Saccharin is an artificial sweetener with effectively no food energy which is approximately
300 times as sweet as sucrose or table sugar, but has a bitter or metallic aftertaste, 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 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 cyclamate: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 aspartame 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 diabetics, as it goes directly through the human digestive system without
being digested. In its acid form, saccharin is not water-soluble.
The form used as an artificial sweetener is usually its sodium salt. The calcium 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.
Safety and health effects Saccharin has no food energy. It has been
suggested that it may trigger the release of insulin in humans and rats, as a result
of its taste, but this has not been confirmed in controlled studies." This is similar for
aspartame. However large amounts of saccharin has been shown to lead to significantly increased
glucose intolerance in mice and in some humans, likely due to interactions between saccharin
and gut bacteria. History
Saccharin was produced first in 1878 by Constantin Fahlberg, a chemist working on coal tar derivatives
in Ira Remsen's laboratory at the Johns Hopkins University. 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, then 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.
Two years later he began production of the substance in a factory in a suburb of Magdeburg,
Germany. Fahlberg would soon grow wealthy, while Remsen merely grew irritated, 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 I that its
use became widespread. Its popularity further increased during the 1960s and 1970s among
dieters, since saccharin is a calorie-free sweetener. In the United States, saccharin
is often found in restaurants in pink packets; the most popular brand is "Sweet'n Low".
Government regulation Starting in 1907, the USDA began investigating
saccharin as a direct result of the Pure Food and Drug Act. Harvey Wiley, then the director
of the bureau of chemistry for the USDA, viewed it as an illegal substitution of a valuable
ingredient by a less valuable ingredient. In a clash that had career consequences, Wiley
told President Theodore Roosevelt 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 was 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 being harmful to human health. In 1972, the
USDA made an attempt to completely ban the substance. However, this attempt was also
unsuccessful, and the sweetener continued to be widely used in the United States. It
is now the third most popular artificial sweetener behind sucralose and aspartame.
In the European Union, saccharin is also known by the E number E954.
The current status of saccharin is that it is allowed in most countries, and countries
like Canada have lifted their previous ban of it as a food additive. The claims that
it is associated with bladder cancer were shown to be unfounded 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 65, but it was delisted in 2001.
Warning label addition and removal In 1958, the United States Congress amended
the Food, Drugs, and Cosmetic Act of 1938 with the Delaney clause to mandate that the
Food and Drug Administration 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 meeting the requirement of
the Saccharin Study and Labeling Act of 1977. 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. Since this does not occur in humans, there is no elevated risk of bladder
cancer. The delisting of saccharin led to legislation,
known as the Sweetness Act; 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
Administration and the state of California 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. Chemistry
Saccharin can be produced in various ways. The original route by Remsen & Fahlberg starts
with toluene; another route begins with o-chlorotoluene. Sulfonation by chlorosulfonic acid gives the
ortho and para substituted sulfonyl chlorides. The ortho isomer is separated and converted
to the sulfonamide with ammonia. Oxidation of the methyl substituent gives the carboxylic
acid, which cyclicizes to give saccharin free acid:
In 1950, an improved synthesis was developed at the Maumee Chemical Company of Toledo,
Ohio. In this synthesis, anthranilic acid successively reacts with nitrous acid, sulfur
dioxide, chlorine, and then ammonia to yield saccharin:
The free acid of saccharin has a low pKa of about 2. Saccharin can be used to prepare
exclusively disubstituted amines from alkyl halides via a nucleophilic substitution, followed
by Gabriel synthesis. See also
Sugar substitute Sweet'N Low
Assugrin Cyclamate
Sucralose Aspartame
Neotame Steviol glycoside
Xylitol Notes and references