13185-73-4

Basic information

• Product Name: Fructosazine
• Synonyms: D-Arabino-1,1'-(2,5-pyrazinediyl)di-1,2,3,4-butanetetrol;(1R,1'R,2S,2'S,3R,3'R)-1,1'-(2,5-Pyrazinediyl)bis-1,2,3,4-butanetetrol;Fructosazine;1,1'-(Pyrazine-2,5-diyl)bis[(1R,2S,3R)-1,2,3,4-butanetetrol];1,1'-(Pyrazine-2,5-diyl)bis[(1R,2S,3R)-butane-1,2,3,4-tetraol];1,2,3,4-Butanetetrol, 1,1'-(2,5-pyrazinediyl)bis-, [1R-(1R*,1'*,2S*,2'S*,3R,3R*)];Aids123119;Aids-123119
• CAS NO: 13185-73-4
• Molecular Formula: C₁₂H₂₀N₂O₈
• Molecular Weight: 320.3
• Product Categories: Carbohydrates & Derivatives;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 13185-73-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: >150°C (dec.)
• Boiling Point: 764.9°Cat760mmHg
• Flash Point: 416.4°C
• Appearance: /
• Density: 1.68g/cm³
• Vapor Pressure: 1.34E-24mmHg at 25°C
• Refractive Index: 1.681
• Storage Temp.: -20?C Freezer
• Solubility: Methanol (Slightly, Heated), Water (Slightly, Heated, Sonicated)
• PKA: 11.54±0.20(Predicted)
• CAS DataBase Reference: Fructosazine(CAS DataBase Reference)
• NIST Chemistry Reference: Fructosazine(13185-73-4)
• EPA Substance Registry System: Fructosazine(13185-73-4)

Safety Data

• Hazardous Substances Data: 13185-73-4(Hazardous Substances Data)

Usage

Chemical Properties

Brown Solid

Uses

Fructosazine is used in the treatment of osteoarthritis and rheumatoid arthritis.

InChI:InChI=1/C12H20N2O8/c15-3-7(17)11(21)9(19)5-1-13-6(2-14-5)10(20)12(22)8(18)4-16/h1-2,7-12,15-22H,3-4H2/t7-,8-,9-,10-,11-,12-/m1/s1

Upstream product

• 57-48-7 D-Fructose 
• 65039-08-9 3-ethyl-1-methyl-1H-imidazol-3-ium bromide 
• 143314-17-4 1-ethyl-3-methylimidazolium acetate 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 9012-76-4 chitosan 
• 1398-61-4 chitin 
• 250358-46-4 1-ethyl-3-methylimidazolium hydroxide 
• 748136-10-9 1-hexyl-3-methylimidazolium hydroxide 
• 85100-77-2 1-n-butyl-3-methylimidazolim bromide 
• 66-84-2 D-(+)-glucosamine hydrochloride 
• 56-87-1 L-lysine 
• 3416-24-8 2-amino-2-deoxyglucose 

Downstream Products

• 4429-04-3 1-amino-1-deoxy-D-fructose 

Relevant articles and documents

Reduction mechanism of tetrazolium salt XTT by a glucosamine derivative

XTT (3′-{1-[(phenylamino)-carbonyl]-3,4-tetrazolium}-bis(methoxy-6- nitro)benzenesulfonic acid hydrate) was reduced by incubated glucosamine hydrochloride. The XTT reducibility by incubated glucosamine was linearly related with the DNA-breaking activity. In order to elucidate the reaction mechanism, the glucosamine derivatives formed during the incubation process were separated by HPLC, and the compound responsible for the reduction was analyzed. Among the incubated products, fructosazine and deoxyfructosazine were identified by LC-MS, FAB-MS, and 1H- and 13C-NMR. These products showed no XTT reducibility, but an unstable intermediate with a molecular weight of 322 displayed reducibility. Since the intermediate gave fructosazine by oxidation with XTT and was a precursor of deoxyfructosazine, we conclude that the intermediate could have been dihydrofructosazine. Therefore, the XTT reducibility by incubated glucosamine was based on dihydrofructosazine formed by the condensation of two molecules of glucosamine.

Formation of pyrazine derivatives from D-glucosamine and their deoxyribonucleic acid (DNA) strand breakage activity

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Preparation method and application of fructosazine

The invention discloses a preparation method and application of fructozine, and the preparation method of the fructozine comprises the steps of synthesis of 1-dibenzylamino -1-deoxidized- D-fructose, preparation of 1-dibenzylamino- 1-deoxidized -4, 5-oxo- isopropylidene- D-fructose, preparation of isopropylidene protected fructozine and synthesis of the fructozine. According to the preparation method of the fructosazine, Pd/C is used for catalyzing amino sugar to be oxidized to form pyrazine rings for the first time. According to the reaction route, raw materials are economical and easy to obtain, reaction conditions are mild, high temperature and high pressure are avoided, the product is single and high in purity, and a complex post-treatment process is avoided. In addition, the invention provides application of the fructosazine in preparation of anti-aging cosmetics.

Method for preparing fructosazine by utilizing chitin-based biomass

The invention relates to a method for preparing fructosazine by utilizing chitin-based biomass. The method comprises the following steps: adding a dry chitin-based biomass raw material, an imidazolium ionic liquid solution and an additive to dimethyl sulfoxide to obtain a mixture; uniformly mixing the obtained mixture to perform a reaction, wherein the mass ratio of the imidazolium ionic liquid to the chitin-based biomass raw material is 1: (2-100), and the mass ratio of the added chitin-based biomass raw material to an oxidant is 1: (1-50) to obtain an intermediate product; adding a crystallization solvent to the intermediate product, wherein the volume ratio of the intermediate product to the solvent is 1: 1 to 1: 10; completely dissolving the product; removing undissolved impurities to obtain a filter liquor; carrying out rotary evaporation concentration on the filter liquor; standing; and recrystallizing to prepare the final product. The method has the advantages of wide raw material resources, no pollution, simple preparation and high product purity.