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]

Related compounds

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]

gollark: The issues I think are most problematic are just companies being able to influence governance, and I'm not really sure what to do about that. Perhaps just have strong norms about having the government not do much.

gollark: You'd need a way to somehow be able to have some of the profit from new fundamental stuff go back to its original investors.

gollark: Probably some kind of long-term research investment things?

gollark: I think with better coordinating/financial structures in place we could probably have better encouragement to do fundamental stuff.

gollark: And the government funding means we still get that, so it seems fine.

References

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.

External links

phenol-explorer.eu

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.

[1] 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.

[2] 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_2002-3] 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.