13718-94-0

Basic information

• Product Name: PALATINOSE
• Synonyms: PALATINOSE HYDRATE;PALATINOSE MONOHYDRATE;6-O-ALPHA-D-GLUCOPYRANOSYL-D-FRUCTOFURANOSE HYDRATE;6-O-ALPHA-D-GLUCOPYRANOSYL-D-FRUCTOSE;6-O-A-D-GLC-D-FRU;6-O-A-D-GLUCOPYRANOSYL-D-FRUCTOFURANOSE;ISOMALTULOSE HYDRATE;Palatinose,6-O-.alpha.-D-glucopyranosyl-D-fructose
• CAS NO: 13718-94-0
• Molecular Formula: C₁₂H₂₂O₁₁
• Molecular Weight: 342.3
• EINECS: 237-282-1
• Product Categories: Basic Sugars (Mono & Oligosaccharides);Biochemistry;Disaccharides;Sugars
• Mol File: 13718-94-0.mol
• Article Data: 8

Chemical Properties

• Melting Point: 125-128 °C
• Boiling Point: 784.843 °C at 760 mmHg
• Flash Point: 292.547 °C
• Appearance: White/Powder
• Density: 1.694 g/cm³
• Vapor Pressure: 1.14E-21mmHg at 25°C
• Refractive Index: 99 ° (C=1, H2O)
• Storage Temp.: Refrigerator
• Solubility: Methanol (Slightly), Water (Slightly, Heated, Sonicated)
• PKA: 11.85±0.20(Predicted)
• Water Solubility: almost transparency
• Merck: 14,5182
• CAS DataBase Reference: PALATINOSE(CAS DataBase Reference)
• NIST Chemistry Reference: PALATINOSE(13718-94-0)
• EPA Substance Registry System: PALATINOSE(13718-94-0)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-37/38-41-48
• Safety Statements: 22-24/25-45-36/37/39-26
• WGK Germany: 3
• RTECS: LS7175420
• F: 3-10
• Hazardous Substances Data: 13718-94-0(Hazardous Substances Data)

Usage

Uses

Palatinose Hydrate is a natural occurring disaccharide composed of α-1,6-linked glucose and fructose and can be used as an alternative sugar. Because it is absorbed more slowly than sucrose it can be used as a sweetener for diabetic patients.

InChI:InChI=1/C12H22O11/c13-1-4-6(15)8(17)9(18)11(22-4)21-2-5-7(16)10(19)12(20,3-14)23-5/h4-11,13-20H,1-3H2/t4-,5-,6-,7-,8+,9-,10+,11+,12+/m1/s1

Synthetic route

Sucrose (57-50-1) → isomaltulose (13718-94-0)

Conditions	Yield
With protaminobacter rubrum

isomaltose → isomaltulose (13718-94-0)

Conditions	Yield
With ammonium hydroxide

Sucrose (57-50-1) → 1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) + isomaltulose (13718-94-0)

Conditions	Yield
With sucrose isomerase In aq. phosphate buffer at 30℃; for 0.333333h; pH=6; Kinetics; pH-value; Temperature; Enzymatic reaction;

D-Val-OH (640-68-6) + tert-butylisonitrile (119072-55-8, 7188-38-7) + isomaltulose (13718-94-0) → (3S,5R)-N-(tert-butyl)-5-isopropyl-6-oxo-3-((1R,2S,3R)-1,2,3-trihydroxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yl)oxy)butyl)morpholine-3-carboxamide + (3R,5R)-N-(tert-butyl)-5-isopropyl-6-oxo-3-((1R,2S,3R)-1,2,3-trihydroxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yl)oxy)butyl)morpholine-3-carboxamide

Conditions	Yield
With trifluoroethanol; 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 60℃; for 16h; Overall yield = 25 %; Overall yield = 90 mg; stereoselective reaction;	A 45% B n/a

nickel (7440-02-0) + ruthenium (7440-18-8) + isomaltulose (13718-94-0) → isomaltitol (534-73-6)

