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Merck

C9253

Sigma-Aldrich

Cholesteryl oleate

≥98% (HPLC; detection at 205 nm)

Sinónimos:

3β-Hydroxy-5-cholestene 3-oleate, 5-Cholesten-3β-ol 3-oleate, Cholesteryl cis-9-octadecenoate, Oleic acid cholesteryl ester

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About This Item

Fórmula empírica (notación de Hill):
C45H78O2
Número de CAS:
Peso molecular:
651.10
Beilstein/REAXYS Number:
2343071
EC Number:
MDL number:
UNSPSC Code:
12352211
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

assay

≥98% (HPLC; detection at 205 nm)

form

powder

mp

44-47 °C (lit.)

functional group

ester

shipped in

ambient

storage temp.

−20°C

SMILES string

[H]\C(CCCCCCCC)=C(/[H])CCCCCCCC(=O)O[C@H]1CC[C@@]2(C)C(C1)=CC[C@]3([H])[C@]2([H])CC[C@]4(C)[C@]([H])(CC[C@@]34[H])[C@H](C)CCCC(C)C

InChI

1S/C45H78O2/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/h14-15,26,35-36,38-42H,7-13,16-25,27-34H2,1-6H3/b15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1

InChI key

RJECHNNFRHZQKU-RMUVNZEASA-N

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Application

Cholesteryl oleate was used to study the ability of silicone hydrogel contact lenses to absorb tear lipids, cholesterol and cholesterol esters. It was also used in the development of amperometric cholesterol biosensors.

Biochem/physiol Actions

Cholesterol in plasma is present in an esterified form such as Cholesteryl oleate. The liver is a primary source of cholesteryl oleate that enriches the LDL particles when released into plasma. The secretion of lipoproteins enriched with cholesteryl oleate has close correlation with the pathogenesis of coronary artery atherosclerosis.

Preparation Note

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)


Certificados de análisis (COA)

Busque Certificados de análisis (COA) introduciendo el número de lote del producto. Los números de lote se encuentran en la etiqueta del producto después de las palabras «Lot» o «Batch»

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Los clientes también vieron

J A Hamilton et al.
The Journal of biological chemistry, 258(21), 12821-12826 (1983-11-10)
The incorporation of cholesteryl oleate and triolein into phospholipid vesicles was studied in cosonicated mixtures of 94 weight % egg phosphatidylcholine and 6 weight % neutral lipid (0-6% triolein and 6-0% cholesteryl oleate). 13C NMR spectroscopy was used to quantitate
L L Rudel et al.
The Journal of clinical investigation, 100(1), 74-83 (1997-07-01)
Relationships among plasma lipoprotein cholesterol, cholesterol secretion by the isolated, perfused liver, and coronary artery atherosclerosis were examined in African green monkeys fed diets containing cholesterol and 35% of calories as fat enriched in polyunsaturated, monounsaturated, or saturated fatty acids.
Marta Overchuk et al.
ACS nano, 13(4), 4560-4571 (2019-03-28)
Lipoprotein mimetic nanostructures, which consist of an amphiphilic lipid shell, a hydrophobic core, and an apolipoprotein mimetic peptide, serve as a versatile platform for the design of drug delivery vehicles as well as the investigation of supramolecular assemblies. Porphyrin incorporation
Design of an Interference-Free Cholesterol Amperometric Biosensor Based on the Electrosynthesis of Polymeric Films of Diaminonaphthalene Isomers
Garcia-Ruiz E et al
Electroanalysis, 16, 497-504 (2004)
Chendong Yang et al.
The Journal of clinical investigation, 114(6), 813-822 (2004-09-17)
The ABC transporters ABCG5 and ABCG8 limit absorption and promote excretion of dietary plant sterols. It is not known why plant sterols are so assiduously excluded from the body. Here we show that accumulation of plant sterols in mice lacking

Artículos

Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

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