7660-25-5

Basic information

• Product Name: beta-D-Fructopyranose
• Synonyms: beta-D-fructopyranose;Fructopyranose;FRUCTOSE HPLC;S(-)-FRUCTOSE;FRUCTOPYRANOSE,BETA-D-;(2R,3S,4R,5R)-2-(Hydroxymethyl)oxane-2,3,4,5-tetrol;Fructosteril;Frutabs
• CAS NO: 7660-25-5
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.16
• EINECS: 200-333-3
• Product Categories: Inhibitors;chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract
• Mol File: 7660-25-5.mol

Chemical Properties

• Melting Point: 103°C
• Boiling Point: 232.96°C (rough estimate)
• Flash Point: 196.4 °C
• Appearance: /
• Density: 1.6000
• Vapor Pressure: 1.36E-09mmHg at 25°C
• Refractive Index: 1.6170 (estimate)
• PKA: 11.52±0.70(Predicted)
• Water Solubility: 3750 g/L (20℃)
• CAS DataBase Reference: beta-D-Fructopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: beta-D-Fructopyranose(7660-25-5)
• EPA Substance Registry System: beta-D-Fructopyranose(7660-25-5)

Safety Data

• Safety Statements: S24/25:
• Hazardous Substances Data: 7660-25-5(Hazardous Substances Data)

Usage

Chemical Properties

Fructose is also called levulose or fruit sugar, C6H12O6. It is the sweetest of the common sugars, being from 1.1 to 2.0 times as sweet as sucrose. Fructose is generally found in fruits and honey. An apple is 4% sucrose, 6% fructose, and 1% glucose (by weight). A grape (Vitis labrusca) is about 2% sucrose, 8% fructose, 7% glucose, and 2% maltose (by weight) (Shallenberger).

Production Methods

Commercially processed fructose is available as white crystals, soluble in water, alcohol, and ether, with a melting point between 103 and 105 °C (217.4 and 221 °F) (decomposition). Fructose can be derived by the hydrolysis of inulin; by the hydrolysis of beet sugar followed by lime separation; and from cornstarch by enzymic or microbial action.

InChI:InChI=1/C6H12O6/c7-1-3-4(9)5(10)6(11,2-8)12-3/h3-5,7-11H,1-2H2/t3-,4-,5+,6?/m1/s1

Upstream product

• 2280-44-6 D-Glucose 
• 57-50-1 Sucrose 
• 642-88-6 α-D-lactulose 

Downstream Products

• 124-38-9 carbon dioxide 
• 1333-74-0 hydrogen 
• 13403-14-0 methyl D-fructofuranoside 
• 17460-13-8 2-(D-arabino-1',2',3',4'-tetrahydroxybutyl)-5-(D-erythro-2,3,4-trihydroxybutyl)piperazine 
• 64-18-6 formic acid 
• 13171-74-9 2,3,4,5-Tetrahydroxypentanoic acid 
• 20764-61-8 Penta-O-acetyl-β-D-fructopyranose 
• 150609-95-3 2,3,4,5-bis-O-(1-methylethylidene)-β-D-fructopyranose chlorosulfonic acid ester 
• 97240-79-4 topiramate 
• 1160926-71-5 4-(1,2:4,5-di-O-isopropylidene-β-D-fructopyranos-3-O-yl)methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole 
• 15080-25-8 1,2:4,5-di-O-isopropylidene-β-D-fructopyranose 
• 55221-54-0 1,3,4,5-Tetra-O-acetyl-β-D-fructopyranose 
• 138528-01-5 3,4,5-tri-O-benzyl-1,2-O-isopropylidene-β-D-fructopyranose 

Relevant articles and documents

NOVEL METHODS OF ISOMERIZING CARBOHYDRATES

The invention provides a method of isomerizing a sugar into fructose using a calcium salt and an organic base. In certain embodiments, the sugar is glucose and/or mannose.

