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Reaction of oxygen and unsaturated fatty acids

Abstract

Oxygen reacts readily with unsaturated fatty acids so that every time these compounds are handled there is a danger they will become contaminated with oxidation products. The products formed first are allylic hydroperoxides which are labile molecules that change rapidly to other compounds, some of which are highly flavorous. Sometimes these changes are desirable and may be promoted: frequently they are not and have to be inhibited. Instrumental procedures recently introduced—especially separation by high performance liquid chromatography and identification by1H and13C nuclear magnetic resonance spectroscopy—have led to a renewed interest in this subject. For the nonenzymic processes of autoxidation and photooxygenation we now have a better understanding of the routes leading to the first-formed allylic hydroperoxides and an improved appreciation of the structure of further oxidation products including dihydroperoxides and hydroperoxides which also contain one or more cyclic peroxide units. Direct chemical routes to several of these compounds have also been developed. Oxidation of linoleic acid by plant-derived lipoxygenases gives diene hydroperoxides similar to those produced by autoxidation, except that the former are optically active and the latter racemic. Enzymic oxidation of arachidonic acid and certain related C20 acids in animal systems produces a wide variety of prostaglandins, physiological properties. These compounds have been described as “tomorrow’s drugs”.

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Gunstone, F.D. Reaction of oxygen and unsaturated fatty acids. J Am Oil Chem Soc 61, 441–447 (1984). https://doi.org/10.1007/BF02678811

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Keywords

  • Hydroperoxide
  • Cocoa Butter
  • Methyl Oleate
  • Methyl Linolenate
  • Enzymic Oxidation