Sucralose - Wikipedia, the free encyclopedia Page 1 of 6

Sucralose
From Wikipedia, the free encyclopedia
Sucralose[1]
Sucralose is an artificial sweetener that has the generic name Altern. In
the European Union, it is also known under the E number (additive code)
E955. Sucralose is sold under the trade name Splenda. Sucralose is
approximately 600 times sweeter than sucrose (table sugar),[2] 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.[3]
According to market research firm IRI, as reported in the Wall Street
Journal, Splenda sold $212 million in 2006 in the U.S. while Equal sold
$48.7 million.[4]

Contents
1,6-Dichloro-1,6-dideoxy-β-

1 History IUPAC
D-fructofuranosyl-4-chloro-

2 Packaging and storage name
4-deoxy-α-D-galactopyranoside

3 Energy (caloric) content 1',4,6'-Trichlorogalactosucrose

4 Use in branded products Other
Trichlorosucrose

5 Cooking names
E955

6 Safety Identifiers

6.1 Natural alternatives
56038-13-2

6.2 Organochlorides
CAS (http://www.emolecules.com/cgi-

7 Marketing controversy number bin/search?t=ss&q=56038-13-

8 See also 2&c=0&v=)

9 References
259-952-2

10 External links
EINECS (http://ecb.jrc.it/esis/index.php?

10.1 Science
number GENRE=ECNO&ENTREE=259-

10.2 Press Releases
952-2)
O[C@H]1[C@H](O)[C@@H](CCl)O
[C@]
History SMILES (CCl)1O[C@@H]2[C@H](O)
[C@@H]
Sucralose was discovered in 1976 by scientists from Tate & Lyle, (O)[C@@H](Cl)[C@@H](CO)O2
working with researchers Leslie Hough and Shashikant Phadnis at Queen Properties
Elizabeth College (now part of King's College London). The duo were Molecular C H Cl O
formula 12 19 3 8
trying to test chlorinated sugars as chemical intermediates. On a late-
summer day, Phadnis was told to test the powder. Phadnis thought that Molar
397.64 g/mol
Hough asked him to taste it, so he did. He found the compound to be mass
exceptionally sweet (the final formula was 600 times sweeter than sugar). Melting
point 130 °C
They worked with Tate & Lyle for a year before settling down on the
Except where noted otherwise, data are given for
final formula. materials in their standard state
(at 25 °C, 100 kPa)
It was first approved for use in Canada Infobox disclaimer and references
(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, United States, and Japan.

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Tate & Lyle manufactures sucralose at a plant in McIntosh, Alabama, with additional
Front of yellow Splenda capacity under construction in Jurong, Singapore. It is manufactured by the selective
consumer packet.
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. An alternative pathway is to selectively chlorinate raffinose.

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

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). However, since Splenda is one tenth as dense as sugar, a
given volume of Splenda has one tenth the energy of the same volume of sugar.[5] When
sucralose is added directly to commercial products, the filler is omitted and no energy is
added.

Note too that although the “nutritional facts” label on Splenda’s retail packaging states that
a single serving of 0.5 gram (1 teaspoon or 5 milliliters) contains zero calories, Splenda
actually contains two calories per teaspoon.[6] Note that the individual, tear-open packages
as shown at right are double-size, one-gram servings, which contain four calories. 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.”[7] Because Splenda contains a relatively Back of yellow Splenda
small amount of sucralose, little of which is metabolized, virtually all of Splenda’s caloric consumer packet.
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 for, or in
combination with, other artificial or natural 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.

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Cooking
Sucralose is a highly heat-stable artificial sweetener, allowing it to be used in many recipes without any use of sugar.
Sucralose is available in a granulated form that allows for cup-for-cup substitution with sugar.

Safety
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). According to the Canadian Diabetes Association, one can consume 15
mg/kg/day of Sucralose "on a daily basis over a ... lifetime without any adverse effects".
[8] For a 150 lb person, 15 mg/kg is about 1000 mg, equivalent to about 75 packets of
Splenda or the sweetness of 612 gm or 2500 kcal of sugar.

“In determining the safety of sucralose, the FDA reviewed data from more than 110 Comparison of the chemical
studies in humans and animals. Many of the studies were designed to identify possible structures of sucralose (top)
toxic effects including carcinogenic, reproductive and neurological effects. No such and sucrose (bottom).
effects were found, and FDA's approval is based on the finding that sucralose is safe for
human consumption.”[9] 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...."[10]
After FDA approval, a study published in the Journal of Head and Face Pain reported sucralose as a possible trigger
for migraine patients.[11] Another study published in the Journal of Mutation Research linked high doses (2000 mg per
kg) of sucralose to DNA damage in mice.[12]
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.[13] 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,[14] 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.

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.[2] 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.[2] Sucralose is digestible
by a number of microorganisms and is broken down once released into the environment.

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".

Natural alternatives

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Critics of sucralose often favor natural alternatives, including xylitol, maltitol, thaumatin, isomalt, and Stevia.
However, those substances raise other health concerns, and natural products generally do not undergo controlled trials
before being allowed in food.

