Cyclamate

Last updated

Contents

Cyclamate
(Sodium cyclamate)
Cyclamate Structural Formulae .V.1.svg
Names
Preferred IUPAC name
Sodium cyclohexylsulfamate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.863 OOjs UI icon edit-ltr-progressive.svg
E number E952(iv) (glazing agents, ...)
PubChem CID
UNII
  • InChI=1S/C6H13NO3S.Na/c8-11(9,10)7-6-4-2-1-3-5-6;/h6-7H,1-5H2,(H,8,9,10);/q;+1/p-1 Yes check.svgY
    Key: UDIPTWFVPPPURJ-UHFFFAOYSA-M Yes check.svgY
  • InChI=1/C6H13NO3S.Na/c8-11(9,10)7-6-4-2-1-3-5-6;/h6-7H,1-5H2,(H,8,9,10);/q;+1/p-1
    Key: UDIPTWFVPPPURJ-REWHXWOFAV
  • [Na+].O=S([O-])(=O)NC1CCCCC1
Properties
C6H12NNaO3S
Molar mass 201.22 g·mol−1
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Cyclamate 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. Safety concerns led to it being banned in a few countries, though the European Union considers it safe.

Chemistry

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

Prior to 1973, Abbott Laboratories produced sodium cyclamate (Sucaryl) by a mixture of ingredients including the addition of pure sodium (flakes or rods suspended in solvent) with cyclohexylamine, chilled and filtered through a high speed centrifugal separator, dried, granulated and micro-pulverised for powder or tablet usage.[ citation needed ]

History

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 an antipyretic drug. 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 and 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 1958, it was designated GRAS (Generally Recognized as Safe) by the United States Food and Drug Administration. 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.[ citation needed ]

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 increased 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 equivalent to humans ingesting 550 cans of diet soda per day, developed bladder tumors. [5]

Sales continued to expand, and in 1969, annual sales of cyclamate had reached $1 billion, which increased pressure from public safety watchdogs to restrict the usage of cyclamate. In October 1969, Department of Health, Education & Welfare Secretary Robert Finch, bypassing Food and Drug Administration Commissioner Herbert L. Ley, Jr., 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 FDA, under a new commissioner, 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.

In 2000, a paper was published describing the results of a 24-year-long experiment in which 16 monkeys were fed a normal diet and 21 monkeys were fed either 100 or 500 mg/kg cyclamate per day; the higher dose corresponds to about 30 cans of a diet beverage. Two of the high-dosed monkeys and one of the lower-dosed monkeys were found to have malignant cancer, each with a different kind of cancer, and three benign tumors were found. The authors concluded that the study failed to demonstrate that cyclamate was carcinogenic because the cancers were all different and there was no way to link cyclamate to each of them. [10] The substance did not show any DNA-damaging properties in DNA repair assays. [10]

Cyclamate is approved as a sweetener in at least 130 countries. [11] In the late 1960s, cyclamate was banned in the United Kingdom; however, it was approved after being re-evaluated by the European Union in 1996. [12]

In the Philippines, cyclamate was banned until the Philippine Food and Drug Administration lifted the ban in 2013, declaring it safe for consumption. [13] Cyclamate remains banned in the United States and South Korea. [14] [15] [16] [17]

Brands

Sweeteners produced by Sweet'n Low and Sugar Twin [18] for Canada contain cyclamate, though not those produced for the United States.

