Sucralosa

Sucralose

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Sucralose
Sucralose[1]

Identifiers CAS number PubChem ChemSpider UNII EC number SMILES InChI InChI key Properties Molecular formula Molar mass Melting point Boiling point Solubility in water C H Cl O
12 19 3 8

56038-13-2 71485 64561
[3] [4]  

[2]

 

96K6UQ3ZD4 259-952-2
[6]

[5]

 

397.64 g/mol 125 °C, 398 K, 257 °F 669 °C, 942 K, 1236 °F 283 g/L (20 °C) (what is this?)   (verify) [7]

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox references

Sucralose is a zero-calorie artificial sweetener. In the European Union, it is also known under the E number (additive code) E955. Sucralose is approximately 600 times as sweet as sucrose (table sugar),[8] twice as sweet as saccharin, and3.3 times as sweet as aspartame. It is stable under heat and over a broad range of pH conditions. Therefore, it can be used in baking or in products that require a longer shelf life. The commercial success of sucralose-based products stems from its favorable comparison to other low-calorie sweeteners in terms of taste, stability, and safety.[9]

Sucralose Sucralose is typically added to foodsin very small quantities. Sucralose products manufactured in the US for domestic consumption are commonly formulated by the addition of "bulking" ingredients such as glucose (dextrose) and maltodextrin to give a degree of sweetness per unit volume comparable to sucrose, and to give some products an appearance similar to granular sugar. Some examples of these sweeteners are Splenda, SucraPlus,Candys, Cukren, and Nevella.

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History
Sucralose was discovered in 1989 by scientists from Tate & Lyle, working with researchers Leslie Hough and Shashikant Phadnis at Queen Elizabeth College (now part of King's College London).[10] While researching ways to use sucrose as a chemical intermediate in non-traditional areas, Phadnis was told to test a chlorinated sugar compound. Phadnis thoughtthat Hough asked him to taste it, so he did.[10] He found the compound to be exceptionally sweet. 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.[11] In2006 the FDA amended the regulations for foods to include sucralose as a non-nutritive sweetener in food.[12] In May 2008, Fusion Nutraceuticals launched a generic product to the market, using Tate & Lyle patents.

Production

Comparison of the chemical structures of sucrose (top) and sucralose (bottom). Tate & Lyle manufactures sucralose at a plant in Jurong, Singapore.[13] Formerly,production was completed at a plant in McIntosh, Alabama. 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 oneof 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.[14]

Synthesis
Synthesis of sucralose from sucrose requires chlorination at 4-, 1'- and 6'-positions of sucrose. Two primary hydroxyl groups (1' and 6') and one secondary hydroxyl group (4-) need to bereplaced with chlorine while the third primary hydroxyl group (6-) is unaffected. Therefore, one route to synthesize sucralose is to first protect the 6-hydroxyl group via esterification to generate sucrose-6-ester, convert the partly protected sucrose to sucralose-6-ester by selective chlorination under certain conditions, with optional esterification of all the hydroxyl groups for the purpose of...