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| Names | |
|---|---|
| IUPAC name 1,6-Dichloro-1,6-dideoxy-β-D-fructofuranosyl 4-chloro-4-deoxy-α-D-galactopyranoside | |
| Systematic IUPAC name (2R,3R,4R,5R,6R)-2-{[(2R,3S,4S,5S)-2,5-Bis(chloromethyl)-3,4-dihydroxyoxolan-2-yl]oxy}-5-chloro-6-(hydroxymethyl)oxane-3,4-diol | |
Other names
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| Identifiers | |
3D model (JSmol) | |
| ChEBI | |
| ChemSpider |
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| ECHA InfoCard | 100.054.484 |
| EC Number |
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| E number | E955(glazing agents, ...) |
| KEGG |
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| UNII | |
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| Properties | |
| C12H19Cl3O8 | |
| Molar mass | 397.63 g·mol−1 |
| Appearance | Off-white to white powder |
| Odor | Odorless |
| Density | 1.69 g/cm3 |
| Melting point | 125 °C (257 °F; 398 K) |
| 283 g/L (20 °C) | |
| Acidity (pKa) | 12.52±0.70 |
| Hazards | |
| NFPA 704 (fire diamond) | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Sucralose is an artificialsweetener andsugar substitute. In theEuropean Union, it is also known under theE numberE955. It is produced bychlorination ofsucrose, selectivelyreplacing three of thehydroxy groups—in the C1 and C6 positions of thefructose portion and the C4 position of theglucose portion—to give a1,6-dichloro-1,6-dideoxyfructose–4-chloro-4-deoxygalactosedisaccharide. Sucralose is about 600 timessweeter than sucrose (table sugar),[2][3] 3 times as sweet as bothaspartame andacesulfame potassium, and 2 times as sweet assodium saccharin.[2]
The commercial success of sucralose-based products stems from its favorable comparison to other low-calorie sweeteners in terms of taste, stability, and safety.[2][4]
Sucralose is used in many food and beverage products because it is a non-nutritive sweetener (14 kilojoules [3.3 kcal] per typical one-gram serving),[5] does not promotedental cavities,[6] is safe for consumption bydiabetics and nondiabetics[7] and does not affectinsulin levels.[8] The powdered form of the sucralose-based sweetener productSplenda contains thebulking agents –dextrose andmaltodextrin. Sucralose content is about 1.1% and remainder is bulking agents.[9][10]
Sucralose is used as a replacement for (or in combination with) other artificial or natural sweeteners such asaspartame,acesulfame potassium orhigh-fructose corn syrup. It is used in products such ascandy,breakfast bars,coffee pods, andsoft drinks. It is also used incanned fruits wherein water and sucralose take the place of much higher-energycorn syrup-based additives. Sucralose mixed with dextrose or maltodextrin (both made from corn) as bulking agents is sold internationally byMcNeil Nutritionals under the Splenda brand name.[9]
This mixture of granulated sucralose includes fillers, all of which rapidly dissolve in water. Sucralose is nothygroscopic when humidity is below 80%, which can lead to baked goods that are noticeably drier and manifest a less dense texture than those made with sucrose.[11]
Sucralose has been accepted as safe by several food safety regulatory bodies worldwide, including the U.S.Food and Drug Administration (FDA), theJoint FAO/WHO Expert Committee Report on Food Additives, theEuropean Union'sScientific Committee on Food, Health Protection Branch ofHealth and Welfare Canada, andFood Standards Australia New Zealand.
At normal baking temperatures, sucralose is mostly heat-stable, indicating that it retains its sweetness and is suitable as a sugar substitute for use in baked goods.[2] However, there is concern about the possible formation ofdioxins when sucralose is heated.[12] Especially when heating sucralose above 120 °C, chlorinated organic compounds such aspolychlorinated dibenzo-p-dioxins (PCDD),polychlorinated dibenzofurans (PCDF), orchloropropanol might[quantify] form.[13][needs update]
Various assessments have reported different amounts of maximumacceptable daily intake (ADI), usually measured as mg per kg of body weight. According to theCanadian Diabetes Association, the amount of sucralose that can be consumed over a person's lifetime without any adverse effects is 9 milligrams per kilogram of body weight per day.[14][15] The FDA approval process indicated that consuming sucralose in typical amounts as a sweetener was safe.[15][16] Theintake at which adverse effects are seen is 1500 mg per kilogram of body weight per day,[16] providing a large margin of safety compared to the estimated daily intake. TheEuropean Food Safety Authority (EFSA) proposed an ADI of 5 mg per kilogram of body weight, while the FDA established it as 15 mg per kilogram of body weight, that is, 350–1050 mg per day for a person of 70 kg.[15]
Most ingested sucralose is directly excreted in thefeces, while about 11–27% is absorbed by thegastrointestinal tract (gut).[15][16] The amount absorbed from the gut is largely removed from theblood by thekidneys and eliminated viaurine, with 20–30% of absorbed sucralose being metabolized.[15][16]
In reviewing a 1987 food additive petition by McNeil Nutritionals, the FDA stated that "in the 2-year rodentbioassays ... there was no evidence ofcarcinogenic activity for either sucralose or its hydrolysis products".[16][17]
