Isomalt CAS 64519-82-0
Introduction：Basic information about Isomalt CAS 64519-82-0, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Isomalt Basic informationDescription Properties Preparation Uses Absorption Side Effects Precautions
| Product Name: | Isomalt |
| Synonyms: | Mixture Of 1-(4-Fluorophenyl-3S-[3-(4-Fluorophenyl-3S-Hydroxypropyl]-4S-(4-Hydroxyphenyl-AzetidiN-2-One And 1-(4-Fluorophenyl-3R-[3-(4-Fluorophenyl-3R-Hydroxypropyl]-4R-(4-Hydroxyphenyl-Azetidin;alpha-D-glucopyranosyl-1,6-D-sorbitolpolymerwithD-Mannitol;mixedwith1-o-alpha-d-glucopyranosyl-d-glucito;α-D-Glucopyranosyl-1,6-D-sorbitol;Isomaleone glycol;yimaiyatonyangsun;D-arabino-Hexitol,;ISOMALTITOL; PALATINITOL |
| CAS: | 64519-82-0 |
| MF: | C12H24O11 |
| MW: | 344.31 |
| EINECS: | 908-700-6 |
| Product Categories: | Halogenated Heterocycles ,Thiophenes ,Thiazolines/Thiazolidines;Food additive and Sweetener;Dextrins、Sugar & Carbohydrates;Food & Flavor Additives |
| Mol File: | 64519-82-0.mol |
Isomalt 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. |
| pka | 12.89±0.70(Predicted) |
| form | Solid |
| color | White to off-white |
| Odor | at 100.00?%. odorless |
| Water Solubility | Water: 250 mg/mL (726.09 mM) |
| Stability: | Hygroscopic |
| Major Application | pharmaceutical (small molecule) |
| Cosmetics Ingredients Functions | HUMECTANT |
| Cosmetic Ingredient Review (CIR) | Isomalt (64519-82-0) |
| 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 |
| InChIKey | RWJWQKXVEITNKS-JSOWRAQNSA-N |
| SMILES | O1[C@@H]([C@@H]([C@H]([C@@H]([C@H]1CO)O)O)O)OC[C@@H](O)[C@@H](O)[C@H](O)C(O)CO |
| LogP | -4.2--3.7 at 20℃ |
| CAS DataBase Reference | 64519-82-0(CAS DataBase Reference) |
Safety Information
| Hazard Codes | Xn |
| Risk Statements | 20/21/22-37/38-41-48 |
| Safety Statements | 22-26-36/37/39-45 |
| WGK Germany | 3 |
| RTECS | LZ4394500 |
| HS Code | 2940006000 |
| Storage Class | 11 - Combustible Solids |
| Hazardous Substances Data | 64519-82-0(Hazardous Substances Data) |
| Description | Isomalt is a sugar-free sweetener that is used as an alternative to sugar due to its physical properties. Sugar alcohols such as Isomalt are absorbed sparingly into the small intestines hence it has an insignificant effect on blood sugar concentration. Isomalt 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 it can also be beneficial as it promotes gut health in people who are on low-carb diets and diabetic patients. In the European Union, Isomalt is indicated on food labels as E/E953. |
| Properties | Isomalt is a combination of 2 sugar alcohols: gluco-sorbitol (GPS) and gluco-mannitol (GPM). It is a white crystalline compound without an odour. Isomalt 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%). Isomalt dissolves in water at 250 C/770 F, 25 g/100g of the solution; it is sparingly soluble in ethanol. The compound has a melting point of 145-1500 C/293-3020 F and it decomposes at 1600 C/3200 F or higher temperatures. One manufacturer maintains that Isomalt does not caramelize or go through the Maillard browning interaction with amino acids. |
| Preparation | 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, Isomalt 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 it ideal for incorporation into a wide range of products and consumption based on its health-related advantages. |
| Uses | Isomalt 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. It 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. Isomalt increases the transfer of flavour in certain foods. Its gradual dissolution after consumption makes candy made from this compound last for a longer time. Isomalt does not leave behind the unpleasant cooling effect associated with other polyols. These sensory properties make it ideal for addition into flavoured applications and baked products. |
| Absorption | About 10% of the ingested compound is digested to mannitol, sorbitol and glucose in the small intestines whereas the rest is conveyed into the large intestine where it undergoes fermentation in the presence of beneficial bacteria to release short-chain fatty acids (SCFAs) and gases. The SCFAs are sparingly absorbed into the large intestine and some are consumed by the bacteria. |
| Side Effects | 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. |
| Precautions | Isomalt is not recommended for use in pregnant women, children and newborns. However, if the intake of this compound is inevitable, one should consult a doctor. |
| Description | Isomalt 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 isomalt 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., isomaltulose, is hydrogenated to the corresponding sugar alcohols. Isomalt 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 isomalt 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 isomalt is partly hydrolyzed in the small intestine and slowly absorbed in the form of glucose, sorbitol, and mannitol. The intact portion of isomalt, as well as some unabsorbed sorbitol and mannitol, reaches the distal parts of the gut where these products are fermented to volatile fatty acids. |
| Chemical Properties | White or almost white powder or granules. |
| Chemical Properties | Isomalt 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 productionconditions, however, allow variations in the ratio of the two products. The solubilityin water is about 24.5 % (w/w) at room temperature, but varies with thecomposition and increases with increasing temperature. In addition to the dryisomalt, a syrup is available. Isomalt is, depending on the concentration, approximately 45–60 % assweet as sucrose, stable under normal processing conditions of foods, andnoncariogenic. In the European Union, isomalt is approved as E 953 for a large number of foodapplications. It is GRAS in the United States and also approved in many othercountries. Owing to its low glycemic index, isomaltulose, an intermediate of the production,has found increasing interest as a food ingredient in recent years. |
