4-Methylcatechol
Chemical compound
From Wikipedia, the free encyclopedia
4-Methylcatechol is an organic compound with the formula CH3C6H3(OH)2 A white solid, it is one of the isomers of methylbenzenediol.
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| Names | |
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| Preferred IUPAC name
4-Methylbenzene-1,2-diol | |
| Other names
4-Methyl-1,2-dihydroxybenzene 3,4-Dihydroxytoluene Homocatechol 4-Methyl-1,2-benzenediol Homopyrocatechol p-Methylcatechol | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| DrugBank | |
| ECHA InfoCard | 100.006.559 |
| EC Number |
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| KEGG | |
PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C7H8O2 | |
| Molar mass | 124.139 g·mol−1 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H302, H312, H315, H319, H335 | |
| P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Metabolism
The enzyme cis-1,2-dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate dehydrogenase uses cis-1,2-dihydroxy-4-methylcyclohexa-3,5-diene-1-carboxylate and NAD(P)+ to produce 4-methylcatechol, NADH, NADPH and CO2.[1]
Related compounds
Members of the monocot subfamily Amaryllidoideae present a unique type of alkaloids, the norbelladine alkaloids, which are 4-methylcatechol derivatives combined with tyrosine. They are responsible for the poisonous properties of a number of the species. Over 200 different chemical structures of these compounds are known, of which 79 or more are known from Narcissus alone.[2]
Production and occurrence
The brand of low-temperature coke used as a smokeless fuel Coalite obtains homocatechol from ammoniacal liquor by solvent extraction, distillation and crystallisation.[citation needed]
Being structurally related to lignans, it is contributes to the aerosol generate by combustion of wood.[4]
It is a component of castoreum, the exudate from the castor sacs of the mature beaver.[5]