1-(3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-hydroxyethanone

Base Information

• Chemical Name: 1-(3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-hydroxyethanone
• CAS No.: 600-63-5
• Molecular Formula: C21H34 O4
• Molecular Weight: 350.499
• NSC Number: 112288
• Wikidata: Q110184551
• Mol file: 600-63-5.mol

Synonyms:NSC112288;NSC-112288;FT-0771240;FT-0771917

Chemical Property of 1-(3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-hydroxyethanone

Chemical Property:

• Vapor Pressure: 1.65E-05mmHg at 25°C
• Melting Point: 221-224 °C
• Boiling Point: 326.4°C at 760 mmHg
• PKA: 12.98±0.10(Predicted)
• Flash Point: 165.4°C
• PSA: 77.76000
• Density: 1.166g/cm³
• LogP: 2.53840
• Storage Temp.: -20°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• 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

Allotetrahydrocorticosterone ^*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
• Uses: Allotetrahydrocorticosterone displays the profile of a safe topical anti-inflammatory compound. Also, it strongly inhibits 11β-HSD2 and 11β-HSD1 dehydrogenase activity.

Technology Process of 1-(3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-hydroxyethanone

There total 7 articles about 1-(3,11-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-hydroxyethanone 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:

corticosterone-21-acetate (1173-26-8) → 5α-pregnan-3α,11β,21-triol-20-one (600-63-5)

Guidance literature:

Multi-step reaction with 5 steps

1: H₂ / Pd-C / ethyl acetate

2: H₂ / Raney-Ni / dioxane

3: Py

5: aq. KHCO₃

With pyridine; hydrogen; potassium hydrogencarbonate; palladium on activated charcoal; nickel; In 1,4-dioxane; ethyl acetate;

DOI:10.1016/0039-128X(63)90025-4

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) → 5α-pregnan-3α,11β,21-triol-20-one (600-63-5)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Raney-Ni / dioxane

2: Py

4: aq. KHCO₃

With pyridine; hydrogen; potassium hydrogencarbonate; nickel; In 1,4-dioxane;

DOI:10.1016/0039-128X(63)90025-4

Reference yield:

21-acetoxy-3β,11β-dihydroxy-5α-pregnan-20-one (57717-95-0) → 5α-pregnan-3α,11β,21-triol-20-one (600-63-5)

Guidance literature:

With p-toluenesulfonyl chloride; folgenden mit DMF und mit wss.KHCO₃;

DOI:10.1016/0039-128X(63)90025-4

upstream raw materials:

21-acetoxy-3β,11β-dihydroxy-5α-pregnan-20-one

21-Acetoxy-3α-formyloxy-20-oxo-5α-pregnanol-(11β)

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

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