17460-13-8

Basic information

• Product Name: deoxyfructosazine
• Synonyms: deoxyfructosazine;(1R,2S,3R)-1-[5-[(2S,3R)-2,3,4-Trihydroxybutyl]pyrazin-2-yl]-1,2,3,4-butanetetrol;2-[(1R,2S,3R)-1,2,3,4-Tetrahydroxybutyl]-5-[(2S,3R)-2,3,4-trihydroxybutyl]pyrazine;2,5-Deoxyfructosazine;(1R,2S,3R)-1-[5-[(2S,3R)-2,3,4-Trihydroxybutyl]-2-pyrazinyl]-1,2,3,4-butanetetrol;2-(D-arabino-Tetrahydroxybutyl)-5-(D-erythro-2,3,4-trihydroxybutyl)pyrazine;NSC 270912;2,5-Deoxyfructosazine (hydrochloride)
• CAS NO: 17460-13-8
• Molecular Formula: C₁₂H₂₀N₂O₇
• Molecular Weight: 304.3
• Product Categories: Aromatics;Carbohydrates & Derivatives;Heterocycles;Aromatics, Carbohydrates & Derivatives, Heterocycles
• Mol File: 17460-13-8.mol

Chemical Properties

• Melting Point: 157-160°C
• Boiling Point: 712°Cat760mmHg
• Flash Point: 384.4°C
• Appearance: /
• Density: 1.582
• Vapor Pressure: 2.8E-21mmHg at 25°C
• Refractive Index: 1.655
• Storage Temp.: Refrigerator
• Solubility: DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly, Sonicated)
• PKA: 11.86±0.20(Predicted)
• CAS DataBase Reference: deoxyfructosazine(CAS DataBase Reference)
• NIST Chemistry Reference: deoxyfructosazine(17460-13-8)
• EPA Substance Registry System: deoxyfructosazine(17460-13-8)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 17460-13-8(Hazardous Substances Data)

Usage

Uses

Used in Food and Tobacco Industry:
2,5-Deoxyfructosazine is used as a flavoring agent for its characteristic taste and aroma, enhancing the sensory experience of food and tobacco products.
Used in Chemical Research:
2,5-Deoxyfructosazine is used as a subject of study in chemical research due to its DNA strand breakage activity and its ability to inhibit IL-2 production by Jurkat cells stimulated with phytohemagglutinin. This makes it a potential candidate for further investigation into its biological properties and possible applications in various fields.

InChI:InChI=1/C12H20N2O7/c15-4-9(18)8(17)1-6-2-14-7(3-13-6)11(20)12(21)10(19)5-16/h2-3,8-12,15-21H,1,4-5H2

Upstream product

• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 90-76-6 2-deoxy-2-amino glucose 
• 50-99-7 D-glucose 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 5505-63-5 D-mannosamine hydrochloride 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 7660-25-5 D-fructose 
• 57-48-7 D-Fructose 

Downstream Products

• 107281-04-9 D-erythro-3-deoxy-[2]hexosulose-bis-(4-nitro-phenylhydrazone) 
• 4429-04-3 1-amino-1-deoxy-D-fructose 

Relevant articles and documents

A clean conversion of D-glucosamine hydrochloride to a pyrazine in the presence of phenylboronate or borate

D-Glucosamine was found to undergo a condensation to give 2-(arabo-tetrahydroxybutyl)-5-(erythro-2,3,4-trihydroxy-butyl)-pyrazine (2) as practically the sole product in the presence of phenylboronate or borate. The reaction proceeds in aqueous solutions a

Glucosamine condensation catalyzed by 1-ethyl-3-methylimidazolium acetate: Mechanistic insight from NMR spectroscopy

The basic ionic liquid 1-ethyl-3-methylimidazolium acetate ([C2C1Im][OAc]) could efficiently catalyze the conversion of 2-amino-2-deoxy-D-glucose (GlcNH2) into deoxyfructosazine (DOF) and fructosazine (FZ). Mechanistic investigation by NMR studies disclosed that [C2C1Im][OAc], exhibiting strong hydrogen bonding basicity, could coordinate with the hydroxyl and amino groups of GlcNH2via the promotion of hydrogen bonding in bifunctional activation of substrates and further catalyzing product formation, based on which a plausible reaction pathway involved in this homogeneous base-catalyzed reaction was proposed. Hydrogen bonding as an activation force, therefore, is responsible for the remarkable selectivity and rate enhancement observed.

Study on the accelerated Gutknecht self-cyclocondensation of amino-sugars under atmospheric pressure chemical ionization conditions

An unexpected gas phase Gutknecht self-condensation of d-glucosamine hydrochloride to 2,5-deoxyfructosazine (2,5-DOF) in atmospheric pressure chemical ionization mass spectrometry (APCI-MS) was described. Mechanistic studies indicated that the thermospray conditions in APCI largely accelerate the irreversible Gutknecht self-cyclocondensation reaction of amino-sugars. Our observations provide a promising clue for a new borate-free synthetic method of 2,5-DOF by mimicking the APCI conditions.

The role of the anion in the reaction of reducing sugars with ammonium salts

Reactions of reducing sugars with ammonia and its compounds are important commercially, particularly in the preparation of flavors and caramel colors. However, such reactions generally produce a complex series of products ranging from simple molecules to complex polymeric materials, particularly since commercial systems generally involve mixtures of sugars as opposed to single sugars. This complexity has made understanding the mechanisms of such reactions difficult. Therefore, investigatory work has generally been focused on model systems. Herein we report one such study with model systems: the effects of the nature of the anion of the reactions of reducing sugars with ammonium salts. D-Glucose was reacted in aqueous solution with each of the following ammonium salts: acetate, bicarbonate, carbonate, chloride, citrate, formate, monohydrogenphosphate (DAP), sulfate, and sulfite. These reactions were carried out in a Parr bomb at 93°C for 2.5 h. The initial pH of the reaction mixtures was adjusted to pH 8.0 at 25°C. The resulting mixtures were analyzed by LC-MS, and the results were analyzed by comparing the product yields and distributions with those obtained with DAP. The major reaction product of interest was 2,6-deoxyfructosazine, as it had been shown to be a marker for the polymeric material formed from such reactions. It was found that ammonium salts of weak acids were much more effective in effecting the desired reactions than were those of strong acids; however, none was as effective as DAP.

Valorization of monosaccharides towards fructopyrazines in a new sustainable and efficient eutectic medium

In this paper, we propose a new approach for valorization of monosaccharides derived from biomass into value added chemicals in a green and economically efficient manner by forming eutectic medium exclusively between reactants. Eutectic mixtures are emerging as an advantageous alternative to ionic liquids and have already found broad applications in biomass treatment; however they are preferably used only as low vapor pressure solvents. Increasing interest in eutectic solvents originates from their flexibility to adjust their properties to different biorefinery needs by simple variation of the compositions of eutectic mixtures. In this work, we made a first attempt to use a low molecular weight component, ammonium formate, to significantly change the physical properties of the eutectic mixtures and simultaneously increase their chemical reactivity. Using this approach, we valorised simple monosaccharides by turning them into fructopyrazines with high yields in their eutectic mixtures with ammonium formate. The research revealed a high sensitivity of the product yields to the temperature of the reaction and composition of the eutectic medium, as well as an important role of formate anions in product stabilization.

