C0289

Cholesteryl linoleate

≥98% (HPLC; detection at 205 nm)

• Synonym(s): 3β-Hydroxy-5-cholestene 3-linoleate, 5-Cholesten-3β-ol 3-linoleate, Cholesteryl 9,12-octadecadienoate, Cholesteryl octadecadienoate
• Empirical Formula (Hill Notation): C₄₅H₇₆O₂
• CAS Number: 604-33-1
• Molecular Weight: 649.08
• NACRES: NA.77
• PubChem Substance ID: 24892247
• UNSPSC Code: 12352211
• EC Number: 210-065-9
• MDL number: MFCD00003644

Properties

• biological source: synthetic (organic)
• Quality Segment: 200
• assay: ≥98% (HPLC; detection at 205 nm)
• form: powder
• functional group: ester
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: CCCCC\C=C/C\C=C/CCCCCCCC(=O)O[C@H]1CC[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3CC=C2C1)[C@H](C)CCCC(C)C
• InChI: 1S/C45H76O2/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/h11-12,14-15,26,35-36,38-42H,7-10,13,16-25,27-34H2,1-6H3/b12-11-,15-14-/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1
• InChI key: NAACPBBQTFFYQB-LJAITQKLSA-N

Description

Application

Cholesteryl linoleate was cosonicated with cholesterol to prepare dispersions were prepared to study the cholesterol to phospholipid ratio in red blood cell membrane. It was used as HPLC standard in the analysis of rat liver lipoproteins.

Biochem/physiol Actions

Cholesteryl linoleate is a major cholesterol ester found associated with the neutral core of low density lipoprotein. Receptor-LDL complexes are taken up by lysosomes and hydrolyzed to release cholesterol from the esters. The enzyme acid cholesteryl ester hydrolase is responsible for the hydrolysis of cholesteryl esters; a defective enzyme can result in the formation of atherosclerotic lesions in humans.

The most abundant cholesteryl ester in low density lipoprotein (LDL).

Packaging

Sealed ampule

Preparation Note

Cholesteryl linoleate yields 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)