Sucralose
48463
224869885
2008-07-10T19:49:12Z
Vuo
143648
/* Production */
{{Chembox new
| Reference=<ref>''Merck Index'', 11th Edition, '''8854'''.</ref>
| ImageFile = Sucralose2.svg
| ImageFile1 = Sucralose-3D-balls.png
| IUPACName = 1,6-Dichloro-1,6-dideoxy-β-<br /><small>D</small>-fructofuranosyl-4-chloro-<br />4-deoxy-α-<small>D</small>-galactopyranoside
| OtherNames = 1',4,6'-Trichlorogalactosucrose<br />Trichlorosucrose<br>E955
| Section1 = {{Chembox Identifiers
| CASNo = 56038-13-2
| EINECS = 259-952-2
| SMILES = O[C@H]1[C@H](O)[C@@H](CCl)O[C@]<br />(CCl)1O[C@@H]2[C@H](O)[C@@H]<br />(O)[C@@H](Cl)[C@@H](CO)O2
}}
| Section2 = {{Chembox Properties
| Formula = C<sub>12</sub>H<sub>19</sub>Cl<sub>3</sub>O<sub>8</sub>
| MolarMass = 397.64 g/mol
| MeltingPt = 130 °C
}}
}}
'''Sucralose''' is an [[sugar substitute|artificial sweetener]] originally sold under the trade name '''Splenda''', but now also supplied by a variety of manufacturers under various brand names. In the European Union, it is also known under the [[E number]] (additive code) '''E955'''. Sucralose is approximately 600 times as [[Sweetness|sweet]] as [[sucrose]] (table sugar),<ref name=Friedman>Michael A. Friedman, Lead Deputy Commissioner for the FDA, [http://www.cfsan.fda.gov/~lrd/fr980403.html 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</ref> 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. Sucralose also does not promote tooth decay.<ref>Facts About Sucralose, American Dietetic Association, 2006.</ref> Since its introduction in 1999, sucralose has overtaken [[Equal (sweetener)|Equal]] in the $1.5 billion artificial sweetener market, holding a 62% market share.<ref>Browning, Lynnley, "Makers of Artificial Sweeteners Go to Court", ''New York Times'' Business section, April 6, 2007 </ref> 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.<ref name="WSJ">Johnson,Avery, "How Sweet It Isn't", ''[[Wall Street Journal]]'', Marketplace Section, April 6, 2007 p.B1</ref>
==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]]).<ref name="kon">[http://www.kon.org/urc/frank.html Sucralose: An Overview], by Genevieve Frank, Penn State University</ref> 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.<ref name="kon"/> He found the compound to be exceptionally sweet (the final formula was 600 times as sweet as sugar). They worked with [[Tate & Lyle]] for a year before settling down on the final formula.
[[Image:SplendaFront.JPG|thumb|150px|left|Front of yellow Splenda consumer packet.]]
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 2008, it had been approved in over 80 countries, including [[Mexico]], [[Brazil]], [[China]], [[India]] and [[Japan]].<ref>[http://www.splenda.com/page.jhtml?id=splenda/newspromotions/press/safety.inc Splenda No Calorie Sweetener Fact Sheet], splenda.com</ref>
== Production ==
[[Tate & Lyle]] manufactures sucralose at a plant in [[McIntosh, Alabama]], with additional capacity under construction in [[Jurong|Jurong, Singapore]]. It is manufactured by the selective chlorination of [[sucrose]] (table sugar), in which three of the [[hydroxyl group]]s are replaced with [[chlorine]] atoms to produce sucralose. An alternative pathway is to selectively chlorinate [[raffinose]]. In May 2008, [[Fusion Nutraceuticals]] launched a competing brand, called SucraPlus, to Tate and Lyle's sucralose. The sucralose is manufactured by Alkem in India, using the same technology as described in Tate & Lyle's now-expired patents.
