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Phenylacetic acid (FDB010558)

Record Information
Version1.0
Creation date2010-04-08 22:09:11 UTC
Update date2024-11-29 22:26:58 UTC
Primary IDFDB010558
Secondary Accession NumbersNot Available
Chemical Information
FooDB NamePhenylacetic acid
DescriptionFound in essential oils, e.g. neroli, rose oil, free and as estersand is also present in grapes, raspberry, strawberry, cherimoya, other fruits, cheddar cheese, Swiss cheese, wine, black tea, peated malt and other foodstuffs. Flavouring ingredient Phenyl 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.; Phenylacetic acid (abr. PAA and synonyms are: ?-toluic acid, benzeneacetic acid, alpha tolylic acid, 2-phenylacetic acid) is an organic compound containing a phenyl functional group and an acetic acid functional group. It is a white solid with a disagreeable odor. Because it is used in the illicit production of phenylacetone (used in the manufacture of meth/amphetamines), it is subject to controls in the United States.
CAS Number103-82-2
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC8H8O2
IUPAC name2-phenylacetic acid
InChI IdentifierInChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
InChI KeyWLJVXDMOQOGPHL-UHFFFAOYSA-N
Isomeric SMILESOC(=O)CC1=CC=CC=C1
Average Molecular Weight136.1479
Monoisotopic Molecular Weight136.0524295
Classification
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
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 70.58%; H 5.92%; O 23.50%DFC
Melting PointMp 77-78.5°DFC
Boiling PointBp0.01 65-70°DFC
Experimental Water Solubility16.6 mg/mL at 20 oCCHIOU,CT et al. (1977)
Experimental logP1.41HANSCH,C ET AL. (1995)
Experimental pKapKa 4.31 (H2O)DFC
Isoelectric pointNot Available
Charge-1
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-1e23fd8e6ce900cd8e4c2014-09-20View Spectrum
GC-MSPhenylacetic acid, 1 TMS, GC-MS Spectrumsplash10-0006-9700000000-c07461cdad68959aa53fSpectrum
GC-MSPhenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9100000000-de65c7c0092343a4e599Spectrum
GC-MSPhenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9700000000-c07461cdad68959aa53fSpectrum
GC-MSPhenylacetic acid, non-derivatized, GC-MS Spectrumsplash10-0006-9700000000-43e86e45beae2fa6704fSpectrum
Predicted GC-MSPhenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9200000000-dc43e5e062b0ed500c5fSpectrum
Predicted GC-MSPhenylacetic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0006-9100000000-aaef76d181aebe492bbeSpectrum
Predicted GC-MSPhenylacetic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPhenylacetic acid, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9100000000-de65c7c0092343a4e5992012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-9000000000-6ca33b098558bf13801c2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-f898aafe4cecc87d26f12017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9400000000-aa5bff1d7a8df7c97bdb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-6a017c8136a375269f3e2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-2900000000-d79f9224f2390d6b17a22021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-e712b088c9a3d3855ec72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-01ri-9000000000-f0ed89dae2c22d4c538c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-053i-2900000000-3e4bf20b985893f203e72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-5419b00a9c7c126093db2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-1900000000-9a2e089c5511fa2bf2102021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-2900000000-94a6f40f937bf9d7e4c72016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9500000000-8d3540e40bfc0e4c0e5f2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-417ad1f13a593ac780b92016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-5900000000-0ed04a623daaf32fffda2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-8900000000-709928d6b823240d35282016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9600000000-4a7739132344f3dec7102016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-5671d4c535a6553aaf0d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-5671d4c535a6553aaf0d2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5e37e9f4d7b24c7633022021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-9800000000-aacb25995ab02725e0f42021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-930a2cbe3e9fb19150752021-09-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-199de8006c0d100aaabb2021-09-24View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 125 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 15.09 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID10181341
ChEMBL IDCHEMBL1044
KEGG Compound IDC07086
Pubchem Compound ID999
Pubchem Substance IDNot Available
ChEBI ID30745
Phenol-Explorer ID956
DrugBank IDNot Available
HMDB IDHMDB00209
CRC / DFC (Dictionary of Food Compounds) IDFDG02-B:FDG02-B
EAFUS ID2993
Dr. Duke IDPHENYLACETIC-ACID
BIGG ID1486426
KNApSAcK IDC00000750
HET IDPAC
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID103-82-2
GoodScent IDrw1009911
SuperScent IDNot Available
Wikipedia IDPhenylacetic_acid
Phenol-Explorer Metabolite ID956
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Metabolism and Physiological Effects of PhenylacetylglutamineSMP0123208 Not Available
Metabolism and Physiological Effects of Phenylacetic AcidSMP0123256 Not Available
Metabolsim and Physiological Effects of 4-EthylphenylsulfateSMP0125541 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
honey
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
flower
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
honeysuckle
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
sour
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
waxy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
civet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.