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C9253

Sigma-Aldrich

Cholesteryl oleate

≥98% (HPLC; detection at 205 nm)

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Synonym(s):
3β-Hydroxy-5-cholestene 3-oleate, 5-Cholesten-3β-ol 3-oleate, Cholesteryl cis-9-octadecenoate, Oleic acid cholesteryl ester
Empirical Formula (Hill Notation):
C45H78O2
CAS Number:
Molecular Weight:
651.10
Beilstein/REAXYS Number:
2343071
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

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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This Item
C0289C2800C6013
Cholesteryl oleate ≥98% (HPLC; detection at 205 nm)

C9253

Cholesteryl oleate

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

C0289

Cholesteryl linoleate

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

C2800

Cholesteryl phenylacetate

Cholesteryl hemisuccinate tris salt anionic detergent

C6013

Cholesteryl hemisuccinate tris salt

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (organic)

biological source

synthetic (organic)

functional group

ester

functional group

ester

functional group

ester

functional group

ester

form

powder

form

powder

form

crystalline powder

form

powder

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

shipped in

ambient

shipped in

ambient

shipped in

ambient

shipped in

ambient

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)


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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

Articles

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

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