isomaltulose

6-O-alpha-D-glucopyranosyl-D-fructose

CAS: 13718-94-0 C12 H22 O11 MW: 342.29854000 sweet

Identification

Nameisomaltulose
IUPAC(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
CAS Number13718-94-0
EINECS237-282-1
FDA UNIIV59P50X4UY
Molecular FormulaC12 H22 O11
Molecular Weight342.29854000
MDL NumberMFCD00076094
Nikkaji NumberJ16.052K
Beilstein0093820

Regulatory

FDA/DG SANTE Petitions, Reviews, NoticesGRN 184

Physical Properties

Appearance white powder (est)
Assay 95.00 to 100.00
Food Chemicals Codex Listed No
Boiling Point 784.00 to 785.00 °C. @ 760.00 mm Hg (est)
Flash Point 559.00 °F. TCC ( 292.50 °C. ) (est)
logP (o/w) -2.941 (est)
Soluble in water, 1e+006 mg/L @ 25 °C (est)

Organoleptic Properties

Taste Description sweet

Safety Information

Oral/Parenteral ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorysweeteners, flavor enhancers
Recommendation for isomaltulose usage levels up tonot for fragrance use.

BOC Sciences

Best of Chemicals Supplier

Quality supplier of research chemicals and biochemicals including inhibitors, building blocks, GMP Products, impurities and metabolites, APIs for Veterinary, Natural Compounds, ADCs, Stem Cell Molecul...

View All Website 1-631-485-4226 account@bocsci.com

Glentham Life Sciences Ltd

The Chemical, Biochemical & Research Essentials Supplier

Glentham Life Sciences is a supplier of fine chemicals and raw materials with warehousing, laboratories and packaging facilities in the UK.

View All Website +44 (0) 1225 667798 info@glentham.com

Jiangyin Healthway International Trade Co., Ltd

Independent Ingredients Supplier

We provide custom synthesis and contract manufacturing from milligrams to metric tonnes.

View All Website 86-510-86023169 info@healthwaychem.com

O'Laughlin Industries Inc.

Manufacturer of chemicals and ingredients used in flavors, fragrances, food, beverages and cosmetics

Leading the Flavor and Fragrance Industry since 1980.

View All Website (973) 376-4600 olcorphk@hkstar.com

Qingdao Free Trade Zone United International Co Ltd

Quality Products

A partner in your supply chain solution.

