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Kinetic study of quenching reactions of singlet oxygen and scavenging reactions of free radicals by α-, β-, λ- and σ-tocopheramines in ethanol solution and micellar dispersion

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Lipids

Abstract

Quenching reactions of singlet oxygen and scavenging reactions of free radicals by α-, β-, λ- and σ-tocopheramines (Toc-amines) were investigated spectrophotometrically in ethanol and Triton X-100 micellar dispersions. The rate constants of quenching of singlet oxygen (k Q ) by α-, β-, λ- and σ-Toc-amines increased as the total electron donating capacity of the methyl groups at the aromatic ring increased. A plot of logk Q vs. peak oxidation potential (E p) was found to be linear and the slope was negative. Similar results were obtained for scavenging of a phenoxyl radical (PhO.). The results suggest that charge transfer plays an important role in these reactions. Thek Q values were found to be 1.30–2.57 times as large ask Q for α-tocopherol (α-Toc). Although α-Toc has the highest antioxidant activity among natural tocopherols and related phenols, Toc-amines also can serve as antioxidants.

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Abbreviations

DPBF:

2,5-diphenyl-3,4-benzofuran

EP:

3-(1,4-edipioxy-4-methyl-1,4-dihydro-1-naphthyl) propionic acid

E:

peak oxidation potential

k d :

rate constant of deactivation of singlet oxygen in pure solvent

k obsd :

pseudo-first-order rate constant for reaction between 2.6-di-t-butyl-4-(4-methoxyphenyl) phenoxyl and antioxidant

k Q :

rate constant of quenching of singlet oxygen by antioxidant

k s :

second-order rate constant for reaction between 2,6-di-t-butyl-4(4-methoxyphenyl) phenoxyl and antioxidant

LOO:

lipid peroxyl radical

PhO:

2,6-di-t-butyl-4(4-methoxyphenyl) phenoxyl

SCE:

saturated calomel reference electrode

S s :

slope of first-order plots of disappearance of 2,5-diphenyl-3,4-benzofuran in presence of antioxidant

S o :

slope of first-order plots of disappearance of 2,5-diphenyl-3,4-benzofuran in absence of antioxidant

Toc:

tocopherol and its analogues

Toc:

tocopheroxyl radical and its analogues

Toc-amine:

tocopheramine

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ehime University, 790, Matsuyama, Japan

    Shingo Itoh, Shin-ichi Nagaoka & Kazuo Mukai

  2. Developing Center Section No. 1, Konica Co. Ltd., Sakura 1, 191, Hino, Japan

    Satoru Ikesu & Yutaka Kaneko

Authors
  1. Shingo Itoh
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  2. Shin-ichi Nagaoka
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  3. Kazuo Mukai
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  4. Satoru Ikesu
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  5. Yutaka Kaneko
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Itoh, S., Nagaoka, Si., Mukai, K. et al. Kinetic study of quenching reactions of singlet oxygen and scavenging reactions of free radicals by α-, β-, λ- and σ-tocopheramines in ethanol solution and micellar dispersion. Lipids 29, 799–802 (1994). https://doi.org/10.1007/BF02536703

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  • DOI: https://doi.org/10.1007/BF02536703

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