Agricultural and Biological Chemistry
Online ISSN : 1881-1280
Print ISSN : 0002-1369
ISSN-L : 0002-1369
Synthesis and Tastes of Some Flavanone- and Dihydrochalcone Glycosides
Shintaro KAMIYASachiko ESAKIFukuko KONISHI
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1975 Volume 39 Issue 9 Pages 1757-1762

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Abstract
Naringenin-7-β-maltoside (I), -7-β-cellobioside (II), -7-β-lactoside (III), -7-β-melibioside (IV) and hesperetin-7-β-[D-galactosyl (α 1→2) D-glucoside] (V), -7-β-[D-glucosyl (β 1→2) D-galactoside] (VI) and -7-β-melibioside (VII) were prepared by the coupling of naringenin or hesperetin with the acetobromo derivatives of appropriate disaccharides followed by removal of the protecting acetyl groups.
Narigenindihydrochalcone-4'-β-kojibioside (VIII), -4'-β-maltoside (IX), -4'-β-cellobioside (X), -4'-β-lactoside (XI), -4'-β-melibioside (XII) and hesperetindihydrochalcone-4'-β-[D-galactosyl (α 1→2) D-glucoside] (XIII), -4'-β-sophoroside (XIV) and -4'-β-melibioside (XV) were synthesized by catalytic reduction of the appropriate flavanone-7-β-glycosides.
Among the compounds synthesized, IX and X are 4 and 8 times as sweet as sucrose on the basis of percentage concentration, respectively, but the others are tasteless.
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