View All Website +86-532-83893699 info@unitedint.com

Potential Uses

None Found

Natural Occurrence

found in nature

Synonyms

6-O-alpha-D- glucopyranosyl-D-fructose 6-O-alpha-dextro- glucopyranosyl-dextro-fructose palatinose (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 PubMed: Nutritional strategy to prevent fatty liver and insulin resistance independent of obesity by reducing glucose-dependent insulinotropic polypeptide responses in mice. PubMed: The effect of using isomaltulose (Palatinose™) to modulate the glycaemic properties of breakfast on the cognitive performance of children. PubMed: Synthesis and characterization of isomaltulose-derived oligosaccharides produced by transglucosylation reaction of Leuconostoc mesenteroides dextransucrase. PubMed: Development of synbiotics with inulin, palatinose, alpha-cyclodextrin and probiotic bacteria. PubMed: Comparison of the effects of slowly and rapidly absorbed carbohydrates on postprandial glucose metabolism in type 2 diabetes mellitus patients: a randomized trial. PubMed: Transglycosylations employing recombinant α- and β-galactosidases and novel donor substrates. PubMed: Current studies on sucrose isomerase and biological isomaltulose production using sucrose isomerase. PubMed: Crystallization and preliminary X-ray crystallographic analysis of α-glucosidase HaG from Halomonas sp. strain H11. PubMed: Functional characterization of the sucrose isomerase responsible for trehalulose production in plant-associated Pectobacterium species. PubMed: The structural basis of Erwinia rhapontici isomaltulose synthase. PubMed: The effect of lactose-isomaltulose-containing growing-up milks on cognitive performance of Indonesian children: a cross-over study. PubMed: Is there a specific role for sucrose in sports and exercise performance? PubMed: Simple, fast, and efficient process for producing and purifying trehalulose. PubMed: Mutations inducing an active-site aperture in Rhizobium sp. sucrose isomerase confer hydrolytic activity. PubMed: Potential applications of carbohydrases immobilization in the food industry. PubMed: Enhancing isomaltulose production by recombinant Escherichia coli producing sucrose isomerase: culture medium optimization containing agricultural wastes and cell immobilization. PubMed: Mature-stem expression of a silencing-resistant sucrose isomerase gene drives isomaltulose accumulation to high levels in sugarcane. PubMed: Influence of processing on the volatile profile of strawberry spreads made with isomaltulose. PubMed: The effect of selected synbiotics on microbial composition and short-chain fatty acid production in a model system of the human colon. PubMed: Transcriptional analysis of prebiotic uptake and catabolism by Lactobacillus acidophilus NCFM. PubMed: Combining protein and carbohydrate increases postprandial insulin levels but does not improve glucose response in patients with type 2 diabetes. PubMed: Insight into the role of sugars in bud burst under light in the rose. PubMed: Metabolic effects of replacing sucrose by isomaltulose in subjects with type 2 diabetes: a randomized double-blind trial. PubMed: Immobilization of glucosyltransferase from Erwinia sp. using two different techniques. PubMed: Postprandial substrate use in overweight subjects with the metabolic syndrome after isomaltulose (Palatinose™) ingestion. PubMed: Reduced glycaemic and insulinaemic responses following trehalose and isomaltulose ingestion: implications for postprandial substrate use in impaired glucose-tolerant subjects. PubMed: Microbial sucrose isomerases: producing organisms, genes and enzymes. PubMed: Mechanism-oriented redesign of an isomaltulose synthase to an isomelezitose synthase by site-directed mutagenesis. PubMed: Exercise dose and insulin sensitivity: relevance for diabetes prevention. PubMed: Isomaltulose improves glycemia and maintains run performance in type 1 diabetes. PubMed: Isomaltulose is actively metabolized in plant cells. PubMed: The effect of high lactose-isomaltulose on cognitive performance of young children. A double blind cross-over design study. PubMed: Field performance of transgenic sugarcane expressing isomaltulose synthase. PubMed: Isomaltulose production via yeast surface display of sucrose isomerase from Enterobacter sp. FMB-1 on Saccharomyces cerevisiae. PubMed: Immobilization of Erwinia sp. D12 Cells in Alginate-Gelatin Matrix and Conversion of Sucrose into Isomaltulose Using Response Surface Methodology. PubMed: Sucrose isomerase and its mutants from Erwinia rhapontici can synthesise α-arbutin. PubMed: GLP-1 secretion in response to oral and luminal palatinose (isomaltulose) in rats. PubMed: A new immune-modulating diet enriched with whey-hydrolyzed peptide, fermented milk, and isomaltulose attenuates gut ischemia-reperfusion injury in mice. PubMed: A combined insulin reduction and carbohydrate feeding strategy 30 