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1,2-Dihydro-2-Ketobenzisosulphonazole
Also known as: 81-07-2, O-benzoic sulfimide, O-sulfobenzimide, Saccharine, Saccharimide, Benzosulfimide
Molecular Formula
C7H5NO3S
Molecular Weight
183.19  g/mol
InChI Key
CVHZOJJKTDOEJC-UHFFFAOYSA-N
FDA UNII
FST467XS7D

Flavoring agent and non-nutritive sweetener.
1 2D Structure

1,2-Dihydro-2-Ketobenzisosulphonazole

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,1-dioxo-1,2-benzothiazol-3-one
2.1.2 InChI
InChI=1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9)
2.1.3 InChI Key
CVHZOJJKTDOEJC-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC=C2C(=C1)C(=O)NS2(=O)=O
2.2 Other Identifiers
2.2.1 UNII
FST467XS7D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Calcium, Saccharin

2. Saccharin Calcium

3. Saccharin Sodium

2.3.2 Depositor-Supplied Synonyms

1. 81-07-2

2. O-benzoic Sulfimide

3. O-sulfobenzimide

4. Saccharine

5. Saccharimide

6. Benzosulfimide

7. Benzoic Sulfimide

8. Garantose

9. O-benzosulfimide

10. Benzosulphimide

11. Saccharinose

12. Saccharinol

13. Gluside

14. Benzosulfinide

15. Hermesetas

16. Saccharol

17. Glucid

18. Sweeta

19. Saccharin Acid

20. 1,2-benzisothiazol-3(2h)-one, 1,1-dioxide

21. Benzoic Sulphimide

22. Saccharin Insoluble

23. 1,2-benzisothiazol-3(2h)-one 1,1-dioxide

24. Kandiset

25. Sacarina

26. Sucrette

27. Zaharina

28. Saxin

29. Sykose

30. Benzo-2-sulphimide

31. O-benzoyl Sulfimide

32. Sucre Edulcor

33. O-benzoic Sulphimide

34. Benzoylsulfonic Imide

35. O-sulfobenzoic Acid Imide

36. O-benzosulphimide

37. Insoluble Saccharin

38. 550 Saccharine

39. Sacharin

40. Natreen

41. O-benzoyl Sulphimide

42. Anhydro-o-sulfaminebenzoic Acid

43. 2,3-dihydro-3-oxobenzisosulfonazole

44. 2-sulphobenzoic Imide

45. Benzoic Acid Sulfimide

46. Benzo[d]isothiazol-3(2h)-one 1,1-dioxide

47. 1,1-dioxo-1,2-benzothiazol-3-one

48. 1,2-dihydro-2-ketobenzisosulfonazole

49. 3-benzisothiazolinone 1,1-dioxide

50. 3-hydroxybenzisothiazole S,s-dioxide

51. 2,3-dihydro-3-oxobenzisosulphonazole

52. 1,2-dihydro-2-ketobenzisosulphonazole

53. 2-sulfobenzoic Acid Imide

54. Rcra Waste Number U202

55. Saccharin, Insoluble

56. 1,2-benzisothiazolin-3-one 1,1-dioxide

57. Saccharin Sodium

58. 3-hydroxybenzisothiazole-s,s-dioxide

59. Saccharinum

60. Syncal

61. O-benzoic Acid Sulfimide

62. Benzo-sulphinide

63. Cristallose

64. Crystallose

65. Kristallose

66. Willosetten

67. Madhurin

68. Sucromat

69. Sodium Saccharin

70. Saccharin Soluble

71. Sodium Saccharide

72. Sodium Saccharine

73. Soluble Saccharin

74. 1,2-benzisothiazolin-3-one, 1,1-dioxide

75. Saccharine Soluble

76. Sodium Saccharinate

77. Nsc-5349

78. Fst467xs7d

79. Saccharin, Sodium Salt

80. Sodium O-benzosulfimide

81. 1,1-dioxide-1,2-benzisothiazolin-3-one

82. Chembl310671

83. 1,1-dioxo-1,2-benzisothiazol-3(2h)-one

84. 1,2-benzothiazol-3(2h)-one 1,1-dioxide

85. Ins No.954(i)

86. Chebi:32111

87. O-sulfonbenzoic Acid Imide Sodium Salt

88. Ins-954(i)

89. 1,1-dioxo-1,2-dihydro-benzo[d]isothiazol-3-one

90. 1,1-diox-1,2-benzisothiazol-3-one

91. 2,3-dihydroxy-1,2-benzisothiazol-3-one-1,1-dioxide

92. Ncgc00094918-03

93. E-954(i)

94. E954

95. 1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[d]-isothiazol-3-one

96. Saccharin, Soluble

97. 1,2-benzisothiazoline-3-one 1,1-dioxide

98. Dsstox_cid_1251

99. 1,1-dioxide-1,2-benzisothiazol-3(2h)-one

