17460-13-8

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).

Tan Solid

Contained in tobacco flavor additives.

[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