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Benzoic acid (FDB008739)

Record Information
Version1.0
Creation date2010-04-08 22:08:13 UTC
Update date2024-11-29 22:26:50 UTC
Primary IDFDB008739
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameBenzoic acid
DescriptionWidespread in plants especies in essential oils and fruits, mostly in esterified formand is also present in butter, cooked meats, pork fat, white wine, black and green tea, mushroom and Bourbon vanilla. It is used in foodstuffs as antimicrobial and flavouring agent and as preservative. In practical food preservation, the Na salt of benzoic acid is the most widely used form (see MDQ71-S). The antimicrobial activity comprises a wide range of microorganisms, particularly yeasts and moulds. Undissociated benzoic acid is more effective than dissociated, thus the preservative action is more efficient in acidic foodstuffs. Typical usage levels are 500-2000 ppm. Benzoic acid is found in many foods, some of which are animal foods, common grape, lovage, and fruits.
CAS Number65-85-0
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC7H6O2
IUPAC namebenzoic acid
InChI IdentifierInChI=1S/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
InChI KeyWPYMKLBDIGXBTP-UHFFFAOYSA-N
Isomeric SMILESOC(=O)C1=CC=CC=C1
Average Molecular Weight122.123
Monoisotopic Molecular Weight122.036779433
Classification
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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Environmental role:

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 68.85%; H 4.95%; O 26.20%DFC
Melting PointMp 122°DFC
Boiling PointBp10 133°DFC
Experimental Water Solubility3.4 mg/mL at 25 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP1.87HANSCH,C ET AL. (1995)
Experimental pKa4.19
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data300 (E1%/1cm 46.8) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0pk9-8900000000-3d79c70c455799ab33e32014-09-20View Spectrum
GC-MSBenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0a70-0900000000-5284a0c1c77a1979e1f4Spectrum
GC-MSBenzoic acid, 1 TMS, GC-MS Spectrumsplash10-056r-3900000000-1c74c32fa650fcd4cb4dSpectrum
GC-MSBenzoic acid, non-derivatized, GC-MS Spectrumsplash10-05i0-6900000000-fa50606b2e84fc4cefe9Spectrum
GC-MSBenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0a6r-9600000000-d08dbc757a6de6c3f54eSpectrum
GC-MSBenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0adi-9800000000-40f904bf20072c72a08bSpectrum
GC-MSBenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0pk9-9800000000-b93fc1120a1c74b88fa3Spectrum
GC-MSBenzoic acid, non-derivatized, GC-MS Spectrumsplash10-05i0-5900000000-1b6bbf98557af374f3a5Spectrum
GC-MSBenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0570-0900000000-ecd208f1e7b4d5ad85f2Spectrum
GC-MSBenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0a70-0900000000-5284a0c1c77a1979e1f4Spectrum
GC-MSBenzoic acid, non-derivatized, GC-MS Spectrumsplash10-056r-3900000000-1c74c32fa650fcd4cb4dSpectrum
GC-MSBenzoic acid, non-derivatized, GC-MS Spectrumsplash10-0a70-0900000000-cec9e1ab69521049d1e4Spectrum
Predicted GC-MSBenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0kmi-7900000000-5ad752bd6787261a11d0Spectrum
Predicted GC-MSBenzoic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-05fr-7900000000-1c4c0dbbb165ef614f43Spectrum
Predicted GC-MSBenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSBenzoic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-00b9-9500000000-f312a552bef1a2927e642012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9100000000-dafd91c9134bc41437432012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00b9-9400000000-29ca905567aa5c59d46b2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7) , Positivesplash10-05i0-6900000000-fa50606b2e84fc4cefe92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positivesplash10-0a6r-9600000000-d08dbc757a6de6c3f54e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI RMU-7M) , Positivesplash10-0adi-9800000000-2693809ae064e720bf582012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0pk9-9800000000-2c6be5ecee1848091a242012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-00di-0900000000-4644ee08861e75d0b8082012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-00b9-9400000000-11baabb3c0bb283b1c6e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-004l-9100000000-4875643627420279223b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-0006-9000000000-97a21f3206f5c1f0ba7e2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00di-0900000000-4644ee08861e75d0b8082017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-00b9-9400000000-11baabb3c0bb283b1c6e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-004l-9100000000-4875643627420279223b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0006-9000000000-97a21f3206f5c1f0ba7e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 45V, Negativesplash10-00di-0900000000-94c7f13620a367bf55162021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 75V, Negativesplash10-00di-0900000000-f060e7aa8085ec6be2232021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 60V, Negativesplash10-00di-0900000000-a28fdef9c1c00d45c3ff2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 30V, Negativesplash10-00di-0900000000-3cad9aa6b0980c87bcc32021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-ee9de948bfb30da0a4002016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0ab9-1900000000-c18a9b04d65d91fdd99e2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zi0-9300000000-0878408a026788c942a02016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-3900000000-f25040451834faf3bf912016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00b9-9500000000-b352342b60fd48a0c1272016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9100000000-1d11331d7d21e32dbdba2016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 90 MHz, CDCl3, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 25.16 MHz, CDCl3, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, D2O, experimental)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)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID238
ChEMBL IDCHEMBL541
KEGG Compound IDC00539
Pubchem Compound ID243
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID427
DrugBank IDDB03793
HMDB IDHMDB01870
CRC / DFC (Dictionary of Food Compounds) IDDVN38-Z:DVN38-Z
EAFUS ID303
Dr. Duke IDBENZOIC-ACID
BIGG ID34156
KNApSAcK IDC00000207
HET IDBEZ
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet ID65-85-0
GoodScent IDrw1033731
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID427
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
allergenic50904 A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.DUKE
anestheticDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti otitic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti pyretic35493 A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.DUKE
anti salmonella33282 A substance that kills or slows the growth of bacteria.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti yeast33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
cholereticDUKE
expectorant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
flavor48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
insectifuge24852 Strictly, a substance intended to kill members of the class Insecta. In common usage, any substance used for preventing, destroying, repelling or controlling insects.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
phytoalexin26115 A toxin made by a plant that acts against an organism attacking it.DUKE
tyrosinase inhibitor59997 Any EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.DUKE
uricosuricDUKE
vulnerary73336 A drug used in treating and healing of wounds.DUKE
Enzymes
NameGene NameUniProt ID
Liver carboxylesterase 1CES1P23141
Lysosomal acid lipase/cholesteryl ester hydrolaseLIPAP38571
Carboxylesterase 5ACES5AQ6NT32
Cocaine esteraseCES2O00748
Acylphosphatase-2ACYP2P14621
Acylphosphatase-1ACYP1P07311
Pathways
NameSMPDB LinkKEGG Link
Metabolism and Physiological Effects of Hippuric AcidSMP0123209 Not Available
Metabolism and Physiological Effects of 4-Hydroxyhippuric Acid SMP0125537 Not Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
urine
  1. Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
  2. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
faint
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
balsam
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Saxholt, E., et al. 'Danish food composition databank, revision 7.' Department of Nutrition, National Food Institute, Technical University of Denmark (2008).