Names | |
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Preferred IUPAC name Sodium cyclohexylsulfamate | |
Identifiers | |
3D model (JSmol) | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.004.863 |
E number | E952(iv) (glazing agents, ...) |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
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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 their standard state (at 25 °C [77 °F], 100 kPa). |
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.
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 ]
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, South Korea, and Bangladesh. [14] [15] [16] [17]
Sweeteners produced by Sweet'n Low and Sugar Twin [18] for Canada contain cyclamate, though not those produced for the United States.
[...] approval of cyclamate for use as a sweetening agent in food and for technological purposes in food is denied.
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: 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.
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.
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 ultra-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.
Stevia is a sweet sugar substitute that is about 50 to 300 times sweeter than sugar. It is extracted from the leaves of Stevia rebaudiana, a plant native to areas of Paraguay and Brazil in the southern Amazon rainforest. The active compounds in stevia are steviol glycosides. Stevia is heat-stable, pH-stable, and not fermentable. Humans cannot metabolize the glycosides in stevia, and therefore it has zero calories. Its taste has a slower onset and longer duration than that of sugar, and at high concentrations some of its extracts may have an aftertaste described as licorice-like or bitter. Stevia is used in sugar- and calorie-reduced food and beverage products as an alternative for variants with sugar.
Sucralose is an artificial sweetener and sugar substitute. As the majority of ingested sucralose is not metabolized by the body, it adds very little food energy. 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 the fructose portion and the C4 position of the glucose portion—to give a 1,6-dichloro-1,6-dideoxyfructose–4-chloro-4-deoxygalactose disaccharide. Sucralose is about 600 times sweeter than sucrose, 3 times as sweet as both aspartame and acesulfame potassium, and 2 times as sweet as sodium saccharin.
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.
Neohesperidin dihydrochalcone, sometimes abbreviated to neohesperidin DC or simply NHDC, is an artificial sweetener derived from citrus.
Saccharin, also called saccharine, benzosulfimide, or E954, or used in saccharin sodium or saccharin calcium forms, is a non-nutritive artificial sweetener. Saccharin is a sultam 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.
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. 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
4H
4KNO
4S and a molecular weight of 201.24 g/mol.
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.
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.
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.
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.
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.
Cyclamic acid is a compound with formula C6H13NO3S.
D-Psicose (C6H12O6), also known as D-allulose, or simply allulose, is a low-calorie epimer of the monosaccharide sugar fructose, used by some major commercial food and beverage manufacturers as a low-calorie sweetener. First identified in wheat in the 1940s, allulose is naturally present in small quantities in certain foods.
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, a saccharin-based zero-calorie sweetener sold in pink packets.
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.
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.