A structural proof for the hypericin 1,6-dioxo tautomer

Authors
Dax, TG Falk, H Kapinus, EI
Citation
Tg. Dax et al., A structural proof for the hypericin 1,6-dioxo tautomer, MONATS CHEM, 130(7), 1999, pp. 827-831
Citations number
18
Categorie Soggetti
Chemistry
Journal title
MONATSHEFTE FUR CHEMIE
ISSN journal
00269247 → ACNP
Volume
130
Issue
7
Year of publication
1999
Pages
827 - 831
Database
ISI
SICI code
0026-9247(199907)130:7<827:ASPFTH>2.0.ZU;2-B
Abstract
Using 2D ROESY H-1 NMR spectroscopy it could be unequivocally shown from nu clear Overhauser effects and intramolecular exchange correlations of strate gic signals that hypericin as well as its 3-hypericinate ion are present as the tautomers with the carbonyl groups located in positions 7 and 14 in po lar solvents like dimethylsulfoxide. In apolar solvents like tetrahydrofura n hypericin prevails as the 1,6-dioxo tautomer.