13718-94-0, Isomaltulose,
Palatinose,
Cas:13718-94-0
MFCD00076094
C12H22O11 / 342.3
Palatinose also known as isomaltulose is a disaccharide carbohydrate produced from sucrose, a monosaccharide. It was first discovered in 1950 by German chemists and has since been widely used as a sweetener in food and beverages, as well as a low glycemic index (GI) carbohydrate source in sports and clinical nutrition. Compared with other carbohydrates, Palatinose has a relatively low GI of 32 and is more slowly digested, offering sustained energy availability.
Physical and Chemical Properties
Palatinose’s molecular formula is C12H22O11 and can be obtained from sucrose through a fermentation process using microorganisms such as bacteria (Zymomonas mobilis) or yeast (Saccharomyces cerevisiae). It has a white crystalline appearance with a molecular weight of 342.3 g/mol and a melting point of 205°C. Palatinose is a reducing sugar and can form Maillard reaction products by reacting with free amino acids, amides, or proteins under high temperature.
Synthesis and Characterization
Palatinose synthesis can be achieved via enzymatic conversion or microbial fermentation of sucrose. Enzymatic routes usually employ glycosyltransferases such as isomaltulose synthase, while microbial fermentations utilize bacteria or yeast strains that produce isomaltulose from sucrose. To ensure the quality and purity of Palatinose, several methods of characterization such as chromatography, mass spectrometry, and nuclear magnetic resonance spectroscopy (NMR) have been used.
Analytical Methods
Several analytical methods are available for the detection and quantification of Palatinose in different applications, including high-performance liquid chromatography (HPLC), gas chromatography (GC), capillary electrophoresis (CE), and Fourier-transform infrared spectroscopy (FTIR). These methods have been utilized in food and beverage industries for quality control and regulatory compliance.
Biological Properties
Palatinose has been shown to have several beneficial biological properties such as low glycemic response, sustained energy availability, and prebiotic effect on gut microbiota. In addition, it has been found to improve insulin sensitivity, offer neuroprotection, and reduce risk factors for metabolic disorders like type 2 diabetes and obesity.
Toxicity and Safety in Scientific Experiments
Studies have demonstrated that Palatinose is generally safe and well-tolerated by humans. Acute and subacute toxicity studies have been conducted in animals with no significant adverse effects or mortality observed. Moreover, Palatinose has not been found to cause mutagenic, genotoxic, or carcinogenic effects in vitro or in vivo tests.
Applications in Scientific Experiments
Palatinose’s low glycemic index and sustained energy release make it a suitable carbohydrate source in sports and clinical nutrition. It is also utilized as a functional food ingredient, with applications in confectionery, bakery, and beverage industries, providing sweetness and texture stability. Palatinose has shown potential efficacy in various diseases such as diabetes, obesity, and Alzheimer's disease.
Current State of Research
Research on Palatinose is continuously growing, with a focus on its beneficial effects on human health, safety, and applications in various fields. In 2018, a review of Palatinose's metabolic effects was published, demonstrating promising results in improving glucose metabolism and reducing insulin resistance. Another study in 2019 showed that consuming Palatinose could enhance exercise performance. Because of its beneficial effects on health, Palatinose has found increasing application in health and medical research.
Limitations and Future Directions
Despite its promising biological properties and widespread utilization, Palatinose has some limitations that need to be considered. It tends to impart a slight sweetness to foods or drinks, which may not be tolerated by some consumers. Moreover, its high price relative to other sweeteners limits its use in mass-scale production. In the future, Palatinose could find an application as a biofuel feedstock and improve current bioethanol production processes. Furthermore, it may be utilized in medical applications like wound healing, as evidenced by recent studies showing its antimicrobial potential.
In conclusion, Palatinose provides a wide range of benefits in various scientific fields, including nutrition, medicine, and industry. Its biological properties, safety, and applications make it an attractive area for scientific research with many potential areas for future development. Advances in Palatinose research could lead to improved methods of production, utilization, and application in human medicine and industry for the benefit of society as a whole.
