81410-23-3Relevant articles and documents
IODINATION AND DEUTERATION OF CATECHIN DERIVATIVES
Kiehlmann, E.,Lehto, N.,Cherniwchan, D.
, p. 2431 - 2439 (2007/10/02)
The preparation and 1H and 13C nuclear magnetic reonance spectra of ten monoiodocatechin derivatives are described.The iodination of catechin with N-iodosuccinimide (NIS) takes place regiospecifically at C-6 in acetone but preferentially at C-8 in dimethylformamide; both products can be derivatized at oxygen in alkali medium but lose iodine in the presence of acid. 3',4',5,7,-Tetra-O-methylcatechin reacts with NIS regiospecifically at C-8 while catechin pentaacetate resists iodination.The debromination of 6-bromo- and 6,8-dibromocatechin with sodium sulfite in CD3CN/D2O is accompained by H/D-exchange at C-6 and C-8.The synthesis of catechin pentaacetate from partially deuterated catechin and its conversion to terta-O-methylcatechin proceed without H/D-exchange and permit distinction between the H-6 and H-8 chemical shifts.
Tannins and Related Compounds. Part 13. Isolation and Structures of Trimeric, Tetrameric, and Pentameric Proanthicyanidins from Cinnamon
Nonaka, Gen-ichiro,Morimoto, Satoshi,Nishioka, Itsuo
, p. 2139 - 2145 (2007/10/02)
A proanthocyanidin trimer, two tetramers, and a pentamer have been isolated in their free phenolic forms from cinnamon, the bark of Cinnamomum zeylanicum (Lauraceae).Partial acid-catalysed degradation of these tannins with phenylmethanethiol, in conjunction with 1H- and 13C-n.m.r. analysis, has unequivocally established their structures as epicatechin-(4β->8, 2β->7)epicatechin-(4α->8)-epicatechin (5); epicatechin-(4β->8)epicatechin-(4β->8, 2β->7)-epicatechin-(4α->8)-epicatechin (6); epicatechin-(4β->6)-epicatechin-(4β->8, 2β->7)-epicatechin-(4α->8)-epicatechin (7); and epicatechin-(4β->8)-epicatechin-(4β->8)epicatechin-(4β->8, 2β->7)-epicatechin-(4α->8)-epicatechin (8).