min before running best preserves blood glucose concentration after exercise through improved fuel oxidation in type 1 diabetes mellitus. PubMed: Studies on absorption and metabolism of palatinose (isomaltulose) in rats. PubMed: Microbial production of palatinose through extracellular expression of a sucrose isomerase from Enterobacter sp. FMB-1 in Lactococcus lactis MG1363. PubMed: Cloning and characterization of a sucrose isomerase from Erwinia rhapontici NX-5 for isomaltulose hyperproduction. PubMed: Isomaltulose Improves Postexercise Glycemia by Reducing CHO Oxidation in T1DM. PubMed: Transgenic expression of trehalulose synthase results in high concentrations of the sucrose isomer trehalulose in mature stems of field-grown sugarcane. PubMed: Palatinose-blended sugar compared with sucrose: different effects on insulin sensitivity after 12 weeks supplementation in sedentary adults. PubMed: Novel findings on the metabolic effects of the low glycaemic carbohydrate isomaltulose (Palatinose). PubMed: Manipulation of glycemic response with isomaltulose in a milk-based drink does not affect cognitive performance in healthy adults. PubMed: Effect of concentration and substrate flow rate on isomaltulose production from sucrose by Erwinia sp. cells immobilized in calcium-alginate using packed bed reactor. PubMed: Sucrose: A prospering and sustainable organic raw material. PubMed: Gene cloning, protein characterization, and alteration of product selectivity for the trehalulose hydrolase and trehalulose synthase from "Pseudomonas mesoacidophila" MX-45. PubMed: Safer glycemic control using isomaltulose-based enteral formula: a pilot randomized crossover trial. PubMed: Reduced glycaemic and insulinaemic responses following isomaltulose ingestion: implications for postprandial substrate use. PubMed: Glucosylation of raffinose via alternansucrase acceptor reactions. PubMed: Molecular cloning and functional characterization of a sucrose isomerase (isomaltulose synthase) gene from Enterobacter sp. FMB-1. PubMed: Slowly digestible carbohydrate sources can be used to attenuate the postprandial glycemic response to the ingestion of diabetes-specific enteral formulas. PubMed: Structural determinants of product specificity of sucrose isomerases. PubMed: Isomaltulose production from sucrose by Protaminobacter rubrum immobilized in calcium alginate. PubMed: Beneficial effects on glucose metabolism of chronic feeding of isomaltulose versus sucrose in rats. PubMed: Isomalt production by cloning, purifying and expressing of the MDH gene from Pseudomonas fluorescens DSM 50106 in different strains of E. coli. PubMed: [Physiological and biochemical properties of the bacterium Erwinia rhapontici, a producer of isomaltulose synthase]. PubMed: Palatinose and oleic acid act together to prevent pancreatic islet disruption in nondiabetic obese Zucker rats. PubMed: Food labeling: health claims; dietary noncariogenic carbohydrate sweeteners and dental caries. Final rule. PubMed: Inhibitory action of palatinose and its hydrogenated derivatives on the hydrolysis of alpha-glucosylsaccharides in the small intestine. PubMed: Isomaltose production by modification of the fructose-binding site on the basis of the predicted structure of sucrose isomerase from "Protaminobacter rubrum". PubMed: Recent progress in the synthesis of carbohydrate-based amphiphilic materials: the examples of sucrose and isomaltulose. PubMed: Molecular and physiological role of the trehalose-hydrolyzing alpha-glucosidase from Thermus thermophilus HB27. PubMed: Role of periplasmic trehalase in uptake of trehalose by the thermophilic bacterium Rhodothermus marinus. PubMed: [Production of fructooligosaccharide syrup from sucrose in combination with palatinose and trehalose]. PubMed: Dietary palatinose and oleic acid ameliorate disorders of glucose and lipid metabolism in Zucker fatty rats. PubMed: Trehalulose synthase native and carbohydrate complexed structures provide insights into sucrose isomerization. PubMed: A palatinose-based balanced formula improves glucose tolerance, serum free fatty acid levels and body fat composition. PubMed: Inhibitory effect of palatinose on glucose absorption in everted rat gut. PubMed: Exogenous oxidation of isomaltulose is lower than that of sucrose during exercise in men. PubMed: A new colorimetric method for determining the isomerization activity of sucrose isomerase. PubMed: Effects of a novel palatinose based enteral formula (MHN-01) carbohydrate-adjusted fluid diet in improving the metabolism of carbohydrates and lipids in patients with esophageal cancer complicated by diabetes mellitus. PubMed: Doubled sugar content in sugarcane plants modified to produce a sucrose isomer. PubMed: Isomaltulose production using free cells: optimisation of a culture medium containing agricultural wastes and conversion in repeated-batch processes. PubMed: Effects