== Use ==
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 used in products such as [[candy]], [[breakfast]] bars and [[soft drink]]s. It is also used in canned fruits wherein water and sucralose take the place of much higher calorie corn syrup based additives. Sucralose mixed with [[maltodextrin]] or [[dextrose]] (both made from corn) as bulking agents 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 as sweet as [[sucrose]] (table sugar). Pure sucralose is sold in bulk, but not in quantities suitable for individual use, although some highly concentrated sucralose-water blends are available online, using 1/4 tsp per 1 cup of sweetness or roughly 1 part sucralose to 2 parts water.<ref>Sweetzfree is a clear liquid syrup base, highly concentrated, and made from 100% pure Sucralose in a purified water concentrate.</ref> 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 products that also include bulking agents contain about 86% of the calories as the same mass of [[sugar]] (331 calories per 100 g vs. 387 calories per 100 g for sugar).<ref>[[United States Department of Agriculture|USDA’s]] [http://www.breadwithoutborders.com/calorie.htm Nutrient Data Laboratory]</ref> However, since Splenda is about 14.5% as dense as sugar, a given volume of Splenda has 12.4% the energy of the same volume of sugar.<ref>Assuming 96 calories per cup per McNeil Nutritionals, LLC., 331 calories per 100 g per USDA’s [http://www.breadwithoutborders.com/calorie.htm Nutrient Data Laboratory], and assuming 1 cup of sugar has a mass of 200 g and has 774 calories (also per USDA).</ref> When sucralose is added to commercial products such as diet drinks, the bulking agent is not present and no caloric energy is added.
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 1.66 calories per teaspoon.<ref>Based on 331 calories per 100 grams and a half-gram serving.</ref> The individual, tear-open packages are 1 gram servings which therefore contain 3.31 calories. Such labeling is appropriate in the U.S. because the [[Food and Drug Administration|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.”<ref>Code of Federal Regulations, Title 21, Volume 2, Pg. 95 – 101, Web version [http://www.cfsan.fda.gov/~lrd/cf101-60.html here.]</ref> 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 [[Dextrin|maltodextrin]] bulking agents that give Splenda its volume. Like other [[carbohydrate]]s, dextrose and maltodextrin have 3.75 calories per gram.<!--EDITORS: Please note that with regard to “dextrose and/or maltodextrin” filler, McNeil Nutritionals, LLC has different formulations for Splenda in different packaging. Some are a dextrose/maltodextrin blend, and others are entirely maltodextrin.-->
==Cooking==
{{Expand-section|date=November 2007}}
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 volume-for-volume substitution with sugar. This mix of sucralose and fillers rapidly dissolves in liquids. However, while it provides volume-for-volume sweetness, the texture may be noticeably different.
Some claim that one can offset the caloric load of traditional Southern [[sweet tea]] by substituting Splenda for 1/3 of the usually prescribed sugar ingredient thus adding a 2:1 sugar-sucralose mixture that preserves the integrity of traditional recipes.
==Safety==
{{Double image stack|right|sucrose2.png|sucralose2.png|150|Comparison of the chemical structures of sucrose (top) and sucralose (bottom).}}
Sucralose has been accepted by several national and international food safety regulatory bodies, including the [[Food and Drug Administration|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). Sucralose is the only artificial sweetener ranked as "safe" by the consumer advocacy group [[Center for Science in the Public Interest]].<ref>''[http://www.cspinet.org/new/pdf/additives.pdf Nutrition Action Health Letter]'', [[Center for Science in the Public Interest]], May 2008</ref><ref>[http://www.cspinet.org/new/200804291.html Which additives are safe? Which aren't?], [[Center for Science in the Public Interest]]</ref> 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".<ref>[http://www.diabetes.ca/cpg2003/chapters.aspx?table1acceptabledailyintakeofsweeteners.htm Diabetes.ca Acceptable daily intake of sweeteners]</ref> For a 150 lb person, 15 mg/kg is about 1 g, equivalent to about 75 packets of Splenda or the sweetness of 612 gm or 2500 kcal of sugar.
<!-- Calculation is as follows using GNU units (technically this is original research):
(15 mg/kg) * (150 lb) = 1.0205828 gm
(15 mg/kg) * (150 lb) / (8 gm / 600) = 76.543712
(15 mg/kg) * (150 lb) * 600 = 612.3497 gm
(15 mg/kg) * (150 lb) * 600 * (4 kcal/gm) = 2449.3988 kcal -->
“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.”<ref>[http://vm.cfsan.fda.gov/~lrd/tpsucral.html FDA Talk Paper T98-16]</ref> 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...."<ref>[http://www.cfsan.fda.gov/~lrd/fr980403.html FDA Final Rule, Food Additives Permitted for Direct Addition to Food for Human Consumption; Sucralose]</ref>
After FDA approval, a study published in the ''Journal of Head and Face Pain'' reported sucralose as a possible trigger for migraine patients.<ref>[http://www.blackwell-synergy.com/doi/abs/10.1111/j.1526-4610.2006.00543_1.x Journal of Head and Face Pain - September 2006]</ref> Another study published in the ''Journal of Mutation Research'' linked high doses (2 g per kg; equal to 10,000 packets per day for the 150 lb person in the above example) of sucralose to DNA damage in mice.<ref>[http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=12160896&dopt=Abstract Journal of Mutation Research - August 2002]</ref>
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.<ref>[http://www.nicnas.gov.au/publications/car/new/NA/NAFULLR/NA0900FR/NA944FR.pdf Report from NICNAS, The Australian Government regulator of industrial chemicals (PDF document)]</ref> 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,<ref>USFDA Department of Health and Human Services, 1998</ref> 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.
