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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

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About This Item

Empirical Formula (Hill Notation):
C45H76O2
CAS Number:
604-33-1
Molecular Weight:
649.08
EC Number:
210-065-9
MDL number:
MFCD00003644
UNSPSC Code:
12352211
PubChem Substance ID:
24892247
NACRES:
NA.77

biological source

synthetic (organic)

Quality Level

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

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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. 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.

related product

Product No.
Description
Pricing

Storage Class Code

11 - 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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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R Mashima et al.
Journal of lipid research, 41(1), 109-115 (2000-01-11)
We have previously reported the detection of cholesteryl ester hydroperoxides, consisting mainly of cholesteryl linoleate hydroperoxides (Ch18:2-OOH), at nm levels in plasma from healthy humans (Y. Yamamoto and E. Niki, 1989. Biochem. Biophys. Res. Commun. 165: 988-993). To elucidate their
Factors influencing the lipid composition and fluidity of red cell membranes in vitro: production of red cells possessing more than two cholesterols per phospholipid.
R A Cooper et al.
Biochemistry, 17(2), 327-331 (1978-01-24)
Ota Samek et al.
Sensors (Basel, Switzerland), 10(9), 8635-8651 (2010-01-01)
Algae are becoming a strategic source of fuels, food, feedstocks, and biologically active compounds. This potential has stimulated the development of innovative analytical methods focused on these microorganisms. Algal lipids are among the most promising potential products for fuels as
Y Yamamoto
Free radical research, 33(6), 795-800 (2001-03-10)
Cholesteryl ester hydroperoxide (CE-OOH) and phosphatidylcholine hydroperoxide (PC-OOH) are the major primary oxidation products of lipoproteins. CE-OOH is present in human and rat plasmas while PC-OOH is undetectable. This is likely due to the enzymatic (plasma glutathione peroxidase) and the
L Kritharides et al.
Journal of lipid research, 39(12), 2394-2405 (1998-11-30)
Cholesteryl linoleate hydroperoxide (CLOOH) and hydroxide (CLOH) are present in human atheroma. The intracellular metabolism of low density lipoprotein (LDL)-derived CLOOH and CLOH remain undefined because extensive free radical-mediated LDL oxidation, which modifies LDL apolipoprotein B sufficiently to allow endocytosis
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