3-Methylcatechol Explained

3-Methylcatechol is an organic compound with the formula 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]

External links

• phenol-explorer.eu

Notes and References

1. 10.1021/es960930b . Sources of Fine Organic Aerosol. 9. Pine, Oak, and Synthetic Log Combustion in Residential Fireplaces . 1998 . Environmental Science & Technology . 32 . 1 . 13–22 . 1998EnST...32...13R . Rogge WF, Hildemann LM, Mazurek MA, Cass GR, Simoneit, BRT .
2. Higson FK, Focht DD . 1992 . Degradation of 2-methylbenzoic acid by Pseudomonas cepacia MB2 . Appl. Environ. Microbiol. . 58 . 194–200 . 1371658 . 1 . 10.1128/aem.58.1.194-200.1992 . 195191 . 1992ApEnM..58..194H .
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. . Calopins and cyclocalopins – Bitter principles from Boletus calopus and related mushrooms . European Journal of Organic Chemistry . 2002 . 2002 . 17 . 2895–904 . 10.1002/1099-0690(200209)2002:17<2895::AID-EJOC2895>3.0.CO;2-S.