Galactitol

Last updated
Galactitol
Dulcitol.svg
D-Galactitol.png
Names
IUPAC name
D-Galactitol
Systematic IUPAC name
(2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol
Other names
Dulcitol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.009.242 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6- Yes check.svgY
    Key: FBPFZTCFMRRESA-GUCUJZIJSA-N Yes check.svgY
  • InChI=1/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-
    Key: FBPFZTCFMRRESA-GUCUJZIJBM
  • O[C@H]([C@@H](O)CO)[C@@H](O)[C@H](O)CO
Properties
C6H14O6
Molar mass 182.172 g/mol
−112.40·10−6 cm3/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Galactitol (dulcitol) is a sugar alcohol, the reduction product of galactose. [1] It has a slightly sweet taste. [1] In people with galactokinase deficiency, a form of galactosemia, excess dulcitol forms in the lens of the eye leading to cataracts. [2]

Galactitol is produced from galactose in a reaction catalyzed by aldose reductase. [3]

The other common galactose metabolism defect is a defect in galactose-1-phosphate uridylyltransferase, an autosomal recessive disorder, which also causes a buildup of galactitol as a result of increased concentrations of galactose-1-phosphate and galactose. This disorder leads to cataracts caused by galactitol buildup. [4]

References

  1. 1 2 "Galactitol - Compound Summary". National Center for Biotechnology Information . Retrieved 2008-08-06.
  2. ↑ Roth, KS (September 10, 2007). "Galactokinase Deficiency". eMedicine . WebMD . Retrieved 2008-08-08.
  3. ↑ Narayanan, S. (1993-03-01). "Aldose reductase and its inhibition in the control of diabetic complications". Annals of Clinical & Laboratory Science. 23 (2): 148–158. ISSN   0091-7370. PMID   8457142.
  4. ↑ Palmieri, Michael; Mazur, Alice; Berry, Gerard T.; Ning, Cong; Wehrli, Suzanne; Yager, Claire; Reynolds, Robert; Singh, Rani; Muralidharan, Kasinathan; Langley, Sharon; Elsas, Louis; Segal, Stanton (1999-10-01). "Urine and plasma galactitol in patients with galactose-1-phosphate uridyltransferase deficiency galactosemia". Metabolism. 48 (10): 1294–1302. doi:10.1016/S0026-0495(99)90271-8. ISSN   0026-0495.
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