Isomalt

Isomalt
Names
	IUPAC name (2R,3R,4R,5R)-6-[[(2S,3R,4S,5S,6R)- 3,4,5-Trihydroxy-6-(hydroxymethyl)-2-tetrahydropyranyl]oxy]hexane-1,2,3,4,5-pentol
	Other names 1-O-α-D-Glucopyranosyl-D-mannitol
Identifiers
CAS Number	64519-82-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:150326;
ChEMBL	ChEMBL2104398 ;
ChemSpider	80068 ;
PubChem CID	88735;
UNII	S870P55O2W ;
	InChI 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 Key: SERLAGPUMNYUCK-DCUALPFSSA-N ; 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;
	SMILES 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;
Properties
Chemical formula	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). verify (what is ?) Infobox references

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.^[1] 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.^[2] 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 sugar.

Like most sugar alcohols, isomalt carries a risk of intestinal distress when consumed in large quantities (above about 20–30 g (1 oz) per day).^[1] 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^[3] and stimulate the gut flora, causing flatulence.^[1] As with dietary fibers, regular consumption of isomalt can lead to desensitization, decreasing the risk of intestinal upset.^[1]

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.

Composition and structure

Isomalt is an equimolar mixture of two 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%).^[1] It is an odorless, white, crystalline substance containing about 5% water of crystallisation. Isomalt has a minimal cooling effect (positive heat of solution^[4]), lower than many other sugar alcohols, in particular, xylitol and erythritol.

Manufacture

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).

Uses

Isomalt is widely used for the production of sugar-free candy, especially hard-boiled candy, because it resists crystallization much better than the standard combinations of sucrose and corn syrup. It is used in sugar sculpture for the same reason.^[5]

Isomalt can also be used as a plasticizer for high methoxyl pectin films. It reduces the rigidity of the edible film by increasing free volume within the structure of the film. Additionally isomalt also reduces the water vapour permeability of the film, thus increasing the quality of the film as it reduces respiration rate, moisture migration, and loss of volatile compounds.^[6]

References

^ ^a ^b ^c ^d ^e "604. Isomalt (WHO Food Additives Series 20)". INCHEM. Retrieved 2017-09-28.
^ Duffy, V. B.; Anderson, G. H. (1998). "Position of The American Dietetic Association (use of nutritive and nonnutritive sweeteners)". J. Am. Diet. Assoc. 98 (5): 580–7. doi:10.1016/S0002-8223(98)00131-X. PMID 9597035.
^ Grenby, Trevor H. (2012-12-06). Advances in Sweeteners. Springer Science & Business Media. ISBN 9781461312291.
^ Wohlfarth, Christian. CRC Handbook of Enthalpy Data of Polymer-Solvent Systems. CRC Press, 2006. Google Books result: ISBN 0-8493-9361-2
^ The Oxford Companion to Sugar and Sweets. Oxford University Press. 2015-04-01. ISBN 9780199313624.
^ Matta, Eliana; Bertola, Nora (11 August 2020). "Development and characterization of high methoxyl pectin film by using isomalt as plasticizer". Journal of Food Processing and Preservation. 44 (8). doi:10.1111/jfpp.14568. S2CID 219508688.

External links

Media related to Isomalt at Wikimedia Commons

[:0-1] "604. Isomalt (WHO Food Additives Series 20)". INCHEM. Retrieved 2017-09-28.

[2] Duffy, V. B.; Anderson, G. H. (1998). "Position of The American Dietetic Association (use of nutritive and nonnutritive sweeteners)". J. Am. Diet. Assoc. 98 (5): 580–7. doi:10.1016/S0002-8223(98)00131-X. PMID 9597035.

[3] Grenby, Trevor H. (2012-12-06). Advances in Sweeteners. Springer Science & Business Media. ISBN 9781461312291.

[4] Wohlfarth, Christian. CRC Handbook of Enthalpy Data of Polymer-Solvent Systems. CRC Press, 2006. Google Books result: ISBN 0-8493-9361-2

[5] The Oxford Companion to Sugar and Sweets. Oxford University Press. 2015-04-01. ISBN 9780199313624.

[6] Matta, Eliana; Bertola, Nora (11 August 2020). "Development and characterization of high methoxyl pectin film by using isomalt as plasticizer". Journal of Food Processing and Preservation. 44 (8). doi:10.1111/jfpp.14568. S2CID 219508688.

[1]

[2]

[3]

[4]

[5]

[6]