Saccharin is an artificial sweetener. The basic substance, benzoic
sulfilimineA sulfilimine is a type of chemical compound containing a sulfur to nitrogen double bond. The parent compound is sulfilimine H2S=NH. Examples are methylphenylsulfoximine and S,S-diphenylsulfilimine :-Sulfilimine bonds in proteins:...
, has effectively no
food energyFood energy is the amount of energy obtained from food that is available through cellular respiration.Food energy is expressed in food calories or kilojoules...
and is much sweeter than
sucroseSucrose is the organic compound commonly known as table sugar and sometimes called saccharose. A white, odorless, crystalline powder with a sweet taste, it is best known for its role in human nutrition. The molecule is a disaccharide composed of glucose and fructose with the molecular formula...
, but has a bitter or metallic
aftertasteAftertaste 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...
, especially at high concentrations. It is used to sweeten products such as drinks, candies, cookies, medicines, and toothpaste.
Origins
Saccharin derives its name from the word
Saccharine, meaning of, relating to, or resembling that of sugar.
Properties
Saccharin is unstable when heated but it does not react chemically with other food ingredients. As such, it stores well. Blends of saccharin with other sweeteners are often used to compensate for each sweetener's weaknesses and faults. A 10:1
cyclamateSodium cyclamate is an artificial sweetener. It is 30–50 times sweeter than sugar , 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...
:saccharin blend is common in countries where both these sweeteners are legal; in this blend, each sweetener masks the other's off-taste. Saccharin is often used together with
aspartameAspartame is an artificial, non-saccharide sweetener used as a sugar substitute in some foods and beverages. In the European Union, it is codified as E951. Aspartame is a methyl ester of the aspartic acid/phenylalanine dipeptide. It was first sold under the brand name NutraSweet; since 2009 it...
in diet carbonated soft drinks, so that some sweetness remains should the fountain syrup be stored beyond aspartame's relatively short shelf-life. Saccharin is believed to be an important discovery, especially for
diabeticsDiabetes mellitus, often simply referred to as diabetes, is a group of metabolic diseases in which a person has high blood sugar, either because the body does not produce enough insulin, or because cells do not respond to the insulin that is produced...
, as it goes directly through the human digestive system without being digested. Although saccharin has no
food energyFood energy is the amount of energy obtained from food that is available through cellular respiration.Food energy is expressed in food calories or kilojoules...
, it can trigger the release of
insulinInsulin is a hormone central to regulating carbohydrate and fat metabolism in the body. Insulin causes cells in the liver, muscle, and fat tissue to take up glucose from the blood, storing it as glycogen in the liver and muscle....
in humans and rats, presumably as a result of its taste, as can other sweeteners like aspartame.
In its acid form, saccharin is not water-soluble. The form used as an artificial sweetener is usually its
sodiumSodium 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...
salt. The
calciumCalcium 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 is also sometimes used, especially by people restricting their dietary sodium intake. Both salts are highly water-soluble: 0.67 grams per milliliter water at room temperature.
History
Saccharin was produced first in 1878 by
Constantin FahlbergConstantin Fahlberg ) discovered the sweet taste of anhydroorthosulphaminebenzoic acid in 1877/78 when analysing the chemical compounds in coal tar at Johns Hopkins University for Professor Ira Remsen...
, a chemist working on coal tar derivatives in
Ira RemsenIra Remsen was a chemist who, along with Constantin Fahlberg, discovered the artificial sweetener saccharin. He was the second president of Johns Hopkins University.-Biography:...
's laboratory at the
Johns Hopkins UniversityThe Johns Hopkins University, commonly referred to as Johns Hopkins, JHU, or simply Hopkins, is a private research university based in Baltimore, Maryland, United States...
. The sweet taste of saccharin was discovered when Fahlberg noticed a sweet taste on his hand one evening, and connected this with the compound that he had been working on that day. Fahlberg and Remsen published articles on benzoic sulfimide in 1879 and 1880. In 1884, now working on his own in New York City, Fahlberg applied for patents in several countries, describing methods of producing this substance that he named saccharin. Fahlberg would soon grow wealthy, while Remsen merely grew irate, believing that he deserved credit for substances produced in his laboratory. On the matter, Remsen commented, "Fahlberg is a scoundrel. It nauseates me to hear my name mentioned in the same breath with him."
Although saccharin was commercialized not long after its discovery, it was not until sugar shortages during
World War IWorld War I , which was predominantly called the World War or the Great War from its occurrence until 1939, and the First World War or World War I thereafter, was a major war centred in Europe that began on 28 July 1914 and lasted until 11 November 1918...
that its use became widespread. Its popularity further increased during the 1960s and 1970s among dieters, since saccharin is a
calorieThe calorie is a pre-SI metric unit of energy. It was first defined by Nicolas Clément in 1824 as a unit of heat, entering French and English dictionaries between 1841 and 1867. In most fields its use is archaic, having been replaced by the SI unit of energy, the joule...
