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Synthesis of selected naturally occurring glucosides of volatile compounds. Their chromatographic and spectroscopic properties

Mastelić, Josip; Jerković, Igor; Vinković, Marijana; Džolić, Zoran; Vikić-Topić, Dražen (2004) Synthesis of selected naturally occurring glucosides of volatile compounds. Their chromatographic and spectroscopic properties. Croatica Chemica Acta, 77 (3). pp. 491-500. ISSN 0011-1643

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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.

Item Type: Article
Uncontrolled Keywords: glucosides of volatiles; synthesis of glucosides; 1D and 2D NMR spectra; glucoside tetraacetates; GC-MS spectra; d-glucopyranosides; glycosides
Subjects: NATURAL SCIENCES > Chemistry
Divisions: Division of Organic Chemistry and Biochemistry
NMR Center
Projects:
Project titleProject leaderProject codeProject type
Eterična ulja - glikozidi isparljivih spojeva - sinteza glikozidaJosip Mastelić0011010MZOS
Nuklearna magnetska rezonancija i proračuni bioorganskih molekulaDražen Vikić-Topić0098059MZOS
Depositing User: Dražen Vikić-Topić
Date Deposited: 12 Nov 2013 12:53
Last Modified: 27 Feb 2014 11:24
URI: http://fulir.irb.hr/id/eprint/926

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