Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120149
Identification
Name: phenylglyoxylate
Description:A member of the class of glyoxylates, that is obtained by removal of a proton from the carboxylic acid group of phenylglyoxylic acid.
Structure
Thumb
Synonyms:
  • benzoylformic acid anion
  • phenylglyoxylate
  • phenylglyoxylic acid anion
Chemical Formula: C8H5O3
Average Molecular Weight: 149.126
Monoisotopic Molecular Weight: 150.0317
InChI Key: FAQJJMHZNSSFSM-UHFFFAOYSA-M
InChI:InChI=1S/C8H6O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5H,(H,10,11)/p-1
CAS number: 611-73-4
IUPAC Name:oxo(phenyl)acetate
Traditional IUPAC Name: benzoylformic acid
SMILES:C(=O)(C(C1(C=CC=CC=1))=O)[O-]
Chemical Taxonomy
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-).
Kingdom Organic compounds
Super ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassBenzoyl derivatives
Direct Parent Benzoyl 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 Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 66 °C
Experimental Properties:
PropertyValueReference
Melting Point66 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility920.0 mg/mL at 0 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.42 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.26 m3·mol-1ChemAxon
Polarizability14.07 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
References
References:
  • 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. [3782394 ]
  • 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. [2739101 ]
Synthesis Reference: Hurd, 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)
External Links:
ResourceLink
HMDBHMDB01587
CHEMSPIDER1265921
CHEBI36656
PUBCHEM1548898
LIGAND-CPDC02137
CAS611-73-4