3-Methylcatechol

Last updated

Contents

3-Methylcatechol
2,3-Dihydroxytoluol.svg
Names
Preferred IUPAC name
3-Methylbenzene-1,2-diol
Other names
2,3-Dihydroxytoluene
3-Methylpyrocatechol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.975 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C7H8O2/c1-5-3-2-4-6(8)7(5)9/h2-4,8-9H,1H3
    Key: PGSWEKYNAOWQDF-UHFFFAOYSA-N
  • CC1=C(C(=CC=C1)O)O
Properties
C7H8O2
Molar mass 124.139 g·mol−1
Appearancewhite solid
Density g/cm3
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).

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 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]

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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.