58-19-5 Usage
Chemical Properties
White Solid
Originator
Drolban,Lilly,US,1961
Uses
Synthetic estrogen antagonist. Antineoplastic.
Controlled substance.
Manufacturing Process
A suspension of 10 grams of dihydrotestosterone in 500 cc of anhydrous
benzene free of thiophene was mixed with10 cc of ethyl formate and 3 grams
of sodium hydride and the mixture was stirred for 5 hours under an
atmosphere of nitrogen and at a temperature of approximately 25°C. The
resulting suspension was filtered, the resulting mixture of the sodium salt of
the hydroxymethylene compound and the excess of sodium hydride was
washed with benzene and dried. This mixture was slowly added to a
vigorously stirred solution of 20 cc of concentrated hydrochloric acid in 500 cc
of water, and the stirring was continued for 30 minutes at the end of which
the precipitate was collected and well washed with distilled water. After drying
in vacuo, there was obtained 9.7 grams of 2-hydroxymethylenedihydrotestosterone.A mixture of 1 gram of 2-hydroxymethylene-dihydrotestosterone, 10 cc of
pyridine and 2 cc of propionic anhydride was allowed to react at room
temperature for 16 hours and then poured into water. The resulting
suspension was heated for 1 hour on the steam bath to hydrolyze the excess
of propionic anhydride, cooled and extracted with methylene dichloride. The
extract was consecutively washed with dilute hydrochloric acid, sodium
bicarbonate solution and water, dried over anhydrous sodium sulfate and
evaporated to dryness under vacuum. There was thus obtained the
dipropionate of 2-hydroxymethylenedihydrotestosterone which was treated
with hydrogen, in methanol solution.When the uptake of hydrogen ceased, the catalyst was filtered and the
solution was evaporated to dryness under vacuum. The residue was dissolved
in a mixture of benzene-hexane, transferred to a chromatographic column
with neutral alumina and the product was eluted with mixtures of benzenehexane, gradually increasing the proportion of benzene in the mixture.
Crystallization of the eluates from acetone-hexane yielded the propionate of
2α-methyldihydrotestosterone.
Brand name
Drolban (Lilly).
Therapeutic Function
Cancer chemotherapy
Synthesis
Drostanolone is prepared by this “one-pot-reaction”-step the conversion to the 1α-methyl-group is performed simultaneously with the cleavage of the protective group at the 17β-alcohol: 10.60 g Hydroxymethylene-precusor 2-Hydroxymethylene-androstan-17β-((tetrahydro-2H-pyran-2-yl)oxy)-3-one was nearly dissolved in 800 ml ethanol at 55°C. This
solution was hydrogenated in a pressure vessel (Parr reactor) with 6.00 g palladium on charcoal
(5%) at 4 bar and room temperature for 24 h. The mixture was filtered twice through paper and
the corresponding ethanol solution was evaporated, to yield 9.50 g colorless oil, still contains
traces of charcoal and ethanol. The crude product was purified by column chromatography on
silica gel by using hexane-ethyl acetate (8:2) as an eluent, to afford 5.45 g purified Drostanolone as
a colorless solid (69%) . MS (ESI+):
m/z = 304.96 (calculated MW: 304.47 g/mol)
Rf: 0.35, hexane/ethyl acetate 7:3, visualized by Seebach derivatization reagent.
1
H NMR(300 MHz, DMSO-d6) : δ 4.42 (d, 1 H, OH), 3.42 (m, 1H, HCHOH), 3.32 (s, 1H, CH),
2.37 (t, 1 H, CH), 1.99 (dd, 1 H, ), 1.84 (dd, 1H), 1.78 – 1.84 (m, 1H), 1.72 (m, 1H), 1.61 (m,
1H), 1.22-1.58 (m, 8H), 1.08 – 1.22 (m, 1H), 1.03 (s, 3H, CH3), 0.76-1.01 (m + d, 7H, 2α-CH3
+X), 0.65 – 0.72 (m, 1H), 0.64 (s, 3H, CH3).
Check Digit Verification of cas no
The CAS Registry Mumber 58-19-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 8 respectively; the second part has 2 digits, 1 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 58-19:
(4*5)+(3*8)+(2*1)+(1*9)=55
55 % 10 = 5
So 58-19-5 is a valid CAS Registry Number.
InChI:InChI=1/C20H32O2/c1-12-11-20(3)13(10-17(12)21)4-5-14-15-6-7-18(22)19(15,2)9-8-16(14)20/h12-16,18,22H,4-11H2,1-3H3/t12-,13+,14+,15+,16+,18+,19+,20+/m1/s1
