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Benzoic acid (CHEM003742)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2014-09-11 05:16:29 UTC
Update Date2016-10-28 10:04:28 UTC
Accession NumberCHEM003742
Identification
Common NameBenzoic acid
ClassSmall Molecule
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).
Contaminant Sources
  • Clean Air Act Chemicals
  • Cosmetic Chemicals
  • EAFUS Chemicals
  • FooDB Chemicals
  • HMDB Contaminants - Feces
  • HMDB Contaminants - Urine
  • HPV EPA Chemicals
  • OECD HPV Chemicals
  • STOFF IDENT Compounds
  • Suspected Compounds – Schymanski Project
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Animal Toxin
  • Ester
  • Food Preservative
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Preservative
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
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 Mass122.123 g/mol
Monoisotopic Mass122.037 g/mol
CAS Registry Number65-85-0
IUPAC Namebenzoic acid
Traditional Namebenzoic acid
SMILESOC(=O)C1=CC=CC=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Cytoplasm
  • Endoplasmic reticulum
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Bladder
  • Fibroblasts
  • Kidney
  • Liver
  • Skin
  • Stratum Corneum
  • Testes
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point122.4°C
Boiling Point249.2°C
Solubility3400 mg/L (at 25°C)
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
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-MSsplash10-0kmi-7900000000-5ad752bd6787261a11d0View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-05i0-6900000000-fa50606b2e84fc4cefe9View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0a6r-9600000000-d08dbc757a6de6c3f54eView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0adi-9800000000-40f904bf20072c72a08bView in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0pk9-9800000000-b93fc1120a1c74b88fa3View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-05i0-5900000000-1b6bbf98557af374f3a5View in MoNA
GC-MSGC-MS Spectrum - EI-Bsplash10-0570-0900000000-ecd208f1e7b4d5ad85f2View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0a70-0900000000-5284a0c1c77a1979e1f4View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-056r-3900000000-1c74c32fa650fcd4cb4dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-0a70-0900000000-cec9e1ab69521049d1e4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS)splash10-05fr-7900000000-1c4c0dbbb165ef614f43View in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-4644ee08861e75d0b808View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00b9-9400000000-11baabb3c0bb283b1c6eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004l-9100000000-4875643627420279223bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-97a21f3206f5c1f0ba7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ee9de948bfb30da0a400View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1900000000-c18a9b04d65d91fdd99eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-9300000000-0878408a026788c942a0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3900000000-f25040451834faf3bf91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-9500000000-b352342b60fd48a0c127View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-1d11331d7d21e32dbdbaView in MoNA
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
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesThis is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
StatusValueUnitSample LocationReference
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 Reference

Ludovicus A. L. Kleintjens, Hubertus M. J. Grooten, “Process for the preparation of benzoic acid.” U.S. Patent US4539425, issued March, 1932.

MSDSLink
General References
1. Hronec, Milan; Mikula, Oldrich; Kopernicky, Ivan; Bucko, Milos; Danilla, Frantisek; Hlinistak, Karol. Process for benzoic acid manufacture. Czech. (1987), 3 pp.
2. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743.
3. Xi X, Kwok LY, Wang Y, Ma C, Mi Z, Zhang H: Ultra-performance liquid chromatography-quadrupole-time of flight mass spectrometry MS(E)-based untargeted milk metabolomics in dairy cows with subclinical or clinical mastitis. J Dairy Sci. 2017 Jun;100(6):4884-4896. doi: 10.3168/jds.2016-11939. Epub 2017 Mar 23.
4. Hronec, Milan; Mikula, Oldrich; Kopernicky, Ivan; Bucko, Milos; Danilla, Frantisek; Hlinistak, Karol. Process for benzoic acid manufacture. Czech. (1987), 3 pp.
5. 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.
6. 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.
7. 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.
8. 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.
9. 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.
10. Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79.
11. 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.
12. Killackey JJ, Killackey BA, Philp RB: Cyclic nucleotide phosphodiesterase inhibition by a benzoic acid derivative. Agents Actions. 1985 Dec;17(2):192-6.
13. 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.
14. 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.
15. Beloborodova N, Bairamov I, Olenin A, Shubina V, Teplova V, Fedotcheva N: Effect of phenolic acids of microbial origin on production of reactive oxygen species in mitochondria and neutrophils. J Biomed Sci. 2012 Oct 12;19:89. doi: 10.1186/1423-0127-19-89.
16. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
17. Publications of the University of Eastern Finland. Dissertations in Health Sciences., no 510
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=16728954
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=17439666
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=18314336