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SUCRALOSE


''[1]
Sucralose

Ball-and-stick model of sucralose
Chemical name
Other names 1',4,6'-Trichlorogalactosucrose
Trichlorosucrose
Chemical formula
Molecular mass g/mol
CAS number []
Density g/cm³
Melting point °C
SMILES

'Sucralose' is an artificial sweetener. Its generic name is 'Altern'. In the European Union, it is also known under the E number (additive code) 'E955'. 'Sucralose' is sold under the trade name of 'Splenda'. Sucralose is 600 times sweeter than sucrose (table sugar),Michael A. Friedman, Lead Deputy Commissioner for the FDA, Food Additives Permitted for Direct Addition to Food for Human Consumption; Sucralose Federal Register: 21 CFR Part 172, Docket No. 87F-0086, April 3, 1998
It is approximately twice as sweet as saccharin and four times as sweet as aspartame. Unlike aspartame it is stable under heat and over a broad range of pH conditions and can be used in baking or in products that require a longer shelf life. Since its introduction in 1999 sucralose has overtaken Equal in the $1.5 billion artificial sweetener market, holding a 62% market share.[2]According to market research firm IRI, as reported in the Wall Street Journal, Splenda sold $212 million in 2006 in the US while Equal sold $48.7 million.[3]

Contents
History
Packaging and storage
Energy (caloric) content
Use in branded products
Cooking
Safety
Criticisms and controversy
Litigation between the makers of Splenda and Equal
See also
References
External links
Science
Press Releases

History


Sucralose was discovered in 1976 by scientists from Tate & Lyle, working with researchers Leslie Hough and Shashikant Phadnis at Queen Elizabeth College (now part of King's College London). The duo were trying to test chlorinated sugars as chemical intermediates. On a late-summer day, Phadnis was told to test the powder. Phadnis thought that Hough asked him to ''taste'' it, so he did. He found the compound to be exceptionally sweet (the final formula was 600 times sweeter than sugar). They worked with Tate & Lyle for a year before settling down on the final formula.
It was first approved for use in Canada (marketed as Splenda) in 1991. Subsequent approvals came in Australia in 1993, in New Zealand in 1996, in the United States in 1998, and in the European Union in 2004. As of 2006, it had been approved in over 60 countries, including Brazil, China, India and Japan.
Front of yellow Splenda consumer packet.

Tate & Lyle manufactures sucralose at a plant in McIntosh, Alabama, with additional capacity under construction in Jurong, Singapore. It is manufactured by the selective chlorination of sucrose, in which three of the hydroxyl groups are replaced with chlorine atoms to produce 1,6-dichloro-1,6-dideoxy-β-D-fructo-furanosyl 4-chloro-4-deoxy-α-D-galactopyranoside or C12H19Cl3O8. It is used in products such as candy, breakfast bars and soft drinks. Sucralose mixed with maltodextrin and dextrose (both made from corn) as a filler is sold internationally by McNeil Nutritionals under the Splenda brand name. In the United States and Canada, this blend is increasingly found in restaurants, including McDonalds and Starbucks, in yellow packets, in contrast to the pink packets commonly used by saccharin sweeteners and the blue packets used by those containing aspartame; though in Canada yellow packets are also associated with the SugarTwin brand of cyclamate sweetener.

Packaging and storage


Most products that contain sucralose add fillers and additional sweetener to bring the product to the approximate volume and texture of an equivalent amount of sugar. This is because sucralose is nearly 600 times sweeter than sucrose (table sugar). Pure sucralose is sold in bulk, but not in quantities suitable for individual use. Pure dry sucralose undergoes some decomposition at elevated temperatures. When it is in solution or blended with maltodextrin it is slightly more stable.

Energy (caloric) content


Back of yellow Splenda consumer packet.

