Showing Compound Card for 4-Methyl-1,2-benzenediol (CDB005849)

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Record Information
Version1.0
Created at2020-04-27 17:02:42 UTC
Updated at2021-01-06 19:06:57 UTC
CannabisDB IDCDB005849
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Name4-Methyl-1,2-benzenediol
Description4-Methylcatechol or 4-Methyl-1,2-benzenediol, also known as homocatechol or toluene-3,4-diol, belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. 4-Methylcatechol is found in the highest concentration within different foods, such as coffee and cocoa powders and in lower concentration in beers. 4-Methylcatechol has also been detected, but not quantified, in eggplants. It is both a substrate and a suicide inhibitor of catechol 2,3-dioxygenase (PMID: 15006807 ). 4-Methylcatechol is a metabolite of homoprotocatechuic acid (PMID: 4974346 ). Recent studies have suggested that a lack of brain-derived neurotrophic factor (BDNF) in the limbic system may cause neuropathic pain (PMID: 22198556 ). 4-Methylcatechol is known to induce the production of BDNF. 4-Methylcatechol is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1,2-Dihydroxy-4-methylbenzeneChEBI
2-Hydroxy-4-methylphenolChEBI
3,4-DihydroxytolueneChEBI
4-Methyl-1,2-benzenediolChEBI
4-Methyl-1,2-dihydroxybenzeneChEBI
4-MethylpyrocatecholChEBI
HomocatecholChEBI
HomopyrocatecholChEBI
p-MethylcatecholChEBI
p-MethylpyrocatecholChEBI
Toluene-3,4-diolChEBI
1-Methyl-3,4-dihydroxybenzeneHMDB
4-Methyl-pyrocatecholHMDB
4-MethylcateholHMDB
4-MetylcatecholHMDB
5-MethylcatecholHMDB
Chemical FormulaC7H8O2
Average Molecular Weight124.14
Monoisotopic Molecular Weight124.0524
IUPAC Name4-methylbenzene-1,2-diol
Traditional Name4-methyl-1,2-benzenediol
CAS Registry Number452-86-8
SMILES
CC1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
InChI KeyZBCATMYQYDCTIZ-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
  • P-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
Disposition

Route of exposure:

Biological location:

Source:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point65 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logP1.37HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
logP1.02ALOGPS
logP1.88ChemAxon
logS-0.52ALOGPS
pKa (Strongest Acidic)9.55ChemAxon
pKa (Strongest Basic)-6.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area40.46 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.06 m³·mol⁻¹ChemAxon
Polarizability12.82 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS4-Methyl-1,2-benzenediol, non-derivatized, GC-MS Spectrumsplash10-014i-1930000000-6225053efa0739efca3dSpectrum
GC-MS4-Methyl-1,2-benzenediol, non-derivatized, GC-MS Spectrumsplash10-014i-1930000000-6225053efa0739efca3dSpectrum
Predicted GC-MS4-Methyl-1,2-benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-4900000000-2d8d69f64905f6f9396eSpectrum
Predicted GC-MS4-Methyl-1,2-benzenediol, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0udj-3940000000-d5331c4c752130a85084Spectrum
Predicted GC-MS4-Methyl-1,2-benzenediol, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Methyl-1,2-benzenediol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Methyl-1,2-benzenediol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Methyl-1,2-benzenediol, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Methyl-1,2-benzenediol, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS4-Methyl-1,2-benzenediol, TBDMS_2_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a6r-1900000000-9045a710867168d6cc512012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-0e20b47a091c0b3e39ab2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-0e20b47a091c0b3e39ab2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-7db9fcc9e56ad8a390802017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014j-9200000000-f6f538341319fcc5433b2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-97cd131a887e2f8701862021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-6981a2924f054e884c5c2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-0900000000-0aaf237b7039ed11a1d72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0553-9000000000-fe5754c269058c591feb2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-c1c0f17738a12823f96d2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-2900000000-e5f3b6d9329514c202a82021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-d5abc716689493ede24f2021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-6bd82a87c9fe3a5ac3f72021-09-20View Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03dj-9000000000-5833215eaa6163ad44f42021-09-20View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-efa52ff0e22aa918c8322017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-1813508ce877db8f3b512017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9200000000-42f7207a63d63607822f2017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-965e88496dc55d1d3a082017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-528bea85898c5bbee9742017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9400000000-25d222489152bbee48942017-06-28View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2900000000-f83a6dc29f504d8a27ea2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9400000000-f09039303c5f740d5e992021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdi-9000000000-5a1ebbe40df7d21e329f2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-ee9e9b8403f62cfc7fdf2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2900000000-5af433d114ee67df4fda2021-09-22View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0000873
DrugBank IDDB04120
Phenol Explorer Compound ID704
FoodDB IDFDB008861
KNApSAcK IDC00002660
Chemspider ID9564
KEGG Compound IDC06730
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link4-Methylcatechol
METLIN ID5834
PubChem Compound9958
PDB IDNot Available
ChEBI ID17254
References
General References
  1. Okuta A, Ohnishi K, Harayama S: Construction of chimeric catechol 2,3-dioxygenase exhibiting improved activity against the suicide inhibitor 4-methylcatechol. Appl Environ Microbiol. 2004 Mar;70(3):1804-10. doi: 10.1128/aem.70.3.1804-1810.2004. [PubMed:15006807 ]
  2. Scheline RR: Drug metabolism by intestinal microorganisms. J Pharm Sci. 1968 Dec;57(12):2021-37. doi: 10.1002/jps.2600571202. [PubMed:4974346 ]
  3. Fukuhara K, Ishikawa K, Yasuda S, Kishishita Y, Kim HK, Kakeda T, Yamamoto M, Norii T, Ishikawa T: Intracerebroventricular 4-methylcatechol (4-MC) ameliorates chronic pain associated with depression-like behavior via induction of brain-derived neurotrophic factor (BDNF). Cell Mol Neurobiol. 2012 Aug;32(6):971-7. doi: 10.1007/s10571-011-9782-2. Epub 2011 Dec 25. [PubMed:22198556 ]