13258-68-9

Basic information

• Product Name: Ethynylestradiol Diacetate
• Synonyms: (17a)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol Diacetate;17a-Ethynylestradiol 3,17-Diacetate;19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol 3,17-Diacetate;Ethynylestradiol Diacetate;(17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol Diacetate;17α-Ethynylestradiol 3,17-Diacetate;tert-Butyl 3-broMopropanoate
• CAS NO: 13258-68-9
• Molecular Formula: C₂₄H₂₈O₄
• Molecular Weight: 380.48
• Product Categories: Chiral Reagents;Steroids
• Mol File: 13258-68-9.mol

Chemical Properties

• Boiling Point: 476.9°C at 760 mmHg
• Flash Point: 233°C
• Appearance: /
• Density: 1.18g/cm³
• Vapor Pressure: 2.94E-09mmHg at 25°C
• Refractive Index: 1.572
• Solubility: Dichloromethane, Ethyl Acetate, Methanol
• CAS DataBase Reference: Ethynylestradiol Diacetate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethynylestradiol Diacetate(13258-68-9)
• EPA Substance Registry System: Ethynylestradiol Diacetate(13258-68-9)

Safety Data

• Hazardous Substances Data: 13258-68-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethynylestradiol Diacetate is used as a pharmaceutical ingredient for its potent estrogenic effects. It is commonly utilized in the development of oral contraceptives and hormone replacement therapies, helping to regulate hormonal balance and prevent pregnancy.
Used in Cosmetics Industry:
In the cosmetics industry, Ethynylestradiol Diacetate is used as an ingredient in certain skincare products, particularly those targeting aging and menopausal skin. Its estrogenic properties can help improve skin elasticity, reduce wrinkles, and maintain overall skin health.
Used in Research and Development:
Ethynylestradiol Diacetate is also used in research and development for studying the effects of estrogen on various biological processes. This includes understanding its role in reproductive health, bone density, and other estrogen-responsive systems.

InChI:InChI=1/C24H28O4/c1-5-24(28-16(3)26)13-11-22-21-8-6-17-14-18(27-15(2)25)7-9-19(17)20(21)10-12-23(22,24)4/h1,7,9,14,20-22H,6,8,10-13H2,2-4H3/t20-,21-,22+,23+,24+/m1/s1

Upstream product

• 57-63-6 ethinyl estradiol 
• 108-24-7 acetic anhydride 
• 108-22-5 Isopropenyl acetate 

Downstream Products

• 21221-29-4 17β-acetoxy-17α-ethynyl-3-hydroxy-1,3,5[10]-estratriene 
• 242130-33-2 methyl {(17β-acetoxy-17α-ethynyl-1,3,5[10]-estratrien-3-yl)-2,3,4-tri-O-acetyl-β-D-glucopyranosid}uronate 
• 38002-18-5 17α-ethynyl-3,17β-dihydroxyestra-1,3,5(10)-trien-6-one 
• 1667-98-7 3-hydroxy-19-norpregna-1,3,5⁽¹⁰⁾-trien-20-one 

Relevant articles and documents

Asymmetric organocatalytic synthesis of 2,3-allenamides from hydrogen-bond-stabilized enynamides

Asymmetric catalytic synthesis of 2,3-allenamides from hydrogen-bond-stabilized enynamides in the presence of quinine-based bifunctional squaramide organocatalysts is described. This protocol forms a variety of 2,3-allenamides in high yields and excellent

Protection of COOH and OH groups in acid, base and salt free reactions

We report an iron-catalyzed general functional group protection method with inexpensive reagents. This environmentally benign process does not use acids or bases, and does not produce waste products. Further purification beyond filtration and evaporation is, in most cases, unnecessary. Free COOH and OH groups can be protected in a one-pot reaction.

Base-Controlled Cu-Catalyzed Tandem Cyclization/Alkynylation for the Synthesis of Indolizines

A base-controlled Cu-catalyzed tandem cyclization/alkynylation of propargylic amines provides rapid access to functionalized indolizine derivatives under mild reaction conditions. The reaction first proceeded via a 5-endo-dig aminocupration, followed by a coupling between the copper-bound intermediate and alkynyl bromide, to afford the products in good to excellent yields. The successful tandem reaction is attributed to the unique property of the bases, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) and MTBD (7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene used).

Synthesis of β-glucuronides of estradiol, ethynylestradiol and estrone

Improved syntheses for the 3-β-D-glucuronides of the steroidal sex hormones 17β-estradiol, 17α-ethynylestradiol and estrone are reported employing boron trifluoride diethyl etherate catalysis with tetraacetylated glucuronic acid or the corresponding imidate.

A Novel Efficient Approach to the Synthesis of 6-Oxo Ethinylestradiol and its 3-Isopropanesulfonate

Ethinylestradiol (1) was converted into the corresponding 6-oxo derivative 7 by a short and simple procedure involving acetate 10 and ketone 11.Phase transfer catalyzed esterification of compound 7 with propane-2-sulfonyl chloride gave sulfonate 12.

17β-Ethynyl-3,17α-estradiol and derivatives thereof

17β-ethynyl-3,17α-estradiol and derivatives thereof are prepared by epimerization of 17-acyl esters of 17α-ethynyl-3,17β-estradiol 3-ethers. 17α-ethynyl-3,17α-estradiol and its derivatives are active as post-coital antifertility agents and inhibit the growth of or reduce the size of the prostate gland and the seminal vesicle.