(20R)-17,20-Dihydroxypregn-4-en-3-one

Base Information

• Chemical Name: (20R)-17,20-Dihydroxypregn-4-en-3-one
• CAS No.: 1662-06-2
• Molecular Formula: C21H32 O3
• Molecular Weight: 332.483
• DSSTox Substance ID: DTXSID60873499
• Nikkaji Number: J366.144J
• Wikidata: Q27116937
• Metabolomics Workbench ID: 35428
• Mol file: 1662-06-2.mol

Synonyms:17 alpha,20 beta-dihydroxypregn-4-en-3-one;17 alpha,20 beta-dihydroxyprogesterone;17,20beta-dihydroxypregn-4-en-3-one;17-DHP;17alpha-hydroxy-20beta-dihydroprogesterone

Chemical Property of (20R)-17,20-Dihydroxypregn-4-en-3-one

Chemical Property:

• Vapor Pressure: 1.56E-11mmHg at 25°C
• Melting Point: 201-202oC
• Boiling Point: 487.1°C at 760 mmHg
• PKA: 14.79±0.60(Predicted)
• Flash Point: 262.5°C
• PSA: 57.53000
• Density: 1.15g/cm³
• LogP: 3.63020
• Storage Temp.: -20°C Freezer
• Solubility.: Acetone (Slightly), Methanol (Slightly), DMSO
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 332.23514488
• Heavy Atom Count: 24
• Complexity: 596

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-Pregnen-17α,20β-diol-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C1(CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O)O
• Isomeric SMILES: C[C@H]([C@]1(CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O)O
• Uses: 4-Pregnen-17α,20β-diol-3-one (cas# 1662-06-2) is a derivative of 17α-Hydroxy Progesterone (H952330), which is a metabolite of Progesterone (P755900). It can also be used as an antagonist of cb1 receptor for therapeutic use.

Technology Process of (20R)-17,20-Dihydroxypregn-4-en-3-one

There total 21 articles about (20R)-17,20-Dihydroxypregn-4-en-3-one 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: 70.0%

(8S,9S,10R,13S,14S,Z)-17-ethylidene-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one (51154-62-2) → Androstenedione (63-05-8) + 17-hydroxyprogesterone (68-96-2) + 17alpha,20beta-Dihydroxypregn-4-en-3-one (1662-06-2)

Guidance literature:

With ruthenium trichloride; Oxone; sodium hydrogencarbonate; In water; ethyl acetate; acetonitrile; at -20 - 30 ℃;

Reference yield: 28.0%

17-hydroxyprogesterone (68-96-2) → 17alpha,20beta-Dihydroxypregn-4-en-3-one (1662-06-2) + pregn-4-en-3β,17α,20β-triol (384342-63-6)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 - 5 ℃; for 1.5h;

DOI:10.1023/A:1017602526723

Reference yield:

Progesterone (57-83-0) → Androstenedione (63-05-8) + 17-hydroxyprogesterone (68-96-2) + 17α,20α-dihydroxypregn-4-en-3-one (652-69-7) + 17alpha,20beta-Dihydroxypregn-4-en-3-one (1662-06-2)

Guidance literature:

Progesterone; With ethanol; S_. cerevisiae GRF₁₈; YEp5117α; for 30h;

With chromic acid; In isopropyl alcohol; acetone; at 20 ℃; for 0.333333h;

DOI:10.1023/B:RUBI.0000008900.54667.d9

upstream raw materials:

17-hydroxy-progesterone

17-hydroxyprogesterone

Progesterone

3-benzylsulfanyl-17-hydroxy-pregna-3,5-dien-20-one

Downstream raw materials:

Progesterone

Refernces

• 1、 Ouedraogo, Yannick P.,Huang, Longchuan,Torrente, Mariana P.,Proni, Gloria,Chadwick, Ekaterina,Wehmschulte, Rudolf J.,Nesnas, Nasri. "A direct stereoselective preparation of a fish pheromone and application of the zinc porphyrin tweezer chiroptical protocol in its stereochemical assignment". . p. 575 - 581. Retrieved 2013.
• 2、 Kovganko,Kashkan,Shkumatov. "Simple synthesis of 17α20β-dihydroxypregn-4-en-3-one". . p. 55 - 56. Retrieved 2001.
• 3、 -. "A by the 3,17-dione steroid preparing steroid the synthetic method of the compound of". Paragraph 0083-0101. . Retrieved 2017/03/14.