Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-05-22 14:17:48 UTC
Update Date2022-03-07 02:49:14 UTC
HMDB IDHMDB0002340
Secondary Accession Numbers
  • HMDB02340
Metabolite Identification
Common Name2-Methylbenzoic acid
Description2-Methylbenzoic acid, also known as 2-toluic acid or O-methylbenzoate, 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. 2-Methylbenzoic acid has been detected, but not quantified in, milk (cow). This could make 2-methylbenzoic acid a potential biomarker for the consumption of these foods. 2-Methylbenzoic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2-Methylbenzoic acid.
Structure
Data?1582752244
Synonyms
ValueSource
2-Toluic acidChEBI
O-Toluylic acidChEBI
Orthotoluic acidChEBI
O-MethylbenzoateKegg
O-Toluic acidKegg
2-ToluateGenerator
O-ToluylateGenerator
OrthotoluateGenerator
O-Methylbenzoic acidGenerator
O-ToluateGenerator
2-MethylbenzoateGenerator
2-Toluic acid, cadmium saltHMDB
2-Toluic acid, sodium salt, 11C-labeledHMDB
2-Methylbenzoic acidChEBI
Chemical FormulaC8H8O2
Average Molecular Weight136.1479
Monoisotopic Molecular Weight136.0524295
IUPAC Name2-methylbenzoic acid
Traditional Nameo-toluic acid
CAS Registry Number118-90-1
SMILES
CC1=CC=CC=C1C(O)=O
InChI Identifier
InChI=1S/C8H8O2/c1-6-4-2-3-5-7(6)8(9)10/h2-5H,1H3,(H,9,10)
InChI KeyZWLPBLYKEWSWPD-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
  • Toluene
  • 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
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point103.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.18 mg/mL at 25 °CNot Available
LogP2.46HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.02 g/LALOGPS
logP2.03ALOGPS
logP2.14ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)3.96ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity38.36 m³·mol⁻¹ChemAxon
Polarizability13.95 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.60631661259
DarkChem[M-H]-122.51131661259
DeepCCS[M+H]+128.03730932474
DeepCCS[M-H]-124.4230932474
DeepCCS[M-2H]-161.33130932474
DeepCCS[M+Na]+136.630932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Methylbenzoic acidCC1=CC=CC=C1C(O)=O2172.4Standard polar33892256
2-Methylbenzoic acidCC1=CC=CC=C1C(O)=O1197.6Standard non polar33892256
2-Methylbenzoic acidCC1=CC=CC=C1C(O)=O1288.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Methylbenzoic acid,1TMS,isomer #1CC1=CC=CC=C1C(=O)O[Si](C)(C)C1337.0Semi standard non polar33892256
2-Methylbenzoic acid,1TBDMS,isomer #1CC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C1558.5Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Methylbenzoic acid EI-B (Non-derivatized)splash10-00ko-9400000000-3ea21e5a2da3e36feaa42017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylbenzoic acid EI-B (Non-derivatized)splash10-00kf-3910000000-9eadfe119d06c5ce7a2e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylbenzoic acid GC-EI-TOF (Non-derivatized)splash10-00kf-3900000000-a3c1bae2837699c097292017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylbenzoic acid EI-B (Non-derivatized)splash10-00ko-9400000000-3ea21e5a2da3e36feaa42018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylbenzoic acid EI-B (Non-derivatized)splash10-00kf-3910000000-9eadfe119d06c5ce7a2e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Methylbenzoic acid GC-EI-TOF (Non-derivatized)splash10-00kf-3900000000-a3c1bae2837699c097292018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylbenzoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-00ku-6900000000-7b91036553046ede2f1a2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylbenzoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00y3-9610000000-54072ddd27062657e60f2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylbenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Methylbenzoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylbenzoic acid LC-ESI-QQ , negative-QTOFsplash10-000i-0900000000-d28bc3a7edeb358c72702017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylbenzoic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9100000000-bbf58a509b4337ff093f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylbenzoic acid LC-ESI-QQ , negative-QTOFsplash10-0006-9100000000-a047fe202a87250f551c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylbenzoic acid LC-ESI-QQ , negative-QTOFsplash10-000x-9000000000-7532f7bbbadf3d72cc822017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylbenzoic acid 40V, Negative-QTOFsplash10-0006-9000000000-6070bdb4c09a501c042f2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylbenzoic acid 20V, Negative-QTOFsplash10-0006-9100000000-22194e34cc23ee7c72ab2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Methylbenzoic acid 10V, Negative-QTOFsplash10-0006-9100000000-baca35e1dfdc2f237b452021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 10V, Positive-QTOFsplash10-000i-0900000000-c75cdc962af20d57cd7b2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 20V, Positive-QTOFsplash10-014r-1900000000-04a06e806e5b5ffb43392016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 40V, Positive-QTOFsplash10-016r-9100000000-033e7c18f3dec69e1c6c2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 10V, Negative-QTOFsplash10-000i-3900000000-7208577161cc27a2b7ec2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 20V, Negative-QTOFsplash10-000f-9500000000-a07ab7fb94ed540a362d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 40V, Negative-QTOFsplash10-0006-9100000000-f6d6c60d56607d325e082016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 10V, Positive-QTOFsplash10-014l-6900000000-1bd11c4205e7630504af2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 20V, Positive-QTOFsplash10-00kf-9300000000-778358cd7b815f46b2082021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 40V, Positive-QTOFsplash10-002f-9000000000-04f6c3a5c5e28c992faf2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 10V, Negative-QTOFsplash10-0006-9000000000-5671d4c535a6553aaf0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 20V, Negative-QTOFsplash10-0006-9000000000-5671d4c535a6553aaf0d2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 40V, Negative-QTOFsplash10-0006-9000000000-d4d2c47f972429f0dd882021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
  • Saliva
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Both
Normal
details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified2.8(1.0-4.2) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB098186
KNApSAcK IDC00000487
Chemspider ID8070
KEGG Compound IDC07215
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkO-Toluic_acid
METLIN IDNot Available
PubChem Compound8373
PDB IDNot Available
ChEBI ID36632
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceRen, Jun. Study on preparation of o-methylbenzoic acid from liquid-phase oxidation of o-xylene. Huagong Shikan (1997), 11(6), 19-20.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Yu WY, Yang LX, Xie JS, Zhou L, Jiang XY, Zhu DX, Muramatsu M, Wang MW: Derivatives of aryl-4-guanidinomethylbenzoate and N-aryl-4-guanidinomethylbenzamide as new antibacterial agents: synthesis and bioactivity. Acta Pharmacol Sin. 2008 Feb;29(2):267-77. [PubMed:18215358 ]