37. Acesulfame

Nomenclature

CAS number: 33665-90-6
6-Methyl-1,2,3-oxathiazin-4(3H)-one 2,2-dioxide; 6-methyl-3,4-dihydro-1,2,3-oxathiazin-4-one 2,2-dioxide; acetosulfam.
C4H5NO4S; mol wt 163.15.
C 29.45%, H 3.09%, N 8.59%, O 39.23%, S 19.65%.

Description and references

Non-nutritive artificial sweetener. Prepn: K. Clauss, H. Jensen, DE 2001017; eidem, US 3689486 (1971, 1972 to Hoechst); K. Clauss et al., Z. Lebensm.-Unters. Forsch. 162, 37 (1976) DOI PubMed. Crystal structure: E. F. Paulus, Acta Crystallogr. B31, 1191 (1975). HPLC analysis: H. Grosspietsch, H. Hachenberg, Z. Lebensm.-Unters. Forsch. 171, 41 (1980) DOI. Book: Acesulfame-K, D. G. Mayer, F. H. Kemper, Eds. (Marcel Dekker, Inc., New York, 1991) 243 pp.

Chemical structure

Properties

Needles from benzene or chloroform, mp 123-123.5°.

Derivative

Potassium salt.

Nomenclature

CAS number: 55589-62-3
Acesulfame-K; HOE-095K; Sunette (Hoechst).
C4H4KNO4S; mol wt 201.24.
C 23.87%, H 2.00%, K 19.43%, N 6.96%, O 31.80%, S 15.93%.

Properties

Colorless, odorless powder. Dec pt ≈225°. d (solid) 1.81 g/cm3; d (bulk) 1.1-1.3 kg/dm3. uv max: 227 nm (ε 1.0762×104). Very sol in DMF, DMSO. Sol in water, glycerin-water. Very slightly sol in acetone, alcohol. Soly in water (g/l): ≈150 (0°); ≈210 (10°); ≈270 (20°); ≈360 (30°); ≈460 (40°); ≈580 (50°); ≈830 (70°); ≈1300 (100°). Soly at 20° (g/l): methanol ≈10; ethanol (anhydrous) ≈1; glycerol (anhydrous) ≈30; glycerol/water (80:20, v/v) ≈82; glycerol/water (50:50, v/v) ≈162; acetone ≈0.8; glacial acetic acid ≈130. Soly at 23° (g/l): ethanol/water (80:20, v/v) ≈46; ethanol/water (60:40, v/v) ≈100; ethanol/water (40:60, v/v) ≈155; ethanol/water (20:80, v/v) ≈221. LD50 in rats (mg/kg): 7431 orally, 2243 i.p. (Mayer, Kemper).

Use

Potassium salt as sweetener for foods, cosmetics.