Sodium cyclamate
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Cyclamate is an
artificial sweetener 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 b ...
. It is 30–50 times sweeter than
sucrose Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula . For human consumption, sucrose is extracted and refine ...
(table sugar), making it the least potent of the commercially used artificial sweeteners. It is often used with other artificial sweeteners, especially
saccharin Saccharin (''aka'' saccharine, Sodium sacchari) is an artificial sweetener with effectively no nutritional value. It is about 550 times as sweet as sucrose but has a bitter or metallic aftertaste, especially at high concentrations. Saccharin is ...
; the mixture of 10 parts cyclamate to 1 part saccharin is common and masks the off-tastes of both sweeteners. It is less expensive than most sweeteners, including
sucralose 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 ...
, 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 Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable ...
or
calcium Calcium is a chemical element with the symbol Ca and atomic number 20. As an alkaline earth metal, calcium is a reactive metal that forms a dark oxide-nitride layer when exposed to air. Its physical and chemical properties are most similar ...
salt Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quant ...
of
cyclamic acid Cyclamic acid is a compound with formula C6H13NO3S. It is included in E number "E952". Cyclamic acid is mainly used as catalyst in the production of paints and plastics, and furthermore as a reagent for laboratory usage. The sodium and calciu ...
(cyclohexanesulfamic acid), which itself is prepared by reacting freebase
cyclohexylamine Cyclohexylamine is an organic compound, belonging to the aliphatic amine class. It is a colorless liquid, although, like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amine ...
with either
sulfamic acid Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, sulphamic acid and sulfamidic acid, is a molecular compound with the formula H3NSO3. This colourless, water-soluble compound finds many applications. Sulfami ...
or
sulfur trioxide Sulfur trioxide (alternative spelling sulphur trioxide, also known as ''nisso sulfan'') is the chemical compound with the formula SO3. It has been described as "unquestionably the most important economically" sulfur oxide. It is prepared on an ind ...
. 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 kerosene) with cyclohexylamine, chilled and filtered through a high speed centrifugal separator, dried, granulated and micro-pulverised for powder or tablet usage.


History

Cyclamate was discovered in 1937 at the
University of Illinois The University of Illinois Urbana-Champaign (U of I, Illinois, University of Illinois, or UIUC) is a public land-grant research university in Illinois in the twin cities of Champaign and Urbana. It is the flagship institution of the Uni ...
by graduate student
Michael Sveda Michael may refer to: People * Michael (given name), a given name * Michael (surname), including a list of people with the surname Michael Given name "Michael" * Michael (archangel), ''first'' of God's archangels in the Jewish, Christian an ...
. Sveda was working in the lab on the synthesis of an
antipyretic An antipyretic (, from ''anti-'' 'against' and ' 'feverish') is a substance that reduces fever. Antipyretics cause the hypothalamus to override a prostaglandin-induced increase in temperature. The body then works to lower the temperature, which r ...
drug. He put his
cigarette A cigarette is a narrow cylinder containing a combustible material, typically tobacco, that is rolled into thin paper for smoking. The cigarette is ignited at one end, causing it to smolder; the resulting smoke is orally inhaled via the opp ...
down on the lab bench, and when he put it back in his mouth, he discovered the sweet taste of cyclamate. The patent for cyclamate was purchased by
DuPont DuPont de Nemours, Inc., commonly shortened to DuPont, is an American multinational chemical company first formed in 1802 by French-American chemist and industrialist Éleuthère Irénée du Pont de Nemours. The company played a major role in ...
and later sold to
Abbott Laboratories Abbott Laboratories is an American multinational medical devices and health care company with headquarters in Abbott Park, Illinois, United States. The company was founded by Chicago physician Wallace Calvin Abbott in 1888 to formulate known dr ...
, 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 An antibiotic is a type of antimicrobial substance active against bacteria. It is the most important type of antibacterial agent for fighting bacterial infections, and antibiotic medications are widely used in the treatment and preventio ...
and
pentobarbital Pentobarbital (previously known as pentobarbitone in Britain and Australia) is a short-acting barbiturate typically used as a sedative, a preanesthetic, and to control convulsions in emergencies. It can also be used for short-term treatment of i ...
. In 1958, it was designated GRAS ( Generally Recognized as Safe) by the United States
Food and Drug Administration The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
. 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. In 1966, a study reported that some intestinal bacteria could desulfonate cyclamate to produce
cyclohexylamine Cyclohexylamine is an organic compound, belonging to the aliphatic amine class. It is a colorless liquid, although, like many amines, samples are often colored due to contaminants. It has a fishy odor and is miscible with water. Like other amine ...
, 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 Bladder cancer is any of several types of cancer arising from the tissues of the urinary bladder. Symptoms include blood in the urine, pain with urination, and low back pain. It is caused when epithelial cells that line the bladder become ma ...
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. 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 The United States Food and Drug Administration (FDA or US FDA) is a federal agency of the Department of Health and Human Services. The FDA is responsible for protecting and promoting public health through the control and supervision of food ...
Commissioner
Herbert L. Ley, Jr. Herbert Leonard Ley Jr. (September 7, 1923 – July 22, 2001) was an American physician and the 10th Commissioner and head of the U.S. Food and Drug Administration (FDA). Background Dr. Ley attended Harvard College from 1941-1943, and re ...
, 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. 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 Jere E. Goyan (August 3, 1930 – January 17, 2007) was an American pharmacist who served as Commissioner of Food and Drugs The United States Commissioner of Food and Drugs is the head of the Food and Drug Administration (FDA), an agency of th ...
. Abbott Labs, together with the
Calorie Control Council The calorie is a unit of energy. For historical reasons, two main definitions of "calorie" are in wide use. The large calorie, food calorie, or kilogram calorie was originally defined as the amount of heat needed to raise the temperature of ...
(a political
lobby Lobby may refer to: * Lobby (room), an entranceway or foyer in a building * Lobbying, the action or the group used to influence a viewpoint to politicians :* Lobbying in the United States, specific to the United States * Lobby (food), a thick st ...
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 A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive sub ...
in mice or rats, cyclamate remains banned from food products in the United States. The petition is now held in
abeyance Abeyance (from the Old French ''abeance'' meaning "gaping") is a state of expectancy in respect of property Property is a system of rights that gives people legal control of valuable things, and also refers to the valuable things themselves. ...
, though not actively considered. 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. The substance did not show any DNA-damaging properties in DNA repair assays.


