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Identification
YMDB IDYMDB02301
NameBenzoic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
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. 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
  • Benzenecarboxylic acid
  • Benzeneformate
  • Benzeneformic acid
  • Benzenemethanoate
  • Benzenemethanoic acid
  • Benzenemethonic acid
  • Benzoate
  • benzoic acid
  • Benzoic acid sodium salt
  • Carboxybenzene
  • Diacylate
  • Diacylic acid
  • Dracylate
  • Dracylic acid
  • Oracylic acid
  • Phenylcarboxylate
  • Phenylcarboxylic acid
  • Phenylformate
  • Phenylformic acid
  • Sodium benzoate
  • Sodium benzoic acid
  • Benzenecarboxylate
  • Acide benzoique
  • Aromatic carboxylic acid
  • Benzenecarboxylic acid
  • Benzeneformic acid
  • Benzenemethanoic acid
  • Benzoesaeure
  • Dracylic acid
  • e210
  • Phenylcarboxylic acid
  • Phenylformic acid
  • Aromatic carboxylate
  • Benzeneformate
  • Benzenemethanoate
  • Dracylate
  • Phenylcarboxylate
  • Phenylformate
  • Benzoate
  • Benzenemethonic acid
  • Benzoic acid sodium salt
  • Carboxybenzene
  • Diacylate
  • Diacylic acid
  • Oracylic acid
  • Sodium benzoate
  • Sodium benzoic acid
  • Acid, benzoic
  • Kendall brand OF benzoic acid sodium salt
  • Benzoate, potassium
  • Potassium benzoate
  • Ucephan
CAS number65-85-0
WeightAverage: 122.1213
Monoisotopic: 122.036779436
InChI KeyWPYMKLBDIGXBTP-UHFFFAOYSA-N
InChIInChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
IUPAC Namebenzoic acid
Traditional IUPAC Namebenzoic acid
Chemical FormulaC7H6O2
SMILESOC(=O)C1=CC=CC=C1
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
Physical Properties
StateSolid
Charge0
Melting point122.4 °C
Experimental Properties
PropertyValueReference
Water Solubility3.4 mg/mL at 25 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP1.87 [HANSCH,C ET AL. (1995)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility7.08 g/LALOGPS
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic Properties
Flavour/OdourSource
BalsamFDB008739
FaintFDB008739
UrineFDB008739
SMPDB PathwaysNot Available
KEGG PathwaysNot Available
SMPDB ReactionsNot Available
KEGG ReactionsNot Available
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a70-0900000000-5284a0c1c77a1979e1f4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-056r-3900000000-1c74c32fa650fcd4cb4dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i0-6900000000-fa50606b2e84fc4cefe9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-9600000000-d08dbc757a6de6c3f54eJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0adi-9800000000-40f904bf20072c72a08bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0pk9-9800000000-b93fc1120a1c74b88fa3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i0-5900000000-1b6bbf98557af374f3a5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0570-0900000000-ecd208f1e7b4d5ad85f2JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a70-0900000000-5284a0c1c77a1979e1f4JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-056r-3900000000-1c74c32fa650fcd4cb4dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a70-0900000000-cec9e1ab69521049d1e4JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kmi-7900000000-5ad752bd6787261a11d0JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-7900000000-1c4c0dbbb165ef614f43JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00b9-9500000000-f312a552bef1a2927e64JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-dafd91c9134bc4143743JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00b9-9400000000-29ca905567aa5c59d46bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positivesplash10-05i0-6900000000-fa50606b2e84fc4cefe9JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-0a6r-9600000000-d08dbc757a6de6c3f54eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0adi-9800000000-2693809ae064e720bf58JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0pk9-9800000000-2c6be5ecee1848091a24JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-4644ee08861e75d0b808JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00b9-9400000000-11baabb3c0bb283b1c6eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004l-9100000000-4875643627420279223bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-97a21f3206f5c1f0ba7eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-4644ee08861e75d0b808JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00b9-9400000000-11baabb3c0bb283b1c6eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004l-9100000000-4875643627420279223bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-97a21f3206f5c1f0ba7eJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ee9de948bfb30da0a400JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1900000000-c18a9b04d65d91fdd99eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-9300000000-0878408a026788c942a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3900000000-f25040451834faf3bf91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-9500000000-b352342b60fd48a0c127JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-1d11331d7d21e32dbdbaJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0pk9-8900000000-3d79c70c455799ab33e3JSpectraViewer | MoNA
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Hronec, Milan; Mikula, Oldrich; Kopernicky, Ivan; Bucko, Milos; Danilla, Frantisek; Hlinistak, Karol. Process for benzoic acid manufacture. Czech. (1987), 3 pp.
External Links:
ResourceLink
CHEBI ID30746
HMDB IDHMDB01870
Pubchem Compound ID243
Kegg IDC00180
ChemSpider ID238
FOODB IDFDB008739
Wikipedia IDBenzoic_Acid
BioCyc IDNot Available