Original scientific paper

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

Abstract

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.

Keywords

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

Publication date:

25.10.2004.

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