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Record Information
Version1.0
Creation Date2016-07-13 19:42:15 UTC
Update Date2016-07-20 20:50:31 UTC
LmdbLMDB00095
Secondary Accession NumbersNone
Metabolite Identification
Common NamePhenylacetic acid
DescriptionPhenyl acetate (or phenylacetate) is a carboxylic acid ester that has been found in the biofluids of patients with nephritis and/or hepatitis as well as patients with phenylketonuria (PKU). Excess phenylalanine in the body can be disposed of through a transamination process leading to the production of phenylpyruvate. The phenylpyruvate can be further metabolized into a number of products. Decarboxylation of phenylpyruvate gives phenylacetate, while a reduction reaction gives phenyllactate. The phenylacetate can be further conjugated with glutamine to give phenylacetyl glutamine. All of these metabolites can be detected in serum and urine of PKU patients. Phenyl acetate is also produced endogenously as the metabolite of 2-Phenylethylamine, which is mainly metabolized by monoamine oxidase to form phenyl acetate. 2-phenylethylamine is an "endogenous amphetamine" which may modulate central adrenergic functions, and the urinary phenyl acetate levels have been postulated as a marker for depression. (PMID: 17978765 , 476920 , 6857245 ). Phenylacetate is also found in essential oils, e.g. neroli, rose oil, free and as esters' and in many fruits. As a result it is used as a perfumery and flavoring ingredient.
Structure
Thumb
Synonyms
ValueSource
2-PHENYLACETIC ACIDChEBI
2-Phenylethanoic acidChEBI
alpha-Toluic acidChEBI
Benzeneacetic acidChEBI
Benzylformic acidChEBI
Omega-phenylacetic acidChEBI
PAChEBI
PhenylacetateKegg
2-PHENYLACETateGenerator
a-ToluateGenerator
a-Toluic acidGenerator
alpha-ToluateGenerator
Α-toluateGenerator
Α-toluic acidGenerator
BenzeneacetateGenerator
BenzylformateGenerator
Omega-phenylacetateGenerator
PhenylethanoateHMDB
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
PAAPhytoBank
ω-Phenylacetic acidPhytoBank
Phenylacetic acidHMDB
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
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-9700000000-c07461cdad68959aa53fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-de65c7c0092343a4e599Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9700000000-c07461cdad68959aa53fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-9700000000-43e86e45beae2fa6704fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-dc43e5e062b0ed500c5fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9100000000-aaef76d181aebe492bbeSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9100000000-de65c7c0092343a4e599Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-9000000000-6ca33b098558bf13801cSpectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-f898aafe4cecc87d26f1Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9400000000-aa5bff1d7a8df7c97bdbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-6a017c8136a375269f3eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-2900000000-d79f9224f2390d6b17a2Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-e712b088c9a3d3855ec7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-01ri-9000000000-f0ed89dae2c22d4c538cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-053i-2900000000-3e4bf20b985893f203e7Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-5419b00a9c7c126093dbSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-1900000000-9a2e089c5511fa2bf210Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-2900000000-94a6f40f937bf9d7e4c7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9500000000-8d3540e40bfc0e4c0e5fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-417ad1f13a593ac780b9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-5900000000-0ed04a623daaf32fffdaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-8900000000-709928d6b823240d3528Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9600000000-4a7739132344f3dec710Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-5671d4c535a6553aaf0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-5671d4c535a6553aaf0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5e37e9f4d7b24c763302Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-9800000000-aacb25995ab02725e0f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-930a2cbe3e9fb1915075Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-199de8006c0d100aaabbSpectrum
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-1e23fd8e6ce900cd8e4cSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Milk
  • Plasma
  • Ruminal Fluid
  • Serum
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableEquine
    • E. E. Escalona, J...
details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified302 +/- 86 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified317 +/- 62 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified317 +/- 62 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified462 +/- 121 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified541 +/- 118 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified640 +/- 101 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified241 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified363 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified371 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified443 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified347.5 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified480.5 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified582.2 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified640.5 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified219 +/- 6.4 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified343 +/- 22 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified379 +/- 26 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified708 +/- 77 uMNot AvailableCaprine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
SerumDetected but not QuantifiedNot ApplicableNot AvailableCaprine details
DrugBank IDDB09269
HMDB IDHMDB0000209
FooDB IDFDB031100
Phenol Explorer IDNot Available
KNApSAcK IDC00000750
BiGG ID1486426
BioCyc IDPHENYLACETATE
METLIN ID129
PDB IDNot Available
Wikipedia LinkPhenylacetic_acid
Chemspider ID10181341
ChEBI ID30745
PubChem Compound ID999
Kegg Compound IDC07086
YMDB IDYMDB00891
ECMDB IDECMDB21416
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ostergaard J, Larsen C: Bioreversible derivatives of phenol. 2. Reactivity of carbonate esters with fatty acid-like structures towards hydrolysis in aqueous solutions. Molecules. 2007 Oct 30;12(10):2396-412. [17978765 ]
  2. Lorentz K, Flatter B, Augustin E: Arylesterase in serum: elaboration and clinical application of a fixed-incubation method. Clin Chem. 1979 Oct;25(10):1714-20. [476920 ]
  3. Sabelli HC, Fawcett J, Gusovsky F, Javaid J, Edwards J, Jeffriess H: Urinary phenyl acetate: a diagnostic test for depression? Science. 1983 Jun 10;220(4602):1187-8. [6857245 ]