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Merck

C0289

Cholesteryl linoleate

≥98% (HPLC; detection at 205 nm)

Sinónimos:

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

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Fórmula empírica (notación de Hill):
C45H76O2
Número CAS:
604-33-1
Peso molecular:
649.08
NACRES:
NA.77
PubChem Substance ID:
24892247
UNSPSC Code:
12352211
EC Number:
210-065-9
MDL number:
MFCD00003644

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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

Categorías relacionadas

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.

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

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Certificados de análisis (COA)

Lot/Batch Number
SLCL6238
SLCB7744
SLBX5428
SLBT3878
SLBS9356

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J Christison et al.
The Biochemical journal, 314 ( Pt 3), 739-742 (1996-03-15)
To test whether high-density lipoproteins (HDL) could aid in the removal in vivo of potentially atherogenic oxidized lipids, we perfused rat liver in situ with buffer supplemented with isolated human HDL containing small amounts of cholesteryl linoleate hydro(pero)xides [CH18:2-O(O)H]. Perfusion
Y Yamamoto
Free radical research, 33(6), 795-800 (2001-03-10)
Cholesteryl ester hydroperoxide (CE-OOH) and phosphatidylcholine hydroperoxide (PC-OOH) are the major primary oxidation products of lipoproteins. CE-OOH is present in human and rat plasmas while PC-OOH is undetectable. This is likely due to the enzymatic (plasma glutathione peroxidase) and the
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
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
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
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