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2D NMR analysis for unambiguous structural elucidation of phenolic compounds formed through reaction between (+)‐catechin and glyoxylic acid
Author(s) -
EsSafi NourEddine,
Le Guernevé Christine,
Cheynier Véronique,
Moutounet Michel
Publication year - 2002
Publication title -
magnetic resonance in chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0749-1581
DOI - 10.1002/mrc.1081
Subject(s) - chemistry , glyoxylic acid , heteronuclear single quantum coherence spectroscopy , heteronuclear molecule , carbon 13 nmr , proton nmr , two dimensional nuclear magnetic resonance spectroscopy , organic chemistry , stereochemistry , nuclear magnetic resonance spectroscopy
Various phenolic compounds were synthesized in an aqueous–alcoholic solution containing (+)‐catechin and glyoxylic acid which was used as a model of fruit‐derived food browning that usually occurs during aging. After purification by semi‐preparative HPLC, the isolated compounds were subjected to homo‐ and heteronuclear proton and carbon NMR analysis including COSY, TOCSY, ROESY, HSQC and HMBC techniques. These experiments allowed the structural elucidation and complete 1 H and 13 C NMR assignment of the isolated compounds. The strategies followed for the assignment of all proton and carbon resonances in addition to the linkage site determination are discussed. Copyright © 2002 John Wiley & Sons, Ltd.