Allopregnane-3beta,11beta,21-triol-20-one

Base Information

• Chemical Name: Allopregnane-3beta,11beta,21-triol-20-one
• CAS No.: 516-16-5
• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.499
• UNII: F590898GCA
• DSSTox Substance ID: DTXSID70199551
• Metabolomics Workbench ID: 198470
• Nikkaji Number: J6.305C
• Wikidata: Q27277661
• Mol file: 516-16-5.mol

Synonyms:516-16-5;Substance R;Reichstein's Substance R;Allopregnane-3beta,11beta,21-triol-20-one;Allocorticosterone, tetrahydro-;3beta,5alpha-Tetrahydrocorticosterone;5alpha-Pregnan-3beta,11beta,21-triol-20-one;F590898GCA;3beta-Allotetrahydrocorticosterone;UNII-F590898GCA;Corticosterone, 3-allotetrahydro-, (3beta)-;Allopregnane-3beta,11beta,21-triol-20-one [MI];SCHEMBL751635;3beta,11beta,21-Trihydroxy-5alpha-Pregnan-20-one;3beta,11beta,21-Trihydroxy-5alpha-Pregnane-20-one;5alpha-Pregnan-20-one, 3beta,11beta,21-trihydroxy-;DTXSID70199551;Pregnan-20-one, 3,11,21-trihydroxy-, (3beta,5alpha,11beta)-;3.BETA.-ALLOTETRAHYDROCORTICOSTERONE;3.BETA.,5.ALPHA.-TETRAHYDROCORTICOSTERONE;Q27277661;CORTICOSTERONE, 3-ALLOTETRAHYDRO-, (3.BETA.)-;ALLOPREGNANE-3.BETA.,11.BETA.,21-TRIOL-20-ONE;5.ALPHA.-PREGNAN-3.BETA.,11.BETA.,21-TRIOL-20-ONE;ALLOPREGNANE-3.BETA.,11.BETA.,21-TRIOL-20-ONE [MI];3.BETA.,11.BETA.,21-TRIHYDROXY-5.ALPHA.-PREGNAN-20-ONE;3.BETA.,11.BETA.,21-TRIHYDROXY-5.ALPHA.-PREGNANE-20-ONE;5.ALPHA.-PREGNAN-20-ONE, 3.BETA.,11.BETA.,21-TRIHYDROXY-;PREGNAN-20-ONE, 3,11,21-TRIHYDROXY-, (3.BETA.,5.ALPHA.,11.BETA.)-

Chemical Property of Allopregnane-3beta,11beta,21-triol-20-one

Chemical Property:

• Vapor Pressure: 1.62E-12mmHg at 25°C
• Melting Point: 202-204°
• Boiling Point: 509.6°C at 760 mmHg
• PKA: 12.98±0.10(Predicted)
• Flash Point: 276.1°C
• PSA: 77.76000
• Density: 1.18g/cm³
• LogP: 2.53840
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 350.24570956
• Heavy Atom Count: 25
• Complexity: 548

Purity/Quality:

98%min ^*data from raw suppliers

3BETA,11BETA,21TRIOL-20-ONE-ALLOPREGNANE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CCC(CC1CCC3C2C(CC4(C3CCC4C(=O)CO)C)O)O
• Isomeric SMILES: C[C@]12CC[C@@H](C[C@@H]1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@H]4C(=O)CO)C)O)O
• Uses: 3β,5α-Tetrahydrocorticosterone is used as a reactant in the 7α-hydroxylation of steroid 5-olefins by mold fungi.

Technology Process of Allopregnane-3beta,11beta,21-triol-20-one

There total 3 articles about Allopregnane-3beta,11beta,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:

→ 3α,11β,21-Trihydroxy-5β-pregnan-20-on (68-42-8,516-16-5,600-62-4,600-63-5,14149-83-8,27857-26-7,72075-11-7)

Guidance literature:

3α,21-Dihydroxy-5β-pregnan-11.20-dion-20-aethylenketal, 1)NaBH4 in Me. (RT, 36 h), 2)Δ mit wss.-methanol. H2SO4 (50 Min.);

Reference yield:

2-((5S,8S,9S,10S,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (884311-46-0) → 3β-allotetrahydrocorticosterone (516-16-5)

Guidance literature:

With 1,4-dioxane; nickel; Hydrogenation_.Behandeln mit wss.-methanol.K₂CO₃;

DOI:10.1021/ja01626a060

Reference yield:

RU 18748 (4004-68-6) → 3β-allotetrahydrocorticosterone (516-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: benzyl alcohol; HCl / nachfolgende Hydrierung an Palladium/Kohle und Acetylierung

2: Raney nickel; dioxane / Hydrogenation_.Behandeln mit wss.-methanol.K₂CO₃

With 1,4-dioxane; hydrogenchloride; nickel; benzyl alcohol;

DOI:10.1021/ja01626a060

upstream raw materials:

2-((5S,8S,9S,10S,11S,13S,14S,17S)-11-hydroxy-10,13-dimethyl-3-oxo-hexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

RU 18748