Organochlorides

The basis for concern about the safety of sucralose derives from the class of chemical to which it belongs. The
sucralose molecule is an organochloride (or chlorocarbon). Since some organochlorides are known to cause adverse
health effects in extremely small concentrations, critics of sucralose feel the extra-high burden of proof is warranted.
Although some chlorocarbons are toxic, sucralose is not known to be toxic in small quantities and is extremely
insoluble in fat; it can not accumulate in fat like chlorinated hydrocarbons. In addition, sucralose does not break down
or dechlorinate.[15]

In contrast to these concerns, many organochlorides occur naturally in food sources such as seaweed.[16] 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.

Marketing controversy
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.[17]
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.[4]

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.[18]
A Sugar Association complaint to the Federal Trade Commission points out 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."[19] The U.S. Sugar
Association has also started a web site where they put forward their criticism of sucralose.[20]

See also

Sugar substitute

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Aspartame

Saccharin

Erythritol

References
1. ^ Merck Index, 11th Edition, 8854.
2. ^ a b c Michael A. Friedman, Lead Deputy Commissioner for the FDA, Food Additives Permitted for Direct Addition to Food
for Human Consumption; Sucralose (http://www.cfsan.fda.gov/~lrd/fr980403.html) Federal Register: 21 CFR Part 172,
Docket No. 87F-0086, April 3, 1998
3. ^ Browning, Lynnley, "Makers of Artificial Sweeteners Go to Court", New York Times Business section, April 6, 2007
4. ^ a b Johnson,Avery, "How Sweet It Isn't", Wall Street Journal Marketplace Section, April 6, 2007 p.B1
5. ^ Splenda UK (http://www.splenda.co.uk/about_splenda/granular.html) for the Splenda figure, the wikipedia article on sugar
for the sugar figure.
6. ^ Based upon 96 calories per cup and 48 teaspoons per cup.
7. ^ Code of Federal Regulations, Title 21, Volume 2, Pg. 95 – 101, Web version here. (http://www.cfsan.fda.gov/~lrd/cf101-
60.html)
8. ^ Diabetes.ca (http://www.diabetes.ca/cpg2003/chapters.aspx?table1acceptabledailyintakeofsweeteners.htm)
9. ^ FDA Talk Paper T98-16 (http://vm.cfsan.fda.gov/~lrd/tpsucral.html)
10. ^ FDA Final Rule, Food Additives Permitted for Direct Addition to Food for Human Consumption; Sucralose
(http://www.cfsan.fda.gov/~lrd/fr980403.html)
11. ^ Journal of Head and Face Pain - September 2006 (http://www.blackwell-synergy.com/doi/abs/10.1111/j.1526-
4610.2006.00543_1.x)
12. ^ Journal of Mutation Research - August 2002 (http://www.ncbi.nlm.nih.gov/sites/entrez?
cmd=Retrieve&db=PubMed&list_uids=12160896&dopt=Abstract)
13. ^ Report from NICNAS, The Australian Government regulator of industrial chemicals (PDF document)
(http://www.nicnas.gov.au/publications/car/new/NA/NAFULLR/NA0900FR/NA944FR.pdf)
14. ^ USFDA Department of Health and Human Services, 1998
15. ^ Daniel JW, Renwick AG, Roberts A, Sims J. The metabolic fate of sucralose in rats. Food Chem Tox. 2000;38(S2): S115-
S121.
16. ^ http://www.eurochlor.org/index.asp?page=97
17. ^ "Artificial Sweetener Makers Reach Settlement on Slogan", New York Times, May 12, 2007 Online copy
(http://www.nytimes.com/2007/05/12/business/media/12splenda.html?
ex=1336622400&en=8f48609f972bc31d&ei=5088&partner=rssnyt&emc=rss)
18. ^ Splenda ad slogans banned in France, Food Navigator, May 14, 2007 (http://www.foodnavigator.com/news/ng.asp?
n=76495-mcneil-nutritionals-merisant-splenda-sucralose)
19. ^ "Sugar industry files complaint over Splenda: In letter to FTC, says ads are deceptive, sweetener not a natural product
(http://www.msnbc.msn.com/id/15533454/)" (Reuters Nov. 2, 2006)
20. ^ "The Truth About Splenda (http://www.truthaboutsplenda.com/)" website by the Sugar Association

External links

Tate & Lyle's Official Website for Sucralose (http://www.sucralose.com/)

U.S. FDA Code of Federal Regulations Database, Sucralose Section, As Amended Aug. 12, 1999
(http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=172.831)

Splenda truth (http://splendatruth.com/) - rebuttal site run by McNeil Nutritionals LLC, makers of Splenda

Science

Material Safety Data Sheet for Sucralose (http://www.innosweet.de/_downloads/MSDS_Sucralose_v1.00.pdf)

Computational Chemistry Wiki (http://www.compchemwiki.org/index.php?title=Sucralose)

Press Releases

FDA press announcement (http://vm.cfsan.fda.gov/~lrd/tpsucral.html) - FDA report on its approval of Splenda

£97m Investment to Significantly Boost Splenda Sucralose Output
(http://www.tateandlyle.co.uk/NR/rdonlyres/eqidug7djqvedi55d3sg2id2itl3plmspar755kbkmsm6gehafy5ypszyitya

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(PDF) - describes new manufacturing plant in Singapore

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