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
  • InChI=1S/C6H10Cl2O4/c7-1-3(9)5(11)6(12)4(10)2-8/h3,5-6,9,11-12H,1-2H2/t3-,5-,6-/m1/s1
    Key: MLQSSVPAOPJIFW-UYFOZJQFSA-N
  • C([C@H]([C@H]([C@@H](C(=O)CCl)O)O)O)Cl
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).

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

References

  1. ^ 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. PMC 1138541. PMID 2719664.