Sodium cyclamate

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Sodium cyclamate
Cyclamate Structural Formulae .V.1.svg
Names
IUPAC name
sodium N-cyclohexylsulfamate
Identifiers
139-05-9 YesY
ChEMBL ChEMBL273977 YesY
ChemSpider 8421 YesY
Jmol-3D images Image
PubChem 8751
UNII 1I6F42RME1 N
Properties
C6H12NNaO3S
Molar mass 201.22 g·mol−1
Hazards
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oil Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 N verify (what isYesY/N?)
Infobox references

Sodium cyclamate (sweetener code 952) is an artificial sweetener. It is 30–50 times sweeter than sucrose (table sugar), making it the least potent of the commercially used artificial sweeteners. It is often used with other artificial sweeteners, especially saccharin; the mixture of 10 parts cyclamate to 1 part saccharin is common and masks the off-tastes of both sweeteners.[1] It is less expensive than most sweeteners, including sucralose, and is stable under heating.

Chemistry[edit]

Cyclamate is the sodium or calcium salt of cyclamic acid (cyclohexanesulfamic acid), which itself is prepared by the sulfonation of cyclohexylamine. This can be accomplished by reacting cyclohexylamine with either sulfamic acid or sulfur trioxide.[2]

History[edit]

Funny Face drink mix packet from 1970-71 advertising "No Cyclamate - Just Add Sugar"

Cyclamate was discovered in 1937 at the University of Illinois by graduate student Michael Sveda. Sveda was working in the lab on the synthesis of anti-fever medication. He put his cigarette down on the lab bench, and, when he put it back in his mouth, he discovered the sweet taste of cyclamate.[3][4]

The patent for cyclamate was purchased by DuPont but later sold to Abbott Laboratories, which undertook the necessary studies and submitted a New Drug Application in 1950. Abbott intended to use cyclamate to mask the bitterness of certain drugs such as antibiotics and pentobarbital. In the United States in 1958, it was designated GRAS (Generally Recognized as Safe). Cyclamate was marketed in tablet form for use by diabetics as an alternative tabletop sweetener, as well as in a liquid form. As cyclamate is stable to heat, it was and is marketed as suitable for use in cooking and baking.

Controversy developed when, in 1966, a study reported that some intestinal bacteria could desulfonate cyclamate to produce cyclohexylamine, a compound suspected to have some chronic toxicity in animals. Further research resulted in a 1969 study that found the common 10:1 cyclamate:saccharin mixture to increase the incidence of bladder cancer in rats. The released study was showing that eight out of 240 rats fed a mixture of saccharin and cyclamates, at levels of humans ingesting 350 cans of diet soda per day, developed bladder tumors.[5]

Sales continue to expand, and in 1969 there were $1 billion in annual sales of cyclamate, which increased pressure from public safety watchdogs to restrict the use of cyclamate. In October 1969, Department of Health, Education & Welfare Secretary Robert Finch bypassed the Commissioner Herbert L. Ley, Jr. of the Food and Drug Administration and removed the GRAS designation from cyclamate and banned its use in general purpose foods, though it remained available for restricted use in dietary products with additional labeling; in October 1970 the Food and Drug Administration under a new FDA commisssioner banned cyclamate completely from all food and drug products in the United States.[6]

Abbott Laboratories claimed that its own studies were unable to reproduce the 1969 study's results, and, in 1973, Abbott petitioned the FDA to lift the ban on cyclamate. This petition was eventually denied in 1980 by FDA Commissioner Jere Goyan.[7] Abbott Labs, together with the Calorie Control Council (a political lobby representing the diet foods industry), filed a second petition in 1982. Although the FDA has stated that a review of all available evidence does not implicate cyclamate as a carcinogen in mice or rats,[8] cyclamate remains banned from food products in the United States. The petition is now held in abeyance, though not actively considered.[9] It is unclear whether this is at the request of Abbott Labs or because the petition is considered to be insufficient by the FDA.

Health[edit]

In 1969 an Abbott Laboratories study involving a 10:1 mixture of cyclamate and saccharin indicated that large amounts of cyclamates fed to rats over prolonged periods of time caused bladder cancer in the test rats.[6] Another 1978 study "concluded that neither saccharin nor cyclamate is likely to be carcinogenic in man."[10] Other studies implicated cyclohexylamine in testicular atrophy in mice.[11][12]

A 2003 paper reports the first epidemiological study designed to investigate the possibility of a relationship between cyclamate and cyclohexylamine and male fertility in humans. It states that "the results demonstrate no effect of cyclamate or cyclohexylamine on male fertility at the present levels of cyclamate consumption."[13]

Incidents[edit]

In Taipei, Taiwan, a city health survey in 2010 found nearly 30% of tested dried fruit products failed a health standards test, most having excessive amounts of cyclamate, some at levels 20 times higher than the legal limit.[14]

Legal status[edit]

Cyclamate is approved as a sweetener in over 55 countries.[15]

In the late 1960s cyclamate was banned in the United Kingdom but was approved after being re-evaluated by the European Union in 1996.[16]

In the Philippines cyclamate was once banned, however in 2013 the Philippine Food and Drug Administration lifted the ban and it was declared safe for Philippine consumption.[17][18]

Cyclamate is currently banned in the United States.[19][20][21]

Brands[edit]

Sweeteners produced by Sweet'N Low and Sugar Twin[22] for Canada contain cyclamate, though not those produced for the United States.

