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| Names | |
|---|---|
| Preferred IUPAC name Sodium cyclohexylsulfamate | |
| Identifiers | |
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3D model (JSmol) | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.004.863 |
| E number | E952(iv)(glazing agents, ...) |
| UNII | |
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| Properties | |
| C6H12NNaO3S | |
| Molar mass | 201.22 g·mol−1 |
| Hazards | |
| NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Cyclamate is anartificial sweetener. It is 30–50 times sweeter thansucrose (table sugar), making it the least potent of the commercially used artificial sweeteners. It is often used with other artificial sweeteners, especiallysaccharin; 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, includingsucralose, and is stable under heating. Safety concerns led to it being banned in a few countries, though theEuropean Union considers it safe.
Cyclamate is thesodium orcalciumsalt ofcyclamic acid (cyclohexanesulfamic acid), which itself is prepared by reacting freebasecyclohexylamine with eithersulfamic acid orsulfur 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]
Cyclamate was discovered in 1937 at theUniversity of Illinois by graduate studentMichael Sveda. Sveda was working in the lab on the synthesis of anantipyretic drug. He put hiscigarette 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 byDuPont and later sold toAbbott 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 asantibiotics andpentobarbital. In 1958, it was designated GRAS (generally recognized as safe) by the United StatesFood 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 producecyclohexylamine, 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 ofbladder cancer inrats. 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 SecretaryRobert Finch, bypassingFood and Drug Administration CommissionerHerbert 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 CommissionerJere Goyan.[7] Abbott Labs, together with theCalorie Control Council (a politicallobby 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 acarcinogen in mice or rats,[8] cyclamate remains banned from food products in the United States. The petition is now held inabeyance, 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, occurred at the same frequency as expected in healthy monkeys, 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 theUnited Kingdom; however, it was approved after being re-evaluated by the European Union in 1996.[12]
In thePhilippines, cyclamate was banned until thePhilippine Food and Drug Administration lifted the ban in 2013, declaring it safe for consumption.[13] Cyclamate remains banned in the United States,South Korea, andBangladesh.[14][15][16][17]
Sweeteners produced bySweet'n Low and Sugar Twin[18] forCanada contain cyclamate, though not those produced for theUnited States.
[...] 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)FAP 2A3672 Cyclamate (cyclamic acid, calcium cyclamate, and sodium cyclamate)
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.