Method for preparing 2,5-deoxyfructosazine by utilizing fructose

The invention belongs to the field of green chemical industry, and particularly relates to a method for preparing high value-added nitrogen-containing heterocyclic compound 2,5-deoxyfructosazine by utilizing fructose. The method overcomes the problems of long reaction time, a low yield, poor target product selectivity and higher costs in a reaction of preparing 2,5-deoxyfructosazine. The method comprises the following steps: using the reducing sugar fructose as a raw material, dissolving the fructose and an additional nitrogen source into distilled water, placing the mixed solution into a reaction vessel, and performing a hydrothermal reaction to form a mixed liquid containing a crude product containing the 2,5-deoxyfructosazine; and performing rotary evaporation concentration on the mixedliquid, dissolving the concentrated liquid into a crystallization solvent, performing filtration to remove insoluble impurities, allowing the filtrate to stand, and performing crystallization to obtain the product 2,5-deoxyfructosazine. The method provided by the invention has the advantages of a low raw material price, a simple process, no pollution in the process, and high purity and good yieldof the obtained product.

Method for preparing deoxyfructosazine through chitin biomass

A method for preparing deoxyfructosazine through chitin biomass comprises the following steps: uniformly mixing a dry chitin biomass raw material, an imidazole ionic liquid solution and an additive in a dimethyl sulfoxide reaction medium for reaction to obtain an intermediate product; adding a crystal solvent in the intermediate product to completely dissolve the product, performing hot filtration to remove insoluble impurities, performing rotary evaporation concentration on a filtrate, and performing recrystallization to obtain the product, namely the deoxyfructosazine. The method has the advantages that the raw material source is wide, pollution is avoided, the preparation is simple, and the product purity is high.

Efficient one-pot synthesis of deoxyfructosazine and fructosazine from d-glucosamine hydrochloride using a basic ionic liquid as a dual solvent-catalyst

An efficient one-pot dehydration process for convert d-glucosamine hydrochloride (GlcNH2) into 2-(d-arabino-1′,2′,3′,4′-tetrahydroxybutyl)-5-(d-erythro-2′′,3′′,4′′-trihydroxybutyl)pyrazine (deoxyfructosazine, DOF) and 2,5-bis-(d-arabino-1,2,3,4-tetrahydroxybutyl)pyrazine (fructosazine, FZ) was reported. A task-specific basic ionic liquid, 1-butyl-3-methylimidazolium hydroxide ([BMIM]OH), was employed as an environmentally-friendly solvent and catalyst. The products were qualitatively and quantitatively characterized by MALDI-TOF-MS, 1H NMR and 13C NMR spectroscopy. The influences of GlcNH2 concentrations, reaction temperature, reaction time, additives and co-solvents on the yields of products were studied. The maximum yield of 49% was obtained in the presence of [BMIM]OH and DMSO under optimized conditions (120 °C, 180 min). In addition, a plausible mechanism was proposed. Our project was to develop efficient, atom economical and eco-compatible routes for the synthesis of heterocyclic compounds from marine biomass (or nitrogen-containing biomass). The obtained aromatic heterocyclic compounds showed potential pharmacological action and physiological effects, and they also could be utilized as flavoring agents in the food industry. This journal is

Reduction mechanism of tetrazolium salt XTT by a glucosamine derivative

XTT (3′-{1-[(phenylamino)-carbonyl]-3,4-tetrazolium}-bis(methoxy-6- nitro)benzenesulfonic acid hydrate) was reduced by incubated glucosamine hydrochloride. The XTT reducibility by incubated glucosamine was linearly related with the DNA-breaking activity. In order to elucidate the reaction mechanism, the glucosamine derivatives formed during the incubation process were separated by HPLC, and the compound responsible for the reduction was analyzed. Among the incubated products, fructosazine and deoxyfructosazine were identified by LC-MS, FAB-MS, and 1H- and 13C-NMR. These products showed no XTT reducibility, but an unstable intermediate with a molecular weight of 322 displayed reducibility. Since the intermediate gave fructosazine by oxidation with XTT and was a precursor of deoxyfructosazine, we conclude that the intermediate could have been dihydrofructosazine. Therefore, the XTT reducibility by incubated glucosamine was based on dihydrofructosazine formed by the condensation of two molecules of glucosamine.