19-Hydroxycholesterol

Base Information

• Chemical Name: 19-Hydroxycholesterol
• CAS No.: 561-63-7
• Molecular Formula: C₂₇H₄₆O₂
• Molecular Weight: 402.661
• DSSTox Substance ID: DTXSID40971482
• Nikkaji Number: J128.858J
• Wikidata: Q76390075
• Metabolomics Workbench ID: 34557
• ChEMBL ID: CHEMBL1908008
• Mol file: 561-63-7.mol

Synonyms:19-hydroxycholesterol;cholest-5-ene-3beta,19-diol

Chemical Property of 19-Hydroxycholesterol

Chemical Property:

• Vapor Pressure: 5.68E-13mmHg at 25°C
• Melting Point: 153-155?C
• Boiling Point: 519.7°Cat760mmHg
• Flash Point: 217°C
• PSA: 40.46000
• Density: 1.03g/cm³
• LogP: 6.36110
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 7.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 6
• Exact Mass: 402.349780706
• Heavy Atom Count: 29
• Complexity: 610

Purity/Quality:

99.3% ^*data from raw suppliers

19-HydroxyCholesterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)CO)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)CO)C
• Uses: A metabolite of Cholesterol. Cholesterol oxidation product having cytotoxicity effects.

Technology Process of 19-Hydroxycholesterol

There total 15 articles about 19-Hydroxycholesterol 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: 87.0%

3β-acetoxycholest-5-en-19-ol (750-59-4) → 19-hydroxycholesterol (561-63-7)

Guidance literature:

With sodium carbonate; In methanol; at 20 ℃;

DOI:10.1016/S0009-3084(99)00005-5

Reference yield:

(1aR,3aS,3bS,5aR,6R,8aS,8bS,10aR)-6-((R)-1,5-Dimethyl-hexyl)-3a-hydroxymethyl-5a-methyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-10-ol (1104-72-9) → 19-hydroxycholesterol (561-63-7)

Guidance literature:

With perchloric acid; In 1,4-dioxane;

Reference yield:

(1aR,3aS,3bS,5aR,6R,8aS,8bS,10aR)-6-((R)-1,5-Dimethyl-hexyl)-10-hydroxy-5a-methyl-tetradecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene-3a-carboxylic acid methyl ester (137436-12-5,137436-13-6) → 19-hydroxycholesterol (561-63-7)

Guidance literature:

Multi-step reaction with 2 steps

1: LAH

2: aq. HClO₄ / dioxane

With lithium aluminium tetrahydride; perchloric acid; In 1,4-dioxane;

upstream raw materials:

(1aR,3aS,3bS,5aR,6R,8aS,8bS,10aR)-6-((R)-1,5-Dimethyl-hexyl)-3a-hydroxymethyl-5a-methyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalen-10-ol

3,5-cyclocholesterol

3β-acetoxycholest-5-en-19-ol

cholesterol

Refernces

• 1、 Rabinowitz, Michael H.,Djerassi, Carl. "Biosynthetic studies of marine lipids. 39.1 19-norsterols: The course of c-19 methyl elimination". . p. 304 - 317. Retrieved 2007/10/02.