Record Information
Version2.0
Creation Date2012-05-31 09:57:27 -0600
Update Date2015-06-03 15:53:12 -0600
Secondary Accession Numbers
  • ECMDB00107
Identification
Name:Galactitol
Description:Galactitol, also called dulcitol, is a sugar alcohol, the reduction product of galactose. Galactitol is produced from galactose in a reaction catalyzed by aldose reductase. Galactose itself comes from the metabolism of the disaccharide lactose into glucose and galactose (Wikipedia). It appears as a white crystalline powder with a slight sweet taste.
Structure
Thumb
Synonyms:
  • Ambap5938
  • D-Dulcitol
  • Dulcite
  • Dulcitol
  • Dulcose
  • Euonymit
  • Galactitol
  • Hexitol
  • Melampyrin
  • Melampyrit
  • Melampyrite
  • Melampyrum
  • Meso-galactitol
Chemical Formula:C6H14O6
Weight:Average: 182.1718
Monoisotopic: 182.07903818
InChI Key:FBPFZTCFMRRESA-GUCUJZIJSA-N
InChI:InChI=1S/C6H14O6/c7-1-3(9)5(11)6(12)4(10)2-8/h3-12H,1-2H2/t3-,4+,5+,6-
CAS number:608-66-2
IUPAC Name:(2R,3S,4R,5S)-hexane-1,2,3,4,5,6-hexol
Traditional IUPAC Name:galactitol
SMILES:OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO
Chemical Taxonomy
ClassificationNot classified
Physical Properties
State:Solid
Charge:0
Melting point:189.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:31 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]; 31.0 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
LogP:-3.10 [HANSCH,C ET AL. (1995)]PhysProp
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
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Galactitol and galactonate degradationPW000820 Pw000820Pw000820 greyscalePw000820 simple
Galactose metabolismPW000821 Pw000821Pw000821 greyscalePw000821 simple
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
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
GC-MSGC-MS Spectrum - GC-MSsplash10-03k9-9400000000-7a0f08ea65cbca1920f5View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOFsplash10-014j-0941000000-61141f9f2ddc66e0b016View in MoNA
GC-MSGC-MS Spectrum - GC-MSsplash10-0gb9-1983000000-0a0dafcfea843fbb3c72View in MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0a6s-7141193000-dcd9245e12314ee0ced4View 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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-1900000000-8fd623cab2d92c8fe6bcView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-9100000000-6b1add40ffbd73109f44View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03dl-9000000000-91a1337ee99558df9b9bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00su-8900000000-bab2cfe2d89285b51d20View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06y6-9100000000-d4d223d12ef78c8ca224View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0btc-9000000000-9c0d6465be9cdfd04388View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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. Pubmed: 2533041
  • 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. Pubmed: 7214715
  • 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. Pubmed: 1597290
  • 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. Pubmed: 11174626
  • 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. Pubmed: 8487507
  • 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. Pubmed: 10572890
  • 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. Pubmed: 15670721
  • Jakobs C, Schweitzer S, Dorland B: Galactitol in galactosemia. Eur J Pediatr. 1995;154(7 Suppl 2):S50-2. Pubmed: 7671965
  • 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. Pubmed: 6433315
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • 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. Pubmed: 10926297
  • 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. Pubmed: 11092512
  • 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. Pubmed: 7448335
  • 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. Pubmed: 6434200
  • 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. Pubmed: 3971562
  • 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. Pubmed: 7710082
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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.
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID16813
HMDB IDHMDB00107
Pubchem Compound ID11850
Kegg IDC01697
ChemSpider ID11357
WikipediaGalactitol
BioCyc IDGALACTITOL
EcoCyc IDGALACTITOL

Enzymes

General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatC
Uniprot ID:
P69831
Molecular weight:
48365
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatB
Uniprot ID:
P37188
Molecular weight:
10222
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatA
Uniprot ID:
P69828
Molecular weight:
16907
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. The phosphoryl group from phosphoenolpyruvate (PEP) is transferred to the phosphoryl carrier protein HPr by enzyme I. Phospho-HPr then transfers it to the permease (enzymes II/III)
Gene Name:
ptsH
Uniprot ID:
P0AA04
Molecular weight:
9119
Reactions
Protein HPr N(pi)-phospho-L-histidine + protein EIIA = protein HPr + protein EIIA N(tau)-phospho-L-histidine.
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
General (non sugar-specific) component of the phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS). This major carbohydrate active-transport system catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. Enzyme I transfers the phosphoryl group from phosphoenolpyruvate (PEP) to the phosphoryl carrier protein (HPr)
Gene Name:
ptsI
Uniprot ID:
P08839
Molecular weight:
63561
Reactions
Phosphoenolpyruvate + protein L-histidine = pyruvate + protein N(pi)-phospho-L-histidine.
General function:
Involved in transporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane
Gene Name:
sgcA
Uniprot ID:
P39363
Molecular weight:
15638
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane
Gene Name:
sgcB
Uniprot ID:
P58035
Molecular weight:
9803
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane
Gene Name:
sgcC
Uniprot ID:
P39365
Molecular weight:
46684

Transporters

General function:
Involved in transporter activity
Specific function:
Uptake of inorganic phosphate, phosphorylated compounds, and some other negatively charged solutes
Gene Name:
phoE
Uniprot ID:
P02932
Molecular weight:
38922
General function:
Involved in transporter activity
Specific function:
OmpF is a porin that forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane. It is also a receptor for the bacteriophage T2
Gene Name:
ompF
Uniprot ID:
P02931
Molecular weight:
39333
General function:
Involved in transporter activity
Specific function:
Non-specific porin
Gene Name:
ompN
Uniprot ID:
P77747
Molecular weight:
41220
General function:
Involved in transporter activity
Specific function:
Forms passive diffusion pores which allow small molecular weight hydrophilic materials across the outer membrane
Gene Name:
ompC
Uniprot ID:
P06996
Molecular weight:
40368
General function:
Involved in phosphoenolpyruvate-dependent sugar phosphotransferase system
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitant with their translocation across the cell membrane. This system is involved in galactitol transport
Gene Name:
gatC
Uniprot ID:
P69831
Molecular weight:
48365