Cyclamate
Encyclopedia
Sodium cyclamate is an artificial sweetener. It is 30–50 times sweeter than sugar (depending on concentration; it is not a linear relationship), making it the least potent of the commercially used artificial sweeteners. Some people find it to have an unpleasant aftertaste
, but, in general, less so than saccharin
or acesulfame potassium
. It is often used synergistically 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. It is less expensive than most sweeteners, including sucralose
, and is stable under heating.
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
.
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.
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 US 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; one such product was named 'Sucaryl' and is still available in non-US markets.
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 rat
s. 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. Other studies implicated cyclohexylamine in testicular
atrophy in mice
. On October 18, 1969, the Food and Drug Administration
banned its sale in the United States
with citation of the Delaney Amendment
after reports that large quantities of cyclamates could cause liver damage, bladder cancer, birth mutations and defects, reduce testosterone or shrivel the testes. In the same month, cyclamate was approved for use in the United Kingdom and is still used in low-calorie drinks;
it is still available without restriction in the UK and Europe. As cyclamate is stable in heat, it was and is marketed as suitable for use in cooking and baking. Commercially, it is available as Sucaryl™.
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. 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, cyclamate remains banned from food products in the United States. The petition is now held in abeyance, 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.
Sweeteners produced by Sweet'N Low
and Sugar Twin for Canada
contain cyclamate, though not for those deployed in the United States
.
, 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.
In the Philippines
, Magic Sugar, a brand of cyclamate, has been banned. It was placed in coconut juices by local street-side vendors.
Aftertaste
Aftertaste is the taste intensity of a food or beverage that is perceived immediately after that food or beverage is removed from the mouth. The aftertastes of different foods and beverages can vary by intensity and over time, but the unifying feature of aftertaste is that it is perceived after a...
, but, in general, less so than saccharin
Saccharin
Saccharin is an artificial sweetener. The basic substance, benzoic sulfilimine, has effectively no food energy and is much sweeter than sucrose, but has a bitter or metallic aftertaste, especially at high concentrations...
or acesulfame potassium
Acesulfame potassium
Acesulfame potassium is a calorie-free artificial sweetener, also known as Acesulfame K or Ace K , and marketed under the trade names Sunett and Sweet One. In the European Union, it is known under the E number E950...
. It is often used synergistically 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. It is less expensive than most sweeteners, including sucralose
Sucralose
Sucralose is an artificial sweetener. The majority of ingested sucralose is not broken down by the body and therefore it is non-caloric. In the European Union, it is also known under the E number E955. Sucralose is approximately 600 times as sweet as sucrose , twice as sweet as saccharin, and 3.3...
, and is stable under heating.
Chemistry
Cyclamate is the sodiumSodium
Sodium is a chemical element with the symbol Na and atomic number 11. It is a soft, silvery-white, highly reactive metal and is a member of the alkali metals; its only stable isotope is 23Na. It is an abundant element that exists in numerous minerals, most commonly as sodium chloride...
or calcium
Calcium
Calcium is the chemical element with the symbol Ca and atomic number 20. It has an atomic mass of 40.078 amu. Calcium is a soft gray alkaline earth metal, and is the fifth-most-abundant element by mass in the Earth's crust...
salt
Salt
In chemistry, salts are ionic compounds that result from the neutralization reaction of an acid and a base. They are composed of cations and anions so that the product is electrically neutral...
of cyclamic acid
Cyclamic acid
Cyclamic acid is a compound with formula C6H11NHSO2OH.It is included in E number "E952".Cyclamic Acid is mainly used as catalyst in the production of paints and plastics, and furthermore as reagent for laboratories....
(cyclohexanesulfamic acid), which itself is prepared by the sulfonation of cyclohexylamine
Cyclohexylamine
Cyclohexylamine, also called hexahydroaniline, 1-aminocyclohexane, or aminohexahydrobenzene, is an organic chemical, an amine derived from cyclohexane. It is a clear to yellowish liquid with fishy odor, with melting point of −17.7 °C and boiling point 134.5 °C, miscible with water...