NMR for direct determination of Km and Vmax of enzyme reactions based on the Lambert W function-analysis of progress curves

1H NMR spectroscopy was used to follow the cleavage of sucrose by invertase. The parameters of the enzyme's kinetics, Km and V max, were directly determined from progress curves at only one concentration of the substrate. For comparison with the classical Michaelis-Menten analysis, the reaction progress was also monitored at various initial concentrations of 3.5 to 41.8 mM. Using the Lambert W function the parameters Km and Vmax were fitted to obtain the experimental progress curve and resulted in Km = 28 mM and V max = 13 μM/s. The result is almost identical to an initial rate analysis that, however, costs much more time and experimental effort. The effect of product inhibition was also investigated. Furthermore, we analyzed a much more complex reaction, the conversion of farnesyl diphosphate into (+)-germacrene D by the enzyme germacrene D synthase, yielding Km = 379 μM and kcat = 0.04 s- 1. The reaction involves an amphiphilic substrate forming micelles and a water insoluble product; using proper controls, the conversion can well be analyzed by the progress curve approach using the Lambert W function.

Enzymatic production and complete nuclear magnetic resonance assignment of the sugar lactulose

The enzymatic transgalactosylation from lactose to fructose leading to the prebiotic disaccharide lactulose was investigated using the β-galactosidase from Aspergillus oryzae and the hyperthermostable β-glycosidase from Pyrococcus furiosus (CelB). The conditions for highest lactulose yields relative to the initial lactose concentration were established on a 1 mL scale. Dependent on the initial molar ratio of lactose to fructose, more or fewer oligosaccharides other than lactulose were generated. Bioconversions on a 30 mL scale in a stirred glass reactor were performed, and lactulose yields of 46 mmol/L (44% relative to lactose) for CelB and 30 mmol/L (30% relative to lactose) for A. oryzae β-galactosidase were achieved. Only 5% of other oligosaccharides were detectable. The corresponding productivities were 24 and 16 mmol/L/h, respectively. The molecular structure of lactulose was investigated in detail and confirmed after purification of the reaction solution by LC-MS and 1D and 2D NMR. Lactulose (4-O-β-D-galactopyranosyl-D-fructose) was unambiguously proved to be the major transglycosylation disaccharide.

The combined hydrolysis and hydrogenation of inulin catalyzed by bifunctional Ru/C

A one-pot process for hydrolysis and hydrogenation of inulin to D-mannitol and D-glucitol over a bifunctional Ru/C catalyst was developed. The hydrolysis is catalyzed by the carbon support, onto which acidity was introduced by pre-oxidation. The effect of different carbon treatments on the hydrolysis of inulin was studied. Oxidation with ammonium peroxydisulfate resulted in a carbon with the highest hydrolysis activity. On this carbon, long chain inulin is hydrolyzed faster than inulin rich in short chains. The application of high pressure (up to 100 bar) increased the hydrolysis rate substantially. The combined process was successfully conducted with a Ru-catalyst supported on this oxidized carbon.

Tannins and Related Compounds. XXIII. Rhubarb (4): Isolation and Structures of New Classes of Gallotannins

A chemical examination of hydrolyzable tannins in a rhubarb of high quality (commercial name: ) has revealed the occurrence of four new acylated sugars, i.e., 2-O-cinnamoyl-β-D-glucose (I), 2-O-cinnamoyl-1-6-di-O-galloyl-β-D-glucose (II), 2-O-p-coumaroyl-1-O-galloyl-β-D-glucose (III) and 1-O-galloylfructose (IV), as well as the known compounds 2-O-cinnamoyl-1-O-galloyl-β-D-glucose (VII), (-)-epicatechin 3-O-gallate (VIII), 1-O-galloyl-β-D-glucose (IX) and 1,6-di-O-galloyl-β-D-glucose (X).A low-quality rhubarb (commercial name: ) was found to contain three new gallates, 1-O-galloylfructose (IV), 2,6-di-O-galloylglucose (V) and 3,5-dihydroxyphenol 1-O-β-D-(6-O-galloyl)-glucopyranoside (VI), together with five known compounds, VIII, X, 6-O-galloylglucose (XI), 1,2,6-tri-O-galloyl-β-D-glucose (XII) and procyanidin B-1 3-O-gallate (XIII).Keywords - rhubarb; Polygonaceae; gallotannin; cinnamoylglucose; p-coumaroylglucose; galloylfructose; phloroglucinol glucoside gallate; galloylglucose.