-free sweetener. In the United States, saccharin is often found in restaurants in
pinkPink is a mixture of red and white. Commonly used for Valentine's Day and Easter, pink is sometimes referred to as "the color of love." The use of the word for the color known today as pink was first recorded in the late 17th century....
packets; the most popular brand is "
Sweet'N LowSweet'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...
".
Chemistry
Saccharin can be produced in various ways; another route begins with o-
chlorotolueneChlorotoluene can refer to any of four isomeric chemical compounds. Three isomers consisist of a disubsituted benzene ring with one chlorine atom and one methyl group...
.
The original route by Remsen & Fahlberg starts with
tolueneToluene, formerly known as toluol, is a clear, water-insoluble liquid with the typical smell of paint thinners. It is a mono-substituted benzene derivative, i.e., one in which a single hydrogen atom from the benzene molecule has been replaced by a univalent group, in this case CH3.It is an aromatic...
. Sulfonation by chlorosulfonic acid gives the
ortho and
para substituted chlorosulfonic acids. The
ortho isomer is separated and converted to the
sulfonamideSulfonamide or sulphonamide may refer to:*Sulfonamide – the sulfonamide functional group. *Sulfonamide – the group of sulfonamide antibacterial drugs....
with
ammoniaAmmonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
. Oxidation of the methyl substituent gives the carboxylic acid, which forms the cyclicizes to give saccharin free acid:
In 1950, an improved synthesis was developed at the Maumee Chemical Company of
Toledo, OhioToledo is the fourth most populous city in the U.S. state of Ohio and is the county seat of Lucas County. Toledo is in northwest Ohio, on the western end of Lake Erie, and borders the State of Michigan...
. In this synthesis,
anthranilic acidAnthranilic acid is the organic compound with the formula C6H4COOH. This amino acid is a white solid when pure, although commercial samples may appear yellow. The molecule consists of a benzene ring with two adjacent functional groups, a carboxylic acid and an amine...
successively reacts with
nitrous acidNitrous acid is a weak and monobasic acid known only in solution and in the form of nitrite salts.Nitrous acid is used to make diazides from amines; this occurs by nucleophilic attack of the amine onto the nitrite, reprotonation by the surrounding solvent, and double-elimination of water...
(from
sodium nitriteSodium nitrite is the inorganic compound with the chemical formula NaNO2. It is a white to slight yellowish crystalline powder that is very soluble in water and is hygroscopic...
and
hydrochloric acidHydrochloric acid is a solution of hydrogen chloride in water, that is a highly corrosive, strong mineral acid with many industrial uses. It is found naturally in gastric acid....
,
sulfur dioxideSulfur dioxide is the chemical compound with the formula . It is released by volcanoes and in various industrial processes. Since coal and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide unless the sulfur compounds are removed before burning the fuel...
,
chlorineChlorine is the chemical element with atomic number 17 and symbol Cl. It is the second lightest halogen, found in the periodic table in group 17. The element forms diatomic molecules under standard conditions, called dichlorine...
, and then
ammoniaAmmonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
to yield saccharin:
The free acid of saccharin has a low
pKaAn acid dissociation constant, Ka, is a quantitative measure of the strength of an acid in solution. It is the equilibrium constant for a chemical reaction known as dissociation in the context of acid-base reactions...
of about 2 (the acidic hydrogen being that attached to the nitrogen). Saccharin can be used to prepare exclusively disubstituted
amineAmines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
s from alkyl halides via a
Gabriel synthesisThe Gabriel synthesis is named for the German chemist Siegmund Gabriel. Traditionally, it is a chemical reaction that transforms primary alkyl halides into primary amines using potassium phthalimide....
.
Government regulation
Starting in 1907, the USDA began investigating saccharin as a direct result of the
Pure Food and Drug ActThe Pure Food and Drug Act of June 30, 1906, is a United States federal law that provided federal inspection of meat products and forbade the manufacture, sale, or transportation of adulterated food products and poisonous patent medicines...
. Harvey Wiley, then the director of the bureau of chemistry for the USDA, viewed it as an illegal substitution of a valuable ingredient (sugar) by a less valuable ingredient. In a clash that had career consequences, Wiley told then President
Theodore RooseveltTheodore "Teddy" Roosevelt was the 26th President of the United States . He is noted for his exuberant personality, range of interests and achievements, and his leadership of the Progressive Movement, as well as his "cowboy" persona and robust masculinity...
that "Everyone who ate that sweet corn was deceived. He thought he was eating sugar, when in point of fact he was eating a coal tar product totally devoid of food value and extremely injurious to health." But Roosevelt himself was a consumer of saccharin, and, in a heated exchange, Roosevelt angrily answered Wiley by stating, "Anybody who says saccharin is injurious to health is an idiot." The episode proved the undoing of Wiley's career.
In 1911, the Food Inspection Decision 135 stated that foods containing saccharin were adulterated. However, in 1912, Food Inspection Decision 142 stated that saccharin is not harmful.
More controversy was stirred in 1969 with the discovery of files from the FDA's investigations of 1948 and 1949. These investigations, which had originally argued against saccharin use, were shown to prove little about saccharin's being harmful to human health. In 1972, the USDA made an attempt to completely ban the substance. However, this attempt was also unsuccessful, and so the sweetener continued to be widely used in the United States. It is now the most popular after
sucraloseSucralose 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
aspartameAspartame is an artificial, non-saccharide sweetener used as a sugar substitute in some foods and beverages. In the European Union, it is codified as E951. Aspartame is a methyl ester of the aspartic acid/phenylalanine dipeptide. It was first sold under the brand name NutraSweet; since 2009 it...
.
In the European Union, saccharin is also known by the
E numberE numbers are number codes for food additives that have been assessed for use within the European Union . They are commonly found on food labels throughout the European Union. Safety assessment and approval are the responsibility of the European Food Safety Authority...
(additive code)
E954.
The current status of saccharin is that it is allowed in most countries, and countries like Canada are considering lifting their previous ban of it as a food additive. The concerns that it is associated with bladder cancer were proven to be without foundation in experiments on primates.
Saccharin was formerly on California's list of chemicals known to the state to cause cancer for the purposes of
Proposition 65Proposition 65 is a California law passed by direct voter initiative in 1986 by a 63%-37% margin...
, but it was delisted in 2001.
Warning label added and removed
In 1958, the United States Congress amended the
Food, Drugs, and Cosmetic Act of 1938The United States Federal Food, Drug, and Cosmetic Act , is a set of laws passed by Congress in 1938 giving authority to the U.S. Food and Drug Administration to oversee the safety of food, drugs, and cosmetics. A principal author of this law was Royal S. Copeland, a three-term U.S. Senator from...
with the
Delaney clauseThe 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:...
to mandate that the
Food and Drug AdministrationThe 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...
not approve substances that "induce cancer in man, or, after tests, [are] found to induce cancer in animals." Studies in laboratory rats during the early 1970s linked saccharin with the development of bladder cancer in rodents. As a consequence, all food containing saccharin was labeled with a warning.
However, in 2000, the warning labels were removed because scientists learned that rodents, unlike humans, have a unique combination of high pH, high calcium phosphate, and high protein levels in their urine. One or more of the proteins that are more prevalent in male rats combine with calcium phosphate and saccharin to produce microcrystals that damage the lining of the bladder. Over time, the rat's bladder responds to this damage by over-producing cells to repair the damage, which leads to tumor formation. As this does not occur in humans, there is no elevated bladder cancer risk.
The delisting of saccharin led to legislation, which was signed into law on December 21, 2000, repealing the warning label requirement for products containing saccharin. In 2001, the U.S.
Food and Drug AdministrationThe 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...
and the state of
CaliforniaCalifornia is a state located on the West Coast of the United States. It is by far the most populous U.S. state, and the third-largest by land area...
reversed their positions on saccharin, declaring it safe for consumption. The FDA’s decision followed a 2000 determination by the U.S. Department of Health and Human Services' National Toxicology Program to remove saccharin from its list of carcinogens.
The EPA has officially removed saccharin and its salts from their list of hazardous constituents and commercial chemical products. In a December 14, 2010 release, the EPA stated that saccharin is no longer considered a potential hazard to human health.
See also
- Cyclamate
Sodium cyclamate is an artificial sweetener. It is 30–50 times sweeter than sugar , 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...
- 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...
(Splenda)
- Aspartame
Aspartame is an artificial, non-saccharide sweetener used as a sugar substitute in some foods and beverages. In the European Union, it is codified as E951. Aspartame is a methyl ester of the aspartic acid/phenylalanine dipeptide. It was first sold under the brand name NutraSweet; since 2009 it...
(EqualEqual is a brand of artificial sweetener containing aspartame, dextrose and maltodextrin. It is marketed as a tabletop sweetener by Merisant, a global corporation which also owns the well-known NutraSweet brand and which has headquarters in Chicago, Illinois, Switzerland, Mexico, and Australia...
, NutraSweetThe NutraSweet Company makes and sells NutraSweet, their trademarked brand name for the artificial sweetener aspartame, and Neotame.Aspartame was accidentally discovered in 1965 by James M. Schlatter, a chemist with a master's degree working under Dr. Kurt Rorig, PhD, in charge of new drug research...
, and CanderelCanderel is a brand of artificial sweetener made mainly from aspartame. Canderel is marketed by The Merisant Company, a global corporation with headquarters in Chicago, Illinois, also Switzerland, Mexico, and Australia....
)
- Neotame
Neotame is an artificial sweetener made by NutraSweet that is between 7,000 and 13,000 times sweeter than sucrose . In the European Union, it is known by the E number E961...
- Steviol glycoside
The steviol glycosides are responsible for the sweet taste of the leaves of the stevia plant .These compounds range in sweetness from 40 to 300 times sweeter than sucrose.They are heat-stable, pH-stable, and do not ferment...
- Xylitol
Xylitol is a sugar alcohol sweetener used as a naturally occurring sugar substitute. It is found in the fibers of many fruits and vegetables, and can be extracted from various berries, oats, and mushrooms, as well as fibrous material such as corn husks and sugar cane bagasse, and birch...