Though marketed in the U.S. as a “No calorie sweetener,†Splenda actually contains slightly more calories than the same mass of sugar (391 kcal per 100 g vs 390 kcal per 100 g for white granulated sugar).[4] When sucralose is added directly to commercial products, the filler is omitted and no calories are added.
Note too that although the “nutritional facts†label on Splenda’s retail packaging state that a single serving of 1 gram (1 teaspoon or 5 milliliters) contains zero calories, Splenda actually contains two calories per teaspoon.[5] Such labeling is appropriate in the U.S. because the FDA’s regulations permit a product to be labeled as “zero calories†if the “food contains less than 5 calories per reference amount customarily consumed and per labeled serving.â€[6] Because Splenda contains a relatively small amount of sucralose, little of which is metabolized, virtually all of Splenda’s caloric content derives from the highly fluffed dextrose or maltodextrin ''filler,'' or carrier, that gives Splenda its volume. Like other carbohydrates, dextrose and maltodextrin have 4 calories per gram.

Use in branded products


Sucralose can be found in more than 4,500 food and beverage products. Sucralose is used as a replacement of, or in combination with, other artificial sweeteners such as aspartame, acesulfame potassium or high-fructose corn syrup.
Sucralose is marketed in India by zydus cadila under the brand name 'Sugar free Natura'.

Cooking


Sucralose is the most heat-stable artificial sweetener available, allowing it to be used in many recipes without any use of sugar. Sucralose is available in granulated form so as to measure cup for cup like sugar.

Safety




Comparison of the chemical
structures of sucralose (top)
and sucrose (bottom).

Sucralose has been accepted by several national and international food safety regulatory bodies, including the U.S. Food and Drug Administration (FDA), Joint Food and Agriculture Organization/World Health Organization Expert Committee on Food Additives, The European Union's Scientific Committee on Food, Health Protection Branch of Health and Welfare Canada and Food Standards Australia-New Zealand (FSANZ). The acceptable daily intake for sucralose is 9 mg/kg of body weight (bw) per day.[7] (Note that Splenda is mostly Dextrose, a filler)
“In determining the safety of sucralose, the FDA reviewed data from more than 110 studies in humans and animals. Many of the studies were designed to identify possible toxic effects including carcinogenic, reproductive and neurological effects. No such effects were found, and FDA's approval is based on the finding that sucralose is safe for human consumption.â€[8] For example, McNeil Nutritional LLC studies submitted as part of its U.S. FDA Food Additive Petition 7A3987, indicated that "in the 2-year rodent bioassays... there was no evidence of carcinogenic activity for either sucralose or its hydrolysis products..."[9]
After FDA approval, a study published in the ''Journal of Head and Face Pain'' reported sucralose as a possible trigger for migraine patients.[10]. Another study published in the ''Journal of Mutation Research'' linked high doses (2000 mg per kg) of sucralose to DNA damage in mice.[11]
Concerns have been raised about the effect of sucralose on the thymus, an organ that is important to the immune system. A report from NICNAS cites two studies on rats, both of which found "a significant decrease in mean thymus weight" at a certain dose.[12] The sucralose dosages which caused the thymus gland effects referenced in the NICNAS report was 3000 mg/kg bw/day for 28 days. For an 80 kg (176 lb) human, this would mean a 28-day intake of 240 grams of sucralose, which is equivalent to more than 20,000 individual Splenda packets/day for approximately one month. The dose required to provoke ''any'' immunological response was 750 mg/kg bw/day,[13] or 60 grams of sucralose per day, which is more than 5,000 Splenda packets/day (there are 11.9 mg of sucralose in a 1g retail packet of Splenda). These and other studies were considered by regulators before concluding that sucralose was safe. However, because some ingested sucralose is broken down and absorbed by the body there is concern that chronic consumption may lead to thymus shrinkage or other side-effects.
Chlorine atoms are covalently bonded to the carbon atoms in the sucralose molecule, making it a chlorocarbon. Although many chlorocarbons are toxic, sucralose is not known to be toxic in small quantities and is extremely insoluble in fat, so it can not accumulate in fat like most chlorinated hydrocarbons. In addition sucralose does not break down or dechlorinate.[14]
The bulk of sucralose ingested does not leave the gastrointestinal tract and is directly excreted in the feces while 11-27% of it is absorbed. The amount that is absorbed from the GI tract is largely removed from the blood stream by the kidneys and excreted in the urine with 20-30% of the absorbed sucralose being metabolized. Sucralose is digestible by a number of microorganisms and is broken down once released into the environment.
Critics of sucralose often favor natural alternatives, including xylitol, maltitol, thaumatin, isomalt, and Stevia.
Splenda usually contains 95% dextrose (the "right-handed" isomer of glucose - see dextrorotation and chirality), which the body readily metabolizes. The safety information that many specialists and the media give to consumers is that Splenda is safe to ingest as a diabetic sugar substitute "free of problems".

