T3DB: Galactitol

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Gene Regulation XML

Record Information

Version

2.0

Creation Date

2014-08-29 06:31:18 UTC

Update Date

2018-03-21 17:46:18 UTC

Accession Number

T3D4349

Identification

Common Name

Galactitol

Class

Small Molecule

Description

Galactitol or dulcitol is a sugar alcohol that is a metabolic breakdown product of galactose. 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. Galactitol has a slightly sweet taste. It is produced from galactose in a reaction catalyzed by aldose reductase. 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.

Compound Type

Food Toxin
Metabolite
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Synonym
Ambap5938
D-Dulcitol
Dulcite
Dulcitol
Dulcose
Euonymit
Hexitol
Melampyrin
Melampyrit
Melampyrite
Melampyrum
Meso-galactitol

Chemical Formula

C₆H₁₄O₆

Average Molecular Mass

182.172 g/mol

Monoisotopic Mass

182.079 g/mol

CAS Registry Number

608-66-2

IUPAC Name

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

Traditional Name

galactitol

SMILES

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

InChI Identifier

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

InChI Key

InChIKey=FBPFZTCFMRRESA-GUCUJZIJNA-N

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

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

hexitol (CHEBI:16813 )

Biological Properties

Status

Detected and Not Quantified

Origin

Endogenous

Cellular Locations

Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Brain
Erythrocyte
Eye Lens
Lens

Pathways

Name	SMPDB Link	KEGG Link
Galactose Metabolism	SMP00043	map00052
Galactosemia	SMP00182	Not Available
Galactosemia II (GALK)	SMP00495	Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	189.5°C
Boiling Point	Not Available
Solubility	31,0 mg/mL at 15°C
LogP	-3.1

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-014j-0941000000-61141f9f2ddc66e0b016	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (6 TMS)	splash10-0gb9-1983000000-0a0dafcfea843fbb3c72	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-014j-0941000000-61141f9f2ddc66e0b016	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0gb9-1983000000-0a0dafcfea843fbb3c72	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03k9-9400000000-7a0f08ea65cbca1920f5	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (6 TMS) - 70eV, Positive	splash10-0a6s-7141193000-dcd9245e12314ee0ced4	2017-10-06	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-11-05	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-005a-5900000000-35da0de23de5b9170aed	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-0a4i-9000000000-552b84764ceb9b497a7e	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-052f-9000000000-dfb4eef021d94d514588	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 4V, negative	splash10-001i-0900000000-028ff289dc870279e218	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 8V, negative	splash10-001i-1900000000-a99ee988b2a1bbab9137	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 12V, negative	splash10-0uyr-6900000000-04315425478b660c8947	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 16V, negative	splash10-0kg9-9400000000-54350b0516f39f8c9b50	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - QqQ 20V, negative	splash10-0abi-9100000000-b4cf2b00830b765d5dcb	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0089-9000000000-20463a683f8ab7aa9e4d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0a4i-9000000000-5c4795e954d5c3e9b74e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0udi-0900000000-43b7e571c1185de1e99b	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-00di-9000000000-160eaf7ef39d08853738	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0udi-3900000000-3114e2bfe0cdbc68be19	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-000j-9000000000-635a869063bea88c0091	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0uk9-3900000000-2ecc694b3a9844ec3ee5	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 3V, negative	splash10-03di-0900000000-61d17fd37e0e3ac16e37	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, negative	splash10-03di-1900000000-90b308bca6baee5ab018	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, negative	splash10-0ik9-2900000000-eb87481835668a3b0d3d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, negative	splash10-0w29-5900000000-a78bc11bf7d88c2b913e	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, negative	splash10-0udi-8900000000-0ae9e05f3f4517635bba	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, negative	splash10-0zmi-9500000000-4156ee30d358f68b2590	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-0udi-3900000000-0370fdfaee1df82b525d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-05fr-9000000000-9699f16da2c5fbaef32d	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - n/a 12V, negative	splash10-000j-9000000000-0a119385f247c8ed7ae4	2020-07-22	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, negative	splash10-014i-0490000000-403aabe62ebe0fa60ab3	2020-07-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Not Available	2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, experimental)	Not Available	2021-10-10	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	2012-12-04	View Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Accumulation of galactitol in the body has been shown to be toxic. Accumulation of galactitol in the lens causes the osmotic phenomena and results in cataract formation. It may form in excess in the lens of the eye in galactosemias, a deficiency of galactokinase.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

This is an endogenously produced metabolite found in the human body. It is used in metabolic reactions, catabolic reactions or waste generation.

Minimum Risk Level

Not Available

Health Effects

Chronically high levels of galactitol are associated with at least 2 inborn errors of metabolism including: Galactosemia and Galactosemia type II.

