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Encyclopedia > Saccharin
Saccharin[1]
IUPAC name 1,1-Dioxo-1,2-benzothiazol-3-one
Other names Benzoic sulfinide
E954
Identifiers
CAS number 81-07-2
PubChem 5143
SMILES C1=CC=C2C(=C1)C(=O)NS2(=O)=O
Properties
Molecular formula C7H5NO3S
Molar mass 183.1845
Appearance White crystalline solid
Density 0.828 g/cm3
Melting point

228.8-229.7 °C Image File history File links Download high-resolution version (1081x1100, 51 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Saccharin ... Image File history File links Download high-resolution version (1100x958, 190 KB) File links The following pages on the English Wikipedia link to this file (pages on other projects are not listed): Saccharin ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... PubChem is a database of chemical molecules. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... A chemical formula is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... For other uses, see Density (disambiguation). ... The melting point of a crystalline solid is the temperature range at which it changes state from solid to liquid. ...

Solubility in water 1 g per 290 mL
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Saccharin[2] is the oldest artificial sweetener. The basic substance, benzoic sulfinide, was produced in 1878 by Constantin Fahlberg, a chemist working on coal tar derivatives in Ira Remsen's laboratory at the Johns Hopkins University, and it was he who, accidentally, discovered its intensely sweet nature. 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." Solubility is a chemical property referring to the ability for a given substance, the solute, to dissolve in a solvent. ... Impact from a water drop causes an upward rebound jet surrounded by circular capillary waves. ... The plimsoll symbol as used in shipping In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals exactly). ... A sweetener is a food additive which adds the basic taste of sweetness to a food. ... Constatin Fahlberg is most known for, along with Ira Remsen, discovering the artificial sweetener, saccharin, in 1979 at Johns Hopkins University. ... Ira Remsen (February 10, 1846 - March 4, 1927) was a chemist who, along with Constantin Fahlberg discovered the artificial sweetener saccharin. ... The Johns Hopkins University, founded in 1876, is a private institution of higher learning located in Baltimore, Maryland, United States. ...


In the European Union, saccharin is also known under the E number (additive code) E954. For the mathematical constant see: E (mathematical constant). ...


Saccharin is about 300 times as sweet as sucrose, but has an unpleasant bitter or metallic aftertaste, especially at high concentrations. Unlike the newer artificial sweetener aspartame, saccharin is stable when heated, even in the presence of acids, does not react chemically with other food ingredients, and stores well. Blends of saccharin with other sweeteners are often used to compensate for each sweetener's weaknesses. 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 was an important discovery, especially for diabetics, as it goes directly through the human digestive system without being digested. It does not affect blood insulin levels, and has effectively no food energy. Flash point N/A Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Sucrose (common name: table sugar, also called saccharose) is a disaccharide (glucose + fructose) with the molecular formula C12H22O11. ... Aftertaste is the persistence of a sensation of flavor after the stimulating substance has passed out of contact with the sensory end organs for taste. ... Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Aspartame (or APM) (IPA: ) is the name for an artificial, non-saccharide sweetener, aspartyl-phenylalanine-1-methyl ester; i. ... Cyclamate is an artificial sweetener that was discovered in 1937 at the University of Illinois by graduate student Michael Sveda. ... For the disease characterized by excretion of large amounts of very dilute urine, see diabetes insipidus. ... what was here was sick and improperly spelled. ... Not to be confused with inulin. ... Food energy is the amount of energy in food that is available through digestion. ...


In its acidic form, saccharin is not particularly 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.[3][4] For sodium in the diet, see Edible salt. ... This article is about common table salt. ... For other uses, see Calcium (disambiguation). ...

Contents

Saccharin and the US Government

Starting in 1907, the USDA began investigating saccharin. Problems with saccharin and the USDA have not been resolved since then. The initial series of investigations begun by the USDA in 1907 were a direct result of the Pure Food and Drug Act. The act, passed in 1906, came after a storm of health controversies surry influenced the American public, bringing to light many of the health issues surrounding the meat-packing industry. The U.S. Department of Agriculture, also called the Agriculture Department, or USDA, is a Cabinet department of the United States Federal Government. ...


