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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-12 02:33:00 UTC
Update Date2019-01-11 20:00:00 UTC
HMDB IDHMDB0040937
Secondary Accession Numbers
  • HMDB40937
Metabolite Identification
Common NameLactitol
DescriptionLactitol is found in herbs and spices. Artificial sweetener used in foods. Sweetness 0.4 x sucrose.Lactitol is a sugar alcohol used as a replacement bulk sweetener for low calorie foods with approximately 40% of the sweetness of sugar. Lactitol is produced by two manufacturers, Danisco and Purac Biochem
Structure
Data?1547236800
Synonyms
ValueSource
(2S,3R,4R,5R)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl]oxy}hexane-1,2,3,5,6-pentolChEBI
4-O-alpha-D-Glucopyranosyl-D-glucitolChEBI
alpha-D-GLC-(1->4)-D-GLC-olChEBI
alpha-D-GLCP-(1->4)-D-GLC-olChEBI
alpha-D-Glucosyl-(1->4)-D-glucitolChEBI
D-MaltitolChEBI
4-O-a-D-Glucopyranosyl-D-glucitolGenerator
4-O-α-D-glucopyranosyl-D-glucitolGenerator
a-D-GLC-(1->4)-D-GLC-olGenerator
α-D-GLC-(1->4)-D-GLC-olGenerator
a-D-GLCP-(1->4)-D-GLC-olGenerator
α-D-GLCP-(1->4)-D-GLC-olGenerator
a-D-Glucosyl-(1->4)-D-glucitolGenerator
α-D-glucosyl-(1->4)-D-glucitolGenerator
4-O-alpha-delta-Glucopyranosyl-delta-glucitolHMDB
Amalti syrupHMDB
Amalty MR 100HMDB
D-4-O-alpha-D-GlucopyranosylglucitolHMDB
delta-4-O-alpha-delta-GlucopyranosylglucitolHMDB
delta-MaltitolHMDB
MalbitHMDB
Malti MRHMDB
MaltisorbHMDB
MaltitHMDB
Chemical FormulaC12H24O11
Average Molecular Weight344.3124
Monoisotopic Molecular Weight344.13186161
IUPAC Name(2S,3R,4R,5R)-4-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexane-1,2,3,5,6-pentol
Traditional Namemaltitol
CAS Registry Number585-86-4
SMILES
OCC(O)C(O)C(OC1OC(CO)C(O)C(O)C1O)C(O)CO
InChI Identifier
InChI=1S/C12H24O11/c13-1-4(16)7(18)11(5(17)2-14)23-12-10(21)9(20)8(19)6(3-15)22-12/h4-21H,1-3H2
InChI KeyVQHSOMBJVWLPSR-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. These are compounds composed of a mono- or disaccharide moiety linked to one hydroxyl group of a fatty alcohol or of a phosphorylated alcohol (phosphoprenols), a hydroxy fatty acid or to one carboxyl group of a fatty acid (ester linkage) or to an amino alcohol.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl glycosides
Direct ParentFatty acyl glycosides of mono- and disaccharides
Alternative Parents
Substituents
  • Fatty acyl glycoside of mono- or disaccharide
  • Alkyl glycoside
  • Disaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Sugar alcohol
  • Oxane
  • Secondary alcohol
  • Acetal
  • Organoheterocyclic compound
  • Oxacycle
  • Polyol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point95 - 98 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility667 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility377 g/LALOGPS
logP-3.2ALOGPS
logP-5.5ChemAxon
logS0.04ALOGPS
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area200.53 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity70.82 m³·mol⁻¹ChemAxon
Polarizability31.73 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0uxs-0952000000-b7f978a79c1e8d933177View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03fr-9235000000-4b74058303ecc8c4b855View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00kr-6460219000-7d7a8a9d3b52128e18e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-4c268ca31754a92aadb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9400000000-2cbc4727d166702a8dcfView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-067r-9000000000-090e156d979b54105c93View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0h4x-8904000000-348f04d18d9ab4a54309View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00o1-1908000000-27615cf754d66c0d1f21View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02u0-4901000000-b99d2d4b0115fe5091aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-9810000000-6b21bfaddbf77f03a7b3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-7694000000-a6af66a19f9a31c099b8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01u0-6931000000-12750896e8c10d0fcbc3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-9700000000-156a606db9a67ec92434View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB020369
KNApSAcK IDNot Available
Chemspider ID432001
KEGG Compound IDNot Available
BioCyc IDCPD-3609
BiGG IDNot Available
Wikipedia LinkMaltitol
METLIN ID3484
PubChem Compound493591
PDB IDNot Available
ChEBI ID68428
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Marotta F, Geng TC, Wu CC, Barbi G: Bacterial translocation in the course of acute pancreatitis: beneficial role of nonabsorbable antibiotics and lactitol enemas. Digestion. 1996 Nov-Dec;57(6):446-52. [PubMed:8913707 ]
  2. Egger B, Arnera V, Llull JB, Lauterburg BH: Effect of one month of lactitol treatment on calcium metabolism in man. Eur J Clin Pharmacol. 1989;37(2):205-7. [PubMed:2792176 ]
  3. Saphronova LA, Osadchaia AI, Iliash VM: [Prebiotic lactitol as a component of biopreparation from aerobic bacilli]. Mikrobiol Z. 2008 Nov-Dec;70(6):34-41. [PubMed:19351047 ]
  4. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  5. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  6. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  7. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  8. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  9. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.