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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:48 UTC

Update Date

2023-02-21 17:16:21 UTC

HMDB ID

HMDB0002340

Secondary Accession Numbers

HMDB02340

Metabolite Identification

Common Name

2-Methylbenzoic acid

Description

2-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Toluic acid	ChEBI
O-Toluylic acid	ChEBI
Orthotoluic acid	ChEBI
O-Methylbenzoate	Kegg
O-Toluic acid	Kegg
2-Toluate	Generator
O-Toluylate	Generator
Orthotoluate	Generator
O-Methylbenzoic acid	Generator
O-Toluate	Generator
2-Methylbenzoate	Generator
2-Toluic acid, cadmium salt	HMDB
2-Toluic acid, sodium salt, 11C-labeled	HMDB
2-Methylbenzoic acid	ChEBI

Chemical Formula

C₈H₈O₂

Average Molecular Weight

136.1479

Monoisotopic Molecular Weight

136.0524295

IUPAC Name

2-methylbenzoic acid

Traditional Name

o-toluic acid

CAS Registry Number

118-90-1

SMILES

CC1=C(C=CC=C1)C(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 Key

ZWLPBLYKEWSWPD-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.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzoic 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 Framework

Aromatic homomonocyclic compounds

External Descriptors

methylbenzoic acid (CHEBI:36632 )

Ontology

Not Available

Urine (PMID: 24023812)
Feces (PMID: 22411374)

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0002340)

Cellular substructure

Membrane (HMDB: HMDB0002340)

Source

Exogenous

Exogenous (HMDB: HMDB0002340)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	103.7 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1.18 mg/mL at 25 °C	Not Available
LogP	2.46	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	3.02 g/L	ALOGPS
logP	2.03	ALOGPS
logP	2.14	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.96	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	38.36 m³·mol⁻¹	ChemAxon
Polarizability	13.95 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	128.606	31661259
DarkChem	[M-H]-	122.511	31661259
DeepCCS	[M+H]+	128.037	30932474
DeepCCS	[M-H]-	124.42	30932474
DeepCCS	[M-2H]-	161.331	30932474
DeepCCS	[M+Na]+	136.6	30932474
AllCCS	[M+H]+	126.9	32859911
AllCCS	[M+H-H2O]+	122.1	32859911
AllCCS	[M+NH4]+	131.3	32859911
AllCCS	[M+Na]+	132.5	32859911
AllCCS	[M-H]-	124.0	32859911
AllCCS	[M+Na-2H]-	125.6	32859911
AllCCS	[M+HCOO]-	127.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Methylbenzoic acid	CC1=CC=CC=C1C(O)=O	2172.4	Standard polar	33892256
2-Methylbenzoic acid	CC1=CC=CC=C1C(O)=O	1197.6	Standard non polar	33892256
2-Methylbenzoic acid	CC1=CC=CC=C1C(O)=O	1288.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Methylbenzoic acid,1TMS,isomer #1	CC1=CC=CC=C1C(=O)O[Si](C)(C)C	1337.0	Semi standard non polar	33892256
2-Methylbenzoic acid,1TBDMS,isomer #1	CC1=CC=CC=C1C(=O)O[Si](C)(C)C(C)(C)C	1558.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Methylbenzoic acid EI-B (Non-derivatized)	splash10-00ko-9400000000-3ea21e5a2da3e36feaa4	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylbenzoic acid EI-B (Non-derivatized)	splash10-00kf-3910000000-9eadfe119d06c5ce7a2e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylbenzoic acid GC-EI-TOF (Non-derivatized)	splash10-00kf-3900000000-a3c1bae2837699c09729	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylbenzoic acid EI-B (Non-derivatized)	splash10-00ko-9400000000-3ea21e5a2da3e36feaa4	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylbenzoic acid EI-B (Non-derivatized)	splash10-00kf-3910000000-9eadfe119d06c5ce7a2e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Methylbenzoic acid GC-EI-TOF (Non-derivatized)	splash10-00kf-3900000000-a3c1bae2837699c09729	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylbenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-00ku-6900000000-7b91036553046ede2f1a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylbenzoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-00y3-9610000000-54072ddd27062657e60f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylbenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Methylbenzoic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Methylbenzoic acid LC-ESI-QQ , negative-QTOF	splash10-000i-0900000000-d28bc3a7edeb358c7270	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Methylbenzoic acid LC-ESI-QQ , negative-QTOF	splash10-0006-9100000000-bbf58a509b4337ff093f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Methylbenzoic acid LC-ESI-QQ , negative-QTOF	splash10-0006-9100000000-a047fe202a87250f551c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Methylbenzoic acid LC-ESI-QQ , negative-QTOF	splash10-000x-9000000000-7532f7bbbadf3d72cc82	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Methylbenzoic acid 40V, Negative-QTOF	splash10-0006-9000000000-6070bdb4c09a501c042f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Methylbenzoic acid 20V, Negative-QTOF	splash10-0006-9100000000-22194e34cc23ee7c72ab	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Methylbenzoic acid 10V, Negative-QTOF	splash10-0006-9100000000-baca35e1dfdc2f237b45	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 10V, Positive-QTOF	splash10-000i-0900000000-c75cdc962af20d57cd7b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 20V, Positive-QTOF	splash10-014r-1900000000-04a06e806e5b5ffb4339	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 40V, Positive-QTOF	splash10-016r-9100000000-033e7c18f3dec69e1c6c	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 10V, Negative-QTOF	splash10-000i-3900000000-7208577161cc27a2b7ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 20V, Negative-QTOF	splash10-000f-9500000000-a07ab7fb94ed540a362d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 40V, Negative-QTOF	splash10-0006-9100000000-f6d6c60d56607d325e08	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 10V, Positive-QTOF	splash10-014l-6900000000-1bd11c4205e7630504af	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 20V, Positive-QTOF	splash10-00kf-9300000000-778358cd7b815f46b208	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 40V, Positive-QTOF	splash10-002f-9000000000-04f6c3a5c5e28c992faf	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 10V, Negative-QTOF	splash10-0006-9000000000-5671d4c535a6553aaf0d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 20V, Negative-QTOF	splash10-0006-9000000000-5671d4c535a6553aaf0d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Methylbenzoic acid 40V, Negative-QTOF	splash10-0006-9000000000-d4d2c47f972429f0dd88	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Both	Normal	22411374	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Urine	Detected and Quantified	2.8(1.0-4.2) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

O-Toluic_acid

METLIN ID

Not Available

PubChem Compound

8373

PDB ID

Not Available

ChEBI ID

36632

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Ren, 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

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 ]

Showing metabocard for 2-Methylbenzoic acid (HMDB0002340)

MOL for HMDB0002340 (2-Methylbenzoic acid)

3D MOL for HMDB0002340 (2-Methylbenzoic acid)

3D SDF for HMDB0002340 (2-Methylbenzoic acid)

3D-SDF for HMDB0002340 (2-Methylbenzoic acid)

PDB for HMDB0002340 (2-Methylbenzoic acid)

3D PDB for HMDB0002340 (2-Methylbenzoic acid)

SMILES for HMDB0002340 (2-Methylbenzoic acid)

INCHI for HMDB0002340 (2-Methylbenzoic acid)

Structure for HMDB0002340 (2-Methylbenzoic acid)

3D Structure for HMDB0002340 (2-Methylbenzoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra