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20942-99-8 , 1-O-(a-Glucopyranosyl)-D-mannitol

20942-99-8 , 1-O-(a-Glucopyranosyl)-D-mannitol ,
1,1-GPM; 6-O-a-D-Glucopyranosyl-D-mannitol
C12H24O11·2H2O / 380.34
MFCD03414194

1-O-(a-Glucopyranosyl)-D-mannitol

1,1-GPM; 6-O-a-D-Glucopyranosyl-D-mannitol

Isomalt is a sugar substitute used as a sugar replacer in food and confectionery products. It is well-recognized for its unique properties, including stability, low hygroscopicity, and resistance to browning during heat processing. Isomalt has become an attractive alternative to sugar due to its low calorie content and its beneficial effects on dental health. The following paper aims to provide information concerning the definition, background, and characteristics of isomalt. It will also cover topics such as the synthesis and characterization of the chemical compound, biological properties, and applications in scientific experiments. Furthermore, a review of the current state of research, future directions for research, and potential implications in various fields of research and industry will be discussed in detail.

Definition and Background

Isomalt is a sugar alcohol that was first synthesized by the Danish company, Danisco, in the late 1970s. It is a mixture of two disaccharides, namely palatinose and isomaltose, which are derived from the fermentation of sucrose. Isomalt is made of three components, namely, glucose, fructose, and mannitol, which are linked by chemical bonds. The chemical formula for isomalt is C12H24O11·H2O, with a molecular weight of 344.3 g/mol. Upon hydrolysis, isomalt yields only glucose and mannitol.

Physical and Chemical Properties

Isomalt is a white crystalline powder or granular substance that is easily soluble in water. The chemical compound is a stable carbohydrate that is resistant to moisture and heat. It possesses a low degree of hygroscopicity, which means that it has a low affinity for moisture. This property makes it an excellent ingredient for dry foods like cereals and snacks. When heated, isomalt does not undergo significant browning, which makes it suitable for use in confectionery products. Additionally, isomalt has a low glycemic index of 2 and a low calorie content of 2 kcal/g, making it an ideal sugar substitute for individuals on a calorie-restricted diet.

Synthesis and Characterization

Isomalt is synthesized through the fermentation of sucrose by a microorganism called Erwinia. The fermentation process yields a mixture of six-carbon sugars, which are then purified to obtain isomalt. The purity of isomalt is dependent on the purification process employed. Purification techniques such as crystallization, ion exchange chromatography, and reverse osmosis are commonly used to purify isomalt. Characterization of isomalt is typically conducted using analytical methods such as HPLC, FTIR, and NMR spectroscopy.

Analytical Methods

High-performance liquid chromatography (HPLC) is a widely used analytical technique in the analysis of isomalt. This technique separates and detects components of the compound based on their chemical properties. Fourier transform infrared spectroscopy (FTIR) is an analytical method that identifies the functional groups in the chemical compound. Nuclear magnetic resonance (NMR) spectroscopy determines the structure of isomalt by analyzing the sequences of signals generated by atomic nuclei in a magnetic field.

Biological Properties

Isomalt has been shown to possess several biological properties that make it an attractive alternative to sugar. Firstly, it has a low glycemic index, which means that it does not cause a rapid rise in blood sugar levels. Secondly, isomalt promotes dental health since it is resistant to oral bacteria that cause tooth decay. Thirdly, isomalt is resistant to human digestive enzymes, which means that it produces fewer calories than sugar.

Toxicity and Safety in Scientific Experiments

Isomalt is generally regarded as safe for human consumption. The scientific literature reports that isomalt has low oral acute toxicity and does not cause adverse effects when ingested. Additionally, animal studies have shown no significant toxic effects when animals were exposed to high levels of isomalt. However, studies have shown that high doses of isomalt may cause gastrointestinal disturbances such as bloating, flatulence, and diarrhea.

Applications in Scientific Experiments

Isomalt has been extensively used as a sugar replacer in scientific studies. It is commonly used in studies that investigate the metabolism of carbohydrates, energy balance, and the physiological effects of dietary carbohydrates. Isomalt is also used as an ingredient in the production of functional foods and nutraceuticals.

Current State of Research

The current state of research on isomalt centers around its potential benefits in various fields of research and industry. Researchers are investigating the use of isomalt in the production of hydrogen, ethanol, and isomaltulose. Additionally, there is ongoing research on the development of products that combine isomalt with other functional ingredients like vitamins, minerals, and antioxidants.

Potential Implications in Various Fields of Research and Industry

Isomalt has potential applications in various fields of research and industry, including food science and technology, pharmaceuticals, and biotechnology. It is a versatile ingredient that can be used as a sugar replacer in beverages, confectionery products, and baked goods. Isomalt can also be used as a low-calorie sugar replacer in pharmaceutical products such as cough syrups, lozenges, and tablets.

Limitations and Future Directions

Despite the potential benefits of isomalt, there are limitations to its use in the food industry. One of the challenges of using isomalt is its high cost of production, which limits its widespread use as a sugar replacer. Additionally, isomalt has a lower sweetness intensity than sugar, which requires its use in combination with other sweeteners to achieve the desired sweetness level. With these limitations in mind, future directions for research may focus on enhancing the sweetness intensity of isomalt while reducing the cost of production. Other potential areas of research may include the use of isomalt in the production of biodegradable plastics and the identification of the mechanisms underlying the physiological effects of isomalt.

Conclusion

Isomalt is a valuable sugar replacer that possesses unique properties that make it an attractive alternative to sugar. Despite its potential benefits, there are limitations to its use in the food industry, which require further research to address. However, the growing interest in functional foods and low-calorie products is expected to drive the growth of isomalt usage in the future. As research into isomalt continues, it is logical to expect that the chemical compound's potential in various applications will continue to be explored, and future advances in its synthesis, characterization, and applications will undoubtedly follow.

CAS Number20942-99-8
Product NameIsomalt
IUPAC Name(2R,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
Molecular Formula6-O-α-D-Glucopyranosyl-D-sorbitol: C12H24O11; 1-O-α-D-Glucopyranosyl-D-mannitol dihydrate: C12H24O11.2H2O
C12H24O11
Molecular Weight344.31 g/mol
InChIInChI=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
InChI KeySERLAGPUMNYUCK-DCUALPFSSA-N
SMILESC(C1C(C(C(C(O1)OCC(C(C(C(CO)O)O)O)O)O)O)O)O
SolubilitySoluble in water, very slightly soluble in ethanol.
In water, 1X10+6 mg/L /miscible/ at 25 °C (est)
SynonymsD-Glucitol, 6-O-alpha-D-glucopyranosyl-, mixt. with 1-O-alpha-D-glucopyranosyl-D-mannitol, D-Glucitol, 6-O-alpha-D-glucopyranosyl-, mixture with 1-O-alpha-D-glucopyranosyl-D-mannitol, isomalt, Palatinit
Canonical SMILESC(C1C(C(C(C(O1)OCC(C(C(C(CO)O)O)O)O)O)O)O)O
Isomeric SMILESC([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC[C@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O)O)O)O)O


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