Common Name

Galactitol Description

Galactitol 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

Synonyms

Value Source (2R,3S,4R,5S)-Hexane-1,2,3,4,5,6-hexolChEBI D-DlicitolChEBI D-GalactitolChEBI DlicitolChEBI DlicoseChEBI EuonymitChEBI L-GalactitolChEBI MelampyrinChEBI MelampyritChEBI Ambap5938HMDB DliciteHMDB HexitolHMDB MelampyriteHMDB MelampyrumHMDB meso-GalactitolHMDB

Chemical Formlia

C6H14O6 Average Molecliar Weight

182.1718 Monoisotopic Molecliar Weight

182.07903818 IUPAC Name

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

galactitol CAS Registry Number

608-66-2 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 Key

FBPFZTCFMRRESA-GUCUJZIJSA-N Chemical Taxonomy Classification

Not classified Ontology Status

Detected and Quantified Origin

  • Endogenous
  • Food
  • Biofunction

  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Application

  • Nutrients
  • Stabilizers
  • Surfactants and Emlisifiers
  • Cellliar locations

  • Extracellliar
  • Membrane
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference 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

    Property Value Source 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 Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key GC-MS

    GC-MS Spectrum – GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-014j-0941000000-61141f9f2ddc66e0b016View in MoNA GC-MS

    GC-MS Spectrum – GC-MS (6 TMS)splash10-0gb9-1983000000-0a0dafcfea843fbb3c72View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, N/A (Annotated)splash10-005a-5900000000-35da0de23de5b9170aedView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9000000000-552b84764ceb9b497a7eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, N/A (Annotated)splash10-052f-9000000000-dfb4eef021d94d514588View in MoNA 1D NMR

    1H NMR SpectrumNot Available 1D NMR

    13C NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Extracellliar
  • Membrane
  • Biofluid Locations

  • Amniotic Fluid
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Saliva
  • Urine
  • Tissue Location

  • Brain
  • Erythrocyte
  • Eye Lens
  • Lens
  • Pathways

    Name SMPDB Link KEGG Link Galactose MetabolismSMP00043map00052 GalactosemiaSMP00182Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details Amniotic FluidDetected and Quantified0.7 +/- 0.18 uMNot SpecifiedBothNormal

  • 6433315
  • details BloodDetected and Quantified0.82 (0.05 – 2.63) uMAdlit (>18 years old)BothNormal

  • 6434200
  • details BloodDetected and Quantified0.36 (0.23-0.48) uMAdlit (>18 years old)BothNormal

  • 7710082
  • details Cerebrospinal Fluid (CSF)Detected and Quantified1.65 +/- 0.44 uMAdlit (>18 years old)BothNormal

  • 8595727
  • details Cerebrospinal Fluid (CSF)Detected and Quantified1.82 (1.17-2.47) uMAdlit (>18 years old)BothNormal

  • 7710082
  • details FecesDetected but not Quantified Adlit (>18 years old)Both

    Normal

  • 21330412
  • details SalivaDetected and Quantified19.44 +/- 4.95 uMAdlit (>18 years old)BothNormal

  • Zerihun T. Dame, …
  • details UrineDetected and Quantified42 (3-81) umol/mmol creatinineAdlit (>18 years old)BothNormal

  • 7671965
  • details UrineDetected and Quantified3.7 (0.0-12.0) umol/mmol creatinineAdlit (>18 years old)Both

    Normal

  • Geigy Scientific …
  • details UrineDetected but not Quantified Adlit (>18 years old)BothNormal

  • 21389975
  • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details Amniotic FluidDetected and Quantified7.96 uMAdlit (>18 years old)BothGalactosemia

  • 6433315
  • details BloodDetected and Quantified11.63 +/- 0.46 uMAdlit (>18 years old)Both

    Galactosemia

  • 11092512
  • details Cerebrospinal Fluid (CSF)Detected and Quantified1.65 +/- 0.22 uMAdlit (>18 years old)BothAlzheimers disease

  • 8595727
  • details FecesDetected but not Quantified Adlit (>18 years old)Both

    Irritable bowel syndrome

  • 21330412
  • details UrineDetected and Quantified38500 (8000-69000) umol/mmol creatinineAdlit (>18 years old)BothGalactosemia

  • 7671965
  • details UrineDetected and Quantified472.5 (45-900) umol/mmol creatinineAdlit (>18 years old)Both

    Galactosemia

  • 7671965
  • details

    Associated Disorders and Diseases Disease References

    Alzheimers 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. [PubMed:8595727 ]

    Galactosemia type 1

    1. Jakobs C, Schweitzer S, Dorland B: Galactitol in galactosemia. Eur J Pediatr. 1995;154(7 Suppl 2):S50-2. [PubMed: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. [PubMed: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. [PubMed:6433315 ]

    Associated OMIM IDs

  • 104300 (Alzheimer's disease)
  • 230400 (Galactosemia type 1)
  • External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB006453 KNApSAcK ID

    C00001160 Chemspider ID

    11357 KEGG Compound ID

    C01697 BioCyc ID

    15-DIDEOXY-15-IMINO-D-GALACTITOL BiGG ID

    38183 Wikipedia Link

    Galactitol NuGOwiki Link

    HMDB00107 Metagene Link

    HMDB00107 METLIN ID

    5148 PubChem Compound

    11850 PDB ID

    Not Available ChEBI ID

    16813

    Product: Nicaraven

    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. 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. [PubMed: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. [PubMed: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. [PubMed:10926297 ]
    4. 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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed:15670721 ]
    8. Jakobs C, Schweitzer S, Dorland B: Galactitol in galactosemia. Eur J Pediatr. 1995;154(7 Suppl 2):S50-2. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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. [PubMed: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 + NAD details Beta-D-Galactose + NADPH + Hydrogen Ion → Galactitol + NADP details
    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 + NAD details Beta-D-Galactose + NADPH + Hydrogen Ion → Galactitol + NADP details

    PMID: 11429150