Record Information
Version1.0
Creation Date2016-07-13 19:48:01 UTC
Update Date2016-07-20 20:39:18 UTC
LmdbLMDB00356
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenzoic acid
DescriptionBenzoic acid, C6H5COOH, is a colourless crystalline solid and the simplest aromatic carboxylic acid. Benzoic acid occurs naturally free and bound as benzoic acid esters in many plant and animal species. Appreciable amounts have been found in most berries (around 0.05%). Cranberries contain as much as 300-1300 mg free benzoic acid per kg fruit. Benzoic acid is a fungistatic compound that is widely used as a food preservative. It often is conjugated to glycine in the liver and excreted as hippuric acid. Benzoic acid is a byproduct of phenylalanine metabolism in bacteria. It is also produced when gut bacteria process polyphenols (from ingested fruits or beverages).
Structure
Thumb
Synonyms
ValueSource
Acide benzoiqueChEBI
Aromatic carboxylic acidChEBI
Benzenecarboxylic acidChEBI
Benzeneformic acidChEBI
Benzenemethanoic acidChEBI
BenzoesaeureChEBI
Dracylic acidChEBI
e210ChEBI
Phenylcarboxylic acidChEBI
Phenylformic acidChEBI
Aromatic carboxylateGenerator
BenzenecarboxylateGenerator
BenzeneformateGenerator
BenzenemethanoateGenerator
DracylateGenerator
PhenylcarboxylateGenerator
PhenylformateGenerator
BenzoateGenerator
Benzenemethonic acidHMDB
Benzoic acid sodium saltHMDB
CarboxybenzeneHMDB
DiacylateHMDB
Diacylic acidHMDB
Oracylic acidHMDB
Sodium benzoateHMDB
Sodium benzoic acidHMDB
Acid, benzoicHMDB
Kendall brand OF benzoic acid sodium saltHMDB
Benzoate, potassiumHMDB
Potassium benzoateHMDB
UcephanHMDB
Chemical FormulaC7H6O2
Average Molecular Weight122.123
Monoisotopic Molecular Weight122.036779433
IUPAC Namebenzoic acid
Traditional Namebenzoic acid
CAS Registry Number65-85-0
SMILES
OC(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
InChI KeyWPYMKLBDIGXBTP-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity33.31 m³·mol⁻¹ChemAxon
Polarizability11.97 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a70-0900000000-5284a0c1c77a1979e1f4Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-056r-3900000000-1c74c32fa650fcd4cb4dSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i0-6900000000-fa50606b2e84fc4cefe9Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-9600000000-d08dbc757a6de6c3f54eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0adi-9800000000-40f904bf20072c72a08bSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0pk9-9800000000-b93fc1120a1c74b88fa3Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i0-5900000000-1b6bbf98557af374f3a5Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0570-0900000000-ecd208f1e7b4d5ad85f2Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a70-0900000000-5284a0c1c77a1979e1f4Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-056r-3900000000-1c74c32fa650fcd4cb4dSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a70-0900000000-cec9e1ab69521049d1e4Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kmi-7900000000-5ad752bd6787261a11d0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-7900000000-1c4c0dbbb165ef614f43Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00b9-9500000000-f312a552bef1a2927e64Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-dafd91c9134bc4143743Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00b9-9400000000-29ca905567aa5c59d46bSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positivesplash10-05i0-6900000000-fa50606b2e84fc4cefe9Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-0a6r-9600000000-d08dbc757a6de6c3f54eSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0adi-9800000000-2693809ae064e720bf58Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0pk9-9800000000-2c6be5ecee1848091a24Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-4644ee08861e75d0b808Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00b9-9400000000-11baabb3c0bb283b1c6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004l-9100000000-4875643627420279223bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-97a21f3206f5c1f0ba7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-4644ee08861e75d0b808Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00b9-9400000000-11baabb3c0bb283b1c6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004l-9100000000-4875643627420279223bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-97a21f3206f5c1f0ba7eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00di-0900000000-94c7f13620a367bf5516Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00di-0900000000-f060e7aa8085ec6be223Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-00di-0900000000-a28fdef9c1c00d45c3ffSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-0900000000-3cad9aa6b0980c87bcc3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ee9de948bfb30da0a400Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1900000000-c18a9b04d65d91fdd99eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-9300000000-0878408a026788c942a0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3900000000-f25040451834faf3bf91Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-9500000000-b352342b60fd48a0c127Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-1d11331d7d21e32dbdbaSpectrum
MSMass Spectrum (Electron Ionization)splash10-0pk9-8900000000-3d79c70c455799ab33e3Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Feces
  • Milk
  • Plasma
  • Ruminal Fluid
  • Serum
  • Urine
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot AvailableOvine details
MilkDetected but not QuantifiedNot ApplicableNot AvailableBovine details
PlasmaDetected but not QuantifiedNot ApplicableNot AvailableOvine details
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
Ruminal FluidDetected and Quantified37 +/- 4 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified49 +/- 10 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified49 +/- 10 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified52 +/- 33 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified53 +/- 21 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified70 +/- 23 uMNot AvailableBovine
    • Saleem F, Bouatra...
details
Ruminal FluidDetected and Quantified45.9 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified52.6 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified57.4 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified72.3 uMNot AvailableBovine details
Ruminal FluidDetected and Quantified36.9 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified37.4 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified38.2 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
Ruminal FluidDetected and Quantified53.9 uMNot AvailableBovine
    • Burim NA, Qendrim...
details
SerumDetected and Quantified0.00766 +/- 0.000172 uMNot AvailablePorcine details
SerumDetected and Quantified0.00844 +/- 0.000221 uMNot AvailablePorcine details
UrineDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDDB03793
HMDB IDHMDB0001870
FooDB IDFDB008739
Phenol Explorer ID427
KNApSAcK IDC00000207
BiGG ID34156
BioCyc IDBENZOATE
METLIN ID1297
PDB IDNot Available
Wikipedia LinkBenzoic_Acid
Chemspider ID238
ChEBI ID30746
PubChem Compound ID243
Kegg Compound IDC00539
YMDB IDYMDB02301
ECMDB IDECMDB04023
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available