There have been anecdotal reports of "allergic" reactions and other adverse reactions to Splenda. <ref>[http://www.belicove.com/archives/beliblog/000651.html "Splenda allergy"], Belicove.com</ref><ref>[http://www.issplendasafe.com/ Is Splenda safe?]</ref>
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.<ref name=Friedman/> 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.<ref Name=Friedman/> According to one study, sucralose is digestible by a number of microorganisms and is broken down once released into the environment.<ref>Biodegradation of sucralose in samples of natural environments. Labare, Michael P.; Alexander, Martin. ''Environmental Toxicology and Chemistry'' (1993), 12(5), 797-804.</ref> However, measurements by the Swedish Environmental Research Institute have shown that [[wastewater treatment]] has little effect on sucralose, which is present in wastewater effluents at levels of several μg/l. <ref>[http://www.naturvardsverket.se/upload/02_tillstandet_i_miljon/Milj%C3%B6gifter/sukralos_ivl_08.pdf Measurements of Sucralose in the Swedish Screening Program 2007, Part I; Sucralose in surface waters and STP samples<!-- Bot generated title -->]</ref>There are no known eco-toxicological effects at such levels, but the [[Swedish Environmental Protection Agency]] warns that there may be a continuous increase in levels if the compound is only slowly degraded in nature.<ref>[http://www.naturvardsverket.se/sv/Tillstandet-i-miljon/Miljogifter/Organiska-miljogifter/Sa-sprids-miljogifter-i-miljon/Sotningsmedel-sprids-till-miljon/ Sötningsmedel sprids till miljön - Naturvårdsverket<!-- Bot generated title -->]</ref>
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.<ref>[http://www.ific.org/publications/brochures/sucralosebroch.cfm Everything You Need to Know About Sucralose], [[International Food Information Council]]</ref>
===Natural alternatives===
Critics of sucralose often favor natural alternatives, including [[xylitol]], [[maltitol]], [[thaumatin]], [[isomalt]] and [[stevia]]. However, those substances are - like most artificial sweeteners - partially accused of having other health concerns,<ref>{{cite journal |author=Lynch BS, Tischler AS, Capen C, Munro IC, McGirr LM, McClain RM |title=Low digestible carbohydrates (polyols and lactose): significance of adrenal medullary proliferative lesions in the rat |journal=Regul. Toxicol. Pharmacol. |volume=23 |issue=3 |pages=256–97 |year=1996 |pmid=8812969 |doi=10.1006/rtph.1996.0055}}</ref><ref>{{cite journal |author=Nunes AP, Ferreira-Machado SC, Nunes RM, Dantas FJ, De Mattos JC, Caldeira-de-Araújo A |title=Analysis of genotoxic potentiality of stevioside by comet assay |journal=Food Chem. Toxicol. |volume=45 |issue=4 |pages=662–6 |year=2007 |doi=10.1016/j.fct.2006.10.015}}</ref><ref>{{cite journal |author=Canimoğlu S, Rencüzoğullari E |title=The cytogenetic effects of food sweetener maltitol in human peripheral lymphocytes |journal=Drug Chem Toxicol |volume=29 |issue=3 |pages=269–78 |year=2006 | doi = 10.1080/01480540600651600 <!--Retrieved from CrossRef by DOI bot-->}}</ref> and natural products generally do not undergo controlled trials before being allowed in food.<ref>[http://www.fda.gov/opacom/laws/dshea.html Dietary Supplement Health and Education Act of 1994], Public Law 103-417, 103rd Congress</ref>
===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 [[hydrocarbon]]s. In addition, sucralose does not break down or dechlorinate.<ref>Daniel JW, Renwick AG, Roberts A, Sims J. The metabolic fate of sucralose in rats. ''Food Chem Tox.'' 2000;38(S2): S115-S121.</ref>
In contrast to these concerns, many organochlorides occur naturally in food sources such as seaweed.<ref>[http://www.eurochlor.org/index.asp?page=97 Natural organochlorines in living organisms: chlorinated compounds, biosynthesized<!-- Bot generated title -->]</ref>
===Effect on weight gain===
Research where rats were given [[yogurt]] sweetened with either sugar or [[saccharin]] found that the rats given saccharin gained more weight, because they ate more afterwards, presumably due to compensatory effects. It is hypothesized that this effect would apply to all non-nutritive sweeteners, and would also be seen in humans.
