Allopregnane-3beta,17alpha,21-triol-20-one

Base Information

• Chemical Name: Allopregnane-3beta,17alpha,21-triol-20-one
• CAS No.: 516-47-2
• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.499
• UNII: B2U92ZJ86E
• ChEMBL ID: CHEMBL2057979
• Metabolomics Workbench ID: 198478
• Nikkaji Number: J6.312F
• Mol file: 516-47-2.mol

Synonyms:REICHSTEIN'S SUBSTANCE P;516-47-2;Allopregnane-3beta,17alpha,21-triol-20-one;B2U92ZJ86E;CHEMBL2057979;Compound P;UNII-B2U92ZJ86E;Substance P (steroid);SCHEMBL752006;3beta,17alpha,21-Trihydroxy-5alpha-pregnan-20-one;UPTAPIKFKZGAGM-NWIHUDFTSA-N;Pregnan-20-one, 3,17,21-trihydroxy-, (3.beta.,5.alpha.)-;BDBM50388486;5alpha-Pregnan-3beta,17,21-triol-20-one;5-alpha-Pregnan-20-one, 3-beta,17,21-trihydroxy-;PREGNAN-20-ONE, 3.BETA.,17,21-TRIHYDROXY-;Q27274289;ALLOPREGNANE-3.BETA.,17.ALPHA.,21-TRIOL-20-ONE;(+)-ALLOPREGNANE-3.BETA.,17.ALPHA.,21-TRIOL-20-ONE;3.BETA.,17,21-TRIHYDROXY-5.ALPHA.-PREGNAN-20-ONE;5.ALPHA.-PREGNAN-20-ONE, 3.BETA.,17,21-TRIHYDROXY-;ALLOPREGNANE-3.BETA.,17.ALPHA.,21-TRIOL-20-ONE [MI];Pregnan-20-one, 3,17,21-trihydroxy-, (3-beta,5-alpha)-;3.BETA.,17.ALPHA.,21-TRIHYDROXY-5.ALPHA.-PREGNAN-20-ONE

Chemical Property of Allopregnane-3beta,17alpha,21-triol-20-one

Chemical Property:

• Vapor Pressure: 2.55E-12mmHg at 25°C
• Boiling Point: 505.1°Cat760mmHg
• Flash Point: 273.4°C
• PSA: 77.76000
• Density: 1.186g/cm³
• LogP: 2.68250
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 350.24570956
• Heavy Atom Count: 25
• Complexity: 562

Purity/Quality:

98%min ^*data from raw suppliers

3BETA,17ALPHA,21-TRIOL-20-ONE ALLOPREGNANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2CCC4(C3CCC4(C(=O)CO)O)C)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O

Technology Process of Allopregnane-3beta,17alpha,21-triol-20-one

There total 15 articles about Allopregnane-3beta,17alpha,21-triol-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: 78.0%

3β,21-diacetoxy-5α-pregnan-17α-ol-20-one (6003-22-1) → 3β,5α-Tetrahydro Reichstein's Substance S (68-60-0,601-01-4,601-03-6,7635-25-8,7694-32-8,97170-01-9,516-47-2)

Guidance literature:

With water; potassium hydroxide; In methanol; for 2h;

DOI:10.1016/j.steroids.2011.01.006

Reference yield: 34.0%

Cortexolone (152-58-9) → 3β,5α-Tetrahydro Reichstein's Substance S (68-60-0,601-01-4,601-03-6,7635-25-8,7694-32-8,97170-01-9,516-47-2) + 17α-21-dihydroxy-5-α-pregnane-3,20-dione (312-99-2)

Guidance literature:

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

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

Reference yield:

pregn-17(20)-ene-3β,21-diol (10291-89-1) → 3β,5α-Tetrahydro Reichstein's Substance S (68-60-0,601-01-4,601-03-6,7635-25-8,7694-32-8,97170-01-9,516-47-2)

Guidance literature:

Multi-step reaction with 3 steps

1: ammonium cerium (IV) nitrate / 50 - 60 °C

2: osmium(VIII) oxide; dihydrogen peroxide / water; acetone / 20 h / 20 °C

3: water; potassium hydroxide / methanol / 2 h

With osmium(VIII) oxide; ammonium cerium (IV) nitrate; water; dihydrogen peroxide; potassium hydroxide; In methanol; water; acetone;

DOI:10.1016/j.steroids.2011.01.006

upstream raw materials:

Cortexolone

digitonin

pregn-17(20)-ene-3β,21-diol

3β,21-diacetoxy-pregn-17(20)-ene

Downstream raw materials:

androstanedione

(20R)-5α-pregnanetetrol-(3β,17,20,21)