4-Ethylresorcinol

Description

4-Ethylresorcinol is a derivative of resorcinol, which acts as a substrate for tyrosinase. 4-Ethylresorcinol has hypopigmentation effects.4-Ethylresorcinol attenuates the mRNA and protein expression of tyrosinase-related protein (TRP)-2, and has an antioxidant effect through the inhibition of lipid peroxidation. 4-Ethylresorcinol is a derivative of resorcinol, which acts as a substrate for tyrosinase. 4-Ethylresorcinol is a derivative of resorcinol.

Chemical Properties

slightly beige crystalline powder

Uses

It is employed as an active pharmaceutical intermediate.

Definition

ChEBI: 4-Ethylresorcinol is a member of resorcinols.

Synthesis Reference(s)

Synthetic Communications, 15, p. 1315, 1985 DOI: 10.1080/00397918508077280

Synthesis

The synthesis of 4-Ethylresorcinol is as follows:
In a three necked round bottom flask (equipped with a condensor, additional funnel and mechanical stirrer) was added 15.2 g of a combination of Raney Nickel and Ni supported on silica. (50: 50). 100 ml of a mixture of 50: 50 ethanol: water was added and the reaction was heated at reflux conditions. 15.2 g of 2,4-dihydroxy acetophenone in 100 ml of water: ethanol and 10 ml of acetic acid was placed in the additional funnel and slowly added to the mixture (dropwise). The reaction was filtered through a milipore filter to give a pale yellow solution. Concentration of this solution in vacuo gave a solid. This solid was crystalized from 1,2-dichloroethane to give 4-ethyl resorcinol in 80% isolated yield.