Mar 1, 1997

Photo-initiated peroxidation of lipids in micelles by azaaromatics

Lipids
L R BarclayC D Edwards

Abstract

The monoazaaromatics, pyridine (1), hexyl nicotinate (2), and quinoline (3) and diazaaromatics, pyrimidine (4) and purine (5), readily act as photo-initiators for the peroxidation of methyl linoleate in 0.50 M SDS at 37 degrees C giving free radical chain oxidations of linoleate. Quantitative kinetic runs on the order in substate, RH, and in the rate of chain initiation, Ri, showed that the classical rate law for autoxidation, -d[O2]/dt = (kp/(2 kt 1/2))[RH] x Ri 1/2, is applicable to these photo-initiated oxidations. The oxidizability of methyl linoleate under these conditions is 2.92 x 10(-2) M-1/2 s-1/2. These peroxidations were inhibited by chromanol phenolic antioxidants of the vitamin E class, such as lipid-soluble 2,2,5,7,8-pentamethyl-6-hydroxychroman (PMHC) and water-soluble 2-carboxy- 2,5,7,8-tetramethyl-6-hydroxychroman (Trolox) and derived rate constants for inhibition of peroxidation were kinh (PMHC) = 4.35 x 10(4) M-1 s-1 and k(inh) (Trolox) = 2.81 x 10(4) M-1 s-1 during inhibited oxidation of methyl linoleate photo-initiated by 4. The products from photo-initiated peroxidation of methyl linoleate by 1 through 5 were determined by reduction and high-performance liquid chromatography analyses to be the 9- and 13-po...Continue Reading

  • References8
  • Citations3

Mentioned in this Paper

Pyridines
Antioxidant Effect
Quinolines
Free Radicals
Pyridine, hydrogen iodide
Linoleic Acids
Hexyl nicotinate
Lipid Peroxidation
Trolox C
Quinoline hydrochloride

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