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
• Article Data: 10

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

Description

2,5-Deoxyfructosazine is a pyrazine derivative that can be found in cured tobacco and is used as a flavoring agent in the food and tobacco industry. It is formed by the breakdown of D-glucosamine at neutral pH and possesses DNA strand breakage activity and strong inhibition of IL-2 production by Jurkat cells stimulated with phytohemagglutinin. It is a tan solid.

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

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

Downstream Products

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

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

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.