Cholesteryl arachidonate

Base Information

• Chemical Name: Cholesteryl arachidonate
• CAS No.: 604-34-2
• Molecular Formula: C47H76O2
• Molecular Weight: 673.11
• UNII: USB7VS82GH
• DSSTox Substance ID: DTXSID701313431
• Nikkaji Number: J402.970D
• Wikidata: Q27156282
• Metabolomics Workbench ID: 34680
• Mol file: 604-34-2.mol

Synonyms:cholesteryl arachidonate;cholesteryl arachidonate eicosatetraenoate;cholesteryl arachidonate, (3beta)-(all Z)-isomer

Chemical Property of Cholesteryl arachidonate

Chemical Property:

• Vapor Pressure: 2.52E-19mmHg at 25°C
• Melting Point: 19 °C
• Refractive Index: 1.526
• Boiling Point: 697.9°C at 760 mmHg
• Flash Point: 376.9°C
• PSA: 26.30000
• Density: 0.97g/cm³
• LogP: 14.08530
• Storage Temp.: −20°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 15.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 21
• Exact Mass: 672.58453166
• Heavy Atom Count: 49
• Complexity: 1140

Purity/Quality:

98%Min ^*data from raw suppliers

Cholesteryl arachidonate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Lipids -> Unambiguous Lipids
• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)OC1CCC2(C3CCC4(C(C3CC=C2C1)CCC4C(C)CCCC(C)C)C)C
• Isomeric SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CC[C@@H]4[C@H](C)CCCC(C)C)C)C
• Description: Cholesteryl arachidonate is a cholesterol ester that is found in plasma and the adrenal gland. It is a component of low-density lipoprotein (LDL) and oxidiation of the arachidonate moiety contributes to macrophage activation and foam cell formation in atherosclerosis. Cholesteryl arachidonate undergoes hydrolysis to release arachidonic acid during ACTH-stimulated prostaglandin synthesis in rat adrenocortical cells. Levels of cholesteryl arachidonate are increased in the bronchoalveolar lavage fluid (BALF) in pediatric cystic fibrosis patients compared to healthy controls as well as in placentas of women with chorioamnionitis.
• Uses: Cholesteryl arachidonate is a cholesterol ester found associated with the neutral core of low density lipoprotein.

Technology Process of Cholesteryl arachidonate

There total 4 articles about Cholesteryl arachidonate 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: 92.1%

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) + cholesterol (57-88-5) → cholesteryl 5,8,11,14-eicosatetraenoate (604-34-2)

Guidance literature:

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

DOI:10.1007/s11746-999-0164-6

Reference yield:

Cholesteryl acetate (604-35-3) → cholesteryl 5,8,11,14-eicosatetraenoate (604-34-2)

Guidance literature:

With sodium ethanolate; at 80 - 90 ℃; under 20 - 30 Torr;

Reference yield:

arachidonic acid methyl ester (38575-18-7) + Cholesteryl acetate (604-35-3) → cholesteryl 5,8,11,14-eicosatetraenoate (604-34-2)

Guidance literature:

With sodium ethanolate; at 80 - 90 ℃; under 20 - 30 Torr;

upstream raw materials:

arachidonic acid methyl ester

Cholesteryl acetate

all cis 5,8,11,14-eicosatetraenoic acid

cholesterol

Refernces