of a palatinose-based liquid diet (Inslow) on glycemic control and the second-meal effect in healthy men. PubMed: Conversion of sucrose into isomaltulose by Enterobacter sp. FMB1, an isomaltulose-producing microorganism isolated from traditional Korean food. PubMed: Application of response surface methodology to cell immobilization for the production of palatinose. PubMed: Sucrose substitutes and their role in caries prevention. PubMed: Molecular characterization of the alpha-glucosidase activity in Enterobacter sakazakii reveals the presence of a putative gene cluster for palatinose metabolism. PubMed: Overexpression, purification, crystallization and preliminary diffraction studies of the Protaminobacter rubrum sucrose isomerase SmuA. PubMed: Expression, purification, crystallization and preliminary X-ray crystallographic studies of the trehalulose synthase MutB from Pseudomonas mesoacidophila MX-45. PubMed: Characterization of the highly efficient sucrose isomerase from Pantoea dispersa UQ68J and cloning of the sucrose isomerase gene. PubMed: The high-affinity maltose/trehalose ABC transporter in the extremely thermophilic bacterium Thermus thermophilus HB27 also recognizes sucrose and palatinose. PubMed: Klebsiella singaporensis sp. nov., a novel isomaltulose-producing bacterium. PubMed: Comparative effect of repeated ingestion of difructose anhydride III and palatinose on the induction of gastrointestinal symptoms in humans. PubMed: Effect of a novel palatinose-based liquid balanced formula (MHN-01) on glucose and lipid metabolism in male Sprague-Dawley rats after short- and long-term ingestion. PubMed: Characterization of Pantoea dispersa UQ68J: producer of a highly efficient sucrose isomerase for isomaltulose biosynthesis. PubMed: Fermentation of five sucrose isomers by human dental plaque bacteria. PubMed: Enhanced conversion of sucrose to isomaltulose by a mutant of Erwinia rhapontici. PubMed: Production of palatinose using Serratia plymuthica cells immobilized in chitosan. PubMed: The effect of palatinose on mental concentration in humans. PubMed: Straightforward route for anchoring a glucosyl moiety onto nucleophilic species: reaction of amines and alcohols with carboxymethyl 3,4,6-tri-O-acetyl-alpha-D-glucopyranoside 2-O-lactone. PubMed: Substrate induction of isomaltulose synthase in a newly isolated Klebsiella sp. LX3. PubMed: Isomaltulose synthase (PalI) of Klebsiella sp. LX3. Crystal structure and implication of mechanism. PubMed: Distinct sucrose isomerases catalyze trehalulose synthesis in whiteflies, Bemisia argentifolii, and Erwinia rhapontici. PubMed: Structural and functional analysis of a putative gene cluster for palatinose transport on the linear chromosome of Agrobacterium tumefaciens MAFF301001. PubMed: Sugar-regulated expression of a putative hexose transport gene in grape. PubMed: A motif rich in charged residues determines product specificity in isomaltulose synthase. PubMed: Decreased sucrose content triggers starch breakdown and respiration in stored potato tubers (Solanum tuberosum). PubMed: Expression, crystallization and preliminary X-ray analysis of isomaltulose synthase (PalI) from Klebsiella sp. LX3. PubMed: Glycosidation of fructose-containing disaccharides using MCM-41 material as the catalyst. PubMed: 13-Week oral toxicity study with isomaltulose (Palatinose) in rats. PubMed: Isomaltulose (Palatinose): a review of biological and toxicological studies. PubMed: Potato tubers as bioreactors for palatinose production. PubMed: Isomaltulose synthase from Klebsiella sp. strain LX3: gene cloning and characterization and engineering of thermostability. PubMed: Metabolizable and non-metabolizable sugars activate different signal transduction pathways in tomato. PubMed: High-level production of the non-cariogenic sucrose isomer palatinose in transgenic tobacco plants strongly impairs development. PubMed: Phosphorylation and metabolism of sucrose and its five linkage-isomeric alpha-D-glucosyl-D-fructoses by Klebsiella pneumoniae. PubMed: The sucrose analog palatinose leads to a stimulation of sucrose degradation and starch synthesis when supplied to discs of growing potato tubers. PubMed: Responses of the ant Lasius niger to various compounds perceived as sweet in humans: a structure-activity relationship study. PubMed: Cloning and characterization of the gene cluster for palatinose metabolism from the phytopathogenic bacterium Erwinia rhapontici. PubMed: Assessment of acid production by various human oral micro-organisms when palatinose or leucrose is utilized. PubMed: Di- and oligosaccharide substrate specificities and subsite binding energies of pig intestinal glucoamylase-maltase. PubMed: Effects of frequent mouthrinses with palatinose and xylitol on dental plaque. PubMed: Bacillus thermoamyloliquefaciens KP1071 alpha-glucosidase II is a thermostable M(r) 540,000 homohexameric