Ethynyl Estradiol 3-Acetate

Base Information

• Chemical Name: Ethynyl Estradiol 3-Acetate
• CAS No.: 5779-47-5
• Molecular Formula: C22H26O3
• Molecular Weight: 338.447
• Mol file: 5779-47-5.mol

Synonyms:Ethynyl Estradiol 3-Acetate;(17α)-19-Norpregna-1,3,5(10)-trien-20-yne-3,17-diol 3-Acetate;19-Nor-17α-pregna-1,3,5(10)-trien-20-yne-3,17-diol 3-Acetate

Chemical Property of Ethynyl Estradiol 3-Acetate

Chemical Property:

• Vapor Pressure: 1.42E-09mmHg at 25°C
• Boiling Point: 468.3°C at 760 mmHg
• Flash Point: 186.8°C
• PSA: 46.53000
• Density: 1.19g/cm³
• LogP: 3.83230
• Solubility.: Chloroform, Dichloromethane, Ethyl Acetate

Purity/Quality:

95% ^*data from raw suppliers

EthynylEstradiol3-Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Ethynyl Estradiol 3-Acetate is used as a synthetic steroid with potential use as an oral contraceptive.

Technology Process of Ethynyl Estradiol 3-Acetate

There total 9 articles about Ethynyl Estradiol 3-Acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

ethinyl estradiol (57-63-6) + acetic anhydride (108-24-7) → 3-acetoxy-17α,19-norpregna-1,3,5(10)-triene-20-yn-17β-ol (5779-47-5)

Guidance literature:

With triethylamine; In dichloromethane; for 8h; Ambient temperature;

DOI:10.1021/jm00113a012

Reference yield:

ethinyl estradiol (57-63-6) → 3-acetoxy-17α,19-norpregna-1,3,5(10)-triene-20-yn-17β-ol (5779-47-5)

Guidance literature:

With acetic anhydride; In pyridine;

Reference yield:

Estrone (53-16-7) → 3-acetoxy-17α,19-norpregna-1,3,5(10)-triene-20-yn-17β-ol (5779-47-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C

2.1: tert.-butyl lithium / 2 h / -78 - 0 °C / Inert atmosphere

2.2: 20 °C

3.1: potassium carbonate / methanol / 2 h

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 8 h

5.1: isopropyl alcohol; sodium hydroxide / water

With 1H-imidazole; tetrabutyl ammonium fluoride; tert.-butyl lithium; potassium carbonate; isopropyl alcohol; sodium hydroxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;

DOI:10.1016/j.steroids.2021.108950

upstream raw materials:

ethinyl estradiol

acetic anhydride

Estrone

3-(tert-butyldimethylsilyloxy)-17α-trimethylsilylethynyl-β-estradiol

Downstream raw materials:

(17α,20E)-21-[3,4-dimethylphenyl]-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol

(17α,20E)-21-[2,6-dimethylphenyl]-19-norpregna-1,3,5(10),20-tetraene-3,17β-diol

C₃₀H₃₆O₃

Refernces

• 1、 Alotaibi, Faez,Halaweish, Fathi,Halaweish, Hossam,Iram, Surtaj,Kasten, Abigail,Kyeremateng, Jennifer,Ostlund, Trevor. "Triazole-estradiol analogs: A potential cancer therapeutic targeting ovarian and colorectal cancer". . . Retrieved 2021/12/27.
• 2、 Salman, Mohammad,Reddy,Delgado, Pete,Stotterl, Philip L.,Fulcher, Letitia C.,Chamness, Gary C.. "17α -Substituted analogs of estradiol for the development of fluorescent estrogen receptor ligands". . p. 375 - 387. Retrieved 2007/10/02.