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E 954, often used in the form of sodium saccharin, is an artificial sweetener with effectively no nutritional value.
E 954 is about 550 times as sweet as sucrose but has a bitter or metallic aftertaste, especially at high concentrations.
E 954 is used to sweeten products such as drinks, candies, cookies, and especially for masking the bitter taste of some medicines.
CAS: 81-07-2
MF: C7H5NO3S
MW: 183.18
EINECS: 201-321-0
E 954 was produced first in 1879, by Constantin Fahlberg, a chemist working on coal tar derivatives in Ira Remsen's laboratory at Johns Hopkins University.
Fahlberg noticed a sweet taste on his hand one evening, and connected this with the compound benzoic sulfimide on which he had been working that day.
Fahlberg and Remsen published articles on benzoic sulfimide in 1879 and 1880.
In 1884, then working on his own in New York City, Fahlberg applied for patents in several countries, describing methods of producing this substance that he named E 954.
Two years later, he began production of the substance in a factory in a suburb of Magdeburg in Germany.
Although E 954 was commercialized not long after its discovery, until sugar shortages during World War I, its use had not become widespread.
E 954's popularity further increased during the 1960s and 1970s among dieters, since saccharin is a calorie-free sweetener.
In the United States, E 954 is often found in restaurants in pink packets; the most popular brand is "Sweet'n Low".
Because of the difficulty of importing sugar from the West Indies, the British Saccharin Company was founded in 1917 to produce saccharin at E 954's Paragon Works near Accrington, Lancashire.
Production was licensed and controlled by the Board of Trade in London.
Production continued on the site until 1926.
Description
E 954 is an organic compound that is normally used as a non-nutritive sweetening agent.
Also known as ortho-sulfobenzoic acid imide, E 954 occurs in the form of various salts, mainly calcium and sodium.
A 1,2-benzisothiazole having a keto-group at the 3-position and two oxo substituents at the 1-position.
E 954 is used as an artificial sweetening agent.
A white crystalline solid,C7H5NO3S, m.p. 224°C.
E 954 is madefrom a compound of toluene, derivedfrom petroleum or coal tar.
E 954 is awell-known artificial sweetener,being some 500 times as sweet assugar (sucrose), and is usually marketedas its sodium salt.
Because ofan association with cancer in laboratoryanimals, E 954's use is restricted insome countries.
The utilization of E 954 in human food has raised numerous health and safety concerns.
In the 1970s, E 954 was linked with the development of bladder in rodents in various laboratory studies on rats.
Consequently, the United States Food and Drug Administration (FDA) pushed for its ban, sighting that E 954 is carcinogenic to humans.
However, after strong objection from the public regarding the ban, American Congress intervened and allowed the compound to remain in the food supply as long as all the manufactures libel E 954 with a warning when packaging.
E 954 gas been classified to have no nutritional or food energy value, as such, E 954 safe for patients with diabetes.
E 954 Chemical Properties
Melting point: 226-229 °C (lit.)
Boiling point: subl
Density: 0.828
Vapor pressure: 0Pa at 25℃
Refractive index: 1.5500 (estimate)
Storage temp.: Store below +30°C.
Solubility acetone: soluble1g in 12mL(lit.)
Form: Crystals or Crystalline Powder
pka: 11.68(at 18℃)
Color: White
Odor: odorless
Water Solubility: 3.3 g/L (20 ºC)
Merck: 14,8311
BRN: 6888
Stability: Stable. Incompatible with strong oxidizing agents.
InChIKey: CVHZOJJKTDOEJC-UHFFFAOYSA-N
LogP: -0.024 at 25℃
CAS DataBase Reference: 81-07-2(CAS DataBase Reference)
NIST Chemistry Reference: E 954 (81-07-2)
IARC: 3 (Vol. Sup 7, 73) 1999
EPA Substance Registry System: E 954 (81-07-2)
E 954 is heat-stable.
E 954 does not react chemically with other food ingredients; as such, it stores well.
