21-Hydroxypregnenolone

Base Information

• Chemical Name: 21-Hydroxypregnenolone
• CAS No.: 1164-98-3
• Molecular Formula: C21H32 O3
• Molecular Weight: 332.483
• NSC Number: 60793
• UNII: A1L3K6161X
• DSSTox Substance ID: DTXSID301314382
• Nikkaji Number: J564.833E
• Wikipedia: 21-Hydroxypregnenolone
• Wikidata: Q27103473
• Metabolomics Workbench ID: 35446
• ChEMBL ID: CHEMBL1908012
• Mol file: 1164-98-3.mol

Synonyms:21-hydroxypregnenolone

Chemical Property of 21-Hydroxypregnenolone

Chemical Property:

• Vapor Pressure: 2.26E-11mmHg at 25°C
• Boiling Point: 483.4°Cat760mmHg
• PKA: 12.98±0.10(Predicted)
• Flash Point: 260.2°C
• PSA: 57.53000
• Density: 1.15g/cm³
• LogP: 3.48770
• Storage Temp.: Refrigerator, Under inert atmosphere
• Solubility.: Chloroform (Sparingly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 332.23514488
• Heavy Atom Count: 24
• Complexity: 567

Purity/Quality:

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

21-Hydroxypregnenolone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC3C(C1CCC2C(=O)CO)CC=C4C3(CCC(C4)O)C
• Isomeric SMILES: C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)CO)CC=C4[C@@]3(CC[C@@H](C4)O)C
• Uses: 21-Hydroxypregnenolone, is a hydroxylated metabolite of Pregnenolone (P712200), which is a GABAA antagonist and increases neurogenesis in the hippocampus. It is a modulator of cytochrome P 450-3A.

Technology Process of 21-Hydroxypregnenolone

There total 40 articles about 21-Hydroxypregnenolone 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: 98.0%

3β,21-diacetoxypregn-5-en-20-one (1693-63-6) → 21-hydroxypregnenolone (1164-98-3)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 1h;

DOI:10.3390/molecules26092643

Reference yield: 98.0%

20ξ-methoxy-21-hydroxy-3β-(tetrahydropyranyloxy)-5,17(20)-pregnadiene (81477-87-4) → 21-hydroxypregnenolone (1164-98-3)

Guidance literature:

With perchloric acid; In methanol; for 1h; Ambient temperature;

DOI:10.1021/jo00136a035

Reference yield: 98.0%

(E)-20-Methoxy-21-hydroxy-3β-(2-tetrahydropyranyloxy)-5,17(20)-pregnadiene (90244-40-9) → 3β-21-Dihydroxy-5-pregnen-20-one (1164-98-3,1499-61-2)

Guidance literature:

With perchloric acid; In methanol; water; for 0.25h;

DOI:10.1055/s-1984-30751

upstream raw materials:

21-hydroxy-3β-methoxymethoxy-5-pregnen-20-one

pregnenolone

[1-((3S,10R,13S,17S)-3-Methoxymethoxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-vinyloxy]-trimethyl-silane

3β-methoxymethoxy-5-pregnen-20-one

Downstream raw materials:

1-((3S,8S,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-trimethylsilanyloxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-trimethylsilanyloxy-ethanone O-methyl-oxime

3β,21-diacetoxypregn-5-en-20-one

3,20-dioxo-4-pregnen-21-al

Refernces

• 1、 Sondheimer et al.. "-". . p. 1278. Retrieved 1959.
• 2、 Moriarty, Robert M.,John, Lian S.,Du, Pin C.. "Hypervalent Iodine in Organic Synthesis. A Novel Route to the Dihydroxyacetone Side-chain in the Pregnene Series". . p. 641 - 642. Retrieved 1981.
• 3、 Numazawa, Mitsuteru,Nagaoka, Masao. "New Preparation and Controlled Alkaline Hydrolysis of 21-Bromo-20-ketopregnenes. A Facile Synthesis of Deoxycorticoids". . p. 81 - 84. Retrieved 1985.
• 4、 Hamilton, Niall M.,Dawson, Martin,Fairweather, Emma E.,Hamilton, Nicola S.,Hitchin, James R.,James, Dominic I.,Jones, Stuart D.,Jordan, Allan M.,Lyons, Amanda J.,Small, Helen F.,Thomson, Graeme J.,Waddell, Ian D.,Ogilvie, Donald J.. "Novel steroid inhibitors of glucose 6-phosphate dehydrogenase". supporting information; experimental part. p. 4431 - 4445. Retrieved 2012/09/11.