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
D-Dulcitol	ChEBI
D-Galactitol	ChEBI
Dulcitol	ChEBI
Dulcose	ChEBI
Euonymit	ChEBI
L-Galactitol	ChEBI
Melampyrin	ChEBI
Melampyrit	ChEBI
Ambap5938	HMDB
Dulcite	HMDB
Hexitol	HMDB
Melampyrite	HMDB
Melampyrum	HMDB
meso-Galactitol	HMDB
galacto-Hexitol	db_source
Meso-galactitol	HMDB

Predicted Properties

Property	Value	Source
Water Solubility	229 g/L	ALOGPS
logP	-2.7	ALOGPS
logP	-3.7	ChemAxon
logS	0.1	ALOGPS
pKa (Strongest Acidic)	12.59	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	121.38 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	38.4 m³·mol⁻¹	ChemAxon
Polarizability	17.25 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

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

Classification

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

Sugar alcohol
Monosaccharide
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hexitol (CHEBI:16813 )

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

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	Galactitol, non-derivatized, GC-MS Spectrum	splash10-014j-0941000000-61141f9f2ddc66e0b016	Spectrum
GC-MS	Galactitol, 6 TMS, GC-MS Spectrum	splash10-0gb9-1983000000-0a0dafcfea843fbb3c72	Spectrum
GC-MS	Galactitol, non-derivatized, GC-MS Spectrum	splash10-014j-0941000000-61141f9f2ddc66e0b016	Spectrum
GC-MS	Galactitol, non-derivatized, GC-MS Spectrum	splash10-0gb9-1983000000-0a0dafcfea843fbb3c72	Spectrum
Predicted GC-MS	Galactitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-03k9-9400000000-7a0f08ea65cbca1920f5	Spectrum
Predicted GC-MS	Galactitol, 6 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a6s-7141193000-dcd9245e12314ee0ced4	Spectrum
Predicted GC-MS	Galactitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_1_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_1_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_1_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_4, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_5, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_6, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_7, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_8, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_9, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_10, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Galactitol, TMS_2_11, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-005a-5900000000-35da0de23de5b9170aed	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0a4i-9000000000-552b84764ceb9b497a7e	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-052f-9000000000-dfb4eef021d94d514588	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 4V, negative	splash10-001i-0900000000-028ff289dc870279e218	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 8V, negative	splash10-001i-1900000000-a99ee988b2a1bbab9137	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 12V, negative	splash10-0uyr-6900000000-04315425478b660c8947	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 16V, negative	splash10-0kg9-9400000000-54350b0516f39f8c9b50	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - QqQ 20V, negative	splash10-0abi-9100000000-b4cf2b00830b765d5dcb	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0089-9000000000-20463a683f8ab7aa9e4d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0a4i-9000000000-5c4795e954d5c3e9b74e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0udi-0900000000-43b7e571c1185de1e99b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-00di-9000000000-160eaf7ef39d08853738	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0udi-3900000000-3114e2bfe0cdbc68be19	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-000j-9000000000-635a869063bea88c0091	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0uk9-3900000000-2ecc694b3a9844ec3ee5	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-03di-0900000000-61d17fd37e0e3ac16e37	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-03di-1900000000-90b308bca6baee5ab018	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0ik9-2900000000-eb87481835668a3b0d3d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0w29-5900000000-a78bc11bf7d88c2b913e	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-0udi-8900000000-0ae9e05f3f4517635bba	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-0zmi-9500000000-4156ee30d358f68b2590	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0udi-3900000000-0370fdfaee1df82b525d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-05fr-9000000000-9699f16da2c5fbaef32d	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-000j-9000000000-0a119385f247c8ed7ae4	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-014i-0490000000-403aabe62ebe0fa60ab3	2020-07-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum