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Sucralose[1]
IUPAC name[hide]
1,6-Dichloro-1,6-dideoxy-β-D-fructofuranosyl-4-chloro-4-deoxy-α-D-galactopyranoside
1',4,6'-Trichlorogalactosucrose / Trichlorosucrose E955
Identifiers
CAS number 56038-13-2
ChemSpider 64561
EC number 259-952-2
[show]
SMILES
Properties
Molecular formula C12H19Cl3O8
Molar mass 397.64 g/mol
Melting point 125 °C, 398 K, 257 °F
Solubility in water 283 g/L (20 °C)
Except where noted otherwise, data are given for materials in their
standard state (at 25 °C, 100 kPa)
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).[4] On a late-summer day, Phadnis was told to test the powder.
Phadnis thought that Hough asked him to taste it, so he did.[4] He found the compound to
be exceptionally sweet, as sucralose is 600 times as sweet as sucrose.
Sucralose was first approved for use in Canada 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.[5]
In May 2008, Fusion Nutraceuticals launched a generic product to the market, using Tate
& Lyle patents.
Production
Tate & Lyle manufactures sucralose at a plant in McIntosh, Alabama, with additional
capacity in Jurong, Singapore. It is manufactured by the selective chlorination of sucrose
(table sugar), which converts three of the hydroxyl groups to chlorides. The selective
chlorination is achieved by selective protection of the primary alcohol groups followed
by acetylation and then deprotection of the primary alcohol groups. Following an induced
acetyl migration on one of the hydroxyl groups, the partially acetylated sugar is then
chlorinated with a chlorinating agent such as phosphorus oxychloride, followed by
removal of the acetyl groups to give sucralose.[6]
Product Uses
Sucralose can be found in more than 4,500 food and beverage products. It is used because
it is a no-calorie sweetener, does not promote dental cavities,[7] and is safe for
consumption by diabetics.[8] 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 drinks. 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 McDonald's, Tim Hortons and Starbucks, in
yellow packets, in contrast to the blue packets commonly used by aspartame and the pink
packets used by those containing saccharin sweeteners; though in Canada yellow packets
are also associated with the SugarTwin brand of cyclamate sweetener.
Cooking
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.[9] Pure dry sucralose
undergoes some decomposition at elevated temperatures. When it is in solution or
blended with maltodextrin, it is slightly more stable.
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).
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). Sucralose is one of two artificial sweeteners ranked as "safe" by the consumer
advocacy group Center for Science in the Public Interest. The other is Neotame.[10][11][12]
According to the Canadian Diabetes Association, the amount of sucralose that can be
consumed on a daily basis over a person’s lifetime without any adverse effects is
9 mg/kg/day.[13][14]
"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." 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..."[15]
Safety studies
Results from over 100 animal and clinical studies in the FDA approval process
unanimously indicated a lack of risk associated with sucralose intake.[4][16][17][18]
However, some adverse effects were seen at doses that significantly exceeded the
estimated daily intake (EDI), which is 1.1 mg/kg/day.[19] When the EDI is compared to
the intake at which adverse effects are seen, known as the highest no adverse effects limit
(HNEL), at 1500 mg/kg/day,[19] there is a large margin of safety. The bulk of sucralose
ingested is not absorbed by the gastrointestinal (GI) 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 eliminated in the urine with
20-30% of the absorbed sucralose being metabolized.[2]
Thymus
Some concern has been raised about the effect of sucralose on the thymus. A report from
the Australian National Industrial Chemicals Notification and Assessment Scheme
(NICNAS) cites two studies on rats, both of which found "a significant decrease in mean
thymus weight" at high doses.[20] The sucralose dose which caused the effects was
3000 mg/kg/day for 28 days. For a 150 lb (68.2 kg) human, this would mean an intake of
nearly 205 grams of sucralose a day, which is equivalent to more than 17,200 individual
Splenda packets/day for approximately one month. The dose required to provoke any
immunological response was 750 mg/kg/day,[21] or 51 grams of sucralose per day, which
is nearly 4,300 Splenda packets/day. After evaluation of these data and other
toxicological findings, the NICNAS report concluded that sucralose does not pose a
hazard to public health.[20]
Environmental effects
Chlorinated substances
Allergic reactions to sucralose have not been documented, but individuals sensitive to
either maltodextrin or dextrose should consult a physician about using any sweeteners
containing these fillers.
References
External links