Record Information
Version1.0
Creation date2010-04-08 22:14:59 UTC
Update date2015-10-09 22:32:19 UTC
Primary IDFDB020369
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameMaltitoll
DescriptionPermitted bulk sweetener for foods Commercially, maltitol is a disaccharide produced by Corn Products Specialty Ingredients (formerly SPI Polyols), Cargill, Roquette, and Towa, among other companies. Maltitol is made by hydrogenation of maltose obtained from starch. Its high sweetness allows it to be used without being mixed with other sweeteners, and exhibits negligible cooling effect (positive heat of solution) in comparison with other sugar alcohols, and is very similar to the subtle cooling effect of sucrose. It is used especially in production of sweets: sugarless hard candies, chewing gum, chocolates, baked goods, and ice cream. The pharmaceutical industry uses maltitol as an excipient where it is utilised as a low-calorie sweetening agent. Its similarity to sucrose allows it to be used in syrups with the advantage that crystallization (which may cause bottle caps to stick) is less likely. Maltitol may also be used as a plasticiser in gelatine capsules, as an emollient, and as a humectant.; In countries such as Australia, Norway and New Zealand, it carries a mandatory warning such as "Excessive consumption may have a laxative effect." In the United States, it is a Generally recognized as safe (GRAS) substance, with a recommendation of a warning about its laxative potential when consumed at levels of 100 grams per day or more.; Maltitol is a sugar alcohol (a polyol) used as a sugar substitute. It has 75-90% of the sweetness of sucrose (table sugar) and nearly identical properties, except for browning. It is used to replace table sugar because it has fewer calories, does not promote tooth decay and has a somewhat lesser effect on blood glucose. Chemically, maltitol is also known as 4-O-?-glucopyranosyl-D-sorbitol. Commercially, it is known under trade names such as Maltisorb and Maltisweet.; Maltitol 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
CAS Number585-88-6
Structure
Thumb
Synonyms
SynonymSource
(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
WURCS=2.0/2,2,1/[H2122H][a2122h-1a_1-5]/1-2/a4-b1ChEBI
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
MaltitolHMDB
4-O-α-D-glucopyranosyl-D-glucitolGenerator
a-D-Glc-(1->4)-D-glc-olGenerator
a-D-Glcp-(1->4)-D-glc-olGenerator
alpha-D-Glc-(1->4)-D-glc-olChEBI
alpha-D-Glcp-(1->4)-D-glc-olChEBI
D-Glucitol, 4-O-alpha-D-glucopyranosyl-biospider
D-glucopyranosyl-d-glucitolbiospider
D-maltitolbiospider
Delta-maltitolbiospider
E965db_source
Glucitol, 4-O-alpha-D-glucopyranosyl-, D-biospider
α-D-glc-(1->4)-D-glc-olGenerator
α-D-glcp-(1->4)-D-glc-olGenerator
α-D-glucosyl-(1->4)-D-glucitolGenerator
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
Polarizability31.84 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC12H24O11
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
InChI IdentifierInChI=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
Isomeric SMILESOCC(O)C(O)C(OC1OC(CO)C(O)C(O)C1O)C(O)CO
Average Molecular Weight344.3124
Monoisotopic Molecular Weight344.13186161
Classification
Description Belongs to the class of organic compounds known as fatty acyl glycosides of mono- and disaccharides. Fatty acyl glycosides of mono- and disaccharides 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
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionC 41.86%; H 7.03%; O 51.11%DFC
Melting PointMp 149-152°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]21D +107 (c, 10 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MS, non-derivatized, GC-MS Spectrumsplash10-0uxs-0952000000-b7f978a79c1e8d933177Spectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03fr-9235000000-4b74058303ecc8c4b855Spectrum
Predicted GC-MS, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00kr-6460219000-7d7a8a9d3b52128e18e4Spectrum
Predicted GC-MS, TBDMS_3_50, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_3_52, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_57, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_59, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_72, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_73, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_92, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_93, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_94, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_95, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_96, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_99, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_100, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, TBDMS_4_112, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MS, "Maltitol,3TBDMS,#50" TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-001i-0900000000-4c268ca31754a92aadb7Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-014i-9400000000-2cbc4727d166702a8dcfSpectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-067r-9000000000-090e156d979b54105c93Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0h4x-8904000000-348f04d18d9ab4a54309Spectrum
MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-002f-1279000000-89dc38b09b82fe640e58Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0006-0009000000-74f3005b7f662c942544Spectrum
MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0002-0009000000-7d6f01e4ad770ea30d9eSpectrum
MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4j-0095000000-646de9a950331e2820f5Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0006-1190000000-0c5fa032896efc821669Spectrum
MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-066r-0090000000-9f1519336d06d1d75d44Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00o1-1908000000-27615cf754d66c0d1f21Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-02u0-4901000000-b99d2d4b0115fe5091aeSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03xu-9810000000-6b21bfaddbf77f03a7b3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-7694000000-a6af66a19f9a31c099b8Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01u0-6931000000-12750896e8c10d0fcbc3Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-08fu-9700000000-156a606db9a67ec92434Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-054k-0209000000-281f58cfa23a6a50f0f7Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9701000000-fd1529eaf380bfa9e951Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000w-9400000000-bea21dfb9029812122e5Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1129000000-2c95ce6a3d2cfa92e02aSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-9451000000-84f94577e31c56237ec2Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9100000000-3350e8567bb71f6704d0Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID432001
ChEMBL IDCHEMBL63558
KEGG Compound IDNot Available
Pubchem Compound ID493591
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB02928
CRC / DFC (Dictionary of Food Compounds) IDMRC76-Z:MRC76-Z
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDMaltitol
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference