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Synthesis and antioxidant properties of (dodecylsulfanyl)methyl quercetin derivatives

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Abstract

Mono-, bis-, and tris[(dodecylsulfanyl)methyl]-substituted quercetin derivatives were obtained by the reaction of quercetin with (N,N-diethylaminomethyl) dodecyl sulfide. These compounds under the conditions of AIBN-initiated oxidation of styrene (37 °C) terminated oxidation chains with a stoichiometric inhibition coefficients of 2.0±0.1 and rate constants of 5.1 · 105, 4.8 · 105, and 2.9 · 105 L mol-1 s-1, respectively. Based on the rate constants, the O-H bond energy values in the molecules of quercetin and its mono-, bis-, and tris- [(dodecylsulfanyl) methyl]-substituted derivatives were calculated and found to be equal to 334.4, 341.4, 341.7, and 344.7 kJ mol-1, respectively. It was established that the ability of the synthesized thio derivatives of quercetin to inhibit thermal autooxidation of lard (133 °C) is 1.3-2.7 times higher than that of the reference antioxidants (a-tocopherol, BHT, and BHA). According to the in silico assessment of acute toxicity for rats, the synthesized derivatives are low-toxic and non-toxic compounds.

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Authors and Affiliations

  1. Novosibirsk State Pedagogical University, 28 ul. Vilyuiskaya, 630126, Novosibirsk, Russian Federation

    T. K. Bagavieva, S. E. Yagunov, S. V. Kholshin, I. A. Emelyanova, O. I. Prosenko & A. E. Prosenko

  2. Novosibirsk Institute of Antioxidants, 54a Krasnyiprosp., 630091, Novosibirsk, Russian Federation

    O. I. Prosenko & A. E. Prosenko

Authors
  1. T. K. Bagavieva
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  2. S. E. Yagunov
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  3. S. V. Kholshin
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  4. I. A. Emelyanova
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  5. O. I. Prosenko
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  6. A. E. Prosenko
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Correspondence to S. E. Yagunov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2283–2289, December, 2019.

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Bagavieva, T.K., Yagunov, S.E., Kholshin, S.V. et al. Synthesis and antioxidant properties of (dodecylsulfanyl)methyl quercetin derivatives. Russ Chem Bull 68, 2283–2289 (2019). https://doi.org/10.1007/s11172-019-2701-2

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  • DOI: https://doi.org/10.1007/s11172-019-2701-2

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