Chemistry:1,6-Dichloro-1,6-dideoxyfructose

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1,6-Dichloro-1,6-dideoxyfructose
1,6-Dichlorfructose.svg
Haworth projection of 1,6-Dichloro-1,6-dideoxyfructose.svg
Names
IUPAC name
(3S,4S,5S)-1,6-dichloro-3,4,5-trihydroxyhexan-2-one
Identifiers
3D model (JSmol)
ChemSpider
UNII
Properties
C6H10Cl2O4
Molar mass 217.04 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

1,6-Dichloro-1,6-dideoxyfructose (dichlorodideoxyfructose)[1][2][3] is chlorinated derivative of the sugar fructose. It is one of the two components believed to comprise the disaccharide sucralose,[4] a commercial sugar substitute.

Metabolism

In mammals, 1,6-dichloro-1,6-dideoxyfructose is metabolized in the liver and erythrocytes by a reaction with glutathione that replaces one of the chlorine atoms, forming 6-chlorofructos-1-yl glutathione (or chlorofructosyl glutathione).[5]

References

  1. Hough, L. (1993), Khan, Riaz, ed., "High-intensity, low-calorie sweeteners" (in en), Low-Calorie Foods and Food Ingredients (Boston, MA: Springer US): pp. 138–164, doi:10.1007/978-1-4615-3114-2_7, ISBN 978-1-4615-3114-2, https://doi.org/10.1007/978-1-4615-3114-2_7, retrieved 2022-11-24 
  2. PubChem. "1,6-Dichloro-1,6-dideoxyfructose" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/3081555. 
  3. "1,6-dichloro-1,6-dideoxyfructose | C6H10Cl2O4 | ChemSpider". http://www.chemspider.com/Chemical-Structure.2339136.html. 
  4. Labare, M. P.; Alexander, M. (1994-10-01). "Microbial cometabolism of sucralose, a chlorinated disaccharide, in environmental samples" (in en). Applied Microbiology and Biotechnology 42 (1): 173–178. doi:10.1007/BF00170242. ISSN 1432-0614. PMID 7765816. https://doi.org/10.1007/BF00170242. 
  5. Hughes, H M; Powell, G M; Snodin, D J; Daniel, J W; Crawford, A; Sanders, J K; Curtis, C G (15 April 1989). "Glutathione-dependent dechlorination of 1,6-dichloro-1,6-dideoxyfructose". Biochemical Journal 259 (2): 537–543. doi:10.1042/bj2590537. PMID 2719664.