K-Acesulfame

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). 

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. 

Acesulfam-K Acesulfame K Acesulfame potassium Acesulfame potassium salt CCRIS 1032 EINECS 259-715-3 H733293 Hoe 095 6-Methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide, potassium salt 1,2,3-Oxathiazin-4(3H)-one, 6-methyl-, 2,2-dioxide, potassium salt Potassium 5-methyl-1,2,3-oxathiazin4(3H)-one 2,2-dioxide Potassium acesulfame. Sweetener used In foods and cosmetics. White solid dec 225° d = 1.81 Xm a 225 nm (e 10762) soluble in H2O (360 g/l), organic solvents LDso (rat ori) = 7431 mg/kg HoechstAG. 

Potassium sodium tartrate C4H4KNaOe 4H2O Potassium sodium tartrate tetrahydrate C4H4K2O5 Potassium malate C4H4NO4S K Acesulfame potassium C4H4N2 Pyrazine Succinonitrile C4H4N2O2 Maleic hydrazide Uracil C4H4N4... 

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 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 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. 

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

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. 

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

Determination of acesulfame-K in table top preparations -Spectrometric method... 

Sweeteners can be roughly divided into two groups bulk and intense sweeteners. Prodolliet (1996) and Gloria (2000) reviewed thoroughly the analysis and properties of intense sweeteners acesulfame-K, alitame, cyclamate, aspartame, glycyrrhizin, neohesperidin DC, saccharin, stevioside, sucralose and thaumatin. They are generally used in low calorie products such as diet... 

There is a recent trend towards simultaneous CE separations of several classes of food additives. This has so far been applied to soft drinks and preserved fruits, but could also be used for other food products. An MEKC method was published (Lin et al., 2000) for simultaneous separation of intense sweeteners (dulcin, aspartame, saccharin and acesulfame K) and some preservatives (sorbic and benzoic acids, sodium dehydroacetate, methyl-, ethyl-, propyl- and isopropyl- p-hydroxybenzoates) in preserved fruits. Ion pair extraction and SPE cleanup were used prior to CE analysis. The average recovery of these various additives was 90% with good within-laboratory reproducibility of results. Another procedure was described by Frazier et al. (2000b) for separation of intense sweeteners, preservatives and colours as well as caffeine and caramel in soft drinks. Using the MEKC mode, separation was obtained in 15 min. The aqueous phase was 20 mM carbonate buffer at pH 9.5 and the micellar phase was 62 mM sodium dodecyl sulphate. A diode array detector was used for quantification in the range 190-600 nm, and limits of quantification of 0.01 mg/1 per analyte were reported. The authors observed that their procedure requires further validation for quantitative analysis. 

The extent of safety studies necessary to obtain food additive approval can be demonstrated by the studies carried out on acesulfame K (trade name Sunett ), one of the sweeteners developed in course of the last 25 years,7 which has been endorsed for food use by the Joint Expert Committee on Food Additives (JECFA) of the WHO and FAO and the Scientific Committee for Foods (SCF) of the EU and has meanwhile been approved in more than 100 countries. This program shows the wide range of studies necessary. 

---