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.[1] It was used as HPLC standard in the analysis of rat liver lipoproteins.[2]

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.[3] 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.[4]

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)