Sucralose

from Wikipedia, the free encyclopedia
Structural formula
Structure of sucralose
General
Surname Sucralose
other names
  • 1,6-dichloro-1,6-dideoxy-β- D -fructofuranosyl-4-chloro-4-deoxy-α- D -galactopyranoside
  • Trichlor galacto sucrose
  • E  955
  • TGS
  • Chlorosucrose
Molecular formula C 12 H 19 Cl 3 O 8
Brief description

colorless crystals

External identifiers / databases
CAS number 56038-13-2
EC number 259-952-2
ECHA InfoCard 100.054.484
PubChem 71485
Wikidata Q410209
properties
Molar mass 397.63 g mol −1
Physical state

firmly

solubility
  • easily soluble in water (283 g l −1 at 20 ° C) and ethanol (90 g l −1 )
  • slightly soluble in ethyl acetate
safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Sucralose ( E 955 ) is a sweetener that tastes around 600 times sweeter than granulated sugar . The substance itself and its aqueous solution sold as liquid sweetener are "calorie-free". Sweeteners that are additionally diluted with substances such as maltodextrin are relevant for carbohydrate digestion.

history

Sucralose was discovered and developed by Tate & Lyle and Queen Elizabeth College , University of London, in a targeted search for a sweetener to be made from sugar. In 1976, tetrachlorogalactosucrose was the first compound to be synthesized and its sweet taste was demonstrated. The various OH groups were then systematically substituted by chlorine and in the first patent from 1976 nine chlorine-containing derivatives were shown, of which trichlorogalactosucrose had the greatest sweetness. This compound was first approved under the name sucralose in Canada in 1991, in the USA in 1999 and in the EU in 2004.

Sucralose is mainly made in the USA . Since 1998 it has been approved in more than 60 countries. Since April 2004 sucralose has also been approved as a food additive in the European Union . In Germany, sucralose was approved on January 26, 2005 in accordance with the additive approval regulation.

Manufacturing

The preparation of sucralose trichlorosucrose is performed by chlorination of sucrose . Three hydroxyl groups are exchanged for chlorine atoms.

properties

Sucralose doesn't have a bitter aftertaste. The taste perception of the sweetness sets in late, after swallowing a persistent sweet aftertaste can be determined. Sucralose has no significant physiological calorific value , as it can only slightly break down the enzymes involved in carbohydrate digestion , does not cause tooth decay , has high heat stability and very good solubility and miscibility with other food components. With the slight breakdown, up to 15% of sucralose is metabolized to 1,6-dichlorofructose , which varies from individual to individual, and this can lead to significantly more severe side effects (flatulence, diarrhea, vomiting, circulatory collapse) in people with fructose intolerance than with fructose . Sucralose in aqueous solution is reactive over a long period of time at very high degrees of acidity and temperatures.

The permitted daily dose is 15 mg per kg of body weight.

use

Sucralose is sold under the trade name Splenda by Heartland Food Products Group . In addition to sucralose, table sweetener in powder or tablet form also contains dextrose , maltodextrin or lactose , leucine and carboxymethyl cellulose . Sucralose in liquid form was marketed under the trade name Candys in 2007. This sterile drip solution contains only water and sucralose.

safety instructions

Like many other organochlorine compounds , sucralose is slow to break down in the environment or in sewage treatment plants. As a result, it accumulates in the environment and is detectable in rivers. While there is evidence that sucralose causes side effects, no scientific evidence has been provided to date. In some animal experiments there were some indications of possible complications that could be caused by sucralose, for example a negative influence on the intestinal flora . However, since a harmful effect could not be scientifically confirmed at first, the European Union decided on September 7, 2000 to assign sucralose to the safe products and to release them for consumption.

The Swedish environmental authority Naturvårdsverket also put sucralose on the list of harmless substances in 2005. A review article mentions that when exposed to thermal stress - for example from cooking or baking - sucralose dioxins can form. Since when sucralose or foods with sucralose are heated above 120 ° C, chlorinated organic compounds with potential health hazards can be formed, such as polychlorinated dibenzo-p-dioxins (PCDD) or dibenzofurans (PCDF) or chloropropanols, the Federal Institute for Risk Assessment recommends a preliminary assessment of a corresponding heating.

