3-Methylcatechol
{{cs1 config|name-list-style=vanc}}
{{chembox
| Name = 3-Methylcatechol
| ImageFile = 2,3-Dihydroxytoluol.svg
| ImageSize = 120 px
| PIN = 3-Methylbenzene-1,2-diol
| OtherNames = 2,3-Dihydroxytoluene
3-Methylpyrocatechol
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 488-17-5
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 0HUZ4Q9R8C
| ChEMBL_Ref =
| ChEMBL =
| ChemSpiderID_Ref =
| ChemSpiderID = 333
| ChEBI_Ref =
| ChEBI = 18404
| DrugBank_Ref =
| DrugBank =
| InChI =
| InChIKey =
| KEGG_Ref =
| KEGG =
| PubChem = 340
| SMILES = CC1=C(C(=CC=C1)O)O
| StdInChI_Ref =
| StdInChI = 1S/C7H8O2/c1-5-3-2-4-6(8)7(5)9/h2-4,8-9H,1H3
| StdInChIKey_Ref =
| StdInChIKey = PGSWEKYNAOWQDF-UHFFFAOYSA-N
}}
|Section2={{Chembox Properties
| C=7 | H=8 | O=2
| Appearance = white solid
| Density = g/cm3
| MeltingPtC = 68
| BoilingPtC = 241
| Solubility =
}}
|Section7={{Chembox Hazards
| ExternalSDS =
| FlashPt =
| NFPA-H =
| NFPA-F =
| NFPA-R =
}}
}}
3-Methylcatechol is an organic compound with the formula {{chem2|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.{{cite journal |doi=10.1021/es960930b |title=Sources of Fine Organic Aerosol. 9. Pine, Oak, and Synthetic Log Combustion in Residential Fireplaces |date=1998 |journal=Environmental Science & Technology |volume=32 |issue=1 |pages=13–22 |bibcode=1998EnST...32...13R | vauthors = Rogge WF, Hildemann LM, Mazurek MA, Cass GR, Simoneit, BRT }}
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.{{cite journal | vauthors = Higson FK, Focht DD | date = 1992 | title = Degradation of 2-methylbenzoic acid by Pseudomonas cepacia MB2 | journal = Appl. Environ. Microbiol. | volume = 58 | pages = 194–200 | pmid = 1371658 | issue = 1 | doi = 10.1128/aem.58.1.194-200.1992 | pmc = 195191 | bibcode = 1992ApEnM..58..194H }}
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.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 ([http://aem.asm.org/content/33/3/725 abstract])
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.{{cite journal |author =Hellwig, V. |author2 =Dasenbrock, J. |author3 =Gräf, C. |author4 =Kahner, L. |author5 =Schumann, S. |author6 =Steglich, W. |title=Calopins and cyclocalopins – Bitter principles from Boletus calopus and related mushrooms |journal=European Journal of Organic Chemistry |year=2002 |volume=2002 |issue=17 |pages=2895–904 |doi=10.1002/1099-0690(200209)2002:17<2895::AID-EJOC2895>3.0.CO;2-S}}
References
{{reflist}}
External links
- [http://www.phenol-explorer.eu/compounds/703 phenol-explorer.eu]
{{DEFAULTSORT:Methylcatechol, 3-}}