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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-06-10 21:23:02 UTC
HMDB IDHMDB00209
Secondary Accession Numbers
  • 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). 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-Phenylethanoic acidChEBI
alpha-Toluic acidChEBI
Benzeneacetic acidChEBI
Benzylformic acidChEBI
Omega-phenylacetic acidChEBI
PAChEBI
2-PhenylethanoateGenerator
2-PhenylacetateGenerator
a-ToluateGenerator
a-Toluic acidGenerator
alpha-ToluateGenerator
α-toluateGenerator
α-toluic acidGenerator
BenzeneacetateGenerator
BenzylformateGenerator
Omega-phenylacetateGenerator
PhenylacetateHMDB
PhenylethanoateHMDB
Phenylethanoic acidHMDB
W-PhenylacetateHMDB
W-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 KeyInChIKey=WLJVXDMOQOGPHL-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylacetic acid derivatives
Direct ParentPhenylacetic acid derivatives
Alternative Parents
Substituents
  • Phenylacetate
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity37.37 m3·mol-1ChemAxon
Polarizability13.85 Å3ChemAxon
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
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0006-9100000000-de65c7c0092343a4e599View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0006-9100000000-1e23fd8e6ce900cd8e4cView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Phenylacetate MetabolismSMP00126map00360
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 QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956
  • Not Applicable
details
BloodDetected and Quantified<10.28 uMAdult (>18 years old)BothNormal details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956
  • Not Applicable
details
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956
  • Not Applicable
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 QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>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 QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
SalivaDetected and Quantified47.04 +/- 31.31 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
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 QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 956
  • Not Applicable
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 QuantifiedNot ApplicableAdult (>18 years old)BothLeukemia details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Ulcerative colitis
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Colorectal 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. [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. [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
NuGOwiki LinkHMDB00209
Metagene LinkHMDB00209
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. [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. [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. [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. [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. [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. [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. [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. [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 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