Web links

Commons : Sucralose  - collection of images, videos and audio files

Individual evidence

  1. ↑ Entry on E 955: Sucralose in the European database on food additives, accessed on June 27, 2020.
  2. ↑ a b c A. Täufel, W. Ternes, L. Tunger, M. Zobel (Eds.): Food lexicon . Behr, 4th edition 2005; ISBN 3-89947-165-2 ; P. 1810.
  3. ↑ a b c Entry on sucralose. In: Römpp Online . Georg Thieme Verlag, accessed on July 17, 2014.
  4. ↑ Sucralose data sheet from Sigma-Aldrich , accessed on June 15, 2011 ( PDF ).Template: Sigma-Aldrich / name not given
  5. ^ Tate & Lyle Company History
  6. ↑ Zuckerinfo.de ( Memento from May 12, 2014 in the Internet Archive )
  7. ^ Burkhard Bilger: The Search for Sweet . In: The New Yorker , May 22, 2006.
  8. ↑ Klaus Roth , Erich Lück: Calorie-free sweetness from the laboratory and nature . In: Chemistry in Our Time . tape 46 , no. 3 , 2012, p. 168–192, here p. 182 , doi : 10.1002 / ciuz.201200587 .
  9. ^ Everything You Need to Know About Sucralose: Educational Booklets & Brochures. ( April 18, 2009 memento on the Internet Archive ) American Academy Of Family Physicians, 2004.
  10. ↑ Mikael Krogerus: Bitter fight for sweet margins . In: NZZ Folio . Born in 2006, No. 3.
  11. ↑ Daniela Fischer: Sucralose - a new sweetener. Chemistry in Everyday Life, 2006, accessed July 2, 2014 .
  12. ↑ Amendment to Directive 94/35 on sweeteners: scope of the authorization of sucralose (PDF; 22 kB). Statement by the BgVV, Federal Institute for Risk Assessment , February 9, 2001.
  13. ↑ Stiftung Warentest: Sweeteners: Much synthetic for those with a sweet tooth in: test 10/2006 (accessed online on February 4, 2013).
  14. Jump up ↑ No Calorie Sweetener & Sugar Substitute. In: splenda.com. Retrieved June 14, 2018 .
  15. ↑ Naomi Lubick: Artificial sweetener persists in the environment (PDF; 336 kB) . ES&T Science News, March 12, 2008, doi: 10.1021 / es087043g .
  16. ↑ Deutschlandfunk , Forschung aktuell, broadcast on September 22, 2011 Acesulfam: Unmolested by the toilet, sewer and sewage treatment plant
  17. ^ MR Weihrauch, V. Diehl (2004): Artificial sweeteners - do they bear a carcinogenic risk? . In: Annals of Oncology . Vol. 15, (10), pp. 1460-1465, PMID 15367404 .
  18. ↑ Abou-Donia MB et al. (2008): Splenda alters gut microflora and increases intestinal p-glycoprotein and cytochrome p-450 in male rats . In: Journal of Toxicology and Environmental Health . 71 (21): pp. 1415-1429, PMID 18800291 .
  19. ↑ Scientific Committee on Food of the European Commission (2000): SCF / CS / ADDS / EDUL / 190 Opinion of the Scientific Committee on Food on sucralose (PDF; 132 kB).
  20. ↑ Nils-Gunnar Ilbäck, Kettil Svensson (2005): Sukralos har utvärderats av och EU WHO. In: Nyhetslista . Swedish Environment Agency Naturvårdsverket .
  21. ↑ Susan S. Schiffman & Kristina I. Rother: Sucralose, A Synthetic Organochlorine Sweetener: Overview Of Biological Issues. ; Journal of Toxicology and Environmental Health , 16 (2013), pp. 399-451, doi: 10.1080 / 10937404.2013.842523 .
  22. ↑ BfR Opinion No. 012/2019 of the BfR of April 9, 2019. Federal Institute for Risk Assessment, April 9, 2019, accessed on April 10, 2019 .