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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:03:26 UTC
HMDB IDHMDB00873
Secondary Accession NumbersNone
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(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 KeyInChIKey=ZBCATMYQYDCTIZ-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
ClassBenzene and substituted derivatives
Sub ClassPhenols and derivatives
Direct ParentCatechols
Alternative Parents
Substituents
  • P-cresol
  • M-cresol
  • 1,2-diphenol
  • Toluene
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity35.06 m3·mol-1ChemAxon
Polarizability12.82 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
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
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Feces
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot Available
Normal
  • Not Applicable
details
FecesDetected but not QuantifiedNot ApplicableAdult (>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. [6890513 ]
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound ID704
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB008861
KNApSAcK IDNot Available
Chemspider ID9564
KEGG Compound IDC06730
BioCyc ID4-METHYLCATECHOL
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00873
Metagene LinkHMDB00873
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. [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. [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. [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. [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. [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. [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. [15006807 ]
  8. Shen Y: In vitro cytotoxicity of BTEX metabolites in HeLa cells. Arch Environ Contam Toxicol. 1998 Apr;34(3):229-34. [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. [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. [22198556 ]