Design, synthesis and evaluation of dihydrochalcone sweeteners
Abstract
A series of novel dihydrochalcone sweeteners were rationally designed to enable investigation into the sweetness inducing mechanism. Seventeen dihydrochalcone structures were synthesised and purified in the laboratory. These new compounds were evaluated for both sweetness and total taste intensity by a trained taste panel. Taste evaluations were analyzed in terms of the physicochemical parameters of substituent modifications. Taste intensity was found to be controlled primarily by electronic factors, but also by hydrophobic factors, at the dihydrochalcone B-ring. The most intensely sweet dihydrochalcone currently known, 3$\sp\prime$-carboxyhesperitin dihydrochalcone, was discovered. This compound was evaluated as being almost 3,500 times sweeter than a 6% w/v sucrose solution. Attempts to decrease the side-tastes and aftertaste characteristic of dihydrochalcones were unsuccessful. These competing tastes were concluded to result from interaction with non-sweet taste receptors towards the back of the mouth, and seem to be inherent to the sweetness eliciting glucophores of the dihydrochalcone structure.
Degree
Ph.D.
Advisors
Daniel, Purdue University.
Subject Area
Food science
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