Showing Compound Card for 3-Methyl-1,2-benzenediol (CDB005848)

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Record Information
Version1.0
Created at2020-04-27 17:02:36 UTC
Updated at2021-01-04 18:59:33 UTC
CannabisDB IDCDB005848
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name3-Methyl-1,2-benzenediol
Description3-Methylcatechol, also known as 2,3-Toluenediol or 3-Methyl-1,2-benzenediol, is a methylated derivative of catechol or 1,2-Benzenediol. It belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-Benzenediol moiety. 3-Methylcatechol is one of several structural isomers of methylbenzenediol wherein the methyl and two hydroxyl groups are substituted at different positions of the benzene ring. 3-Methylcatechol exists as a white to yellow powder and is soluble in water. It is produced by some bacteria capable of degrading toluene and by other bacteria capable of degrading nitroaromatic compounds present in pesticide-contaminated soil samples (PMID: 13680334 ; PMID: 17337538 ). 3-Methylcatechol naturally produced by a number of plants and is found in a few different foods, such as arabica coffee, cocoa powders and beers. This could make 3-methylcatechol a potential biomarker for the consumption of these foods. Methylbenzenediols are found in cannabis smoke. 3-Methylcatechol is formed during the combustion of cannabis ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2,3-DihydroxytolueneChEBI
3-MethylcatecholKegg
2,3-ToluenediolMeSH
Chemical FormulaC7H8O2
Average Molecular Weight124.14
Monoisotopic Molecular Weight124.0524
IUPAC Name3-methylbenzene-1,2-diol
Traditional Name3-methylcatechol
CAS Registry Number488-17-5
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 KeyPGSWEKYNAOWQDF-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenols
Sub ClassBenzenediols
Direct ParentCatechols
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.03ALOGPS
logP1.88ChemAxon
logS-0.53ALOGPS
pKa (Strongest Acidic)9.59ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.06 m³·mol⁻¹ChemAxon
Polarizability12.73 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS3-Methyl-1,2-benzenediol, non-derivatized, GC-MS Spectrumsplash10-00di-7900000000-30c68a9fce29834d697dSpectrum
GC-MS3-Methyl-1,2-benzenediol, non-derivatized, GC-MS Spectrumsplash10-0gb9-1930000000-0e12a5db56662ebc8b3cSpectrum
Predicted GC-MS3-Methyl-1,2-benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-6900000000-0b15087afad3efcb530fSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - LC-ESI-QFT , negativesplash10-00di-0900000000-d09187141145a60f4a212020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF 35V, negativesplash10-00di-0900000000-33fd8523a11f2a3f13802020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-00di-0960000000-3cd3b0c30d267b6437532020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, negativesplash10-00di-1900000000-d20dc10f999deda798c42020-07-21View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, negativesplash10-00di-0900000000-11da97d52924ca2ad1372020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, negativesplash10-00di-0900000000-92dead73d544836d18a32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 4V, positivesplash10-056r-1900000000-c8218e952e34419b10ef2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 5V, positivesplash10-056r-2900000000-294f9b9d3bff7bbe0f072020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 7V, positivesplash10-056r-3900000000-835bc1392122990ec2482020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 10V, positivesplash10-0a6r-4900000000-c04e3b16f2200208d5662020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 15V, positivesplash10-056r-9500000000-0fb37738b7f252ac17ed2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - QTOF 17V, positivesplash10-004i-9300000000-7282ecd0ed591d9f87712020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-004i-0900000000-8ee1a4e97b3d4d51fbd32020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-056r-0900000000-ab9953625ddfe2e3a7b22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0a6r-0900000000-9b80e0dbef6fc9b052d22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0a4i-1900000000-f899af43c4d617be07c22020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 8V, positivesplash10-0a4i-0900000000-a8efa783b158b5e048572020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-3875de3add451f95d6d22016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-3900000000-eb8a770aa433224b2cb82016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9100000000-f3b484e83effcfdf3feb2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-0b76f1d6ee1da11515be2016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-d38b8bf198a6b858b3972016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06dl-9300000000-9917e29b70acc74ca0082016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-1900000000-05b5781f8b9f529505b02021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-9600000000-e48f40f8fb9b564fd3de2021-10-21View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0301753
DrugBank IDDB03454
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000357
KNApSAcK IDNot Available
Chemspider ID333
KEGG Compound IDC02923
BioCyc IDCPD-111
BiGG IDNot Available
Wikipedia Link3-Methylcatechol
METLIN IDNot Available
PubChem Compound340
PDB IDNot Available
ChEBI ID18404
References
General References
  1. Husken LE, Hoogakker J, de Bont JA, Tramper J, Beeftink HH: Model description of bacterial 3-methylcatechol production in one- and two-phase systems. Bioprocess Biosyst Eng. 2003 Nov;26(1):11-7. doi: 10.1007/pl00021284. Epub 2003 Jul 4. [PubMed:13680334 ]
  2. Rivera-Cancel G, Bocioaga D, Hay AG: Bacterial degradation of N,N-diethyl-m-toluamide (DEET): cloning and heterologous expression of DEET hydrolase. Appl Environ Microbiol. 2007 May;73(9):3105-8. doi: 10.1128/AEM.02765-06. Epub 2007 Mar 2. [PubMed:17337538 ]