FComEx: Saccharin (PC001221)

Record Information

Version

1.0

Creation date

2018-05-02 12:54:50 UTC

Update date

2018-05-04 14:12:50 UTC

FoodComEx ID

PC001221

FoodDB Record

FDB000918

Chemical Information

Name

Saccharin

Description

Widely-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 Number

81-07-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
1, 2-Benzisothiazol-3(2H)-one, 1,1-dioxide	biospider
1, 2-Benzisothiazolin-3-one 1,1-dioxide	biospider
1, 2-Dihydro-2-ketobenzisosulfonazole	biospider
1,1-Diox-1,2-benzisothiazol-3-one	biospider
1,1-Dioxide-1,2-benzisothiazol-3(2H)-one	biospider
1,1-Dioxide-1,2-benzisothiazolin-3-one	biospider
1,1-Dioxo-1,2-benzisothiazol-3(2H)-one	biospider
1,1-Dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one	biospider
1,1-Dioxo-1,2-dihydro-benzo[d]isothiazol-3-one	biospider
1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 9CI	db_source
1,2-Benzisothiazol-3(2H)-one, 1,1-dioxide	biospider
1,2-Benzisothiazolin-3-one 1,1-dioxide	biospider
1,2-Benzisothiazolin-3-one, 1,1-dioxide	biospider
1,2-Benzisothiazoline-3-one 1,1-dioxide	biospider
1,2-Benzothiazol-3(2H)-one 1,1-dioxide	biospider
1,2-Dihydro-2-ketobenzisosulfonazole	biospider
1,2-Dihydro-2-ketobenzisosulphonazole	biospider
2-Sulfobenzoic acid imide	biospider
2-Sulfobenzoicimide	biospider
2-Sulphobenzoic imide	biospider
2, 3-Dihydro-3-oxobenzisosulfonazole	biospider
2,3-Dihydro-1,2-benzoisothiazol-3-one-1,1-dioxide	biospider
2,3-Dihydro-3-oxobenzisosulfonazole	biospider
2,3-Dihydro-3-oxobenzisosulphonazole	biospider
2,3-Dihydroxy-1,2-benzisothiazol-3-one-1,1-dioxide	biospider
3-Benzisothiazolinone 1, 1-dioxide	biospider
3-Benzisothiazolinone 1,1-dioxide	biospider
3-Hydroxybenzisothiazole S,S-dioxide	biospider
3-Hydroxybenzisothiazole-S,S-dioxide	biospider
Anhydro-o-sulfaminebenzoic acid	biospider
Benzisosulfonazole, 2,3-dihydro-3-oxo-	biospider
Benzo-2-sulfiide	biospider
Benzo-2-sulphimide	biospider
Benzo-sulphinide	biospider
Benzoic acid sulfimide	biospider
Benzoic sulfimide	db_source
Benzoic sulphimide	biospider
Benzosulfimide	biospider
Benzosulfimide, o-	biospider
Benzosulfinide	db_source
Benzosulphimide	biospider
Benzoylsulfonic imide	biospider
E954	db_source
Garantose	db_source
Glucid	biospider
Gluside	biospider
Glycophenol	biospider
Hermesetas	db_source
Insoluble saccharin	biospider
Kandiset	biospider
LSA	biospider
Neosaccharin	biospider
O-benzoic acid sulfimide	biospider
O-benzoic sulfimide	biospider
O-benzoic sulphimide	biospider
o-Benzosulfimide	db_source
O-benzosulphimide	biospider
O-benzoyl sulfimide	biospider
O-benzoyl sulphimide	biospider
o-Benzoylsulfimide	db_source
O-sulfobenzimide	biospider
O-sulfobenzoic acid imide	biospider
o-Sulfobenzoic imide	db_source
Sacarina	biospider
Saccharimide	biospider
Saccharin (JP15/NF)	biospider
Saccharin [usan]	biospider
Saccharin acid	biospider
Saccharin insoluble	biospider
Saccharin, insoluble	biospider
Saccharine	biospider
Saccharinol	biospider
Saccharinose	biospider
Saccharol	biospider
Sacharin	biospider
Stilalgin	biospider
Sucre edulcor	biospider
Sucrette	biospider
Sulfobenzimide, o-	biospider
Sweeta	db_source
Syncal	biospider
Zaharina	biospider

Chemical Formula

C7H5NO3S

IUPAC name

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

InChI Identifier

InChI=1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9)

InChI Key

CVHZOJJKTDOEJC-UHFFFAOYSA-N

Isomeric SMILES

O=C1NS(=O)(=O)C2=C1C=CC=C2

Average Molecular Weight

183.185

Monoisotopic Molecular Weight

182.999013721

Chemical Taxonomy

Description

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).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzothiazoles

Sub Class

Not Available

Direct Parent

Benzothiazoles

Alternative Parents