<ref>[http://www.sciencedaily.com/releases/2008/02/080210183902.htm Artificial Sweeteners Linked To Weight Gain], sciencedaily.com, Feb 11, 2008</ref>
==Marketing controversy==
In 2006 [[Merisant]], the maker of [[Equal (sweetener)|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.<ref>[http://www.nytimes.com/2007/05/12/business/media/12splenda.html?ex=1336622400&en=8f48609f972bc31d&ei=5088&partner=rssnyt&emc=rss Artificial Sweetener Makers Reach Settlement on Slogan], ''[[New York Times]]'', May 12, 2007</ref> 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.<ref name="WSJ"/>
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.<ref>[http://www.foodnavigator.com/news/ng.asp?n=76495-mcneil-nutritionals-merisant-splenda-sucralose Splenda ad slogans banned in France, Food Navigator, May 14, 2007]</ref>
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."<ref>[http://www.truthaboutsplenda.com/news/11-02-06-splenda_ads_condemned.html Splenda Ads Condemmed as Misleading to Consumers by International Advertising Boards, Sugar Farmers and Processors], Sugar Association Press Release, November 2, 2006</ref> [[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."<ref>[http://www.msnbc.msn.com/id/15533454/ Sugar industry files complaint over Splenda], [[Reuters]] article at MSNBC.com, Nov. 2, 2006</ref> The U.S. Sugar Association has also started a web site where they put forward their criticism of sucralose.<ref>"[http://www.truthaboutsplenda.com/ The Truth About Splenda]" website by the Sugar Association</ref>
== See also ==
* [[Sugar substitute]]
* [[Aspartame]]
* [[Saccharin]]
* [[Erythritol]]
* [[Acesulfame potassium]]
* [[Cyclamate]]
== References ==
{{reflist|2}}
==External links==
*[http://www.sucralose.com/ Tate & Lyle's Official Website for Sucralose]
*[http://www.accessdata.fda.gov/scripts/cdrh/cfdocs/cfcfr/CFRSearch.cfm?fr=172.831 U.S. FDA Code of Federal Regulations Database, Sucralose Section, As Amended Aug. 12, 1999]
*[http://splendatruth.com/ Splenda truth] - rebuttal site run by McNeil Nutritionals LLC, makers of Splenda
===Science===
*[http://www.dulcettetech.com/Sucralose/MSDS%20Sucralose.pdf Material Safety Data Sheet for Sucralose]
*[http://www.compchemwiki.org/index.php?title=Sucralose Computational Chemistry Wiki]
===Press Releases===
*[http://vm.cfsan.fda.gov/~lrd/tpsucral.html FDA press announcement] - FDA report on its approval of Splenda
*[http://www.tateandlyle.co.uk/NR/rdonlyres/eqidug7djqvedi55d3sg2id2itl3plmspar755kbkmsm6gehafy5ypszyityaqo4rdsrdtimt5m7lanqznkocsufxla/SingaporePressRelease.pdf £97m Investment to Significantly Boost Splenda Sucralose Output] ([[PDF]]) - describes new manufacturing plant in [[Singapore]]
{{E number infobox 950-969}}
[[Category:Sweeteners]]
[[Category:Disaccharides]]
[[Category:Food additives]]
[[Category:Organochlorides]]
[[da:Sukralose]]
[[de:Sucralose]]
[[es:Sucralosa]]
[[fr:Sucralose]]
[[gl:Sucralosa]]
[[it:Sucralosio]]
[[he:סוכרלוז]]
[[nl:Sucralose]]
[[ja:スクラロース]]
[[no:Sukralose]]
[[pl:Sukraloza]]
[[fi:Sukraloosi]]
[[sv:Sukralos]]
[[zh:三氯蔗糖]]