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C0289

Sigma-Aldrich

Cholesteryl linoleate

≥98% (HPLC; detection at 205 nm)

Synonyme(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

Formule empirique (notation de Hill):
C45H76O2
Numéro CAS:
604-33-1
Poids moléculaire :
649.08
Numéro CE :
210-065-9
Numéro MDL:
MFCD00003644
Code UNSPSC :
12352211
ID de substance PubChem :
24892247
Nomenclature NACRES :
NA.77

Source biologique

synthetic (organic)

Niveau de qualité

200

Pureté

≥98% (HPLC; detection at 205 nm)

Forme

powder

Groupe fonctionnel

ester

Conditions d'expédition

ambient

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

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.

Actions biochimiques/physiologiques

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).

Conditionnement

Sealed ampule

Notes préparatoires

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

Produit(s) apparenté(s)

Réf. du produit
Description
Tarif

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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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Cholesterol Esterification

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Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

Cholesterol Esterification

Cholesterol esterification enhances transport efficiency in lipoproteins for increased blood stream transport.

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