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C9253

Sigma-Aldrich

Cholesteryl oleate

≥98% (HPLC; detection at 205 nm)

Sinonimo/i:

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

Formula empirica (notazione di Hill):
C45H78O2
Numero CAS:
Peso molecolare:
651.10
Beilstein:
2343071
Numero CE:
Numero MDL:
Codice UNSPSC:
12352211
ID PubChem:
NACRES:
NA.77

Origine biologica

synthetic (organic)

Saggio

≥98% (HPLC; detection at 205 nm)

Forma fisica

powder

Punto di fusione

44-47 °C (lit.)

Gruppo funzionale

ester

Condizioni di spedizione

ambient

Temperatura di conservazione

−20°C

Stringa SMILE

[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
RJECHNNFRHZQKU-RMUVNZEASA-N

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Applicazioni

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.

Azioni biochim/fisiol

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.

Nota sulla preparazione

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

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


Certificati d'analisi (COA)

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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
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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.
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Articoli

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

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