100. Dsstox_rid_76039

101. Sacharin [czech]

102. Dsstox_gsid_21251

103. Saccharin And Salts

104. Benzosulfimide, O-

105. Saccharin [usan]

106. Sulfobenzimide, O-

107. 2,3-dihydro-1$l^{6},2-benzothiazole-1,1,3-trione

108. 2,3-dihydro-1,2-benzoisothiazol-3-one-1,1-dioxide

109. Artificial Sweetening Substanz Gendorf 450

110. Sodium 1,2 Benzisothiazolin-3-one 1,1-dioxide

111. 128-44-9

112. Cas-81-07-2

113. Saccharin [nf]

114. Nsc4867

115. Nsc5731

116. Lsa

117. Hsdb 669

118. Tolunene-2-sulfonamide

119. Nsc 5349

120. Nsc 5731

121. Einecs 201-321-0

122. Rcra Waste No. U202

123. Unii-fst467xs7d

124. Glycophenol

125. Neosaccharin

126. Ai3-38107

127. Sr-01000389315

128. Dtxsid5021251

129. Benzo-2-sulfiide

130. O-benzoylsulfimide

131. Saccharin Nitranion

132. 2-sulfobenzoicimide

133. O-sulfobenzoic Imide

134. Sweeta (tn)

135. O-sulphobenzoic Imide

136. 2-sulfobenzoic Imide

137. Spectrum_000213

138. Saccharin, >=98%

139. Saccharin, >=99%

140. Saccharin [fcc]

141. Saccharin [jan]

142. Saccharin [ii]

143. Saccharin [mi]

144. Saccharin [hsdb]

145. Saccharin [iarc]

146. Saccharin [inci]

147. Saccharin (jp15/nf)

148. Saccharin (jp17/nf)

149. Spectrum2_001432

150. Spectrum3_001475

151. Spectrum4_000449

152. Spectrum5_001181

153. Saccharin [vandf]

154. Saccharinum [hpus]

155. Saccharin [mart.]

156. Wln: T56 Bswmvj

157. Ec 201-321-0

158. Saccharin [usp-rs]

159. Saccharin [who-dd]

160. Schembl3816

161. Saccharin, Puriss., 98%

162. Nciopen2_005140

163. Nciopen2_005180

164. Bspbio_003029

165. Kbiogr_000838

166. Kbioss_000693

167. Divk1c_000164

168. Spectrum1501171

169. Spbio_001564

170. Gtpl5432

171. Saccharin [ep Monograph]

172. Bdbm29278

173. Hms500i06

174. Kbio1_000164

175. Kbio2_000693

176. Kbio2_003261

177. Kbio2_005829

178. Kbio3_002529

179. Nsc5349

180. 2q38

181. Ninds_000164

182. 1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[d]isothiazol-3-one

183. Hms1921n03

184. Hms2092j09

185. Pharmakon1600-01501171

186. Bcp29068

187. Hy-y0272

188. Str03759

189. Zinc2560357

190. 3-benzisothiazolinone 1, 1-dioxide

191. O-benzoic Sulfimide;o-sulfobenzimide

192. Tox21_111358

193. Tox21_201880

194. Tox21_302950

195. Bbl015343

196. Ccg-39011

197. Mfcd00005866

198. Nsc757878

199. S4819

200. Stk803263

201. 2, 3-dihydro-3-oxobenzisosulfonazole

202. 2,3-dihydro-3-oxo-benzisosulfonazole

203. Akos000120481

204. Akos017272711

205. Saccharin (only Persons Who Manufacture Are Subject, No Supplier Notification)

206. Tox21_111358_1

207. 1, 2-dihydro-2-ketobenzisosulfonazole

208. Db12418

209. Nsc-757878

210. Idi1_000164

211. 1.2-benzoisothiazole-3-on-1.1-dioxide

212. Benzisosulfonazole, 2,3-dihydro-3-oxo-

213. Ncgc00094918-01

214. Ncgc00094918-02

215. Ncgc00094918-04

216. Ncgc00094918-05

217. Ncgc00094918-06

218. Ncgc00094918-07

219. Ncgc00094918-09

220. Ncgc00256329-01

221. Ncgc00259429-01

222. 1,2-benzisothiazoline-3-one-1,1-dioxide

223. 1.2 -benzoisothiazole-3-on 1.1-dioxide

224. Sbi-0051671.p002

225. 1, 2-benzisothiazolin-3-one 1,1-dioxide

226. 1,2-benzisothiazol-3(2h)-one-1,1-dioxide

227. B0004

228. Cs-0013120

229. Ft-0674493

230. Ft-0674494

231. D01085

232. D70140

233. 1, 2-benzisothiazol-3(2h)-one, 1,1-dioxide

234. 3-keto-2h,3h-1,2-benzisothiazole 1,1-dioxide

235. Ab00052233-04

236. Ab00052233_05

237. 2,3-dihydro-1??,2-benzothiazole-1,1,3-trione

238. Q191381

239. Saccharin (229 Degrees C) Melting Point Standard

