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- W1990506557 abstract "Very recently, application of taste dilution analysis to heated xylose/alanine solutions led to the isolation of two bitter-tasting compounds exhibiting extraordinarily low detection thresholds of 0.00025 and 0.001 mmol/kg of water, respectively. On the basis of LC-MS and NMR spectroscopy, the structures of these compounds, named quinizolate and homoquinizolate, were proposed as 1-oxo-1H,4H-quinolizinium-7-olates. Since recent experiments in our laboratory shed some doubt on the entire correctness of their structures, labeling experiments with mixtures of multiply (13)C-labeled and nonlabeled pentoses were performed to follow the joint transfer of several (13)C atoms en bloc into the bitter compounds by LC-MS and NMR isotopomer diagnosis. The site-specific visualization of the mosaics assembled from (13)C-labeled and (12)C-labeled carbon modules in both bitter compounds demonstrated the structures of quinizolate and homoquinizolate to be the previously unknown (2E)-7-(2-furylmethyl)-2-(2-furylmethylidene)-3-(hydroxymethyl)- and (2E)-7-(2-furylmethyl)-2-(2-furylmethylidene)-3,8-bis(hydroxymethyl)-1-oxo-2,3-dihydro-1H-indolizinium-6-olate." @default.
- W1990506557 created "2016-06-24" @default.
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- W1990506557 date "2002-09-07" @default.
- W1990506557 modified "2023-09-26" @default.
- W1990506557 title "Reinvestigation of the Chemical Structure of Bitter-Tasting Quinizolate and Homoquinizolate and Studies on Their Maillard-Type Formation Pathways Using Suitable <sup>13</sup>C-Labeling Experiments" @default.
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- W1990506557 doi "https://doi.org/10.1021/jf020473k" @default.
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