| Identification | Back Directory | [Name]
deoxyfructosazine | [CAS]
17460-13-8 | [Synonyms]
NSC 270912
deoxyfructosazine
2,5-Deoxyfructosazine
Glucosamine Impurity C
Glucosamine EP Impurity C
Glucosamine sulfate Impurity 12
Glucosamine sulphate Impurity C
Glucosamine sulfate EP impurity C
2,5-Deoxyfructosazine (hydrochloride)
Glucosamine EP Impurity C (Deoxy-Fructosazine)
(1R,2S,3R)-1-(5-((2S,3R)-2,3,4-trihydroxybutyl)
Glucosamine EP Impurity C (2,5-Deoxyfructosazine)
2-(D-arabino-Tetrahydroxybutyl)-5-(D-erythro-2,3,4-trihydroxybutyl)pyrazine
Glucosamine Hydrochloride Impurity 3(Glucosamine Hydrochloride EP Impurity C)
(1R,2S,3R)-1-[5-[(2S,3R)-2,3,4-Trihydroxybutyl]pyrazin-2-yl]-1,2,3,4-butanetetrol
(1R,2S,3R)-1-[5-[(2S,3R)-2,3,4-Trihydroxybutyl]-2-pyrazinyl]-1,2,3,4-butanetetrol
(1R,2S,3R)-1-(5-((2S,3R)-2,3,4-Trihydroxybutyl)pyrazin-2-yl)butane-1,2,3,4-tetraol
2-[(1R,2S,3R)-1,2,3,4-Tetrahydroxybutyl]-5-[(2S,3R)-2,3,4-trihydroxybutyl]pyrazine
1,2,3,4-Butanetetrol, 1-[5-[(2S,3R)-2,3,4-trihydroxybutyl]-2-pyrazinyl]-, (1R,2S,3R)-
(1R,2S,3R)-1-[5-[(2S,3R)-2,3,4-trihydroxybutyl]pyrazin-2-yl]butane-1,2,3,4-tetrol (deoxyfructosazine) | [Molecular Formula]
C12H20N2O7 | [MDL Number]
MFCD18382251 | [MOL File]
17460-13-8.mol | [Molecular Weight]
304.3 |
| Chemical Properties | Back Directory | [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 | [Major Application]
pharmaceutical small molecule | [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 |
| Hazard Information | Back Directory | [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. | [Synthesis]
Step 1: 5g fructose and 15g ammonium chloride were weighed and dissolved in 500g distilled water and stirred to make the mixture homogeneous. Step 2: Place the prepared aqueous solution of fructose and additional nitrogen source in a reaction vessel, s | [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 |
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