Isomalt

Isomalt is a sugar substitute, a mixture of the two disaccharide alcohols 1,6-GPS and 1,1-GPM. It is 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 and is considered to be tooth-friendly. Its energy value is 2 kcal per gram, half that of sugars. It is less sweet than sugar, but can be blended with high-intensity sweeteners such as sucralose to create a mixture with the same sweetness as sucrose (‘sugar’).

For a disaccharide derived from sucrose, see isomaltulose. For a disaccharide derived from maltose, see isomaltose.
Isomalt

Fischer projections of 1,6-GPS (left) and 1,1-GPM (right)
Names
IUPAC name
(2ξ)-6-O-α-D-Glucopyranosyl-D-arabino-hexitol
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.122.870
E number E953 (glazing agents, ...)
PubChem CID
UNII
  • 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 Y
    Key: SERLAGPUMNYUCK-BLEZHGCXSA-N Y
  • Isomalt: InChI=1/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
    Key: SERLAGPUMNYUCK-DCUALPFSBK
  • 1,6-GPS: Key: SERLAGPUMNYUCK-YJOKQAJESA-N
  • 1,1-GPM: Key: SERLAGPUMNYUCK-DCUALPFSSA-N
  • Key: SERLAGPUMNYUCK-UHFFFAOYSA-N
SMILES
  • Isomalt: O(C[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)CO)[C@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO.OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O
Properties
C12H24O11
Molar mass 344.313 g·mol−1
Hazards
NFPA 704 (fire diamond)
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Like most sugar alcohols (including the chemically similar maltitol), isomalt carries a risk of intestinal distress when consumed in large quantities (above about 20–30 g (1 oz) 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 dietary fibers, regular consumption of isomalt can lead to desensitization, decreasing the risk of intestinal upset.

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.

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