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Merck

C8753

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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Acerca de este artículo

Fórmula empírica (notación de Hill):
C47H76O2
Número CAS:
Peso molecular:
673.11
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352211
MDL number:

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Nombre del producto

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

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+

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 key

IMXSFYNMSOULQS-SXXSVFILSA-N

assay

≥95% (HPLC; detection at 205 nm)

form

viscous liquid

color

clear

functional group

ester

shipped in

dry ice

storage temp.

−20°C

Quality Level

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Este artículo
C9253C0289C2800
functional group

ester

functional group

ester

functional group

ester

functional group

ester

assay

≥95% (HPLC; detection at 205 nm)

assay

≥98% (HPLC; detection at 205 nm)

assay

≥98% (HPLC; detection at 205 nm)

assay

≥98% (HPLC; detection at 258 nm)

shipped in

dry ice

shipped in

ambient

shipped in

ambient

shipped in

ambient

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

form

viscous liquid

form

powder

form

powder

form

crystalline powder

Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

Application

Cholesteryl arachidoante was oxidized and used to study the biological effects.[1][2]

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.[3] 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.[4]

Preparation Note

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

Clase de almacenamiento

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves


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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)
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
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
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
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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Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

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