Blends of E 954 with other sweeteners are often used to compensate for each sweetener's weaknesses and faults.
E 954 is common in countries where both these sweeteners are legal; in this blend, each sweetener masks the other's offtaste.
E 954 is often used with aspartame in diet carbonated soft drinks, so some sweetness remains should the fountain syrup be stored beyond aspartame's relatively short shelf life.
In its acid form, E 954 is not water-soluble.
The form used as an artificial sweetener is usually E 954' sodium salt.
The calcium salt is also sometimes used, especially by people restricting their dietary sodium intake.
Both salts are highly water-soluble: 0.67 g/ml in water at room temperature.
E 954 occurs as odorless white crystals or a white crystalline powder.
E 954 has an intensely sweet taste, with a metallic or bitter aftertaste that at normal levels of use can be detected by approximately 25% of the population.
The aftertaste can be masked by blending E 954 with other sweeteners.
E 954 is a crystalline solid with a sweet taste (500 times sweeter than sugar).
Uses
E 954 is a non-nutritive synthetic sweetener which is 300–400 times sweeter than sucrose.
E 954 is nonhygroscopic and has a bitter aftertaste and a stability problem in cooked, canned, or baked goods.
E 954 is slightly soluble in water with a solubility of 10 g in 100 g of water at 25°c, but the solubility improves in boiling water.
As E 954, there are two forms: 1,2-benzisothiazolin-3-one- 1,1-dioxide, sodium salt dihydrate, with a solubility of 1 g in 1.2 ml of water; and 1,2-benzisothiazolin-3-one-1,1-dioxide, sodium salt.
E 954(chemical name: 1,2-benzisothiazolin-3-one-1, 1-dioxide, calcium salt) is used where low sodium content and reduced after-taste are required.
E 954 is used in low-calorie foods such as jam, beverages, and desserts.
E 954 is also termed sodium benzosulfimide.
E 954 is a non-nutritive sweetener; pharmaceutic aid (flavor).
E 954 was formerly listed as reasonably anticipated to be a human carcinogen; delisted because the cancer data are not sufficient to meet the current criteria for this listing.
Usually used in high performance liquid chromatographic method for the simultaneous separation and determination of acesulfame potassium, saccharine and aspartame;and also used in sweet preference test of rats.
In low-calorie and sugar-free food & beverage
Research also has shown that health professionals believe E 954 is especially beneficial to obese individuals and persons with diabetes.
Additionally, research indicates that E 954 may help to reduce the risk of dental caries.
E 954 continues to be important for a wide range of low-calorie and sugar-free food & beverage applications.
E 954 is used in such products as soft drinks, tabletop sweeteners, baked goods, jams, chewing gum, canned fruit, candy, dessert toppings, and salad dressings.
Additionally, personal care products such as toothpaste, mouthwash, hygiene/cosmetic products, vitamins, and pharmaceuticals contain E 954.
Sweeteners blends
The current availability of E 954 and other low-calorie sweeteners, such as aspartame, acesulfame potassium, neotame, and sucralose, allows manufacturers to utilize a “multiple sweetener approach” — using the most appropriate sweetener, or combination of sweeteners, for a given product.
Blending a variety of low-calorie sweeteners provides products with increased stability, improved taste, lower production costs, and more choices for the consumer.
Additionally, blending E 954 with one or more low calorie sweeteners can result in sweetness synergy (the resulting sweetness is greater than the sum of the sweetness of the individual sweeteners), which can decrease the total amount of sweetener.
Sodium Saccharin E 954 is stable when heated, even in the presence of acids, does not react chemically with other food ingredients, and stores well.
In its acidic form, Saccharin E 954 is not particularly water-soluble.
The form used as an artificial sweetener is usually its sodium salt.
People restricting their dietary sodium intake sometimes use calcium salt, E 954.
In toothpaste?
E 954 is a sugar substitute for toothpaste, mouthwash, beverages, table-top sweeteners, confectionery, electro-plating and etc.
