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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:19:47 UTC
HMDB IDHMDB0000873
Secondary Accession Numbers
  • HMDB00873
Metabolite Identification
Common Name4-Methylcatechol
Description4-methylcatechol is a metabolite of homoprotocatechuic acid. It is both a substrate and a suicide inhibitor of Catechol 2,3-dioxygenase [EC 1.3.11.2]. (PMID 15006807). 4-methylcatechol is known to induce the production of brain-derived neurotrophic factor (BDNF). Recent studies have suggested that a lack of brain-derived neurotrophic factor (BDNF) in the limbic system may cause neuropathic pain. (PMID: 22198556).
Structure
Thumb
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 Weight124.1372
Monoisotopic Molecular Weight124.0524295
IUPAC Name4-methylbenzene-1,2-diol
Traditional Name4-methyl-1,2-benzenediol
CAS Registry Number452-86-8
SMILES
CC1=CC=C(O)C(O)=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
DescriptionThis compound belongs to the class of organic compounds known as catechols. These 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

Biological location:

  Biofluid and excreta:

Source:

  Biological:

    Plant:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

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
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014i-1930000000-6225053efa0739efca3dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-4900000000-2d8d69f64905f6f9396eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0udj-3940000000-d5331c4c752130a85084View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a6r-1900000000-9045a710867168d6cc51View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-004i-9000000000-0e20b47a091c0b3e39abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-004i-9000000000-0e20b47a091c0b3e39abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-00di-0900000000-7db9fcc9e56ad8a39080View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-efa52ff0e22aa918c832View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-1813508ce877db8f3b51View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0v00-9200000000-42f7207a63d63607822fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-965e88496dc55d1d3a08View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1900000000-528bea85898c5bbee974View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fu-9400000000-25d222489152bbee4894View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    FecesDetected but not Quantified Adult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified7.814 +/- 1.128 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    FecesDetected and Quantified14.339 nmol/g of fecesAdult (>18 years old)Both
    Normal
    details
    UrineDetected and Quantified1.8 +/- 1.2 umol/mmol creatinineAdult (>18 years old)Both
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified3.6 +/- 1.5 umol/mmol creatinineAdult (>18 years old)Male
    Smoking
    details
    Associated Disorders and Diseases
    Disease References
    Smoking
    1. Carmella SG, La Voie EJ, Hecht SS: Quantitative analysis of catechol and 4-methylcatechol in human urine. Food Chem Toxicol. 1982 Oct;20(5):587-90. [PubMed:6890513 ]
    Associated OMIM IDsNone
    DrugBank IDDB04120
    Phenol Explorer Compound ID704
    FoodDB IDFDB008861
    KNApSAcK IDC00002660
    Chemspider ID9564
    KEGG Compound IDC06730
    BioCyc ID4-METHYLCATECHOL
    BiGG IDNot Available
    Wikipedia Link4-Methylcatechol
    METLIN ID5834
    PubChem Compound9958
    PDB IDMCT
    ChEBI ID17254
    References
    Synthesis ReferenceLiang, Zesheng; Zhang, Ying; Wu, Baojun; Zhang, Mingsen; Wang, Xiu'en. Preparation of 4-methylcatechol with good yield and selectivity. Faming Zhuanli Shenqing Gongkai Shuomingshu (2001), 6 pp.
    Material Safety Data Sheet (MSDS)Download (PDF)
    General References
    1. Baba S, Furuta T, Horie M, Nakagawa H: Studies on drug metabolism by use of isotopes XXVI: Determination of urinary metabolites of rutin in humans. J Pharm Sci. 1981 Jul;70(7):780-2. [PubMed:7264927 ]
    2. Alanko J, Riutta A, Holm P, Mucha I, Vapaatalo H, Metsa-Ketela T: Modulation of arachidonic acid metabolism by phenols: relation to their structure and antioxidant/prooxidant properties. Free Radic Biol Med. 1999 Jan;26(1-2):193-201. [PubMed:9890654 ]
    3. Carmella SG, La Voie EJ, Hecht SS: Quantitative analysis of catechol and 4-methylcatechol in human urine. Food Chem Toxicol. 1982 Oct;20(5):587-90. [PubMed:6890513 ]
    4. Glasser G, Graefe EU, Struck F, Veit M, Gebhardt R: Comparison of antioxidative capacities and inhibitory effects on cholesterol biosynthesis of quercetin and potential metabolites. Phytomedicine. 2002 Jan;9(1):33-40. [PubMed:11924762 ]
    5. Ridder L, Briganti F, Boersma MG, Boeren S, Vis EH, Scozzafava A, Veeger C, Rietjens IM: Quantitative structure/activity relationship for the rate of conversion of C4-substituted catechols by catechol-1,2-dioxygenase from Pseudomonas putida (arvilla) C1. Eur J Biochem. 1998 Oct 1;257(1):92-100. [PubMed:9799107 ]
    6. Capasso R, Evidente A, Schivo L, Orru G, Marcialis MA, Cristinzio G: Antibacterial polyphenols from olive oil mill waste waters. J Appl Bacteriol. 1995 Oct;79(4):393-8. [PubMed:7592132 ]
    7. 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. [PubMed:15006807 ]
    8. Shen Y: In vitro cytotoxicity of BTEX metabolites in HeLa cells. Arch Environ Contam Toxicol. 1998 Apr;34(3):229-34. [PubMed:9504968 ]
    9. Graefe EU, Veit M: Urinary metabolites of flavonoids and hydroxycinnamic acids in humans after application of a crude extract from Equisetum arvense. Phytomedicine. 1999 Oct;6(4):239-46. [PubMed:10589442 ]
    10. 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 ]