  • Assugrin (Switzerland, Brazil)[23]
  • Chuker (Argentina) - Merisant Company 2, SARL
  • Cologran
  • Hermesetas
  • Huxol (Germany) in liquid form
  • Novasweet (Russia)[24]
  • Rio (Produced under license and authority of SweetLife AG Switzerland by SweetLife Ltd, China)
  • Sucaryl[25]
  • Sugar Twin (Canada)[26]
  • Suitli (Bulgaria)
  • Sweet N' Low (Canada)

Notes and references[edit]

  1. ^ Jim Smith, Lily Hong-Shum (Apr 15, 2008). Food Additives Data Book. John Wiley & Sons. p. 960. ISBN 9781405172417. 
  2. ^ McKetta Jr, John J. (Jun 19, 1996). "Sweeteners, High Intensity". Encyclopedia of Chemical Processing and Design 56: 72. ISBN 9780824726072. 
  3. ^ Packard, Vernal S. (1976). Processed foods and the consumer: additives, labeling, standards, and nutrition. Minneapolis: University of Minnesota Press. p. 332. ISBN 0-8166-0778-8. 
  4. ^ Michael Sveda, the Inventor Of Cyclamates, Dies at 87 - New York Times
  5. ^ "Not all are convinced by sweet science". 
  6. ^ a b Chedd, Grahm (May 9, 1974). "The Search for Sweetness". New Scientist 62 (897): 299. 
  7. ^ Goyan, Jere E.,Commissioner of Food and Drugs. (4 September 1980). "Cyclamate, Commissioner's Decision, 45 FR 61474" (PDF). Office of the Federal Register. pp. 61474–61530. Retrieved February 8, 2015. [...] approval of cyclamate for use as a sweetening agent in food and for technological purposes in food is denied. 
  8. ^ "FDA Talk Paper, NAS Report on Cyclamate" (PDF). 
  9. ^ "Petitions Currently Held in Abeyance". Retrieved February 8, 2015. FAP 2A3672 Cyclamate (cyclamic acid, calcium cyclamate, and sodium cyclamate) 
  10. ^ Kessler, Irving I.; Clark, J. P. (1978). "Saccharin, Cyclamate, and Human Bladder Cancer". JAMA 240 (4): 349–55. doi:10.1001/jama.1978.03290040027017. PMID 660869. 
  11. ^ "SUMMARY OF TOXICOLOGICAL DATA OF CERTAIN FOOD ADDITIVES". 
  12. ^ Roberts, A.; Renwick, A.G.; Ford, G.; Creasy, D.M.; Gaunt, I. (1989). "The metabolism and testicular toxicity of cyclohexylamine in rats and mice during chronic dietary administration". Toxicology and Applied Pharmacology 98 (2): 216–29. doi:10.1016/0041-008X(89)90227-5. PMID 2711388. 
  13. ^ Serra-Majem, L.; Bassas, L.; Garcia-Glosas, R.; Ribas, L.; Ingles, C.; Casals, I.; Saavedra, P.; Renwick, A. G. (2003). "Cyclamate intake and cyclohexylamine excretion are not related to male fertility in humans". Food Additives & Contaminants: Part A 20 (12): 1097–104. doi:10.1080/02652030310001620450. PMID 14726272. 
  14. ^ Jian Chen and Y.L. Kao (18 January 2010). "Nearly 30% dried, pickled foods fail safety inspections". The China Post. Retrieved 1 November 2010. 
  15. ^ http://www.cyclamate.org/pdf/Cyclamate_worldwidestatus.pdf
  16. ^ Ashurst, Philip R. (Apr 15, 2008). Chemistry and Technology of Soft Drinks and Fruit Juices. John Wiley & Sons. p. 247. 
  17. ^ http://www.chd11.doh.gov.ph/webfiles/pdf/pubadv/20060130-neotogen.pdf
  18. ^ FDA lifts ban on ‘magic sugar’ | Metro, News, The Philippine Star
  19. ^ "High-Intensity Sweeteners". U.S. Food and Drug Administration. 19 May 2014. Retrieved 8 February 2015. Are there any high-intensity sweeteners that are currently prohibited by FDA for use in the United States but are used in other countries? Yes. Cyclamates and its salts (such as calcium cyclamate, sodium cyclamate, magnesium cyclamate, and potassium cyclamate) are currently prohibited from use in the United States. 
  20. ^ "Everything Added to Food in the United States (EAFUS), Search Criteria = "cyclamate"". U.S. Food and Drug Administration. Retrieved 8 February 2015. 
  21. ^ Newton, David E (2009-01-01). Food Chemistry. pp. 73–77. ISBN 9781438109756. 
  22. ^ "Tastes like sugar". Retrieved 1 November 2010. 
  23. ^ Assugrin's website (French)
  24. ^ НоваПродукт
  25. ^ "Sucaryl". 
  26. ^ Sugar Twin Artificial Sweetener (Canada)

External links[edit]