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. This opinion clashed strongly with President Theodore Roosevelt who rejected the notion that saccharin was dangerous, stating, "Anybody who says saccharin is injurious is an idiot." Wiley first battled saccharin in 1908. 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. In 1969, files were discovered from the Food and Drug Administration investigations from 1948 and 1949 and this stirred more controversy. 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 from being used in anything.[5] b Harvey Washington Wiley Harvey Washington Wiley (October 30, 1844, Kent, Indiana - June 30, 1930, Washington, D.C.) was a noted chemist involved with the passage of the landmark Pure Food and Drug Act of 1906. ... Theodore Roosevelt, Jr. ...


History

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 being the Coca-Cola Company's cola drink Tab, introduced in 1963 as a diet cola soft drink. “The Great War ” redirects here. ... The 1960s decade refers to the years from 1960 to 1969. ... The 1970s decade refers to the years from 1970 to 1979, also called The Seventies. ... Etymology: French calorie, from Latin calor (heat), from calere (to be warm). ... This article is about the color. ... SweetN Low is a popular brand of artificial sweetener made from granulated saccharin and dextrose. ... A soft drink is a drink that contains no alcohol. ... The wave shape (known as the dynamic ribbon device) present on all Coca-Cola cans throughout the world derives from the contour of the original Coca-Cola bottles. ... TaB is a diet cola. ... For other uses, see 1963 (disambiguation). ...


Chemistry

The image to the right shows the chemical structure of saccharin. It has the chemical formula C7H5NO3S.


Saccharin can be produced in various ways.[6] Remsen & Fahlberg's 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.[7] Toluene, also known as methylbenzene or phenylmethane is a clear, water-insoluble liquid with the typical smell of paint thinners, redolent of the sweet smell of the related compound benzene. ... Year 1950 (MCML) was a common year starting on Sunday (link will display the full calendar) of the Gregorian calendar. ... Nickname: Location in the state of Ohio Coordinates: , Country United States State Ohio County Lucas Founded 1833 Government  - Mayor Carty Finkbeiner (D) Area  - City 84. ... Anthranilic acid has the formula C7H7NO2[1] and is an odorless white to yellow crystalline acid, which is freely soluble in water. ... Nitrous acid (molecular formula HNO2) is a weak monobasic acid known only in solution and in the form of nitrite salts. ... Sulfur dioxide (or Sulphur dioxide) has the chemical formula SO2. ... General Name, symbol, number chlorine, Cl, 17 Chemical series halogens Group, period, block 17, 3, p Appearance yellowish green Standard atomic weight 35. ... For other uses, see Ammonia (disambiguation). ... Benzyl chloride, or α-chlorotoluene, is an organic compound consisting of a benzene ring substituted with a chloromethyl group. ...


Saccharin is an acid with a pKa of about 2.[8][9] The acid dissociation constant (Ka), also known as the acidity constant or the acid-ionization constant, is a specific equilibrium constant for the reaction of an acid with its conjugate base in aqueous solution [1]. // When an acid dissolves in water, it partly dissociates forming hydronium ions and its conjugate...


Saccharin and cancer

Saccharin warning on a diet soda can.
Old Sweet 'n Low packet with cancer warning printed on the back

