Synthesis and sensory evaluation of ring-substituted dihydrochalcone sweeteners. 2. Analogs of 3'-carboxyhesperetin dihydrochalcone, a high-potency dihydrochalcone sweetener

Analogues of 3'-carboxyhesperetin dihydrochalcone were evaluated for taste potency and sweetness quality at both the tip of the tongue and the back of the mouth. High levels of sweetness were seen at the tip of the tongue, while at the back of the mouth higher taste potencies comprised mainly l...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1991-04, Vol.39 (4), p.663-667
Main Authors: Whitelaw, Murray L, Chung, Hai Jung, Daniel, James R
Format: Article
Language:English
Subjects:
ANALISIS ORGANOLEPTICO
ANALYSE ORGANOLEPTIQUE
AROMA
CALCONA
CHALCONE
EDULCORANT
EDULCORANTES
FLAVEUR
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Summary:Analogues of 3'-carboxyhesperetin dihydrochalcone were evaluated for taste potency and sweetness quality at both the tip of the tongue and the back of the mouth. High levels of sweetness were seen at the tip of the tongue, while at the back of the mouth higher taste potencies comprised mainly licorice-flavored side-tastes. Alterations to the B-ring isovanillyl portion of 3'-carboxyhesperetin dihydrochalcone reduced both taste potency and sweetness quality, implying that B-ring functionality is crucial for sweet receptor interaction. It is proposed that the 3'-carboxylic acid group enhances sweetness of the dihydrochalcone structure by allowing two conformations to fit into and bind the sweetener receptor, according to the tripartite AH/B/X sweet pharmacophore theory
ISSN:0021-8561
1520-5118
DOI:10.1021/jf00004a007