Cholesteryl Linoleate Hydroperoxides

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. 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. Cholesteryl ester hydroperoxides may be transferred from LDL to HDL, reduced to the corresponding hydroxides, and cleared via the liver.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 solution in ethanol. Solubility: DMF: >50 mg/ml (from 13(R)-HODE cho, DMSO: >50 mg/ml (from 13(R)-HODE cho, Ethanol: >50 mg/ml (from 13(R)-HODE cho, PBS pH 7.2: <20 µg/ml. lambdamax: 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?,. InChi Key: NGQQXGUUARXKDS-SNXHTGDHSA-N. Side Chain Carbon Sum: 18:2.