604-34-2

Basic information

• Product Name: CHOLESTERYL ARACHIDONATE
• Synonyms: 3BETA-HYDROXY-5-CHOLESTENE 3-ARACHIDONATE;5-CHOLESTEN-3BETA-OL 3-ARACHIDONATE;CHOLESTERYL EICOSATETRAENOATE;CHOLESTERYL ARACHIDONATE;3β-hydroxy-5-cholestene 3-arachidonate;[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate;Cholesteryl arachidonic acid;3β-Hydroxy-5-cholestene 3-arachidonate, 5-Cholesten-3β-ol 3-arachidonate, Cholesteryl eicosatetraenoate
• CAS NO: 604-34-2
• Molecular Formula: C₄₇H₇₆O₂
• Molecular Weight: 673.11
• Mol File: 604-34-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 19 °C
• Boiling Point: 697.9°C at 760 mmHg
• Flash Point: 376.9°C
• Appearance: clear/
• Density: 0.97g/cm³
• Vapor Pressure: 2.52E-19mmHg at 25°C
• Refractive Index: 1.526
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• Stability: Light Sensitive
• CAS DataBase Reference: CHOLESTERYL ARACHIDONATE(CAS DataBase Reference)
• NIST Chemistry Reference: CHOLESTERYL ARACHIDONATE(604-34-2)
• EPA Substance Registry System: CHOLESTERYL ARACHIDONATE(604-34-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 604-34-2(Hazardous Substances Data)

Usage

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.

Definition

ChEBI: A cholesterol ester obtained by the formal condensation of the hydroxy group in cholesterol with the carboxy group of arachidonic acid.

InChI:InChI=1/C47H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h11-12,14-15,17-18,20-21,28,37-38,40-44H,7-10,13,16,19,22-27,29-36H2,1-6H3/b12-11+,15-14+,18-17+,21-20+/t38-,40+,41+,42-,43+,44+,46+,47-/m1/s1

Upstream product

• 38575-18-7 arachidonic acid methyl ester 
• 604-35-3 Cholesteryl acetate 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 57-88-5 cholesterol 

Relevant articles and documents

Enzymatic synthesis of steryl esters of polyunsaturated fatty acids

Steryl esters of long-chain fatty acids have water-holding properties, and polyunsaturated fatty acids (PUFA) have various physiological functions. Because steryl ester of PUFA can be expected to have both features, we attempted to synthesize steryl esters of PUFA by enzymatic methods. Among lipases used, Pseudomonas lipase was the most effective for the synthesis of cholesteryl docosahexaenoate. When a mixture of cholesterol/docosahexaenoic acid (3:1, mol/mol), 30% water, and 3000 units/g of lipase was stirred at 40 °C for 24 h, the esterification extent attained 89.5%. Under the same reaction conditions, cholesterol, cholestanol, and sitosterol were also esterified efficiently with docosahexaenoic, eicosapentaenoic, arachidonic, and γ-linolenic acids.