Allopregnan-3beta-ol-20-one

Base Information

• Chemical Name: Allopregnan-3beta-ol-20-one
• CAS No.: 516-55-2
• Molecular Formula: C21H34 O2
• Molecular Weight: 318.5
• NSC Number: 97078
• DSSTox Substance ID: DTXSID40859251
• Wikipedia: Allopregnanolone
• Wikidata: Q28487680
• Mol file: 516-55-2.mol

Synonyms:3 alpha Hydroxy 5 alpha pregnan 20 one;3 alpha Hydroxy 5 beta pregnan 20 one;3 alpha, 5 beta Tetrahydroprogesterone;3 alpha, 5 beta-Tetrahydroprogesterone;3 alpha-Hydroxy-5 alpha-pregnan-20-one;3 alpha-Hydroxy-5 beta-pregnan-20-one;3 Hydroxypregnan 20 one;3-Hydroxypregnan-20-one;3beta Hydroxy 5alpha pregnan 20 one;3beta-Hydroxy-5alpha-pregnan-20-one;Allopregnan 3 beta ol 20 one;Allopregnan-3 beta-ol-20-one;Allopregnanolone;alpha-Hydroxy-5 alpha-pregnan-20-one, 3;alpha-Hydroxy-5 beta-pregnan-20-one, 3;alpha-pregnan-20-one, 3 alpha-Hydroxy-5;beta-ol-20-one, Allopregnan-3;beta-pregnan-20-one, 3 alpha-Hydroxy-5;Eltanolone;Epipregnanolone;Pregnan 3alpha ol 20 one;Pregnan-3alpha-ol-20-one;Pregnanolone;Pregnanolone, (3alpha)-isomer;Pregnanolone, (3alpha, 5beta, 17-alpha)-isomer;Pregnanolone, (3alpha,5alpha)-isomer;Pregnanolone, (3alpha,5beta)-isomer;Pregnanolone, (3beta)-isomer;Pregnanolone, (3beta, 5alpha)-isomer;Pregnanolone, (3beta, 5alpha, 17alpha)-isomer;Pregnanolone, (3beta, 5alpha, 8alpha, 17beta)-isomer;Pregnanolone, (3beta, 5beta)-isomer;Pregnanolone, (3beta, 5beta, 17alpha)-isomer;Pregnanolone, (3beta, 5beta,14beta)-isomer;Pregnanolone, (5alpha)-isomer;Sepranolone

Chemical Property of Allopregnan-3beta-ol-20-one

Chemical Property:

• Vapor Pressure: 3.05E-09mmHg at 25°C
• Melting Point: 200℃
• Boiling Point: 431.2°Cat760mmHg
• PKA: 15.12±0.70(Predicted)
• Flash Point: 183.9°C
• PSA: 37.30000
• Density: 1.053g/cm³
• LogP: 4.59520
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 4.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 318.255880323
• Heavy Atom Count: 23
• Complexity: 500

Purity/Quality:

98% ^*data from raw suppliers

Allopregnanolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C
• Recent ClinicalTrials: Allopregnanolone Regenerative Therapeutic for Mild Alzheimer's Disease
• Recent EU Clinical Trials: Allopregnanolone effects on short term memory
• Description: Allopregnanolone is a neuroactive metabolite of progesterone. It is a potent positive allosteric modulator of the action of GABA on the GABAA receptor.
• Biological functions: Allopregnanolone mediates its effects through modulation of the GABAA receptor.Allopregnanolone is reported to modulate the GABA-ergic function by increasing the GABAA receptor opening frequency and duration of the receptor at concentrations in the nanomolar range. A balance between unbinding, desensitization, and reopening of the desensitized GABAA receptor underlies the delay of the inhibitory postsynaptic currents.?Allopregnanolone slows the rate of recovery of the GABAA receptor from desensitization and possibly increases the rate of entry into fast desensitized states. Allopregnanolone exerts neurogenetic, neuroprotective, antidepressant, and anxiolytic effects. Reduced levels of allopregnanolone are found to be associated with major depression, anxiety disorders, premenstrual dysphoric disorder, and Alzheimer’s disease. Allopregnanolone is actively produced in the pineal gland compared with the brain and pineal allopregnanolone acts on Purkinje cells to prevent apoptosis in the juvenile quail.
• Uses: Isopregnanolone is used in the preparation of antimicrobial and anti-leukemic steroids. Intermediate.

Technology Process of Allopregnan-3beta-ol-20-one

There total 66 articles about Allopregnan-3beta-ol-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: 100.0%

Pregnenolone (145-13-1) → isopregnanolone (516-55-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; acetic acid; In tetrahydrofuran; at 60 ℃; under 3102.97 Torr;

Reference yield: 100.0%

pregnenolone acetate (906-83-2) → isopregnanolone (516-55-2)

Guidance literature:

With potassium hydroxide; for 0.25h; Ambient temperature;

DOI:10.1248/cpb.40.1143

Reference yield: 100.0%

Pregnenolone acetate (1778-02-5) → isopregnanolone (516-55-2) + pregnenolone acetate (906-83-2)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; at 20 ℃; under 10343.2 Torr;

DOI:10.1016/j.ejmech.2013.11.019

upstream raw materials:

Progesterone

dihydroprogesterone

Pregnenolone

pregnenolone acetate

Downstream raw materials:

dihydroprogesterone

20-oxo-2,3-seco-5α-pregnanedioic acid-(2,3)

C₃₀H₄₂N₂O₂

C₃₀H₄₂N₂O₂

Refernces

• 1、 Marker,Kamm,Jones. "-". . p. 1595. Retrieved 1937.
• 2、 -. "COMPOSITIONS AND METHODS FOR TREATING CNS DISORDERS". Paragraph 0579. . Retrieved 2021/01/23.
• 3、 -. "PROCESS FOR THE PREPARATION OF 3ALPHA-HYDROXY-5ΑLPHA-PREGNAN-20-ONE (BREXANOLONE)". Page/Page column 12; 13. . Retrieved 2020/06/10.