Record Information
Version1.0
Creation date2010-04-08 22:04:51 UTC
Update date2015-07-20 21:38:19 UTC
Primary IDFDB001164
Secondary Accession Numbers
  • FDB003189
Chemical Information
FooDB Name1-O-alpha-D-Glucopyranosyl-D-mannitol
DescriptionLow nutritive sweetener with half sweetness of sucrose. Component of *Isomalt* Isomalt is a disaccharide composed of the two sugars glucose and mannitol. It is an odourless, white, crystalline substance containing about 5% water of crystallisation. Isomalt has a minimal cooling effect (positive heat of solution), lower than many other sugar alcohols, particularly xylitol and erythritol. Isomalt is unusual as it is a natural sugar alcohol that is produced from beets. An interesting use of isomalt is found in the product DiabetiSweet, a sugar substitute sold for baking use and composed of a blend of isomalt and acesulfame potassium, but it has a bitter taste (due to the acesulfame potassium) and lacks the caramelizing properties of sugar.; Isomalt is a sugar substitute, a type of sugar alcohol, which is primarily used for its sugar-like physical properties. It has only a small impact on blood sugar levels and does not promote tooth decay. It has 2 kcal/g, half the calories of sugars. However, like most sugar alcohols, it carries a very real risk of gastric distress, including flatulence and diarrhea, when consumed in large quantities. And due to its laxative properties Isomalt is advised to not be consumed in quantities larger than about 50g per day for adults and 25g for children. The reason that isomalt may prove upsetting to the stomach is because the body recognizes it as a dietary fiber instead of as a simple carbohydrate. Therefore, like most fibers, it can increase bowel movements and it passes through the bowel in virtually undigested form. Like other dietary fibers, regular consumption of isomalt might eventually lead one to become desensitized to it, decreasing the risk of stomach upset. Isomalt is typically blended with a high intensity sweetener such as sucralose, so that the mixture has approximately the sweetness of sugar.
CAS Number20942-99-8
Structure
Thumb
Synonyms
SynonymSource
1-O-a-D-Glucopyranosyl-D-mannitolGenerator
1-O-Α-D-glucopyranosyl-D-mannitolGenerator
1-O-beta-D-Glucopyranosyl-D-mannitolHMDB
e953HMDB
GPMHMDB
IsomaltHMDB
1,6-Sorbitol glucopyranosideHMDB
D-Glucitol, 6-O-alpha-D-glucopyranosyl-, mixture with 1-O-alpha-D-glucopyranosyl-D-mannitolMeSH
D-Glucitol, 6-O-alpha-D-glucopyranosyl-, mixt. with 1-O-alpha-D-glucopyranosyl-D-mannitolMeSH
1-O-alpha-D-Glucopyranosyl-D-mannitolbiospider
1-O-beta-D-glucopyranosyl-D-mannitolbiospider
D-Mannitol, 1-O-alpha-D-glucopyranosyl-biospider
E953db_source
Predicted Properties
PropertyValueSource
Water Solubility315 g/LALOGPS
logP-3.1ALOGPS
logP-5.5ChemAxon
logS-0.04ALOGPS
pKa (Strongest Acidic)12.06ChemAxon
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
Polarizability32.34 ųChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC12H24O11
IUPAC name6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexane-1,2,3,4,5-pentol
InChI IdentifierInChI=1S/C12H24O11/c13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h4-21H,1-3H2
InChI KeySERLAGPUMNYUCK-UHFFFAOYSA-N
Isomeric SMILESOCC(O)C(O)C(O)C(O)COC1OC(CO)C(O)C(O)C1O
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
  • Glycosyl compound
  • O-glycosyl compound
  • Fatty alcohol
  • Sugar alcohol
  • Monosaccharide
  • 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
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 41.86%; H 7.03%; O 51.11%DFC
Melting PointMp 122-125°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]20D +87.3 (c, 0.2 in H2O)DFC
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID88735
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDBVD34-B:BVD35-C
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDrw1609041
SuperScent IDNot Available
Wikipedia IDIsomalt
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
Flavours
FlavorCitations
odorless
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference