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E 953 is a sugar substitute, a type of sugar alcohol used primarily for its sugar-like physical properties.
E 953 has little to no impact on blood sugar levels, and does not stimulate the release of insulin.
E 953 also does not promote tooth decay and is considered to be tooth-friendly.
CAS: 64519-82-0
MF: C12H24O11
MW: 344.31
EINECS: 908-700-6
E 953's energy value is 2 kcal per gram, half that of sugars.
E 953 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’).
Like most sugar alcohols (including the chemically similar maltitol), E 953 carries a risk of intestinal distress when consumed in large quantities (above about 20–30 g (1 oz) per day).
E 953 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 E 953 can lead to desensitization, decreasing the risk of intestinal upset.
E 953 has been approved for use in the United States since 1990.
E 953 is also permitted for use in Australia, New Zealand, Canada, Mexico, Iran, the European Union, and other countries.
E 953 is claimed that isomalt is odorless, white, crystalline, and sweet tasting without the accompanying taste or aftertaste.
Sweetening power is from 0.45 to 0.6 that of sucrose.
A synergistic effect is achieved when E 953 is combined with other artificial sweeteners and sugar substitutes.
Principal applications are in confections, pan-coated goods, and chewing gum.
E 953 was approved for use in most European countries in 1985.
Classification of E 953 as a GRAS substance was petitioned in the United States.
E 953 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 E 953 yields glucose (50%), sorbitol (25%), and mannitol (25%).
E 953 is an odorless, white, crystalline substance containing about 5% water of crystallisation.
E 953 has a minimal cooling effect (positive heat of solution), lower than many other sugar alcohols, in particular, xylitol and erythritol.
E 953 is a sugar-free sweetener that is used as an alternative to sugar due to its physical properties.
Sugar alcohols such as E 953 are absorbed sparingly into the small intestines hence it has an insignificant effect on blood sugar concentration.
E 953 provides a wide range of other benefits such as low hygroscopicity, a natural taste, minimal calories per gram and it is tooth-friendly.
This sweetener can be used by anyone and E 953 can also be beneficial as it promotes gut health in people who are on low-carb diets and diabetic patients.
In the European Union, E 953 is indicated on food labels as E/E953.
E 953 is an equimolar mixture of oc-D-glucopyranosyl-1,6- D-sorbitol (GPS) and α-D-glucopyranosyl-l,l-D-mannitol (GPM).
The production process of E 953 involves two essential steps.
In the first step, the 1,2 -glycosidic linkage between the glucose and the fructose moiety of sucrose is rearranged by an immobilized enzyme system to a 1,6 -glycosidic linkage, which is more stable and characteristic for the cross linkage in the amylopectin fraction of native starch.
In the second step, the rearranged sucrose molecule, i.e., E 953, is hydrogenated to the corresponding sugar alcohols.
E 953 is commercially available as a dry, white crystalline powder which is about half as sweet as sucrose.
In vitro studies with intestinal disaccharidases from mammals demonstrated that E 953 is cleaved much more slowly than sucrose or maltose.
A slight inhibitory effect on maltose hydrolysis and on the active transport on glucose has also been observed.
Ingested E 953 is partly hydrolyzed in the small intestine and slowly absorbed in the form of glucose, sorbitol, and mannitol.
The intact portion of E 953, as well as some unabsorbed sorbitol and mannitol, reaches the distal parts of the gut where these products are fermented to volatile fatty acids.
E 953 is a non-cariogenic excipient used in a variety of pharmaceutical preparations, including tablets or capsules, coatings, sachets, suspensions and effervescent tablets.
E 953 can be used for direct compression and wet granulation.
E 953 is also widely used in lozenges, sugar-free chewing gums and cooked candies, and as a sweetening agent in confectionery for diabetics.
E 953 Chemical Properties
Boiling point: 788.5±60.0 °C(Predicted)
Density: 1.69±0.1 g/cm3(Predicted)
Vapor pressure: 0-0Pa at 20-50℃
Storage temp.: Sealed in dry,Room Temperature
Solubility: Freely soluble in water, practically insoluble in anhydrous ethanol.
Form: neat
pka: 12.89±0.70(Predicted)
Water Solubility: Water: 250 mg/mL (726.09 mM)
InChIKey: RWJWQKXVEITNKS-JSOWRAQNSA-N
LogP: -4.2--3.7 at 20℃
CAS DataBase Reference: 64519-82-0(CAS DataBase Reference)
E 953 is a combination of 2 sugar alcohols: gluco-sorbitol (GPS) and gluco-mannitol (GPM).
E 953 is a white crystalline compound without an odour.
E 953 is 55% as sugary as sucrose and it can dissolve readily into the mouth, leaving a cooling effect.
The compound has low hygroscopicity at a relative humidity (85%).
E 953 dissolves in water at 250 C/770 F, 25 g/100g of the solution; E 953 is sparingly soluble in ethanol.
The compound has a melting point of 145-1500 C/293-3020 F and E 953 decomposes at 1600 C/3200 F or higher temperatures.
One manufacturer maintains that E 953 does not caramelize or go through the Maillard browning interaction with amino acids.
Isomalt functions in the same way as other sparingly digestible compounds hence its fermentation in the intestines may result in flatulence, diarrhoea, abdominal pain, and bloating if the compound is ingested in bulk.
However, the consistent use of Isomalt makes one tolerant of sugar alcohols, which minimizes the probability of occurrence of associated side effects.
E 953 is a more or less equimolar mixture of 1-O-a-D-glucopyranosy-D-mannitol- dihydrate and 6-O-a-D-glucopyranosyl-D-sorbitol.
Different production conditions, however, allow variations in the ratio of the two products.
The solubility in water is about 24.5 % (w/w) at room temperature, but varies with the composition and increases with increasing temperature.
In addition to the dry E 953, a syrup is available.
E 953 is, depending on the concentration, approximately 45–60 % as sweet as sucrose, stable under normal processing conditions of foods, and noncariogenic.
In the European Union, E 953 is approved as E 953 for a large number of food applications.
E 953 is GRAS in the United States and also approved in many other countries.
Owing to its low glycemic index, E 953, an intermediate of the production, has found increasing interest as a food ingredient in recent years.
E 953 is a sugar alcohol (polyol) that occurs as a white or almost white powder or granular or crystalline substance.
E 953 has a pleasant sugarlike taste with a mild sweetness approximately 50–60% of that of sucrose.
Uses
E 953 is widely used for the production of sugar-free candy, especially hard-boiled candy, because E 953 resists crystallization much better than the standard combinations of sucrose and corn syrup.
E 953 is used in sugar sculpture for the same reason.
E 953 is incorporated into sugar-free products due to its tolerable aftertaste and sweet purity.
The compound can be applied to a wide range of foods such as low-fat ice-cream, milk & chilled drinks, table sugar, daubing food, baking food, corn breakfast food, chewing gum, chocolate and candy.
E 953 is also used as an anti-caking, glazing and bulking agent in low-calorie toffees, fruit spreads, smoked and frozen meat and fish, infant formulas, lozenges, pan-coated tablets, mineral/multivitamin supplements and jams.
E 953 increases the transfer of flavour in certain foods.
E 953's gradual dissolution after consumption makes candy made from this compound last for a longer time.
E 953 does not leave behind the unpleasant cooling effect associated with other polyols.
These sensory properties make E 953 ideal for addition into flavoured applications and baked products.
E 953 can also be used as a plasticizer for high methoxyl pectin films.
E 953 reduces the rigidity of the edible film by increasing free volume within the structure of the film.
Additionally E 953 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.
Pharmaceutical Applications
E 953 is a noncariogenic excipient used in a variety of pharmaceutical preparations including tablets or capsules, coatings, sachets, and suspensions, and in effervescent tablets.
