U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C6H14O6
Molecular Weight 182.1718
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALACTITOL

SMILES

OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO

InChI

InChIKey=FBPFZTCFMRRESA-GUCUJZIJSA-N
InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-

HIDE SMILES / InChI

Molecular Formula C6H14O6
Molecular Weight 182.1718
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including https://www.aao.org/bcscsnippetdetail.aspx?id=256624ba-52bc-4dd2-9d10-b97d5002d83d | http://www.mayomedicallaboratories.com/test-catalog/Clinical+and+Interpretive/62440 | https://www.google.ch/patents/US4797388 | https://www.ncbi.nlm.nih.gov/pubmed/22710095

Galactitol (dulcitol) is a sugar alcohol, the reduction product of galactose. Galactitol is known to be the major toxic metabolites of galactose. Deficiency of any one of three possible enzymes involved in the metabolism of galactose: galactokinase, transferase or epimerase results in galactosemia. Any single deficient enzyme can result in cataract through the accumulation of galactitol in the lens. Accumulation of galactose and galactitol within the lens cells leads to an increase in intracellular osmotic pressure and an influx of fluid in the lens. Kinoshita was the first to demonstrate the hyperosmotic effects of intracellular sorbitol or galactitol accumulation and to postulate that the resulting cellular swelling can lead to increased membrane permeability and a series of complex biochemical changes associated with sugar cataract formation. The excretion of abnormal quantities of galactitol in the urine of galactosemia patients is characteristic of this disorder. A patent claims galactitol as carrier for the therapeutic agent since galactitol enhances the chemical and physical stability of the drug and allows faster reconstitution of the formulation in water than mannitol.

CNS Activity

Curator's Comment: Galactitol accumulaes in the brain of patients with galactosemia

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Synthesis, characterization, and biological activity of oxovanadium(IV) complexes with polyalcohols.
2006-05-01
D-Galactose induces cellulase gene expression in Hypocrea jecorina at low growth rates.
2006-05
Estradiol attenuates mitochondrial depolarization in polyol-stressed lens epithelial cells.
2006-04-04
[A difficult and complicated case study: neonatal intrahepatic cholestasis caused by citrin deficiency].
2006-04
Urinary galactitol and galactonate quantified by isotope-dilution gas chromatography-mass spectrometry.
2006-04
Stereoselective synthesis of alpha-C-Substituted 1,4-dideoxy-1,4-imino-D-galactitols. Toward original UDP-Galf mimics via cross-metathesis.
2006-03-30
Simultaneous measurement of urinary polyols using gas chromatography/mass spectrometry.
2006-02-02
8-hydroxy-2-desoxyguanosine serum concentrations as a marker of DNA damage in patients with classical galactosaemia.
2006-02
Crystal structures and spectroscopic characterization of galactitol complexes of trivalent lanthanide and divalent alkaline earth chlorides.
2006-01-16
Proton MR spectroscopy and imaging of a galactosemic patient before and after dietary treatment.
2006-01
[Study on the chemical constituents of Buddleja purdomii].
2005-11
Suckling rat brain regional distribution of acetylcholinesterase activity in galactosaemia in vitro.
2005-09
An updated review of the long-term neurological effects of galactosemia.
2005-09
Characterization of two major groups of diarrheagenic Escherichia coli O26 strains which are globally spread in human patients and domestic animals of different species.
2005-08-15
[Characterization and identification of Ralstonia solanacearum by ion-exchange chromatography].
2005-07
Desulfurococcus fermentans sp. nov., a novel hyperthermophilic archaeon from a Kamchatka hot spring, and emended description of the genus Desulfurococcus.
2005-05
A comprehensive update of the sequence and structure classification of kinases.
2005-03-16
The protective effect of L-cysteine and glutathione on the adult and aged rat brain (Na+,K+)-ATPase and Mg2+-ATPase activities in galactosemia in vitro.
2005-03
Suckling rat brain regional distribution of Na+,K+-atpase activity in the in vitro galactosaemia: the effect of L-cysteine and glutathione.
2005-03
Mg2+-ATPase activity in suckling rat brain regions in galactosaemia in vitro. L-Cysteine and glutathione effects.
2005-03
The effect of diet on total antioxidant status, erythrocyte membrane Na+,K+-ATPase and Mg2+-ATPase activities in patients with classical galactosaemia.
2005-02
Galactitol and galactonate in red blood cells of children with the Duarte/galactosemia genotype.
2005-02
Four new prenylated isoflavonoids in Tadehagi triquetrum.
2005-01-26
Analysis of polyols in urine by liquid chromatography-tandem mass spectrometry: a useful tool for recognition of inborn errors affecting polyol metabolism.
2005
Quantitative determination of endogenous sorbitol and fructose in human nerve tissues by atmospheric-pressure chemical ionization liquid chromatography/tandem mass spectrometry.
2005
Galactosaemia: early treatment with an elemental formula.
2005
Genetic diversity among Pasteurella multocida strains of avian, bovine, ovine and porcine origin from England and Wales by comparative sequence analysis of the 16S rRNA gene.
2004-12
Trichosporon mycotoxinivorans sp. nov., a new yeast species useful in biological detoxification of various mycotoxins.
2004-11
High tolerance for oral galactose in classical galactosaemia: dietary implications.
2004-11
Cognitive strengths and weaknesses in children and adolescents homozygous for the galactosemia Q188R mutation: a descriptive study.
2004-10
Anaphylaxis to excipient mannitol: evidence for an immunoglobulin E-mediated mechanism.
2004-10
Aeromonas spp. and infectious diarrhea, Hong Kong.
2004-08
Identification of sorbitol transporters expressed in the phloem of apple source leaves.
2004-08
The genes and enzymes for the catabolism of galactitol, D-tagatose, and related carbohydrates in Klebsiella oxytoca M5a1 and other enteric bacteria display convergent evolution.
2004-07
Characterization of Neisseria meningitidis isolates collected from 1974 to 2003 in Japan by multilocus sequence typing.
2004-07
The metabolic role and evolution of L-arabinitol 4-dehydrogenase of Hypocrea jecorina.
2004-05
Ophthalmoscopic and morphogenetic changes in rat lens induced by galactose: attenuation by pyruvate.
2004-05
Protective effect of L-cysteine and glutathione on the modulated suckling rat brain Na+, K+, -ATPase and Mg2+ -ATPase activities induced by the in vitro galactosaemia.
2004-05
Autodisplay of active sorbitol dehydrogenase (SDH) yields a whole cell biocatalyst for the synthesis of rare sugars.
2004-04-02
tRNA-intergenic spacer PCR for the identification of Pasteurella and Mannheimia spp.
2004-03-05
Galactonate determination in urine by stable isotope dilution gas chromatography-mass spectrometry.
2004-03-05
The galactokinase of Hypocrea jecorina is essential for cellulase induction by lactose but dispensable for growth on d-galactose.
2004-02
Galactitol and galactonate accumulation in heart and skeletal muscle of mice with deficiency of galactose-1-phosphate uridyltransferase.
2004-02
Age dependence of endogenous galactose formation in Q188R homozygous galactosemic patients.
2004-01
Galactitol and galactonate in red blood cells of galactosemic patients.
2003-11
Stereoselective oxidation of aliphatic diols and reduction of hydroxy-ketones with galactitol dehydrogenase from Rhodobacter sphaeroides D.
2003
Bioinformatic analyses of the bacterial L-ascorbate phosphotransferase system permease family.
2003
Mutations in galactose-1-phosphate uridyltransferase gene in patients with idiopathic presenile cataract.
2003
Stable-isotope dilution analysis of galactose metabolites in human erythrocytes.
2003
Galactitol is not a cause of senile cataract.
1992
Patents

