FComEx: Galactitol (PC000060)

Record Information

Version

1.0

Creation date

2015-10-09 22:27:47 UTC

Update date

2017-01-19 02:36:11 UTC

FoodComEx ID

PC000060

FoodDB Record

FDB006453

Chemical Information

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

Chemical Formula

C6H14O6

IUPAC name

(2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol

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

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents