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C8753

Cholesteryl arachidonate

Name: Cholesteryl arachidonate
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

24893099

UNSPSC Code:

12352211

MDL number:

MFCD00056441

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Quality Level

200

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

Related Categories

Biochemicals

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

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000508479

0000479962

0000456991

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Acetylated low density lipoprotein inhibits the incorporation of arachidonic acid in phospholipids with a concomitant increase of cholesterol arachidonate in rat peritoneal macrophages.

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

Sterol and steryl ester regulation of phospholipase A2 from the mosquito parasite Lagenidium giganteum.

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

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)

Influence of incomplete cholesteryl ester hydrolysis on enzymic measurements of cholesterol.

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

Specificity of the ferrous oxidation of xylenol orange assay: analysis of autoxidation products of cholesteryl arachidonate.

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

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Global Trade Item Number

SKU	GTIN
C8753-25MG	04061833076163
C8753-10MG	04061833076156

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