19-Norandrostenediol

Originator

19-Norandrostenediol,Epochem Co., Ltd.

Uses

Bolandiol is a unique anabolic steroid with androgenic, estrogenic, and progestational activities.

Definition

ChEBI: Bolandiol is a 3beta-hydroxy steroid that is estr-4-ene substituted by a beta-hydroxy group at positions 3 and 17. It is a synthetic anabolic steroid that is used as a dietary supplement by athletes to enhance performance. It has a role as a nutraceutical and a prohormone. It is a 17beta-hydroxy steroid, an anabolic androgenic steroid, a 3beta-hydroxy steroid and a diol. It derives from a hydride of an estrane.

Manufacturing Process

To a suspension of 6 parts of lithium aluminum hydride in 2100 parts of ether there are added, with stirring, 7.2 parts of 19-nortestosterone in 700 parts of ether. The mixture is stirred with heating on the steam bath for 45 min, after which the unreacted lithium aluminum hydride is decomposed by addition of acetone. The mixture is diluted with water and the organic layer is separated and washed with water and saturated aqueous sodium chloride solution. After drying over anhydrous sodium sulfate, the ether solution is evaporated under vacuum and the residue is dissolved in benzene and thus applied to a chromatography column containing 760 parts of silica gel. The column is developed with benzene and then with 5 and 10% solutions of ethyl acetate in benzene. Further elution with a 15% solution of ethyl acetate in benzene and concentration of the eluate yields a residue which is recrystallized from acetone and water, ethyl acetate and petroleum ether, and again from acetone and water to yield the 4-estrene-3β,17β-diol, melting point 169°-172°C.

Therapeutic Function

Anabolic