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Preparation method and application of fructosazine

A technology of fructosine and fructose, applied in the field of chemical preparations, can solve the problems of high cost, long reaction time, difficult preparation of catalysts and the like

Active Publication Date: 2021-04-20
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, the existing reactions have the problem of requiring longer reaction time or higher reaction temperature, and under most conditions, FZ cannot be selectively generated.
The reaction product is greatly affected by the reaction conditions, especially the reaction solvent, the pH value of the reaction mixture and the reaction temperature; and the new catalyst is difficult to prepare or expensive, not economical and easy to obtain
In addition, both FZ and DOF are water-soluble substances, so it is difficult to separate and purify

Method used

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  • Preparation method and application of fructosazine
  • Preparation method and application of fructosazine
  • Preparation method and application of fructosazine

Examples

Experimental program
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Effect test

Embodiment 1

[0038] Embodiment 1: the synthesis of fructozine

[0039] figure 1 For the synthetic route diagram of the preparation method of the fructozine provided in the examples of the present invention, see figure 1 .

[0040] In this embodiment, the synthesis of fructozine comprises the following steps:

[0041] Synthesis of Step 1, 1-dibenzylamino-1-deoxy-D-fructose [20]

[0042] Weigh 3.6g of D-glucose (compound I) (D-glucose, 20mmol) into a three-necked flask, add 40mL of absolute ethanol, stir at room temperature, add 3.96g of dibenzylamine, 1mL of glacial acetic acid in turn, stir evenly, and Reflux at 80°C for 3 hours, cool to room temperature, vacuum filter, wash the filter cake with absolute ethanol 3×10mL and filter with suction to obtain (3S, 4R, 5R)-2-((dibenzylamino)methyl) tetra Hydrogen-2H-pyran-2,3,4,5-tetrol 5.9g, namely 1-dibenzylamino-1-deoxy-D-fructose (compound II), yield 82%. 1 H NMR (400 MHz, DMSO-d6) δ7.30 (m, 10H, Ph-H), 5.25 (s, 1H, OH), 4.43 (d, J=4.7...

Embodiment 2

[0054] Embodiment 2: Anti-aging activity evaluation of fructozine

[0055] 1. Experimental method

[0056] 1. Cell culture

[0057] The 2BS cell line isolated from human fetal lung fibroblasts was originally established by the China Institute of Biological Products and has been widely used as a model of cellular senescence. It is generally believed that PD (population doubling, population doubling times, also known as "generations") below 30 are young cells, while replicative senescent cells are PD55 or above. The cells in this experiment were purchased from the China Type Culture Collection Center of Wuhan University. The cells were grown in MEM supplemented with 10% fetal bovine serum, 1% penicillin and streptomycin double antibody solution, and placed at 37°C, 5% CO 2 in the incubator. When the cells grew to 85%, the cultured cells were split and passaged at a ratio of 1:2 or 1:4. Cumulative cell doublings (CPDs) were calculated as log 2 (D / D 0 ), where D and D 0 are...

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Abstract

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.

Description

technical field [0001] The invention belongs to the field of chemical preparations, and in particular relates to a preparation method and application of fructozine. Background technique [0002] Fructosezine (FZ) and deoxyfructozine (DOF) are a class of pyrazines that were discovered, isolated and characterized in baked foods. These compounds are used as flavoring agents in the food industry because of their unique and attractive smell; they are used to increase or change the taste of tobacco smoke because of their low odor threshold. In terms of pharmacological and physiological activities, both have antibacterial activity, and FZ plays an important role as a heat-resistant antibacterial agent; both also have inhibitory activity against interleukins (1β and 2), which may contribute to Prevent pathological cartilage degradation and other inflammatory diseases; and, recent studies have shown that FZ has α-glucosidase inhibitory activity, and FZ and DOF are transported by hex...

Claims

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Application Information

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IPC IPC(8): C07D241/12A61P39/06A61K8/49A61Q19/08
Inventor 李悦青姜丁宁赵伟杰王世盛郭修晗李广哲
Owner DALIAN UNIV OF TECH
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