You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-13 02:07:08 UTC
HMDB IDHMDB00107
Secondary Accession NumbersNone
Metabolite Identification
Common NameGalactitol
DescriptionGalactitol is a naturally occurring product of plants obtained following reduction of galactose. It appears as a white crystalline powder with a slight sweet taste. It may form in excess in the lens of the eye in galactosemias a deficiency of galactokinase.
Structure
Thumb
Synonyms
ValueSource
D-DulcitolChEBI
D-GalactitolChEBI
DulcitolChEBI
DulcoseChEBI
EuonymitChEBI
L-GalactitolChEBI
MelampyrinChEBI
MelampyritChEBI
Ambap5938HMDB
DulciteHMDB
HexitolHMDB
MelampyriteHMDB
MelampyrumHMDB
meso-GalactitolHMDB
Chemical FormulaC6H14O6
Average Molecular Weight182.1718
Monoisotopic Molecular Weight182.07903818
IUPAC Name(2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional Namegalactitol
CAS Registry Number608-66-2
SMILES
OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO
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 KeyInChIKey=FBPFZTCFMRRESA-GUCUJZIJSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganooxygen compounds
ClassCarbohydrates and carbohydrate conjugates
Sub ClassSugar alcohols
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Secondary alcohol
  • Polyol
  • 1,2-diol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point189.5 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility31,0 mg/mL at 15 °CYALKOWSKY,SH & DANNENFELSER,RM (1992)
LogP-3.10HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility229.0 mg/mLALOGPS
logP-2.7ALOGPS
logP-3.7ChemAxon
logS0.1ALOGPS
pKa (Strongest Acidic)12.59ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area121.38 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.4 m3·mol-1ChemAxon
Polarizability17.25 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014j-0941000000-61141f9f2ddc66e0b016View in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0gb9-1983000000-0a0dafcfea843fbb3c72View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-005a-5900000000-35da0de23de5b9170aedView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9000000000-552b84764ceb9b497a7eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-052f-9000000000-dfb4eef021d94d514588View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Amniotic Fluid
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
Tissue Location
  • Brain
  • Erythrocyte
  • Eye Lens
  • Lens
Pathways
NameSMPDB LinkKEGG Link
Galactose MetabolismSMP00043map00052
GalactosemiaSMP00182Not Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Amniotic FluidDetected and Quantified0.7 +/- 0.18 uMNot SpecifiedBothNormal details
BloodDetected and Quantified0.82 (0.05 - 2.63) uMAdult (>18 years old)BothNormal details
BloodDetected and Quantified0.36 (0.23-0.48) uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.65 +/- 0.44 uMAdult (>18 years old)BothNormal details
Cerebrospinal Fluid (CSF)Detected and Quantified1.82 (1.17-2.47) uMAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Normal
details
SalivaDetected and Quantified19.44 +/- 4.95 uMAdult (>18 years old)BothNormal
    • Zerihun T. Dame, ...
details
UrineDetected and Quantified42 (3-81) umol/mmol creatinineAdult (>18 years old)BothNormal details
UrineDetected and Quantified3.7 (0.0-12.0) umol/mmol creatinineAdult (>18 years old)Both
Normal
    • Geigy Scientific ...
details
UrineDetected but not QuantifiedNot ApplicableAdult (>18 years old)BothNormal details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
Amniotic FluidDetected and Quantified7.96 uMAdult (>18 years old)BothGalactosemia details
BloodDetected and Quantified11.63 +/- 0.46 uMAdult (>18 years old)Both
Galactosemia
details
Cerebrospinal Fluid (CSF)Detected and Quantified1.65 +/- 0.22 uMAdult (>18 years old)BothAlzheimer's disease details
FecesDetected but not QuantifiedNot ApplicableAdult (>18 years old)Both
Irritable bowel syndrome
details
UrineDetected and Quantified38500 (8000-69000) umol/mmol creatinineAdult (>18 years old)BothGalactosemia details
UrineDetected and Quantified472.5 (45-900) umol/mmol creatinineAdult (>18 years old)Both
Galactosemia
details
Associated Disorders and Diseases
Disease References
Alzheimer's disease
  1. Shetty HU, Holloway HW, Schapiro MB: Cerebrospinal fluid and plasma distribution of myo-inositol and other polyols in Alzheimer disease. Clin Chem. 1996 Feb;42(2):298-302. [8595727 ]
Galactosemia type 1
  1. Jakobs C, Schweitzer S, Dorland B: Galactitol in galactosemia. Eur J Pediatr. 1995;154(7 Suppl 2):S50-2. [7671965 ]
  2. 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 ]
  3. 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 ]
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB006453
KNApSAcK IDC00001160
Chemspider ID11357
KEGG Compound IDC01697
BioCyc ID15-DIDEOXY-15-IMINO-D-GALACTITOL
BiGG ID38183
Wikipedia LinkGalactitol
NuGOwiki LinkHMDB00107
Metagene LinkHMDB00107
METLIN ID5148
PubChem Compound11850
PDB IDNot Available
ChEBI ID16813
References
Synthesis ReferenceMuniruzzaman, Syed; Itoh, Hiromichi; Yoshino, Akira; Katayama, Takeshi; Izumori, Ken. Biotransformation of lactose to galactitol. Journal of Fermentation and Bioengineering (1994), 77(1), 32-5.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. Budde M, Gusek-Schneider GC, Junemann A, Jansen F, Shin YS: [Familial cataract in plasma galactitol increase without known enzyme defect] Klin Monatsbl Augenheilkd. 1999 Oct;215(4):255-7. [10572890 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. Jakobs C, Schweitzer S, Dorland B: Galactitol in galactosemia. Eur J Pediatr. 1995;154(7 Suppl 2):S50-2. [7671965 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NADPH-dependent reduction of a wide variety of carbonyl-containing compounds to their corresponding alcohols with a broad range of catalytic efficiencies.
Gene Name:
AKR1B1
Uniprot ID:
P15121
Molecular weight:
35853.125
Reactions
Beta-D-Galactose + NADH + Hydrogen Ion → Galactitol + NADdetails
Beta-D-Galactose + NADPH + Hydrogen Ion → Galactitol + NADPdetails
General function:
Not Available
Specific function:
Acts as all-trans-retinaldehyde reductase. Can efficiently reduce aliphatic and aromatic aldehydes, and is less active on hexoses (in vitro). May be responsible for detoxification of reactive aldehydes in the digested food before the nutrients are passed on to other organs.
Gene Name:
AKR1B10
Uniprot ID:
O60218
Molecular weight:
Not Available
Reactions
Beta-D-Galactose + NADH + Hydrogen Ion → Galactitol + NADdetails
Beta-D-Galactose + NADPH + Hydrogen Ion → Galactitol + NADPdetails