246181-58-8Relevant academic research and scientific papers
Structure of a new xanthylium salt derivative
Es-Safi, Nour-Eddine,Guerneve, Christine Le,Labarbe, Benoit,Fulcrand, Helene,Cheynier, Veronique,Moutounet, Michel
, p. 5869 - 5872 (1999)
A new polyphenolic compound with a xanthylium skeleton has been synthesised from (+)catechin and glyoxylic acid. Its structural elucidation was achieved by UV, MS and NMR spectroscopies. Its formation involved glyoxylic acid-mediated dimerisation of (+)-c
New polyphenolic compounds with xanthylium skeletons formed through reaction between (+)-catechin and glyoxylic acid
Es-Safi, Nour-Eddine,Le Guerneve, Christine,Fulcrand, Helene,Cheynier, Veronique,Moutounet, Michel
, p. 5211 - 5217 (1999)
The reaction between (+)-catechin and glyoxylic acid was studied in a model solution system. The major (+)-catechin carboxymethine-linked dimer was isolated and shown to proceed to new polyphenolic compounds exhibiting absorption maxima around 440 and 460 nm. Three yellow pigments were obtained by incubation of the 8-8 colorless isomer. One was the previously reported xanthylium compound NJ2 with a maximum at 440 nm. The other two, showing absorption maxima at 460 nm, were obtained separately by incubation of the colorless dimer in hydroethanolic or methanolic medium. Structural elucidation of these two new yellow pigments was achieved by means of MS and 1D and 2D NMR techniques and showed that they were, respectively, ethyl and methyl esters of NJ2. The fact that these compounds were not obtained when NJ2 was incubated in hydromethanolic or ethanolic medium showed that esterification took place before the formation of the xanthylium chromophores. The detection of the esterified colorless compounds and the corresponding xanthene intermediates confirmed the postulated mechanism. New pigments exhibiting a strong absorption at 560 nm were also observed.
An oxidized tartaric acid residue as a new bridge potentially competing with acetaldehyde in flavan-3-ol condensation
Fulcrand, Helene,Cheynier, Veronique,Oszmianski, Jan,Moutounet, Michel
, p. 223 - 227 (1997)
Iron-induced oxidation of (+)-catechin in a wine-like solution yielded typical products, including colourless and yellow compounds. Structural characterization of the major colourless one indicated that it is a dimer, in which flavanol units are linked th
Production and Isomeric Distribution of Xanthylium Cation Pigments and Their Precursors in Wine-like Conditions: Impact of Cu(II), Fe(II), Fe(III), Mn(II), Zn(II), and Al(III)
Guo, Anque,Kontoudakis, Nikolaos,Scollary, Geoffrey R.,Clark, Andrew C.
, p. 2414 - 2425 (2017/03/30)
This study establishes the influence of Cu(II), Fe(II), Fe(III), Zn(II), Al(III), and Mn(II) on the oxidative production of xanthylium cations from (+)-catechin and either tartaric acid or glyoxylic acid in model wine systems. The reaction was studied at 25 °C using UHPLC and LC-HRMS for the analysis of phenolic products and their isomeric distribution. In addition to the expected products, a colorless product, tentatively assigned as a lactone, was detected for the first time. The results show the importance of Fe ions and a synergistic influence of Mn(II) in degrading tartaric acid to glyoxylic acid, whereas the other metal ions had minimal activity in this mechanistic step. Fe(II) and Fe(III) were shown to mediate the (+)-catechin-glyoxylic acid addition reaction, a role previously attributed to only Cu(II). Importantly, the study demonstrates that C-8 addition products of (+)-catechin are promoted by Cu(II), whereas C-6 addition products are promoted by Fe ions.
Role of aldehydic derivatives in the condensation of phenolic compounds with emphasis on the sensorial properties of fruit-derived foods
Es-Safi, Nour-Eddine,Cheynier, Veronique,Moutounet, Michel
, p. 5571 - 5585 (2007/10/03)
The reactions between (epi)catechin, mavidin 3-O-glucoside, and some aldehydes were investigated by LC/DAD and LC/ESI-MS analysis. The obtained results showed that the acetaldehyde-mediated condensation occurred more generally and glyoxylic acid, furfural
