6- Methyl-l,2,3-oxathiazine-4 -one

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. 

The potassium salt of 6-methyl-l,2.3-oxathiazin-4-one 2,2-dioxide known as acesulfame-K is used as an artificial sweetener (trade name Sunett). Here the negative charge is delocalized over both the carbonyl and the sulfone groups. 

This intense sweetener (8) is quoted as having the same effective sweetness as aspartame, but unlike aspartame it is sufficiently heat stable that it can be added at the beginning of the boil in high-boiled products. If a product with the same amount of acesulfame K is compared with one based on aspartame the taste will be different. In practice acesulfame K is not normally used on its own but is sometimes used with aspartame. Chemically, acesulfame K is the potassium salt of 6-methyl-l,2,3-oxathiazine-4(3//)-one-2,2 dioxide or 3,4-dihydro-6-methyl-l,2,3-oxathiazine-4-one 2,2-dioxide. It can be regarded as a derivative of acetoacetic acid. The empirical formula is C4H4N04KS and its molecular weight is 201.2. 

Acesulfame-K. Acesulfame-K [55589-62-3] (4), the potassium salt of acesulfame [33665-90-6] (6-methyl-l,2,3-oxathiazin-4(3Ff)-one 2,2-dioxide), is a sweetener that resembles saccharin in structure and taste profile. 5,6-Dimethyl-l,2,3-oxathiazine-4(3 H)-one 2,2-dioxide, the first of many sweet compounds belonging to the dihydrooxathiazinone dioxide class, was discovered accidentally in 1967 (63). From these many sweet compounds, acesulfame was chosen for commercialization. To improve water solubility, 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, frozen and refrigerated desserts, and baked goods. 

Chemical Name 6-Methyl-l,2,3-oxathiazin-4(3H)-one 2,2-dioxide potassium... 

APM-Ace [2-carboxy- 3-(A-(/>-methoxycarbonyl-2-phenyl)eth-ylcarbamoyl)]ethanaminium 6-methyl-4-oxo-l,2,3-oxathiazin-3-ide-2,2-dioxide L-Phenylalanine, L-a-aspartyl-2-methyl ester compound with 6-methyl-l,2,3-oxathiazin-4(3H)-one 2,2-di-oxide (1 1)... 

Arsenic Specifications Policy, 2 Arsenic Test, 755 Ascorbic Acid, 33 l-Ascorbic Acid, 33 Ascorbyl Palmitate, 34 Ash (Acid-Insoluble), 748 Ash (Total), 748 L-Asparagine, 35 Aspartame, 35, (Sl)4 Aspartame-Acesulfame Salt, (S3)5, 96 dl-Aspartic Acid, 36, (S3)7 l-Aspartic Acid, 37, (S2)l, (S3)7 L-a-Aspartyl-2-methyl ester Compound with 6-Methyl-l,2,3-oxathiazin-4(3H)-one 2,2-Dioxide (1 1), (S3)5 A-L-a-Aspartyl-L-phenylalamnc 1-Methyl Ester, 35, (S1 )4... 

Acesulfame-K is the potassium salt of 6-methyl-l,2,3-oxathiazin-4(3H)-one-2,2-dioxide. This sweetener was discovered in Germany and was first approved by the FDA in 1988 for use as a nonnutritive sweetener. The complex chemical name of this substance led to the creation of the trademark common name, acesulfame-K, which is based on its following relationships to acetocetic acid and sulfanic acid, and to its potassium salt nature [9] ... 

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. 

Methyl 2-(4-methoxyphenyl)-6-methy]-l,4,3-oxathiazine-5-carbox3flate (7) has been synthesized as the so far only example of this ring system.51 Treatment of 5-(4-mcthoxyphenyl)-l,3.4-oxathiazol-2-one (4) with methyl diazoacetoacetate in the presence of rhodium(II) acetate in refluxing benzene yields 4-methoxybenzonitrile (64%), 1,3-dithietanes (8, 25%), thiiranes (9, 5% cis/trans mixtures), and 6% of a compound C13H,3N04S, which was identified as 7 by X-ray analysis. 

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