ContaminantDB: Isomalt

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-05-22 03:27:54 UTC

Update Date

2016-11-09 01:15:22 UTC

Accession Number

CHEM016332

Identification

Common Name

Isomalt

Class

Small Molecule

Description

Isomalt is a sugar substitute, a type of sugar alcohol used primarily for its sugar-like physical properties. It has little to no impact on blood sugar levels, and does not stimulate the release of insulin. It also does not promote tooth decay, i.e. is tooth-friendly. Its energy value is 2 kcal/g, half that of sugars. However, like most sugar alcohols, it carries a risk of gastric distress, including flatulence and diarrhea, when consumed in large quantities (above about 20-30 g per day). Isomalt may prove upsetting to the intestinal tract because it is incompletely absorbed in the small intestine, and when polyols pass into the large intestine, they can cause osmotically induced diarrhea and stimulate the gut flora, causing flatulence. As with other dietary fibers, regular consumption of isomalt can lead to desensitisation, decreasing the risk of intestinal upset. Isomalt can be blended with high-intensity sweeteners such as sucralose, giving a mixture that has the same sweetness as sugar. Isomalt is an equimolar mixture of two mutually diastereomeric disaccharides, each composed of two sugars: glucose and mannitol (α-D-glucopyranosido-1,6-mannitol) and also glucose and sorbitol (α-D-glucopyranosido-1,6-sorbitol). Complete hydrolysis of isomalt yields glucose (50%), sorbitol (25%), and mannitol (25%). It is an odorless, 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, in particular, xylitol and erythritol. Isomalt is manufactured in a two-stage process in which sucrose is first transformed into isomaltulose, a reducing disaccharide (6-O-α-D-glucopyranosido-D-fructose). The isomaltulose is then hydrogenated, using a Raney nickel catalyst. The final product — isomalt — is an equimolar composition of 6-O-α-D-glucopyranosido-D-sorbitol (1,6-GPS) and 1-O-α-D-glucopyranosido-D-mannitol-dihydrate (1,1-GPM-dihydrate). Isomalt has been approved for use in the United States since 1990. It is also permitted for use in Australia, New Zealand, Canada, Mexico, Iran, the European Union, and other countries.

Contaminant Sources

ToxCast & Tox21 Chemicals

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
D-Glucitol, 6-O-alpha-D-glucopyranosyl-, mixt. with 1-O-alpha-D-glucopyranosyl-D-mannitol	MeSH
D-Glucitol, 6-O-alpha-D-glucopyranosyl-, mixture with 1-O-alpha-D-glucopyranosyl-D-mannitol	MeSH
BAY I 3930	ChEMBL

Chemical Formula

C₁₂H₂₄O₁₁

Average Molecular Mass

344.312 g/mol

Monoisotopic Mass

344.132 g/mol

CAS Registry Number

64519-82-0

IUPAC Name

(3R,4R,5R)-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexane-1,2,3,4,5-pentol

Traditional Name

isomalt

SMILES

[H]C(O)(CO)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)CO[C@@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@]([H])(O)[C@@]1([H])O

InChI Identifier

InChI=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/t4?,5-,6-,7-,8-,9-,10+,11-,12+/m1/s1

InChI Key

SERLAGPUMNYUCK-BLEZHGCXSA-N

Chemical Taxonomy

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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl glycosides

Direct Parent

Fatty 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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	315 g/L	ALOGPS
logP	-3.1	ALOGPS
logP	-5.5	ChemAxon
logS	-0.04	ALOGPS
pKa (Strongest Acidic)	12.06	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	200.53 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	70.82 m³·mol⁻¹	ChemAxon
Polarizability	32.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	0	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (9 TMS)	splash10-0uxr-0961000000-9e1d9919fd01f1a276bf	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004j-2429000000-566fa40afdfb8242cd09	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03di-9531000000-2a65651e8e0fa8de4797	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dl-9420000000-b9f23579781370da5e56	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-07bo-7952000000-bba4691868723e7ed321	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-08p0-9641000000-ab2958743c71db68d10b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0lxx-9510000000-2e7d08f239be123106ed	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Isomalt

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

3034828

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Isomalt (CHEM016332)

Structure for CHEM016332: Isomalt