3-Methoxycatechol

SLIGHTLY BEIGE TO LIGHT BROWN CRYSTALLINE SOLID

3-Methoxycatechol is used to prepare polyphenolic deoxybenzoins as potential antioxidants and tyrosinase inhibitors.

ChEBI: 3-methoxycatechol is a member of the class of catechols that is catechol in which a hydrogen that is ortho to one of the hydroxy groups has been replaced by a methoxy group. It displays agonistic activity against G protein-coupled receptor 35 (GPR35). It has a role as a G-protein-coupled receptor agonist. It is a member of catechols and an aromatic ether. It is functionally related to a pyrogallol.

2,3-Dihydroxyanisole is synthesised using 2-hydroxy-3-methoxybenzaldehyde as a raw material by chemical reaction. The specific synthesis steps are as follows:
To a solution of 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) (20.3 g,0.134 mole)in aqueous sodium hydroxide (2N,66.6 ml,0.133 mole)is added dropwise hydrogen peroxide (6%,95 ml,0.167 mole) during 1 hr at 40-45(the solution is cooled if necessary).After the reaction is over,the reaction mixture is allowed to cool to room temperature.It is saturated with sodium chloride and then extracted with ether (3 x 70 ml).The ether solution is dried (sodium sulphate)and distilled.The residual product is distilled and the fraction boiling at 136-38/22 mm is collected.Yield 11 g (58.8%)(lit.b.p.136-38/22 mm).