There have been worries about the safety of saccharin since its introduction. As early as 1907 saccharin came under the examination and scrutiny of the United States Department of Agriculture (USDA). As Theodore Roosevelt took the office of the President of the United States, an intense debate questioned the safety of the artificial sweetener. Sparked by the Pure Food and Drug Act of 1906, saccharin was investigated by the "poison squad," led by Harvey W. Wiley's assertion that it caused digestive problems (Kauffman and Priebe pg 557). Commenting on the questionable safety of saccharin, Theodore Roosevelt (who was at the time dieting on orders from his physician to lower his risk for diabetes) once said directly to Wiley, "Anyone who thinks saccharin is dangerous is an idiot". The controversy continued with the prohibition of saccharin during the Taft administration. Studies and legal controversy fueled the heated debate of this prohibition until the outbreak of the first World War. During World War I, the United States experienced a sugar shortage; the prohibition of saccharin was lifted to balance the demand for sugar. The wide spread production and use of saccharin continued through World War II, again alleviating the shortages during war time but immediately slowing at the war's end.[10] ImageMetadata File history File links Download high resolution version (2985x1042, 350 KB) Picture of saccharin warning on a diet Dr Pepper can. ... ImageMetadata File history File links Download high resolution version (2985x1042, 350 KB) Picture of saccharin warning on a diet Dr Pepper can. ... Image File history File links Sweetnlow. ... Image File history File links Sweetnlow. ... USDA redirects here. ... Theodore Roosevelt, Jr. ... Federal courts Supreme Court Circuit Courts of Appeal District Courts Elections Presidential elections Midterm elections Political Parties Democratic Republican Third parties State & Local government Governors Legislatures (List) State Courts Local Government Other countries Atlas  US Government Portal      For other uses, see President of the United States (disambiguation). ... Categories: Law stubs | United States law ... Harvey Washington Wiley Harvey Washington Wiley (October 30, 1844, Kent, Indiana - June 30, 1930, Washington, D.C.) was a noted chemist involved with the passage of the landmark Pure Food and Drug Act of 1906. ... For other uses, see Idiot (disambiguation). ...


Throughout the 1960s, various studies suggested that saccharin might be an animal carcinogen. Concern peaked in 1977, after the publication of a study indicating an increased rate of bladder cancer in rats fed large doses of saccharin. In that year, Canada banned saccharin while the United States Food and Drug Administration also proposed a ban. At the time, saccharin was the only artificial sweetener available in the U.S., and the proposed ban met with strong public opposition, especially among diabetics. Eventually, the U.S. Congress placed a moratorium on the ban, requiring instead that all saccharin-containing foods display a warning label indicating that saccharin may be a carcinogen. Year 1960 (MCMLX) was a leap year starting on Friday (link will display full calendar) of the Gregorian calendar. ... Look up carcinogen in Wiktionary, the free dictionary. ... Also: 1977 (album) by Ash. ... This article is about the urinary bladder. ... Cancer is a class of diseases or disorders characterized by uncontrolled division of cells and the ability of these to spread, either by direct growth into adjacent tissue through invasion, or by implantation into distant sites by metastasis (where cancer cells are transported through the bloodstream or lymphatic system). ... Species 50 species; see text *Several subfamilies of Muroids include animals called rats. ... “FDA” redirects here. ... This article is about the disease that features high blood sugar. ... The Congress of the United States is the legislative branch of the federal government of the United States of America. ...


Many studies have since been performed on saccharin, some showing a correlation between saccharin consumption and increased frequency of cancer (especially bladder cancer) and others finding no such correlation. No study has ever shown a clear causal relationship between saccharin consumption and health risks in humans at normal doses, though some studies have shown a correlation between consumption and cancer incidence.[11] Furthermore, the biological mechanism believed to be responsible for the rat cancers has been shown to be inapplicable to humans because of differences in urine composition between rats and humans. Many of the rat cancers may have been caused by contamination from the rubber plungers inside syringes[12]., the rubber seals used may corrode when mixed with certain fluids and the decomposed rubber may have caused the bad results[13]. Others blame certain types of rats like the Fischer 344 Rat which became a poor example specimen for testing cancers when it was found out that these laboratory animals developed cancer spontaneously, when injected with pure water only.[14]


According to tradegroup operated saccharin.org, "Concerns over saccharin's safety were first raised twenty years ago after a flawed study that administered huge quantities of the sweetener to laboratory rats produced bladder tumors in rats. New and better scientific research has decisively shown that the earlier rat studies are not at all applicable to humans."


