Saccharin
| Saccharin[1] | |
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1,1-Dioxo-1,2-benzothiazol-3-one
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Other names
Benzoic sulfimide
E954 |
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| Identifiers | |
| CAS number | 81-07-2  |
| PubChem | 5143 |
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SMILES
C1=CC=C2C(=C1)C(=O)NS2(=O)=O
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| Properties | |
| Molecular formula | C7H5NO3S |
| Molar mass | 183.18 g mol−1 |
| Appearance | White crystalline solid |
| Density | 0.828 g/cm3 |
| Melting point |
228.8-229.7 °C |
| Solubility in water | 1 g per 290 mL |
| (what is this?) (verify) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) |
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| Infobox references | |
Saccharin[2] is an artificial sweetener. The basic substance, benzoic sulfimide, has effectively no food energy and is much sweeter than sucrose, but has an unpleasant bitter or metallic aftertaste, especially at high concentrations. It is used to sweeten products such as drinks, candies, medicines, and toothpaste.
Contents |
Properties
Saccharin is unstable when heated but it does not react chemically with other food ingredients. As such, it stores well. Blends of saccharin with other sweeteners are often used to compensate for each sweetener's weaknesses and faults. A 10:1 cyclamate:saccharin blend is common in countries where both these sweeteners are legal; in this blend, each sweetener masks the other's off-taste. Saccharin is often used together with aspartame in diet soda, so that some sweetness remains should the fountain syrup be stored beyond aspartame's relatively short shelf life. Saccharin is believed to be an important discovery, especially for diabetics, as it goes directly through the human digestive system without being digested. Although saccharin has no food energy, it can trigger the release of insulin in humans and rats, apparently as a result of its taste,[3] [4][5] as can other sweeteners like aspartame.[6]
In its acid form, saccharin is not water-soluble. The form used as an artificial sweetener is usually its 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 grams per milliliter water at room temperature.[7][8]
History
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. 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."
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".
Saccharin was delisted by the Office of Environmental Health Hazard Assessment (OEHHA) of the California Environmental Protection Agency from the list of chemicals known to the state to cause cancer on April 6, 2001.[9] It had been added to the list in 1989.
Chemistry
Saccharin has the chemical formula C7H5NO3S and it can be produced in various ways.[10] 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.[11]
Saccharin is an acid with a pKa of about 2.[12][13]
Saccharin can be used to prepare exclusively disubstituted amines from alkyl halides via a Gabriel synthesis.[14]
Government regulation
Starting in 1907, the USDA began investigating saccharin as a direct result of the Pure Food and Drug Act. Harvey Wiley, then the director of the bureau of chemistry for the USDA, viewed it as both an illegal substitution of a valuable ingredient (sugar) by a less valuable ingredient. In a clash that had career consequences, Wiley told then President Theodore Roosevelt 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." But Roosevelt himself was a consumer of saccharin, and in a heated exchange, Roosevelt angrily answered Wiley by stating, "Anybody who says saccharin is injurious to health is an idiot."[15] The episode proved the undoing of Wiley's career.
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.
More controversy was stirred in 1969 with the discovery of files from the FDA'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.[16] However, this attempt was also unsuccessful and the sweetener is widely used in the United States; it is the third-most popular after sucralose and aspartame.
In the European Union saccharin is also known by the E number (additive code) E954.
The current status of saccharin is that it is not banned anywhere in the world and there are no moves to ban it. The concerns that is is associated with bladder cancer were proved to be without foundation in experiments on primates.[17]
Unfounded cancer concerns
Studies in laboratory rats during the early 1970s linked saccharin with the development of bladder cancer, resulting in the United States Congress mandating that all food containing saccharin bear a warning label.
In 2000, the warning labels disappeared because scientists learned that rats have a unique combination of high pH, high calcium phosphate, and high protein levels in their urine.[18][19] One or more of the proteins that is more prevalent in male rats combines with calcium phosphate and saccharin to produce microcrystals that damage the lining of the bladder. Over time, the rat's bladder responds to this damage by over-producing cells to repair the damage, and this leads to tumor formation. This does not occur in humans, so there is no bladder cancer risk.
The delisting of saccharin led to legislation, which was signed into law on December 21, 2000, repealing the warning label requirement for products containing saccharin.
See also
- Cyclamate
- Sucralose (Splenda)
- Aspartame (Equal, NutraSweet, and Canderel)
- Neotame
- Steviol glycoside
- Gilda Live (featuring the song "Goodbye Saccharin", a well-known parody of the substance's link to cancer)
Notes and references
- ↑ Merck Index, 11th Edition, 8282.
