Cholesterylamine

Base Information

• Chemical Name: Cholesterylamine
• CAS No.: 2126-93-4
• Molecular Formula: C₂₇H₄₇N
• Molecular Weight: 385.677
• DSSTox Substance ID: DTXSID60943681
• Nikkaji Number: J1.102.117D
• ChEMBL ID: CHEMBL2420594
• Mol file: 2126-93-4.mol

Synonyms:3 beta-aminocholesterol;3-aminocholesterol;cholesterylamine;cholesterylamine, (3alpha)-isomer

Chemical Property of Cholesterylamine

Chemical Property:

• Vapor Pressure: 4.93E-09mmHg at 25°C
• Melting Point: 98 °C(Solv: methanol (67-56-1))
• Boiling Point: 470.8°Cat760mmHg
• PKA: 10?+-.0.70(Predicted)
• Flash Point: 234.5°C
• PSA: 26.02000
• Density: 0.96g/cm³
• LogP: 8.05540
• XLogP3: 8.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 5
• Exact Mass: 385.370850503
• Heavy Atom Count: 28
• Complexity: 591

Purity/Quality:

99%, ^*data from raw suppliers

(3β)-Cholest-5-en-3-amine ^*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)N)C)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)N)C)C
• Uses: (3β)-Cholest-5-en-3-amine enhances the magnetic susceptibility of lanthanide-chelating bicelles in bilayer. Also, it potentially shows a new mode of antiviral action in directly targeting the virus envelope and its biological functions.

Technology Process of Cholesterylamine

There total 27 articles about Cholesterylamine 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: 98.0%

3-β-azido-5-cholestene (1433-82-5) → cholest-5-en-3-amine (2126-93-4,14735-32-1,146727-50-6)

Guidance literature:

With n-butyllithium; dimethylamine borane; In tetrahydrofuran; at 65 ℃;

DOI:10.1016/0040-4039(95)00341-9

Reference yield: 96.0%

3β-azido-5-chlostene → 3β-amino-5-chlostene (2126-93-4,14735-32-1,146727-50-6)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 4 - 23 ℃; for 2 - 2.5h; Product distribution / selectivity;

Reference yield: 85.0%

cholesterol (57-88-5) → cholest-5-en-3-amine (2126-93-4,14735-32-1,146727-50-6)

Guidance literature:

With sodium azide; triphenylphosphine; In dichloromethane; N,N-dimethyl-formamide; at 90 ℃; for 7h;

DOI:10.1080/00397910008087402

upstream raw materials:

ethanol

sodium ethanolate

cholest-5-en-3β-yl-isopropyliden-amine

N-acetyl-cholest-5-en-3β-amine

Downstream raw materials:

3β-(4'-Chlorbutyramido)-5-cholesten

N-cholesteryl-2-nitrobenzenesulfonamide

N-[3-(tert-butoxycarbonylamino)propyl]-N-cholesteryl-2-nitrobenzenesulfonamide

tert-butyl 3-[(3-{(3β)-cholest-5-en-3-yl[(2-nitrophenyl)sulfonyl]amino}propyl)amino]-3-oxopropylcarbamate

Refernces

• 1、 Zou, Xiaodong,Zou, Jiaqi,Yang, Lizheng,Li, Guigen,Lu, Hongjian. "Thermal Rearrangement of Sulfamoyl Azides: Reactivity and Mechanistic Study". . p. 4677 - 4688. Retrieved 2017/05/12.
• 2、 -. "Bivalent multifunctional ligands targeting Aβ oligomers as treatment for Alzheimer's disease". Page/Page column 34; 35. . Retrieved 2016/03/12.