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Contribution à l'étude du comportement de la catéchine en milieu alcalin
Author(s) -
Courbat Pierre,
Weith André,
Albert Alban,
Pelter Andrew
Publication year - 1977
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19770600522
Subject(s) - chemistry , enol , stereochemistry , catechin , bicyclic molecule , catalysis , organic chemistry , polyphenol , antioxidant
Contribution to the study of the behaviour of catechin in alkaline medium When catechin ( 1 ) is warmed with aqueous alkali it first undergoes rapid epimerisation. After some time a novel bridged carbocyclic enol, catechinic acid ( 3 ) separates out and may be isolated in excellent yield. Eventually catechinic acid isomerises to 2‐(3′,4′‐dihydroxyphenyl)‐3,9‐epoxy‐6‐oxo‐bicyclo[3,3,1]‐non‐7‐en‐8,9‐diol ( 4 ) via an open chain anion ( 5 ) which is also involved in the epimerisation of catechin. Assignments of structure are given and the equilibria observed are discussed.