Saccharin
PubChem CID: 5143
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| Compound Synonyms | saccharin, 81-07-2, o-Benzoic sulfimide, Saccharine, o-Sulfobenzimide, Saccharimide, Benzosulfimide, Garantose, o-Benzosulfimide, Benzoic sulfimide, Benzosulphimide, Saccharinol, Saccharinose, Gluside, Saccharin insoluble, Benzosulfinide, Hermesetas, Saccharol, Glucid, Sweeta, Benzoic sulphimide, Kandiset, Sacarina, Sucrette, Zaharina, Sykose, Saxin, Saccharin acid, o-Benzoyl sulfimide, Sucre edulcor, 1,2-Benzisothiazol-3(2H)-one, 1,1-dioxide, Benzo-2-sulphimide, Benzoylsulfonic Imide, o-Benzosulphimide, Insoluble saccharin, 1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, Natreen, Sacharin, o-Benzoic sulphimide, o-Benzoyl sulphimide, o-Sulfobenzoic acid imide, 2-Sulphobenzoic imide, 2,3-Dihydro-3-oxobenzisosulfonazole, 550 Saccharine, Anhydro-o-sulfaminebenzoic acid, Benzo[d]isothiazol-3(2H)-one 1,1-dioxide, Benzoic acid sulfimide, 1,2-Dihydro-2-ketobenzisosulfonazole, 3-Benzisothiazolinone 1,1-dioxide, Benzosulfimide, O-, Rcra waste number U202, Sulfobenzimide, O-, 3-Hydroxybenzisothiazole S,S-dioxide, 1,1-dioxo-1,2-benzothiazol-3-one, Saccharinum, 2,3-Dihydro-3-oxobenzisosulphonazole, 1,2-Dihydro-2-ketobenzisosulphonazole, Benzo-sulphinide, 1,2-Benzisothiazolin-3-one 1,1-dioxide, 3-Hydroxybenzisothiazole-S,S-dioxide, 2-Sulfobenzoic acid imide, Saccharin, insoluble, SACCHARIN SODIUM, HSDB 669, Syncal, DTXSID5021251, o-Benzoic acid sulfimide, 1,2-Benzisothiazolin-3-one, 1,1-dioxide, UNII-FST467XS7D, NSC 5349, NSC 5731, NSC-5349, EINECS 201-321-0, FST467XS7D, Cristallose, Crystallose, Kristallose, Willosetten, Madhurin, Sucromat, Sodium saccharin, INS NO.954(I), CHEBI:32111, Saccharin soluble, Sodium saccharide, Sodium saccharine, Soluble saccharin, AI3-38107, Saccharine soluble, INS-954(I), Saccharin, sodium salt, E-954(I), Sodium o-benzosulfimide, 1,1-Dioxide-1,2-benzisothiazolin-3-one, CHEMBL310671, DTXCID401251, 1,1-Dioxo-1,2-benzisothiazol-3(2H)-one, 1,2-Benzothiazol-3(2H)-one 1,1-dioxide, 128-44-9, o-Sulfonbenzoic acid imide sodium salt, EC 201-321-0, 1,1-Dioxo-1,2-dihydro-benzo[d]isothiazol-3-one, 1,1-Diox-1,2-benzisothiazol-3-one, 2,3-Dihydroxy-1,2-benzisothiazol-3-one-1,1-dioxide, NCGC00094918-03, E954, SACCHARIN (II), SACCHARIN [II], Saccharin, soluble, 1,2-Benzisothiazoline-3-one 1,1-dioxide, SACCHARIN (IARC), SACCHARIN [IARC], 1,1-Dioxide-1,2-benzisothiazol-3(2H)-one, SACCHARIN (MART.), SACCHARIN [MART.], SACCHARIN (USP-RS), SACCHARIN [USP-RS], Sacharin [Czech], Saccharin [USAN], 2,3-dihydro-1$l^{6},2-benzothiazole-1,1,3-trione, 2,3-Dihydro-1,2-benzoisothiazol-3-one-1,1-dioxide, Artificial sweetening substanz gendorf 450, SACCHARIN (EP MONOGRAPH), SACCHARIN [EP MONOGRAPH], CAS-81-07-2, Saccharin [NF], NSC4867, NSC5731, LSA, 1,1-Dioxo-1,2-dihydro-benzo(d)isothiazol-3-one, RCRA waste no. U202, Glycophenol, Neosaccharin, SR-01000389315, ulfonylurea TP3, Benzo-2-sulfiide, O-Benzoylsulfimide, 2-Sulfobenzoicimide, M07 (saccharin), MFCD00005866, O-Sulfobenzoic imide, Sweeta (TN), o-sulphobenzoic