Synthesis and Taste of Some Isomers of Naringin

Syntheses of Severalβ-l-Rhamnopyranosides

“…Since the key compound 30 could be easily prepared from L-quinovose f3-tetraacetate 15 ) and was very stable and easy to handle, the syntheses of a number of disaccharides containing a f3-L-rhamnopyranosyllinkage by the use of 30 are in progress in our laboratory. (8).…”

Sweet organic chemistry

“…For example, the sweet taste is abolished if the rhamnose unit is joined to the C-6 hydroxyl of glucose (6-0-rhamnosylglucoside) instead of the C-2 hydroxyl, although a methyl group at the glucose C-6 hydroxyl has no noticeable effect on sweetness. In general, L-sugars with a 1C ring conformation may replace the L-rhamnose unit without loss of the sweet taste but the substitution of D-sugars destroys sweetness (32). Sweetness may be retained even upon removal of one or both sugar units.…”

Structure–Taste Relationships of Flavanone and Dihydrochalcone Glycosides Containing (l→2) Linked Disaccharides

“…When the rx-Lrhamnose unit in XXVIII is replaced by rx-or f3-L-fucose, the C-2,4-epimer of L-rhamnose, the taste of the resulting glycoside (III, V) retains considerable bitterness comparable with that of naringin. Ina previous paper, 21) we reported that when L-rhamnose unit in the naringin is replaced by rx-L-quinovose, the C-2-epimer of L-rhamnose, the bitter taste was doubled, while if by f3-L-quin,ovose, the taste disappeared due to the great decrease in watersolubility of the resulting glycoside. We concluded that the 13-1 t'-/2 linkage completely deprives the compound of its ability to elicit a bitter taste and further presumed that replacement of the rx-L-rhamnosyl group of the naringin by the f3-L-rhamnose unit will reach the same conclusion, although an experiment has not yet been carried out.…”