| Chemical Properties | Isomalt is a sugar alcohol (polyol) that occurs as a white or almostwhite powder or granular or crystalline substance. It has a pleasantsugarlike taste with a mild sweetness approximately 50–60% ofthat of sucrose. |
| History | It 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 isomalt is combined with other artificial sweeteners and sugar substitutes. Principal applications are in confections, pan-coated goods, and chewing gum. The substance was approved for use in most European countries in 1985. Classification of isomalt as a GRAS substance was petitioned in the United States. (GRAS = generally regarded as safe.) |
| Uses | analgesic, NSAID |
| Production Methods | Isomalt is produced from food-grade sucrose in a two-stage process.Beet sugar is converted by enzymatic transglucosidation into thereducing disaccharide isomaltulose. This undergoes catalyticalhydrogenation to produce isomalt. |
| Production Methods | Developed in Germany, isomalt is described as an energy-reduced bulk sweetener and marketed in Europe under the tradename Palatinit? mark. The compound is produced from sucrose in a two-step process. In the first step, the easily hydrolyzable 1-2 glucoside linkage between the glucose and fructose moieties of sucrose are catalyzed by immobilized enzymes to produce isomaltulose, Palatinos mark After crystallization, the isomaltulose is hydrogenated in a neutral aqueous solution using a nickel catalyst. |
| Definition | ChEBI: (2xi)-6-O-alpha-D-glucopyranosyl-D-arabino-hexitol is a glycosyl alditol consisting of alpha-D-glucopyranose and (2xi)-D-arabino-hexitol residues joined in sequence by a (1->1) glycosidic bond. It is functionally related to an alpha-D-glucose. |
| Biotechnological Production | For the production of isomalt sucrose is converted to isomaltulose which is thenhydrogenated to yield a mixture of the two components of isomalt. Althoughthe production of isomalt itself from isomaltulose is a chemical hydrogenation,transformation of sucrose into isomaltulose requires enzymatic transformation.The enzyme sucrosemutase is sensitive to glutaraldehyde, therefore crosslinkingis not possible. For industrial use it is, however, not necessary to isolate theenzyme, as immobilized cells of the organism can be used. Addition of sodiumalginate to the cultivated cells and subsequent addition of calcium acetateimmobilizes the cells. This allows for the use of the cells in a bed reactor, and alsofacilitates the separation of the product from the reaction mixture.The long-term stability of the immobilized organism is high and can exceed5,000 h, even if high sucrose concentrations of 550 g/L are used. The yields areabout 80–85 % with 9–11 % of trehalulose and small quantities of other saccharidesas by-products. Prior to hydrogenation, free sucrose has to be removed. This is carried out bynonviable cells of Saccharomyces cerevisiae. Remaining by-products of thereaction are converted to the respective sugar alcohols.Although the hydrogenation of isomaltulose theoretically should yield anequimolar mixture of the two constituents of isomalt, the share of each componentmay vary between 43–57 % depending on the conditions of hydrogenation.An alternative possibility is the direct cultivation of suitable microorganismssuch as P. rubrum on sucrose-containing juices obtained during the production of beet and cane sugar. It is claimed that glucose and fructose produced during thetransformation are consumed by the microorganisms which results in loweramounts of by-products. |
| Pharmaceutical Applications | Isomalt is a noncariogenic excipient used in a variety ofpharmaceutical preparations including tablets or capsules, coatings,sachets, and suspensions, and in effervescent tablets. It can also beused in direct compression and wet granulation. In buccal applications such as chewable tablets it is commonlyused because of its negligible negative heat of solution, mildsweetness, and ‘mouth feel’. It is also used widely in lozenges,sugar-free chewing gum, and hard-boiled candies, and as asweetening agent in confectionery for diabetics. |
| Safety | Isomalt is used in oral pharmaceutical formulations, confectionery,and food products. It is generally regarded as a nontoxic,nonallergenic, and nonirritant material. Toxicological and metabolic studies on isomalt have beensummarized in a WHO report prepared by the FAO/WHO ExpertCommittee (JECFA), resulting in an acceptable daily intake of ‘notspecified’. The glycosidic linkage between the mannitol or sorbitol moietyand the glucose moiety is very stable, limiting the hydrolysis andabsorption of isomalt in the small intestine. There is no significantincrease in the blood glucose level after oral intake, and glycemicresponse is very low, making isomalt suitable for diabetics. Themajority of isomalt is fermented in the large intestine. In general,isomalt is tolerated very well, although excessive consumption mayresult in laxative effects. Isomalt is not fermented by bacteria present in the mouth;therefore no significant amount of organic acid is produced thatattacks tooth enamel. |
| storage | Isomalt has very good thermal and chemical stability. When it ismelted, no changes in the molecular structure are observed. It exhibits considerable resistance to acids and microbial influences.Isomalt is non-hygroscopic, and at 25°C does not significantlyabsorb additional water up to a relative humidity (RH) of 85%;paracetamol (acetaminophen) tablets based on isomalt were storedfor 6 months at 85% RH at 20°C and retained their physicalaspect. If stored under normal ambient conditions, isomalt is chemicallystable for many years. When it is stored in an unopened container at20°C and 60% RH, a re-evaluation after 3 years is recommended. |
| Regulatory Status | GRAS listed. Accepted as a food additive in Europe. |
Isomalt Preparation Products And Raw materials
| Raw materials | D(-)-Fructose-->D-Glucose monohydrate-->PALATINOSE-->6-O-alpha-D-glucopyranosyl-alpha-D-fructofuranose-->Sucrose |
