3beta-Hydroxy-5alpha-pregn-16-en-20-one

Base Information

• Chemical Name: 3beta-Hydroxy-5alpha-pregn-16-en-20-one
• CAS No.: 566-61-0
• Molecular Formula: C21H32 O2
• Molecular Weight: 316.484
• UNII: 3KVC0NOT64
• DSSTox Substance ID: DTXSID101292572
• Nikkaji Number: J505.847C
• Wikidata: Q27257448
• Mol file: 566-61-0.mol

Synonyms:16-pregnenolone;16-pregnolone;16-pregnolone, (3alpha,5alpha)-isomer;16-pregnolone, (3alpha,5beta)-isomer;3 beta-hydroxy-5 alpha-pregn-16-en-20-one

Chemical Property of 3beta-Hydroxy-5alpha-pregn-16-en-20-one

Chemical Property:

• Vapor Pressure: 9.72E-10mmHg at 25°C
• Melting Point: 202-204 °C
• Boiling Point: 443.7°Cat760mmHg
• PKA: 14.81±0.70(Predicted)
• Flash Point: 189.1°C
• PSA: 37.30000
• Density: 1.077g/cm³
• LogP: 4.51530
• XLogP3: 4.7
• 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:

>95% ^*data from raw suppliers

Allopregnenolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• Isomeric SMILES: CC(=O)C1=CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@@H](C4)O)C)C
• Uses: Allopregnenolone, acts as a GABAA receptor positive allosteric modulator. It is a metabolite of Progesterone (P755900). s It is also a neuroactive steroid present in the blood and also the brain.

Technology Process of 3beta-Hydroxy-5alpha-pregn-16-en-20-one

There total 7 articles about 3beta-Hydroxy-5alpha-pregn-16-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: 92.0%

tigogenin (77-60-1) → allopregnenolone (566-61-0) + (R)-4-methyl-δ-valerolactone (2857-75-2)

Guidance literature:

tigogenin; With acetic anhydride; In acetic acid; at 200 ℃; for 1h;

With dihydrogen peroxide; sodium phosphotungstate; In water; butan-1-ol; at 80 ℃; for 2h;

With sodium hydroxide; In water; butan-1-ol; for 2h; Product distribution / selectivity; Heating / reflux;

Reference yield: 76.9%

bromobenzene (108-86-1,52753-63-6) + C25H38O5 (897047-83-5) → C27H40O3 (1319208-32-6) + allopregnenolone (566-61-0)

Guidance literature:

bromobenzene; With iodine; magnesium; In tetrahydrofuran; for 1h; Cooling with ice; Inert atmosphere;

C₂₅H₃₈O₅; In tetrahydrofuran; for 6h; Inert atmosphere; Reflux;

With ammonium chloride; In tetrahydrofuran; water; Saturated solution; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.05.122

Reference yield:

→ 3β-Hydroxy-20-oxo-5α-pregna-16-en (566-59-6,566-60-9,566-61-0,21080-60-4,31686-13-2,33465-15-5)

Guidance literature:

Verb. (4g), Photolyse;

upstream raw materials:

tigogenin

bromobenzene

C₂₅H₃₈O₅

Downstream raw materials:

3α-Hydroxy-5α-pregn-16-en-20-one 3-m-iodobenzoate

3α-Hydroxy-5α-pregna-9(11),16-dien-20-one

pregn-4-ene-9α,16α,17α-triol-3,20-dione 16,17-acetonide

3β-(t-butyldimethylsilyloxy)-16α-(dimethylphenylsilyl)-5α-pregnan-20-one

Refernces

• 1、 -. "Production process for 16-dehydropregnenoneol and its analogs". Page/Page column 4. . Retrieved 2008/06/13.