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C0289

Sigma-Aldrich

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:
Molecular Weight:
649.08
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

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

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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]

Packaging

100, 250 mg in ampule
1 g in ampule
Sealed ampule

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).

Preparation Note

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

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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