. This can be accomplished by reacting cyclohexylamine with either sulfamic acid
Sulfamic acid
Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, and sulfamidic acid, is a molecular compound with the formula H3NSO3...
or sulfur trioxide
Sulfur trioxide
Sulfur trioxide is the chemical compound with the formula SO3. In the gaseous form, this species is a significant pollutant, being the primary agent in acid rain. It is prepared on massive scales as a precursor to sulfuric acid.-Structure and bonding:Gaseous SO3 is a trigonal planar molecule of...
.
History
University of Illinois at Urbana-Champaign
The University of Illinois at Urbana–Champaign is a large public research-intensive university in the state of Illinois, United States. It is the flagship campus of the University of Illinois system...
by graduate student Michael Sveda. Sveda was working in the lab on the synthesis of anti-fever medication. He put his cigarette
Cigarette
A cigarette is a small roll of finely cut tobacco leaves wrapped in a cylinder of thin paper for smoking. The cigarette is ignited at one end and allowed to smoulder; its smoke is inhaled from the other end, which is held in or to the mouth and in some cases a cigarette holder may be used as well...
down on the lab bench, and, when he put it back in his mouth
Mouth
The mouth is the first portion of the alimentary canal that receives food andsaliva. The oral mucosa is the mucous membrane epithelium lining the inside of the mouth....
, he discovered the sweet taste of cyclamate.
The patent for cyclamate was purchased by DuPont
DuPont
E. I. du Pont de Nemours and Company , commonly referred to as DuPont, is an American chemical company that was founded in July 1802 as a gunpowder mill by Eleuthère Irénée du Pont. DuPont was the world's third largest chemical company based on market capitalization and ninth based on revenue in 2009...
but later sold to Abbott Laboratories
Abbott Laboratories
Abbott Laboratories is an American-based global, diversified pharmaceuticals and health care products company. It has 90,000 employees and operates in over 130 countries. The company headquarters are in Abbott Park, North Chicago, Illinois. The company was founded by Chicago physician, 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 and pentobarbital
Pentobarbital
Pentobarbital is a short-acting barbiturate that was first synthesized in 1928. Pentobarbital is available as both a free acid and a sodium salt, the former of which is only slightly soluble in water and ethanol....
. In the US in 1958, it was designated GRAS (Generally Recognized as Safe
Generally recognized as safe
Generally recognized as safe is an American Food and Drug Administration designation that a chemical or substance added to food is considered safe by experts, and so is exempted from the usual Federal Food, Drug, and Cosmetic Act food additive tolerance requirements.-History:On January 1, 1958,...
). Cyclamate was marketed in tablet form for use by diabetics as an alternative tabletop sweetener, as well as in a liquid form; one such product was named 'Sucaryl' and is still available in non-US markets.
Controversy developed when, in 1966, a study reported that some intestinal bacteria could desulfonate cyclamate to produce cyclohexylamine
Cyclohexylamine
Cyclohexylamine, also called hexahydroaniline, 1-aminocyclohexane, or aminohexahydrobenzene, is an organic chemical, an amine derived from cyclohexane. It is a clear to yellowish liquid with fishy odor, with melting point of −17.7 °C and boiling point 134.5 °C, miscible with water...
, 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
Urinary bladder
The urinary bladder is the organ that collects urine excreted by the kidneys before disposal by urination. A hollow muscular, and distensible organ, the bladder sits on the pelvic floor...
cancer
Cancer
Cancer , known medically as a malignant neoplasm, is a large group of different diseases, all involving unregulated cell growth. In cancer, cells divide and grow uncontrollably, forming malignant tumors, and invade nearby parts of the body. The cancer may also spread to more distant parts of the...
in rat
Rat
Rats are various medium-sized, long-tailed rodents of the superfamily Muroidea. "True rats" are members of the genus Rattus, the most important of which to humans are the black rat, Rattus rattus, and the brown rat, Rattus norvegicus...
s. 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. Other studies implicated cyclohexylamine in testicular
Testicle
The testicle is the male gonad in animals. Like the ovaries to which they are homologous, testes are components of both the reproductive system and the endocrine system...
atrophy in mice
Mouse
A mouse is a small mammal belonging to the order of rodents. The best known mouse species is the common house mouse . It is also a popular pet. In some places, certain kinds of field mice are also common. This rodent is eaten by large birds such as hawks and eagles...
