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Record Information
Version1.0
Creation Date2016-09-30 22:26:44 UTC
Update Date2020-06-04 21:00:56 UTC
MCDB ID BMDB0000209
Secondary Accession Numbers
  • BMDB00209
Metabolite Identification
Common NamePhenylacetic acid
DescriptionPhenylacetic acid, also known as phenylacetate or alpha-toluic acid, 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. Phenylacetic acid is a drug which is used for use as adjunctive therapy for the treatment of acute hyperammonemia and associated encephalopathy in patients with deficiencies in enzymes of the urea cycle. Phenylacetic acid exists as a solid, possibly soluble (in water), and a weakly acidic compound (based on its pKa) molecule. Phenylacetic acid exists in all living species, ranging from bacteria to humans. In cattle, phenylacetic acid is involved in the metabolic pathway called the phenylacetate metabolism pathway. Phenylacetic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
ValueSource
2-PHENYLACETIC ACIDChEBI
2-Phenylethanoic acidChEBI
alpha-Toluic acidChEBI
Benzeneacetic acidChEBI
Benzylformic acidChEBI
Omega-phenylacetic acidChEBI
PAChEBI
PhenylacetateKegg
2-PHENYLACETateGenerator
2-PhenylethanoateGenerator
a-ToluateGenerator
a-Toluic acidGenerator
alpha-ToluateGenerator
Α-toluateGenerator
Α-toluic acidGenerator
BenzeneacetateGenerator
BenzylformateGenerator
Omega-phenylacetateGenerator
PhenylethanoateHMDB
Phenylethanoic acidHMDB
W-PhenylacetateHMDB
W-Phenylacetic acidHMDB
Phenylacetic acid, potassium saltHMDB
Sodium phenylacetateHMDB
Phenylacetic acid, lithium saltHMDB
Phenylacetic acid, sodium saltHMDB
Phenylacetic acid, ammonium saltHMDB
Phenylacetic acid, calcium saltHMDB
Phenylacetic acid, cesium saltHMDB
Phenylacetic acid, mercury saltHMDB
Phenylacetic acid, rubidium saltHMDB
Phenylacetic acid, sodium salt , carboxy-(11)C-labeled CPDHMDB
Chemical FormulaC8H8O2
Average Molecular Weight136.1479
Monoisotopic Molecular Weight136.0524295
IUPAC Name2-phenylacetic acid
Traditional Nameω-phenylacetic acid
CAS Registry Number103-82-2
SMILES
OC(=O)CC1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
InChI KeyWLJVXDMOQOGPHL-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Monocyclic benzene moiety
  • 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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point76.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility16.6 mg/mLNot Available
LogP1.41HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.72ALOGPS
logP1.61ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)4.55ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.37 m³·mol⁻¹ChemAxon
Polarizability13.85 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0000209
DrugBank IDDB09269
Phenol Explorer Compound IDNot Available
FoodDB IDFDB031100
KNApSAcK IDC00000750
Chemspider ID10181341
KEGG Compound IDC07086
BioCyc IDPHENYLACETATE
BiGG ID1486426
Wikipedia LinkPhenylacetic_acid
METLIN ID129
PubChem Compound999
PDB IDNot Available
ChEBI ID30745
References
Synthesis ReferenceZhou, Shu-jing; Li, Jin-lian; Luan, Fang. New synthetic method for benzeneacetic acid. Huaxue Yu Shengwu Gongcheng (2005), 22(2), 43-44.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]