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. Pyrazines, including 2,5-deoxyfructosazine, can be produced either by pyrolytic decomposition of natural compounds or by the reaction of sugars with alcoholic ammonia. 2,5-Deoxyfructosazine is also formed by the breakdown of D-glucosamine at neutral pH. Like glucosamine, 2,5-deoxyfructosazine has DNA strand breakage activity and strongly inhibits IL-2 production by Jurkat cells stimulated with phytohemagglutinin (IC50 = ~1.25 mM).

Chemical Properties

Tan Solid

Uses

Contained in tobacco flavor additives.

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

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.

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.