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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-12-21 14:22:10 UTC
Update Date2019-07-23 05:45:06 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-). An alternative synthesis involves hydrolysis of benzoyl cyanide. Phenylglyoxylic acid is a drug. Phenylglyoxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Phenylglyoxylic acid is the organic compound with the formula C6H5C(O)CO2H. Phenylglyoxylic acid exists in all living organisms, ranging from bacteria to humans. Phenylglyoxylic acid can be synthesized by oxidation of mandelic acid with potassium permanganate. The conjugate base, known as benzoylformate is the substrate of benzoylformate decarboxylase, a thiamine diphosphate-dependent enzyme:benzoylformate + H+ ⇌ benzaldehyde + CO2It is a colourless solid, m.p. 64–66 °C with a moderate acidity,which pKa2.15.
Structure
Data?1563860706
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1590000000-8979a0bb117ef1b0a5efJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-6910000000-9b94bfa8c5a5d0d50391JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-7920000000-92b45b4e19d67c7831b6JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-1590000000-8979a0bb117ef1b0a5efJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-6910000000-9b94bfa8c5a5d0d50391JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-7920000000-92b45b4e19d67c7831b6JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-9800000000-0aa7221d97a613853d27JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-3900000000-0da1d073cf227a6edb2dJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0zfr-1900000000-15499c77fbdf6aba2c6fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9300000000-c84b000626073ef1eb7eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9100000000-0d840af6ff6db1d61038JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-22fd9c3f15b7011e1779JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-004i-9000000000-eb5833f7b7cb1312e0fbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004i-9000000000-518533199e7a59cb1b17JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-004i-9000000000-a7f64053378dba21530cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-77eed9b73d7a3aa5b334JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-0900000000-22fd9c3f15b7011e1779JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-6404f2ea0445ac6823c2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-518533199e7a59cb1b17JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-a7f64053378dba21530cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004i-9000000000-77eed9b73d7a3aa5b334JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0zfr-0900000000-bfd6a85aa1dd9b7b1825JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-26ddf52958908dab7e61JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-4900000000-1c5be9fdb7b12285bd78JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-052b-0900000000-a1aa81158b89b94eafa2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-0900000000-4ade370b08e99fee6f56JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0pb9-2900000000-37feae0472ecc66b90f3JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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 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
FoodDB 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
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 ]