83554-46-5Relevant articles and documents
145. Synthesis of 3-Methoxy- and 3-(β-D-Glucopyranosyloxy)flavylium Ions. Influence of the Flavylium Substitution Pattern on the Reactivity of Anthocyanins in Aqueous Solution
Dangles, Olivier,Elhajji, Hakima
, p. 1595 - 1610 (1994)
The synthesis of 3-glycosyloxylated flavylium ions (anthocyanins), in particular of callistephin (4), a natural anthocyanin, is described.The structural transformations in aqueous solution and molecular complexation with chlorogenic acid (7) and caffeine (8) of the synthesized pigments 3 and 4 are investigated and compared to those of the corresponding 3-methoxyflavylium ions 1 and 2 and to those of oenin (5) and malvin (6), two very common natural anthocyanins.The results are discussed in terms of the role played by the glycosyloxy residues in the chemical properties of anthocyanins.Anthocyanin molecular complexation (copigmentation) is quantitatively investigated by UV/VIS spectroscopy and 1H-NMR.In particular, the UV/VIS spectroscopic data are interpreted using a general theoretical treatment, which, e.g., allows to demonstrate the formation of molecular complexes between the colourless forms of an anthocyanin and 8.
ELUCIDATION OF THE MULTIPLE EQUILIBRIA OF MALVIN IN AQUEOUS SOLUTION BY ONE- AND TWO-DIMENSIONAL NMR
Santos, Helena,Turner, David L.,Lima, Joao C.,Figueiredo, Paulo,Pina, Fernando S.,Macanita, Antonio L.
, p. 1227 - 1232 (2007/10/02)
One- and two-dimensional NMR were used to characterize the several forms of malvin present in aqueous solution in the pH range 0.3-4.5 and to determine their molar fractions as a function of pH.In addition to the flavylium cation, two hemiacetal forms and both the cis and trans form of chalcone were firmly identified.The pathways for the interconversion of different forms were derived and and the molar absorbances of the species calculated by coupling NMR and UV/Vis data.Equilibrium constants were determined at different temperatures, and enthalpy and entropy changes were calculated for the interconversion processes.The conclusions are supported by molecular orbital calculations. Key words: Anthocyanins; malvin; multi-equilibria; two-dimensional NMR.