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

Josip Mastelić ; Department of Organic Chemistry and Natural Products, Faculty of Chemical Technology, University of Split, N. Tesle 10, HR-21000 Split, Croatia
Igor Jerković ; Department of Organic Chemistry and Natural Products, Faculty of Chemical Technology, University of Split, N. Tesle 10, HR-21000 Split, Croatia
Marijana Vinković ; NMR Center, Ruđer Bošković Institute, P.O. Box 180, Bijenička 54, HR-10002 Zagreb, Croatia
Zoran Džolić ; Laboratory of Supramolecular and Nucleoside Chemistry, Ruđer Bošković Institute, P.O. Box 180, Bijenička 54, HR-10002 Zagreb, Croatia
Dražen Vikić-Topić ; NMR Center, Ruđer Bošković Institute, P.O. Box 180, Bijenička 54, HR-10002 Zagreb, Croatia

Sažetak

Naturally occurring glucosides of benzyl alcohol, (±)-menthol, (+)-borneol, thymol, carvacrol and eugenol were synthesized by the Koenigs-Knorr-Zemplén method (yields 19.5–52.2 %). Their β-D-glucopyranosidic structures were determined by one- and two-dimensional homoand heteronuclear 1H and 13C NMR spectroscopy. The β-configuration was additionally confirmed by the hydrolysis with β-glucosidase. Tetraacetyl-β-D-glucopyranosides, as intermediates, were GC-MS analyzed. Diastereomeric β-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.

Ključne riječi

glucosides of volatiles, synthesis of glucosides, 1D and 2D NMR spectra, glucoside tetraacetates, GC-MS spectra

Hrčak ID:

102950

URI

https://hrcak.srce.hr/102950

Posjeta: 1.953 *