In 2023, the World Health Organization (WHO) conditionally recommended against the use of non-sugar sweeteners, including sucralose, for weight management or preventive care in the general population (except for diabetics).[18] The WHO recommended reducing the intake of sugar, highly processed food and sweetened beverages, and replacing them with minimally processed unsweetened beverages and foods, such as fruits.[18]
As of 2024[update], reviews of numerous safety and toxicology studies on sucralose concluded that it is nottoxic orcarcinogenic, even at levels of daily consumption much larger than those typically used.[2][15][16]
Sucralose was discovered in 1975 by scientists fromTate & Lyle, working with researchers Leslie Hough and Shashikant Phadnis atQueen Elizabeth College (now part ofKing's College London).[19] While researching novel uses ofsucrose and its synthetic derivatives, mixingsulfuryl chloride with sugar, Phadnis was told to "test" a chlorinated sugar compound. According to an anecdotal account, Phadnis thought Hough asked him to "taste" it, so he did and found the compound to be exceptionally sweet.[20][21]
Tate & Lyle patented the substance in 1976; as of 2008, the only remaining patents concerned specific manufacturing processes.[22]
ADuke University animal study funded by theSugar Association[23] found evidence that doses of Splenda (containing ~1% sucralose and ~99% maltodextrin by weight) between 100 and 1000 mg/kg BW/day, containing sucralose at 1.1 to 11 mg/kg BW/day, fed to rats reducedgut microbiota, increased the pH level in the intestines, contributed to increases in body weight, and increased levels ofP-glycoprotein (P-gp).[24] These effects have not been reported in humans.[3] An expert panel, including scientists from Duke University,Rutgers University,New York Medical College,Harvard School of Public Health, andColumbia University reported inRegulatory Toxicology and Pharmacology that the Duke study was "not scientifically rigorous and is deficient in several critical areas that preclude reliable interpretation of the study results".[25]
Sucralose was first approved for use inCanada in 1991. Subsequent approvals came inAustralia in 1993, inNew Zealand in 1996, in theUnited States in 1998, and in theEuropean Union in 2004. By 2008, it had been approved in over 80 countries, includingMexico,Brazil,China,India, andJapan.[26] In 2006, the FDA amended the regulations for foods to include sucralose as a "non-nutritive sweetener" in food.[27] In May 2008, Fusion Nutraceuticals launched a generic product to the market, using Tate & Lyle patents.
In April 2015,PepsiCo announced that it would be moving from aspartame to sucralose for most of its diet drinks in the U.S.[28] due to sales ofDiet Pepsi falling by more than 5% in the U.S. The company stated that its decision was a commercial one, responding to consumer preferences.
In February 2018, PepsiCo went back to using aspartame in Diet Pepsi because of an 8% drop in sales for the previous year.[29][30]
Sucralose is adisaccharide composed of1,6-dichloro-1,6-dideoxyfructose and4-chloro-4-deoxygalactose. It issynthesized by the selective chlorination of sucrose in a multistep route that substitutes three specific hydroxyl groups withchlorine atoms. This chlorination is achieved by selectiveprotection of one of theprimary alcohols as anester (acetate orbenzoate), followed by chlorination with an excess of any of several chlorinating agent to replace the two remaining primary alcohols and one of the secondary alcohols, and then byhydrolysis of the ester.[31][32]
Sucralose is stable when stored under normal conditions of temperature, pressure and humidity.[33] Upon prolonged heating during storage at elevated temperatures (38 °C, 100 °F), sucralose may break down, releasingcarbon dioxide,carbon monoxide and minor amounts ofhydrogen chloride.[33]
No evidence of an effect of sucralose on long-termweight loss orbody mass index has been found, withcohort studies showing a minor effect on weight gain andheart disease risks.[34]
The majority of ingested sucralose is not metabolized by the human body, but is instead excreted unchanged. It is an emerging environmental contaminant that can not be removed in conventional waste water treatment process.[35][36]
According to one study, sucralose is digestible by a number of microorganisms and is broken down once released into the environment.[37] However, measurements by the Swedish Environmental Research Institute have shown thatsewage treatment has little effect on sucralose, which is present in wastewater effluents at levels of several μg/L (ppb).[38] No ecotoxicological effects are known at such levels, but theSwedish Environmental Protection Agency warns that a continuous increase in levels may occur if the compound is only slowly degraded in nature. When heated to very high temperatures (over 350 °C or 662 °F) in metal containers, sucralose can producepolychlorinated dibenzo-p-dioxins and otherpersistent organic pollutants in the resulting smoke.[39]
Sucralose has been detected in natural waters, but research indicates that the levels found in the environment are far below those required to cause adverse effects to certain kinds of aquatic life.[40]
Lead Deputy Commissioner for the FDA
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