(20S)-20-Hydroxypregn-4-en-3-one

Base Information

• Chemical Name: (20S)-20-Hydroxypregn-4-en-3-one
• CAS No.: 145-14-2
• Molecular Formula: C21H32 O2
• Molecular Weight: 316.484
• European Community (EC) Number: 205-649-5
• UNII: 45630A64AC
• DSSTox Substance ID: DTXSID10904767
• Nikkaji Number: J6.126C
• Wikipedia: 20%CE%B2-Dihydroprogesterone,20%CE%B1-Dihydroprogesterone
• Metabolomics Workbench ID: 35448
• ChEMBL ID: CHEMBL1583424
• Mol file: 145-14-2.mol

Synonyms:20 alpha Dihydroprogesterone;20 alpha Hydroxy 4 Pregnen 3 One;20 alpha Hydroxyprogesterone;20 alpha-Dihydroprogesterone;20 alpha-Hydroxy-4-Pregnen-3-One;20 alpha-Hydroxyprogesterone;20-alpha-Dihydroprogesterone;20-alpha-hydroxy- Pregn-4-en-3-one;20-alpha-Hydroxyprogesterone;20alpha Hydroxypregn 4 Ene 3 One;20alpha-Hydroxypregn-4-Ene-3-One;Dihydroprogesterone;Pregn 4 en 3 one, 20 alpha hydroxy;Pregn-4-en-3-one, 20-alpha-hydroxy-

Chemical Property of (20S)-20-Hydroxypregn-4-en-3-one

Chemical Property:

• Vapor Pressure: 4.65E-10mmHg at 25°C
• Melting Point: 171-172 °C
• Boiling Point: 451.7°Cat760mmHg
• PKA: 15.05±0.20(Predicted)
• Flash Point: 192.4°C
• PSA: 37.30000
• Density: 1.09g/cm³
• LogP: 4.51530
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 316.240230259
• Heavy Atom Count: 23
• Complexity: 550

Purity/Quality:

99%, ^*data from raw suppliers

Δ4-Pregnen-20α-ol-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1CCC2C1(CCC3C2CCC4=CC(=O)CCC34C)C)O
• Isomeric SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C)O
• Uses: Δ4-Pregnen-20α-ol-3-one is the main metabolite of Progesterone (P755900). Studies shows regulation of estrogen receptor levels in breast cancer by Δ4-Pregnen-20α-ol-3-one and other progesterone metabolites. Δ4-Pregnen-20α-ol-3-one (Progesterone EP Impurity B) is the main metabolite of Progesterone (P755900). Studies shows regulation of estrogen receptor levels in breast cancer by Δ4-Pregnen-20α-ol-3-one and other progesterone metabolites.

Technology Process of (20S)-20-Hydroxypregn-4-en-3-one

There total 44 articles about (20S)-20-Hydroxypregn-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: 83.0%

3,3-ethylenedioxy-20(S)-hydroxy-4-pregnene → (20S)-20-hydroxypregn-4-en-3-one (145-14-2)

Guidance literature:

With toluene-4-sulfonic acid; In acetone;

DOI:10.1016/j.tet.2007.12.006

Reference yield: 54.0%

3-chloro-benzenecarboperoxoic acid (937-14-4) + (20S)-20-iodopregn-4-en-3-one → (20S)-20-hydroxypregn-4-en-3-one (145-14-2) + 17aβ-(3-Chlorobenzoyloxy)-17α-methyl-D-homoandrost-4-en-3-one + 3-Chloro-benzoic acid (S)-1-((8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl ester

Guidance literature:

In dichloromethane; water; at 0 ℃; for 1h;

DOI:10.1039/b102688g

Reference yield: 42.0%

(20S)-20-iodopregn-4-en-3-one → (20S)-20-hydroxypregn-4-en-3-one (145-14-2) + 17aβ-Hydroxy-17α-methyl-D-homoandrost-4-en-3-one

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; water; at 25 ℃; for 3h;

DOI:10.1039/b102688g

upstream raw materials:

progesterone

17β-androstane-4-ene-3-keto-17-formaldehyde

dimethyl zinc(II)

3-benzoyloxy-pregnadien-(3.5)-one-⁽²⁰⁾

Downstream raw materials:

Progesterone

4-pregnene-3α,20S-diol

7α-methyl-4-pregnene-3,20-dione

Refernces

• 1、 Strickler,Tobias. "Estradiol 17β-dehydrogenase and 20α-hydroxysteroid dehydrogenase from human placental cytosol: One enzyme with two activities?". . p. 243 - 253. Retrieved 1980.
• 2、 Nicoletti,Ghini,Baggio,Garland,Burton. "Rearrangement of 18-iodo- and 20-iodopregnanes mediated by iodosyl derivatives". . p. 1511 - 1517. Retrieved 2001.
• 3、 Duleba, Antoni J.,Takahashi, Hideyuki,Moon, Young S.. "ANDROGENIC MODULATION OF PROGESTERONE METABOLISM BY RAT GRANULOSA CELLS IN CULTURE". . p. 321 - 330. Retrieved 1983.
• 4、 Chen,Nancarrow,Sweet. "Isolation of 3β,20α-hydroxysteroid oxidoreductase from sheep fetal blood". . p. 477 - 496. Retrieved 1987.
• 5、 -. "METHODS OF NEUROPROTECTION USING NEUROPROTECTIVE STEROIDS AND A VITAMIN D". . . Retrieved 2012/01/03.