Isoprogesterone

Base Information

• Chemical Name: Isoprogesterone
• CAS No.: 2000-66-0
• Molecular Formula: C21H30O2
• Molecular Weight: 314.468
• UNII: QF9G358XQX
• Nikkaji Number: J148.904F
• Mol file: 2000-66-0.mol

Synonyms:Isoprogesterone;17-Isoprogesterone;2000-66-0;QF9G358XQX;UNII-QF9G358XQX;Progesterone impurity M [EP];Pregn-4-ene-3,20-dione, (17alpha)-;(8S,9S,10R,13S,14S,17R)-17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one;(17alpha)-Pregn-4-ene-3,20-dione;SCHEMBL9120521;NCGC00090798-03;PROGESTERONE IMPURITY M [EP IMPURITY];(17.ALPHA.)-PREGN-4-ENE-3,20-DIONE;PREGN-4-ENE-3,20-DIONE, (17.ALPHA.)-

Chemical Property of Isoprogesterone

Chemical Property:

• Melting Point: 145 °C
• Boiling Point: 447.2±45.0 °C(Predicted)
• PSA: 34.14000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 4.72350
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Dioxane (Slightly), Methanol (Slightly)
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 314.224580195
• Heavy Atom Count: 23
• Complexity: 589

Purity/Quality:

99%, ^*data from raw suppliers

17α-Progesterone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C
• Isomeric SMILES: CC(=O)[C@@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C
• Uses: 17α-Progesterone is a testosterone precursror generated from cholesterol. Also used as a diagnostic agent in the identification and study of ovarian Leydig cell tumor disease.

Technology Process of Isoprogesterone

There total 24 articles about Isoprogesterone 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:

20ξ-(Diethylphosphono)-20ξ-isocyano-3-methoxypregna-3,5-diene (139527-71-2) → Progesterone (57-83-0) + 17α-progesterone (2000-66-0)

Guidance literature:

With perchloric acid; In 1,4-dioxane; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1021/jo00034a012

Reference yield:

1-(3,20-dioxo-5α-pregnan-2ξ-yl)-pyridinium; bromide (103000-97-1) → progesterone (57-83-0,851-22-9,2000-66-0,2755-10-4,3562-13-8,3795-19-5,5750-05-0,14546-13-5,36027-73-3,36027-74-4,55122-80-0,56271-98-8,59952-90-8,73889-98-2,137940-28-4) + (5S,8S,9S,10R,13S,14S,17S)-17-acetyl-10,13-dimethyl-4,5,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (65556-93-6)

Guidance literature:

under 10 Torr;

DOI:10.1021/ja01875a007

Reference yield:

acetic acid (64-19-7,77671-22-8) + (4α,5)epoxy-5α-pregnan-3,20-dione (17503-05-8) → progesterone (57-83-0,851-22-9,2000-66-0,2755-10-4,3562-13-8,3795-19-5,5750-05-0,14546-13-5,36027-73-3,36027-74-4,55122-80-0,56271-98-8,59952-90-8,73889-98-2,137940-28-4)

Guidance literature:

DOI:10.1021/jo01367a001

upstream raw materials:

1-(3,20-dioxo-5α-pregnan-2ξ-yl)-pyridinium; bromide

acetic acid

(4α,5)epoxy-5α-pregnan-3,20-dione

(4β,5)-epoxy-5β-pregnan-3,20-dione

Downstream raw materials:

5-pregnene-3,20-dione-3,20-bisethyleneketal

C₂₃H₃₄O₃

C₂₅H₃₈O₄

Benzoic acid 17-acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-2-yl ester

Refernces

• 1、 Stoelwinder,Van Zoest,Van Leusen. "Chemistry of N,P-acetals: Application to the synthesis of 20-ketosteroids". . p. 2249 - 2252. Retrieved 2007/10/02.
• 2、 Solo,Kumar,Alks,Duax. "Structural requirements for progestational activity. Synthesis and properties of rac-8α,9β,10α,14β-progesterone". . p. 129 - 133. Retrieved 2007/10/18.