Correlation of Chemical Structure and Taste in the Saccharin Series

Hamor, Glenn H.

doi:10.1126/science.134.3488.1416

Cited by 30 publications

(7 citation statements)

References 3 publications

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“…This would account for the reduced responsiveness of 6-chlorosaccharin. The barrier is probably stereochemical in view of the fact that g-substituted saccharin molecules are not as sweet as the unsubstituted molecule (Hamor, 1961). One puzzle is the failure of Osulfobenzoic acid to stimulate despite being anionic and having the sulfuryl oxygen molecules.…”

Section: Discussionmentioning

confidence: 99%

Stimulation of the gerbil's gustatory receptors by saccharin

Jakinovich¹

1982

J. Neurosci.

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The gustatory responses from the chorda tympani nerve of the Mongolian gerbil, Meriones unguiculatus, were tested with saccharin and some closely related compounds. Only two compounds, saccharin and 6-chlorosaccharin, stimulated the gerbil's taste receptors to any degree and in the same order in which they are sweet to man, saccharin > 6-chlorosaccharin.Those compounds which are tasteless to man did not stimulate and included N-methyl saccharin, phthalimide, and Osulfobenzoic acid. These nonstimulating derivatives did not inhibit the saccharin electrophysiological response. The saccharin taste response pH optimum is from 5 to 8. At pH 7 and 8, saccharin is fully ionized and is binding to the receptor site by an anionic mechanism. Kinetic plots of the taste response at pH 7 indicate that saccharin is forming 1:l complexes with it. In addition, mixtures of saccharin and sucrose stimulate in such a manner as to suggest that they are interacting at different receptor sites.In a previous study (Jakinovich, 1981), data were accumulated on the gerbil's taste response to a group of artificial sweeteners, including saccharin. We tested them both behaviorally and electrophysiologically, anticipating uniform responses because sweetness in humans is unified under Shallenberger and Acree's (1967) "AH,B" theory. This proved not to be the case. Of the 21 sweeteners tested electrophysiologically, only 14 stimulated the gerbil's taste nerve, and of those 14, 6 did not taste like sucrose according to behavioral experiments.The purpose of the present investigation was to focus on the gerbil's taste response to saccharin. This sweetener is important not only because it stimulates the gerbil's taste nerve and resembles the taste of sucrose behaviorally (Jakinovich, 1981) but because, in mammals, it is the most uniformly preferred artificial sweetener (Jakinovich, 1980), indicating a common sweet taste receptor mechanism. With regard to this mechanism, there is the intriguing possibility that saccharin and sugars are stimulating the taste receptors through separate receptor sites (Zawalich, 1973 saccharin were interacting at the same or at different receptor sites. Finally, a pH experiment was conducted because saccharin's amide group (the "AH" group of Shallenberger and Acree (1967) ) will ionize depending upon the pH and the results could shed some light on the binding mechanism.The results of these experiments suggest that the gerbil's taste specificity to saccharin is the same as man's inasmuch as the taste responses were similar. The saccharin derivatives which taste sweet to man also stimulated the gerbil's taste receptors, and the tasteless ones did not stimulate. However, it would seem that the taste stimulation mechanism is not consistent with the "AH,B" theory. We have found that the saccharin taste response has a pH optimum range from 5 to 8. At pH 7 and 8, saccharin is fully ionized, lacks the AH group, and therefore, cannot be forming hydrogen bonds with the receptor site. Moreover, contrary to the theory, mixtur...

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Section: Discussionmentioning

confidence: 99%

Stimulation of the gerbil's gustatory receptors by saccharin

Jakinovich¹

1982

J. Neurosci.

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“…Many of these structural analogues of saccharin have been found to be bitter and give an aftertaste (Moncrieff, 1944). A recent publication (Hamor, 1961) reports a large number of substitutional derivatives of saccharin, many of which have been found to be bitter.…”

Section: Discussionmentioning

confidence: 99%

A Study of the True Taste of Saccharin

Rader

Tihanyi

Zienty

1967

Journal of Food Science

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SUMMARY— When samples of saccharin were highly purified, bitterness and aftertaste were not significantly diminished. Numerous purification methods failed to remove these undesirable flavor notes. The presence of sequestering agents also failed to diminish bitterness and aftertaste. While the undesirable flavor notes of saccharin cannot be proven to be intrinsic, the hypothesis that they are due to impurities is most untenable. Conclusive evidence shows that the bitterness and aftertaste are at least in part a true property of saccharin.

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“…Prepared by Holleman as saccharine analogue, sweetener properties of the o-benzenedisulfonimide were tested: it "has at once a sweet and acid taste with a bitter after taste" [2]; however, the replacement of the imide hydrogen by an alkyl group led to practically tasteless compounds [83].…”

Section: Uses and Applicationsmentioning

confidence: 99%

o-Benzenedisulfonimide: An Organic Reagent and Organocatalyst of Renewed Interest

Barbero¹,

Bazzi

Cadamuro

et al. 2011

COC

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ABSTRACT:Synthesized nearly one century ago as a saccharine-like sweetener compound, the obenzenedisulfonimide has received a discontinuous attention in the past. In the last century, various synthetic procedures have been reported, in confirmation of the interest in this intriguing compound. In recent years, it has been used as a leaving group in reactions of nucleophilic substitution of amines with alcohols or phenols to give the corresponding ethers. Its Nfluoroderivative is a stable and efficient fluorinating agent, which has found applications in several asymmetric syntheses. In previous studies, its conjugated base has been extensively used as stabilizing counter-ion of arenediazonium salts; safely isolated and stored in a dry state, ready to use, they have been applied successfully in many dediazoniation reactions, with interesting mechanistic insights. More recently, due to its high acidity, the o-benzenedisulfonimide has been used in catalytic amounts in some common acid-catalyzed organic reactions. Valuable aspects of this catalyst are its easy recovery from the reaction mixture and its reuse in other reactions, with clear economic and ecological advantages. Finally, the disulfonimide functional group has been proposed as a powerful chiral motif for strong Brønsted acids in asymmetric organocatalysis.

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Correlation of Chemical Structure and Taste in the Saccharin Series

Cited by 30 publications

References 3 publications

Stimulation of the gerbil's gustatory receptors by saccharin

Stimulation of the gerbil's gustatory receptors by saccharin

A Study of the True Taste of Saccharin

o-Benzenedisulfonimide: An Organic Reagent and Organocatalyst of Renewed Interest

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