4-Methylcatechol

4-Methylcatechol is an organic compound with the formula CH₃C₆H₃(OH)₂ A white solid, it is one of the isomers of methylbenzenediol.

4-Methylcatechol

Names
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
CAS Number	452-86-8 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:17254
ChemSpider	9564
ECHA InfoCard	100.006.559
PubChem CID	9958
UNII	12GLI7JGB3 Y
CompTox Dashboard (EPA)	DTXSID5020861
SMILES CC1=CC(=C(C=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

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

Calone, a derivative of 4-methylcatechol, is known in the fragrance industry as "watermelon ketone" for its distinctive odor.^[3]

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]

See also

• Dihydroxytoluene