Record Information
Version1.0
Creation date2010-04-08 22:07:09 UTC
Update date2020-09-17 15:42:24 UTC
Primary IDFDB006453
Secondary Accession Numbers
  • FDB030767
Chemical Information
FooDB NameGalactitol
DescriptionGalactitol or dulcitol is a sugar alcohol that is a metabolic breakdown product of galactose. Galactitol is an extremely weak basic (essentially neutral) compound (based on its pKa). Galactose is derived from lactose in food (such as dairy products). When lactose is broken down by the enzyme lactase it produces glucose and galactose. It is this galactose that is broken down to galactitol via a reaction catalyzed by aldose reductase. Galactitol has a slightly sweet taste. When present in sufficiently high levels, galactitol can act as a metabotoxin, a neurotoxin, and a hepatotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A hepatotoxin as a compound that disrupts or attacks liver tissue or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of galactitol are associated with at least two inborn errors of metabolism, including galactosemia and galactosemia type II. Galactosemia is a rare genetic metabolic disorder that affects an individual's ability to metabolize the sugar galactose properly. Excess lactose consumption in individuals with galactose intolerance or galactosemia activates aldose reductase to produce galactitol, thus depleting NADPH and leading to lowered glutathione reductase activity. As a result, hydrogen peroxide or other free radicals accumulate causing serious oxidative damage to various cells and tissues. In individuals with galactosemia, the enzymes needed for the further metabolism of galactose (galactose-1-phosphate uridyltransferase) are severely diminished or missing entirely, leading to toxic levels of galactose 1-phosphate, galactitol, and galactonate. High levels of galactitol in infants are specifically associated with hepatomegaly (an enlarged liver), cirrhosis, renal failure, cataracts, vomiting, seizure, hypoglycemia, lethargy, brain damage, and ovarian failure. Outside of the human body, Galactitol has been detected, but not quantified in, several different foods, such as common buckwheats, winter squash, calabash, black walnuts, and peanuts. This could make galactitol a potential biomarker for the consumption of these foods.
CAS Number608-66-2
Structure
Thumb
Synonyms
SynonymSource
(2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexolChEBI
Ambap5938HMDB
D-DulcitolChEBI
D-GalactitolChEBI
Dulcitedb_source
Dulcitoldb_source
Dulcosedb_source
Euonymitdb_source
galacto-Hexitoldb_source
HexitolHMDB
L-GalactitolChEBI
Melampyrindb_source
MelampyritChEBI
MelampyriteHMDB
Melampyrumdb_source
Meso-galactitolHMDB
Predicted PropertiesNot Available
Chemical FormulaC6H14O6
IUPAC name
InChI IdentifierInChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-
InChI KeyFBPFZTCFMRRESA-GUCUJZIJSA-N
Isomeric SMILESOC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO
Average Molecular Weight182.1718
Monoisotopic Molecular Weight182.07903818
Classification
ClassificationNot classified
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting Point189.5 oC
Boiling PointNot Available
Experimental Water Solubility31 mg/mL at 15 oCYALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP-3.10HANSCH,C ET AL. (1995)
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MSNot Available
NMRNot Available
ChemSpider ID11357
ChEMBL IDCHEMBL1773904
KEGG Compound IDC01697
Pubchem Compound ID11850
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00107
CRC / DFC (Dictionary of Food Compounds) IDBVW44-V:BVW44-V
EAFUS IDNot Available
Dr. Duke IDGALACTITOL
BIGG ID38183
KNApSAcK IDC00001160
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDGalactitol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043 map00052
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).