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Cholesteryl Linoleate Hydroperoxides

Cayman Chemical Item Number 48001

Cholesteryl Linoleate Hydroperoxides

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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

Background Reading

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

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).

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).

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).

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).

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).

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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
Bulk Contact
Cart Total $0.00

This product is available in custom sizes and/or larger quantities.

Please contact our Sales Department for a quote or to purchase.

Pricing updated 2012-05-26. Prices are subject to change without notice.

To ask for assistance with one of our products please contact a Technical Support Scientist.

Warning This product is not for human or veterinary use.

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Atherosclerosis Product Pack
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