240. 1,1-dioxido-3-oxo-2,3-dihydrobenzo[d]isothiazole

241. 1,2-benzisothiazol-3(2h)-one 1,1-dioxide, 9ci

242. 2,3-dihydro-1,2-benzisothiazol-3-one-1,1-dioxide

243. 2,3-dihydro-3-oxo-1,2-benzisothiazol-1,1-dioxide

244. Sr-01000389315-2

245. W-200289

246. 03ac8ec2-d02a-464c-a7c3-7cabd643cc1e

247. 2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione

248. Brd-k46493214-001-03-4

249. 1, 2-benzisothiazolin-3-one, 1,1-dioxide, Sodium Salt

250. 1, 2-benzothiazol-3(2h)-one 1,1-dioxide Sodium Salt

251. F0001-2092

252. Z256708526

253. 1, 2-benzisothiazol-3(2h)-one, 1,1-dioxide, Sodium Salt

254. 1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one

255. Saccharin, European Pharmacopoeia (ep) Reference Standard

256. Mettler-toledo Calibration Substance Me 51143091, Saccharin

257. Saccharin, United States Pharmacopeia (usp) Reference Standard

258. Saccharin, Pharmaceutical Secondary Standard; Certified Reference Material

259. Mettler-toledo Calibration Substance Me 51143091, Saccharin, Traceable To Primary Standards (lgc)

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 183.19 g/mol
Molecular Formula C7H5NO3S
XLogP30.9
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count0
Exact Mass182.99901420 g/mol
Monoisotopic Mass182.99901420 g/mol
Topological Polar Surface Area71.6 Ų
Heavy Atom Count12
Formal Charge0
Complexity303
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Sweetening Agents

Substances that sweeten food, beverages, medications, etc., such as sugar, saccharine or other low-calorie synthetic products. (From Random House Unabridged Dictionary, 2d ed) (See all compounds classified as Sweetening Agents.)


4.2 Absorption, Distribution and Excretion

TRANSPLACENTAL TRANSFER OF ... (14)C-SACCHARIN ADMIN BY IV INFUSION TO RHESUS MONKEYS IN LATE PREGNANCY, WAS RAPID, BUT SLIGHT. (14)C WAS CLEARED MORE SLOWLY FROM FETAL THAN FROM MATERNAL BLOOD, & WAS DISTRIBUTED IN ALL FETAL TISSUES EXAMINED ... WAS ONLY BIOTRANSFORMED TO LIMITED EXTENT & WAS RAPIDLY EXCRETED ... .

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 2: A Review of the Literature Published Between 1970 and 1971. London: The Chemical Society, 1972., p. 150


Three groups of five men were given sodium saccharin in single oral doses of 50, 150 or 333 mg/60 kg bw. Peak plasma concentrations occurred between 30 and 60 min after dosing, and 60 and 76% was excreted unchanged in urine at 6 and 24 h, respectively. /Sodium saccharin/

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 570 (1999)


IN 3 VOLUNTEERS, 85-92% OF DOSES OF 1 G 3(14)C-SACCHARIN ADMIN ORALLY FOR 21 DAYS WAS EXCRETED UNCHANGED IN THE URINE WITHIN 24 HR; NO METABOLITES WERE FOUND. WITHIN 48 HR, 92.3% OF A DOSE OF 500 MG (14)C-SACCHARIN WAS EXCRETED IN THE URINE & 5.8% IN THE FECES.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V22 151 (1980)


After administration of 1-g doses of soluble (sodium) saccharin [form not specified] to three men, saccharin was excreted in the urine quantitatively unchanged by two of the subjects within 48 hr. In a subsequent experiment involving six subjects, none excreted the dose quantitatively within 72 hr, but no metabolism of saccharin was detected. /Sodium saccharin/

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 570 (1999)


For more Absorption, Distribution and Excretion (Complete) data for SACCHARIN (13 total), please visit the HSDB record page.


