Saccharin
Title: Saccharin
CAS Registry Number: 81-07-2
CAS Name: 1,2-Benzisothiazol-3(2H)-one 1,1-dioxide
Additional Names: 2,3-dihydro-3-oxobenzisosulfonazole; 1,2-dihydro-2-ketobenzisosulfonazole; saccharin insoluble; benzosulfimide; o-sulfobenzimide; benzoic sulfimide; o-sulfobenzoic acid imide
Trademarks: Gluside; Glucid; Garantose; Saccharinol; Saccharinose; Saccharol; Saxin (Burroughs Wellcome); Sykose; Hermesetas
Molecular Formula: C7H5NO3S
Molecular Weight: 183.18
Percent Composition: C 45.90%, H 2.75%, N 7.65%, O 26.20%, S 17.50%
Literature References: Prepn from o-sulfamoylbenzoic acid: Remsen, Fahlberg, Ber. 12, 470 (1879). History and comparison with other sweetening agents: R. W. Moncrieff, The Chemical Senses (Wiley, New York, 1946). Mfg processes: O. Beyer, Handbuch der Saccharinfabrikation (Rascher, Zürich, 1923); FIAT Report PB 901 (1945); Chem. Eng. (N.Y.) 61, 128, 150 (July 1954). Maumee Chemical's process: Chem. Eng. News 41, 76-78 (Dec. 9, 1963). Stability studies: DeGarmo et al., J. Am. Pharm. Assoc. Sci. Ed. 41, 17 (1952). Toxicity data: J. D. Taylor et al., Food Cosmet. Toxicol. 6, 313 (1968). Series of articles on toxicology and metabolism: Food Chem. Toxicol. 23, 419-546 (1985). Review of toxicology and carcinogenicity studies of saccharin and its salts: IARC Monographs 22, 111-170 (1980); D. L. Arnold, Fundam. Appl. Toxicol. 4, 674-685 (1984). Review: R. Mazur, "Sweeteners" in Kirk-Othmer Encyclopedia of Chemical Technology vol. 22 (John Wiley & Sons, New York, 3rd ed., 1983) pp 448-464.
Properties: Monoclinic crystals, mp 228.8-229.7°. Twinning on (001). Perfect 100 cleavage. Acicular crystals by vacuum sublimation. In dil aq soln it is 500 times as sweet as sugar; the sweet taste is still detectable in 1:100,000 dilution. Bitter, metallic aftertaste. d 0.828. Heat of combustion at constant volume: 4753.1 cal/g. uv max (0.1N NaOH): 267.3 nm (e 1570). One gram dissolves in 290 ml water, 25 ml boiling water, 31 ml alcohol, 12 ml acetone, about 50 ml glycerol; freely sol in solns of alkali carbonates; slightly sol in chloroform, ether. pH of 0.35% aq soln 2.0. Hydrolysis products of saccharin are o-sulfamoylbenzoic acid (alkaline hydrolysis) and ammonium o-sulfobenzoic acid (acid hydrolysis).
Melting point: mp 228.8-229.7°
Absorption maximum: uv max (0.1N NaOH): 267.3 nm (e 1570)
Density: d 0.828
 
Derivative Type: Ammonium salt
Additional Names: Saccharin ammonium
Trademarks: Daramin; Sucline (Soekami)
Molecular Formula: C7H8N2O3S
Molecular Weight: 200.22
Percent Composition: C 41.99%, H 4.03%, N 13.99%, O 23.97%, S 16.01%
 
Derivative Type: Sodium salt dihydrate
Additional Names: Soluble saccharin; saccharin sodium
Trademarks: Kristallose; Crystallose (Tenneco); Dagutan; Sucaryl (Abbott); Sucromat (Mayoly-Spindler)
Molecular Formula: C7H4NNaO3S.2H2O
Molecular Weight: 241.20
Percent Composition: C 34.86%, H 3.34%, N 5.81%, Na 9.53%, O 33.17%, S 13.29%
Properties: Crystalline powder; effloresces in dry air. In dil aq soln it is 300-500 times as sweet as sugar. One gram dissolves in 1.2 ml water, in about 50 ml alcohol. Aq solns are neutral or alkaline to litmus, but not alkaline to phenolphthalein. LD50 in mice, rats (g/kg): 6.3, 7.1 i.p.; 17.5, 17.0 orally (Taylor). Anhydrous form, Sucrédulcor (Europ. Med.) .
Toxicity data: LD50 in mice, rats (g/kg): 6.3, 7.1 i.p.; 17.5, 17.0 orally (Taylor)
 
NOTE: Saccharin was formerly listed as reasonably anticipated to be a human carcinogen: Eighth Report on Carcinogens (PB99-128746, 1998) p III-905; delisted because the cancer data are not sufficient to meet the current criteria for this listing: Ninth Report on Carcinogens (PB2000-107509, 2000) p B-3.
Use: Non-nutritive sweetener; pharmaceutic aid (flavor). In formulations for electroplating-bath brighteners.

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