Notes and references

  1. Jim Smith, Lily Hong-Shum (April 15, 2008). Food Additives Data Book. John Wiley & Sons. p. 960. ISBN   9781405172417.
  2. McKetta Jr, John J. (June 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. pp.  332. ISBN   0-8166-0778-8.
  4. Kaufman, Leslie (August 21, 1999). "Michael Sveda, the Inventor Of Cyclamates, Dies at 87". New York Times. Archived from the original on September 12, 2017. Retrieved February 20, 2017.
  5. Taubes, Gary (2017). The Case against Sugar. London, England: Portobello books. pp. 143–144. ISBN   9781846276378.
  6. Chedd, Grahm (May 9, 1974). "The Search for Sweetness". New Scientist. 62 (897): 299.
  7. Goyan, Jere E., Commissioner of Food and Drugs. (September 4, 1980). "Cyclamate, Commissioner's Decision, 45 FR 61474" (PDF). Office of the Federal Register. pp. 61474–61530. Archived (PDF) from the original on April 12, 2015. Retrieved February 8, 2015. [...] approval of cyclamate for use as a sweetening agent in food and for technological purposes in food is denied.{{cite web}}: CS1 maint: multiple names: authors list (link)
  8. "FDA Talk Paper, NAS Report on Cyclamate" (PDF).
  9. "Petitions Currently Held in Abeyance". Food and Drug Administration . Archived from the original on February 8, 2015. Retrieved February 8, 2015. FAP 2A3672 Cyclamate (cyclamic acid, calcium cyclamate, and sodium cyclamate)
  10. 1 2 Weihrauch MR, Diehl V (2004). "Artificial sweeteners—do they bear a carcinogenic risk?". Ann Oncol. 15 (10): 1460–5. doi: 10.1093/annonc/mdh256 . PMID   15367404.
  11. "Worldwide Status of Cyclamate" (PDF). Calorie Control Council. Archived (PDF) from the original on February 4, 2022. Retrieved November 23, 2018.
  12. Ashurst, Philip R. (April 15, 2008). Chemistry and Technology of Soft Drinks and Fruit Juices. John Wiley & Sons. p. 247. ISBN   9781405141086.
  13. "FDA lifts ban on 'magic sugar' - Philstar.com". philstar.com. Archived from the original on May 15, 2022. Retrieved April 16, 2013.
  14. "High-Intensity Sweeteners". U.S. Food and Drug Administration. May 19, 2014. Archived from the original on April 23, 2019. Retrieved February 8, 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.
  15. "Substances Added to Food (formerly Everything Added to Food in the United States (EAFUS)), Search Criteria = "cyclamate"". U.S. Food and Drug Administration. Archived from the original on October 2, 2022. Retrieved February 8, 2015.
  16. Newton, David E (January 1, 2009). Food Chemistry. Infobase. pp. 73–77. ISBN   9781438109756.
  17. 사이클라민산나트륨 (in Korean). Retrieved August 23, 2018.
  18. "Tastes like sugar". Archived from the original on July 10, 2017. Retrieved November 1, 2010.
  19. Assugrin's website Archived July 1, 2007, at the Wayback Machine (in French)
  20. "Hermesetas".
  21. "Новапродукт". novaprodukt.ru. Archived from the original on December 6, 2011. Retrieved November 27, 2011.
  22. "Sucaryl". Archived from the original on June 29, 2015. Retrieved November 26, 2014.
  23. "SugarTwin - Artificial Sweeteners - Sugar Substitutes - Calorie Free". Sugar Twin. Archived from the original on January 16, 2022. Retrieved January 16, 2022.
  24. "Sugromax :: Home". Sugromax. Archived from the original on October 9, 2021. Retrieved October 9, 2021.
  25. "Labo-arrazi". Archived from the original on November 27, 2022. Retrieved May 5, 2023.

Related Research Articles

<span class="mw-page-title-main">Aspartame</span> Artificial non-saccharide sweetener

Aspartame is an artificial non-saccharide sweetener 200 times sweeter than sucrose and is commonly used as a sugar substitute in foods and beverages. It is a methyl ester of the aspartic acid/phenylalanine dipeptide with brand names NutraSweet, Equal, and Canderel. Aspartame was approved by the US Food and Drug Administration (FDA) in 1974, and then again in 1981, after approval was revoked in 1980.

<span class="mw-page-title-main">Food additive</span> Substances added to food

Food additives are substances added to food to preserve flavor or enhance taste, appearance, or other sensory qualities. Some additives have been used for centuries as part of an effort to preserve food, for example vinegar (pickling), salt (salting), smoke (smoking), sugar (crystallization), etc. This allows for longer-lasting foods such as bacon, sweets or wines. With the advent of processed foods in the second half of the twentieth century, many additives have been introduced, of both natural and artificial origin. Food additives also include substances that may be introduced to food indirectly in the manufacturing process, through packaging, or during storage or transport.

<span class="mw-page-title-main">Stevia</span> Sweetener and sugar substitute

Stevia is a sweet sugar substitute extracted from the leaves of the plant species Stevia rebaudiana native to Paraguay and Brazil.

<span class="mw-page-title-main">Sucralose</span> Chemical compound

Sucralose is an artificial sweetener and sugar substitute. The majority of ingested sucralose is not broken down by the body, so it is noncaloric. In the European Union, it is also known under the E number E955. It is produced by chlorination of sucrose, selectively replacing three of the hydroxy groups—in the C1 and C6 positions of fructose and the C4 position of glucose—to give a 1,6-dichloro-1,6-dideoxyfructose–4-chloro-4-deoxygalactose disaccharide. Sucralose is about 320 to 1,000 times sweeter than sucrose, three times as sweet as both aspartame and acesulfame potassium, and twice as sweet as sodium saccharin.

<span class="mw-page-title-main">Sugar substitute</span> Sugarless food additive intended to provide a sweet taste

A sugar substitute is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie or low-calorie sweetener. Artificial sweeteners may be derived through manufacturing of plant extracts or processed by chemical synthesis. Sugar substitute products are commercially available in various forms, such as small pills, powders, and packets.

<span class="mw-page-title-main">Neohesperidin dihydrochalcone</span> Chemical compound

Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus.