In 1991, after fourteen years, the FDA formally withdrew its 1977 proposal to ban the use of saccharin, and in 2000, the U.S. Congress repealed the law requiring saccharin products to carry health warning labels. Year 1991 (MCMXCI) was a common year starting on Tuesday (link will display the 1991 Gregorian calendar). ... Year 2000 (MM) was a leap year starting on Saturday (link will display full 2000 Gregorian calendar). ...


See also

Sucralose is an artificial sweetener. ... Except where noted otherwise, data are given for materials in their standard state (at 25 Â°C, 100 kPa) Infobox disclaimer and references Aspartame (or APM) (IPA: ) is the name for an artificial, non-saccharide sweetener, aspartyl-phenylalanine-1-methyl ester; i. ... EQUAL is a popular brand of artificial sweetener made mainly from aspartame. ... NutraSweet is the company that makes and sells aspartame, an artificial sugar substitute. ... CANDEREL is a popular brand of artificial sweetener made mainly from aspartame. ... Chemical structure of neotame. ...

Notes and references

  1. ^ Merck Index, 11th Edition, 8282.
  2. ^ 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]
  3. ^ Remsen, I. and Fahlberg, C., (1879). "Über die Oxydation des Orthotoluolsulfamids". Chemische Berichte 12: 469-473. 
  4. ^ 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: 556-574. doi:10.1007/BF01096124. 
  5. ^ Preibe and Kauffman, 2,3,4,6,7
  6. ^ 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. 
  7. ^ Bungard, 1967
  8. ^ WHO food additives series 17
  9. ^ pKa data compiled by R. Williams
  10. ^ Kauffman and Priebe pg 559-60
  11. ^ Weihrauch M. R., Diehl V. (2004). "Artificial sweeteners - do they bear a carcinogenic risk?". Annals of Oncology 15 (10): 1460-1465. doi:10.1093/annonc/mdh256. 
  12. ^ Is Saccharin Safe? .: Ask. Dr. Hull
  13. ^ Is Saccharin Safe? .: Ask. Dr. Hull
  14. ^ Saccharin and Its Salts, International Agency for Research on Cancer
  • Paul M. Priebe and George B. Kauffman, “Making Government Policy under Conditions of Scientific Uncertainty: a Century of Controversy about Saccharin in Congress and the Laboratory,” Minerva, 18, 1980, 556-74.

External links


  Results from FactBites:
 
Saccharin - Wikipedia, the free encyclopedia (876 words)
Saccharin is the oldest artificial sweetener; it was discovered in 1879 by Ira Remsen and Constantin Fahlberg of Johns Hopkins University.
Saccharin is about 300 times as sweet as sucrose, but has an unpleasant bitter or metallic aftertaste, especially at high concentrations.
Saccharin's sweetness was accidentally discovered by Ira Remsen, a professor at Johns Hopkins University, and Constantin Fahlberg, a research fellow working in Remsen's lab.
791. Saccharin and its salts (WHO Food Additives Series 32) (10988 words)
SACCHARIN AND ITS SALTS First draft prepared by Ms E. Vavasour Toxicological Evaluation Division Bureau of Chemical Safety, Food Directorate Health and Welfare Canada Ottawa, Ontario, Canada 1 EXPLANATION Saccharin was evaluated by the Committee at its eleventh, eighteenth, twenty-first, twenty-fourth, twenty-sixth and twenty-eighth meetings (Annex 1, references 14, 35, 44, 53, 59, and 66).
Measurement of the extent of faecal excretion of orally administered saccharin indicated that gastrointestinal absorption was incomplete and variable in the rat, with the percentage of the administered dose recovered in the faeces ranging from 3-39% (Renwick 1985).
The Committee concluded from the long-term feeding studies that the dose-related carcinogenic activity of sodium saccharin on the urinary bladder was specific to the male rat and that exposure during the neonatal period was critical for the subsequent development of these tumours in the absence of an initiator or stimulus such as freeze ulceration.
  More results at FactBites »


 

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