Conditions	Yield
With hydrogen; pyrographite In water

ruthenium (7440-18-8) + isomaltulose (13718-94-0) → isomaltitol (534-73-6)

Conditions	Yield
With hydrogen; nickel In water

isomaltulose (13718-94-0) → isomaltitol (534-73-6)

Conditions	Yield
With hydrogen; ruthenium In water
With hydrogen; ruthenium In water
With hydrogen; ruthenium In water
With hydrogen; ruthenium In water

D-Fructose (57-48-7) + D-Glucose (2280-44-6) + Sucrose (57-50-1) + isomaltose (499-40-1) + 1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) + isomaltulose (13718-94-0) → α-D-glucopyranosyl-(1->6)-D-gulitol (20942-96-5) + 1-O-α-D-glucopyranosyl-D-mannitol (20942-99-8) + mannitol (69-65-8) + D-sorbitol (50-70-4) + isomaltitol (534-73-6)

Conditions	Yield
With hydrogen; nickel In water at 20 - 130℃; under 22502.3 Torr; Product distribution / selectivity; Autoclave;

...Expand

D-Fructose (57-48-7) + D-Glucose (2280-44-6) + isomaltose (499-40-1) + 1-O-α-D-glucopyranosyl-β-D-fructose (51411-23-5) + isomaltulose (13718-94-0) → α-D-glucopyranosyl-(1->6)-D-gulitol (20942-96-5) + 1-O-α-D-glucopyranosyl-D-mannitol (20942-99-8) + mannitol (69-65-8) + D-sorbitol (50-70-4) + isomaltitol (534-73-6)

Conditions	Yield
With hydrogen; nickel In water at 20 - 130℃; under 22502.3 - 97509.8 Torr; Product distribution / selectivity; Autoclave;

...Expand

isomaltulose (13718-94-0) → D-glucose (50-99-7)

Conditions	Yield
With rat intestinal α-glucosidase at 37℃; for 0.333333h; pH=6.8; aq. phosphate buffer;

L-valine (72-18-4) + tert-butylisonitrile (119072-55-8, 7188-38-7) + isomaltulose (13718-94-0) → (3R,5S)-N-(tert-butyl)-5-isopropyl-6-oxo-3-((1R,2S,3R)-1,2,3-trihydroxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yl)oxy)butyl)morpholine-3-carboxamide + (3S,5S)-N-(tert-butyl)-5-isopropyl-6-oxo-3-((1R,2S,3R)-1,2,3-trihydroxy-4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-tetrahydro-2H-pyran-2-yl)oxy)butyl)morpholine-3-carboxamide

Conditions	Yield
With trifluoroethanol; 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 60℃; for 16h; Overall yield = 45 %; Overall yield = 162.7 mg; stereoselective reaction;	A n/a B n/a

isomaltulose (13718-94-0) → 1-O-α-D-glucopyranosyl-D-mannitol (20942-99-8) + isomaltitol (534-73-6)

Conditions	Yield
With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; dichloro(benzene)ruthenium(II) dimer; hydrogen In methanol at 100℃; for 16h; Autoclave; Overall yield = 84 percent; Overall yield = 1.14 g; diastereoselective reaction;	A n/a B n/a
With (S)-(+)-5,5’-bis[di(3,5-di-tert-butyl-4-methoxyphenyl)phosphino]-4,4’-bi-1,3-benzodioxole; dichloro(benzene)ruthenium(II) dimer; hydrogen In methanol at 100℃; for 16h; Autoclave; diastereoselective reaction;	A n/a B n/a

