Thermodynamics and Kinetics of 3-Deoxyanthocyanidins Versus Anthocyanins

Yang, Peiqing; Basílio, Nuno; Liao, Xiaojun; Pina, Fernando

http://hdl.handle.net/10362/184957

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Anthocyanins, anthocyanidins, 3-deoxyanthocyanins, and 3-deoxyanthocyanidins share five common chemical species in acidic media: flavylium cation, quinoidal base, hemiketal, and cis and trans chalcones. These species are reversibly interconnected by four chemical reactions: proton transfer, hydration, tautomerization, and isomerization. The absence of a hydroxyl group or glycoside at position 3 of the flavylium cation in 3-deoxy species substantially alters their thermodynamic and kinetic properties compared to those of anthocyanins. This study compared these properties between anthocyanins and 3-deoxy species and investigated the chemistry and photochemistry of luteolinidin using an updated mathematical model. The extension of the study to basic media (holistic approach) revealed slower OH- nucleophilic addition in luteolinidin, consequently prolonging its color retention in comparison to anthocyanins. Furthermore, luteolinidin exhibit significantly slower degradation rates. While anthocyanins generally lack significant photochemistry, 3-deoxy species display efficient photochromism, presenting promising possibilities for diverse applications.

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Funding Information: This work received financial support from FCT/MCTES (UIDP/50006/2020 DOI 10.54499/UIDP/50006/2020) through national funds, the National Natural Science Foundation of China (NSFC) (grant number: 31930087), and the China Scholarship Council (grant number: 202306350167). Publisher Copyright: © 2025 American Chemical Society.