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Merck

C8753

Sigma-Aldrich

Cholesteryl arachidonate

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

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C47H76O2
CAS-Nummer:
Molekulargewicht:
673.11
MDL-Nummer:
UNSPSC-Code:
12352211
PubChem Substanz-ID:
NACRES:
NA.77

Qualitätsniveau

Assay

≥95% (HPLC; detection at 205 nm)

Form

viscous liquid

Farbe

clear

Funktionelle Gruppe

ester

Versandbedingung

dry ice

Lagertemp.

−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+

InChIKey

IMXSFYNMSOULQS-SXXSVFILSA-N

Anwendung

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

Biochem./physiol. Wirkung

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.

Angaben zur Herstellung

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

Lagerklassenschlüssel

10 - Combustible liquids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves


Analysenzertifikate (COA)

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Die Dokumentenbibliothek aufrufen

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
R Y Ball et al.
British journal of experimental pathology, 69(1), 43-56 (1988-02-01)
Murine resident peritoneal macrophages were maintained in cell culture in a medium containing 10% lipoprotein-deficient fetal calf serum to which various artificial lipoprotein particles (coacervates of lipid and bovine serum albumin) had been added. The uptake and intracellular fate of
N Araki et al.
Analytical biochemistry, 185(2), 339-345 (1990-03-01)
A simple and rapid method for the microquantification of cholesterol and cholesteryl esters by reverse-phase high performance liquid chromatography has been established. Comparison of elution patterns of authentic cholesterol and cholesteryl esters revealed that a mu Bondasphere reverse-phase C8 (300-A)
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
J V Hunt et al.
Atherosclerosis, 98(2), 229-239 (1993-01-25)
Flow cytometry has been examined as a method for quantitative measurement of the accumulation in macrophages of ceroid, an autofluorescent polymer composed of oxidised protein and lipid. Murine peritoneal macrophages were cultured in the presence of cholesteryl linoleate- or arachidonate-bovine

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