3-Methylcatechol is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

with the formula A white solid, it is one of the isomers of

methylbenzenediol Methylbenzenediol, also known as dihydroxytoluene, may refer to: * 3-Methylcatechol (3-methylbenzene-1,2-diol or 2,3-dihydroxytoluene) * 4-Methylcatechol (4-methylbenzene-1,2-diol or 3,4-dihydroxytoluene) * 2-methylbenzene-1,3-diol * 4-methylbenz ...

. Being structurally related to

lignan The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a rol ...

s, it contributes to the aerosols generated by combustion of wood.

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. The isofunctional enzymes of catechol 1,2-dioxygenase from species of ''

Acinetobacter ''Acinetobacter'' is a genus of Gram-negative bacteria belonging to the wider class of Gammaproteobacteria. ''Acinetobacter'' species are oxidase-negative, exhibit twitching motility, and occur in pairs under magnification. They are important ...

'', ''

Pseudomonas ''Pseudomonas'' is a genus of Gram-negative bacteria belonging to the family Pseudomonadaceae in the class Gammaproteobacteria. The 348 members of the genus demonstrate a great deal of metabolic diversity and consequently are able to colonize a ...

'', ''

Nocardia ''Nocardia'' is a genus of weakly staining Gram-positive, catalase, catalase-positive, rod-shaped bacteria. It forms partially acid-fast beaded branching filaments (appearing similar to fungi, but being truly bacteria). It contains a total of 8 ...

'', ''

Alcaligenes ''Alcaligenes'' is a genus of Gram-negative, aerobic, rod-shaped bacteria in the order of Burkholderiales, family Alcaligenaceae. History The type species, ''A. faecalis'', was first isolated from stale beer by Johannes Petruschky in 1896. H ...

'' and ''

Corynebacterium ''Corynebacterium'' () is a genus of Gram-positive bacteria and most are aerobic. They are bacilli (rod-shaped), and in some phases of life they are, more specifically, club-shaped, which inspired the genus name ('' coryneform'' means "club-s ...

'' oxidize 3-methylcatechol according to both the intradiol and extradiol cleavage patterns. However, the enzyme preparations from '' Brevibacterium'' and ''

Arthrobacter ''Arthrobacter'' (from the Greek, "jointed small stick”) is a genus of bacterium, bacteria that is commonly found in soil. All species in this genus are Gram-positive obligate aerobes that are bacterial shape, rods during exponential growth and ...

'' have only the intradiol cleavage activity.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

Related compounds

The 3-methylcatechol

structural motif In a chain-like biological molecule, such as a protein or nucleic acid, a structural motif is a common three-dimensional structure that appears in a variety of different, evolutionarily unrelated molecules. A structural motif does not have t ...

is rare in

natural product A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical s ...

s. Known examples include calopin and a δ-

lactone Lactones are cyclic carboxylic esters. They are derived from the corresponding hydroxycarboxylic acids by esterification. They can be saturated or unsaturated. Lactones are formed by lactonization, the intramolecular esterification of the corresp ...

derivative, O-acetylcyclocalopin A, ''O''-acetylcyclocalopin A, which have been isolated from the fungus ''

Caloboletus calopus ''Caloboletus calopus'', commonly known as the bitter bolete, bitter beech bolete or scarlet-stemmed bolete, is a species of fungus in the bolete family. Christiaan Persoon first described ''Boletus calopus'' in 1801. Modern molecular phylo ...

''.

References

External links

phenol-explorer.eu
{{DEFAULTSORT:Methylcatechol, 3- Catechols Toluene derivatives