Gestonorone

Base Information

• Chemical Name: Gestonorone
• CAS No.: 2137-18-0
• Molecular Formula: C20H28O3
• Molecular Weight: 316.441
• European Community (EC) Number: 218-378-2
• UNII: H4G605B7VP
• DSSTox Substance ID: DTXSID50175631
• Nikkaji Number: J17.210C
• Wikipedia: Gestronol
• Wikidata: Q5553699
• Metabolomics Workbench ID: 154060
• ChEMBL ID: CHEMBL3707212
• Mol file: 2137-18-0.mol

Synonyms:Gestonorone;2137-18-0;17a-Hydroxy-19-norprogesterone;(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one;19-Norpregn-4-ene-3,20-dione, 17-hydroxy-;H4G605B7VP;Gestronol;TX 045;17a-Hydroxy-19-norpregn-4-ene-3,20-dione;Gestonoron;16895-64-0;Gestonorone [INN:BAN];UNII-H4G605B7VP;GESTONORONE [WHO-DD];SCHEMBL141624;CHEMBL3707212;DTXSID50175631;CHEBI:135991;17alpha-Hydroxy-19-norprogesterone;EINECS 218-378-2;AKOS015896530;DB13230;NCGC00510144-01;EC 218-378-2;17alpha-Hydroxy-19-norpregn-4-ene-3,20-dione;Q5553699;(8R,9S,10R,13S,14S,17R)-17-acetyl-17-hydroxy-13-methyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

Chemical Property of Gestonorone

Chemical Property:

• Appearance/Colour: White or almost white crystalline powder
• Vapor Pressure: 1.95E-11mmHg at 25°C
• Melting Point: 222-224 °C
• Refractive Index: 1.564
• Boiling Point: 484.9 °C at 760 mmHg
• PKA: 13.03±0.40(Predicted)
• Flash Point: 261.2 °C
• PSA: 54.37000
• Density: 1.17 g/cm³
• LogP: 3.44830
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 316.20384475
• Heavy Atom Count: 23
• Complexity: 592

Purity/Quality:

99% ^*data from raw suppliers

Gestonorone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34)C)O
• Isomeric SMILES: CC(=O)[C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@H]34)C)O
• Uses: Gestonorone is a steroidal progestin. It has been shown to have accelerated body weight gain and caused the atrophy of the prostate, uterus, and seminal vesicles in rats. It is also an inhibitor of the reductive pathway of Testosterone (T155000) metabolism.

Technology Process of Gestonorone

There total 25 articles about Gestonorone 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: 97.97%

C20H27ClO3 → 17-alpha-Hydroxy-19-norprogesterone (2137-18-0)

Guidance literature:

With iron; acetic acid; at 60 ℃; for 3h; Reagent/catalyst; Temperature;

Reference yield:

3-methoxy-17α-[(trimethylsilyl)oxy]estr-2,5(10)-dien-17-carbonitrile + methyllithium (917-54-4) → 17-alpha-Hydroxy-19-norprogesterone (2137-18-0)

Guidance literature:

3-methoxy-17α-[(trimethylsilyl)oxy]estr-2,5(10)-dien-17-carbonitrile; methyllithium; With N,N,N,N,-tetramethylethylenediamine; In tert-butyl methyl ether; at -40 - -30 ℃; for 1h;

With hydrogenchloride; In tert-butyl methyl ether; at -30 - 25 ℃; for 16h;

Reference yield:

17α-hydroxy-3-methoxy-19-norpregna-1,3,5(10)-trien-20-one (1624-58-4) → 17-alpha-Hydroxy-19-norprogesterone (2137-18-0)

Guidance literature:

Multi-step reaction with 3 steps

1: benzene; toluene-4-sulfonic acid / Entfernen des entstehenden Wassers

2: diethyl ether; lithium; liquid ammonia / anschliessend Behandeln mit Aethanol

3: methanol.HCl

With hydrogenchloride; diethyl ether; ammonia; lithium; toluene-4-sulfonic acid; benzene;

DOI:10.1021/ja01555a053

upstream raw materials:

20,20-ethanediyldioxy-3-methoxy-19-nor-pregna-2,5⁽¹⁰⁾-dien-17-ol

17α-hydroxy-3-methoxy-19-norpregna-1,3,5(10)-trien-20-one

3-hydroxy-19-norpregna-1,3,5⁽¹⁰⁾,16-tetraen-20-one

16α,17α-epoxy-17-acetyl-Δ^1,3,5(10)-estratriene

Downstream raw materials:

17α-acetoxy-19-norpregna-4-ene-3,20-dione

17α-acetoxy-6-methylene-19-norpregn-4-ene-3,20-dione

nomegestrol acetate

gestonorone caproate

Refernces

• 1、 -. "Nomegestrol intermediate synthesizing method". . . Retrieved 2017/07/19.
• 2、 Lu, He-Lin,Wu, Zong-Wen,Song, Shu-Yong,Liao, Xiao-Dan,Zhu, Yan,Huang, Yun-Sheng. "An improved synthesis of nomegestrol acetate". . p. 431 - 436. Retrieved 2014/04/17.