Showing Compound Galactitol (FDB006453)

Record Information

Version

1.0

Creation date

2010-04-08 22:07:09 UTC

Update date

2020-09-17 15:42:24 UTC

Primary ID

FDB006453

Secondary Accession Numbers

FDB030767

Chemical Information

FooDB Name

Galactitol

Description

Galactitol 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 Number

608-66-2

Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym	Source
(2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexol	ChEBI
Ambap5938	HMDB
D-Dulcitol	ChEBI
D-Galactitol	ChEBI
Dulcite	db_source
Dulcitol	db_source
Dulcose	db_source
Euonymit	db_source
galacto-Hexitol	db_source
Hexitol	HMDB
L-Galactitol	ChEBI
Melampyrin	db_source
Melampyrit	ChEBI
Melampyrite	HMDB
Melampyrum	db_source
Meso-galactitol	HMDB

Predicted Properties

Not Available

Chemical Formula

C6H14O6

IUPAC name

InChI Identifier

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

InChI Key

FBPFZTCFMRRESA-GUCUJZIJSA-N

Isomeric SMILES

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

Average Molecular Weight

182.1718

Monoisotopic Molecular Weight

182.07903818

Classification

Not classified

Ontology

Physiological effect

Health effect:

Health condition:

Galactosemia type 1

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Organ and components:

Brain

Biofluid and excreta:

Cell and elements:

Extracellular

Subcellular:

Process

Naturally occurring process:

Biological process:

Cellular process:

Cell signaling

Role

Indirect biological role:

Biological role:

Industrial application:

Physico-Chemical Properties - Experimental

Property	Value	Reference
Physical state	Solid
Physical Description	Not Available
Mass Composition	Not Available
Melting Point	189.5 oC
Boiling Point	Not Available
Experimental Water Solubility	31 mg/mL at 15 oC	YALKOWSKY,SH & DANNENFELSER,RM (1992)
Experimental logP	-3.10	HANSCH,C ET AL. (1995)
Experimental pKa	Not Available
Isoelectric point	Not Available
Charge	Not Available
Optical Rotation	Not Available
Spectroscopic UV Data	Not Available
Density	Not Available
Refractive Index	Not Available