Isomalt

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Isomalt
IsomaltV1.svg
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 OOjs UI icon edit-ltr-progressive.svg
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 Yes check.svgY
    Key: SERLAGPUMNYUCK-BLEZHGCXSA-N Yes check.svgY
  • 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
  • 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)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
1
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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. [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 sucrose (‘sugar’).

Contents

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). [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: 1-O-α-D-glucopyranosido-D-mannitol (1,1-GPM) and 6-O-α-D-glucopyranosido-D-sorbitol (1,6-GPS). Each of these is composed of two sugars: glucose and mannitol in the case of 1,1-GPM and glucose and sorbitol (also known as glucitol) in the case of 1,6-GPS. Complete hydrolysis of isomalt yields glucose (50%), sorbitol (25%), and mannitol (25%). [1]

Isomalt 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 (typically derived from beet sugar) is first transformed into isomaltulose using the bacterial enzyme isomaltulose synthase. The isomaltulose is then hydrogenated using a Raney nickel catalyst, producing 1,1-GPM and 1,6-GPS. The product consists of a mixture of anhydrous and dihydrated 1,1-GPM and anhydrous 1,6-GPS. [5]

About 100,000 tons were produced in 2012. [5]

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. [6]

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. [7]

In 2023 it was reported that isomalt, when mixed with cellulose or sawdust, can be used as a moldable, recyclable and biodegradable material that's stronger than PVC and PET. It dissolves upon contact with water but can be protected from water with a layer of shellac and cellulose acetate. [8]

Related Research Articles

<span class="mw-page-title-main">Carbohydrate</span> Organic compound that consists only of carbon, hydrogen, and oxygen

A carbohydrate is a biomolecule consisting of carbon (C), hydrogen (H) and oxygen (O) atoms, usually with a hydrogen–oxygen atom ratio of 2:1 and thus with the empirical formula Cm(H2O)n, which does not mean the H has covalent bonds with O. However, not all carbohydrates conform to this precise stoichiometric definition, nor are all chemicals that do conform to this definition automatically classified as carbohydrates.

<span class="mw-page-title-main">Disaccharide</span> Complex sugar

A disaccharide is the sugar formed when two monosaccharides are joined by glycosidic linkage. Like monosaccharides, disaccharides are simple sugars soluble in water. Three common examples are sucrose, lactose, and maltose.

<span class="mw-page-title-main">Glucose</span> Naturally produced monosaccharide

Glucose is a sugar with the molecular formula C6H12O6. Glucose is overall the most abundant monosaccharide, a subcategory of carbohydrates. Glucose is mainly made by plants and most algae during photosynthesis from water and carbon dioxide, using energy from sunlight, where it is used to make cellulose in cell walls, the most abundant carbohydrate in the world.

<span class="mw-page-title-main">Sucralose</span> Chemical compound

Sucralose is an artificial sweetener and sugar substitute. The majority of ingested sucralose is not broken down by the body, so it is noncaloric. In the European Union, it is also known under the E number E955. It is produced by chlorination of sucrose, selectively replacing three of the hydroxy groups—in the C1 and C6 positions of fructose and the C4 position of glucose—to give a 1,6-dichloro-1,6-dideoxyfructose–4-chloro-4-deoxygalactose disaccharide. Sucralose is about 320 to 1,000 times sweeter than sucrose, three times as sweet as both aspartame and acesulfame potassium, and twice as sweet as sodium saccharin.

<span class="mw-page-title-main">Fructose</span> Simple ketonic monosaccharide found in many plants

Fructose, or fruit sugar, is a ketonic simple sugar found in many plants, where it is often bonded to glucose to form the disaccharide sucrose. It is one of the three dietary monosaccharides, along with glucose and galactose, that are absorbed by the gut directly into the blood of the portal vein during digestion. The liver then converts both fructose and galactose into glucose, so that dissolved glucose, known as blood sugar, is the only monosaccharide present in circulating blood.

<span class="mw-page-title-main">Sorbitol</span> Chemical compound

Sorbitol, less commonly known as glucitol, is a sugar alcohol with a sweet taste which the human body metabolizes slowly. It can be obtained by reduction of glucose, which changes the converted aldehyde group (−CHO) to a primary alcohol group (−CH2OH). Most sorbitol is made from potato starch, but it is also found in nature, for example in apples, pears, peaches, and prunes. It is converted to fructose by sorbitol-6-phosphate 2-dehydrogenase. Sorbitol is an isomer of mannitol, another sugar alcohol; the two differ only in the orientation of the hydroxyl group on carbon 2. While similar, the two sugar alcohols have very different sources in nature, melting points, and uses.

<span class="mw-page-title-main">Sugar substitute</span> Sugarless food additive intended to provide a sweet taste

A sugar substitute is a food additive that provides a sweetness like that of sugar while containing significantly less food energy than sugar-based sweeteners, making it a zero-calorie or low-calorie sweetener. Artificial sweeteners may be derived through manufacturing of plant extracts or processed by chemical synthesis. Sugar substitute products are commercially available in various forms, such as small pills, powders, and packets.

<span class="mw-page-title-main">Xylitol</span> Synthetic sweetener

Xylitol is a chemical compound with the formula C
5
H
12
O
5
, or HO(CH2)(CHOH)3(CH2)OH; specifically, one particular stereoisomer with that structural formula. It is a colorless or white crystalline solid that is freely soluble in water. It can be classified as a polyalcohol and a sugar alcohol, specifically an alditol. The name derives from Ancient Greek: ξύλον, xyl[on] 'wood', with the suffix -itol used to denote sugar alcohols.

<span class="mw-page-title-main">Inverted sugar syrup</span> Edible mixture of glucose and fructose, obtained from sucrose hydrolysis

Inverted sugar syrup, also called invert syrup, invert sugar, simple syrup, sugar syrup, sugar water, bar syrup, syrup USP, or sucrose inversion, is a syrup mixture of the monosaccharides glucose and fructose, that is made by hydrolytic saccharification of the disaccharide sucrose. This mixture's optical rotation is opposite to that of the original sugar, which is why it is called an invert sugar.

<span class="mw-page-title-main">Sugar alcohol</span> Organic compounds

Sugar alcohols are organic compounds, typically derived from sugars, containing one hydroxyl group (−OH) attached to each carbon atom. They are white, water-soluble solids that can occur naturally or be produced industrially by hydrogenating sugars. Since they contain multiple −OH groups, they are classified as polyols.

<span class="mw-page-title-main">Trehalose</span> Chemical compound

Trehalose is a sugar consisting of two molecules of glucose. It is also known as mycose or tremalose. Some bacteria, fungi, plants and invertebrate animals synthesize it as a source of energy, and to survive freezing and lack of water.

<span class="mw-page-title-main">Mannitol</span> Chemical compound

Mannitol is a type of sugar alcohol used as a sweetener and medication. It is used as a low calorie sweetener as it is poorly absorbed by the intestines. As a medication, it is used to decrease pressure in the eyes, as in glaucoma, and to lower increased intracranial pressure. Medically, it is given by injection or inhalation. Effects typically begin within 15 minutes and last up to 8 hours.

<span class="mw-page-title-main">Lactitol</span> Chemical compound

Lactitol is a disaccharide sugar alcohol produced from lactose. It is used as a replacement bulk sweetener for low calorie foods with 30–40% of the sweetness of sucrose. It is also used medically as a laxative.

<span class="mw-page-title-main">Maltitol</span> Chemical compound

Maltitol is a sugar alcohol used as a sugar substitute and laxative. It has 75–90% of the sweetness of sucrose and nearly identical properties, except for browning. It is used to replace table sugar because it is half as energetic, does not promote tooth decay, and has a somewhat lesser effect on blood glucose. In chemical terms, maltitol is known as 4-O-α-glucopyranosyl-D-sorbitol. It is used in commercial products under trade names such as Lesys, Maltisweet and SweetPearl.

<span class="mw-page-title-main">Psicose</span> Chemical compound

D-Psicose (C6H12O6), also known as D-allulose, or simply allulose, is a low-calorie epimer of the monosaccharide sugar fructose, used by some major commercial food and beverage manufacturers as a low-calorie sweetener. First identified in wheat in the 1940s, allulose is naturally present in small quantities in certain foods.

<span class="mw-page-title-main">Isomaltulose</span> Chemical compound

Isomaltulose is a disaccharide carbohydrate composed of glucose and fructose. It is naturally present in honey and sugarcane extracts and is also produced industrially from table sugar (sucrose) and used as a sugar alternative.

<span class="mw-page-title-main">Glucose-galactose malabsorption</span> Medical condition

Glucose-galactose malabsorption is a rare condition in which the cells lining the intestine cannot take in the sugars glucose and galactose, which prevents proper digestion of these molecules and larger molecules made from them.

Isomaltooligosaccharide (IMO) is a mixture of short-chain carbohydrates which has a digestion-resistant property. IMO is found naturally in some foods, as well as being manufactured commercially. The raw material used for manufacturing IMO is starch, which is enzymatically converted into a mixture of isomaltooligosaccharides.

<span class="mw-page-title-main">Trehalulose</span> Chemical compound

Trehalulose is a disaccharide made up of a molecule of fructose bound to a molecule of glucose. Like isomaltulose, it is a structural isomer of sucrose that is present in small quantities in honey. It makes up 50% of sugars in the honeydew of silverleaf whiteflies and is synthesised from sucrose by some bacteria, such as Protaminombacter rubrum. Because the anomeric carbon of the fructose moiety is not involved in the glycosidic bond, it is a reducing sugar.

References

  1. 1 2 3 4 5 "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   978-1-4613-1229-1.
  4. Wohlfarth, Christian. CRC Handbook of Enthalpy Data of Polymer-Solvent Systems. CRC Press, 2006. Google Books result: ISBN   0-8493-9361-2
  5. 1 2 Schiweck, Hubert; Bär, Albert; Vogel, Roland; Schwarz, Eugen; Kunz, Markwart; Dusautois, Cécile; Clement, Alexandre; Lefranc, Caterine; Lüssem, Bernd; Moser, Matthias; Peters, Siegfried (2012). "Sugar Alcohols: 5.2 Isomalt". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a25_413.pub3. ISBN   9783527303854.
  6. The Oxford Companion to Sugar and Sweets. Oxford University Press. 2015-04-01. ISBN   978-0-19-931362-4.
  7. 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.
  8. "Plant-and-wood-based material is strong, yet dissolves when discarded". New Atlas. 2023-04-12. Retrieved 2023-04-24.

Further reading