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Ethynodiol diacetate

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Ethynodiol diacetate Basic information

Product Name:
Ethynodiol diacetate
Synonyms:
  • (3-beta,17-alpha)-19-Norpregn-4-en-20-yne-3,17-diol diacetate
  • (3-beta,17-alpha)-19-norpregn-4-en-20-yne-3,17-dioldiacetate
  • 17-(Acetyloxy)-17-ethynylestr-4-en-3-yl acetate
  • 17-alpha-Ethynyl-19-norandrost-4-ene-3-beta,17-beta-diol diacetate
  • 17-alpha-ethynyl-19-norandrost-4-ene-3-beta,17-beta-dioldiacetate
  • 17-alpha-Ethynyl-3,17-dihydroxy-4-estrene diacetate
  • 17-alpha-ethynyl-3,17-dihydroxy-4-estrenediacetate
  • 17-alpha-Ethynyl-4-estrene-3-beta,17-beta-diol diacetate
CAS:
297-76-7
MF:
C24H32O4
MW:
384.51
EINECS:
206-044-9
Product Categories:
  • VUMIDE
Mol File:
297-76-7.mol
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Ethynodiol diacetate Chemical Properties

Melting point:
~126-127°
alpha 
D -72.5° (chloroform)
Boiling point:
431.17°C (rough estimate)
Density 
1.0474 (rough estimate)
refractive index 
1.4860 (estimate)
storage temp. 
2-8°C
solubility 
Chloroform (Slightly), DMSO (Slightly)
form 
Solid
color 
White
Water Solubility 
1.4mg/L(25 ºC)
CAS DataBase Reference
297-76-7(CAS DataBase Reference)
NIST Chemistry Reference
Ethynodiol diacetate(297-76-7)
EPA Substance Registry System
Ethynodiol diacetate (297-76-7)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
20/21/22-40
Safety Statements 
22-36
WGK Germany 
3
RTECS 
RC8963000
HS Code 
2937230000

MSDS

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Ethynodiol diacetate Usage And Synthesis

Description

Ethynodiol diacetate is a synthetic progestogen. It prevents the development of osteoporosis in ovariectomized rats when administered at a dose of 9 μg/animal per day. Ethynodiol diacetate inhibits copulatory ovulation in rabbits. Formulations containing ethynodiol diacetate have been used as oral contraceptives.

Originator

Lutometrodiol,Searle,France,1965

Uses

anticonvulsant

Uses

Ethynodiol Diacetate is used as a hormonal contraceptive, birth control.

Definition

ChEBI: Ethynodiol diacetate is a steroid ester and a terminal acetylenic compound. It has a role as an estrogen receptor modulator, a contraceptive drug and a synthetic oral contraceptive. It is functionally related to an ethynodiol.

Manufacturing Process

A mixture of 30 parts of 17α-ethynyl-19-norandrost-4-ene-3β,17β-diol, 360 parts of dry pyridine, and 111 parts of acetic anhydride, under nitrogen, is stirred and heated at the reflux temperature for about 5 hours. This reaction mixture is cooled, then poured into approximately 3,500 parts of cold water and the resulting aqueous mixture is stirred at room temperature for about 0.5 hour. The precipitate which forms is collected by filtration, then is washed on the filter with water and dried in air. This solid material is extracted into ether, and the ether solution is washed successively with 10% aqueous

Therapeutic Function

Progestin; Oral contraceptive ingredient

General Description

Ethynodiol diacetate, 19-norpregn-4-en-20-yne-3β,17α-diol diacetate, is a prodrug ofnorethindrone. A combination of hydrolysis of both estersand oxidation of the C3 alcohol to the ketone is necessary toprovide the fully active progestin.

Safety Profile

Suspected carcinogen. Human reproductive effects by ingestion: menstrual cycle changes. Experimental reproductive effects. Mutation data reported. A steroid. When heated to decomposition it emits acrid smoke and irritating fumes.

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