Article · Wikipedia archive · Last revised Jun 11, 2026

3-Methylcatechol

3-Methylcatechol is an organic compound with the formula CH3C6H3(OH)2 A white solid, it is one of the isomers of methylbenzenediol. Being structurally related to lignans, it contributes to the aerosols generated by combustion of wood.

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Jun 11, 2026
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3-Methylcatechol
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Names
Preferred IUPAC name
3-Methylbenzene-1,2-diol
Other names
2,3-Dihydroxytoluene
3-Methylpyrocatechol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.975
UNII
  • InChI=1S/C7H8O2/c1-5-3-2-4-6(8)7(5)9/h2-4,8-9H,1H3
    Key: PGSWEKYNAOWQDF-UHFFFAOYSA-N
  • CC1=C(C(=CC=C1)O)O
Properties
C7H8O2
Molar mass 124.139 g·mol−1
Appearance white solid
Density g/cm3
Melting point 68 °C (154 °F; 341 K)
Boiling point 241 °C (466 °F; 514 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

3-Methylcatechol is an organic compound with the formula CH3C6H3(OH)2 A white solid, it is one of the isomers of methylbenzenediol. Being structurally related to lignans, it contributes to the aerosols generated by combustion of wood.1

Metabolism

The enzyme 1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate dehydrogenase uses 1,2-dihydroxy-6-methylcyclohexa-3,5-dienecarboxylate and NAD+ to produce 3-methylcatechol, NADH and CO2.2

The isofunctional enzymes of catechol 1,2-dioxygenase from species of Acinetobacter, Pseudomonas, Nocardia, Alcaligenes and Corynebacterium oxidize 3-methylcatechol according to both the intradiol and extradiol cleavage patterns. However, the enzyme preparations from Brevibacterium and Arthrobacter have only the intradiol cleavage activity.3

The 3-methylcatechol structural motif is rare in natural products. Known examples include calopin and a δ-lactone derivative, O-acetylcyclocalopin A|O-acetylcyclocalopin A, which have been isolated from the fungus Caloboletus calopus.4

References

References

  1. Rogge WF, Hildemann LM, Mazurek MA, Cass GR, Simoneit, BRT (1998). "Sources of Fine Organic Aerosol. 9. Pine, Oak, and Synthetic Log Combustion in Residential Fireplaces". Environmental Science & Technology. 32 (1): 13–22. Bibcode:1998EnST...32...13R. doi:10.1021/es960930b.
  2. Higson FK, Focht DD (1992). "Degradation of 2-methylbenzoic acid by Pseudomonas cepacia MB2". Appl. Environ. Microbiol. 58 (1): 194–200. Bibcode:1992ApEnM..58..194H. doi:10.1128/aem.58.1.194-200.1992. PMC 195191. PMID 1371658.
  3. Extradiol Cleavage of 3-Methylcatechol by Catechol 1,2-Dioxygenase from Various Microorganisms. C. T. Hou, R. Patel and M. O. Lillard, Appl. Environ. Microbiol., March 1977, volume 33, issue 3, pages 725-727 (abstract)
  4. Hellwig, V., Dasenbrock, J., Gräf, C., Kahner, L., Schumann, S., Steglich, W. (2002). "Calopins and cyclocalopins – Bitter principles from Boletus calopus and related mushrooms". European Journal of Organic Chemistry. 2002 (17): 2895–904. doi:10.1002/1099-0690(200209)2002:17<2895::AID-EJOC2895>3.0.CO;2-S.
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