75414-43-6

Basic information

• Product Name: 1 5-ANHYDRO-D-FRUCTOSE
• Synonyms: 1 5-ANHYDRO-D-FRUCTOSE;1,5-anhydrofructose;2-Oxo-1,2-dideoxy-D-glucopyranose;5,6-Dihydro-4β,5α-dihydroxy-6β-(hydroxymethyl)-2H-pyran-3(4H)-one;AF Syrup
• CAS NO: 75414-43-6
• Molecular Formula: C₆H₁₀O₅
• Molecular Weight: 162.1406
• Mol File: 75414-43-6.mol

Chemical Properties

• Boiling Point: 405°Cat760mmHg
• Flash Point: 176.1°C
• Appearance: /
• Density: 1.521g/cm³
• Vapor Pressure: 3.02E-08mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Methanol (Slightly), Water (Sparingly)
• Stability: Hygroscopic
• CAS DataBase Reference: 1 5-ANHYDRO-D-FRUCTOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1 5-ANHYDRO-D-FRUCTOSE(75414-43-6)
• EPA Substance Registry System: 1 5-ANHYDRO-D-FRUCTOSE(75414-43-6)

Safety Data

• Hazardous Substances Data: 75414-43-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1,5-Anhydro-D-fructose is used as a pharmaceutical compound for its antioxidant, anti-inflammatory, and anti-cancer properties. Its potential to modulate various biological pathways and exhibit therapeutic effects makes it a promising candidate for the development of new drugs and treatments.
Used in Environmental Research:
1,5-Anhydro-D-fructose is used as a biomarker to study the environmental impact of biomass burning. Its presence in atmospheric aerosols allows researchers to monitor and assess the effects of biomass burning on air quality and climate change.
Used in Bioenergy Production:
1,5-Anhydro-D-fructose is used as a potential carbon source for the production of bioethanol. Its ability to be converted into biofuels makes it a valuable resource for sustainable energy production and reducing reliance on fossil fuels.

InChI:InChI=1/C6H10O5/c7-1-4-6(10)5(9)3(8)2-11-4/h4-7,9-10H,1-2H2/t4-,5-,6-/m1/s1

Upstream product

• 75414-31-2 oxime of 1,5-anhydro-D-fructose 
• 154-58-5 1,5-anhydro-D-glucitol 
• 1017968-94-3 1,5-anhydro-D-fructose E-oxime 
• 1017968-98-7 3,4,6-tri-O-benzyl-1,5-anhydro-D-fructose 
• 3366-47-0 2,3,4,6-tetra-O-acetyl-1,5-anhydro-D-arabinohex-1-enopyranose 
• 75414-32-3 1,5-anhydro-3,4,6-tri-O-benzoyl-D-fructose 
• 78574-35-3 2,3:4,5-di-O-isopropylidene-1-O-p-tolylsulfonyl-β-D-fructopyranose 
• 40614-91-3 2,3:4,5-di-O-isopropylidene-1-O-(trifluoromethanesulfonyl)-β-D-fructopyranose 
• 871507-89-0 2,3-O-isopropylidene-1-O-methylsulfonyl-β-D-fructopyranose 
• 943241-16-5 2,3-O-isopropylidene-1-O-p-tolylsulfonyl-β-D-fructopyranose 
• 871507-90-3 1,5-anhydro-2,3-O-isopropylidene-β-D-fructopyranose 
• 75414-37-8 1,5-anhydro-D-fructose diethyldithioacetal 
• 82569-81-1 1,5-anhydro-3,4,6-tri-O-benzoyl-D-fructose oxime 

Downstream Products

• 211800-60-1 3,6-di-O-acetyl-1,5-anhydro-4-deoxy-D-glycero-hex-3-enopyranos-2-ulose 
• 75414-38-9 (6S)-4-benzoyloxy-6-benzoyloxymethyl-2H-pyran-3(6H)-one 
• 252977-26-7 1,5-anhydro-6-O-dodecanoyl-D-fructose 
• 297687-34-4 1,5-anhydro-D-fructose O-benzyloxime 
• 252977-30-3 1,5-anhydro-6-O-octadecanoyl-D-fructose 
• 252977-28-9 1,5-anhydro-6-O-hexadecanoyl-D-fructose 

