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58-19-5

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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

58-19-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 18, 2017

Revision Date: Aug 18, 2017

1.Identification

1.1 GHS Product identifier

Product name metholone

1.2 Other means of identification

Product number -
Other names Dromostanolone

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:58-19-5 SDS

58-19-5Relevant articles and documents

Cyclopropanation of steroidal A-ring 2-enol derivatives

Templeton,Paslat,Wie

, p. 2058 - 2064 (1978)

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Synthesis of 2α-methyldihydrotestosterone from tigogenin

Sikharulidze,Merlani,Amiranashvili

, p. 294 - 294 (2007/10/03)

-

STEROIDS. CCIX. RING A MODIFIED HORMONE ANALOGS. V.

EDWARDS,CALZADA,BOWERS

, p. 178 - 182 (2007/10/10)

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