6347-01-9

Basic information

• Product Name: D-(-)-FRUCTOSE
• Synonyms: D-FRUCTOPYRANOSE;(3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
• CAS NO: 6347-01-9
• Molecular Formula: C₆H₁₂O₆
• Molecular Weight: 180.16
• Mol File: 6347-01-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 91.5-93.5 °C
• Boiling Point: 401.1°Cat760mmHg
• Flash Point: 196.4°C
• Appearance: /
• Density: 1.758g/cm³
• Vapor Pressure: 4.23E-08mmHg at 25°C
• Refractive Index: 1.645
• PKA: 11.52±0.70(Predicted)
• CAS DataBase Reference: D-(-)-FRUCTOSE(CAS DataBase Reference)
• NIST Chemistry Reference: D-(-)-FRUCTOSE(6347-01-9)
• EPA Substance Registry System: D-(-)-FRUCTOSE(6347-01-9)

Safety Data

• Hazardous Substances Data: 6347-01-9(Hazardous Substances Data)

Usage

General Description

D-(-)-Fructose is a monosaccharide sugar commonly found in fruits, honey, and root vegetables. It is a sweet-tasting compound that is often used as a sweetener in various food and beverage products. D-(-)-Fructose is a key source of energy for the body and is readily absorbed into the bloodstream, making it a popular ingredient in sports drinks and energy bars. Its chemical structure consists of a six-carbon ring with five hydroxyl groups and a carbonyl group, and it is often used as a sugar substitute for individuals with diabetes. D-(-)-Fructose is metabolized in the liver and has been associated with certain health concerns when consumed in excess, such as obesity, fatty liver disease, and insulin resistance. However, when consumed in moderation as part of a balanced diet, D-(-)-Fructose can be a natural and enjoyable source of sweetness.

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

Upstream product

• 2280-44-6 D-Glucose 
• 57-50-1 Sucrose 
• 492-61-5 β-D-glucose 

Downstream Products

• 15219-29-1 benzyl β-D-fructopyranoside 
• 78008-09-0 n-butyl β-D-fructopyranoside 
• 80971-59-1 α-D-fructofuranose 2-butyl ether 
• 7143-89-7 1,3,4,5-tetra-O-benzoyl-β-D-fructopyranoside 
• 83032-14-8 1,3,4,5,6-Penta-O-benzoyl-keto-D-fructose 
• 80763-56-0 1,3,4,6-tetra-O-benzoyl-α-D-fructofuranose 
• 85973-56-4 1,3,4,5-tetra-O-benzoyl-b-D-fructopyranosyl-2-O-benzoylate 
• 69-65-8 mannitol 
• 50-70-4 D-sorbitol 
• 530-26-7 D-Mannose 
• 488-82-4 D-Arabitol 
• 96-26-4 dihydroxyacetone 
• 56-81-5 glycerol 
• 1198-69-2 D-glucono-1,4-lactone 

Relevant articles and documents

A hydrothermally stable ytterbium metal-organic framework as a bifunctional solid-acid catalyst for glucose conversion

Yb6(BDC)7(OH)4(H2O)4 contains both bridging hydroxyls and metal-coordinated waters, possessing Br?nsted and Lewis acid sites. The material crystallises from water at 200 °C. Using the solid as a heterogenous catalyst, glucose is converted into 5-hydroxymethylfurfural, via fructose, with a total selectivity of ～70percent after 24 hours at 140 °C in water alone: the material is recyclable with no loss of crystallinity.

Substrate-dependent chemoselective aldose-aldose and aldose-ketose isomerizations of carbohydrates promoted by a combination of calcium ion and monoamines

Epimerization of aldoses at C-2 has been extensively investigated by using various metal ions in conjunction with diamines, monoamines, and aminoalcohols. Aldoses are epimerized at C-2 by a combination of alkaline-earth or rare-earth metal ions (Ca2+, Sr2+, Pr3+, or Ce3+) and such monoamines as triethylamine. In particular, the Ca2+ -triethylamine system proved effective in promoting aldose-ketose isomerization as well as C-2 epimerization of aldoses. 13C NMR studies using D-(1-13C)glucose and D-(1-13C)galactose with the CaCl2 system in CD3OD revealed that the C-2 epimerization proceeds via stereospecific rearrangement of the carbon skeleton, or 1,2-carbon shift, and ketose formation proceeds partially through an intramolecular hydrogen migration or 1,2-hydride shift and, in part, via an enediol intermediate. These simultaneous aldose-aldose and aldose-ketose isomerizations showed interesting substrate-dependent chemoselectivity. Whereas the mannose-type aldoses having 2,3-erythro configuration (D-mannose, D-lyxose, and D-ribose) showed considerable resistance to both the C-2 epimerization and the aldose-ketose isomerization, the glucose-type sugars having 2,3-threo and 3,4-threo configurations, D-glucose and D-xylose, are mainly epimerized at C-2 and those having the 2,3-threo and 3,4-erythro configurations, D-galactose and D-arabinose, were mostly isomerized into 2-ketoses. These features are of potential interest in relevance to biomimic sugar transformations by metal ions.

Rare keto-aldoses from enzymatic oxidation: Substrates and oxidation products of pyranose 2-oxidase

Pyranose oxidases are known to oxidise D-glucose, D-xylose and L- sorbose to keto-aldoses, biochemically interesting compounds that may also be used for synthetic purposes in a variety of reactions. In this study pyranose oxidase from the basidiomycete Peniophora gigantea was investigated, and it was found that this enzyme is able to oxidise a broad variety of substrates very effectively. In analogy to its natural mode of action, most substrates are oxidised regioselectively in position 2. Certain compounds, however, are converted into 3-keto derivatives, and the enzyme even exhibits transfer potential, that is, disscharides are formed from β-glycosides of higher alcohols. Substrates that may be oxidised at C-2 in yields between 40-98% are D-allose, D-galactose, 6-deoxy-D-glucose, D-gentiobiose, α-D-glucopyranosyl fluoride and the very interesting 3-deoxy-D-glucose. 1,5-Anhydro-D-glucitol (1-deoxy-D-glucose) is very effectively oxidised in position 2 in 98% yield and additionally gives a product of dioxidation at C-2 and C-3 upon prolonged reaction time Selective oxidation at C-3 was found for 2-deoxy-D-glucose in very good yields and for methyl β-D-gluco- and methyl β-galactopyranoside in lower yields. All oxidation products were unequivocally characterised by NMR spectroscopy and/or chemical derivatisation. In addition, the kinetic data of the enzymatic reactions were determined for all substrates. On the basis of these data and the structural characteristics of the substrates, a model for the minimal structural requirements of the enzyme-substrate interaction is suggested. The enzyme presumably uses two different binding modes for the regioselective C-2 and the C-3 oxidations, which are described.