Cholesteryl Linoleate Hydroperoxides

Cayman Chemical Item Number 48001

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Description

Cholesteryl linoleate hydroperoxides are derived from the autoxidation of cholesteryl linoleate and contain a mixture of racemic 9- and 13-HpODE cholesteryl esters. Oxidative modification of LDL is suggested to play an important role in atherosclerosis. (±)9- and (±)13-HODE cholesteryl esters were originally extracted from atherosclerotic lesions and shown to be produced by Cu2+-catalyzed oxidation of LDL.1,2 Later studies determined that 15-LO, from rabbit reticulocytes and activated human monocytes, oxygenates cholesteryl linoleate to both 9- and 13-hydroperoxy linoleate cholesteryl esters.3,4 Cholesteryl ester hydroperoxides may be transferred from LDL to HDL, reduced to the corresponding hydroxides, and cleared via the liver.5,6

1. Brooks, C.J.W., Harland, W.A., Steel, G., et al. Lipids of human atheroma: Isolation of hydroxyoctadecadienoic acids from advanced aortal lesions. Biochim Biophys Acta 202 563-566 (1970).

2. Lenz, M.L., Hughes, H., Mitchell, J.R., et al. Lipid hydroperoxy and hydroxy derivatives in copper-catalyzed oxidation of low density lipoprotein. J Lipid Res 31 1043-1050 (1990).

3. Belkner, J., Wiesner, R., Kühn, H., et al. The oxygenation of cholesterol esters by the reticulocyte lipoxygenase. FEBS Lett 279 110-114 (1991).

4. Folcik, V.A., and Cathcart, M.K. Predominance of esterified hydroperoxy-linoleic acid in human monocyte-oxidized LDL. J Lipid Res 35 1570-1582 (1994).

5. Sattler, W., and Stocker, R. Greater selective uptake by Hep G2 cells of high-density lipoprotein cholesteryl ester hydroperoxides than of unoxidized cholesteryl esters. Biochem J 294 771-778 (1993).

6. Fluiter, K., Vietsch, H., Biessen, E.A.L., et al. Increased selective uptake in vivo and in vitro of oxidized cholesteryl esters from high-density lipoprotein by rat liver parenchymal cells. Biochem J 319 471-476 (1996).

Formal Name (±)-​9-​hydroperoxy-​10E,​12Z-​octadeca-​dienoic acid,​ cholesteryl ester; (±)-​13-​hydroperoxy-​9Z,​11E-​octade
Molecular Formula C45H76O4
Formula Weight 681.1
Formulation A solution in ethanol
Purity ≥98% hydroperoxide content
λmax 234 nm
ε 23
Stability 6 months
Storage -80°C
Shipping Dry ice in continental US; may vary elsewhere
SMILES
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CCCCC\C=C/C=C/C(OO)​CCCCCCCC(O[C@@H]​1CC2=CCC(C(CCC3C(CCCC(C)​C)​C)​[C@]​3(C)​CC4)​C4[C@@]​2(C)​CC1)​=O.CCCCCC(OO)​/C=C/C=C\CCCCCCCC(O[C@@H]​5CC6=CCC(C(CCC7C(C)​CCCC(C)​C)​[C@]​7(C)​CC8)​C8[C@@]​6(C)​CC5)​=O

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Cholesteryl Linoleate Hydroperoxides is available in the following screening library:

Size Price Quantity Subtotal
100 µg $22.00 $0.00
500 µg $99.00 $0.00
1 mg $176.00 $0.00
5 mg $770.00 $0.00
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Pricing updated 2015-05-22. Prices are subject to change without notice.

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Ann Arbor, Michigan 48108 USA

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