Isomaltulose

For a disaccharide polyol derived from sucrose, see isomalt. For a disaccharide derived from maltose, see isomaltose.
Isomaltulose
Names
IUPAC name
6-O-α-D-Glucopyranosyl-D-fructose
Other names
Palatinose
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.033.878 Edit this at Wikidata
EC Number
  • 237-282-1
UNII
  • InChI=1S/C12H22O11/c13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h5-14,16-21H,1-3H2/t5-,6-,7-,8-,9-,10+,11-,12+/m1/s1 checkY
    Key: RJPPRBMGVWEZRR-WTZPKTTFSA-N checkY
  • InChI=1/C12H22O11/c13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h5-14,16-21H,1-3H2/t5-,6-,7-,8-,9-,10+,11-,12+/m1/s1
    Key: RJPPRBMGVWEZRR-WTZPKTTFBY
  • O=C(CO)[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
Properties
C12H22O11
Molar mass 342.297 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Isomaltulose (trade name Palatinose, chemical name 6-O-α-D-glucopyranosyl-D-fructose) is a disaccharide carbohydrate composed of glucose and fructose. It is naturally present in honey[1] and sugarcane extracts[2] and is also produced industrially from table sugar (sucrose) and used as a sugar alternative.

It tastes similar to table sugar with half the sweetness. It has the same energy as table sugar, but is digested slower and thus leads to a lower blood glucose and insulin response. In comparison with sucrose and most other carbohydrates, isomaltulose is not a significant substrate for oral bacteria. Consequently, acid production from isomaltulose in the mouth is too slow to promote tooth decay.[3] Its physical properties closely resemble those of sucrose, making it easy to use in existing recipes and processes.

It is manufactured by enzymatic rearrangement (isomerization) of sucrose from beet sugar. Since the 1950s its physiological role and physical properties have been studied extensively.[3][4][5] Isomaltulose has been used as an alternative to sugar in foods in Japan since 1985, in the EU since 2005, in the US since 2006, and in Australia and New Zealand since 2007,[6] besides other countries worldwide.

Like sucrose, isomaltulose can be digested to glucose and fructose. However, while in sucrose the glucose is linked to the anomeric carbon of the fructose (an α-1,2 glycosidic linkage), in isomaltulose the linkage is to the 6 carbon (α-1,6), making isomaltulose a reducing sugar, unlike sucrose. The fructose in isomaltulose exists in a ring structure that readily opens to exhibit a carbonyl group as in ketones and aldehydes, which explains why isomaltulose is a reducing sugar.[7]

Isomaltulose is hydrogenated to produce isomalt, a minimally digestible carbohydrate that is used as a sugar replacer, for example in sugar-free candies and confectionery.

  1. ^ Siddiqua, I.R; Furgala, B (1967). "Isolation and characterization of oligosaccharides from honey". Journal of Apicultural Research. 6 (3): 139–145. doi:10.1080/00218839.1967.11100174.
  2. ^ Egglestone, G; Grisham, M (2003). "Oligosaccharides in cane and their formation on cane deterioration". ACS Symposium Series. 849 (16): 211–232. doi:10.1021/bk-2003-0849.ch016.
  3. ^ a b Sentko, A. and Willibald-Ettle, I. (2012). "Isomaltulose." In: Sweeteners and Sugar Alternatives in Food Technology, 2nd Ed. Editors O'Donnell, K. & Kearsley, M.W. Wiley-Blackwell. Oxford, UK. ISBN 978-0-470-65968-7
  4. ^ Lina, B.A.R.; Jonker, D.; Kozianowski, G. (2002). "Isomaltulose (Palatinose): A review of biological and toxicological studies". Food and Chemical Toxicology. 40 (10): 1375–81. doi:10.1016/S0278-6915(02)00105-9. PMID 12387299.
  5. ^ Maresch, C.C; Petry, S.F; Theis, S; Bosy-Westphal, A; Linn, T (2017). "Low Glycemic Index Prototype Isomaltulose-Update of Clinical Trials". Nutrients. 9 (4): 1–12. doi:10.3390/nu9040381. PMC 5409720. PMID 28406437.
  6. ^ "Australia New Zealand Food Standards Code – Amendment No. 92 – 2007" (PDF). Commonwealth of Australia Gazette (FSC 34 Thursday, 2 August 2007). 2007. Retrieved 9 February 2018.
  7. ^ O'Donnell, Kay; Kearsley, Malcolm (2012-07-13). Sweeteners and Sugar Alternatives in Food Technology. John Wiley & Sons. ISBN 9781118373972.