(S)-2,3-Epoxysqualene

Base Information

• Chemical Name: (S)-2,3-Epoxysqualene
• CAS No.: 54910-48-4
• Molecular Formula: C₃₀H₅₀O
• Molecular Weight: 426.726
• Nikkaji Number: J648.097G
• Wikidata: Q27453274
• Metabolomics Workbench ID: 28718
• Mol file: 54910-48-4.mol

Synonyms:(3S)-oxidosqualene;oxidosqualene;squslene oxide

Chemical Property of (S)-2,3-Epoxysqualene

Chemical Property:

• Boiling Point: 164-165 °C(Press: 10 Torr)
• Density: 0.882±0.06 g/cm3(Predicted)
• Storage Temp.: ?20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 10.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 15
• Exact Mass: 426.386166214
• Heavy Atom Count: 31
• Complexity: 677

Purity/Quality:

98%,99%, ^*data from raw suppliers

3(S)-Oxidosqualene ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=CCCC(=CCCC(=CCCC=C(C)CCC=C(C)CCC1C(O1)(C)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/CC/C(=C/CC/C=C(\C)/CC/C=C(\C)/CC[C@H]1C(O1)(C)C)/C)/C)C
• Uses: 3(S)-Oxidosqualene is used in the synthesis of lanosterol, a precursor to cholesterol.

Technology Process of (S)-2,3-Epoxysqualene

There total 32 articles about (S)-2,3-Epoxysqualene 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%

squalene monobromohydrin: 3-bromo-2,6,10,15,19,23-hexamethyl-6,10,14,18,22-tetracosapentaen-2-ol (all E) (65746-05-6) → 2,3-Oxidosqualene (14050-42-1,54910-48-4,54910-49-5,54910-50-8,55058-26-9,55058-27-0,132199-42-9,138809-21-9,147731-51-9,7200-26-2,54274-53-2,71606-52-5)

Guidance literature:

With potassium carbonate; In methanol; at 20 ℃; for 2h;

Reference yield: 62.0%

(3R)-(6E,10E,14E,18E)-2,3-dihydroxy-2,3-dihydrosqualene (63976-65-8) → squalene 2,3(S)-oxide (54910-48-4,54274-53-2,71606-52-5)

Guidance literature:

With dmap; triethylamine; p-toluenesulfonyl chloride; In dichloromethane; at 20 ℃; for 96h;

DOI:10.1002/adsc.200800180

Reference yield: 62.0%

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene (111-02-4) → 2,3-Oxidosqualene (14050-42-1,54910-48-4,54910-49-5,54910-50-8,55058-26-9,55058-27-0,132199-42-9,138809-21-9,147731-51-9,7200-26-2,54274-53-2,71606-52-5)

Guidance literature:

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene; With N-Bromosuccinimide; water; In tetrahydrofuran; for 0.75h;

With methanol; potassium carbonate; for 0.333333h;

DOI:10.1002/adsc.200800180

upstream raw materials:

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

squalene monobromohydrin: 3-bromo-2,6,10,15,19,23-hexamethyl-6,10,14,18,22-tetracosapentaen-2-ol (all E)

(S)-2-fluoro-3-hydroxysqualene

(S)-3-((E)-5-Bromo-3-methyl-pent-3-enyl)-2,2-dimethyl-oxirane

Downstream raw materials:

2,3,22,23-Dioxidosqualene

2,6,10,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaene

2,3-Dihydroxy-2,3-dihydrosqualene

Lanosterol

Refernces

• 1、 Yu, Wenjing,Sun, Kaiju,Zhang, Liying,Wan, Xilin,Chen, Changbao,Su, Rui,Liu, Yifei,Wang, Hongfeng,Yang, Hongmei. "Investigation of the Effects of Squalene and Squalene Epoxides on the Homeostasis of Coenzyme Q10 in Rats by UPLC-Orbitrap MS". . . Retrieved 2020/08/05.
• 2、 Colombo, Eleonora,Biocotino, Michele,Frapporti, Giulia,Randazzo, Pietro,Christodoulou, Michael S.,Piccoli, Giovanni,Polito, Laura,Seneci, Pierfausto,Passarella, Daniele. "Nanolipid-trehalose conjugates and nano-assemblies as putative autophagy inducers". . . Retrieved 2019/09/10.