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604-34-2

604-34-2 Structure

604-34-2 Structure
IdentificationBack Directory
[Name]

CHOLESTERYL ARACHIDONATE
[CAS]

604-34-2
[Synonyms]

Cholesteryl arachidote
Cholesteryl arakidonate
Cholesterol arachidonate
CHOLESTERYL ARACHIDONATE
Cholesteryl arachidonic acid
CHOLESTERYL EICOSATETRAENOATE
5-Cholesten-3β-ol 3-arachidonate
5-CHOLESTEN-3BETA-OL 3-ARACHIDONATE
3β-hydroxy-5-cholestene 3-arachidonate
3BETA-HYDROXY-5-CHOLESTENE 3-ARACHIDONATE
(5Z,8Z,11Z,14Z)-5,8,11,14-Icosatetraenoic acid 3β-cholesteryl ester
Cholest-5-en-3-ol (3β)-, 3-[(5Z,8Z,11Z,14Z)-5,8,11,14-eicosatetraenoate]
3β-Hydroxy-5-cholestene 3-arachidonate, 5-Cholesten-3β-ol 3-arachidonate, Cholesteryl eicosatetraenoate
[(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
[EINECS(EC#)]

610-261-8
[Molecular Formula]

C47H76O2
[MDL Number]

MFCD00056441
[MOL File]

604-34-2.mol
[Molecular Weight]

673.11
Chemical PropertiesBack Directory
[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
[InChIKey]

IMXSFYNMSOULQS-SXXSVFILSA-N
[SMILES]

CCCCC\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 DataBack Directory
[WGK Germany ]

3
[Storage Class]

10 - Combustible liquids
Hazard InformationBack Directory
[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.
[IC 50]

Human 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
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