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C9253

Cholesteryl oleate

≥98% (HPLC; detection at 205 nm)

Synonym(s):

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

Empirical Formula (Hill Notation):
C45H78O2
CAS Number:
303-43-5
Molecular Weight:
651.10
UNSPSC Code:
12352211
NACRES:
NA.77
PubChem Substance ID:
24893143
EC Number:
206-142-1
Beilstein/REAXYS Number:
2343071
MDL number:
MFCD00003645
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biological source

synthetic (organic)

Quality Level

200

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

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

WGK 3

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000511032
0000511030
0000511030
0000511032
0000511040

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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)
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