Allopregnane-3alpha,20alpha-diol

Base Information

• Chemical Name: Allopregnane-3alpha,20alpha-diol
• CAS No.: 566-58-5
• Molecular Formula: C21H36 O2
• Molecular Weight: 320.516
• UNII: 97N2Q625GO
• DSSTox Substance ID: DTXSID40859115
• Nikkaji Number: J6.518H
• Wikipedia: Allopregnanediol
• Wikidata: Q27155400
• Metabolomics Workbench ID: 198466
• ChEMBL ID: CHEMBL1790205
• Mol file: 566-58-5.mol

Synonyms:566-58-5;Allopregnane-3alpha,20alpha-diol;5alpha-Pregnane-3alpha,20alpha-diol;Allopregnanediol;5-alpha-Pregnan-3-alpha, 20-alpha-diol;(3R,5S,8R,9S,10S,13S,14S,17S)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol;UNII-97N2Q625GO;CHEBI:81470;97N2Q625GO;(3alpha,5alpha,20S)-Prgnane-3,20-diol;Pregnane-3,20-diol, (3.alpha.,5.alpha.,20S)-;Allopregnan-3alpha,20alpha-diol;5?-PREGNANE-3?,20?-DIOL;Allopregnane-3.alpha.,20.alpha.-diol;5-Alpha-Pregnan-3-alpha,20-beta-diol;Allopregnane-3a,20a-diol;SCHEMBL3127007;CHEMBL1790205;DTXSID40859115;5alpha-pregnan-3alpha,20alpha-diol;Allopregnane-3-alpha,20-alpha-diol;AKOS027381316;(20S)3alpha,20-Dihydroxy-5alpha-pregnane;5 alpha -Pregnane-3 alpha ,20 alpha -diol;Prgnane-3,20-diol, (3alpha,5alpha,20S)-;(3-alpha,5-alpha,20S)-Pregnane-3,20-diol;C18042;ALLOPREGNANE-3.ALPHA.,20.ALPHA.-DIOL [MI];Q27155400;(1S,3aS,3bR,5aS,7R,9aS,9bS,11aS)-1-[(1S)-1-hydroxyethyl]-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-ol;(3R,8R,9S,10S,13S,14S,17S)-17-((S)-1-hydroxyethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-3-ol

Chemical Property of Allopregnane-3alpha,20alpha-diol

Chemical Property:

• Vapor Pressure: 1.98E-09mmHg at 25°C
• Melting Point: 240-242°C
• Boiling Point: 435.9°Cat760mmHg
• PKA: 15.05±0.20(Predicted)
• Flash Point: 191°C
• PSA: 40.46000
• Density: 1.053g/cm³
• LogP: 4.38700
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethanol (Slightly, Heated), Methanol (Slightly, Heated)
• XLogP3: 5.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 320.271530387
• Heavy Atom Count: 23
• Complexity: 463

Purity/Quality:

98%Min ^*data from raw suppliers

5α-Pregnane-3α,20α-diol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1CCC2C1(CCC3C2CCC4C3(CCC(C4)O)C)C)O
• Isomeric SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC[C@@H]4[C@@]3(CC[C@H](C4)O)C)C)O
• Uses: Progesterone metabolite Progesterone metabolite.

Technology Process of Allopregnane-3alpha,20alpha-diol

There total 28 articles about Allopregnane-3alpha,20alpha-diol 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%

PREGNANOLONE (128-20-1,128-21-2,516-54-1,516-55-2,4243-94-1,4320-08-5,4406-35-3,4406-37-5,4469-03-8,13089-85-5,13089-86-6,14615-01-1,21788-58-9,24557-99-1,25126-79-8,26961-00-2,36027-63-1,39845-99-3,40135-22-6,72691-57-7,81076-02-0,95118-68-6,110350-90-8) → pregnadiol (80-89-7,80-90-0,80-92-2,516-53-0,566-56-3,566-57-4,566-58-5,4406-36-4,4479-11-2,4707-80-6,6251-84-9,25908-35-4,28818-70-4,36027-66-4,38270-91-6,38270-97-2,52746-43-7,55569-11-4,55660-10-1,73745-18-3,98048-13-6,80-91-1)

Guidance literature:

With dimethylsulfide borane complex; (2S)-2-phenylglycinol; In tetrahydrofuran; for 0.4h; Ambient temperature;

Reference yield:

5β-pregn-16-en-3,20-dione (14884-07-2) → pregnadiol (80-89-7,80-90-0,80-92-2,516-53-0,566-56-3,566-57-4,566-58-5,4406-36-4,4479-11-2,4707-80-6,6251-84-9,25908-35-4,28818-70-4,36027-66-4,38270-91-6,38270-97-2,52746-43-7,55569-11-4,55660-10-1,73745-18-3,98048-13-6,80-91-1)

Guidance literature:

With ethanol; platinum; Hydrogenation;

DOI:10.1021/ja01860a016

Reference yield:

(20R)-20-hydroxy-5β-pregnan-3α-yl acetate (1900-68-1) → pregnadiol (80-89-7,80-90-0,80-92-2,516-53-0,566-56-3,566-57-4,566-58-5,4406-36-4,4479-11-2,4707-80-6,6251-84-9,25908-35-4,28818-70-4,36027-66-4,38270-91-6,38270-97-2,52746-43-7,55569-11-4,55660-10-1,73745-18-3,98048-13-6,80-91-1)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/ja01149a107

upstream raw materials:

Progesterone

pregnanedione

(20R)-20-hydroxy-5β-pregnan-3α-yl acetate

UC₁₀₁₃

Downstream raw materials:

dihydroprogesterone

5α-pregnan-3β,20α-diol

UC₁₀₂₄

20β-hydroxy-5α-pregnan-3-one

Refernces

• 1、 Jin, Yi,Mesaros, A. Clementina,Blair, Ian A.,Penning, Trevor M.. "Stereospecific reduction of 5β-reduced steroids by human ketosteroid reductases of the AKR (aldo-keto reductase) superfamily: Role of AKR1C1-AKR1C4 in the metabolism of testosterone and progesterone via the 5β-reductase pathway". supporting information; experimental part. p. 53 - 61. Retrieved 2012/06/15.
• 2、 Goendoes, Gyoergy,Orr, James C.. "Borane Reduction of the Steroid 20-Ketone Group in the Presence of Various Chiral β-Amino Alcohols". . p. 581 - 582. Retrieved 2007/10/02.