Benzoic acid (T3D4785)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (5)XML
Targets (5)
Record Information
Version2.0
Creation Date2014-09-11 05:16:29 UTC
Update Date2014-12-24 20:26:57 UTC
Accession NumberT3D4785
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).
Compound Type
  • Animal Toxin
  • Ester
  • Food Preservative
  • Food Toxin
  • Household Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
  • Plant Toxin
  • Preservative
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
Benzenecarboxylate
Benzenecarboxylic acid
Benzeneformate
Benzeneformic acid
Benzenemethanoate
Benzenemethanoic acid
Benzenemethonic acid
Benzoate
Benzoic acid sodium salt
Carboxybenzene
Diacylate
Diacylic acid
Dracylate
Dracylic acid
Oracylic acid
Phenylcarboxylate
Phenylcarboxylic acid
Phenylformate
Phenylformic acid
Sodium benzoate
Sodium benzoic acid
Chemical FormulaC7H6O2
Average Molecular Mass122.121 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 KeyInChIKey=WPYMKLBDIGXBTP-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)
LogP1.87
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 KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0a70-0900000000-5284a0c1c77a1979e1f42014-06-16View Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-056r-3900000000-1c74c32fa650fcd4cb4d2014-06-16View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i0-6900000000-fa50606b2e84fc4cefe92017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a6r-9600000000-d08dbc757a6de6c3f54e2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0adi-9800000000-40f904bf20072c72a08b2017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0pk9-9800000000-b93fc1120a1c74b88fa32017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-05i0-5900000000-1b6bbf98557af374f3a52017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0570-0900000000-ecd208f1e7b4d5ad85f22017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a70-0900000000-5284a0c1c77a1979e1f42017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-056r-3900000000-1c74c32fa650fcd4cb4d2017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a70-0900000000-cec9e1ab69521049d1e42017-09-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kmi-7900000000-5ad752bd6787261a11d02016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-7900000000-1c4c0dbbb165ef614f432017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00b9-9500000000-f312a552bef1a2927e642012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-dafd91c9134bc41437432012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00b9-9400000000-29ca905567aa5c59d46b2012-07-24View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positivesplash10-05i0-6900000000-fa50606b2e84fc4cefe92012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-0a6r-9600000000-d08dbc757a6de6c3f54e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0adi-9800000000-2693809ae064e720bf582012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0pk9-9800000000-2c6be5ecee1848091a242012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-4644ee08861e75d0b8082012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00b9-9400000000-11baabb3c0bb283b1c6e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004l-9100000000-4875643627420279223b2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-97a21f3206f5c1f0ba7e2012-08-31View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-4644ee08861e75d0b8082017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00b9-9400000000-11baabb3c0bb283b1c6e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004l-9100000000-4875643627420279223b2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-97a21f3206f5c1f0ba7e2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00di-0900000000-94c7f13620a367bf55162021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00di-0900000000-f060e7aa8085ec6be2232021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-00di-0900000000-a28fdef9c1c00d45c3ff2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-0900000000-3cad9aa6b0980c87bcc32021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ee9de948bfb30da0a4002016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1900000000-c18a9b04d65d91fdd99e2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-9300000000-0878408a026788c942a02016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3900000000-f25040451834faf3bf912016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-9500000000-b352342b60fd48a0c1272016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-1d11331d7d21e32dbdba2016-09-12View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0pk9-8900000000-3d79c70c455799ab33e32014-09-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not Available2012-12-04View Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Not Available2014-09-20View Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Not Available2014-09-23View Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not Available2016-10-22View Spectrum
2D NMR[1H, 1H]-TOCSY. Unexported temporarily by An Chi on Oct 15, 2021 until json or nmrML file is generated. 2D NMR Spectrum (experimental)Not Available2012-12-04View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not Available2012-12-05View Spectrum
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
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB03793
HMDB IDHMDB01870
PubChem Compound ID243
ChEMBL IDNot Available
ChemSpider ID238
KEGG IDC00180
UniProt IDNot Available
OMIM ID
ChEBI ID30746
BioCyc ID1-O6-O-DIGALLOYL-BETA-D-GLUCOSE
CTD IDNot Available
Stitch IDNot Available
PDB IDBEZ
ACToR IDNot Available
Wikipedia LinkBenzoic acid
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. 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. [8135043 ]
  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. [9884323 ]
  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. [2293213 ]
  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. [2339094 ]
  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. [3379586 ]
  6. Jones MR, Kopple JD, Swendseid ME: Phenylalanine metabolism in uremic and normal man. Kidney Int. 1978 Aug;14(2):169-79. [357810 ]
  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. [7712673 ]
  8. Killackey JJ, Killackey BA, Philp RB: Cyclic nucleotide phosphodiesterase inhibition by a benzoic acid derivative. Agents Actions. 1985 Dec;17(2):192-6. [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. [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. [3229281 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. D-amino-acid oxidase
General Function:
Receptor binding
Specific Function:
Regulates the level of the neuromodulator D-serine in the brain. Has high activity towards D-DOPA and contributes to dopamine synthesis. Could act as a detoxifying agent which removes D-amino acids accumulated during aging. Acts on a variety of D-amino acids with a preference for those having small hydrophobic side chains followed by those bearing polar, aromatic, and basic groups. Does not act on acidic amino acids.
Gene Name:
DAO
Uniprot ID:
P14920
Molecular Weight:
39473.75 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [10592235 ]
Target Details
2. Peroxiredoxin-5, mitochondrial
General Function:
Rna polymerase iii regulatory region dna binding
Specific Function:
Reduces hydrogen peroxide and alkyl hydroperoxides with reducing equivalents provided through the thioredoxin system. Involved in intracellular redox signaling.
Gene Name:
PRDX5
Uniprot ID:
P30044
Molecular Weight:
22086.245 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
Target Details
3. Ras-related protein Rab-9A
General Function:
Gtpase activity
Specific Function:
Involved in the transport of proteins between the endosomes and the trans Golgi network.
Gene Name:
RAB9A
Uniprot ID:
P51151
Molecular Weight:
22837.38 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
Target Details
4. Ribonuclease UK114
General Function:
Xenon atom binding
Specific Function:
Endoribonuclease responsible for the inhibition of the translation by cleaving mRNA. Inhibits cell-free protein synthesis. Cleaves phosphodiester bonds only in single-stranded RNA (By similarity).
Gene Name:
HRSP12
Uniprot ID:
P52758
Molecular Weight:
14493.53 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
Target Details
5. Estrogen receptor
General Function:
Zinc ion binding
Specific Function:
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC506.57 uMTox21_ERa_LUC_BG1_AgonistTox21/NCGC
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]