benzoate (PAMDB120067)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB120067
Identification
Name: benzoate
Description:The simplest member of the class of benzoates that is the conjugate base of benzoic acid, comprising a benzoic acid core with a proton missing to give a charge of -1.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Benzenecarboxylate
  • Benzeneformate
  • Benzenemethanoate
  • benzoate
  • benzoate anion
  • benzoic acid, ion(1−)
  • Phenylcarboxylate
  • Phenylformate
Chemical Formula: C7H5O2
Average Molecular Weight: 121.115
Monoisotopic Molecular Weight: 122.03678
InChI Key: WPYMKLBDIGXBTP-UHFFFAOYSA-M
InChI:InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)/p-1
CAS number: 65-85-0
IUPAC Name:benzoate
Traditional IUPAC Name: benzoic acid
SMILES:C(C1(C=CC=CC=1))([O-])=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as benzoic acids. These are organic Compounds containing a benzene ring which bears at least one carboxyl group.
Kingdom Organic compounds
Super ClassBenzenoids
Class Benzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parent Benzoic acids
Alternative Parents
Substituents
  • Benzoic acid
  • Benzoyl
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular Framework Aromatic homomonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: 122.4 °C
Experimental Properties:
PropertyValueReference
Melting Point122.4 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility3.4 mg/mL at 25 °CNot Available
LogP1.87HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility7.08 mg/mLALOGPS
logP1.72ALOGPS
logP1.63ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.31 m3·mol-1ChemAxon
Polarizability11.97 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
benzaldehyde + Water + NAD+ → benzoate + NADH + Hydrogen ion
benzaldehyde + Water + NADP+ → benzoate + NADPH + Hydrogen ion
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0a70-0900000000-5284a0c1c77a1979e1f4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-056r-3900000000-1c74c32fa650fcd4cb4dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00b9-9500000000-f312a552bef1a2927e64View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-dafd91c9134bc4143743View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00b9-9400000000-29ca905567aa5c59d46bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positivesplash10-05i0-6900000000-fa50606b2e84fc4cefe9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-0a6r-9600000000-d08dbc757a6de6c3f54eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0adi-9800000000-2693809ae064e720bf58View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0pk9-9800000000-2c6be5ecee1848091a24View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-4644ee08861e75d0b808View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00b9-9400000000-11baabb3c0bb283b1c6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004l-9100000000-4875643627420279223bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-97a21f3206f5c1f0ba7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0pk9-8900000000-3d79c70c455799ab33e3View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79. [357810 ]
  • Nathan D, Sakr A, Lichtin JL, Bronaugh RL: In vitro skin absorption and metabolism of benzoic acid, p-aminobenzoic acid, and benzocaine in the hairless guinea pig. Pharm Res. 1990 Nov;7(11):1147-51. [2293213 ]
  • Downard CD, Roberts LJ 2nd, Morrow JD: Topical benzoic acid induces the increased biosynthesis of prostaglandin D2 in human skin in vivo. Clin Pharmacol Ther. 1995 Apr;57(4):441-5. [7712673 ]
  • Temellini A, Mogavero S, Giulianotti PC, Pietrabissa A, Mosca F, Pacifici GM: Conjugation of benzoic acid with glycine in human liver and kidney: a study on the interindividual variability. Xenobiotica. 1993 Dec;23(12):1427-33. [8135043 ]
  • Dix KJ, Coleman DP, Jeffcoat AR: Comparative metabolism and disposition of gemfibrozil in male and female Sprague-Dawley rats and Syrian golden hamsters. Drug Metab Dispos. 1999 Jan;27(1):138-46. [9884323 ]
  • Parry GE, Bunge AL, Silcox GD, Pershing LK, Pershing DW: Percutaneous absorption of benzoic acid across human skin. I. In vitro experiments and mathematical modeling. Pharm Res. 1990 Mar;7(3):230-6. [2339094 ]
  • Nielsen NM, Bundgaard H: Glycolamide esters as biolabile prodrugs of carboxylic acid agents: synthesis, stability, bioconversion, and physicochemical properties. J Pharm Sci. 1988 Apr;77(4):285-98. [3379586 ]
  • Killackey JJ, Killackey BA, Philp RB: Cyclic nucleotide phosphodiesterase inhibition by a benzoic acid derivative. Agents Actions. 1985 Dec;17(2):192-6. [2420162 ]
  • Nacht S, Yeung D, Beasley JN Jr, Anjo MD, Maibach HI: Benzoyl peroxide: percutaneous penetration and metabolic disposition. J Am Acad Dermatol. 1981 Jan;4(1):31-7. [7204686 ]
  • LeBel M, Ferron L, Masson M, Pichette J, Carrier C: Benzyl alcohol metabolism and elimination in neonates. Dev Pharmacol Ther. 1988;11(6):347-56. [3229281 ]
Synthesis Reference: Hronec, Milan; Mikula, Oldrich; Kopernicky, Ivan; Bucko, Milos; Danilla, Frantisek; Hlinistak, Karol. Process for benzoic acid manufacture. Czech. (1987), 3 pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
METABOLIGHTSMTBLC16150
HMDBHMDB01870
CHEMSPIDER237
PUBCHEM242
LIGAND-CPDC00180
CHEBI16150
CAS65-85-0