Title: Alternative Sweeteners

2
Acesulfame K
Gert-Wolfhard von Rymon Lipinski
Nutrinova Nutrition Specialties and Food Ingredients GmbH,
Frankfurt/Main, Germany
Lisa Y. Hanger
Nutrinova, Inc., Somerset, New Jersey
I. INTRODUCTION
Clauss and Jensen (1) in 1967 incidentally discovered a sweet-tasting compound,
5,6-dimethyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide, having a new ring system
that had not been previously synthesized. Systematic research on dihydrooxathiazinone
dioxides revealed quite a number of sweet-tasting compounds in this
group of substances. Variations of substituents in positions 5 and 6 of the ring
system showed noticeable influence on the intensity and purity of the sweetness.
All synthesized dihydrooxathiazinone dioxides, however, exhibited some sweetness,
even the ring system without substituents. The maximum sweetness was
found in compounds with short-chain alkyl groups.
Sensory evaluations of the different dihydrooxathiazinone dioxides showed
that the substitutions on the ring system not only influenced the intensity but also
the purity of the sweetness (Fig. 1).
In addition to variations of substituents on the dihydrooxathiazinone dioxide
ring system, structurally similar compounds were synthesized to investigate
whether variations within the ring system would influence the sweet taste. These
evaluations did not reveal any new sweet-tasting compounds; even methylation
on the nitrogen in the ring furnishes a compound without sweetness (Fig. 2). An
evaluation of the different compounds clearly demonstrated that 6-methyl-1,2,3oxathiazine-4(3H)-one
2,2-dioxide exhibited the most favorable taste properties.
Because production of this compound seemed to be less difficult than that of
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