Upstream product

• 24822-33-1 D-isomaltose 
• 59-92-7 levodopa 
• 57-50-1 Sucrose 

Downstream Products

• 50-99-7 D-glucose 
• 57-48-7 D-Fructose 
• 24822-33-1 D-isomaltose 
• 3458-28-4 D-Mannose 
• 20942-99-8 1-O-α-D-glucopyranosyl-D-mannitol 
• 534-73-6 isomaltitol 
• 1462942-81-9 4-[(1'R,2'S,3'R)-4′-(α-D-glucopyranosyloxy)-1',2',3'-trihydroxybutyl]-2-phenylimidazole 
• 55-21-0 benzamide 
• 20942-96-5 α-D-glucopyranosyl-(1->6)-D-gulitol 
• 69-65-8 mannitol 
• 50-70-4 D-sorbitol 
• 209977-51-5 N-acetyl-6-O-(α-D-glucopyranosyl)-D-glucosamine 
• 67-47-0 5-hydroxymethyl-2-furfuraldehyde 
• 4746-18-3 isomaltulose phenylosazone 

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Palatinose is a non-cariogenic disaccharide obtained from the enzymatic conversion of sucrose, used in food industries as a sugar substitute. Free and Ca-alginate immobilized cells of Erwinia sp. D12 were used to produce palatinose from sucrose. Palatinose production was studied in a repeated-ba...detailed

Potato tubers as bioreactors for PALATINOSE (cas 13718-94-0) production09/24/2019

Palatinose (isomaltulose, 6-O-α-d-glucopyranosyl-d-fructose) is a structural isomer of sucrose with very similar physico-chemical properties. Due to its non-cariogenicity and low calorific value it is an ideal sugar substitute for use in food production. Palatinose is produced on an industrial ...detailed

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Acceptor specificity for intermolecular transglucosylation reaction of amylomaltase from Corynebacterium glutamicum was investigated using starch as glucosyl donor and various saccharide acceptors. Maltooligosaccharides (G1–G4), mannose, palatinose and sucrose were efficient acceptors; the best...detailed

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Sucrose isomerase (SIase) is the key enzyme in the enzymatic synthesis of isomaltulose. Mesoporous titanium dioxide (M-TiO2) and ε-poly-L-lysine-functionalized M-TiO2 (EPL-M-TiO2) were prepared as carriers for immobilizing SIase. SIase was effectively immobilized on EPL-M-TiO2 (SI-EPL-M-TiO2) with an enzyme activity of 39.41 U/g, and the enzymatic activity recovery rate up to 93.26%. The optimal pH and temperature of immobilized SIase were 6.0 and 30 °C, respectively. SI-EPL-M-TiO2 was more stable in pH and thermal tests than SIase immobilized on M-TiO2 and free SIase. Km of SI-EPL-M-TiO2 was 204.92 mmol/L, and νmax was 45.7 μmol/L/s. Batch catalysis reaction of sucrose by SI-EPL-M-TiO2 was performed under the optimal conditions. The half-life period of SI-EPL-M-TiO2 under continuous reaction was 114 h, and the conversion rate of sucrose after 16 batches consistently remained at around 95%, which indicates that SI-EPL-M-TiO2 has good operational stability. Thus, SI-EPL-M-TiO2 can be used as a biocatalyst in food industries.

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Isomerization of disaccharides (maltose, isomaltose, cellobiose, lactose, melibiose, palatinose, sucrose, and trehalose) was investigated in subcritical aqueous ethanol. A marked increase in the isomerization of aldo-disaccharides to keto-disaccharides was noted and their hydrolytic reactions were suppressed with increasing ethanol concentration. Under any study condition, the maximum yield of keto-disaccharides produced from aldo-disaccharides linked by β-glycosidic bond was higher than that produced from aldo-disaccharides linked by α-glycosidic bond. Palatinose, a keto-disaccharide, mainly underwent decomposition rather than isomerization in subcritical water and subcritical aqueous ethanol. No isomerization was noted for the non-reducing disaccharides trehalose and sucrose. The rate constant of maltose to maltulose isomerization almost doubled by changing solvent from sub-critical water to 80 wt% aqueous ethanol at 220°C. Increased maltose monohydrate concentration in feed decreased the conversion of maltose and the maximum yield of maltulose, but increased the productivity of maltulose. The maximum productivity of maltulose was ca. 41 g/(h kg-solution).

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