Synthesis and equilibrium multistate of new pyrano-3-deoxyanthocyanin-type pigments in aqueous solutions

Joana L.C. Sousa, Vânia Gomes, Nuno Mateus, Fernando Pina, Victor de Freitas, Luís Cruz

Research output: Contribution to journalArticlepeer-review

10 Citations (Scopus)

Abstract

Pyrano-flavylium compounds are flavylium derivatives with occurrence in processed foodstuffs such as wine and red fruit juices. In this work, the chemical equilibria of “bio-inspired” pyrano-3-deoxyanthocyanin dyes (4–8), presenting different substituent groups in D ring (10-methyl, 10-catechol, 10-dimethylaminophenyl, 10-carboxy) as well as in B ring (3′,4′-dihydroxy, 4′-carboxy), were studied for the first time in aqueous solutions by UV–Vis spectroscopy. The presence of a methyl group at C-10 (pigment 4) seems to stabilize the flavylium cation (AH+) shifting the deprotonation of 7-OH to a higher pKa1 (pKa1 = 5.0 ± 0.1). On the other hand, the quinoidal bases (A, A) were more stabilized for the pigments which undergo the first acid-base equilibrium at C-10 substituent, as could be observed by the pKa2 constants (pKa2 = 8.4 ± 0.1 and pKa2 = 8.1 ± 0.1, pigments 6 and 8, respectively).

Original languageEnglish
Pages (from-to)6021-6030
Number of pages10
JournalTetrahedron
Volume73
Issue number41
DOIs
Publication statusPublished - 1 Jan 2017

Keywords

  • Chemical equilibria
  • Dyes
  • pK
  • Pyrano-3-deoxyanthocyanins
  • UV–Vis spectroscopy

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