alpha-glucosidase with both exo-alpha-1,4-glucosidase and oligo-1,6-glucosidase activities. PubMed: Embryotoxicity/teratogenicity study with isomaltulose (Palatinose) in rats. PubMed: The effects of isomaltulose, isomalt, and isomaltulose-based oligomers on mineral absorption and retention. PubMed: Urinary excretion by dogs of intravenously administered simple sugars. PubMed: The effects of isomaltulose-based oligomers feeding and calcium deficiency on mineral retention in rats. PubMed: Industrial application of immobilized biocatalysts in Japan. PubMed: Transglucosylation with 6'-chloro-6'-deoxysucrose and immobilized isomaltulose-producing microorganisms using 2,2-dimethyl-1,3-dioxolane-4-methanol and its related compounds as acceptors. Steric and chemical requirement of the glucosyl acceptor. PubMed: Characterization of alpha-glucosyltransferase from Pseudomonas mesoacidophila MX-45. PubMed: Downstream processing of sucrose 6-glucosylmutase and production of isomaltulose, a non-cariogenic, low-caloric sweetener. PubMed: Synthesis of dispirodioxanyl pseudo-oligosaccharides by selective protonic activation of isomeric glycosylfructoses in anhydrous hydrogen fluoride. PubMed: Investigation of sucrose synthase from rice for the synthesis of various nucleotide sugars and saccharides. PubMed: Selective protonic activation of isomeric glycosylfructoses with pyridinium poly(hydrogen fluoride) and synthesis of spirodioxanyl oligosaccharides. PubMed: Trehalulose does not induce dental caries in rats infected with mutans streptococci. PubMed: First purification and characterization of a sucrase-isomaltase from goose kidney microvillous membrane. PubMed: Plaque formation of dietary isomaltulose in humans. PubMed: Evaluation of a model for short-term clinical testing of cariogenicity. PubMed: Usefulness of palatinose as a caloric sweetener for diabetic patients. PubMed: Isomaltulose "palatinose". An anticariogenic substitute for glucose. PubMed: Hydrolysis of alpha-D-glucopyranosyl-1,6-sorbitol and alpha-D-glucopyranosyl-1,6-mannitol by rat intestinal disaccharidases. PubMed: [Sugar substitutes--new substances]. PubMed: New experiments on Palatinose (Isomaltulose) as a sugar substitute. PubMed: [Effect of candy containing palatinose on human dental plaque formation]. PubMed: [A stepwise method of evaluating sugar substitutes--a preliminary study using enzymes. 2. Beta-fructosidase from yeast]. PubMed: Effects of parenteral palatinose on glucose metabolism in normal and streptozotocin diabetic rats. PubMed: Palatinose as a potential parenteral nutrient: its metabolic effects and fate after oral and intravenous administration to dogs. PubMed: Changes in blood glucose and insulin after an oral palatinose administration in normal subjects. PubMed: [New sucrose substitutes]. PubMed: Isomaltulose production using immobilized cells. PubMed: Microbiological aspects of some caloric sugar substitutes. PubMed: New trends on sweeteners in Japan. PubMed: [Non-cariogenicity of palatinose]. PubMed: [Caries-inducing activity of Palatinose syrup]. PubMed: Cariogenicity of isomaltulose (palatinose), sucrose and mixture of these sugars in rats infected with Streptococcus mutans E-49. PubMed: Palatinose--a sucrose substitute. Pilot studies. PubMed: The extraction and mechanism of a novel isomaltulose-synthesizing enzyme from Erwinia rhapontici. PubMed: [Effect of sugar substitutes on the growth and acid production of 2 types of acidogenic bacteria of the oral cavity]. PubMed: Virulence factors of Streptococcus mutans and dental caries prevention. PubMed: Effect of frequent rinses with isomaltulose (Palatinose) solution on acid production in human dental plaque. PubMed: [Oligosaccharides produced by Streptococcus mutans glucosyltransferase from sucrose with isomaltulose]. PubMed: Cariostatic effect of palatinose on experimental dental caries in rats. PubMed: [Dental caries and palatinose, a structural isomer of sucrose]. PubMed: Effect of isomaltulose on acid production and insoluble glucan synthesis by Streptococcus mutans. PubMed: Non-cariogenicity of the disaccharide palatinose in experimental dental caries of rats. PubMed: Acid production from isomaltulose, sucrose, sorbitol, and xylitol in suspensions of human dental plaque. PubMed: Carbohydrate transformations by immobilized cells. PubMed: [Inhibitory mechanism of isomaltulose for insoluble glucan synthesis by Streptococcus mutans (author's transl)]. PubMed: [Analytical characterization of palatinit (author's transl)]. PubMed: [Formation of acids by cariogenically important streptococci from sugars and sugar alcohols with special reference to isomaltitol and isomaltulose]. PubMed: Human intestinal disaccharidases and hereditary disaccharide intolerance. The hydrolysis of sucrose, isomaltose, palatinose (isomaltulose), and a 1,6-alpha-oligosaccharide (isomalto-oligosaccharide) preparation.