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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-22 16:53:27 UTC

Update Date

2022-09-22 18:34:59 UTC

HMDB ID

HMDB0301753

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Methylcatechol

Description

3-methylcatechol, also known as 2,3-dihydroxytoluene or 2,3-toluenediol, is a member of the class of compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 3-methylcatechol is soluble (in water) and a very weakly acidic compound (based on its pKa). 3-methylcatechol can be found in arabica coffee, beer, cocoa powder, and coffee, which makes 3-methylcatechol a potential biomarker for the consumption of these food products. 3-methylcatechol is a chemical compound .

Structure

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

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-Dihydroxytoluene	ChEBI
3-Methylcatechol	Kegg
2,3-Toluenediol	MeSH

Chemical Formula

C₇H₈O₂

Average Molecular Weight

124.1372

Monoisotopic Molecular Weight

124.0524295

IUPAC Name

3-methylbenzene-1,2-diol

Traditional Name

3-methylcatechol

CAS Registry Number

488-17-5

SMILES

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

InChI Identifier

InChI=1S/C7H8O2/c1-5-3-2-4-6(8)7(5)9/h2-4,8-9H,1H3

InChI Key

PGSWEKYNAOWQDF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

O-cresol
M-cresol
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

methylcatechol (CHEBI:18404 )
a catechol (CPD-111 )

Ontology

Not Available

Exogenous (HMDB: HMDB0301753)

Food

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Cocoa and cocoa product

Cocoa product

Cocoa powder (FooDB: FOOD00685)

Coffee and coffee product

Coffee

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.03	ALOGPS
logP	1.88	ChemAxon
logS	-0.53	ALOGPS
pKa (Strongest Acidic)	9.59	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.06 m³·mol⁻¹	ChemAxon
Polarizability	12.73 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	123.9	32859911
AllCCS	[M+H-H2O]+	119.017	32859911
AllCCS	[M+Na]+	129.777	32859911
AllCCS	[M+NH4]+	128.46	32859911
AllCCS	[M-H]-	119.503	32859911
AllCCS	[M+Na-2H]-	121.538	32859911
AllCCS	[M+HCOO]-	123.817	32859911
DeepCCS	[M+H]+	125.122	30932474
DeepCCS	[M-H]-	121.811	30932474
DeepCCS	[M-2H]-	159.022	30932474
DeepCCS	[M+Na]+	134.176	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.3111 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.87 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1308.5 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	379.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	146.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	247.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	253.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	547.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	553.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	149.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	941.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	372.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1078.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	299.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	384.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	572.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	251.9 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	183.2 seconds	40023050

Predicted Kovats Retention Indices

Not Available

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 3-Methylcatechol EI-B (Non-derivatized)	splash10-00di-7900000000-30c68a9fce29834d697d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 3-Methylcatechol GC-EI-TOF (Non-derivatized)	splash10-0gb9-1930000000-0e12a5db56662ebc8b3c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Methylcatechol GC-MS (Non-derivatized) - 70eV, Positive	splash10-00di-6900000000-0b15087afad3efcb530f	2017-07-27	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-Methylcatechol LC-ESI-QFT , negative-QTOF	splash10-00di-0900000000-d09187141145a60f4a21	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol LC-ESI-QTOF 35V, negative-QTOF	splash10-00di-0900000000-33fd8523a11f2a3f1380	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol n/a 8V, negative-QTOF	splash10-00di-0960000000-3cd3b0c30d267b643753	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol n/a 8V, negative-QTOF	splash10-00di-1900000000-d20dc10f999deda798c4	2020-07-21	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol Orbitrap 3V, negative-QTOF	splash10-00di-0900000000-11da97d52924ca2ad137	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol Orbitrap 4V, negative-QTOF	splash10-00di-0900000000-92dead73d544836d18a3	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol QTOF 4V, positive-QTOF	splash10-056r-1900000000-c8218e952e34419b10ef	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol QTOF 5V, positive-QTOF	splash10-056r-2900000000-294f9b9d3bff7bbe0f07	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol QTOF 7V, positive-QTOF	splash10-056r-3900000000-835bc1392122990ec248	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol QTOF 10V, positive-QTOF	splash10-0a6r-4900000000-c04e3b16f2200208d566	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol QTOF 15V, positive-QTOF	splash10-056r-9500000000-0fb37738b7f252ac17ed	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol QTOF 17V, positive-QTOF	splash10-004i-9300000000-7282ecd0ed591d9f8771	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol Orbitrap 0V, positive-QTOF	splash10-004i-0900000000-8ee1a4e97b3d4d51fbd3	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol Orbitrap 1V, positive-QTOF	splash10-056r-0900000000-ab9953625ddfe2e3a7b2	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol Orbitrap 2V, positive-QTOF	splash10-0a6r-0900000000-9b80e0dbef6fc9b052d2	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol Orbitrap 2V, positive-QTOF	splash10-0a4i-1900000000-f899af43c4d617be07c2	2020-07-22	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 3-Methylcatechol n/a 8V, positive-QTOF	splash10-0a4i-0900000000-a8efa783b158b5e04857	2020-07-22	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylcatechol 10V, Positive-QTOF	splash10-004i-0900000000-3875de3add451f95d6d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylcatechol 20V, Positive-QTOF	splash10-004i-3900000000-eb8a770aa433224b2cb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylcatechol 40V, Positive-QTOF	splash10-014i-9100000000-f3b484e83effcfdf3feb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylcatechol 10V, Negative-QTOF	splash10-00di-0900000000-0b76f1d6ee1da11515be	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylcatechol 20V, Negative-QTOF	splash10-00di-1900000000-d38b8bf198a6b858b397	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylcatechol 40V, Negative-QTOF	splash10-06dl-9300000000-9917e29b70acc74ca008	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylcatechol 10V, Positive-QTOF	splash10-0a6r-1900000000-05b5781f8b9f529505b0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Methylcatechol 20V, Positive-QTOF	splash10-0a6r-9600000000-e48f40f8fb9b564fd3de	2021-10-21	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	34436864	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03454

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000357

KNApSAcK ID

Not Available

Chemspider ID

333

KEGG Compound ID

C02923

BioCyc ID

CPD-111

BiGG ID

Not Available

Wikipedia Link

3-Methylcatechol

METLIN ID

Not Available

PubChem Compound

340

PDB ID

Not Available

ChEBI ID

18404

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1192001

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3-Methylcatechol (HMDB0301753)

MOL for HMDB0301753 (3-Methylcatechol)

3D MOL for HMDB0301753 (3-Methylcatechol)

3D SDF for HMDB0301753 (3-Methylcatechol)

3D-SDF for HMDB0301753 (3-Methylcatechol)

PDB for HMDB0301753 (3-Methylcatechol)

3D PDB for HMDB0301753 (3-Methylcatechol)

SMILES for HMDB0301753 (3-Methylcatechol)

INCHI for HMDB0301753 (3-Methylcatechol)

Structure for HMDB0301753 (3-Methylcatechol)

3D Structure for HMDB0301753 (3-Methylcatechol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

GC-MS Spectra

MS/MS Spectra

NMR Spectra