deoxyfructosazine Chemical Properties

Melting point:

157-160°C

Boiling point:

712.0±60.0 °C(Predicted)

Density 

1.582

storage temp. 

Refrigerator

solubility 

DMSO (Slightly), Methanol (Slightly, Heated), Water (Slightly, Sonicated)

form 

Solid

pka

11.86±0.20(Predicted)

color 

Pale Brown to Brown

InChI

InChI=1S/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/t8-,9+,10+,11+,12+/m0/s1

InChIKey

FBDICDJCXVZLIP-VSSNEEPJSA-N

SMILES

[C@H](C1=NC=C(C[C@H](O)[C@H](O)CO)N=C1)(O)[C@H](O)[C@H](O)CO

Safety Information

Safety Statements 

24/25

HS Code 

29072990

deoxyfructosazine Usage And Synthesis

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.

References

[1] NATHALY HENRY. Synthesis of water-compatible imprinted polymers of in situ produced fructosazine and 2,5-deoxyfructosazine.[J]. Talanta, 2012, 99: 816-823. DOI: 10.1016/j.talanta.2012.07.035
[2] RODGMAN A, PERFETTI T. The Chemical Components of Tobacco and Tobacco Smoke[C]. 2008: 0. DOI: 10.1201/b13973
[3] AIPING ZHU . 2,5-Deoxyfructosazine, a d-glucosamine derivative, inhibits T-cell interleukin-2 production better than d-glucosamine[J]. Carbohydrate Research, 2007, 342 18: Pages 2745-2749. DOI: 10.1016/j.carres.2007.08.025
[4] TOMOKO SHIMAMURA. Reduction mechanism of tetrazolium salt XTT by a glucosamine derivative.[J]. Bioscience, Biotechnology, and Biochemistry, 2003, 67 2: 295-299. DOI: 10.1271/bbb.67.295
[5] K SUMOTO. Formation of pyrazine derivatives from D-glucosamine and their deoxyribonucleic acid (DNA) strand breakage activity.[J]. Chemical & pharmaceutical bulletin, 1991, 39 3: 792-794. DOI: 10.1248/cpb.39.792

deoxyfructosazine(17460-13-8)Related Product Information

• UDP-3-O[R-3-Hydroxymyristoyl]-N-Acetylglucosamine Tris Salt
• Fructosazine
• UDP-3-O-(3-hydroxymyristoyl)-N-acetylglucosamine
• polyfructan(inulin type)
• beta-D-Fructopyranose