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C8753

Sigma-Aldrich

Cholesteryl arachidonate

≥95% (HPLC; detection at 205 nm), viscous liquid

Synonym(s):

3β-Hydroxy-5-cholestene 3-arachidonate, 5-Cholesten-3β-ol 3-arachidonate, Cholesteryl eicosatetraenoate

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About This Item

Empirical Formula (Hill Notation):
C47H76O2
CAS Number:
604-34-2
Molecular Weight:
673.11
MDL number:
MFCD00056441
UNSPSC Code:
12352211
PubChem Substance ID:
24893099
NACRES:
NA.77

assay

≥95% (HPLC; detection at 205 nm)

form

viscous liquid

color

clear

functional group

ester

shipped in

dry ice

storage temp.

−20°C

SMILES string

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

InChI

1S/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+

InChI key

IMXSFYNMSOULQS-SXXSVFILSA-N

Application

Cholesteryl arachidoante was oxidized and used to study the biological effects.

Biochem/physiol Actions

Cholesteryl arachidonate is a cholesterol ester found associated with the neutral core of low density lipoprotein. Receptor-LDL complexes are taken up by lysosomes and hydrolyzed to release cholesterol from the esters. The enzyme acid cholesteryl ester hydrolase is responsible for the hydrolysis of cholesteryl esters; a defective enzyme can result in the formation of atherosclerotic lesions in humans.

Preparation Note

Cholesteryl arachidonate is a clear, colorless viscous liquid in chloroform.

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

Certificates of Analysis (COA)

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The mobility of cholesteryl esters in native and reconstituted low density lipoprotein as monitored by nuclear magnetic resonance spectroscopy.
P A Kroon et al.
The Journal of biological chemistry, 256(11), 5340-5344 (1981-06-10)
N P Odushko et al.
Kardiologiia, 24(10), 90-93 (1984-10-01)
The blood serum of coronary and liver patients was shown to display a similar increase in the relative levels of cholesterololeate and a some what less marked elevation in the content of cholesterol esters with saturated fatty acids. The cholesterollinoleate
C Pollaud et al.
Biochimica et biophysica acta, 1259(3), 211-219 (1995-12-07)
The aim of our work was to evaluate the influence of native low density lipoproteins (LDL) and LDL chemically modified by acetylation (acLDL) on incorporation and release of arachidonic acid (AA) in rat peritoneal macrophages. Compared to a control group
J L Kerwin et al.
Lipids, 31(11), 1179-1188 (1996-11-01)
Lagenidium giganteum, a facultative parasite of mosquito larvae, cannot synthesize sterols, and requires an exogenous source of these lipids in order to enter its reproductive cycle. This parasite grows vegetatively in the absence of sterols, but requires cholesterol or structurally
V Schlotte et al.
Free radical biology & medicine, 25(7), 839-847 (1998-11-21)
Oxidative modification of low density lipoprotein (LDL) is implicated in the early development of atherosclerosis. In the present study, attention has been focused toward the potential protective effects of uric acid and purine-based chemical analogues in copper-promoted oxidative changes to
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Articles

Cholesterol Esterification

Cholesterol undergoes esterification to improve transport. Cholesterol esters are more easily packaged into the interior of lipoproteins - increasing the quantity that can be readily transported in the blood stream.

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