Title: Isomaltulose
CAS Registry Number: 13718-94-0; 58024-13-8 (monohydrate)
CAS Name: 6-O-a-D-Glucopyranosyl-D-fructose
Additional Names: 6-O-a-D-glucopyranosyl-D-fructofuranose
Trademarks: Palatinose (Sádeutsche Zucker-Aktiengesellschaft; Shin Mitsui Sugar Co.)
Molecular Formula: C12H22O11
Molecular Weight: 342.30
Percent Composition: C 42.11%, H 6.48%, O 51.41%
Literature References: Reducing disaccharide occurring naturally in honey and sugar cane juice; commercially available in crystalline (42% of the sweetness of sucrose) and molasses (70% of the sweetness of sucrose) forms. Prepn: D. Weidenhagen, S. Lorenz, DE 1049800 (1959 to Süddeutsche Zucker-Aktiengesellschaft); eidem, Z. Zuckerind. 7, 533 (1957); E. S. Sharpe et al., J. Org. Chem. 25, 1062 (1960). Clinical effects on glucose levels in diabetic patients: K. Kawai et al., Horm. Metab. Res. 21, 338 (1989). Review of cariological studies: D. Birkhed et al., Dtsch. Zahnaerztl. Z. 42, S124-S127 (1987). Review of development and properties: W. E. Irwin, P. J. Sträter in Alternative Sweeteners, L. O'Brien Nabors, R. C. Gelardi, Eds. (Marcel Dekker, Inc., New York, 1991) pp 299-307; and production and clinical activity: I. Takazoe in Progress in Sweeteners, T. H. Grenby, Ed. (Elsevier, Barking, UK, 1989) pp 143-167. Review of toxicology and metabolism: B. A. R. Lina et al., Food Chem. Toxicol. 40, 1375-1381 (2002).
Properties: Crystals as monohydrate, mp 123-124°. [a]D20 +97.2° (Weidenhagen, 1957); also reported as [a]D20 +103° (c = 1.9 in water) (Sharpe). Nonhygyroscopic, acid stable, low glycemic index.
Melting point: mp 123-124°
Optical Rotation: [a]D20 +97.2° (Weidenhagen, 1957); also reported as [a]D20 +103° (c = 1.9 in water) (Sharpe)
Use: Non-cariogenic sweetener; sugar substitute in foods and beverages.
CAS Number | 13718-94-0 |
Product Name | Palatinose |
IUPAC Name | (3S,4R,5R)-1,3,4,5-tetrahydroxy-6-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyhexan-2-one |
Molecular Formula | C12H22O11 |
Molecular Weight | 342.3 g/mol |
InChI | InChI=1S/C12H22O11/c13-1-4(15)7(17)8(18)5(16)3-22-12-11(21)10(20)9(19)6(2-14)23-12/h5-14,16-21H,1-3H2/t5-,6-,7-,8-,9-,10+,11-,12+/m1/s1 |
InChI Key | RJPPRBMGVWEZRR-WTZPKTTFSA-N |
SMILES | C(C1C(C(C(C(O1)OCC(C(C(C(=O)CO)O)O)O)O)O)O)O |
Synonyms | 6-O alpha-D-glucopyranosyl-D-fructose, D-fructose, 6-O-alpha-D-glucopyranosyl-, monohydrate, isomaltulose, isomaltulose anhydrous, isomaltulose monohydrate, palatinose, palatinose monohydrate |
Canonical SMILES | C(C1C(C(C(C(O1)OCC(C(C(C(=O)CO)O)O)O)O)O)O)O |
Isomeric SMILES | C([C@@H]1[C@H]([C@@H]([C@H]([C@H](O1)OC[C@H]([C@H]([C@@H](C(=O)CO)O)O)O)O)O)O)O |
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