Chemistry:3-Methylcatechol
3-Methylcatechol is an organic compound with the formula CH
3C
6H
3(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]
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
- ↑ "Sources of Fine Organic Aerosol. 9. Pine, Oak, and Synthetic Log Combustion in Residential Fireplaces". Environmental Science & Technology 32 (1): 13–22. 1998. doi:10.1021/es960930b. Bibcode: 1998EnST...32...13R.
- ↑ "Degradation of 2-methylbenzoic acid by Pseudomonas cepacia MB2". Appl. Environ. Microbiol. 58 (1): 194–200. 1992. doi:10.1128/aem.58.1.194-200.1992. PMID 1371658. Bibcode: 1992ApEnM..58..194H.
- ↑ 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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