Record Information
Version1.0
Creation date2018-05-02 12:54:50 UTC
Update date2018-05-04 14:12:50 UTC
FoodComEx IDPC001221
FoodDB RecordFDB000918
Chemical Information
NameSaccharin
DescriptionWidely-used sweetening agent. All salts intensely sweet. Permitted in foods at levels of 80-1200 ppm in EU Although saccharin was commercialized not long after its discovery, it was not until sugar shortages during World War I that its use became widespread. Its popularity further increased during the 1960s and 1970s among dieters, since saccharin is a calorie-free sweetener. In the United States saccharin is often found in restaurants in pink packets; the most popular brand is "Sweet'N Low". A small number of soft drinks are sweetened with saccharin, the most popular[citation needed] being the Coca-Cola Company's cola drink Tab, introduced in 1963 as a diet cola soft drink.; Harvey Wiley was one particularly well-known figure involved in the investigation of saccharin. Wiley, then the director of the bureau of chemistry for the USDA, had suspected saccharin to be damaging to human health. Wiley first battled saccharin in 1908. In a clash that epitomizes the controversial history of saccharin, Harvey told then President Theodore Roosevelt directly that "Everyone who ate that sweet corn was deceived. He thought he was eating sugar, when in point of fact he was eating a coal tar product totally devoid of food value and extremely injurious to health." In a heated exchange, Roosevelt angrily answered Harvey by stating "Anybody who says saccharin is injurious to health is an idiot." In 1911, the Food Inspection Decision 135 stated that foods containing saccharin were adulterated. However in 1912, Food Inspection Decision 142 stated that saccharin was not harmful. The government's stance on saccharin has continued to waver ever since. More controversy was stirred in 1969 with the discovery of files from the Food and Drug Administration's investigations of 1948 and 1949. These investigations, which had originally argued against saccharin use, were shown to prove little about saccharin being harmful to human health. In 1972 the USDA made an attempt to completely ban the substance. However, this attempt was unsuccessful and the sweetener remains widely available in the United States; it is the third-most popular after sucralose and aspartame. Cyclamate, however, was banned in the US and saccharin was banned in Canada, leading to different product formulations being marketed in these countries.; Saccharin has the chemical formula C7H5NO3S and it can be produced in various ways. The original route starts with toluene, but yields from this starting point are low. In 1950, an improved synthesis was developed at the Maumee Chemical Company of Toledo, Ohio. In this synthesis, anthranilic acid successively reacts with nitrous acid, sulfur dioxide, chlorine, and then ammonia to yield saccharin. Another route begins with o-chlorotoluene. It is also known as ortho sulfobenzoic acid.; Saccharin is an acid with a pKa of about 2.; Saccharin is an artificial sweetener. The basic substance, benzoic sulfinide, has effectively no food energy and is much sweeter than sucrose, but has an unpleasant bitter or metallic aftertaste, especially at high concentrations. In countries where saccharin is allowed as a food additive, it is used to sweeten products such as drinks, candies, medicines, and toothpaste.; Saccharin was first produced in 1878 by Constantin Fahlberg, a chemist working on coal tar derivatives in Ira Remsen's laboratory at the Johns Hopkins University. It was Fahlberg who, accidentally, discovered its intensely sweet nature.[citation needed] Fahlberg and Remsen published articles on benzoic sulfinide in 1879 and 1880. In 1884, now working on his own in New York City, Fahlberg applied for patents in several countries describing methods of producing this substance that he named saccharin. Fahlberg would soon grow wealthy, while Remsen merely grew irate, believing that he deserved credit for substances produced in his laboratory. On the matter, Remsen commented, "Fahlberg is a scoundrel. It nauseates me to hear my name mentioned in the same breath with him."