Sample Use Guides

Adult male rats were fed the basal diet or the same diet to which had been added either galactitol, mannitol or xylitol for 8 wk (final polyol level 200 g/kg diet).
Route of Administration: Oral
Metaphase II mouse oocytes with and without cumulus cells (CCs), were exposed for 4 hours to D-galactose (2 μM), galactitol (11 μM) and galactose 1-phosphate (0.1 mM), (corresponding to plasma concentrations in patients on galactose-restricted diet) and compared to controls. The treated oocytes showed decreased quality as a function of significant enhancement in production of reactive oxygen species (ROS) when compared to controls.
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:00:08 GMT 2025
Edited
by admin
on Mon Mar 31 20:00:08 GMT 2025
Record UNII
113ZQ1Y7DD
Record Status Validated (UNII)
Record Version
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Name Type Language
NSC-1944
Preferred Name English
GALACTITOL
MI   USP-RS  
Common Name English
DULCITOL
Common Name English
MELAMPYRITE
Common Name English
DULCOSE
Common Name English
MELAMPYRIN
Common Name English
GALACTITOL [USP-RS]
Common Name English
DULCITE
Common Name English
LACTITOL MONOHYDRATE IMPURITY D [EP IMPURITY]
Common Name English
MELAMPYRIT
Common Name English
EUONYMIT
Common Name English
GALACTITOL [MI]
Common Name English
Classification Tree Code System Code
LOINC 49333-8
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
LOINC 57967-2
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
LOINC 47857-8
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
LOINC 49773-5
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
Code System Code Type Description
CAS
608-66-2
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY
FDA UNII
113ZQ1Y7DD
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY
RS_ITEM_NUM
1287711
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY
PUBCHEM
11850
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY
EPA CompTox
DTXSID1046051
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY
NSC
1944
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY
CHEBI
16813
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY
ECHA (EC/EINECS)
210-165-2
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PRIMARY
CHEBI
16899
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY
MESH
D004376
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY
MERCK INDEX
m5632
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY Merck Index
WIKIPEDIA
GALACTITOL
Created by admin on Mon Mar 31 20:00:08 GMT 2025 , Edited by admin on Mon Mar 31 20:00:08 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> METABOLITE
In people with galactokinase deficiency, a form of galactosemia, excess dulcitol forms in the lens of the eye leading to cataracts.
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP