Gestodene

Base Information

• Chemical Name: Gestodene
• CAS No.: 60282-87-3
• Deprecated CAS: 110541-55-4
• Molecular Formula: C21H26O2
• Molecular Weight: 310.436
• Hs Code.: 29144000
• European Community (EC) Number: 262-145-8
• UNII: 1664P6E6MI
• DSSTox Substance ID: DTXSID6046478
• Nikkaji Number: J18.212E
• Wikipedia: Gestodene
• Wikidata: Q408289
• NCI Thesaurus Code: C87240
• Metabolomics Workbench ID: 43698
• ChEMBL ID: CHEMBL1213583
• Mol file: 60282-87-3.mol

Synonyms:13-ethyl-17-hydroxy-18,19-dinor-17 alpha-pregna-4,15-dien-20-yn-3-one;17-alpha-ethinyl-13-ethyl-17 beta-hydroxy-4,15-gonadien-3-one;18,19-dinorpregna-4,15-dien-20-yn-3-one, 13-ethyl-17-hydroxy-, (17-alpha)-;Gestoden;Gestodene;Gestodene, ((17alpha)-(+-))-isomer;SH B 3331

Chemical Property of Gestodene

Chemical Property:

• Appearance/Colour: white crystalline solid
• Vapor Pressure: 1.66E-10mmHg at 25°C
• Melting Point: 190-192 °C
• Refractive Index: 1.588
• Boiling Point: 462.7 °C at 760 mmHg
• PKA: 12.16±0.40(Predicted)
• Flash Point: 196.9 °C
• PSA: 37.30000
• Density: 1.15 g/cm³
• LogP: 3.65860
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: >20mg/mL
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 310.193280068
• Heavy Atom Count: 23
• Complexity: 648

Purity/Quality:

99% ^*data from raw suppliers

Gestodene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 62
• Safety Statements: 36/37-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC12CCC3C(C1C=CC2(C#C)O)CCC4=CC(=O)CCC34
• Isomeric SMILES: CC[C@]12CC[C@H]3[C@H]([C@@H]1C=C[C@]2(C#C)O)CCC4=CC(=O)CC[C@H]34
• Recent ClinicalTrials: Improvement of Quality of Life in Patients Using Low-dose Pills in the Different Phases of Menacme
• Description: Gestodene is a progestogen, recently launched in combination with ethinyl estradiol as an oral contraceptive.Gestodene is a steroid. It has a role as an estrogen.Gestodene, one of three new gonane progestins, is the most potent on a per weight basis in regard to progestational effects and has little or no estrogenic effect. In in vivo animal studies, gestodene also has less androgenic activity compared with progestins found in older combination oral contraceptive formulations.
• Uses: Gestodene is an orally active gestogen with a progesterone-like profile of activity. Gestodene is used in combination with estrogen as an oral contraceptive. Orally active gestogen with progesterone-like profile of activity. Used in combination with estrogen as oral contraceptive. Estrogens and progestins are female hormones. They are produced by the body and are necessary for the normal sexual development of the female and for the regulation of the menstrual cycle during the childbearing years. Gestodene is a progestogen hormonal

Technology Process of Gestodene

There total 24 articles about Gestodene 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: 90.0%

17α-ethynyl-18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5,15-estradien-17β-ol (64133-14-8) + 3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-10,15-estradiene → gestodene (60282-87-3)

Guidance literature:

17α-ethynyl-18-methyl-3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-5,15-estradien-17β-ol; 3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-10,15-estradiene; With water; hydrogenchloride; In acetone; at 20 ℃; for 0.75h;

With sodium hydrogencarbonate; In water; acetone; pH=7; Product distribution / selectivity;

Reference yield: 90.0%

3,3-(2',2'-dimethyl-1',3'-propylenedioxy)-17α-ethnyl-17β-hydroxy-18-methyl-5,15-estradiene → gestodene (60282-87-3)

Guidance literature:

With hydrogenchloride; In acetone; at 20 ℃; for 0.75h;

DOI:10.1055/s-2004-829070

Reference yield: 80.0%

3-ethoxy-18-methyl-estra-3,5,15-trien-17-one (1323980-05-7) + acetylenemagnesium bromide (4301-14-8) → gestodene (60282-87-3)

Guidance literature:

3-ethoxy-18-methyl-estra-3,5,15-trien-17-one; acetylenemagnesium bromide; In tetrahydrofuran; 2-MeTHF; at 20 - 25 ℃; for 2h;

With hydrogenchloride; In ethanol; water; at 7 - 10 ℃; for 2h;

upstream raw materials:

ethylene glycol

15α-Acetoxy-18-methyl-4-estren-3,17-dion

acetylene

17α-Ethinyl-3,3-ethylendithio-18-methyl-4,15-estradien-17β-ol

Downstream raw materials:

13-β-ethyl-18,19-dinorpregna-4,14,16-trien-3,20-dione

Refernces

• 1、 -. "One kind is used in the midbody of dienone the synthesis is pregnant and its preparation method and application (by machine translation)". Paragraph 0041-0058. . Retrieved 2016/10/08.
• 2、 -. "Process for the preparation of delta(15-16)-17-ketosteroids and use thereof in the synthesis of pharmacologically active compounds". Page/Page column 7; 11; 14; 21; 22. . Retrieved 2010/02/14.