AMIDES OF SALICYLIC ACID – ARE NEW PERSPECTIVE ANTIOXIDANTS
In the N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS on the basis of the structure osalmid (2-hydroxy-N-(4-hydroxyphenyl)benzamide) was synthesized group substituted amides of salicylic acid having ortho-shielding tert-butyl substituents: 3-tert-butyl-N-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-ethyl-2-hydroxybenzamide, N-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl]-2-hydroxybenzamide, 3-tert-butyl-N-[3-(3,5-di-tert-butyl-4-hydroxyphenyl)propyl]-5-ethyl-2-hydroxybenzamide. Amides of salicylic acid in the oxidation of lipid substrates act by two mechanisms: react with peroxide radicals with the reaction rate constant k7 = (0,52 – 6,86)∙104 (M∙s)–1 and destroy hydroperoxides to form molecular products. Found that the introduction of shielding ortho-tert-butyl substituents and separation of aromatic moieties three methylene groups in the structures of the derivatives of salicylic acid leads to an increase in the antioxidant activity of the compounds, but this significantly reduces the reaction rate constant k7 interaction of antioxidants with peroxide radicals. It is likely that inhibitors of antiradical activity due to the presence in their chemical structure a phenolic hydroxyl group and the ability of hydroperoxides destruction associated with the presence of amide groups. The antioxidant properties of new perspective amides of salicylic acid are protected by patents for invention. The invention relates to the preparation of stabilizing the oxidation of lipids, lipid-food supplements, medical cosmetics, pharmaceuticals. The technical result of the invention is the expansion of the range of effective synthetic antioxidants, achieving high effects of inhibition at lower concentrations of the compounds.