Relevant articles and documents

FUNGAL ENZYMIC ACTIVITY DEGRADING 1,4-α-D-GLUCANS TO 1,5-D-ANHYDROFRUCTOSE

1,5-D-Anhydrofructose, the precursor of the antibiotic pyrone microthecin in morels and other fungi, is produced in Morchella vulgaris by a novel enzymic activity, presumably a lyasic one, which acts specifically on openchain 1,4-α-D-glucans; it can be prepared enzymatically in vitro from starch in 40 to 50percent yield.Key Word Index - Morchella vulgaris; M. costata; fungi; morels; cortacerone; mircothecin; carbohydrates; pyrones; glucosone; 1,5-D-anhydrofructose; bioconversion; 1,4-α-D-glucan; starch; glycogen.

Purification, characterization, and molecular cloning of a pyranose oxidase from the fruit body of the basidiomycete, Tricholoma matsutake

A new H2O2-generating pyranose oxidase was purified as a strong antifungal protein from an arbuscular mycorrhizal fungus, Tricholoma matsutake. The protein showed a molecular mass of 250 kDa in gel filtration, and probably consisted of four identical 62 kDa subunits. The protein contained flavin moiety and it oxidized D-glucose at position C-2. H2O 2 and D-glucosone produced by the pyranose oxidase reaction showed antifungal activity, suggesting these compounds were the molecular basis of the antifungal property. The Vmax, Km, and kcat for D-glucose were calculated to be 26.6 U/mg protein, 1.28 mM, and 111/s, respectively. The enzyme was optimally active at pH 7.5 to 8.0 and at 50°C. The preferred substrate was D-glucose, but 1,5-anhydro-D-glucitol, L-sorbose, and D-xylose were also oxidized at a moderate level. The cDNA encodes a protein consisting of 564 amino acids, showing 35.1% identity to Coriolus versicolor pyranose oxidase. The recombinant protein was used for raising the antibody.

Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (-)-bissetone and (-)-palythazine

High-yielding protocols are described to convert d-glucose-via hydroxylaminolysis of its hydroxyglucal esters, followed by deoximination and β-elimination of acid-into dihydropyranone building blocks with a single stereogenic center. Their versatility as enantiopure six-carbon scaffolds is highlighted by excellent regio- and stereocontrol in a variety of addition reactions and by their straightforward use as building blocks for the concise syntheses of the soft-coral constituents bissetone and palythazine in enantiopure form, thereby proving their absolute configuration. Moreover, several procedures are detailed to convert hydroxyglucal esters into 1,5-anhydro-d-fructose, their parent sugar, the direct low-temperature de-O-acylation being the most suitable for preparative purposes, as long as its access via enzymatic degradation of starch is not implemented on an appreciable scale.

1,5-Anhydro-d-fructose from d-fructose

1,5-Anhydro-d-fructose was efficiently prepared from d-fructose via regiospecific 1,5-anhydro ring formation of 2,3-O-isopropylidene-1-O-methyl(tolyl)sulfonyl-d-fructopyranose and subsequent deprotection.

1,5 AND 1,4-ANHYDROKETOSES, METHODS FOR THE PREPARATION OF 1,5-AND 1,4-ANHYDROKETOSES, INTERMEDIATES, AND USES OF 1,5-AND 1,4-ANHYDROKETOSES

The present invention relates to 1,4- and 1,5-anhydro-D-ketoses (monosaccharides, oligosaccharides and various glycoconjugates), e.g. 1,5-anhydro-D-fructose. Moreover, the invention provides synthetic methods and novel intermediates and precursors suitable for their preparation. The methods include catalytic- and/or pyrolitic sulfenic acid elimination of corresponding ?-hydroxy sulfoxides, N-deprotection of N-substituted-aminoglycals, O-deprotection of carbohydrate enolethers and/or O-acyl-substituted carbohydrate enols, and regio- and stereoselective modification and subsequent chemical transformation of bicyclic and/or tricyclic 1,4- and 1,5-anhydro-glycoderivatives. Furthermore, the present invention provides novel applications of 1,4- and 1,5-anhydroketoses within pharmaceutical, food and cosmetic industries.

A CONVENIENT ACCESS TO 1,5-ANHYDROKETOSES

A convenient, verstile entry into the 1,5-anhydroketose series is described and their conversion into enolones, enolone oximes and γ-pyrones.