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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-02-06 00:12:21 UTC
NP-MRD IDNP0000651
Secondary Accession NumbersNone
Natural Product 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), an inborn error of metabolism. 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
2-PhenylethanoateGenerator
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
PAAHMDB
Ω-phenylacetic acidHMDB
Phenylethanoic acidHMDB
Chemical FormulaC8H8O2
Average Mass136.1479 Da
Monoisotopic Mass136.05243 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, simulated)Varshavi.d262021-08-02View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-06View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-02-06View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Anthyllis henonianaLOTUS Database
Anthyllis subsimplexKNApSAcK Database
Artemisia judaicaLOTUS Database
Bacillus marinusLOTUS Database
Bellis perennisLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Calyx podatypaLOTUS Database
Capra aegagrus hircusFooDB
Carya ovataLOTUS Database
CervidaeFooDB
Cervus canadensisFooDB
Colletotrichum gloeosporioidesLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Duboisia leichhardtiiLOTUS Database
Equus caballusFooDB
Gallus gallusFooDB
Gryllotalpa orientalisLOTUS Database
Houttuynia cordataKNApSAcK Database
Jacaranda glabraLOTUS Database
Juglans nigra L.FooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Litsea cubebaKNApSAcK Database
Lupinus angustifoliusLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mentha x piperitaFooDB
Mus musculusLOTUS Database
Nicotiana tabacumLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Osmorhiza aristataLOTUS Database
Ovis ariesFooDB
Pelargonium graveolensLOTUS Database
Peltostigma guatemalenseLOTUS Database
Penicillium herqueiLOTUS Database
Penicillium oxalicumLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Piper nigrumLOTUS Database
Piper nigrum L.FooDB
Pisum sativumKNApSAcK Database
Plumeria rubraLOTUS Database
Pogonomyrmex rugosusLOTUS Database
Prunus dulcisFooDB
Rehmannia glutinosaKNApSAcK Database
Saussurea superbaLOTUS Database
Streptomyces humidusLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Theobroma cacaoFooDB
Triticum aestivumKNApSAcK Database
Tropaeolum majusLOTUS Database
Trypanosoma bruceiLOTUS Database
Undaria pinnatifidaLOTUS Database
Vitis viniferaLOTUS Database
Zea maysLOTUS Database
Zea mays L.FooDB
Species Where Detected
Species NameSourceReference
Biscogniauxia mediterraneaKNApSAcK Database
Escherichia coliKNApSAcK Database
Homo sapiens (Urine)KNApSAcK Database
Pseudomonas pseudoalcaligenesKNApSAcK Database
Streptomyces humidus S5-55KNApSAcK Database
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 Point265.00 to 266.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility16.6 mg/mLNot Available
LogP1.41Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
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
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
Good Scents IDrw1009911
References
General References
  1. Jankowski J, van der Giet M, Jankowski V, Schmidt S, Hemeier M, Mahn B, Giebing G, Tolle M, Luftmann H, Schluter H, Zidek W, Tepel M: Increased plasma phenylacetic acid in patients with end-stage renal failure inhibits iNOS expression. J Clin Invest. 2003 Jul;112(2):256-64. [PubMed:12865413 ]
  2. Pontoni G, Rotondo F, Spagnuolo G, Aurino MT, Carteni-Farina M, Zappia V, Lama G: Diagnosis and follow-up of cystinuria: use of proton magnetic resonance spectroscopy. Amino Acids. 2000;19(2):469-76. [PubMed:11128553 ]
  3. Rubin A, Knadler MP, Ho PP, Bechtol LD, Wolen RL: Stereoselective inversion of (R)-fenoprofen to (S)-fenoprofen in humans. J Pharm Sci. 1985 Jan;74(1):82-4. [PubMed:3920382 ]
  4. Davis BA, Kennedy SH, D'Souza J, Durden DA, Goldbloom DS, Boulton AA: Correlations of plasma and urinary phenylacetic acid and phenylethylamine concentrations with eating behavior and mood rating scores in brofaromine-treated women with bulimia nervosa. J Psychiatry Neurosci. 1994 Jul;19(4):282-8. [PubMed:7918350 ]
  5. Silvennoinen R, Malminiemi K, Malminiemi O, Seppala E, Vilpo J: Pharmacokinetics of chlorambucil in patients with chronic lymphocytic leukaemia: comparison of different days, cycles and doses. Pharmacol Toxicol. 2000 Nov;87(5):223-8. [PubMed:11129502 ]
  6. 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. [PubMed:17978765 ]
  7. 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. [PubMed:476920 ]
  8. 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. [PubMed:6857245 ]
  9. Ju Z, Shao J, Zhou M, Jin J, Pan H, Ding P, Huang R: Transcriptomic and metabolomic profiling reveal the p53-dependent benzeneacetic acid attenuation of silica-induced epithelial-mesenchymal transition in human bronchial epithelial cells. Cell Biosci. 2021 Feb 5;11(1):30. doi: 10.1186/s13578-021-00545-0. [PubMed:33546743 ]