3alpha-Hydroxypregn-5-en-20-one

Base Information

• Chemical Name: 3alpha-Hydroxypregn-5-en-20-one
• CAS No.: 19037-28-6
• Molecular Formula: C21H32 O2
• Molecular Weight: 316.484
• DSSTox Substance ID: DTXSID10859283
• Nikkaji Number: J534.626F
• ChEMBL ID: CHEMBL383839
• Mol file: 19037-28-6.mol

Synonyms:19037-28-6;3alpha-Hydroxypregn-5-en-20-one;3-epi-Pregnenolone;1-[(3R,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone;5-pregnene-3alpha-ol-20-one;Pregn-5-en-20-one, 3alpha-hydroxy-;Pregn-5-en-20-one, 3-hydroxy-, (3a)-;CHEMBL383839;SCHEMBL6051876;DTXSID10859283;3alpha-hydroxy-pregn-5-en-20-one;(3alpha)-3-hydroxypregn-5-en-20-one;J-012290

Chemical Property of 3alpha-Hydroxypregn-5-en-20-one

Chemical Property:

• Vapor Pressure: 1.02E-09mmHg at 25°C
• Boiling Point: 443.3°Cat760mmHg
• Flash Point: 188.9°C
• PSA: 37.30000
• Density: 1.09g/cm³
• LogP: 4.51530
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (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:

98% ^*data from raw suppliers

3-epi-Pregnenolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@H](C4)O)C)C
• Uses: An epimer of Pregnenolone (P712200), a GABAA antagonist and increases neurogenesis in the hippocampus.

Technology Process of 3alpha-Hydroxypregn-5-en-20-one

There total 17 articles about 3alpha-Hydroxypregn-5-en-20-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: 94.4%

3β-hydroxyl-5-pregnen-20-one acetate (5223-98-3) → (3α)-3-hydroxypregn-5-en-20-one (19037-28-6)

Guidance literature:

With methanol; sodium hydroxide; at 40 ℃; for 4h; Inert atmosphere;

Reference yield: 92.81%

3β-hydroxypregn-5-en-20-one-3-acetate (1093959-59-1) → pregnenolone (145-13-1,566-63-2,19037-28-6,38372-24-6)

Guidance literature:

With methanol; potassium carbonate; at 20 ℃;

Reference yield: 23.0%

17-Hydroxypregnenolone (387-79-1) → pregnenolone (145-13-1,566-63-2,19037-28-6,38372-24-6)

Guidance literature:

With potassium acetate; L-proline; In dimethyl sulfoxide; at 130 ℃;

DOI:10.1039/c9sc02543j

upstream raw materials:

16-dehydropregnenolone acetate

3β-hydroxypregn-5-en-20-one-3-acetate

17-Hydroxypregnenolone

pregn-5-ene-3,20-dione

Downstream raw materials:

Pregnenolone acetate

Pregnenolone

androst-4-en-3-one-17β-carboxylic acid

dehydroepiandrosterone

Refernces

• 1、 Mostinski, Yelena,Lankri, David,Konovalov, Yana,Nataf, Riva,Tsvelikhovsky, Dmitry. "Proline-promoted dehydroxylation of α-ketols". . p. 9345 - 9350. Retrieved 2019/10/22.
• 2、 -. "Steroidal androgen receptor inhibitor as well as preparation method and medical application thereof". . . Retrieved 2016/12/26.