. On October 18, 1969, the Food and Drug Administration
Food and Drug Administration
The Food and Drug Administration is an agency of the United States Department of Health and Human Services, one of the United States federal executive departments...
banned its sale in the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...
with citation of the Delaney Amendment
Delaney clause
The Delaney Clause is a 1958 amendment to the Food, Drugs, and Cosmetic Act of 1938, named after Congressman James Delaney of New York.It said:...
after reports that large quantities of cyclamates could cause liver damage, bladder cancer, birth mutations and defects, reduce testosterone or shrivel the testes. In the same month, cyclamate was approved for use in the United Kingdom and is still used in low-calorie drinks;
it is still available without restriction in the UK and Europe. As cyclamate is stable in heat, it was and is marketed as suitable for use in cooking and baking. Commercially, it is available as Sucaryl™.
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. Abbott Labs, together with the Calorie Control Council (a political lobby
Lobbying
Lobbying is the act of attempting to influence decisions made by officials in the government, most often legislators or members of regulatory agencies. Lobbying is done by various people or groups, from private-sector individuals or corporations, fellow legislators or government officials, or...
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, cyclamate remains banned from food products in the United States. The petition is now held in abeyance, 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.
Status
Cyclamate is approved as a sweetener in over 55 countries, though it is banned in the United States.Sweeteners produced by Sweet'N Low
Sweet'N Low
Sweet'n Low is a brand of artificial sweetener from granulated saccharin, dextrose and cream of tartar. It was invented and first introduced in 1957 by Benjamin Eisenstadt and his son, Marvin Eisenstadt...
and Sugar Twin for Canada
Canada
Canada is a North American country consisting of ten provinces and three territories. Located in the northern part of the continent, it extends from the Atlantic Ocean in the east to the Pacific Ocean in the west, and northward into the Arctic Ocean...
contain cyclamate, though not for those deployed in the United States
United States
The United States of America is a federal constitutional republic comprising fifty states and a federal district...
.
Health
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."Incidences
In TaipeiTaipei
Taipei City is the capital of the Republic of China and the central city of the largest metropolitan area of Taiwan. Situated at the northern tip of the island, Taipei is located on the Tamsui River, and is about 25 km southwest of Keelung, its port on the Pacific Ocean...
, Taiwan, a city health survey in 2010 found nearly 30% of tested dried fruit
Dried fruit
Dried fruit is fruit where the majority of the original water content has been removed either naturally, through sun drying, or through the use of specialized dryers or dehydrators. Dried fruit has a long tradition of use dating back to the fourth millennium BC in Mesopotamia, and is prized...
products failed a health standards test, most having excessive amounts of cyclamate, some at levels 20 times higher than the legal limit.
In the Philippines
Philippines
The Philippines , officially known as the Republic of the Philippines , is a country in Southeast Asia in the western Pacific Ocean. To its north across the Luzon Strait lies Taiwan. West across the South China Sea sits Vietnam...
, Magic Sugar, a brand of cyclamate, has been banned. It was placed in coconut juices by local street-side vendors.
Brands
- AssugrinAssugrinAssugrin is a brand name for a sugar substitute that is a blend of cyclamate and saccharin. Produced in Switzerland by MCM Klosterfrau Vertriebsgesellschaft, Assugrin is the main table sweetener in West Germany.-History:...
(Switzerland, Brazil) - Sucaryl
- Sugar Twin (Canada)
- Chuker (Argentina) - Merisant Company 2, SARL
- Cologran
- Novasweet (Russia)
External links
- Rosalindfranklin.edu
- European Commission Revised Opinion On Cyclamic Acid
- US FDA Petitions Currently Held in Abeyance
- List of other chemical and brand names for cyclamate
- A brief history of sweeteners, including the discovery of cyclamate
- Assugrin's website
- concerns over potential "testicular wasting" in male users