- ↑ The word saccharin (as above) has no final "e". The word saccharine, with a final "e", is much older and is an adjective meaning "sugary" – its connection with sugar means the term is used metaphorically, often in a derogative sense, to describe something "unpleasantly over-polite" or "overly sweet".[1] Both words are derived from the Greek word σάκχαρον (sakcharon, German "ch" sound), which ultimately derives from Sanskrit for sugar, sharkara (शर्करा), which literally means "gravel" [2]
- ↑ Just T, Pau HW, Engel U, Hummel T (November 10, 2008). "Cephalic phase insulin release in healthy humans after taste stimulation?". Appetite 238 (4): 622–7. doi:10.1016/j.appet.2008.04.271. PMID 18556090. http://www.ncbi.nlm.nih.gov/pubmed/18556090.
- ↑ E Ionescu, F Rohner-Jeanrenaud, J Proietto, RW Rivest and B Jeanrenaud (1988). "Taste-induced changes in plasma insulin and glucose turnover in lean and genetically obese rats". Diabetes 37 (6): 773–779. doi:10.2337/diabetes.37.6.773. PMID 3289998.
- ↑ H. R. Berthoud, E. R. Trimble, E. G. Siegel, D. A. Bereiter and B. Jeanrenaud (April 1, 1980). "Cephalic-phase insulin secretion in normal and pancreatic islet-transplanted rats". American Journal of Physiology-Endocrinology and Metabolism 238 (4): E336=E340. PMID 6769337. http://ajpendo.physiology.org/cgi/content/abstract/238/4/E336.
- ↑ "Is Aspartame Really Safer in Reducing the Risk of Hypoglycemia During Exercise in Patients With Type 2 Diabetes? — Diabetes Care". care.diabetesjournals.org. http://care.diabetesjournals.org/content/30/7/e59.long. Retrieved 2010-06-20.
- ↑ Remsen, I. and Fahlberg, C., (1879). "Über die Oxydation des Orthotoluolsulfamids". Chemische Berichte 12: 469–473. http://gallica.bnf.fr/ark:/12148/bpt6k90688q/f519.chemindefer.
- ↑ P. M. Priebem, G. B. Kauffman (1980). "Making governmental policy under conditions of scientific uncertainty: A century of controversy about saccharin in congress and the laboratory". Minerva 18 (4): 556–574. doi:10.1007/BF01096124. PMID 11611011.
- ↑ http://oehha.ca.gov/prop65/prop65_list/files/P65single121809.pdf
- ↑ David J. Ager, David P. Pantaleone, Scott A. Henderson, Alan R. Katritzky, Indra Prakash, D. Eric Walters (1998). "Commercial, Synthetic Nonnutritive Sweeteners". Angewandte Chemie International Edition 37 (13-24): 1802–1817 ele=afficheN&cpsidt=10528065. doi:10.1002/(SICI)1521-3773(19980803)37:13/14<1802::AID-ANIE1802>3.0.CO;2-9.
- ↑ Bungard, 1967
- ↑ WHO food additives series 17
- ↑ pKa data compiled by R. Williams
- ↑ Sugasawa, S.; Abe, K. J. Pharm. Soc. Jpn. 1952, 72, 270; Chem Abstr, 1953, 47, 1626c
- ↑ "Sugar: A Cautionary Tale". www.fda.gov. http://www.fda.gov/AboutFDA/WhatWeDo/History/ProductRegulation/SelectionsFromFDLIUpdateSeriesonFDAHistory/ucm091680.htm. Retrieved 2010-06-20.
- ↑ Preibe and Kauffman, 2,3,4,6,7
- ↑ Takayama, S.; Sieber, SM.; Adamson, RH.; Thorgeirsson, UP.; Dalgard, DW.; Arnold, LL.; Cano, M.; Eklund, S. et al. (Jan 1998). "Long-term feeding of sodium saccharin to nonhuman primates: implications for urinary tract cancer.". J Natl Cancer Inst 90 (1): 19-25. PMID 9428778.
- ↑ Whysner, J.; Williams, GM. (1996). "Saccharin mechanistic data and risk assessment: urine composition, enhanced cell proliferation, and tumor promotion.". Pharmacol Ther 71 (1-2): 225-52. PMID 8910956.
- ↑ Dybing, E. (Dec 2002). "Development and implementation of the IPCS conceptual framework for evaluating mode of action of chemical carcinogens.". Toxicology 181-182: 121-5. PMID 12505296.
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