Sucralose, structure

Substituent effect, additivity of, 570 electrophilic aromatic substitution and, 560-563 summary of. 569 Substitution reaction, 138 Substrate (enzyme), 1041 Succinic acid, structure of, 753 Sucralose, structure of. 1006 sweetness of, 1005 Sucrose, molecular model of. 999 specific rotation of, 296 structure of, 999 sweetness of, 1005 Sugar, complex, 974 d, 980 L, 980... 

Sucralose has the structure most similar to su crose Galactose replaces the glucose unit of sucrose and chlorines replace three of the hydroxyl groups Sucralose is the newest artificial sweetener having been approved by the U S Food and Drug Adminis tration in 1998 The three chlorine substituents do not dimmish sweetness but do interfere with the ability of the body to metabolize sucralose It there fore has no food value and IS noncaloric... 

Saccharin sucralose and aspartame illustrate the diversity of structural types that taste sweet and the vitality and continuing development of the in dustry of which they are a part ... 

Did you know the average American consumes the equivalent of 20 teaspoons of sugar each day The non-nutritive sweetener industry is described as a billion-dollar industry with projections of even more rapid expansion in the next few years. What do chemists look for in their search for an ideal sweetener Consumers seek good-tasting, nontoxic, low-caloric sweeteners. Chemists in the sweetener industry add further demands an inexpensive, easy-to-synthesize product that is readily soluble in water and resists degradation by heat and light is of prime importance. The chemical structure of sucralose keeps the sweetener intact as it passes through the acidic environment of the stomach. Thus, sucralose is not... 

Sweet Taste. The mechanism of sweetness perception has been extensively studied because of its commercial importance. Many substances that vary in chemical structure have been discovered which are similar to the taste of sucrose. Commercial sweeteners include sucralose, acesulfame-K, saccharin, aspartame, cyclamate (Canada) and the protein thaumatin 4), Each sweetener is unique in its perceived sensation because of the time to the onset of sweetness and to maximum sweetness, ability to mask other sensations, persistence, aftertaste and intensity relative to sucrose [TABLE IT. For example, the saccharides, sorbitol and... 

The disaccharide structure of (12) (trade name SPLENDA) is emphasized by the manufacturer as responsible for a taste quality and time—intensity profile closer to that of sucrose than any other high potency sweetener. The sweetness potency at the 10% sucrose solution sweetness equivalence is between 450 and 500X, or about two and one-half times that of aspartame. When compared to a 2% sugar solution, the potency of sucralose can be as high as 750X. A moderate degree of synergy between sucralose and other nonnutritive (91) or nutritive (92) sweeteners has been reported. 

Sucralose, Developed in England during the mid-1980s, testing and evaluation commenced in 1988. The structural formula of the compound (a chlorinated disaccharide derived from sucrose) is shown below. 

Fig-1 Chemical structures of the intense sweeteners saccharin, sodium cyclamate, acesulfame-K, aspartame, alitame, dulcin, sucralose, and neohesperidin dihydrochalcone. 

Another widely used artificial sweetener is sucralose which is made by modifying sucrose (compare the structure of sucralose to sucrose shown above). Look at the groups with blue circles in each structure. Sucralose is 600 times as sweet as sucrose and is used to sweeten beverages, baked goods, yogurt, and desserts. 

FIGURE 5.27 Structures of sucralose and related carbohydrate compounds (a) and (b). (Copyright 2000 from CEC analysis of sucralose and related carbohydrate compounds by Zhao, R.R. and Johnson, B.P. Reproduced by permission of Taylor Francis Group, LLC., http //www.taylorandfrancis.com)... 

Sucralose (Splenda) is a relatively new artificial sweetener that was approved for use in the United States in 1998 after several years of use in other countries. It is purported to be as much as 600 times sweeter than sucrose. A comparison of its structure to that of sucrose reveals that sucralose is prepared by the replacement of three OH groups in sucrose by three Cl atoms. Like that of other artificial sweeteners, the safety of sucralose has been publicly questioned by some consumer advocate groups. 

Following is the structure of the artificial sweetener sucralose. Indicate all the ways in which it differs from sucrose. 

D-Sucralose is a trichloro derivative of sucrose whose structure is shown on page 490. This disaccharide is 600 times sweeter than sucrose and is sold under the brand name of Splenda . For a nice review of the synthesis and properties of commercial, synthetic nonnutritive sweeteners, see Angew. Chem. Int. Ed. 1998, 37,... 

Sucralose is a chlorinated derivative of sucrose that is about 600 times sweeter than its parent. It is hydrolyzed only slowly at the mildly acidic pH of soft drinks. Draw the structure of the hydrolysis products. 

Some organohalides have even been used in the food industry. Consider, for example, the structure of sucralose, shown here. Sucralose contains three chlorine atoms, but it is known not to be toxic. It is several hundred times sweeter than sugar and is sold as an artificial, low-calorie sweetener under the trade name Splenda . 

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