Publicação
Thermodynamics and Kinetics of 3-Deoxyanthocyanidins Versus Anthocyanins
| Resumo: | 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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| Autores principais: | Yang, Peiqing |
| Outros Autores: | Basílio, Nuno; Liao, Xiaojun; Pina, Fernando |
| Assunto: | 3-deoxyanthocyanidins Anthocyanins Kinetics and thermodynamics Photochemistry General Chemistry General Agricultural and Biological Sciences |
| Ano: | 2025 |
| País: | Portugal |
| Tipo de documento: | artigo |
| Tipo de acesso: | acesso aberto |
| Instituição associada: | Universidade Nova de Lisboa |
| Idioma: | inglês |
| Origem: | Repositório Institucional da UNL |
| Resumo: | 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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