Symptoms

Not Available

Treatment

Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

PubChem Compound ID

ChEMBL ID

ChemSpider ID

KEGG ID

UniProt ID

Not Available

OMIM ID

ChEBI ID

16813

BioCyc ID

15-DIDEOXY-15-IMINO-D-GALACTITOL

CTD ID

Not Available

Stitch ID

Not Available

PDB ID

Not Available

ACToR ID

Not Available

Wikipedia Link

Galactitol

References

Synthesis Reference

Muniruzzaman, Syed; Itoh, Hiromichi; Yoshino, Akira; Katayama, Takeshi; Izumori, Ken. Biotransformation of lactose to galactitol. Journal of Fermentation and Bioengineering (1994), 77(1), 32-5.

MSDS

T3D4349.pdf

General References

Ning C, Segal S: Plasma galactose and galactitol concentration in patients with galactose-1-phosphate uridyltransferase deficiency galactosemia: determination by gas chromatography/mass spectrometry. Metabolism. 2000 Nov;49(11):1460-6. [11092512 ]
Jakobs C, Warner TG, Sweetman L, Nyhan WL: Stable isotope dilution analysis of galactitol in amniotic fluid: an accurate approach to the prenatal diagnosis of galactosemia. Pediatr Res. 1984 Aug;18(8):714-8. [6433315 ]
Ning C, Reynolds R, Chen J, Yager C, Berry GT, McNamara PD, Leslie N, Segal S: Galactose metabolism by the mouse with galactose-1-phosphate uridyltransferase deficiency. Pediatr Res. 2000 Aug;48(2):211-7. [10926297 ]
Budde M, Gusek-Schneider GC, Junemann A, Jansen F, Shin YS: [Familial cataract in plasma galactitol increase without known enzyme defect]. Klin Monbl Augenheilkd. 1999 Oct;215(4):255-7. [10572890 ]
Berry GT, Hunter JV, Wang Z, Dreha S, Mazur A, Brooks DG, Ning C, Zimmerman RA, Segal S: In vivo evidence of brain galactitol accumulation in an infant with galactosemia and encephalopathy. J Pediatr. 2001 Feb;138(2):260-2. [11174626 ]
Pettit BR, King GS, Blau K: The analysis of hexitols in biological fluid by selected ion monitoring. Biomed Mass Spectrom. 1980 Jul;7(7):309-13. [7448335 ]
Ficicioglu C, Yager C, Segal S: Galactitol and galactonate in red blood cells of children with the Duarte/galactosemia genotype. Mol Genet Metab. 2005 Feb;84(2):152-9. Epub 2004 Dec 9. [15670721 ]
Jakobs C, Schweitzer S, Dorland B: Galactitol in galactosemia. Eur J Pediatr. 1995;154(7 Suppl 2):S50-2. [7671965 ]
Roboz J, Kappatos DC, Greaves J, Holland JF: Determination of polyols in serum by selected ion monitoring. Clin Chem. 1984 Oct;30(10):1611-5. [6434200 ]
Airey CM, Price DE, Kemp JV, Perkins CM, Wales JK: The effect of aldose reductase inhibition on erythrocyte polyols and galactitol accumulation in diabetic patients. Diabet Med. 1989 Dec;6(9):804-8. [2533041 ]
Schwarz HP, Schaefer T, Bachmann C: Galactose and galactitol in the urine of children with compound heterozygosity for Duarte variant and classical galactosemia (GtD/gt) after an oral galactose load. Clin Chem. 1985 Mar;31(3):420-2. [3971562 ]
Arola H, Sillanaukee P, Aine E, Koivula T, Isokoski M: Galactitol is not a cause of senile cataract. Graefes Arch Clin Exp Ophthalmol. 1992;230(3):240-2. [1597290 ]
Allen JT, Holton JB, Gillett MG: Gas-liquid chromatographic determination of galactitol in amniotic fluid for possible use in prenatal diagnosis of galactosaemia. Clin Chim Acta. 1981 Feb 19;110(1):59-63. [7214715 ]
Shetty HU, Holloway HW, Rapoport SI: Capillary gas chromatography combined with ion trap detection for quantitative profiling of polyols in cerebrospinal fluid and plasma. Anal Biochem. 1995 Jan 1;224(1):279-85. [7710082 ]
Berry GT, Palmieri M, Gross KC, Acosta PB, Henstenburg JA, Mazur A, Reynolds R, Segal S: The effect of dietary fruits and vegetables on urinary galactitol excretion in galactose-1-phosphate uridyltransferase deficiency. J Inherit Metab Dis. 1993;16(1):91-100. [8487507 ]

Gene Regulation

Up-Regulated Genes

Not Available

Down-Regulated Genes

Not Available

Galactitol (T3D4349)

Structure for T3D4349: Galactitol