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

Key Documents

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Product Name

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

200

Related Categories

Biochemicals

Chemistry & Biochemicals

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1 of 4

This Item	C9253	C0289	C2800
Sigma-Aldrich C8753 Cholesteryl arachidonate	Sigma-Aldrich C9253 Cholesteryl oleate	Sigma-Aldrich C0289 Cholesteryl linoleate	Sigma-Aldrich C2800 Cholesteryl phenylacetate
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.

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

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Certificates of Analysis (COA)

Lot/Batch Number

0000508479

0000479962

0000456991

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Microquantification of cholesterol and cholesteryl esters in rat peritoneal macrophages by reverse-phase high-performance liquid chromatography.

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)

Identification of a novel class of endoperoxides from arachidonate autoxidation.

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

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

Human serum paraoxonase (PON 1) is inactivated by oxidized low density lipoprotein and preserved by antioxidants.

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

Flow cytometric measurement of ceroid accumulation in macrophages.

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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