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C8753

Sigma-Aldrich

Cholesteryl arachidonate

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

Sinónimos:

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

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About This Item

Fórmula empírica (notación de Hill):
C47H76O2
Número de CAS:
604-34-2
Peso molecular:
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

Certificados de análisis (COA)

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M Aviram et al.
Free radical biology & medicine, 26(7-8), 892-904 (1999-05-08)
Human serum paraoxonase (PON1) can protect low density lipoprotein (LDL) from oxidation induced by either copper ion or by the free radical generator azo bis amidinopropane hydrochloride (AAPH). During LDL oxidation in both of these systems, a time-dependent inactivation of
J M Smaby et al.
Biochemistry, 20(4), 724-730 (1981-02-17)
Surface pressure--area isotherms for binary mixtures of cholesteryl octanoate, elaidate, stearate, oleate, linoleate, linolenate, and arachiodonate in mixtures with dioleoyllecithin, triolein, oleic acid, and oleoyl alcohol were measured at 24 degrees C. Analysis of the pressure and area characteristics as
Huiyong Yin et al.
Analytical biochemistry, 313(2), 319-326 (2003-02-28)
Autoxidation of polyunsaturated fatty acids and esters leads to a complex mixture containing hydroperoxides and cyclic peroxides. The oxidation mixture of cholesteryl arachidonate, which has been characterized by a variety of mass spectrometry techniques, was subject to analysis by conventional
D A Wiebe et al.
Clinical chemistry, 30(3), 352-356 (1984-03-01)
Esterolytic activity of three enzymic cholesterol reagents was evaluated with use of human serum-based reference materials. Primary cholesterol standards were used to calibrate the enzymic methods, and incomplete cholesteryl ester hydrolysis was measured as the bias between the enzymic cholesterol
Huiyong Yin et al.
The Journal of biological chemistry, 279(5), 3766-3776 (2003-11-05)
Free radical-initiated lipid autoxidation in low density lipoprotein (LDL) has been implicated in the pathogenesis of atherosclerosis. Oxidation of the lipid components of LDL leads to a complex mixture of hydroperoxides, bicyclic endoperoxides, monocyclic peroxides, and serial cyclic peroxides. The
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