imide, 2-Sulfobenzoic imide, Oxasulfuron metabolite, Saccharin (Standard), Spectrum_000213, Saccharin, >=98%, Saccharin, >=99%, SACCHARIN [FCC], SACCHARIN [JAN], SACCHARIN [MI], SACCHARIN [HSDB], Saccharin (JP15/NF), Saccharin (JP17/NF), Spectrum2_001432, Spectrum3_001475, Spectrum4_000449, Spectrum5_001181, SACCHARIN [VANDF], 1,2-benzisothiazol-3(2H)-one-1,1-dioxide, SACCHARINUM [HPUS], WLN: T56 BSWMVJ, SACCHARIN [WHO-DD], SCHEMBL3816, Saccharin, puriss., 98%, NCIOpen2_005140, NCIOpen2_005180, Saccharin (IN-00581), BSPBio_003029, KBioGR_000838, KBioSS_000693, DivK1c_000164, SPECTRUM1501171, SPBio_001564, GTPL5432, BDBM29278, HMS500I06, HY-Y0272R, KBio1_000164, KBio2_000693, KBio2_003261, KBio2_005829, KBio3_002529, NSC5349, 2q38, NINDS_000164, 1,1-Dioxo-1,2-dihydro-1lambda*6*-benzo[d]-isothiazol-3-one, 1,1-Dioxo-1,2-dihydro-1lambda*6*-benzo[d]isothiazol-3-one, HMS1921N03, HMS2092J09, Pharmakon1600-01501171, BCP29068, HY-Y0272, LBC47901, PXB46617, STR03759, 3-Benzisothiazolinone 1, 1-dioxide, o-Benzoic sulfimide, o-Sulfobenzimide, Tox21_111358, Tox21_201880, Tox21_302950, BBL015343, CCG-39011, NSC757878, s4819, STK803263, 2, 3-Dihydro-3-oxobenzisosulfonazole, 2,3-Dihydro-3-oxo-Benzisosulfonazole, AKOS000120481, AKOS017272711, Saccharin (only persons who manufacture are subject, no supplier notification), Tox21_111358_1, 1, 2-Dihydro-2-ketobenzisosulfonazole, 1,2-Benzisothiazolinone, 1,1-Dioxide, DB12418, FS27775, NSC-757878, IDI1_000164, 1.2-benzoisothiazole-3-on-1.1-dioxide, Benzisosulfonazole, 2,3-dihydro-3-oxo-, NCGC00094918-01, NCGC00094918-02, NCGC00094918-04, NCGC00094918-05, NCGC00094918-06, NCGC00094918-07, NCGC00094918-09, NCGC00256329-01, NCGC00259429-01, 1,2-benzisothiazoline-3-one-1,1-dioxide, 1.2 -benzoisothiazole-3-on 1.1-dioxide, SBI-0051671.P002, 1, 2-Benzisothiazolin-3-one 1,1-dioxide, 1,2-benzisothiazol-3(2H)-one,1,1-dioxide, B0004, CS-0013120, NS00007781, 1,2-Benzisothiazol-3(2H) one 1,1-dioxide, EN300-18624, D01085, D70140, 1, 2-Benzisothiazol-3(2H)-one, 1,1-dioxide, 3-keto-2H,3H-1,2-benzisothiazole 1,1-dioxide, AB00052233-04, AB00052233_05, 1,2-Benzo(d)isothiazol-3(2H)-one 1,1-dioxide, 2,3-dihydro-1??,2-benzothiazole-1,1,3-trione, Q191381, Saccharin (229 degrees C) Melting Point Standard, 1,1-Dioxido-3-oxo-2,3-dihydrobenzo[d]isothiazole, 1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 9CI, 2,3-dihydro-1,2-benzisothiazol-3-one-1,1-dioxide, 2,3-dihydro-3-oxo-1,2-benzisothiazol-1,1-dioxide, SR-01000389315-2, 03AC8EC2-D02A-464C-A7C3-7CABD643CC1E, 2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione, BRD-K46493214-001-03-4, BRD-K46493214-001-06-7, 1, 2-Benzisothiazolin-3-one, 1,1-dioxide, sodium salt, 1, 2-Benzothiazol-3(2H)-one 1,1-dioxide sodium salt, F0001-2092, Z256708526, 1, 2-Benzisothiazol-3(2H)-one, 1,1-dioxide, sodium salt, 1,1-dioxo-1,2-dihydro-1lambda6-benzo[d]isothiazol-3-one, Saccharin, European Pharmacopoeia (EP) Reference Standard, Mettler-Toledo Calibration substance ME 51143091, Saccharin, Saccharin, United States Pharmacopeia (USP) Reference Standard, Saccharin, Pharmaceutical Secondary Standard, Certified Reference Material, InChI=1/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9, 201-321-0, Mettler-Toledo Calibration substance ME 51143091, Saccharin, traceable to primary standards (LGC) |
