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Singlet oxygen oxidation of methyl linoleate: Isolation and characterization of the NaBH4-reduced products

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Lipids

Abstract

The mixture of diene hydroperoxides from methylene blue-sensitized oxidation of methyl linoleate was reduced with NaBH4 and the resulting alcohols were separated by high pressure liquid chromatography (HPLC). Four diene alcohols were isolated in approximately equal yields from adsorption and reversed phase HPLC; the isomers were identified as methyl esters of 9-hydroxy-10,12-, 10-hydroxy-8,12-, 12-hydroxy-9,13- and 13-hydroxy-9,11-octadecadienoate. Formation of equal yields of both conjugated and nonconjugated diene alcohols from methyl linoleate is characteristic of singlet oxygen oxidations. The detection of the easily separated nonconjugated isomer methyl 10-hydroxy-trans-8,cis-12-octadecadienoate from methyl linoleate is proposed as a test to probe the involvement of singlet oxygen in biological oxidations.

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Author notes

  1. Michael J. Thomas

    Present address: Department of Chemistry, Wake Forest University, 27109, Winston-Salem, NC

Authors and Affiliations

  1. Department of Chemistry, Louisiana State University, 70803, Baton Rouge, LA

    Michael J. Thomas & William A. Pryor

Authors
  1. Michael J. Thomas
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  2. William A. Pryor
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Additional information

A preliminary report of these results was presented at the 177th meeting of the American Chemical Society, Honolulu, HI, April 1–6, 1979; see abstracts of papers, paper No. ORGN-375.

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Thomas, M.J., Pryor, W.A. Singlet oxygen oxidation of methyl linoleate: Isolation and characterization of the NaBH4-reduced products. Lipids 15, 544–548 (1980). https://doi.org/10.1007/BF02534228

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  • DOI: https://doi.org/10.1007/BF02534228

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