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434-03-7

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434-03-7 Usage

Description

Ethisterone is an orally bioavailable synthetic progestin and a derivative of testosterone (Item Nos. ISO60154 | 15645) that binds to progesterone and androgen receptors (EC50s = 23 and 23.1 nM, respectively, in yeast). Ethisterone (1 μM) downregulates progesterone receptors in MCF-7 cells.

Chemical Properties

Off-White Powder

Originator

Lutocyclin,Ciba

Uses

Different sources of media describe the Uses of 434-03-7 differently. You can refer to the following data:
1. Synthetic progestogen; metabolite of Danazol; intermediate in the synthesis of Spironolactone
2. Ethisterone has been used as a component in Dulbecco′s modified eagle medium (DMEM) to culture the transfected COS-7 cell for transient transfection assay and?gene transfection assay.

Definition

ChEBI: A 17beta-hydroxy steroid that is testosterone in which the 17beta hydrogen is replaced by an ethynyl group. Ethisterone was the first orally active progestin and is a metabolite of danazol.

Manufacturing Process

0.5 part of δ5:6-17-ethinyl-androstendiol-(3:17) is dissolved in 10 parts of dry acetone, the solution is mixed with a solution of 1 part of tertiary aluminum butylate in 40 parts of absolute toluene and the whole is heated to boiling in a reflux apparatus for 21 hours. After the reaction mixture has cooled it is diluted with 100 parts of ether, the solution is washed with dilute mineral acid and with water, dried and the solvent is evaporated. In this manner there is obtained δ5:6-17-ethinyl-androstene-3-one-17-ol (ethisterone); MP: 270°- 272°C; it may be recrystallized from ethyl acetate.

Therapeutic Function

Progestin

General Description

Ethisterone is a?progestogen. It is a danazol derivative.

Biochem/physiol Actions

Ethisterone acts as a progestational agent. It is consumed by pregnant mothers to prevent miscarriage.

Check Digit Verification of cas no

The CAS Registry Mumber 434-03-7 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,3 and 4 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 434-03:
(5*4)+(4*3)+(3*4)+(2*0)+(1*3)=47
47 % 10 = 7
So 434-03-7 is a valid CAS Registry Number.
InChI:InChI=1/C21H28O2/c1-4-21(23)12-9-18-16-6-5-14-13-15(22)7-10-19(14,2)17(16)8-11-20(18,21)3/h1,13,16-18,23H,5-12H2,2-3H3/t16-,17+,18+,19+,20+,21+/m1/s1

434-03-7 Well-known Company Product Price

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  • Sigma-Aldrich

  • (46272)  Ethisterone  VETRANAL, analytical standard

  • 434-03-7

  • 46272-250MG

  • 329.94CNY

  • Detail

434-03-7SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name ethisterone

1.2 Other means of identification

Product number -
Other names Produxan

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:434-03-7 SDS

434-03-7Downstream Products

434-03-7Relevant articles and documents

A Short and Efficient Synthetic Method for the Corticosteroid Side-Chain from 17-Keto Steroids

Kataoka, Hideaki,Watanabe, Kiyoshi,Miyazaki, Ken-ichi,Tahara, Shin-ichiro,Ogu, Ken-ichi,et al.

, p. 1705 - 1708 (1990)

21-Acyloxy-16(17)-ene-20-keto steroids were synthesized from 17-keto steroids in 4 steps using palladium(II)-catalyzed oxidative rearrangement of propargyl esters as a key reaction.

Method for preparing 17alpha-hydroxyprogesterone

-

Paragraph 0028; 0030, (2017/08/27)

The invention discloses a method for preparing 17alpha-hydroxyprogesterone. According to the method, 4-androstenedione I serves as the raw material, a 17-site branched chain is introduced through ethynylation reaction, a 17-site beta-hydroxyl group is converted into an alpha-hydroxyl group through catalytic reaction, and finally 17alpha-hydroxyprogesterone is prepared through carbonylation reaction. The reaction formula is shown in the description. Four steps of reaction are conducted with 4-androstenedione as the raw material, a 17-site side chain is introduced through ethynylation reaction, the 17beta-hydroxyl group is converted into the 17alpha-hydroxyl group through transposition reaction, the weight yield of each step ranges from 85% to 109%, the total weigh yield is 85% or above, use of virulent acetone cyanohydrin is avoided, the raw material conversion rate is high, selectivity is good, production cost of 17alpha-hydroxyprogesterone is reduced, the process is safe, and large-scale industrial production is easy.

Process for the preparation of danazol

-

, (2019/02/04)

The invention discloses preparation methods of danazol and an intermediate thereof. The preparation method of danazol is prepared by the steps of taking androstenedione as a starting raw material, and carrying out 3-site enol etherification, 17-site carbonyl ethinylation, 3-site hydrolysis, 2-site methylidynel hydroxylation and oximation to obtain danazol. The 3-site enol etherification comprises firstly carrying out a reaction of androstenedione and triethyl orthoformate for 4-10 h in the presence of absolute ethyl alcohol and p-toluenesulfonic acid and at the temperature of 30-50 DEG C, then adding triethylamine at the temperature of 0-10 DEG C, and continuing to carry out a reaction for 0.2-1 h; the 17-site carbonyl ethinylation comprises firstly carrying out a reaction of a potassium hydroxide powder for 1-2 h in an acetylene airflow and at the temperature of 5-10 DEG C, and then carrying out a reaction with the 3-site enol etherified product for 2-4 h in the presence of tetrahydrofuran and a catalyst, at the temperature of 15-30 DEG C and in the acetylene airflow. The 3-site enol etherification is mild in reaction conditions and relatively high in yield, and the 17-site carbonyl ethynylation is relatively high in reaction yield and relatively short in time.

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