Sucralose

Chemistry

Sucralose is a sucrose molecule in which three of the -OH groups have been replaced by chlorine atoms. In the course of the chlorination, the stereochemistry at position 4 of the glucose ring gets inverted, so it becomes a derivative of galacto-sucrose.

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Molecular formula: C12H19Cl3O8
Molecular weight: 397.64
Sucralose is relatively stable; at high temperature in aqueous solution it is hydrolyzed to a limited extent, producing 4-chloro-4-deoxy-galactose and 1,6-dichloro-1,6-dideoxy-fructose.

Biology

Sucralose has undergone extensive safety testing. It appears to be only partially absorbed, followed by excretion in the kidneys.

Discovery

Sucralose may have the strangest "accidental discovery" story of all the sweeteners. Tate & Lyle, a British sugar company, was looking for ways to use sucrose as a chemical intermediate. In collaboration with Prof. Leslie Hough's laboratory at King's College in London, halogenated sugars were being synthesized and tested. A foreign graduate student, Shashikant Phadnis, misunderstood a request for "testing" of a chlorinated sugar as a request for "tasting," leading to the discovery that many chlorinated sugars are sweet with potencies some hundreds or thousands of times as great as sucrose.
If you are interested in sweetener discovery stories, see The History of High Potency Sweeteners: Tales of Discovery.

Names

1,6-Dichloro-1,6-dideoxy-beta-D-fructofuranosyl-4-chloro-4-deoxy-alpha-D-galactopyranoside
4,1',6'-Trichloro-4,1',6'-trideoxy-galacto-sucrose
1',4,6'-Trichloro-galactosucrose
TGS
Splenda™
Sucralose

Taste

"At a sucrose equivalency of 8%, in a buffered system, sucralose was perceived as being primarily sweet with slight drying and sour characteristics as compared to sucrose. At a 12% sucrose equivalency, sucralose was again perceived to deliver some drying and sour attributes, with a very slight rubbery taste." [S.G. Wiet & G.A. Miller, Food Chem. 58:306-307 (1997)] The sweetness potency relative to sucrose is about 600, but depends upon the concentration of sucrose which is being matched. The concentration vs. response relationship in water (results in food systems will vary) is shown below. This graph is based on data from DuBois, Walters, Schiffman, Warwick, Booth, Pecore, Gibes, Carr & Brands in "Sweeteners: Discovery, Molecular Design, and Chemoreception," D.E. Walters et al., Eds., American Chemical Society, 1991. The equation allows you to calculate sweetness response (R) for any concentration (C). The units of R are percent sucrose equivalent; the units of C are parts per million (ppm).

Other links

• McNeil Specialty Products has a web site at www.splenda.com
• You currently get to the same web page using www.sucralose.com
• The American Dietetic Association has objective and well-documented information about sweeteners on its website.

© by D. Eric Walters

Molecular formula: C12H19Cl3O8
Molecular weight: 397.64
Sucralose is relatively stable; at high temperature in aqueous solution it is hydrolyzed to a limited extent, producing 4-chloro-4-deoxy-galactose and 1,6-dichloro-1,6-dideoxy-fructose.

Biology

Sucralose has undergone extensive safety testing. It appears to be only partially absorbed, followed by excretion in the kidneys.

Discovery

Sucralose may have the strangest "accidental discovery" story of all the sweeteners. Tate & Lyle, a British sugar company, was looking for ways to use sucrose as a chemical intermediate. In collaboration with Prof. Leslie Hough's laboratory at King's College in London, halogenated sugars were being synthesized and tested. A foreign graduate student, Shashikant Phadnis, misunderstood a request for "testing" of a chlorinated sugar as a request for "tasting," leading to the discovery that many chlorinated sugars are sweet with potencies some hundreds or thousands of times as great as sucrose.
If you are interested in sweetener discovery stories, see The History of High Potency Sweeteners: Tales of Discovery.

Names

1,6-Dichloro-1,6-dideoxy-beta-D-fructofuranosyl-4-chloro-4-deoxy-alpha-D-galactopyranoside
4,1',6'-Trichloro-4,1',6'-trideoxy-galacto-sucrose
1',4,6'-Trichloro-galactosucrose
TGS
Splenda™
Sucralose

Taste

"At a sucrose equivalency of 8%, in a buffered system, sucralose was perceived as being primarily sweet with slight drying and sour characteristics as compared to sucrose. At a 12% sucrose equivalency, sucralose was again perceived to deliver some drying and sour attributes, with a very slight rubbery taste." [S.G. Wiet & G.A. Miller, Food Chem. 58:306-307 (1997)] The sweetness potency relative to sucrose is about 600, but depends upon the concentration of sucrose which is being matched. The concentration vs. response relationship in water (results in food systems will vary) is shown below. This graph is based on data from DuBois, Walters, Schiffman, Warwick, Booth, Pecore, Gibes, Carr & Brands in "Sweeteners: Discovery, Molecular Design, and Chemoreception," D.E. Walters et al., Eds., American Chemical Society, 1991. The equation allows you to calculate sweetness response (R) for any concentration (C). The units of R are percent sucrose equivalent; the units of C are parts per million (ppm).

Other links

• McNeil Specialty Products has a web site at www.splenda.com
• You currently get to the same web page using www.sucralose.com
• The American Dietetic Association has objective and well-documented information about sweeteners on its website.

© by D. Eric Walters