3-Methylcatechol

3-Methylcatechol

Names
Preferred IUPAC name 3-Methylbenzene-1,2-diol
Other names 2,3-Dihydroxytoluene 3-Methylpyrocatechol
Identifiers
CAS Number	488-17-5^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:18404
ChemSpider	333
ECHA InfoCard	100.006.975
PubChem CID	340
UNII	0HUZ4Q9R8C^Y
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
Appearance	white solid
Density	g/cm^3
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). Infobox references

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 is contributes to the aerosol generate 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]

Related compounds

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

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.

External links

• phenol-explorer.eu