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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:13:09 UTC
HMDB IDHMDB0000209
Secondary Accession Numbers
  • HMDB00209
  • HMDB01326
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), 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
2-PHENYLACETateGenerator
PhenylacetateGenerator
2-PhenylethanoateGenerator
a-ToluateGenerator
a-Toluic acidGenerator
alpha-ToluateGenerator
α-toluateGenerator
α-toluic acidGenerator
BenzeneacetateGenerator
BenzylformateGenerator
Omega-phenylacetateGenerator
PhenylethanoateHMDB
Phenylethanoic acidHMDB
W-PhenylacetateHMDB
W-Phenylacetic acidHMDB
Phenylacetic acid, potassium saltMeSH
Sodium phenylacetateMeSH
Phenylacetic acid, lithium saltMeSH
Phenylacetic acid, sodium saltMeSH
Phenylacetic acid, ammonium saltMeSH
Phenylacetic acid, calcium saltMeSH
Phenylacetic acid, cesium saltMeSH
Phenylacetic acid, mercury saltMeSH
Phenylacetic acid, rubidium saltMeSH
Phenylacetic acid, sodium salt , carboxy-(11)C-labeled CPDMeSH
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
DescriptionThis compound 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
Physiological effect

Health effect:

  Health condition:

    Gastrointestinal disorders:

    Psychiatric disorders:

    Renal and urinary disorders:

    Nervous system disorders:

  Observation:

    Investigations:

Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Biofluid and excreta:

Source:

Route of exposure:

  Parenteral:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point76.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility16.6 mg/mLNot Available
LogP1.41HANSCH,C ET AL. (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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
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
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
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
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Phenylacetate MetabolismPw000033Pw000033 greyscalePw000033 simpleMap00360
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified47.24 +/- 5.866 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified58.864 +/- 3.78 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified50.34 +/- 4.973 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified53.443 +/- 6.56 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified48.507 +/- 3.763 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified49.663 +/- 3.885 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified51.556 +/- 6.132 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified80.36 +/- 24.113 uMAdult (>18 years old)Male
Normal
details
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956 details
    BloodDetected and Quantified<10.28 uMAdult (>18 years old)BothNormal details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956 details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956 details
    BloodExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956 details
    Cerebrospinal Fluid (CSF)Detected and Quantified0.148 +/- 0.0198 uMAdult (>18 years old)Not SpecifiedNormal details
    Cerebrospinal Fluid (CSF)Detected and Quantified0.248 +/- 0.0294 uMNot SpecifiedNot SpecifiedNormal details
    Cerebrospinal Fluid (CSF)Detected and Quantified0.306 uMNot SpecifiedNot SpecifiedNormal details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)BothNormal details
    FecesDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified1182.538 +/- 1035.638 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified1344.126 +/- 1226.607 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified498.722 +/- 287.922 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified689.691 +/- 438.494 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Infant (0-1 year old)Not AvailableNormal details
    FecesDetected but not Quantified Not SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified878.0157 +/- 425.714 uMNot SpecifiedNot Specified
    Normal
    details
    FecesDetected and Quantified1115.698 +/- 659.577 uMNot SpecifiedNot Specified
    Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected but not Quantified Infant (0-1 year old)Not Specified
    Normal
    details
    FecesDetected but not Quantified Infant (0-1 year old)Not Specified
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected but not Quantified Adult (>18 years old)Male
    Normal
    details
    SalivaDetected and Quantified47.04 +/- 31.31 uMAdult (>18 years old)BothNormal
      • Zerihun T. Dame, ...
    details
    UrineDetected and Quantified0.000000079 (0-0.00000095) umol/mmol creatinineInfant (0-1 year old)Not SpecifiedNormal details
    UrineDetected and Quantified8.994 +/- 5.642 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified0.25-0.46 umol/mmol creatinineAdult (>18 years old)FemaleNormal details
    UrineDetected and Quantified4.16 +/- 0.91 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified<2.16 umol/mmol creatinineChildren (1 - 18 years old)Both
    Normal
      • BC Children's Hos...
    details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956 details
    UrineExpected but not Quantified Not AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956 details
    UrineDetected and Quantified0.20-0.41 umol/mmol creatinineAdult (>18 years old)MaleNormal details
    UrineDetected and Quantified0.3 umol/mmol creatinineAdult (>18 years old)BothNormal details
    UrineDetected and Quantified1.9 umol/mmol creatinineAdult (>18 years old)BothNormal details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    BloodDetected and Quantified3490.0 +/- 330.0 uMAdult (>18 years old)Not Specified
    Kidney disease
    details
    BloodDetected and Quantified3485.92 +/- 329.79 uMAdult (>18 years old)Bothuremia details
    BloodDetected but not Quantified Adult (>18 years old)BothLeukemia details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Campylobacter jejuni infection
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Irritable bowel syndrome
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Ulcerative colitis
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Colorectal cancer
    details
    FecesDetected but not Quantified Adult (>18 years old)BothColorectal cancer details
    UrineDetected and Quantified55.6 +/- 87.3 umol/mmol creatinineInfant (0-1 year old)BothPhenylketonuria details
    UrineDetected and Quantified16.505 +/- 12.758 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Eosinophilic esophagitis
      • Mordechai, Hien, ...
    details
    UrineDetected and Quantified55.00 +/- 87.00 umol/mmol creatinineNewborn (0-30 days old)BothPhenylketonuria details
    Associated Disorders and Diseases
    Disease References
    Kidney disease
    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 ]
    Phenylketonuria
    1. Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ]
    Associated OMIM IDs
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite ID956
    FoodDB IDFDB010558
    KNApSAcK IDC00000750
    Chemspider ID10181341
    KEGG Compound IDC07086
    BioCyc IDPHENYLACETATE
    BiGG ID1486426
    Wikipedia LinkPhenylacetic_acid
    METLIN ID129
    PubChem Compound999
    PDB IDPAC
    ChEBI ID30745
    References
    Synthesis ReferenceZhou, 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)
    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 ]

    Enzymes

    General function:
    Involved in oxidoreductase activity
    Specific function:
    ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
    Gene Name:
    ALDH3A1
    Uniprot ID:
    P30838
    Molecular weight:
    50394.57
    Reactions
    Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
    Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
    Gene Name:
    ALDH1A3
    Uniprot ID:
    P47895
    Molecular weight:
    56107.995
    Reactions
    Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
    Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails
    General function:
    Involved in transferase activity, transferring hexosyl groups
    Specific function:
    UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
    Gene Name:
    UGT1A1
    Uniprot ID:
    P22309
    Molecular weight:
    59590.91
    Reactions
    Phenylacetic acid → 3,4,5-trihydroxy-6-[(2-phenylacetyl)oxy]oxane-2-carboxylic aciddetails
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Not Available
    Gene Name:
    ALDH3B2
    Uniprot ID:
    P48448
    Molecular weight:
    42623.62
    Reactions
    Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
    Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
    Gene Name:
    ALDH3B1
    Uniprot ID:
    P43353
    Molecular weight:
    51839.245
    Reactions
    Phenylacetaldehyde + NAD + Water → Phenylacetic acid + NADH + Hydrogen Iondetails
    Phenylacetaldehyde + NADP + Water → Phenylacetic acid + NADPH + Hydrogen Iondetails