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| | deoxyfructosazine Basic information |
| Product Name: | deoxyfructosazine | | Synonyms: | (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;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) | | CAS: | 17460-13-8 | | MF: | C12H20N2O7 | | MW: | 304.3 | | EINECS: | | | Product Categories: | Aromatics, Carbohydrates & Derivatives, Heterocycles;Aromatics;Carbohydrates & Derivatives;Heterocycles | | Mol File: | 17460-13-8.mol |  |
| | 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 | | 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 |
| Safety Statements | 24/25 | | WGK Germany | WGK 3 | | HS Code | 29072990 | | Storage Class | 11 - Combustible Solids |
| | 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. | | 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, set the reaction temperature at 120C and the reaction time at 2 hours. At the end of the reaction, a small amount of the mixture of 2,5-deoxyfructosazine crude product was removed and analyzed. A conversion of fructose of 100% and a molar yield of 2,5-deoxyfructosazine of 60% were obtained. Step 3: The mixture of 2,5-deoxyfructosazine crude product was concentrated by spinning, 300 ml of ethanol and formic acid (v/v=1:6) was added, filtered, insoluble impurities were removed, and the filtrate was left to stand for 10 hours, and the product 2,5-deoxyfructosazine was obtained by crystallization, and the crystalline product was obtained with a purity ≥98%.
| | 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 Preparation Products And Raw materials |
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