From our observing, there is lot of toothpaste that contains E 954.
The use quantity in toothpaste is more than 50% of its total consumption in the market.
E 954 does not promote tooth decay in toothpaste while sugar can.
Toothpaste must have thickeners to stay on the toothbrush and squeeze out of the tube.
E 954 must have detergents to remove fatty films, and water softeners to make the detergents work better, and sweeteners, preferably non-nutritive, so bacteria are not encouraged.
In the feed?
E 954 is intended to be used as a sweetener in feed and water for drinking for piglets, pigs for fattening and veal calves.
The Panel on Additives and Products or Substances used in Animal Feed(FEEDAP) considers the proposed maximum use level of 150 mg/kg feed as safe for calves and pigs for fattening.
For piglets (sucking and weaned piglets), a lower level of 100 mg/kg complete feed is considered safe.
The corresponding maximum safe concentrations in water for drinking are 30 mg/L for piglets and 50 mg/L for pigs for fattening, respectively.
Benefits
Zero glycemic index and beneficial to diabetes
E 954 may be useful for people with diabetes.
E 954 produces no glycemic response and may help control caloric intake.
E954 is both calorie and carbohydrate free.
E 954 is appropriate to use it for medical and nutrition therapy (MNT) for people with diabetes, and dietetic professionals may incorporate saccharin into the individualized meal plans of their patients who have diabetes.
Zero calories
Meanwhile, E 954 produces zero calories and is useful for people trying to control their weight.
E 954 may assist in weight management, control of blood glucose and prevention of dental caries.
Replacing full-calorie products with E 954 may help promote modest weight loss and may facilitate long-term maintenance of weight loss.
E 954 has a long history (more than 100 years) of safe use and contributes no calories to the diet because the human body cannot metabolize it.
(E 954 is excreted in the same form it is ingested.)
Tooth health
E 954 does not contribute to tooth decay.
E 954 is also inexpensive when compared with the second generation artificial sweeteners (aspartame and acesulfame k) and the third generation artificial sweeteners (sucralose).
Heat Stable
E 954 is 500 times sweeter than sucrose.
E 954 has the ability to synergize the sweetening power of both nutritive and nonnutritive sweeteners, and its sweetening power is stable with heating.
These factors make E 954 an excellent food additive in manufactured products.
During such blending of sweeteners, E 954 can provide stability to maintain the product’s sweetness over a prolonged period of time.
E 954 also has a long shelf life.
As a tabletop sweetener, E 954 is available in granular form (mostly 20-40 mesh and 40-80 mesh).
E 954 is useful for consumers who want to create lower-calorie, lower-sugar versions of their favorite recipes.
Because E 954 is heat stable it is a good choice for use in cooking, baking, and canning/preserving.
Depending on the type of recipe, E 954 may be used to replace 50-100 percent of the sugar without sacrificing taste or other aspects of palatability.
Pharmaceutical Applications
E 954 is an intense sweetening agent used in beverages, food products, table-top sweeteners, and oral hygiene products such as toothpastes and mouthwashes.
In oral pharmaceutical formulations, E 954 is used at a concentration of 0.02–0.5% w/w.
E 954 has been used in chewable tablet formulations as a sweetening agent.
E 954 has been used to form various pharmaceutical cocrystals.
E 954 can be used to mask some unpleasant taste characteristics or to enhance flavor systems.
E 954's sweetening power is approximately 300–600 times that of sucrose.
Production Methods
E 954 is prepared from toluene by a series of reactions known as the Remsen–Fahlberg method.
E 954 is first reacted with chlorosulfonic acid to form o-toluenesulfonyl chloride, which is reacted with ammonia to form the sulfonamide.
The methyl group is then oxidized with dichromate, yielding o-sulfamoylbenzoic acid, which forms the cyclic imide saccharin when heated.
An alternative method involves a refined version of the Maumee process.
Methyl anthranilate is initially diazotized to form 2- carbomethoxybenzenediazonium chloride; sulfonation followed by oxidation then yields 2-carbomethoxybenzenesulfonyl chloride.
