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Record Information
Version4.0
Creation Date2005-12-21 14:22:10 UTC
Update Date2017-09-27 08:24:08 UTC
HMDB IDHMDB0001587
Secondary Accession Numbers
  • HMDB01587
Metabolite Identification
Common NamePhenylglyoxylic acid
DescriptionPhenylglyoxylic acid is one of the major urinary metabolites of toluene, o-, m- and p-xylenes, styrene and ethylbenzene. (PMID 3782394 ). For the biological monitoring of workers exposure to solvent used in industry, its concentration is measured in human urine samples. (PMID 2739101 ).
Structure
Thumb
Synonyms
ValueSource
2-oxo-2-PhenylacetateChEBI
2-oxo-2-Phenylacetic acidChEBI
2-Phenylethanoic acidChEBI
alpha-Ketophenylacetic acidChEBI
alpha-oxo-Benzeneacetic acidChEBI
Benzeneglyoxylic acidChEBI
BENZOYL-formIC ACIDChEBI
BenzoylformateChEBI
Benzoylformic acidChEBI
PhenylglyoxylateChEBI
2-PhenylethanoateGenerator
a-KetophenylacetateGenerator
a-Ketophenylacetic acidGenerator
alpha-KetophenylacetateGenerator
α-ketophenylacetateGenerator
α-ketophenylacetic acidGenerator
a-oxo-BenzeneacetateGenerator
a-oxo-Benzeneacetic acidGenerator
alpha-oxo-BenzeneacetateGenerator
α-oxo-benzeneacetateGenerator
α-oxo-benzeneacetic acidGenerator
BenzeneglyoxylateGenerator
BENZOYL-formateGenerator
a-Oxobenzeneacetic acidHMDB
alpha-Oxobenzeneacetic acidHMDB
Oxophenylacetic acidHMDB
Phenylgloxylic acidHMDB
Phenyloxoacetic acidHMDB
Phenylglyoxilic acidMeSH
Phenylglyoxylic acid, calcium saltMeSH
Phenylglyoxylic acid, potassium saltMeSH
Phenylglyoxylic acid, sodium saltMeSH
Phenylglyoxylic hydrochlorideMeSH
Chemical FormulaC8H6O3
Average Molecular Weight150.1314
Monoisotopic Molecular Weight150.031694058
IUPAC Name2-oxo-2-phenylacetic acid
Traditional Namebenzoylformic acid
CAS Registry Number611-73-4
SMILES
OC(=O)C(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)
InChI KeyFAQJJMHZNSSFSM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoyl derivatives. These are organic compounds containing an acyl moiety of benzoic acid with the formula (C6H5CO-).
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoyl derivatives
Direct ParentBenzoyl derivatives
Alternative Parents
Substituents
  • Aryl ketone
  • Benzoyl
  • Keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • 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
Disposition

Biological Location:

  Biofluid and excreta:

Source:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point66 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility920 mg/mL at 0 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.42 g/LALOGPS
logP1.16ALOGPS
logP1.49ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.69ChemAxon
pKa (Strongest Basic)-9.5ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.26 m³·mol⁻¹ChemAxon
Polarizability14.07 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-EI-TOFsplash10-00di-1590000000-8979a0bb117ef1b0a5efView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0f79-6910000000-9b94bfa8c5a5d0d50391View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0f79-7920000000-92b45b4e19d67c7831b6View 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 (1 TMS) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0zfr-1900000000-15499c77fbdf6aba2c6fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9300000000-c84b000626073ef1eb7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-0d840af6ff6db1d61038View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-22fd9c3f15b7011e1779View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-eb5833f7b7cb1312e0fbView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-518533199e7a59cb1b17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a7f64053378dba21530cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-77eed9b73d7a3aa5b334View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-22fd9c3f15b7011e1779View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-6404f2ea0445ac6823c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-518533199e7a59cb1b17View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a7f64053378dba21530cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-77eed9b73d7a3aa5b334View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0900000000-bfd6a85aa1dd9b7b1825View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-26ddf52958908dab7e61View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-1c5be9fdb7b12285bd78View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0900000000-a1aa81158b89b94eafa2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0900000000-4ade370b08e99fee6f56View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-2900000000-37feae0472ecc66b90f3View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified36.6 +/- 0.48 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified7.34 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified62.9 +/- 1.18 umol/mmol creatinineAdult (>18 years old)BothOccupational exposure to styrene details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022696
KNApSAcK IDNot Available
Chemspider ID11421
KEGG Compound IDC02137
BioCyc IDCPD-141
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound11915
PDB ID173
ChEBI ID18280
References
Synthesis ReferenceHurd, Charles D.; McNamee, R. W.; Green, Frank O. Benzoylformic acid from styrene. Journal of the American Chemical Society (1939), 61 2979-80.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Lacroix C, Inger F, Menager S, Lafont O: [Simultaneous determination of urinary hippuric acid and o-, m-, p-methylhippuric acids with liquid chromatography]. J Chromatogr. 1986 Oct 31;382:275-9. [PubMed:3782394 ]
  2. Sakai T, Takeuchi Y, Ikeya Y, Araki T, Ushio K: [Method for simultaneous determination of six metabolites of toluene, xylene and ethylbenzene, and its application to exposure monitoring of workers in a printing factory with gravure machines]. Sangyo Igaku. 1989 Jan;31(1):9-16. [PubMed:2739101 ]