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Cholesteryl arachidonate

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Cholesteryl arachidonate Basic information
Product Name:Cholesteryl arachidonate
Synonyms:CHOLESTERYL EICOSATETRAENOATE;3BETA-HYDROXY-5-CHOLESTENE 3-ARACHIDONATE;5-CHOLESTEN-3BETA-OL 3-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;(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid 3β-cholesteryl ester
CAS:604-34-2
MF:C47H76O2
MW:673.11
EINECS:610-261-8
Product Categories:
Mol File:604-34-2.mol
Cholesteryl arachidonate Structure
Cholesteryl arachidonate Chemical Properties
Melting point 19 °C
Boiling point 697.9±54.0 °C(Predicted)
density 0.97±0.1 g/cm3(Predicted)
storage temp. −20°C
solubility Chloroform (Slightly), Ethyl Acetate (Slightly)
form viscous liquid
color clear
Stability:Light Sensitive
InChIKeyIMXSFYNMSOULQS-SXXSVFILSA-N
SMILESCCCCC\C=C\C\C=C\C\C=C\C\C=C\CCCC(=O)OC1CCC2(C)C3CCC4(C)C(CCC4C3CC=C2C1)C(C)CCCC(C)C
Safety Information
WGK Germany 3
Storage Class10 - Combustible liquids
MSDS Information
Cholesteryl arachidonate Usage And Synthesis
DescriptionCholesteryl 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.
UsesCholesteryl arachidonate is a cholesterol ester found associated with the neutral core of low density lipoprotein.
DefinitionChEBI: A cholesterol ester obtained by the formal condensation of the hydroxy group in cholesterol with the carboxy group of arachidonic acid.
IC 50Human Endogenous Metabolite
References[1] BEHLING CHENG . Fundamental studies of adrenal retinoid-X-receptor: Protein isoform, tissue expression, subcellular distribution, and ligand availability[J]. Journal of Steroid Biochemistry and Molecular Biology, 2017, 171: Pages 110-120. DOI: 10.1016/j.jsbmb.2017.03.002
[2] SOO-HO CHOI. Polyoxygenated cholesterol ester hydroperoxide activates TLR4 and SYK dependent signaling in macrophages.[J]. PLoS ONE, 2013: e83145. DOI: 10.1371/journal.pone.0083145
[3] G.V. VAHOUNY. Cholesterol arachidonate as a prostaglandin precursor in adrenocortical cells[J]. Prostaglandins, 1978, 16 2: Pages 207-220. DOI: 10.1016/0090-6980(78)90022-9
[4] DANIEL C MA. Cholesteryl esters are elevated in the lipid fraction of bronchoalveolar lavage fluid collected from pediatric cystic fibrosis patients.[J]. PLoS ONE, 2015: e0125326. DOI: 10.1371/journal.pone.0125326
[5] DELMIS J. Placental lipid contents in preterm labor complicated by chorioamnionitis.[J]. Journal of Perinatal Medicine, 1989, 17 6: 417-422. DOI: 10.1515/jpme.1989.17.6.417
Cholesteryl arachidonate Preparation Products And Raw materials
Tag:Cholesteryl arachidonate(604-34-2) Related Product Information
Cholesteryl arachidonate, [arachidonate 5,6,8,9,11,12,14,15-3H] Cholesteryl arachidonate, [arachidonate-1-14C] Methyl arachidonate Arachidonic acid ethyl ester 5-Cholestene Arachidonic acid propyl ester Cholesteryl arachidonate Arachidonic acid ARACHIDONYL ALCOHOL APPROX 99