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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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)

[Serum cholesterol ester level in patients with ischemic heart disease and liver disease].

N P Odushko et al.

Kardiologiia, 24(10), 90-93 (1984-10-01)

The blood serum of coronary and liver patients was shown to display a similar increase in the relative levels of cholesterololeate and a some what less marked elevation in the content of cholesterol esters with saturated fatty acids. The cholesterollinoleate

Cholesteryl hydroperoxyoctadecadienoate from oxidized low density lipoprotein inactivates platelet-derived growth factor.

M Van Heek et al.

The Journal of biological chemistry, 273(31), 19405-19410 (1998-07-25)

Both oxidized low density lipoprotein (ox-LDL) and platelet-derived growth factor (PDGF) have been implicated in the genesis of various inflammatory responses, including atherosclerosis. We demonstrate here a novel interaction between specific oxidized lipids derived from ox-LDL and PDGF. The lipid

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