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Merck

C8753

Cholesteryl arachidonate

≥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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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

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This Item
C9253C0289C2800
Cholesteryl arachidonate ≥95% (HPLC; detection at 205 nm), viscous liquid

Sigma-Aldrich

C8753

Cholesteryl arachidonate

Cholesteryl oleate ≥98% (HPLC; detection at 205 nm)

Sigma-Aldrich

C9253

Cholesteryl oleate

Cholesteryl linoleate ≥98% (HPLC; detection at 205 nm)

Sigma-Aldrich

C0289

Cholesteryl linoleate

Cholesteryl phenylacetate ≥98% (HPLC; detection at 258 nm)

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

Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000508479
0000508479
0000479962
0000479962
0000456991

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Richard Harkewicz et al.
The Journal of biological chemistry, 283(16), 10241-10251 (2008-02-12)
Oxidation of low density lipoprotein (LDL) occurs in vivo and significantly contributes to the development of atherosclerosis. An important mechanism of LDL oxidation in vivo is its modification with 12/15-lipoxygenase (LO). We have developed a model of minimally oxidized LDL
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
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
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
View All Related Papers

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