Criticisms and controversy


Much of the concern over the safety of sucralose is not based on experimental evidence showing harm, but is rather based upon the absence of long-term health studies in humans proving its safety. The basis for demanding such strict burden of proof derives from the class of chemical to which sucralose belongs. The sucralose molecule is an organochlorides (chlorocarbon). Since some organochlorides are known to cause adverse health effects in extremely small concentrations (as little as the parts-per-billion level in drinking water), critics of sucralose feel the extra-high burden of proof is warranted.
However, it is well known numerous organochlorides are found in naturally occurring food sources such as seaweed.[15] In addition, polyvinyl chloride is a member of the organochloride family that has been commonly used to form pipes for conveying potable water for several decades. Given the ubiquity of these and other organochlorides and the absence of evidence of any harm caused by these organochlorides, chemists who work with organohalides argue that a higher burden of proof on safety for organochlorides as a class is inappropriate.
Certain members of the sweetener industry have claimed that the advertising of Splenda is deceptive. For example, the sugar industry has filed a formal complaint with the Federal Trade Commission. Taking issue with Splenda's advertising slogan, “made from sugar, so it tastes like sugar†the Sugar Association states that "Splenda is not a natural product. It is not cultivated or grown and it does not occur in nature." McNeil Nutritionals, the manufacturer of Splenda, has responded that its "advertising represents the products in an accurate and informative manner and complies with applicable advertising rules in the countries where Splenda brand products are marketed." The consumer advocacy group Citizens for Health has filed a petition with the FDA. They have asked the FDA to withdraw its approval of Splenda pending additional investigation of claimed side effects such as stomach pain and other digestion problems.[16] The U.S. Sugar Association has also started a web site where they put forward their criticism of sucralose.[17] The Sugar Association’s allegations revolve around three essential points:
# Sucralose is a chlorocarbon
# Up to 27% of sucralose that is ingested is absorbed into the body by the digestive system
# Long-term human studies with sucralose have not been performed.
Whole Foods Market, a U.S. based retailer of natural and organic foods, has a policy of not carrying products containing sucralose. The retailer’s statement regarding this decision made allegations revolving around five essential points:
# Sucralose is an artificial substance, some of which is absorbed by the body
# Pre-approval tests indicated a potential for toxicity
# Sucralose is a chlorinated compound (a chlorocarbon)
# Independent, controlled human studies had not been performed
# Long-term human studies with sucralose had not been performed.[18]
According to Food and Diet's website, numerous claims have been filed about possible side effect complaints by users of sucralose-containing products, including Diet Rite cola. Complaints and suspicions documented on the site of possible side effects of prolonged use of sucralose have included drug-like feelings of disorientation and confusion, headaches, depression, anxiety, diarrhea, vomiting, extreme fatigue, and more.[19]

