You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-12-21 14:22:10 UTC
Update Date2020-02-26 23:55:04 UTC
HMDB IDHMDB0001587
Secondary Accession Numbers
  • HMDB01587
Metabolite Identification
Common NamePhenylglyoxylic acid
DescriptionPhenylglyoxylic acid, also known as benzoylformate or 2-oxo-2-phenylacetate, 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-). Phenylglyoxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylglyoxylic acid exists in all living organisms, ranging from bacteria to humans.
Structure
Data?1582752211
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 acidHMDB
Phenylglyoxylic acid, calcium saltHMDB
Phenylglyoxylic acid, potassium saltHMDB
Phenylglyoxylic acid, sodium saltHMDB
Phenylglyoxylic hydrochlorideHMDB
Phenylglyoxylic acidKEGG
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
Description 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:

Source:

Role

Industrial application:

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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1590000000-8979a0bb117ef1b0a5efSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-6910000000-9b94bfa8c5a5d0d50391Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-7920000000-92b45b4e19d67c7831b6Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1590000000-8979a0bb117ef1b0a5efSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-6910000000-9b94bfa8c5a5d0d50391Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-7920000000-92b45b4e19d67c7831b6Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9800000000-0aa7221d97a613853d27Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-3900000000-0da1d073cf227a6edb2dSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0zfr-1900000000-15499c77fbdf6aba2c6fSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9300000000-c84b000626073ef1eb7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-0d840af6ff6db1d61038Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-22fd9c3f15b7011e1779Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-eb5833f7b7cb1312e0fbSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-518533199e7a59cb1b17Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a7f64053378dba21530cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-77eed9b73d7a3aa5b334Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-22fd9c3f15b7011e1779Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-6404f2ea0445ac6823c2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-518533199e7a59cb1b17Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a7f64053378dba21530cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-77eed9b73d7a3aa5b334Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0900000000-bfd6a85aa1dd9b7b1825Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-26ddf52958908dab7e61Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-1c5be9fdb7b12285bd78Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0900000000-a1aa81158b89b94eafa2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0900000000-4ade370b08e99fee6f56Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-2900000000-37feae0472ecc66b90f3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified36.6 +/- 0.48 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.019 (0.015-0.024) umol/mmol creatinineNewborn (0-30 days old)BothNormal details
UrineDetected and Quantified7.34 umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
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 IDDB02279
Phenol Explorer Compound IDNot Available
FooDB IDFDB022696
KNApSAcK IDNot Available
Chemspider ID11421
KEGG Compound IDC02137
BioCyc IDPHENYLGLYOXYLATE
BiGG IDNot Available
Wikipedia LinkPhenylglyoxylic_acid
METLIN IDNot Available
PubChem Compound11915
PDB IDNot Available
ChEBI ID18280
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 ]