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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-22 15:12:20 UTC
Update Date2017-12-07 01:49:53 UTC
HMDB IDHMDB0002928
Secondary Accession Numbers
  • HMDB02928
Metabolite Identification
Common NameMaltitol
DescriptionMaltitol is a sugar alcohol (polyol) used as a sugar substitute. It has 90% the sweetness of sugar and nearly identical properties, except for browning. It is used to very easily replace sugar and has less food energy, does not promote tooth decay and has a somewhat lower blood sugar response. Unfortunately, maltitol is well known to cause gastric distress, particularly if consumed in great quantities. Chemically, maltitol is also known as 4-O-alpha-Glucopyranosyl-D-sorbitol. Commercially, it is known under trade names such as Maltisorb and Maltisweet. Due to its slow absorption, excessive consumption of Maltitol can have laxative effect and often can cause gas and/or bloating. Maltitol is particularly demonized regarding gastric side effects because it is so easy for food producers to use it in vast quantities (due to its amazingly sugar-like properties) so consumers often end up consuming far more than they could most other sugar alcohols. While this is a major problem with maltitol, many sugar alcohols are far more likely to cause gastric distress than maltitol when compared gram-for-gram. -- Wikipedia.
Structure
Thumb
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 Number585-88-6
SMILES
[H][C@@](O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)([C@H](O)CO)[C@H](O)[C@@H](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/t4-,5+,6+,7+,8+,9-,10+,11+,12+/m0/s1
InChI KeyVQHSOMBJVWLPSR-WUJBLJFYSA-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

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point147 - 153 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot 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
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 (predicted from logP)
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)Download (PDF)
General References
  1. Makinen KK, Soderling E, Peacor DR, Makinen PL, Park LM: Carbohydrate-controlled precipitation of apatite with coprecipitation of organic molecules in human saliva: stabilizing role of polyols. Calcif Tissue Int. 1989 Apr;44(4):258-68. [PubMed:2501008 ]
  2. Makinen KK, Olak J, Russak S, Saag M, Seedre T, Vasar R, Vihalemm T, Mikelsaar M, Makinen PL: Polyol-combinant saliva stimulants: a 4-month pilot study in young adults. Acta Odontol Scand. 1998 Apr;56(2):90-4. [PubMed:9669459 ]
  3. Hall NA, Patrick AD: A high-performance liquid chromatography method for the analysis of picomole amounts of oligosaccharides. Anal Biochem. 1989 May 1;178(2):378-84. [PubMed:2751099 ]
  4. Oku T, Akiba M, Lee MH, Moon SJ, Hosoya N: Metabolic fate of ingested [14C]-maltitol in man. J Nutr Sci Vitaminol (Tokyo). 1991 Oct;37(5):529-44. [PubMed:1802977 ]
  5. Secchi A, Pontiroli AE, Cammelli L, Bizzi A, Cini M, Pozza G: Effects of oral administration of maltitol on plasma glucose, plasma sorbitol, and serum insulin levels in man. Klin Wochenschr. 1986 Mar 17;64(6):265-9. [PubMed:3520129 ]