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Identification
YMDB IDYMDB00891
NamePhenylacetic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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 weakly acidic compound (based on its pKa). Phenylacetic acid exists in all living species, ranging from bacteria to humans. Phenylacetic acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2-Phenylacetate
  • 2-Phenylacetic acid
  • 2-phenylethanoate
  • 2-phenylethanoic acid
  • a-Toluate
  • a-Toluic acid
  • alpha-Toluate
  • alpha-Toluic acid
  • Benzeneacetate
  • Benzeneacetic acid
  • Benzylformate
  • Benzylformic acid
  • omega-Phenylacetate
  • omega-Phenylacetic acid
  • Phenylacetate
  • Phenylacetic acid
  • Phenylethanoate
  • Phenylethanoic acid
  • w-Phenylacetate
  • w-Phenylacetic acid
  • PA
  • Α-toluate
  • Α-toluic acid
  • Phenylacetic acid, potassium salt
  • Sodium phenylacetate
  • Phenylacetic acid, lithium salt
  • Phenylacetic acid, sodium salt
  • Phenylacetic acid, ammonium salt
  • Phenylacetic acid, calcium salt
  • Phenylacetic acid, cesium salt
  • Phenylacetic acid, mercury salt
  • Phenylacetic acid, rubidium salt
  • Phenylacetic acid, sodium salt , carboxy-(11)C-labeled CPD
CAS number103-82-2
WeightAverage: 136.1479
Monoisotopic: 136.0524295
InChI KeyWLJVXDMOQOGPHL-UHFFFAOYSA-N
InChIInChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
IUPAC Name2-phenylacetic acid
Traditional IUPAC Nameω-phenylacetic acid
Chemical FormulaC8H8O2
SMILES[H]OC(=O)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H]
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
Charge0
Melting point76.7 °C
Experimental Properties
PropertyValueReference
Water Solubility16.6 mg/mL at 20 oC [CHIOU,CT et al. (1977)]PhysProp
LogP1.41 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility3.61 g/LALOGPS
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
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic Properties
Flavour/OdourSource
CivetFDB010558
FloralFDB010558
FlowerFDB010558
HoneyFDB010558
HoneysuckleFDB010558
SourFDB010558
SweetFDB010558
WaxyFDB010558
SMPDB Pathways
Phenylalanine metabolismPW002437 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Phenylalanine metabolismec00360 Map00360
SMPDB ReactionsNot Available
KEGG Reactions
Phenylacetaldehyde + NAD + waterNADH + hydron + Phenylacetic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Vuralhan, Z., Morais, M. A., Tai, S. L., Piper, M. D., Pronk, J. T. (2003). "Identification and characterization of phenylpyruvate decarboxylase genes in Saccharomyces cerevisiae." Appl Environ Microbiol 69:4534-4541.12902239
Synthesis Reference:Zhou, Shu-jing; Li, Jin-lian; Luan, Fang. New synthetic method for benzeneacetic acid. Huaxue Yu Shengwu Gongcheng (2005), 22(2), 43-44.
External Links:
ResourceLink
CHEBI ID30745
HMDB IDHMDB00209
Pubchem Compound ID999
Kegg IDC07086
ChemSpider ID10181341
FOODB IDFDB010558
WikipediaPhenylacetic_acid
BioCyc IDPHENYLACETATE

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD2
Uniprot ID:
P47771
Molecular weight:
55187.39844
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.
General function:
Involved in oxidoreductase activity
Specific function:
An aldehyde + NAD(P)(+) + H(2)O = an acid + NAD(P)H
Gene Name:
ALD3
Uniprot ID:
P54114
Molecular weight:
55384.80078
Reactions
An aldehyde + NAD(P)(+) + H(2)O → an acid + NAD(P)H.