E 953 can also be used in direct compression and wet granulation.
In buccal applications such as chewable tablets E 953 is commonly used because of its negligible negative heat of solution, mild sweetness, and ‘mouth feel’.
E 953 is also used widely in lozenges, sugar-free chewing gum, and hard-boiled candies, and as a sweetening agent in confectionery for diabetics.
Manufacture
E 953 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).
E 953 is then hydrogenated, using a Raney nickel catalyst.
The final product — E 953 — 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).
The preparation process starts with sucrose.
An enzyme inhibits the link between fructose and glucose in sucrose.
In the fructose segment of the disaccharide, 2 hydrogen molecules are added to the oxygen molecule present.
About half of the original fructose segment from the disaccharide is transformed into mannitol and approximately half of the fructose segment of the initial disaccharide is transformed into sorbitol.
Therefore, E 953 comprises 2 disaccharide alcohols: gluco-sorbitol and gluco-mannitol.
The molecular modifications that take this format make Isomalt enzymatically and chemically stable than sucrose.
The stability of the compound makes E 953 ideal for incorporation into a wide range of products and consumption based on its health-related advantages.
Biotechnological Production
For the production of E 953 sucrose is converted to isomaltulose which is then hydrogenated to yield a mixture of the two components of isomalt.
Although the production of E 953 itself from isomaltulose is a chemical hydrogenation, transformation of sucrose into isomaltulose requires enzymatic transformation.
The enzyme sucrosemutase is sensitive to glutaraldehyde, therefore crosslinking is not possible.
For industrial use E 953 is, however, not necessary to isolate the enzyme, as immobilized cells of the organism can be used.
Addition of sodium alginate to the cultivated cells and subsequent addition of calcium acetate immobilizes the cells.
This allows for the use of the cells in a bed reactor, and also facilitates the separation of the product from the reaction mixture.
The long-term stability of the immobilized organism is high and can exceed 5,000 h, even if high sucrose concentrations of 550 g/L are used.
The yields are about 80–85 % with 9–11 % of trehalulose and small quantities of other saccharides as by-products.
Prior to hydrogenation, free sucrose has to be removed.
This is carried out by nonviable cells of Saccharomyces cerevisiae.
Remaining by-products of the reaction are converted to the respective sugar alcohols.
Although the hydrogenation of isomaltulose theoretically should yield an equimolar mixture of the two constituents of isomalt, the share of each component may vary between 43–57 % depending on the conditions of hydrogenation.
An alternative possibility is the direct cultivation of suitable microorganisms such as P. rubrum on sucrose-containing juices obtained during the production of beet and cane sugar.
E 953 is claimed that glucose and fructose produced during the transformation are consumed by the microorganisms which results in lower amounts of by-products.
Synonyms
Isomalt
64519-82-0
Palatinitol
(3R,4R,5R)-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexane-1,2,3,4,5-pentol
6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexane-1,2,3,4,5-pentol
(3R,4R,5R)-6-(((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)hexane-1,2,3,4,5-pentaol
C-isomaltidex
INS NO.953
SCHEMBL1781066
CHEMBL2104398
DTXSID8020753
INS-953
CHEBI:140428
CHEBI:192266
BAY I 3930
BAY-I-3930
MFCD00083636
s4441
D-Glucitol, 6-O-a-D-glucopyranosyl-, mixt. with1-O-a-D-glucopyranosyl-D-mannitolOTHER CA INDEX NAMES:D-Mannitol, 1-O-a-D-glucopyranosyl-, mixt. contg.
DS-13958
E-953
EN300-22246339
(2xi)-6-O-alpha-D-glucopyranosyl-D-arabino-hexitol
Z2737384431
A4017F7C-EDDD-4444-9BE5-110558E41162
D-arabino-Hexitol, 6-O-.alpha.-D-glucopyranosyl-, (2.epsilon.)-
(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
