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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:
303-43-5
Peso molecolare:
651.10
Beilstein:
2343071
Numero CE:
206-142-1
Numero MDL:
MFCD00003645
Codice UNSPSC:
12352211
ID PubChem:
24893143
NACRES:
NA.77

Origine biologica

synthetic (organic)

Livello qualitativo

200

Saggio

≥98% (HPLC; detection at 205 nm)

Stato

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)

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Certificati d'analisi (COA)

Lot/Batch Number
SLCK4979
SLCJ4258
SLCG4671
SLCG1686
SLCF0418

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Cholesteryl caprylate United States Pharmacopeia (USP) Reference Standard

USP

1132001

Cholesteryl caprylate

Cholesteryl-26,26,26,27,27,27-d6 oleate-1,2,3,7,8,9,10-13C7 98 atom % D, 99 atom % 13C, 97% (CP)

Sigma-Aldrich

729671

Cholesteryl-26,26,26,27,27,27-d6 oleate-1,2,3,7,8,9,10-13C7

Oleyl oleate ≥99%

Sigma-Aldrich

O3380

Oleyl oleate

Colesterolo Sigma Grade, ≥99%

Sigma-Aldrich

C8667

Colesterolo

CHOLESTERYL MYRISTATE AldrichCPR

S455342

CHOLESTERYL MYRISTATE

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
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)
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.
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
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Articoli

Cholesterol Esterification

Cholesterol undergoes esterification to improve transport. Cholesterol esters are more easily packaged into the interior of lipoproteins - increasing the quantity that can be readily transported in the blood stream.

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