Organotellurium compounds as efficient retarders of lipid peroxidation in methanol.
Diaryl tellurides were found efficiently to retard azo-initiated lipid peroxidation of linoleic acid in methanol. The most efficient compounds, 31 and 39, contained one and two hydroxyl groups, respectively, in the para positions and methyl groups in all four positions ortho to tellurium. As determined by the values of n.kinh, these materials were as effective retarders of lipid peroxidation as vitamin E. Contrary to the conventional antioxidants examined, diaryl tellurides were found to inhibit peroxidation for long times, seemingly with an autocatalytic mechanism. Diaryl tellurides were found to be partially oxidized during the peroxidation. The reduction of tellurium (IV) compounds to the divalent state during the conditions of the experiment is discussed. The reactivity of some diaryl chalcogenides toward 2,2-diphenyl-1-picrylhydrazyl (DPPH) in methanol was studied. All compounds investigated were less reactive than vitamin E. One of the most active organotellurium compounds, bis(4-aminophenyl) telluride, reacted considerably faster with DPPH than the corresponding selenide or sulfide. It was concluded that mechanisms involving both hydrogen atom transfer and electron transfer were operative in the reaction of organotellurides with DPPH.
Engman
L
L
Uppsala University, Department of Organic Chemistry, Sweden.
Persson
J
J
Vessman
K
K
Ekström
M
M
Berglund
M
M
Andersson
C M
CM
D000975:Antioxidants / Q000494:pharmacology*; D015764:Bepridil / Q000031:analogs & derivatives / Q000737:chemistry; D001713:Biphenyl Compounds; D019787:Linoleic Acid; D008041:Linoleic Acids / Q000737:chemistry; D015227:Lipid Peroxidation / Q000187:drug effects*; D000432:Methanol; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry / Q000494:pharmacology*; D010851:Picrates; D013329:Structure-Activity Relationship; D014810:Vitamin E / Q000494:pharmacology
C096489:4-hydroxy-2,6-dimethylphenyl-2,6-dimethylphenyl telluride; D000975:Antioxidants; D001713:Biphenyl Compounds; D008041:Linoleic Acids; D009942:Organometallic Compounds; D010851:Picrates; C096488:bis(4-hydroxy-2,6-dimethylphenyl)telluride; D014810:Vitamin E; D015764:Bepridil; D019787:Linoleic Acid; C004931:1,1-diphenyl-2-picrylhydrazyl; D000432:Methanol