acidhmdb
(s)-alpha-hydroxy-benzenepropanoatehmdb
(s)-alpha-hydroxy-benzenepropanoic acidhmdb
(s)-b-phenyllactichmdb
(s)-beta-phenyllactichmdb
Alpha-hydroxy-beta-phenyl-propionic acidhmdb
D-3-PhenyllactateGenerator
D-3-Phenyllactic acidChEBI
HFAhmdb
L-(-)-3-phenyllactic acidhmdb
L-2-hydroxy-3-phenyl-propionic acidhmdb
L-3-Phenyllactatehmdb
L-beta-phenyllactic acidhmdb
L-phenyl lactatehmdb
Chemical FormulaC9H10O3
IUPAC name(2R)-2-hydroxy-3-phenylpropanoic acid
InChI IdentifierInChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/m1/s1
InChI KeyVOXXWSYKYCBWHO-MRVPVSSYSA-N
Isomeric SMILESO[C@H](CC1=CC=CC=C1)C(O)=O
Average Molecular Weight166.1739
Monoisotopic Molecular Weight166.062994186
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Alpha-hydroxy acid
  • Monocyclic benzene moiety
  • Hydroxy acid
  • Benzenoid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 200 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
Not Available