Allopregnane-3beta,17alpha-diol-20-one

Base Information

• Chemical Name: Allopregnane-3beta,17alpha-diol-20-one
• CAS No.: 570-54-7
• Molecular Formula: C21H34 O3
• Molecular Weight: 334.499
• European Community (EC) Number: 209-331-7
• UNII: 968OE017B8
• DSSTox Substance ID: DTXSID30878597
• Nikkaji Number: J6.535H
• Wikidata: Q27271891
• Metabolomics Workbench ID: 198480
• ChEMBL ID: CHEMBL3391718
• Mol file: 570-54-7.mol

Synonyms:570-54-7;Allopregnane-3beta,17alpha-diol-20-one;3-beta,17-alpha-Dihydroxy-5-alpha-pregnan-20-one;Wintersteiner's compound G;UNII-968OE017B8;EINECS 209-331-7;968OE017B8;SCHEMBL4101456;REICHSTEIN'S SUBSTANCE L;CHEMBL3391718;DTXSID30878597;Allopregnane-3b,17a-diol-20-one;Allopregnan-3beta,17-diol-20-one;1-[(3S,5S,8R,9S,10S,13S,14S,17R)-3,17-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,14,15,16-tetradecahydrocyclopenta[a]phenanthren-17-yl]ethanone;Allopregnane-3-beta,17-alpha-diol-20-one;3-beta,17-dihydroxy-5-alpha-pregnan-20-one;(3-beta,5-alpha)-3,17-Dihydroxypregnan-20-one;ALLOPREGNANE-3.BETA.,17.ALPHA.-DIOL-20-ONE;Q27271891;3.BETA.,17-DIHYDROXY-20-OXO-5.ALPHA.-PREGNANE;3.BETA.,17-DIHYDROXY-5.ALPHA.-PREGNAN-20-ONE;5-.ALPHA.-PREGNAN-3-.BETA., 17-DIOL-20-ONE;(3.BETA.,5.ALPHA.)-3,17-DIHYDROXYPREGNAN-20-ONE;ALLOPREGNANE-3.BETA.,17.ALPHA.-DIOL-20-ONE [MI]

Chemical Property of Allopregnane-3beta,17alpha-diol-20-one

Chemical Property:

• Vapor Pressure: 1.28E-10mmHg at 25°C
• Melting Point: 264-266°
• Boiling Point: 465.4°Cat760mmHg
• Flash Point: 249.4°C
• PSA: 57.53000
• Density: 1.123g/cm³
• LogP: 3.71010
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 334.25079494
• Heavy Atom Count: 24
• Complexity: 545

Purity/Quality:

99% ^*data from raw suppliers

3BETA,17ALPHA-DIOL-20-ONE-ALLOPREGNANE 95.00% ^*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)O
• Isomeric SMILES: CC(=O)[C@]1(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)O
• Uses: 5α-Pregnan-3β,17α-diol-20-one is a derivative of Pregnenolone(P712200) which is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. As such it is a prohormone. Pregnenolone is a GABAA antagonist and increases neurogenesis in the hippocampus. It is a modulator of cytochrome P 450-3A.

Technology Process of Allopregnane-3beta,17alpha-diol-20-one

There total 24 articles about Allopregnane-3beta,17alpha-diol-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:

Progesterone (57-83-0) → dihydroprogesterone (566-65-4) + androstanedione (846-46-8) + isopregnanolone (516-55-2) + 3β,17α-dihydroxy-5α-pregnan-20-one (570-54-7) + tetrahydroprogesterone (516-54-1) + 3α,17α-dihydroxy-5α-pregnan-20-one (6890-65-9)

Guidance literature:

With total testicular homogenate of adult Sprague-Dawley rats treated with 6, des-Gly-NH2¹⁰>LHRH ethylamide; Product distribution; metabolism, <3H>labelled, further: equine antibovine LH serum (JOAN-5-31-67);

DOI:10.1016/0039-128X(84)90054-0

Reference yield:

→ 3β,17α-dihydroxy-5α-pregnan-20-one (570-54-7)

Guidance literature:

With sodium hydroxide;

DOI:10.1021/ja01145a064 DOI:10.1021/ja01165a067

Reference yield:

5β-pregnene-(17(20)t)-diyl-(3β.20)-diacetate (17921-48-1,28507-81-5,49774-68-7,51014-05-2,51014-06-3,96092-31-8) + 5β-pregnene-(17(20)c)-diyl-(3β.20)-diacetate (1080507-42-1) → 3β,17α-dihydroxy-5α-pregnan-20-one (570-54-7)

Guidance literature:

With Perbenzoic acid; chloroform; anschliessende Hydrolyse;

upstream raw materials:

Perbenzoic acid

chloroform

5β-pregnene-(17(20)t)-diyl-(3β.20)-diacetate

5β-pregnene-(17(20)c)-diyl-(3β.20)-diacetate

Downstream raw materials:

3β-acetoxy-17-hydroxy-5α-pregnan-20-one

Refernces

• 1、 -. "17-Hydroxy-steroids". . . Retrieved 2008/06/13.
• 2、 Carmichael, Rejean,Belanger, Alain. "STUDY OF THE DIRECT EFFECT OF LHRH AGONIST ON TESTICULAR 17-HYDROXYLASE AND 5α-REDUCTASE ACTIVITIES IN NON-HYPOPHYSECTOMIZED ADULT RATS TREATED WITH AN ANTI-LUTEINIZING HORMONE SERUM". . p. 1 - 12. Retrieved 2007/10/02.