Record Information
Version1.0
Creation date2010-04-08 22:08:17 UTC
Update date2019-11-26 03:03:20 UTC
Primary IDFDB008861
Secondary Accession NumbersNot Available
Chemical Information
FooDB Name4-Methyl-1,2-benzenediol
Description4-Methylcatechol, 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, on average, in the highest concentration within a few different foods, such as arabica coffees (Coffea arabica), robusta coffees (Coffea canephora), and coffees (Coffea) and in a lower concentration in cocoa powder and beer. 4-Methylcatechol has also been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and eggplants (Solanum melongena). This could make 4-methylcatechol a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on 4-Methylcatechol.
CAS Number452-86-8
Structure
Thumb
Synonyms
SynonymSource
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
4-Methylcatecholdb_source
P-MethylcatecholChEBI
P-MethylpyrocatecholChEBI
Predicted Properties
PropertyValueSource
Water Solubility37.9 g/LALOGPS
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
Chemical FormulaC7H8O2
IUPAC name4-methylbenzene-1,2-diol
InChI IdentifierInChI=1S/C7H8O2/c1-5-2-3-6(8)7(9)4-5/h2-4,8-9H,1H3
InChI KeyZBCATMYQYDCTIZ-UHFFFAOYSA-N
Isomeric SMILESCC1=CC=C(O)C(O)=C1
Average Molecular Weight124.1372
Monoisotopic Molecular Weight124.0524295
Classification
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:

Foods
  • Cocoa and cocoa products
  • Grains:

    Nuts and legumes:

    Fruits and vegetables:

    Fats and oils:

    Beverages:

    Physico-Chemical Properties - Experimental
    Physico-Chemical Properties - Experimental
    PropertyValueReference
    Physical stateSolid
    Physical DescriptionNot Available
    Mass CompositionC 67.73%; H 6.50%; O 25.78%DFC
    Melting PointNot Available
    Boiling PointBp20 143-146°DFC
    Experimental Water SolubilityNot Available
    Experimental logPNot Available
    Experimental pKaNot Available
    Isoelectric pointNot Available
    ChargeNot Available
    Optical RotationNot Available
    Spectroscopic UV DataNot Available
    DensityNot Available
    Refractive IndexNot Available
    Spectra
    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-1900000000-9045a710867168d6cc51Spectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-0e20b47a091c0b3e39abSpectrum
    MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-0e20b47a091c0b3e39abSpectrum
    MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-7db9fcc9e56ad8a39080Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-014j-9200000000-f6f538341319fcc5433bSpectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-0900000000-97cd131a887e2f870186Spectrum
    MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-014i-9000000000-6981a2924f054e884c5cSpectrum
    MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-00di-0900000000-0aaf237b7039ed11a1d7Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-0553-9000000000-fe5754c269058c591febSpectrum
    MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0006-9000000000-c1c0f17738a12823f96dSpectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-2900000000-e5f3b6d9329514c202a8Spectrum
    MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-d5abc716689493ede24fSpectrum
    MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-6bd82a87c9fe3a5ac3f7Spectrum
    MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-03dj-9000000000-5833215eaa6163ad44f4Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-efa52ff0e22aa918c832Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-1813508ce877db8f3b51Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9200000000-42f7207a63d63607822fSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-965e88496dc55d1d3a08Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-528bea85898c5bbee974Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9400000000-25d222489152bbee4894Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-2900000000-f83a6dc29f504d8a27eaSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-9400000000-f09039303c5f740d5e99Spectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gdi-9000000000-5a1ebbe40df7d21e329fSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-ee9e9b8403f62cfc7fdfSpectrum
    Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-2900000000-5af433d114ee67df4fdaSpectrum
    NMR
    TypeDescriptionView
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    1D NMR13C NMR SpectrumSpectrum
    1D NMR1H NMR SpectrumSpectrum
    2D NMR[1H,13C] 2D NMR SpectrumSpectrum
    ChemSpider ID9564
    ChEMBL IDNot Available
    KEGG Compound IDC06730
    Pubchem Compound ID9958
    Pubchem Substance IDNot Available
    ChEBI IDNot Available
    Phenol-Explorer ID704
    DrugBank IDDB04120
    HMDB IDHMDB00873
    CRC / DFC (Dictionary of Food Compounds) IDDZP92-X:DZP92-X
    EAFUS IDNot Available
    Dr. Duke IDNot Available
    BIGG IDNot Available
    KNApSAcK IDNot Available
    HET IDMCT
    Food Biomarker OntologyNot Available
    VMH IDNot Available
    Flavornet IDNot Available
    GoodScent IDNot Available
    SuperScent IDNot Available
    Wikipedia IDNot Available
    Phenol-Explorer Metabolite IDNot Available
    Duplicate IDSNot Available
    Old DFC IDSNot Available
    Associated Foods
    FoodContent Range AverageReference
    FoodReference
    Biological Effects and Interactions
    Health Effects / BioactivitiesNot Available
    EnzymesNot Available
    PathwaysNot Available
    MetabolismNot Available
    BiosynthesisNot Available
    Organoleptic Properties
    FlavoursNot Available
    Files
    MSDSshow
    References
    Synthesis ReferenceNot Available
    General ReferenceNot Available
    Content Reference— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.