Amidation of this material, followed by acidification, forms insoluble acid E 954.
Preparation
E 954 is synthesized using two methods: the Remsen-Fahlberg process and the Maumee or Sherwin-Williams method.
The Remsen-Fahlberg synthesis of E 954 starts by reacting toluene with chlorosulfonic acid to give ortho and para forms of toluene-sulfonic acid (Figure 78.1).
The acid can be converted to sulfonyl chlorides by treating with phosphorus pentachloride.
The ortho form, o-toluene-sulfonyl chloride, is treated with ammonia to give o-toluene-sulfonamide, which is then oxidized with potassium permanganate to produce o-sulfamido-benzoic acid.
On heating, the latter yields saccharin.
Another synthesis was developed at Maumee Chemical Company in Toledo, Ohio, and it came to be known as the Maumee process.
This process starts with phthalic anhydride, which is converted into anthranilic acid. Anthranilic acid is then reacted with nitrous acid, sulfur dioxide, chlorine, and ammonia to give saccharin.
The Maumee process was further refi ned by the Sherwin-Williams Company and is therefore now referred to as the Sherwin-Williams process.
Health effects
In the 1970s, studies performed on laboratory rats found an association between consumption of high doses of saccharin and the development of bladder cancer.
However, further study determined that this effect was due to a mechanism that is not relevant to humans (deposition of crystals; see History section).
Epidemiological studies have shown no evidence that E 954 is associated with bladder cancer in humans.
The International Agency for Research on Cancer (IARC) originally classified saccharin in Group 2B ("possibly carcinogenic to humans") based on the rat studies, but downgraded it to Group 3 ("not classifiable as to the carcinogenicity to humans") upon review of the subsequent research.
E 954 has no food energy and no nutritional value.
E 954 is safe to consume for individuals with diabetes or prediabetes.
People with sulfonamide allergies can experience allergic reactions to saccharin, as E 954 is a sulfonamide derivative and can cross-react.
E 954 in toothpaste can cause burning sensations, swelling, and rashes of the mouth and lips in sensitive individuals.
Synonyms
saccharin
81-07-2
o-Benzoic sulfimide
o-Sulfobenzimide
Saccharine
Saccharimide
Benzosulfimide
Benzoic sulfimide
Garantose
o-Benzosulfimide
Benzosulphimide
Saccharinose
Saccharinol
Gluside
Benzosulfinide
Hermesetas
Saccharol
Glucid
Sweeta
Saccharin acid
1,2-Benzisothiazol-3(2H)-one, 1,1-dioxide
Benzoic sulphimide
Saccharin insoluble
1,2-Benzisothiazol-3(2H)-one 1,1-dioxide
Kandiset
Sacarina
Sucrette
Zaharina
Saxin
Sykose
Benzo-2-sulphimide
o-Benzoyl sulfimide
Sucre edulcor
o-Benzoic sulphimide
Benzoylsulfonic Imide
o-Sulfobenzoic acid imide
o-Benzosulphimide
Insoluble saccharin
550 Saccharine
Sacharin
Natreen
o-Benzoyl sulphimide
Anhydro-o-sulfaminebenzoic acid
2,3-Dihydro-3-oxobenzisosulfonazole
2-Sulphobenzoic imide
Benzoic acid sulfimide
Benzo[d]isothiazol-3(2H)-one 1,1-dioxide
1,1-dioxo-1,2-benzothiazol-3-one
1,2-Dihydro-2-ketobenzisosulfonazole