<span class="mw-page-title-main">Saccharin</span> Chemical compound

Saccharin, also called saccharine or benzosulfimide, or used in saccharin sodium or saccharin calcium forms, is a non-nutritive artificial sweetener. Saccharin is a benzoic sulfimide that is about 500 times sweeter than sucrose, but has a bitter or metallic aftertaste, especially at high concentrations. It is used to sweeten products, such as drinks, candies, baked goods, tobacco products, excipients, and for masking the bitter taste of some medicines. It appears as white crystals and is odorless.

<span class="mw-page-title-main">Acesulfame potassium</span> Calorie-free sugar substitute

Acesulfame potassium, also known as acesulfame K or Ace K, is a synthetic calorie-free sugar substitute often marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number E950. It was discovered accidentally in 1967 by German chemist Karl Clauss at Hoechst AG. In chemical structure, acesulfame potassium is the potassium salt of 6-methyl-1,2,3-oxathiazine-4(3H)-one 2,2-dioxide. It is a white crystalline powder with molecular formula C
4
H
4
KNO
4
S
and a molecular weight of 201.24 g/mol.

<span class="mw-page-title-main">Diet drink</span> Type of sugar-free or artificially sweetened soda

Diet or light beverages are generally sugar-free, artificially sweetened beverages with few or no calories. They are marketed for diabetics and other people who want to reduce their sugar and/or caloric intake.

<span class="mw-page-title-main">Tab (drink)</span> Diet cola brand

Tab was a diet cola soft drink produced and distributed by The Coca-Cola Company, introduced in 1963 and discontinued in 2020. The company's first diet drink, Tab was popular among some people throughout the 1960s and 1970s, as an alternative to Coca-Cola. Several variations were made, including a number of fruit-flavored, root beer, and ginger ale versions. Caffeine-free and clear variations were released in the late 1980s and early 1990s.

<span class="mw-page-title-main">Sweet'n Low</span> Brand of artificial sweetener

Sweet'n Low is a brand of artificial sweetener now made primarily from granulated saccharin. When introduced in 1958 in the United States, Sweet'n Low was cyclamate-based, but it was replaced by a saccharin-based formulation in 1969. It is also a brand name applied to a family of sweetener and sweetened products, some containing sweeteners other than saccharin or cyclamate. There have been over 500 billion Sweet'N Low packets produced.

<span class="mw-page-title-main">Dulcin</span> Chemical compound

Dulcin is an artificial sweetener about 250 times sweeter than sugar, discovered in 1883 by the Polish chemist Józef (Joseph) Berlinerblau. It was first mass-produced about seven years later. Although it was discovered only five years after saccharin, it never enjoyed the latter compound's market success. Nevertheless, it was an important sweetener of the early 20th century and had an advantage over saccharin in that it did not possess a bitter aftertaste.

<span class="mw-page-title-main">Alitame</span> Chemical compound

Alitame is an aspartic acid-containing dipeptide sweetener. It was developed by Pfizer in the early 1980s and currently marketed in some countries under the brand name Aclame. Most dipeptides are not sweet, but the unexpected discovery of aspartame in 1965 led to a search for similar compounds that shared its sweetness. Alitame is one such second-generation dipeptide sweetener. Neotame, developed by the owners of the NutraSweet brand, is another.

<span class="mw-page-title-main">Cyclamic acid</span> Chemical compound

Cyclamic acid is a compound with formula C6H13NO3S.

<span class="mw-page-title-main">Cumberland Packing Corporation</span> American food company

Cumberland Packing Corporation is a privately owned company located at 2 Cumberland Street, in Brooklyn, New York City. It was founded in 1945 by Benjamin Eisenstadt and is best known as the manufacturer, distributor, and marketer of Sweet'n Low, the saccharin-based zero-calorie sweetener sold in pink packets.

<span class="mw-page-title-main">Herbert L. Ley Jr.</span> Commissioner of the Food and Drug Administration

Herbert Leonard Ley Jr. was an American physician and the 10th Commissioner and head of the U.S. Food and Drug Administration (FDA).

Fruit2O, formerly manufactured by Kraft, is a lightly flavored, non-carbonated water beverage introduced in 1999. Fruit2o was introduced to compete not only with the bottled water market but also with the soft drink market. Sunny Delight Beverages purchased the Veryfine Products line from Kraft in 2007.

<span class="mw-page-title-main">Fizzies</span>

Fizzies were tablets that created a "carbonated" soft drink when added to water.

<span class="mw-page-title-main">Assugrin</span>

Assugrin is a brand name for a sugar substitute that is a blend of cyclamate and saccharin. Produced in Switzerland by MCM Klosterfrau Vertriebsgesellschaft, Assugrin was the main table sweetener in West Germany.