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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:42 UTC

Update Date

2023-02-21 17:16:16 UTC

HMDB ID

HMDB0002222

Secondary Accession Numbers

HMDB02222

Metabolite Identification

Common Name

3-Methylphenylacetic acid

Description

3-Methylphenylacetic acid, also known as m-methylphenylacetate or m-tolylacetic acid, belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group. 3-Methylphenylacetic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 3-methylphenylacetic acid a potential biomarker for the consumption of these foods. 3-Methylphenylacetic 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 3-Methylphenylacetic 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
3-Tolylacetic acid	ChEBI
m-Methylphenylacetic acid	ChEBI
m-Tolylacetic acid	ChEBI
3-Tolylacetate	Generator
m-Methylphenylacetate	Generator
m-Tolylacetate	Generator
3-Methylphenylacetate	Generator
(3-Methylphenyl)acetate	HMDB
(3-Methylphenyl)acetic acid	HMDB

Chemical Formula

C₉H₁₀O₂

Average Molecular Weight

150.1745

Monoisotopic Molecular Weight

150.068079564

IUPAC Name

2-(3-methylphenyl)acetic acid

Traditional Name

3-methylphenylacetic acid

CAS Registry Number

621-36-3

SMILES

CC1=CC(CC(O)=O)=CC=C1

InChI Identifier

InChI=1S/C9H10O2/c1-7-3-2-4-8(5-7)6-9(10)11/h2-5H,6H2,1H3,(H,10,11)

InChI Key

GJMPSRSMBJLKKB-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Toluenes

Direct Parent

Toluenes

Alternative Parents

Substituents

Toluene
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0002222)
Cell membrane (HMDB: HMDB0002222)

Source

Endogenous

Endogenous (HMDB: HMDB0002222)

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	62 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	4065 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.95	HANSCH,C ET AL. (1995)

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.54 g/L	ALOGPS
logP	2.11	ALOGPS
logP	2.12	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.69	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	2	ChemAxon
Refractivity	42.41 m³·mol⁻¹	ChemAxon
Polarizability	15.93 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]+	133.985	31661259
DarkChem	[M-H]-	129.177	31661259
DeepCCS	[M+H]+	132.664	30932474
DeepCCS	[M-H]-	129.169	30932474
DeepCCS	[M-2H]-	166.564	30932474
DeepCCS	[M+Na]+	142.014	30932474
AllCCS	[M+H]+	130.4	32859911
AllCCS	[M+H-H2O]+	125.8	32859911
AllCCS	[M+NH4]+	134.7	32859911
AllCCS	[M+Na]+	135.9	32859911
AllCCS	[M-H]-	129.7	32859911
AllCCS	[M+Na-2H]-	131.0	32859911
AllCCS	[M+HCOO]-	132.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Methylphenylacetic acid	CC1=CC(CC(O)=O)=CC=C1	2545.1	Standard polar	33892256
3-Methylphenylacetic acid	CC1=CC(CC(O)=O)=CC=C1	1318.8	Standard non polar	33892256
3-Methylphenylacetic acid	CC1=CC(CC(O)=O)=CC=C1	1379.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Methylphenylacetic acid,1TMS,isomer #1	CC1=CC=CC(CC(=O)O[Si](C)(C)C)=C1	1399.5	Semi standard non polar	33892256
3-Methylphenylacetic acid,1TBDMS,isomer #1	CC1=CC=CC(CC(=O)O[Si](C)(C)C(C)(C)C)=C1	1612.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Methylphenylacetic acid EI-B (Non-derivatized)	splash10-0a4i-3900000000-6b850d428cd107b5a318	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Methylphenylacetic acid EI-B (Non-derivatized)	splash10-0a4i-3900000000-6b850d428cd107b5a318	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylphenylacetic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-4900000000-1ae920655088ae3aea40	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylphenylacetic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-9820000000-0c9a62d57fbfd1037477	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylphenylacetic 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 - 3-Methylphenylacetic acid Quattro_QQQ 10V, N/A-QTOF (Annotated)	splash10-0a4i-0900000000-6c8f3dbaf577d500ed03	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylphenylacetic acid Quattro_QQQ 25V, N/A-QTOF (Annotated)	splash10-0a6r-5900000000-f248f213cb494cc0f737	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylphenylacetic acid Quattro_QQQ 40V, N/A-QTOF (Annotated)	splash10-0pb9-0900000000-2ce49413ba732bad2618	2012-07-25	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 10V, Positive-QTOF	splash10-001i-0900000000-c04e8fd94bd4f84bed28	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 20V, Positive-QTOF	splash10-0a4i-1900000000-7907d2fe8f3678d53172	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 40V, Positive-QTOF	splash10-0a4l-9700000000-538f7b242974723a482b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 10V, Negative-QTOF	splash10-052b-0900000000-5b571f7a5f766aac14b3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 20V, Negative-QTOF	splash10-0a5a-0900000000-13d329a5226b06287841	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 40V, Negative-QTOF	splash10-053r-0900000000-807a01f1d049a1aec45d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 10V, Positive-QTOF	splash10-0a4i-2900000000-8c61c713cd6090d01a49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 20V, Positive-QTOF	splash10-0a4i-4900000000-de02c91ae7faea9696cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 40V, Positive-QTOF	splash10-07vl-9200000000-c8053d1998b46d1eae92	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 10V, Negative-QTOF	splash10-0a4i-0900000000-a3f97e87c1c92caaaf5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 20V, Negative-QTOF	splash10-0a59-0900000000-2c48d02effbc9356919b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylphenylacetic acid 40V, Negative-QTOF	splash10-0a4i-1900000000-8cfeda5df3fc15024045	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2021-10-10	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)	2012-12-05	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

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB022916

KNApSAcK ID

Not Available

Chemspider ID

11623

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

6557

PubChem Compound

12121

PDB ID

Not Available

ChEBI ID

88356

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1257321

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

BERNHARD K, VIRET R: [Further studies on the metabolic behavior of some aromatic and hydroaromatic mono- and dicarboxylic acids]. Hoppe Seylers Z Physiol Chem. 1958;310(1-2):37-43. [PubMed:13548876 ]
Nomeir AA, Abou-Donia MB: High-performance liquid chromatographic analysis on radial compression column of the neurotoxic tri-o-cresyl phosphate and metabolites. Anal Biochem. 1983 Dec;135(2):296-303. [PubMed:6660505 ]

Showing metabocard for 3-Methylphenylacetic acid (HMDB0002222)

MOL for HMDB0002222 (3-Methylphenylacetic acid)

3D MOL for HMDB0002222 (3-Methylphenylacetic acid)

3D SDF for HMDB0002222 (3-Methylphenylacetic acid)

3D-SDF for HMDB0002222 (3-Methylphenylacetic acid)

PDB for HMDB0002222 (3-Methylphenylacetic acid)

3D PDB for HMDB0002222 (3-Methylphenylacetic acid)

SMILES for HMDB0002222 (3-Methylphenylacetic acid)

INCHI for HMDB0002222 (3-Methylphenylacetic acid)

Structure for HMDB0002222 (3-Methylphenylacetic acid)

3D Structure for HMDB0002222 (3-Methylphenylacetic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra