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
• 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

Properties

• biological source: synthetic (organic)
• Quality Segment: 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

Description

Application

Cholesteryl oleate was used to study the ability of silicone hydrogel contact lenses to absorb tear lipids,[1] cholesterol and cholesterol esters.[2] 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.[3] 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.[4]

Preparation Note

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

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk: WGK 3
• ppe: Eyeshields, Gloves, type N95 (US)