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Record Information
Version3.6
Creation Date2006-02-23 11:42:39 UTC
Update Date2014-12-01 23:17:16 UTC
HMDB IDHMDB01870
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
  1. Benzenecarboxylate
  2. Benzenecarboxylic acid
  3. Benzeneformate
  4. Benzeneformic acid
  5. Benzenemethanoate
  6. Benzenemethanoic acid
  7. Benzenemethonic acid
  8. Benzoate
  9. Benzoic acid
  10. Benzoic acid sodium salt
  11. Carboxybenzene
  12. Diacylate
  13. Diacylic acid
  14. Dracylate
  15. Dracylic acid
  16. Oracylic acid
  17. Phenylcarboxylate
  18. Phenylcarboxylic acid
  19. Phenylformate
  20. Phenylformic acid
  21. Sodium benzoate
  22. Sodium benzoic acid
Chemical FormulaC7H6O2
Average Molecular Weight122.1213
Monoisotopic Molecular Weight122.036779436
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
KingdomOrganic Compounds
Super ClassAromatic Homomonocyclic Compounds
ClassBenzoic Acid and Derivatives
Sub ClassN/A
Other Descriptors
  • Organic Compounds
  • benzoic acids(ChEBI)
Substituents
  • Benzoyl
  • Carboxylic Acid
Direct ParentBenzoic Acid and Derivatives
Ontology
StatusDetected and Quantified
Origin
  • Food
  • Microbial
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Endoplasmic reticulum
Physical Properties
StateSolid
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 Solubility7.08ALOGPS
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
Spectra
SpectraGC-MSMS/MSLC-MSMS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Kidney
  • Liver
  • Skin
  • Stratum Corneum
  • Testes
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified14.327 +/- 2.066 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified10.783 +/- 2.169 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified14.96 +/- 1.994 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified10.49 +/- 2.401 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified12.082 +/- 2.028 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified13.422 +/- 2.406 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified12.467 +/- 2.747 uMAdult (>18 years old)Male
Normal
details
BloodDetected and Quantified77.746 +/- 67.635 uMAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Male
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified158.858 +/- 122.829 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified171.960 +/- 184.243 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
FecesDetected and Quantified308.709 +/- 208.809 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified355.384 +/- 293.970 nmol/g of fecesAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
FecesDetected and Quantified6.551 +/- 4.831 uMNot SpecifiedNot Specified
Normal
details
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Normal
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
SalivaDetected and Quantified13.9 +/- 3.52 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected and Quantified19.5 +/- 8.70 uMAdult (>18 years old)Female
Normal
    • Sugimoto et al. (...
details
SalivaDetected but not QuantifiedNot ApplicableAdult (>18 years old)Not SpecifiedNormal details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 427
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 427
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableConsuming polyphenols described by Phenol-Explorer entry 427
  • Not Applicable
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified106.0 +/- 41.0 umol/mmol creatinineAdult (>18 years old)BothNormal
    • Geigy Scientific ...
details
UrineDetected and Quantified4.2 (1.9-6.5) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.1452 +/- 0.133 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified0.1 umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.6 (1.4 -7.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified4.7 (1.2-10.5) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified1.374 +/- 0.307 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected and Quantified4.042 +/- 0.851 umol/mmol creatinineAdult (>18 years old)Male
Normal
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot ApplicableNot SpecifiedNot Specified
Cryptosporidium infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Campylobacter jejuni infection
details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Clostridium difficile infection
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothBreast cancer details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID427
Phenol Explorer Metabolite ID427
FoodDB IDFDB008739
KNApSAcK IDC00000207
Chemspider ID238
KEGG Compound IDC00180
BioCyc ID1-O6-O-DIGALLOYL-BETA-D-GLUCOSE
BiGG ID34156
Wikipedia LinkBenzoic acid
NuGOwiki LinkHMDB01870
Metagene LinkHMDB01870
METLIN ID1297
PubChem Compound243
PDB IDBEZ
ChEBI ID30746
References
Synthesis ReferenceHronec, 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)
General References
  1. Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79. Pubmed: 357810
  2. 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. Pubmed: 2293213
  3. 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. Pubmed: 7712673
  4. 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. Pubmed: 8135043
  5. 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. Pubmed: 9884323
  6. 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. Pubmed: 2339094
  7. 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. Pubmed: 3379586
  8. Killackey JJ, Killackey BA, Philp RB: Cyclic nucleotide phosphodiesterase inhibition by a benzoic acid derivative. Agents Actions. 1985 Dec;17(2):192-6. Pubmed: 2420162
  9. 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. Pubmed: 7204686
  10. 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. Pubmed: 3229281

Enzymes

General function:
Involved in lipid metabolic process
Specific function:
Crucial for the intracellular hydrolysis of cholesteryl esters and triglycerides that have been internalized via receptor-mediated endocytosis of lipoprotein particles. Important in mediating the effect of LDL (low density lipoprotein) uptake on suppression of hydroxymethylglutaryl-CoA reductase and activation of endogenous cellular cholesteryl ester formation.
Gene Name:
LIPA
Uniprot ID:
P38571
Molecular weight:
45418.71
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
Cocaine + Water → Ecgonine methyl ester + Benzoic aciddetails
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular weight:
68898.39
Reactions
Cocaine + Water → Ecgonine methyl ester + Benzoic aciddetails
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP2
Uniprot ID:
P14621
Molecular weight:
11139.52
Reactions
Benzoyl phosphate + Water → Benzoic acid + Phosphoric aciddetails
General function:
Involved in acylphosphatase activity
Specific function:
Its physiological role is not yet clear.
Gene Name:
ACYP1
Uniprot ID:
P07311
Molecular weight:
11260.84
Reactions
Benzoyl phosphate + Water → Benzoic acid + Phosphoric aciddetails
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs (By similarity).
Gene Name:
CES5A
Uniprot ID:
Q6NT32
Molecular weight:
63925.82