Clostebol

Description

Clostebol (Item No. 21168) is an analytical reference standard that is categorized as an androgenic anabolic steroid. Clostebol is a chlorinated form of testosterone (Item Nos. 15645 | ISO60154) that has been used as an athletic performance enhancer and to fatten cattle. It is also detectible in urine. Formulations containing clostebol have been used to treat osteoporosis, anorexia, and certain types of liver disease. Clostebol is regulated as a Schedule III compound in the United States. This product is intended for research and forensic applications.

Uses

Clostebol is an anabolic steroid. This is a controlled substance.

Definition

ChEBI: Clostebol is a 3-hydroxy steroid. It has a role as an androgen.

Synthesis

Clostebol can be synthesized from 4,5-Epoxy-androstan-17β-ol-3-one by acidification with 25% hydrochloric acid.
Procedure：8.50 g epoxide (4,5-Epoxy-androstan-17β-ol-3-one) was dissolved in 150 ml Acetone and treated with 14 ml of 25% hydrochloric acid. An immediate color shift of the reaction mixture from light yellow to deep blue can be observed. After stirring for 30 h at room temperature, a complete conversion of the epoxide (4,5-Epoxy-androstan-17β-ol-3-one) can be monitored by TLC. The reaction mixture was diluted with 400 ml water, leading to the formation of a blue-black solid precipitating from the solution. After evaporation of acetone, the remaining aqueous solution was extracted several times with 200 ml dichloromethane. The combined organic extracts were washed with saturated sodium bicarbonate solution and sodium chloride solution before drying over magnesium sulfate. The crude product was chromatographed on silica gel by using hexane-ethyl acetat (1:1) and followed by a recrystallization from acetone. The isolated product Clostebol was obtained as yellowish crystals (4.50 g; 51%).