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C9253 Sigma-Aldrich

Cholesteryl oleate

≥98% (HPLC; detection at 205 nm)

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

  • CAS Number 303-43-5

  • Empirical Formula (Hill Notation) C45H78O2

  • Molecular Weight 651.10

  •  Beilstein/REAXYS Number 2343071

  •  EC Number 206-142-1

  •  MDL number MFCD00003645

  •  PubChem Substance ID 24893143

  •  NACRES NA.77

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Properties

Related Categories Biochemicals and Reagents, Cell Biology, Cholesteric, Cholesterol and Derivatives, Lipids,
Quality Level   200
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

Description

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.

Packaging

1 g in serum bottle

100, 250, 500 mg in serum bottle

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

BACSMLS Online Plate Map

BACSMLS compounds are conveniently provided at 5µg per well, enough for multiple injections. These are high purity (>95%) compounds supplied in an economical, ready to use format. Compounds are arran...
Keywords: Metabolites

Cholesterol Esterification

To more efficiently transport both dietary and synthesized cholesterol, it is converted to cholesteryl esters. Free cholesterol can be taken up by lipoproteins, but is confined to the outer surface o...
BioFiles 2007, 2.7, 10.
Keywords: Biofiles, Catalysis

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

TLC Analysis of Cholesteryl Esters on HPTLC Silica Gel 60 F 254 with Concentrating Zone (analyte set 2)

From our library of Articles, Sigma-Aldrich presents TLC Analysis of Cholesteryl Esters on HPTLC Silica Gel 60 F 254 with Concentrating Zone (analyte set 2)
Keywords: Thin layer chromatography

Peer-Reviewed Papers
15

References

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92210 Timestrip Plus 0 °C
06693 Timestrip Plus -20 °C

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