publication . Article . 2016

A comprehensive investigation of guaiacyl-pyranoanthocyanin synthesis by one-/two-dimensional NMR and UPLC–DAD–ESI–MSn

Anna Vallverdú-Queralt; Emmanuelle Meudec; Nayla Ferreira-Lima; Nicolas Sommerer; Olivier Dangles; Véronique Cheynier; Christine Le Guernevé;
Open Access English
  • Published: 01 Jan 2016
  • Publisher: HAL CCSD
  • Country: France
Abstract
Abstract In red and rose wines, the grape anthocyanins are progressively converted to more stable pigments, including phenylpyranoanthocyanins. One-/two-dimensional NMR and UPLC–DAD–ESI–MS n measurements were used to monitor the synthesis of guaiacylpyranomalvidin 3- O -glucoside from malvidin 3- O -glucoside and vinylguaiacol in model solutions and identify the products formed during the reaction. The highest conversion rates (30%, determined by 1 H qNMR) were obtained with a small excess of vinylguaiacol in methanol/water (70/30) at pH 3 and 35 °C. Two reaction pathways competed with the formation of guaiacylpyranomalvidin 3- O -glucoside. The first one only c...
Subjects
free text keywords: guaiacylpyranomalvidin 3-O-glucoside, optimization, UPLC-DAD-ESI-MSn, nmr, synthesis, wine, cyanin, vin, oenologie, anthocyane, [SDV.IDA]Life Sciences [q-bio]/Food engineering, Malvidin, chemistry.chemical_compound, chemistry, Organic chemistry, Pyranoanthocyanin, Glucoside, Nuclear magnetic resonance spectroscopy, High-performance liquid chromatography, Methanol, Chromatography, Proanthocyanidin, Pigment, visual_art.visual_art_medium, visual_art
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publication . Article . 2016

A comprehensive investigation of guaiacyl-pyranoanthocyanin synthesis by one-/two-dimensional NMR and UPLC–DAD–ESI–MSn

Anna Vallverdú-Queralt; Emmanuelle Meudec; Nayla Ferreira-Lima; Nicolas Sommerer; Olivier Dangles; Véronique Cheynier; Christine Le Guernevé;