3beta,5alpha-Tetrahydrodeoxycorticosterone

Base Information

• Chemical Name: 3beta,5alpha-Tetrahydrodeoxycorticosterone
• CAS No.: 567-02-2
• Molecular Formula: C21H34O3
• Molecular Weight: 334.499
• NSC Number: 113927
• DSSTox Substance ID: DTXSID30862214
• Wikipedia: Tetrahydrodeoxycorticosterone
• ChEMBL ID: CHEMBL4591234
• Mol file: 567-02-2.mol

Synonyms:3 alpha,21-dihydroxy-5 beta-pregnan-20-one;3 alpha,5 beta-tetrahydrodeoxycorticosterone;3 beta,5 alpha-tetrahydrodeoxycorticosterone;3,21-dihydroxypregnan-20-one;3alpha,21-dihydroxy-5alpha-pregnan-20-one;5alpha-pregnan-3alpha,21-diol-20-one;5alpha-pregnane-3alpha,21-diol-20-one;5alpha-THDOC;allotetrahydrodeoxycorticosterone;pregnane-3,21-diol-20-one;tetrahydrodeoxycorticosterone;tetrahydrodeoxycorticosterone, (3alpha,5alpha)-isomer;tetrahydrodeoxycorticosterone, (3beta,5alpha)-isomer;tetrahydrodesoxycorticosterone;THDOC

Chemical Property of 3beta,5alpha-Tetrahydrodeoxycorticosterone

Chemical Property:

• Vapor Pressure: 8.07E-11mmHg at 25°C
• Refractive Index: 1.54
• Boiling Point: 470.3 °C at 760 mmHg
• Flash Point: 252.3 °C
• Density: 1.115g/cm³
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 334.25079494
• Heavy Atom Count: 24
• Complexity: 517

Purity/Quality:

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

3α,21-Dihydroxy-5α-pregnan-20-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4C(=O)CO)C)O
• Uses: 3α,21-Dihydroxy-5α-pregnan-20-one (THDOC) has been used:as an γ-aminobutyric acid type A receptor (γ-GABAA) agonist in voltage-clamp measurements studies in Xenopus oocytesto test its effect on the spike-wave discharges (SWD) finasteride-treated ratsin electrophysiological studies with dentate granule cells (DGCs) post controlled cortical impact (CCI) -induced brain injury

Technology Process of 3beta,5alpha-Tetrahydrodeoxycorticosterone

There total 22 articles about 3beta,5alpha-Tetrahydrodeoxycorticosterone 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: 96.0%

3β-hydroxy-20-oxo-5α-pregnan-21-yl acetate (96611-83-5) → tetrahydroxydeoxycorticosterone (567-02-2)

Guidance literature:

With potassium carbonate; In methanol; for 0.5h; Ambient temperature;

DOI:10.1021/jm00168a008

Reference yield: 76.0%

(3β,5α)-21-bromo-3-hydroxypregnan-20-one (51296-50-5,95341-20-1) → (3β,5α)-3,21-dihydroxypregnan-20-one (567-02-2,567-03-3,800-10-2,33995-21-0,51548-31-3,108450-73-3,567-01-1)

Guidance literature:

With water; sodium hydroxide; for 0.5h;

DOI:10.1021/jm300317k

Reference yield: 44.0%

deoxycorticosterone acetate (56-47-3) → (3β,5α)-3,21-dihydroxypregnan-20-one (567-02-2,567-03-3,800-10-2,33995-21-0,51548-31-3,108450-73-3,567-01-1) + 5α-pregnan-21-ol-3,20-dione (298-36-2)

Guidance literature:

In ethanol; at 24 - 26 ℃; for 96h; Penicillium decumbens ATCC 10436, potato dextrose broth;

DOI:10.1016/0039-128X(95)00071-W

upstream raw materials:

21,21-bis-benzyloxy-3β-hydroxy-pregn-5-en-20-one

deoxycorticosterone acetate

ethanol

Pregnenolone

Refernces

• 1、 Purdy, Robert H.,Morrow, Leslie A.,Blinn, James R.,Paul, Steven M.. "Synthesis, Metabolism, and Pharmacological Activity of 3α-Hydroxy Steroids Which Potentiate GABA-Receptor-Mediated Chloride Ion Uptake in Rat Cerebral Cortical Synaptoneurosomes". . p. 1572 - 1581. Retrieved 1990.
• 2、 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". . p. 4431 - 4445. Retrieved 2012/09/11.