As a continuation of our studies on the relationship between structure and sweet taste of isovanilline-type sweeteners, (3-hydroxy-4-methoxy)benzyl-benzoate (17) and -salicylate (17c), analogues of dihydrochalcone-type sweetener analogues of (+)-phyllodulcin [(+)-5] and CH-401 (14c) have been synthesized. Surprisingly, 17c has been found to be tastless, while 17e was slightly sweet. These observations could be explained by the current hypothesis on the receptor model for isovanilline-type sweet derivatives.
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