19793-20-5 Usage
Originator
19-Norandrostenediol,Epochem Co., Ltd.
Uses
Bolandiol is a unique anabolic steroid with androgenic, estrogenic, and progestational activities.
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
Check Digit Verification of cas no
The CAS Registry Mumber 19793-20-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,7,9 and 3 respectively; the second part has 2 digits, 2 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 19793-20:
(7*1)+(6*9)+(5*7)+(4*9)+(3*3)+(2*2)+(1*0)=145
145 % 10 = 5
So 19793-20-5 is a valid CAS Registry Number.
InChI:InChI=1/C18H28O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,12-17,19-20H,2-9H2,1H3/t12-,13?,14?,15?,16?,17-,18-/m0/s1
19793-20-5Relevant articles and documents
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Hartman
, p. 5151,5153 (1955)
-
An easy stereoselective synthesis of 5(10)-estrene-3β,17α-diol, a biological marker of pregnancy in the mare
Balssa, Frédéric,Fischer, Michael,Bonnaire, Yves
, p. 1 - 4 (2014/06/09)
5(10)-Estrene-3β,17α-diol is an essential reference material for doping analysis in horse-racing laboratories. It is used to detect misuse, for doping purpose, of the pregnancy status in the mare. Its stereoselective synthesis from 17β-estradiol-3-methyl ether (prepared from estrone or 17β-estradiol) was performed in four steps: (1) Mitsunobu inversion of the 17β-alcohol; (2) Birch reduction of the aromatic ring; (3) stereoselective reduction of the 3-ketone via Noyori asymmetric transfer hydrogenation; (4) chemoenzymatic purification.
Facial selectivity in the hydroboration of androst-4-enes
Hanson, James R.,Hitchcock, Peter B.,Liman, Mansur D.,Naragatnam, Sivajini
, p. 2183 - 2188 (2007/10/02)
In the absence of an allylic hydroxy group, the stereochemistry of hydroboration of an androst-4-ene is determined by the presence and stereochemistry of the C-10 methyl group.Allylic hydroxy groups at C-3 direct the hydroboration/oxidation to the anti-face.In the case of the 3α-alcohol, this effect is in opposition to the normal hydration from the α-face of the steroid and leads to the 4β-alcohol.The stereochemistry of 4β,17β-diacetoxy-19-nor-5β-androstane was established by X-ray crystallography.