Litigation between the makers of Splenda and Equal


In 2006 Merisant, the maker of Equal, filed suit against McNeil Nutritionals in federal court in Philadelphia alleging that Splenda's tagline "Made from sugar, so it tastes like sugar" is false and misleading and Merisant's website calls it an urban myth. McNeil argued during the trial that it had never deceived consumers or set out to deceive them, since the product did in fact start out with sugar. Merisant asked that McNeil be ordered to surrender profits and modify its advertising. The case ended with an agreement reached outside of court, with undisclosed settlement conditions.[20]
The lawsuit was the latest move in a long-simmering dispute. In 2004, Merisant filed a complaint with the Better Business Bureau regarding McNeil's advertising. McNeil alleged that Merisant's complaint was in retaliation for a ruling in federal court in Puerto Rico, which forced Merisant to stop packaging Equal in packages resembling Splenda's. McNeil filed suit in Puerto Rico seeking a ruling which would declare its advertising to not be misleading. Following Merisant's lawsuit in Philadelphia, McNeil agreed to a jury trial and to the dismissal of its lawsuit in Puerto Rico.[21]
In 2007, Merisant France won a significant victory in the Commercial Court of Paris against subsidiaries of McNeil Nutritionals LLC, the American company that markets Splenda.
The court awarded Merisant $54,000 in damages and ordered the defendants to cease advertising claims found to violate French consumer protection laws.The advertising claims found to violate French law and which McNeil must cease include: "Because it comes from sugar, sucralose tastes like sugar" and "With sucralose: Comes from sugar and tastes like sugar". The ruling orders McNeil to amend all advertising and promotions of Splenda that contain these misleading claims and to amend all packaging. The Court prohibited the distribution of any products under the trademark Splenda with unchanged packaging after a period of four months after serving this ruling.[22]

See also



Sugar substitute

Aspartame

Saccharin

Erythritol

References


1. ''Merck Index'', 11th Edition, '8854'.
2. Makers of Artificial Sweeteners Go to Court
3. WSJ Splenda
4. Splenda UK for the Splenda figure, the wikipedia article on sugar for the sugar figure.
5. Based upon 96 calories per cup and 48 teaspoons per cup.
6. Code of Federal Regulations, Title 21, Volume 2, Pg. 95 â€“ 101, Web version here.
7. Diabetes.ca
8. FDA Talk Paper T98-16
9. FDA Final Rule, Food Additives Permitted for Direct Addition to Food for Human Consumption; Sucralose
10. Journal of Head and Face Pain - September 2006
11. Journal of Mutation Research - August 2002
12. Report from NICNAS, The Australian Government regulator of industrial chemicals (PDF document)
13. USFDA Department of Health and Human Services, 1998
14. Daniel JW, Renwick AG, Roberts A, Sims J. The metabolic fate of sucralose in rats. ''Food Chem Tox.'' 2000;38(S2): S115-S121.
15. http://www.eurochlor.org/index.asp?page=97
16. "Sugar industry files complaint over Splenda: In letter to FTC, says ads are deceptive, sweetener not a natural product" (Reuters Nov. 2, 2006)
17. "The Truth About Splenda" website by the Sugar Association
18. Whole Foods Market (policy statement)
19. "Splenda" Food & Diet Website
20. "Artificial Sweetener Makers Reach Settlement on Slogan", New York Times, May 12, 2007 Online copy
21. WSJ Splenda
22. Splenda ad slogans banned in France, Food Navigator, May 14, 2007


★ Browning, Lynnley, Makers of Artificial Sweeteners Go to Court, New York Times Business section, April 6, 2007

★ Johnson,Avery, How Sweet It Isn't, Wall Street Journal Marketplace Section, April 6, 2007 p.B1

External links



Tate & Lyle's Official Website for Sucralose

U.S. FDA Code of Federal Regulations Database, Sucralose Section, As Amended Aug. 12, 1999

Truth about Splenda - campaign site run by the The Sugar Association, a group supporting the US sugar industry

Splenda truth - rebuttal site run by McNeil Nutritionals LLC, makers of Splenda
Science


Material Safety Data Sheet for Sucralose

Computational Chemistry Wiki
Press Releases


FDA press announcement - FDA report on its approval of Splenda

£97m Investment to Significantly Boost Splenda Sucralose Output (PDF) - describes new manufacturing plant in Singapore

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