Butantrone

Originator

Butantrone,Onbio Inc.

Manufacturing Process

To a solution of 56.6 g (0.25 mol) of anthralin in 1750 ml of absolute toluene and 27.3 ml of pyridine, 31.5 ml (0.3 mol) of butyryl chloride was added with stirring over 30 min at room temperature. The reaction mixture was then heated to 85°C for 1 hour. After this mixture had recooled to room temperature, 27.3 ml of pyridine and 31.5 ml of butyryl chloride were again added. The suspension obtained was then heated to 85-90°C for 1 hour. The precipitated pyridinium hydrochloride was eliminated by filtration then washed with toluene. The toluene filtrates were concentrated to around 500 ml under reduced pressure, washed several times with water then dried over magnesium sulfate. The product was then fractionated by chromatography on silica gel, using toluene and then a mixture of toluene and ethyl acetate as the mobile phase. The different fractions containing the 1,8-dihydroxy-10-(1- oxobutyl)-9(10H)-anthracenone were then concentrated and recrystallized from a toluene-hexane mixture. In this way 25 g of yellow crystals of 1,8- dihydroxy-10-(1-oxobutyl)-9(10H)-anthracenone having a melting point of 138°C was obtained.

Therapeutic Function

Antipsoriatic

Hazard

A poison by ingestion. A mild skin irritant.

Safety Profile

A poison by ingestion. A mild skin irritant. Mutation data reported. When heated to decomposition it emits acrid smoke and irritating vapors.