|---|---|
| Ghose Rule | False |
| Classyfire Kingdom | Organic compounds |
| Topological Polar Surface Area | 71.6 |
| Hydrogen Bond Donor Count | 1.0 |
| Pfizer 3 75 Rule | False |
| Scaffold Graph Level | CC1CC(C)(C)C2CCCCC12 |
| Deep Smiles | O=CNS=O)=O)cc5cccc6 |
| Heavy Atom Count | 12.0 |
| Classyfire Class | Benzothiazoles |
| 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.". |
| Scaffold Graph Node Level | OC1NS(O)(O)C2CCCCC12 |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 303.0 |
| Database Name | fooddb_chem_all;hmdb_chem_all;imppat_phytochem;npass_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Uniprot Id | Q5VLE3, Q99873, P07451, P00915, P00918, Q16790, O43570, P53615, P9WPJ7, Q5AJ71, B5SU02, P9WPJ9, P02545, B2RXH2, Q03164, O75604, P23280, C0IX24, O75164, Q96KQ7, P10828, P11473, A6YCJ1, Q16236, O75496, Q9NUW8, Q9NPD5, Q9Y6L6, Q5U9J1, n.a., P22748, P35218, Q9Y2D0, P43166, Q9ULX7, P05067, P06276, Q5TU56, B2V8E3, Q31FD6, P59538, P0DTD1, P10275, Q03181 |
| Iupac Name | 1,1-dioxo-1,2-benzothiazol-3-one |
| Class | Benzothiazoles |
| Veber Rule | True |
| Classyfire Superclass | Organoheterocyclic compounds |
| Xlogp | 0.9 |
| Superclass | Organoheterocyclic compounds |
| Gsk 4 400 Rule | True |
| Molecular Formula | C7H5NO3S |
| Scaffold Graph Node Bond Level | O=C1NS(=O)(=O)c2ccccc21 |
| Inchi Key | CVHZOJJKTDOEJC-UHFFFAOYSA-N |
| Silicos It Class | Soluble |
| Rotatable Bond Count | 0.0 |
| State | Solid |
| Synonyms | 1, 2-Benzisothiazol-3(2H)-one, 1,1-dioxide, 1, 2-Benzisothiazolin-3-one 1,1-dioxide, 1, 2-Dihydro-2-ketobenzisosulfonazole, 1,1-Diox-1,2-benzisothiazol-3-one, 1,1-Dioxide-1,2-benzisothiazol-3(2H)-one, 1,1-Dioxide-1,2-benzisothiazolin-3-one, 1,1-Dioxo-1,2-benzisothiazol-3(2H)-one, 1,1-Dioxo-1,2-dihydro-1lambda*6*-benzo[d]isothiazol-3-one, 1,1-Dioxo-1,2-dihydro-benzo[d]isothiazol-3-one, 1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 9CI, 1,2-Benzisothiazol-3(2H)-one, 1,1-dioxide, 1,2-Benzisothiazolin-3-one 1,1-dioxide, 1,2-Benzisothiazolin-3-one, 1,1-dioxide, 1,2-Benzisothiazoline-3-one 1,1-dioxide, 1,2-Benzothiazol-3(2H)-one 1,1-dioxide, 1,2-Dihydro-2-ketobenzisosulfonazole, 1,2-Dihydro-2-ketobenzisosulphonazole, 2-Sulfobenzoic acid imide, 2-Sulfobenzoicimide, 2-Sulphobenzoic imide, 2, 3-Dihydro-3-oxobenzisosulfonazole, 2,3-Dihydro-1,2-benzoisothiazol-3-one-1,1-dioxide, 2,3-Dihydro-3-oxobenzisosulfonazole, 2,3-Dihydro-3-oxobenzisosulphonazole, 2,3-Dihydroxy-1,2-benzisothiazol-3-one-1,1-dioxide, 3-Benzisothiazolinone 1, 1-dioxide, 3-Benzisothiazolinone 1,1-dioxide, 3-Hydroxybenzisothiazole S,S-dioxide, 3-Hydroxybenzisothiazole-S,S-dioxide, Anhydro-o-sulfaminebenzoic acid, Benzisosulfonazole, 2,3-dihydro-3-oxo-, Benzo-2-sulfiide, Benzo-2-sulphimide, Benzo-sulphinide, Benzoic acid sulfimide, Benzoic sulfimide, Benzoic