3-Methylcatechol

3-Methylcatechol
Names
	IUPAC name 3-Methylbenzene-1,2-diol
	Other names 2,3-Dihydroxytoluene; 3-Methylpyrocatechol; Dihydroxytoluene
Identifiers
CAS Number	488-17-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:18404;
ChemSpider	333;
ECHA InfoCard	100.006.975
PubChem CID	340;
UNII	0HUZ4Q9R8C ;
CompTox Dashboard (EPA)	DTXSID9060071 ;
	InChI InChI=1S/C7H8O2/c1-5-3-2-4-6(8)7(5)9/h2-4,8-9H,1H3 Key: PGSWEKYNAOWQDF-UHFFFAOYSA-N;
	SMILES CC1=C(C(=CC=C1)O)O;
Properties
Chemical formula	C7H8O2
Molar mass	124.139 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	Infobox references

3-Methylcatechol is a chemical compound.

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.[1]

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.[2]

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

Higson FK, Focht DD (1992). "Degradation of 2-methylbenzoic acid by Pseudomonas cepacia MB2". Appl. Environ. Microbiol. 58 (1): 194–200. PMC 195191. PMID 1371658.
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)
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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