22-Oxocholesterol

Base Information

• Chemical Name: 22-Oxocholesterol
• CAS No.: 19243-30-2
• Molecular Formula: C₂₇H₄₄O₂
• Molecular Weight: 400.645
• UNII: 6PPD342RUR
• Nikkaji Number: J894.641H
• Mol file: 19243-30-2.mol

Synonyms:22-ketocholesterol;22-ketocholesterol, (3beta,20R)-isomer;22-oxocholesterol

Chemical Property of 22-Oxocholesterol

Chemical Property:

• Vapor Pressure: 3.08E-07mmHg at 25°C
• Melting Point: 142.5-143.5 °C
• Boiling Point: 508.5 °C at 760 mmHg
• PKA: 15.02±0.70(Predicted)
• Flash Point: 215.3 °C
• PSA: 37.30000
• Density: 1.03 g/cm³
• LogP: 6.56770
• XLogP3: 6.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 400.334130642
• Heavy Atom Count: 29
• Complexity: 663

Purity/Quality:

99% ^*data from raw suppliers

5-CHOLESTEN-3-BETA-OL-22-ONE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCC(=O)C(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)C(=O)CCC(C)C

Technology Process of 22-Oxocholesterol

There total 16 articles about 22-Oxocholesterol 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: 70.0%

3β-((tert-butyldimethylsilyl)oxy)-cholest-5-en-22-one → 22-ketocholesterol (19243-30-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1016/j.steroids.2016.12.003

Reference yield:

→ 22-ketocholesterol (19243-30-2)

Guidance literature:

With methanol; sodium carbonate;

Reference yield:

hydroxybisnorcholenic acid (566-77-8) → 22-ketocholesterol (19243-30-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

1.2: 20 °C / Inert atmosphere

2.1: 2,6-dimethylpyridine / dichloromethane / 0.5 h / -40 °C / Inert atmosphere

3.1: tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 24 h / 20 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.steroids.2016.12.003

upstream raw materials:

22(R)-Hydroxycholesterol

methyl 3β-hydroxy-23-bisnorchol-5-en-22-oate

i-pentyl bromide

(2β,20S)-3-<(tert-butyldimethylsilyl)oxy>pregn-5-ene-20-carboxaldehyde

Downstream raw materials:

3β-acetoxy-23,24-dinorchol-5-en-22-oyl chloride

3β-benzoylcholest-5-ene

3β-(toluene-4-sulfonyloxy)-cholest-5-en-22-one

Refernces

• 1、 Viktorsson, Elvar ?rn,Gabrielsen, Mari,Kumarachandran, Nugalya,Sylte, Ingebrigt,Rongved, P?l,?strand, Ove Alexander H?gmoen,Kase, Eili Tranheim. "Regulation of liver X receptor target genes by 22-functionalized oxysterols. Synthesis, in silico and in vitro evaluations". . p. 119 - 127. Retrieved 2017/01/13.