Contains a mixture of racemic 9- and 13-HpODE cholesteryl esters
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Cholesteryl Linoleate Hydroperoxides

Item No. 48001

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(±)-9-hydroperoxy-10E,12Z-octadecadienoic acid, cholesteryl ester; (±)-13-hydroperoxy-9Z,11E-octadecadienoic acid, cholesteryl ester
Molecular Formula
C45H76O4
Formula Weight
681.1
Purity
≥98% hydroperoxide content
Formulation (Request formulation change)
A 1 mg/ml solution in ethanol
Solubility(Learn about Variance in Solubility)
DMF: >50 mg/ml (from 13(R)-HODE choDMSO: >50 mg/ml (from 13(R)-HODE choEthanol: >50 mg/ml (from 13(R)-HODE choPBS pH 7.2: <20 µg/ml
λmax
234 nm
SMILES
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
InChi Code
InChI=1S/2C45H76O4/c1-7-8-16-22-37(49-47)23-17-14-12-10-9-11-13-15-18-24-43(46)48-38-29-31-44(5)36(33-38)25-26-39-41-28-27-40(35(4)21-19-20-34(2)3)45(41,6)32-30-42(39)44;1-7-8-9-10-11-13-16-22-37(49-47)23-17-14-12-15-18-24-43(46)48-38-29-31-44(5)36(33-38)25-26-39-41-28-27-40(35(4)21-19-20-34(2)3)45(41,6)32-30-42(39)44/h12,14,17,23,25,34-35,37-42,47H,7-11,13,15-16,18-22,24,26-33H2,1-6H3;11,13,16,22,25,34-35,37-42,47H,7-10,12,14-15,17-21,23-24,26-33H2,1-6H3/b14-12-,23-17+;13-11-,22-16+/t2*35?,37?,38-,39?,40?,41?,42?,44-,45+/m00/s1
InChi Key
NGQQXGUUARXKDS-SNXHTGDHSA-N
Side Chain Carbon Sum
18:2
Shipping & Storage Information
Storage
-80°C
Shipping
Dry ice in continental US; may vary elsewhere
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    100 µg

    $32

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    1 mg

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    5 mg

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    Product 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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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(3), 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(6), 1043-1050 (1990).

    3. Belkner, J., Wiesner, R., Kühn, H., et al. The oxygenation of cholesterol esters by the reticulocyte lipoxygenase. FEBS Lett. 279(1), 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(9), 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(Pt 3), 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(Pt 2), 471-476 (1996).