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Linoleate hydroperoxides are cleaved heterolytically into aldehydes by a Lewis acid in aprotic solvent

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Lipids

Abstract

Treatment of isomeric methyl linoleate hydroperoxides with a Lewis acid, BF3, in anhydrous ether led to a carbon-to-oxygen rearrangement that caused cleavage into shorter-chain aldehydes. Methyl (9Z,11E)-13-hydroperoxy-9,11-octadecadienoate afforded mainly hexanal and methyl (E)-12-oxo-10-dodecenoate, whereas methyl (10E,12Z)-9-hydroperoxy-10,12-octadecadienoate cleaved into 2-nonenal and methyl 9-oxononanoate. The 2 aldehydes obtained from each hydroperoxide isomer were uncharacteristic of the complex volatile profile usually obtained by β-scission of oxy radicals derived from homolysis of the hydroperoxide group. Rather, the reaction resembled the one catalyzed by the plant enzyme, hydroperoxide lyase.

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Authors and Affiliations

  1. Northern Regional Research Center, Agricultural Research Service, USDA, 61604, Peoria, IL

    H. W. Gardner & R. D. Plattner

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  1. H. W. Gardner
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  2. R. D. Plattner
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Gardner, H.W., Plattner, R.D. Linoleate hydroperoxides are cleaved heterolytically into aldehydes by a Lewis acid in aprotic solvent. Lipids 19, 294–299 (1984). https://doi.org/10.1007/BF02534458

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  • DOI: https://doi.org/10.1007/BF02534458

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