Acesulfamate

Acesulfame K. Acesulfame K [55589-62-3] C H NO S -K, is an oxathia2iae derivative approximately 200 times as sweet as sucrose at a 3% concentration ia solutioa (70). It is approved for use as a nonnutritive sweeteaer ia 25 couatties (71), and ia the United States has approval for use in chewing gum, confectionery products, dry mixes for beverages, puddings, gelatins, and dairy product analogues, and as a tabletop sweetener (72). 

Sucrose occupies a unique position in the sweetener market (Table 3). The total market share of sucrose as a sweetener is 85%, compared to other sweeteners such as high fmctose com symp (HFCS) at 7%, alditols at 4%, and synthetic sweeteners (aspartame, acesulfame-K, saccharin, and cyclamate) at 4%. The world consumption of sugar has kept pace with the production. The rapid rise in the synthetic sweetener market during 1975—1995 appears to have reached a maximum. 

The sweetness of fmctose is enhanced by synergistic combiaations with sucrose (12) and high iatensity sweeteners (13), eg, aspartame, sacchatin, acesulfame K, and sucralose. Information on food appHcation is available (14,15). Fmctose also reduces the starch gelatinization temperature relative to sucrose ia baking appHcations (16—18). 

Acesulfame-K. Acesulfame-K [55589-62-3] (4), the potassium salt of acesulfame [33665-90-6] (6-methyl-l,2,3-oxathiaziQ-4(3ff)-one 2,2-dioxide), is a sweetener that resembles saccharin in stmcture and taste profile. 5,6-Dimethyl-l,2,3-oxathiazine-4(3ff)-one 2,2-dioxide, the first of many sweet compounds belonging to the dihydrooxathia2inone dioxide class, was discovered accidentally in 1967 (63). From these many sweet compounds, acesulfame was chosen for commercialisation. To improve water solubiUty, the potassium salt was made. Acesulfame-K (trade name Sunette) was approved for dry product use in the United States in 1988 and in Canada in October, 1994. Later, it was approved by the FDA for additional food categories such as yogurts, frosen and refrigerated desserts, and baked goods. 

Acesulfame-K is a white crystalline powder having a long (six years or more) shelf life. It readily dissolves in water (270 g/L at 20°C). Like saccharin, acesulfame-K is stable to heat over a wide range of pH. At higher concentrations, there is a detectable bitter and metallic off-taste similar to saccharin. Use of the sodium salt of feruHc acid [437-98-4] (FEMA no. 3812) to reduce the bitter aftertaste of acesulfame-K has been described (64). The sweetness potency of acesulfame-K (100 to 200x, depending on the matching sucrose concentration) (63) is considered to be about half that of saccharin, which is about the same as that of aspartame. 

Acesulfame-K—aspartame blends exhibit a significant synergistic effect (Fig. 4) (65,66). This synergy provides large cost savings for the diet foods industry. The blend also has a more rounded taste. Each sweetener apparendy masks the off-taste associated with the other. Increased blend usage is expected. 

Eig. 4. Isosweet blends where the soHd line represents acesulfame-K, the dotted line aspartame, and (— —) a 1 1 blend (65). 

Many synthetic processes have been described for acesulfame. One involves the condensation of a halosulfonyl isocyanate and an acetylene or a ketone (67,68). The duorosulfonyl isocyanate can be prepared by reaction of sulfuryl diisocyanate with duorosulfonic acid (69). 

Many analogues of saccharin have been synthesized since its discovery. With the exception of one compound, thieno[3,4-i/ isothiazolone dioxide [59337-79-0] lOOOX, this effort has not generated more potent compounds. Acesulfame-K could be considered a ring-modification derivative of saccharin, however. 

Cyclamate is about 30 times (8% sucrose solution sweetness equivalence) more potent than sugar. Its bitter aftertaste is minor compared to saccharin and acesulfame-K. The mixture of cyclamate and saccharin, especially in a 10 1 ratio, imparts both a more rounded taste and a 10—20% synergy. Cyclamate (6) is manufactured by sulfonation of cyclohexylamine (7). Many reagents can be used, including sulfamic acid, salts of sulfamic acid, and sulfur trioxide (74—77). 

To meet consumer demands, manufacturers are developing new nonnutritive sweeteners that more closely match the taste and mouthfeel of sucrose. There are several nonnutritive sweeteners currentiy pending FDA approval for use in soft drinks. They include sucralose [56038-13-2] aUtame [80863-62-3] encapsulated aspartame, cyclamates, and acesulfame-K [55589-62-3] also known as paUtinit. 

Fig. 1 Fluorescence scan of a chromatogram track with 3 gg each of acesulfame and saccharin and 2.25 ig of cyclamate per chromatogram zone. Cyclamate (1), saccharin (2), acesulfame (3).

Absolute configuration, 299 Absorbance, 501 Absorption spectrum, 420 Acesulfame-K, structure of, 1006 sweetness of, 1005 Acetal(s), 717... 

Acesulfame potassium Aspartame Fructose Invert sugar... 

Acesulfame potassium is a noncaloric sweetener that is two hundred times sweeter than sugar. It is used in tabletop sweeteners, toothpastes, soft drinks, desserts, baked goods, and canned foods. 

Acesulfame potassium is used with other sweeteners such as aspartame because it has a long shelf life, and tastes sweet right away. It also has a synergistic effect with other sweeteners, so less of each is necessary to achieve the same sweetness. 

Structurally related to saccharin are the oxathiazinone dioxides (104). Clauss and coworkers synthesized a series of these compounds, and demonstrated that they possess intense sweetness. Acesulfame-K, the potassium salt of 3,4-dihydro-6-methyl-l,2,3-oxathiazin-4-one 2,2-dioxide (104) has a sweetness intensity 130 times that of sucrose. 

Hagenauer Hener, U., Frank, C., Hener, U., Mosandl, A., Determination of aspartame, acesulfam-K, saccharin, caffeine, sorbic acid and benzoic acid in foods by HPLC. Bestimmung von Aspartam, Acesulfam-K, Saccharin, Coffein, Sorbinsaeure und Benzoesaeure in Lebensmitteln mittels HPLC Deutsche-Lebensmittel-Rundschau, 86(11),348-351,1990. 

Acesulfame potassium Aspartame Saccharin Saccharin sodium Sodium cyclamate... 

Acequinocyl, 14 349 Acesulfame-K, 12 41-42 24 233-234 Acesulfame-K-aspartame blends, 24 233 Acetalation, carbohydrate hydroxyl groups, 4 712... 

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