3-Benzisothiazolinone 1,1-dioxide
3-Hydroxybenzisothiazole S,S-dioxide
2,3-Dihydro-3-oxobenzisosulphonazole
1,2-Dihydro-2-ketobenzisosulphonazole
2-Sulfobenzoic acid imide
Rcra waste number U202
Saccharin, insoluble
1,2-Benzisothiazolin-3-one 1,1-dioxide
SACCHARIN SODIUM
3-Hydroxybenzisothiazole-S,S-dioxide
Saccharinum
Syncal
o-Benzoic acid sulfimide
Benzo-sulphinide
Cristallose
Crystallose
Kristallose
Willosetten
Madhurin
Sucromat
Sodium saccharin
Saccharin soluble
Sodium saccharide
Sodium saccharine
Soluble saccharin
1,2-Benzisothiazolin-3-one, 1,1-dioxide
Saccharine soluble
Sodium saccharinate
NSC-5349
FST467XS7D
Saccharin, sodium salt
Sodium o-benzosulfimide
1,1-Dioxide-1,2-benzisothiazolin-3-one
CHEMBL310671
1,1-Dioxo-1,2-benzisothiazol-3(2H)-one
1,2-Benzothiazol-3(2H)-one 1,1-dioxide
INS NO.954(I)
CHEBI:32111
o-Sulfonbenzoic acid imide sodium salt
INS-954(I)
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
E-954(I)
E954
1,1-Dioxo-1,2-dihydro-1lambda*6*-benzo[d]-isothiazol-3-one
Saccharin, soluble
1,2-Benzisothiazoline-3-one 1,1-dioxide
DSSTox_CID_1251
1,1-Dioxide-1,2-benzisothiazol-3(2H)-one
DSSTox_RID_76039
Sacharin [Czech]
DSSTox_GSID_21251
Benzosulfimide, O-
Saccharin [USAN]
Sulfobenzimide, O-
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
Sodium 1,2 benzisothiazolin-3-one 1,1-dioxide
128-44-9
CAS-81-07-2
Saccharin [NF]
NSC4867
NSC5731
LSA
HSDB 669
Tolunene-2-sulfonamide
NSC 5349
NSC 5731
EINECS 201-321-0
RCRA waste no. U202
UNII-FST467XS7D
Glycophenol
Neosaccharin
AI3-38107
SR-01000389315
DTXSID5021251
Benzo-2-sulfiide
O-Benzoylsulfimide
Saccharin nitranion
2-Sulfobenzoicimide
O-Sulfobenzoic imide
Sweeta (TN)
o-sulphobenzoic imide
2-Sulfobenzoic imide
Spectrum_000213
Saccharin, >=98%
Saccharin, >=99%
SACCHARIN [FCC]
SACCHARIN [JAN]
SACCHARIN [II]
SACCHARIN [MI]
SACCHARIN [HSDB]
SACCHARIN [IARC]
SACCHARIN [INCI]
Saccharin (JP15/NF)
Saccharin (JP17/NF)
Spectrum2_001432
Spectrum3_001475
Spectrum4_000449
Spectrum5_001181
SACCHARIN [VANDF]
SACCHARINUM [HPUS]
SACCHARIN [MART.]
WLN: T56 BSWMVJ
EC 201-321-0
SACCHARIN [USP-RS]
SACCHARIN [WHO-DD]
SCHEMBL3816
Saccharin, puriss., 98%
NCIOpen2_005140
NCIOpen2_005180
BSPBio_003029
KBioGR_000838
KBioSS_000693
DivK1c_000164
SPECTRUM1501171
SPBio_001564
GTPL5432
SACCHARIN [EP MONOGRAPH]
BDBM29278
HMS500I06
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
HMS1921N03
HMS2092J09
Pharmakon1600-01501171
BCP29068
HY-Y0272
STR03759
ZINC2560357
3-Benzisothiazolinone 1, 1-dioxide
o-Benzoic sulfimide;o-Sulfobenzimide
Tox21_111358
Tox21_201880
Tox21_302950
BBL015343
CCG-39011
MFCD00005866
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
DB12418
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
FT-0674493
FT-0674494
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
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
W-200289
03AC8EC2-D02A-464C-A7C3-7CABD643CC1E
2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione
BRD-K46493214-001-03-4
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
Mettler-Toledo Calibration substance ME 51143091, Saccharin, traceable to primary standards (LGC)
