By Pericles Markakis
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Extra info for Anthocyanins as Food Colors
B. Covalent Hydration of the Pyrylium Nucleus This is a reversible pH-dependent reaction [Eq. (2)] for which the equilibrium constant K" = ([B]/[AH+])aH+ was first measured by Sondheimer (1953) in the case of pelargonidin 3-monoglucoside. Covalent addition of water takes place at C-2. The mechanism associated with this reaction is probably a concerted process where the proton transfer and the C-O bond breaking (or making) occur at the same time, as in Eq. (17) 20 Raymond Brouillard (Brouillard and Dubois, 1977).
For natural anthocyanins, this reaction is responsible for the loss of color when the solution is slightly acidic. Since the conjugation between the A-ring and the B-ring is suppressed in the carbinol, visible light is not absorbed. As a general rule, nucleophilic addition to anthocyanins leads to fading. =ltIT-d HH Transition state ' (17) 8 H. H - \ + ti~ (18) B Work in this laboratory (Brouillard and Delaporte, 1977) has shown that the rate of equilibration of hydration is about 106 times lower than that of the acid-base reactions giving rise to the prototropic tautomers.
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Anthocyanins as Food Colors by Pericles Markakis