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