sulphimide, Benzosulfimide, Benzosulfimide, o-, Benzosulfinide, Benzosulphimide, Benzoylsulfonic imide, E954, Garantose, Glucid, Gluside, Glycophenol, Hermesetas, Insoluble saccharin, Kandiset, LSA, Neosaccharin, O-benzoic acid sulfimide, O-benzoic sulfimide, O-benzoic sulphimide, o-Benzosulfimide, O-benzosulphimide, O-benzoyl sulfimide, O-benzoyl sulphimide, o-Benzoylsulfimide, O-sulfobenzimide, O-sulfobenzoic acid imide, o-Sulfobenzoic imide, Sacarina, Saccharimide, Saccharin (JP15/NF), Saccharin [usan], Saccharin acid, Saccharin insoluble, Saccharin, insoluble, Saccharine, Saccharinol, Saccharinose, Saccharol, Sacharin, Stilalgin, Sucre edulcor, Sucrette, Sulfobenzimide, o-, Sweeta, Syncal, Zaharina, 1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 1,2-Benzisothiazol-3(2H)-one, 1,1-dioxide, ammonium salt, 2,3-dihydro-3-oxo-Benzisosulfonazole, ammonium 3-oxo-3H-1,2-benzisothiazol-2-ide 1,1-dioxide, Anhydro-O-sulfaminebenzoate, Anhydro-O-sulphaminebenzoate, Anhydro-O-sulphaminebenzoic acid, Benzo-2-sulfimide, Benzoate sulfimide, Benzoate sulphimide, Benzoic acid sulphimide, Benzoylsulphonic imide, O-Sulfobenzoate imide, O-Sulphobenzimide, O-Sulphobenzoate imide, O-Sulphobenzoic acid imide, Saccharin, 1,1-Dioxo-1,2-dihydro-benzo[D]isothiazol-3-one, Anhydro-O-sulfaminebenzoic acid, O-Benzoic sulfimide, O-Benzosulfimide, O-Sulfobenzimide, O-Sulfobenzoic acid imide, O-Benzoic sulphimide, O-Benzosulphimide, 1, 2-dihydro-2-Ketobenzisosulfonazole, 1,1-dioxo-1,2-dihydro-1Lambda*6*-benzo[D]isothiazol-3-one, 1,2-Benzisothiazol-3(2H)-one 1,1-dioxide, 9ci, 2, 3-dihydro-3-Oxobenzisosulfonazole, 2,3-dihydro-1,2-Benzoisothiazol-3-one-1,1-dioxide, benzo-2-Sulfiide, benzo-Sulphinide, e954, O-Benzoic acid sulfimide, O-Benzoyl sulfimide, O-Benzoyl sulphimide, O-Benzoylsulfimide, O-Sulfobenzoic imide, Saccharin (JP15/nf), Saccharin sodium, Saccharin calcium, Calcium, saccharin, saccharine |
| Substituent Name | 1,2-benzothiazole, Aralkylamine, Benzenoid, Sulfonic acid derivative, Sulfonamide, Carboxamide group, Azacycle, Carboxylic acid derivative, Hydrocarbon derivative, Organooxygen compound, Organonitrogen compound, Carbonyl group, Aromatic heteropolycyclic compound |
| Esol Class | Very soluble |
| Functional Groups | O=C1ccS(=O)(=O)N1 |
| Compound Name | Saccharin |
| Kingdom | Organic compounds |
| Exact Mass | 182.999 |
| Formal Charge | 0.0 |
| Monoisotopic Mass | 182.999 |
| Hydrogen Bond Acceptor Count | 3.0 |
| Molecular Weight | 183.19 |
| Gi Absorption | True |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Lipinski Rule Of 5 | True |
| Inchi | InChI=1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9) |
| Smiles | C1=CC=C2C(=C1)C(=O)NS2(=O)=O |
| Np Classifier Biosynthetic Pathway | Alkaloids |
| Defined Bond Stereocenter Count | 0.0 |
| Egan Rule | True |
| Taxonomy Direct Parent | Benzothiazoles |
- 1. Outgoing r'ship
FOUND_INto/from Asparagus Racemosus (Plant) Rel Props:Reference:ISBN:9780387706375 - 2. Outgoing r'ship
FOUND_INto/from Gmelina Arborea (Plant) Rel Props:Reference:ISBN:9781514271186