4.3 Metabolism/Metabolites

... 3-(14)C-SACCHARIN WAS EXCRETED UNCHANGED, MAINLY IN THE URINE (85-92% IN 24 HR) BY ADULT HUMAN SUBJECTS, BOTH BEFORE & AFTER TAKING 1 G OF SACCHARIN DAILY FOR 21 DAYS; NO METABOLITE OF SACCHARIN WAS FOUND. THESE RESULTS WERE AMPLY CONFIRMED IN ANIMAL EXPERIMENTS, IN WHICH ORALLY ADMIN (14)C-SACCHARIN WAS EXCRETED ENTIRELY UNCHANGED BY RATS ON A NORMAL DIET & BY RATS ON A DIET CONTAINING 1% & 5% OF SACCHARIN FOR UP TO 12 MO. 80-90% OF THE DOSE WAS EXCRETED IN THE URINE, 10-20% IN THE FECES; NO (14)CO2 WAS FOUND IN THE EXHALED AIR, & NO (14)CO3(2-) OR 2-SULFAMOYLBENZOIC ACID IN THE URINE.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 419


YIELDS IN MONKEYS SULFAMOYLBENZOIC ACID & O-SULFOBENZOIC ACID. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. S-1


EXPOSURE OF MALE CHARLES RIVER CDI RATS TO 5% SACCHARIN DIET IN UTERO & THROUGHOUT WEANING, DID NOT INDUCE DETECTABLE METABOLISM. NO METABOLITES WERE DETECTED IN URINE OF NORMAL RATS GIVEN TRACER DOSE. PRETREATMENT WITH 3-METHYLCHOLANTHRENE DID NOT INDUCE SACCHARIN METABOLISM.

PMID:472722 SWEATMAN TW, RENWICK AG; SCIENCE 205 (4410): 1019 (1979)


One female and two male volunteers excreted 85-92% of a dose of 1g (3-14)C- saccharin unchanged in the urine within 24 hr, before or after taking 1 g saccharin daily for 21 days; no metabolites were found.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 570 (1999)


Within 48 h, 92% of a dose of 500 mg [14C]saccharin taken by six male volunteers was excreted in the urine and 5.8% in the faeces. Analysis of urine and feces by highperformance liquid chromatography and thin-layer chromatography revealed only unmetabolized saccharin.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 570 (1999)


4.4 Biological Half-Life

In three adult men given an intravenous bolus of 10 mg/kg bw sodium saccharin, the plasma concentration-time curve fitted a two-compartment open model with a terminal half-life of 70 min. /Sodium saccharin/

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 570 (1999)


Six women with an average oral daily intake of 100-300 mg saccharin (form not specified) had maximum plasma concentrations after 0.5-1 hr and an elimination half-life of 7.5 hr.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V73 569 (1999)


4.5 Mechanism of Action

...it has been shown that the activation of particular T2R bitter taste receptors is partially involved with the bitter aftertaste sensation of saccharin and acesulfame-K. ... /This study/ addressed the question of whether /they/ could stimulate transient receptor potential vanilloid-1 (TRPV1) receptors, as these receptors are activated by a large range of structurally different chemicals. Moreover, TRPV1 receptors and/or their variants are found in taste receptor cells and in nerve terminals throughout the oral cavity. Hence, TRPV1 activation could be involved in the ... aftertaste or even contribute to the poorly understood metallic taste sensation. Using Ca(2+) imaging on TRPV1 receptors heterologously expressed in the human embryonic kidney (HEK) 293 cells and on dissociated primary sensory neurons,... /it was found/ that in both systems, .../sweeteners/ activate TRPV1 receptors, and, moreover, they sensitize these channels to acid and heat. ... /it was/also found that TRPV1 receptors were activated by CuSO(4), ZnSO(4), and FeSO(4), three salts known to produce a metallic taste sensation. In summary, .../the/ results identify a novel group of compounds that activate TRPV1 and, consequently, provide a molecular mechanism that may account for off tastes of sweeteners and metallic tasting salts.

Riera CE, et al; Am J Physiol Regul Integr Comp Physiol 293 (2): R626-34 (2007)


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