24-Methylenecholesterol

Base Information

• Chemical Name: 24-Methylenecholesterol
• CAS No.: 474-63-5
• Molecular Formula: C28H46 O
• Molecular Weight: 398.673
• UNII: SJ0718OYKX
• Nikkaji Number: J12.062F
• Wikidata: Q27109256
• Metabolomics Workbench ID: 34762
• ChEMBL ID: CHEMBL477971
• Mol file: 474-63-5.mol

Synonyms:24-methylenecholesterol;ergosta-5,24(28)-dien-3 beta-ol

Chemical Property of 24-Methylenecholesterol

Chemical Property:

• Vapor Pressure: 1.14E-11mmHg at 25°C
• Boiling Point: 490.3°Cat760mmHg
• Flash Point: 213.8°C
• PSA: 20.23000
• Density: 0.98g/cm³
• LogP: 7.55480
• XLogP3: 8.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 398.354866087
• Heavy Atom Count: 29
• Complexity: 659

Purity/Quality:

99% ^*data from raw suppliers

Ostreasterol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C(=C)CCC(C)C1CCC2C1(CCC3C2CC=C4C3(CCC(C4)O)C)C
• Isomeric SMILES: C[C@H](CCC(=C)C(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)C)C
• Uses: Ostreasterol is a marine steroid, and also a derivative compound of hydroxycholesterol (H918040), which functions as the main cholesterol elimination product of the brain and was found to be increased in serum of Alzheimer patients.

Technology Process of 24-Methylenecholesterol

There total 21 articles about 24-Methylenecholesterol 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: 86.0%

24-oxocholesterol (17752-16-8) + methyl-triphenylphosphonium iodide (2065-66-9) → 24-methylene cholesterol (474-63-5)

Guidance literature:

With sodium hydride; dimethyl sulfoxide; at 80 ℃; for 4h;

DOI:10.1016/S0039-128X(02)00059-4

Reference yield: 85.0%

24-oxocholesterol (17752-16-8) + Methyltriphenylphosphonium bromide (1779-49-3) → 24-methylene cholesterol (474-63-5)

Guidance literature:

With sodium hydride; In 1,4-dioxane; dimethyl sulfoxide; at 80 ℃; for 2h;

DOI:10.1016/j.steroids.2004.09.010

Reference yield: 67.0%

(1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-((R)-1,5-Dimethyl-4-methylene-hexyl)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene (68844-31-5) → 24-methylene cholesterol (474-63-5)

Guidance literature:

toluene-4-sulfonic acid; In 1,4-dioxane; water; at 80 ℃; for 1h;

DOI:10.1016/S0040-4039(00)84483-4

upstream raw materials:

(1aR,3aR,3bS,5aR,6R,8aS,8bS,10R,10aR)-6-((R)-1,5-Dimethyl-4-methylene-hexyl)-10-methoxy-3a,5a-dimethyl-hexadecahydro-cyclopenta[a]cyclopropa[2,3]cyclopenta[1,2-f]naphthalene

demosterol

S-Adenosyl-L-methionine

Methylenetriphenylphosphorane

Downstream raw materials:

24-methylene-cholest-4-ene-3-one

3β-(toluene-sulfonyl-(4)-oxy)-ergostadiene-(5,24(28))

24-methylenecholest-5-en-3β-ol-trimethylsilyl ether

Δ^5,24(28)-ergostadien-3β-ol