Cholesteryl linoleate

Base Information

• Chemical Name: Cholesteryl linoleate
• CAS No.: 604-33-1
• Molecular Formula: C45H76 O2
• Molecular Weight: 649.097
• DSSTox Substance ID: DTXSID00889357
• Wikidata: Q76511841
• Mol file: 604-33-1.mol

Synonyms:Cholest-5-en-3-ol(3b)-,(9Z,12Z)-9,12-octadecadienoate (9CI); Cholest-5-en-3-ol (3b)-, 9,12-octadecadienoate,(Z,Z)-; Cholesterol, linoleate (8CI); Linoleic acid, cholesteryl ester (6CI);Cholesteryl linoleate; NSC 18183

Chemical Property of Cholesteryl linoleate

Chemical Property:

• Appearance/Colour: White powder.
• Melting Point: 41-42.5 °C
• Boiling Point: 677.3±44.0 °C(Predicted)
• Flash Point: 113 °C
• PSA: 26.30000
• Density: 0.96±0.1 g/cm3(Predicted)
• LogP: 13.75310
• Storage Temp.: −20°C
• XLogP3: 16.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 21
• Exact Mass: 662.60018173
• Heavy Atom Count: 48
• Complexity: 1070

Purity/Quality:

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

Cholesteryl linoleate ≥98% (HPLC; detection at 205 nm) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC=CCC=CCCCCCCCC(=O)OC1CCC2(C3CCC4(C(CCC4C3(CC=C2C1)C)C(C)CCCC(C)C)C)C
• Isomeric SMILES: CCCCC/C=C\C/C=C\CCCCCCCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@@]4([C@H](CC[C@H]4[C@@]3(CC=C2C1)C)[C@H](C)CCCC(C)C)C)C
• Uses: Cholesteryl linoleate was cosonicated with cholesterol to prepare dispersions were prepared to study the cholesterol to phospholipid ratio in red blood cell membrane. It was used as HPLC standard in the analysis of rat liver lipoproteins.

Technology Process of Cholesteryl linoleate

There total 6 articles about Cholesteryl linoleate 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: 91.9%

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) + cholesterol (57-88-5) → cholesterol linoleate (604-33-1)

Guidance literature:

With pseudomonas lipase; In water; at 40 ℃; for 24h; Enzymatic reaction;

DOI:10.1007/s11746-999-0164-6

Reference yield:

linoleyl chloride (7459-33-8) + cholesterol (57-88-5) → cholesterol linoleate (604-33-1)

Guidance literature:

at 70 - 80 ℃;

Reference yield:

linoleic acid (60-33-3,116745-32-5,26085-09-6,64080-88-2,7049-66-3,949900-18-9,60476-23-5,6144-28-1,67922-65-0,89718-18-3) → cholesterol linoleate (604-33-1)

Guidance literature:

Multi-step reaction with 2 steps

1: SOCl₂

2: 70 - 80 °C

With thionyl chloride;

upstream raw materials:

linoleyl chloride

cholesterol

linoleic acid

cholesterol

Downstream raw materials:

(R,S)-coriolic acid

(10E,12Z)-9-hydroxy-10,12-octadecadienoic acid

(8E,12Z)-10-hydroxy-8,12-octadecadienoic acid

(9Z,13E)-12-hydroxy-9,13-octadecadienoic acid