Legal status

Cyclamate is approved as a sweetener in at least 130 countries. 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. In the
Philippines The Philippines (; fil, Pilipinas, links=no), officially the Republic of the Philippines ( fil, Republika ng Pilipinas, links=no), * bik, Republika kan Filipinas * ceb, Republika sa Pilipinas * cbk, República de Filipinas * hil, Republ ...
, cyclamate was banned until the Philippine Food and Drug Administration lifted the ban in 2013, declaring it safe for consumption. Cyclamate remains banned in the United States and South Korea.


Brands

Sweeteners produced by
Sweet'n Low Sweet'n Low (stylized as Sweet'N Low) is a brand of artificial sweetener made primarily from granulated saccharin. It also contains dextrose and cream of tartar, and is distributed primarily in packets. There have been over 500 billion Sweet' ...
and Sugar Twin for
Canada Canada is a country in North America. Its ten provinces and three territories extend from the Atlantic Ocean to the Pacific Ocean and northward into the Arctic Ocean, covering over , making it the world's second-largest country by to ...
contain cyclamate, though not those produced for the
United States The United States of America (U.S.A. or USA), commonly known as the United States (U.S. or US) or America, is a country Continental United States, primarily located in North America. It consists of 50 U.S. state, states, a Washington, D.C., ...
. *
Assugrin 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. History Cyclamate sugar substitu ...
(Switzerland, Brazil) * Cap Cangkir (Indonesia) * Chuker (Argentina) – Merisant Company 2, SARL * Cologran * Huxol (Germany) in liquid form * Novasweet (Russia) * Rio (Produced under license and authority of SweetLife AG Switzerland by SweetLife Ltd, China) * Sucaryl * Sugar Twin (Canada) * Suitli (Bulgaria) * Sweet'n Low (Canada) * Sugromax (New Zealand)


Notes and references


External links


European Commission Revised Opinion On Cyclamic Acid FDA Commissioner's Decision on Cyclamate, 45 FR 61474
{{Food Substitutes Abbott Laboratories Sulfamates Sugar substitutes
Cyclamate 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; ...
Cyclohexyl compounds Suspected carcinogens E-number additives