Human Metabolome Database Version 3.5

Showing metabocard for Benzoic acid (HMDB01870)

Record Information
Version 3.5
Creation Date 2006-02-23 04:42:39 -0700
Update Date 2013-02-08 17:10:54 -0700
HMDB ID HMDB01870
Secondary Accession Numbers None
Metabolite Identification
Common Name Benzoic acid
Description Benzoic 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C7H6O2
Average Molecular Weight 122.1213
Monoisotopic Molecular Weight 122.036779436
IUPAC Name benzoic acid
Traditional IUPAC Name benzoic acid
CAS Registry Number 65-85-0
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 Key WPYMKLBDIGXBTP-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Homomonocyclic Compounds
Class Benzoic Acid and Derivatives
Sub Class N/A
Other Descriptors
  • Organic Compounds
  • benzoic acids(ChEBI)
Substituents
  • Benzoyl
  • Carboxylic Acid
Direct Parent Benzoic Acid and Derivatives
Ontology
Status Detected and Quantified
Origin
  • Food
  • Microbial
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
  • Extracellular
  • Endoplasmic reticulum
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 122.4 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 3.4 mg/mL at 25 °C Not Available
LogP 1.87 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
Water Solubility 7.08 g/L ALOGPS
LogP 1.72 ALOGPS
LogP 1.63 ChemAxon
LogS -1.24 ALOGPS
pKa (strongest acidic) 4.08 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 33.31 ChemAxon
Polarizability 11.97 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (HITACHI RMU-7)
MS/MS Spectrum EI-B (HITACHI RMU-6E)
MS/MS Spectrum EI-B (HITACHI RMU-7M)
MS/MS Spectrum EI-B (HITACHI M-80B)
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 10
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 20
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 30
MS/MS Spectrum LC-ESI-QQ (API3000, Applied Biosystems) 40
MS/MS Spectrum GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies )
MS/MS Spectrum GC-MS
[1H,1H] 2D NMR Spectrum
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Endoplasmic reticulum
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Bladder
  • Fibroblasts
  • Testes
  • Kidney
  • Liver
  • Skin
  • Stratum Corneum
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
14.327 +/- 2.066 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
10.783 +/- 2.169 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
14.96 +/- 1.994 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
10.49 +/- 2.401 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
12.082 +/- 2.028 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
13.422 +/- 2.406 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
12.467 +/- 2.747 uM Adult (>18 years old) Male Comment Normal
Blood Detected and Quantified
77.746 +/- 67.635 uM Adult (>18 years old) Male Comment Normal
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 427
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 427
  • Not Applicable
Urine Expected but not Quantified
Not Applicable Not Available Not Available Consuming polyphenols described by Phenol-Explorer entry 427
  • Not Applicable
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
106.0 +/- 41.0 umol/mmol creatinine Adult (>18 years old) Both Normal
  • Geigy Scient...
Urine Detected and Quantified
4.2 (1.9-6.5) umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
0.1452 +/- 0.133 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
0.1 umol/mmol creatinine Adult (>18 years old) Both Normal
Urine Detected and Quantified
3.6 (1.4 -7.5) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
4.7 (1.2-10.5) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
1.374 +/- 0.307 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Urine Detected and Quantified
4.042 +/- 0.851 umol/mmol creatinine Adult (>18 years old) Male Comment Normal
Urine Detected but not Quantified
Not Applicable Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected but not Quantified Not Applicable Adult (>18 years old) Both Breast cancer
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID 427 Link_out
Phenol Explorer Metabolite ID 427 Link_out
FoodDB ID FDB008739
KNApSAcK ID C00000207 Link_out
Chemspider ID 238 Link_out
KEGG Compound ID C00180 Link_out
BioCyc ID 1-O6-O-DIGALLOYL-BETA-D-GLUCOSE Link_out
BiGG ID 34156 Link_out
Wikipedia Link Benzoic acid Link_out
NuGOwiki Link HMDB01870 Link_out
Metagene Link HMDB01870 Link_out
METLIN ID 1297 Link_out
PubChem Compound 243 Link_out
PDB ID BEZ Link_out
ChEBI ID 30746 Link_out
References
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)
General References
  1. 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 Link_out
  2. 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 Link_out
  3. 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 Link_out
  4. 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 Link_out
  5. 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 Link_out
  6. Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79. Pubmed: 357810 Link_out
  7. 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 Link_out
  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 Link_out
  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 Link_out
  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 Link_out

Enzymes
Name: Lysosomal acid lipase/cholesteryl ester hydrolase
Reactions: Not Available
Gene Name: LIPA
Uniprot ID: P38571 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Liver carboxylesterase 1
Reactions:
Cocaine + Water unknown Ecgonine methyl ester + Benzoic acid details
Gene Name: CES1
Uniprot ID: P23141 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cocaine esterase
Reactions:
Cocaine + Water unknown Ecgonine methyl ester + Benzoic acid details
Gene Name: CES2
Uniprot ID: O00748 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylphosphatase-2
Reactions:
Benzoyl phosphate + Water unknown Benzoic acid + Phosphoric acid details
Gene Name: ACYP2
Uniprot ID: P14621 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acylphosphatase-1
Reactions:
Benzoyl phosphate + Water unknown Benzoic acid + Phosphoric acid details
Gene Name: ACYP1
Uniprot ID: P07311 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Carboxylesterase 5A
Reactions: Not Available
Gene Name: CES5A
Uniprot ID: Q6NT32 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA