24,25-Dihydrolanosterol

Base Information

• Chemical Name: 24,25-Dihydrolanosterol
• CAS No.: 79-62-9
• Deprecated CAS: 483329-03-9
• Molecular Formula: C₃₀H₅₂O
• Molecular Weight: 428.742
• UNII: 9H273A8B2X
• DSSTox Substance ID: DTXSID101000181
• Nikkaji Number: J40.430F
• Wikipedia: Dihydrolanosterol
• Wikidata: Q27103510
• Metabolomics Workbench ID: 34394
• ChEMBL ID: CHEMBL4213010
• Mol file: 79-62-9.mol

Synonyms:(3beta,20S)-isomer of lanostenol;(3beta,5xi,14xi)-isomer of lanostenol;24,25-dihydrolanosterol;5 alpha-lanost-8-en-3 beta-ol;lanostenol

Chemical Property of 24,25-Dihydrolanosterol

Chemical Property:

• Vapor Pressure: 5.88E-12mmHg at 25°C
• Melting Point: 162 °C
• Boiling Point: 496.9°C at 760 mmHg
• PKA: 15.16±0.70(Predicted)
• Flash Point: 221.3°C
• PSA: 20.23000
• Density: 0.97g/cm³
• LogP: 8.55900
• XLogP3: 9.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 428.401816278
• Heavy Atom Count: 31
• Complexity: 716

Purity/Quality:

97% ^*data from raw suppliers

Dihydrolanosterol, Technical Grade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CCCC(C)C1CCC2(C1(CCC3=C2CCC4C3(CCC(C4(C)C)O)C)C)C
• Isomeric SMILES: C[C@H](CCCC(C)C)[C@H]1CC[C@@]2([C@@]1(CCC3=C2CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O)C)C)C
• Uses: Dihydrolanosterol, is a derivative of Lanosterol (L174580). It is also one of cytochrome P 450 lanosterol 14α-demethylase (CYP51), which is shown to have an important role in regulating meiosis and reproduction.

Technology Process of 24,25-Dihydrolanosterol

There total 53 articles about 24,25-Dihydrolanosterol 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: 100.0%

tirucallol (79-63-0) → 24,25-dihydrolanosterol (79-62-9,564-60-3,6198-06-7,6593-55-1,13879-09-9,39701-94-5,59684-64-9,78821-82-6)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In dichloromethane; at 20 ℃; for 24h; under 2585.81 Torr;

DOI:10.1016/j.jinorgbio.2014.03.017

Reference yield: 91.0%

dihydroagnosterol (2644-75-9) → 24,25-dihydrolanosterol (79-62-9,564-60-3,6198-06-7,6593-55-1,13879-09-9,39701-94-5,59684-64-9,78821-82-6)

Guidance literature:

With lithium; ethylamine; isopropylamine; In diethyl ether; at -78 ℃; for 5h;

DOI:10.1016/0040-4039(94)88450-1

Reference yield: 48.0%

15-oxolanost-8-en-3β-yl pivaloate (309958-24-5) → 24,25-dihydrolanosterol (79-62-9,564-60-3,6198-06-7,6593-55-1,13879-09-9,39701-94-5,59684-64-9,78821-82-6)

Guidance literature:

15-oxolanost-8-en-3β-yl pivaloate; With hydrazine hydrate; In diethylene glycol; at 150 ℃; for 4h;

With potassium hydroxide; In water; diethylene glycol; at 230 ℃; for 5h;

upstream raw materials:

diethyl ether

lanosterol

cholesterol

lanosterol

Downstream raw materials:

γ-lanosterol

lanost-8-en-3-one

3β-acetoxylanost-8-ene

3β-benzoyloxy-lanost-8-ene

Refernces

α-Selective thermal glycosidation of rhamnosyl and mannosyl chlorides

10.1016/S0040-4039(00)97381-7

The research documented in the literature focuses on the selective thermal glycosylation of various alcohols using 2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl chloride and 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl chloride to produce α-glycosides with high selectivity. The study builds on previous work involving thermal glycosidation with glucosyl or xylosyl chlorides but introduces a significant improvement in stereoselectivity, particularly with sterically hindered alcohols. The key chemicals involved in this research include the rhamnosyl and mannosyl chlorides as glycosyl donors, various alcohols such as cholesterol, cholestanol, dihydrolanosterol, and others as acceptors, and in some experiments, N,N,N',N'-tetramethylurea (TMU) as an acid scavenger. The process is notable for its simplicity, safety, and economy, as it does not require hazardous metal salts or solvents, making it a practical and environmentally friendly method for glycosylation.

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