CAS Number81-07-2
Structure
Thumb
Synonyms
SynonymSource
1, 2-Benzisothiazol-3(2H)-one, 1,1-dioxidebiospider
1, 2-Benzisothiazolin-3-one 1,1-dioxidebiospider
1, 2-Dihydro-2-ketobenzisosulfonazolebiospider
1,1-Diox-1,2-benzisothiazol-3-onebiospider
1,1-Dioxide-1,2-benzisothiazol-3(2H)-onebiospider
1,1-Dioxide-1,2-benzisothiazolin-3-onebiospider
1,1-Dioxo-1,2-benzisothiazol-3(2H)-onebiospider
1,1-Dioxo-1,2-dihydro-1lambda*6*-benzo[d]isothiazol-3-onebiospider
1,1-Dioxo-1,2-dihydro-benzo[d]isothiazol-3-onebiospider
1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 9CIdb_source
1,2-Benzisothiazol-3(2H)-one, 1,1-dioxidebiospider
1,2-Benzisothiazolin-3-one 1,1-dioxidebiospider
1,2-Benzisothiazolin-3-one, 1,1-dioxidebiospider
1,2-Benzisothiazoline-3-one 1,1-dioxidebiospider
1,2-Benzothiazol-3(2H)-one 1,1-dioxidebiospider
1,2-Dihydro-2-ketobenzisosulfonazolebiospider
1,2-Dihydro-2-ketobenzisosulphonazolebiospider
2-Sulfobenzoic acid imidebiospider
2-Sulfobenzoicimidebiospider
2-Sulphobenzoic imidebiospider
2, 3-Dihydro-3-oxobenzisosulfonazolebiospider
2,3-Dihydro-1,2-benzoisothiazol-3-one-1,1-dioxidebiospider
2,3-Dihydro-3-oxobenzisosulfonazolebiospider
2,3-Dihydro-3-oxobenzisosulphonazolebiospider
2,3-Dihydroxy-1,2-benzisothiazol-3-one-1,1-dioxidebiospider
3-Benzisothiazolinone 1, 1-dioxidebiospider
3-Benzisothiazolinone 1,1-dioxidebiospider
3-Hydroxybenzisothiazole S,S-dioxidebiospider
3-Hydroxybenzisothiazole-S,S-dioxidebiospider
Anhydro-o-sulfaminebenzoic acidbiospider
Benzisosulfonazole, 2,3-dihydro-3-oxo-biospider
Benzo-2-sulfiidebiospider
Benzo-2-sulphimidebiospider
Benzo-sulphinidebiospider
Benzoic acid sulfimidebiospider
Benzoic sulfimidedb_source
Benzoic sulphimidebiospider
Benzosulfimidebiospider
Benzosulfimide, o-biospider
Benzosulfinidedb_source
Benzosulphimidebiospider
Benzoylsulfonic imidebiospider
E954db_source
Garantosedb_source
Glucidbiospider
Glusidebiospider
Glycophenolbiospider
Hermesetasdb_source
Insoluble saccharinbiospider
Kandisetbiospider
LSAbiospider
Neosaccharinbiospider
O-benzoic acid sulfimidebiospider
O-benzoic sulfimidebiospider
O-benzoic sulphimidebiospider
o-Benzosulfimidedb_source
O-benzosulphimidebiospider
O-benzoyl sulfimidebiospider
O-benzoyl sulphimidebiospider
o-Benzoylsulfimidedb_source
O-sulfobenzimidebiospider
O-sulfobenzoic acid imidebiospider
o-Sulfobenzoic imidedb_source
Sacarinabiospider
Saccharimidebiospider
Saccharin (JP15/NF)biospider
Saccharin [usan]biospider
Saccharin acidbiospider
Saccharin insolublebiospider
Saccharin, insolublebiospider
Saccharinebiospider
Saccharinolbiospider
Saccharinosebiospider
Saccharolbiospider
Sacharinbiospider
Stilalginbiospider
Sucre edulcorbiospider
Sucrettebiospider
Sulfobenzimide, o-biospider
Sweetadb_source
Syncalbiospider
Zaharinabiospider
Chemical FormulaC7H5NO3S
IUPAC name2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione
InChI IdentifierInChI=1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9)
InChI KeyCVHZOJJKTDOEJC-UHFFFAOYSA-N
Isomeric SMILESO=C1NS(=O)(=O)C2=C1C=CC=C2
Average Molecular Weight183.185
Monoisotopic Molecular Weight182.999013721
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzothiazoles. These are organic compounds containing a benzene fused to a thiazole ring (a five-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassBenzothiazoles
Sub ClassNot Available
Direct ParentBenzothiazoles
Alternative Parents
Substituents
  • 1,2-benzothiazole
  • Benzenoid
  • Organosulfonic acid or derivatives
  • Organic sulfonic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logP0.91HANSCH,C ET AL. (1995)
Experimental Water Solubility4 mg/mL at 25 oCSEIDELL,A (1941)
Melting PointMp 224°DFC
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity Available1 to 2 mg
Delivery Time2 weeks
Storage Formpowder
Storage Conditions-18°C
StabilityNot Available
Purityunknown
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Augustin ScalbertInternational Agency for Research on Cancer (IARC), Biomarkers Group, 150 cours Albert Thomas, Lyon, FR, 69372scalberta@iarc.fr
Commercial Vendors
AKSci Z1771
Glentham GX2610
Toronto Research Chemicals S080800