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Benzeneacetic acid (M2MDB000625)

Record Information
Version2.0
Creation Date2012-05-31 14:05:52 -0600
Update Date2015-09-13 12:56:14 -0600
Secondary Accession Numbers
  • ECMDB04128
Identification
Name:Benzeneacetic acid
DescriptionBenzeneacetic acid or phenylacetate is produced by a number of microorganisms including E. coli via the aerobic metabolism of phenylalanine (via oxidation). Phenylacetate is then converted into phenylacetyl-CoA where it is processed into a variety of other compounds mediated by the paa operon (PMID:12846838). Phenylacetate is also produced by a number of plants and is used as a perfumery and flavoring ingredient. It has a sweet taste at low concentrations and has a rose-like odor. It can also be used as a phytotoxin or seed germination inhibitor (Dictionary of Organic Compounds)
Structure
Thumb
MOLSDFPDBSMILESInChI
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
  • α-Toluate
  • α-Toluic acid
Chemical Formula:C8H8O2
Weight:Average: 136.1479
Monoisotopic: 136.0524295
InChI Key:WLJVXDMOQOGPHL-UHFFFAOYSA-N
InChI:InChI=1S/C8H8O2/c9-8(10)6-7-4-2-1-3-5-7/h1-5H,6H2,(H,9,10)
CAS number:103-82-2
IUPAC Name:2-phenylacetic acid
Traditional IUPAC Name:ω-phenylacetic acid
SMILES:OC(=O)CC1=CC=CC=C1
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
State:Solid
Charge:-1
Melting point:76.7 °C
Experimental Properties:
PropertyValueSource
Water Solubility:16.6 mg/mL [CHIOU,CT et al. (1977)]PhysProp
LogP:1.41 [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
Reactions:
Water + NAD + Phenylacetaldehyde <>2 Hydrogen ion + NADH + Benzeneacetic acid
Adenosine triphosphate + Coenzyme A + Benzeneacetic acid <> Adenosine monophosphate + Phenylacetyl-CoA + Pyrophosphate
Phenylacetaldehyde + NAD + Water <> Benzeneacetic acid + NADH + Hydrogen ion
Phenylacetyl-CoA + Water <> Benzeneacetic acid + Coenzyme A
Phenylacetaldehyde + NAD + Water > Benzeneacetic acid + NADH
Adenosine triphosphate + Benzeneacetic acid + CoA > Adenosine monophosphate + Pyrophosphate + Phenylacetyl-CoA
Phenylacetaldehyde + NAD + Water > NADH + Hydrogen ion + Benzeneacetic acid
Benzeneacetic acid + Adenosine triphosphate + Coenzyme A > Adenosine monophosphate + Pyrophosphate + Phenylacetyl-CoA
SMPDB Pathways:
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylethylamine metabolismPW002027 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-0006-9700000000-c07461cdad68959aa53fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9100000000-de65c7c0092343a4e599View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0006-9700000000-c07461cdad68959aa53fView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-9700000000-43e86e45beae2fa6704fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9200000000-dc43e5e062b0ed500c5fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9100000000-aaef76d181aebe492bbeView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9100000000-de65c7c0092343a4e599View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-0006-9000000000-6ca33b098558bf13801cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-000i-0900000000-f898aafe4cecc87d26f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0006-9400000000-aa5bff1d7a8df7c97bdbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-6a017c8136a375269f3eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-2900000000-d79f9224f2390d6b17a2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-e712b088c9a3d3855ec7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-01ri-9000000000-f0ed89dae2c22d4c538cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-053i-2900000000-3e4bf20b985893f203e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-000i-1900000000-5419b00a9c7c126093dbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-1900000000-9a2e089c5511fa2bf210View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-2900000000-94a6f40f937bf9d7e4c7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9500000000-8d3540e40bfc0e4c0e5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-417ad1f13a593ac780b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000l-5900000000-0ed04a623daaf32fffdaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-8900000000-709928d6b823240d3528View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9600000000-4a7739132344f3dec710View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-9000000000-5671d4c535a6553aaf0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9000000000-5671d4c535a6553aaf0dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5e37e9f4d7b24c763302View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-9800000000-aacb25995ab02725e0f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-9100000000-930a2cbe3e9fb1915075View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9000000000-199de8006c0d100aaabbView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-1e23fd8e6ce900cd8e4cView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
References
References:
  • 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
  • Ismail, W., El-Said Mohamed, M., Wanner, B. L., Datsenko, K. A., Eisenreich, W., Rohdich, F., Bacher, A., Fuchs, G. (2003). "Functional genomics by NMR spectroscopy. Phenylacetate catabolism in Escherichia coli." Eur J Biochem 270:3047-3054. Pubmed: 12846838
  • 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
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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.
Material Safety Data Sheet (MSDS)Download (PDF)
External Links:
ResourceLink
CHEBI ID18401
HMDB IDHMDB00209
Pubchem Compound ID999
Kegg IDC07086
ChemSpider ID10181341
WikipediaPhenylacetic_acid
BioCyc IDNot Available
Ligand ExpoPAC

Enzymes

Protein Details
1. Phenylacetate-coenzyme A ligase
General function:
Involved in catalytic activity
Specific function:
Catalyzes the activation of phenylacetic acid to phenylacetyl-CoA
Gene Name:
paaK
Uniprot ID:
P76085
Molecular weight:
48953
Reactions
ATP + phenylacetate + CoA = AMP + diphosphate + phenylacetyl-CoA.
Protein Details
2. Phenylacetaldehyde dehydrogenase
General function:
Involved in oxidoreductase activity
Specific function:
Acts almost equally well on phenylacetaldehyde, 4- hydroxyphenylacetaldehyde and 3,4-dihydroxyphenylacetaldehyde
Gene Name:
feaB
Uniprot ID:
P80668
Molecular weight:
53699
Reactions
Phenylacetaldehyde + NAD(+) + H(2)O = phenylacetate + NADH.
Protein Details
3. thioesterase, most active with ring-hydroxylated phenylacetyl-coenzyme A thioesters
General function:
Not Available
Specific function:
Not Available
Gene Name:
paaI
Uniprot ID:
P76084
Molecular weight:
Not Available