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Merck

C0289

Cholesteryl linoleate

≥98% (HPLC; detection at 205 nm)

Synonym(s):

3β-Hydroxy-5-cholestene 3-linoleate, 5-Cholesten-3β-ol 3-linoleate, Cholesteryl 9,12-octadecadienoate, Cholesteryl octadecadienoate

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About This Item

Empirical Formula (Hill Notation):
C45H76O2
CAS Number:
604-33-1
Molecular Weight:
649.08
NACRES:
NA.77
PubChem Substance ID:
24892247
UNSPSC Code:
12352211
EC Number:
210-065-9
MDL number:
MFCD00003644

Product Name

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

InChI key

NAACPBBQTFFYQB-LJAITQKLSA-N

InChI

1S/C45H76O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1

SMILES string

CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC=C2C1)[C@H](C)CCCC(C)C

biological source

synthetic (organic)

assay

≥98% (HPLC; detection at 205 nm)

form

powder

functional group

ester

shipped in

ambient

storage temp.

−20°C

Quality Level

200

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Application

Cholesteryl linoleate was cosonicated with cholesterol to prepare dispersions were prepared to study the cholesterol to phospholipid ratio in red blood cell membrane. It was used as HPLC standard in the analysis of rat liver lipoproteins.

Biochem/physiol Actions

Cholesteryl linoleate is a major 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.
The most abundant cholesteryl ester in low density lipoprotein (LDL).

Packaging

Sealed ampule

Preparation Note

Cholesteryl linoleate yields clear, colorless solution in chloroform at 100 mg/ml.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000513933
0000513932
0000513931
0000513931
0000513932

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R Mashima et al.
Journal of lipid research, 41(1), 109-115 (2000-01-11)
We have previously reported the detection of cholesteryl ester hydroperoxides, consisting mainly of cholesteryl linoleate hydroperoxides (Ch18:2-OOH), at nm levels in plasma from healthy humans (Y. Yamamoto and E. Niki, 1989. Biochem. Biophys. Res. Commun. 165: 988-993). To elucidate their
L Kritharides et al.
Journal of lipid research, 39(12), 2394-2405 (1998-11-30)
Cholesteryl linoleate hydroperoxide (CLOOH) and hydroxide (CLOH) are present in human atheroma. The intracellular metabolism of low density lipoprotein (LDL)-derived CLOOH and CLOH remain undefined because extensive free radical-mediated LDL oxidation, which modifies LDL apolipoprotein B sufficiently to allow endocytosis
Ota Samek et al.
Sensors (Basel, Switzerland), 10(9), 8635-8651 (2010-01-01)
Algae are becoming a strategic source of fuels, food, feedstocks, and biologically active compounds. This potential has stimulated the development of innovative analytical methods focused on these microorganisms. Algal lipids are among the most promising potential products for fuels as
Factors influencing the lipid composition and fluidity of red cell membranes in vitro: production of red cells possessing more than two cholesterols per phospholipid.
R A Cooper et al.
Biochemistry, 17(2), 327-331 (1978-01-24)
J K Christison et al.
Journal of lipid research, 36(9), 2017-2026 (1995-09-01)
This study examines the cholesteryl ester transfer protein (CETP)-mediated exchange of cholesteryl linoleate hydroperoxide (Ch18:2-OOH) and cholesteryl linoleate hydroxide (Ch18:2-OH) between low density lipoprotein (LDL) and high density lipoprotein (HDL). When [3H]Ch18:2-OOH- and [3H]18:2-OH-labeled LDL were incubated at 37 degrees
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