Wikipedia

1,6-Dichloro-1,6-dideoxyfructose

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.

1,6-Dichloro-1,6-dideoxyfructose
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).

Metabolism edit

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 edit

  1. ^ Hough, L. (1993), Khan, Riaz (ed.), "High-intensity, low-calorie sweeteners", 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, retrieved 2022-11-24
  2. ^ PubChem. "1,6-Dichloro-1,6-dideoxyfructose". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-11-24.
  3. ^ "1,6-dichloro-1,6-dideoxyfructose | C6H10Cl2O4 | ChemSpider". www.chemspider.com. Retrieved 2022-11-24.
  4. ^ Labare, M. P.; Alexander, M. (1994-10-01). "Microbial cometabolism of sucralose, a chlorinated disaccharide, in environmental samples". Applied Microbiology and Biotechnology. 42 (1): 173–178. doi:10.1007/BF00170242. ISSN 1432-0614. PMID 7765816. S2CID 20916443.
  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. PMC 1138541. PMID 2719664.
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