Synthesis of Selected Naturally Occurring Glucosides of Volatile Compounds. Their Chromatographic and Spectroscopic Properties

Abstract

Naturally occurring glucosides of benzyl alcohol, (+/-)-menthol, (+)-borneol, thymol, carvacrol and eugenol were synthesized by the Koenigs-Knorr-Zemplen method (yields 19.5-52.2%). Their beta-D-glucopyranosidic structures were determined by one- and two-dimensional homo- and heteronuclear H-1 and C-13 NMR spectroscopy. The beta-configuration was additionally confirmed by the hydrolysis with P-glucosidase. Tetraacetyl-beta-D-glucopyranosides, as intermediates, were GC-MS analyzed. Diastereomeric beta-glucoside tetraacetates of (+/-)-menthol were well separated on the HP-101 column. The mass spectra of glucopyranoside tetraacetates were mutually compared, as well as with the spectra of their aglycones.