6-amino-6-deoxyinulin as well as preparation and application thereof

A technology of deoxyinulin and amino group is applied in the field of daily chemicals, which can solve the problems of less renewable resources and the like, and achieve the effects of easy popularization, improved reactivity and simple synthesis steps.

Active Publication Date: 2011-05-18
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are very few reports on the utilization of this renewable resource

Method used

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  • 6-amino-6-deoxyinulin as well as preparation and application thereof
  • 6-amino-6-deoxyinulin as well as preparation and application thereof
  • 6-amino-6-deoxyinulin as well as preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 6-Amino-6-deoxyinulin is a compound represented by formula (1).

[0028] Formula 1)

[0029] (1) Take inulin for sulfonyl chloride esterification, specifically, dissolve 1.62 g of inulin and 1.90 g of p-toluenesulfonyl chloride into 30 mL of nitrogen-nitrogen dimethylformamide, and stir and react at -8°C for 10 h. After the reaction was finished, the reaction solution was poured into 150 mL of acetone, and a precipitate was precipitated. The precipitate was washed with acetone and tetrahydrofuran, then vacuum freeze-dried, and set aside.

[0030] The prepared product was p-tosylated inulin (3.2 g) dissolved in 20 mL of dimethyl sulfoxide and reacted with 1.3 g of sodium azide at 50° C. for 8 h. After the reaction was completed, the product was precipitated with 100 mL of acetone, washed with ether and acetone, respectively, and then vacuum-dried at -50°C to obtain 1.4 g of 6-azido-6-deoxyinulin, which was used for future use.

[0031] (2) Dissolve 1.4 g of the prod...

Embodiment 2

[0037] The difference from Example 1 is:

[0038] (1) Take inulin for halogenation reaction, and dry inulin and lithium bromide under vacuum at 100° C. overnight. Take 1.62g of inulin and 1g of lithium bromide and add them to 20mL of purified nitrogen-nitrogen dimethylformamide under the protection of nitrogen, raise the temperature until inulin and lithium bromide are completely dissolved, and add 3.5g of N- Bromosuccinimide (NBS) was added to the above reaction solution. Weigh 5.2 g of triphenylphosphine and dissolve it in 10 mL of nitrogen-nitrogen dimethylformamide. This solution was added dropwise to the reaction solution at room temperature. After the reaction solution was reacted at room temperature for 30 minutes, the temperature of the reaction system was raised to 70°C. After the reaction was carried out at 70°C for 3 hours, the reaction solution was poured into 150mL acetone, and a precipitate was precipitated. The precipitate was suction filtered, washed with ace...

Embodiment 3

[0042] The difference from Example 1 is that: 1.62g of inulin and 1.90g of p-toluenesulfonyl chloride were dissolved in 30mL of nitrogen-nitrogen dimethylformamide, and stirred and reacted at 5°C for 16 hours. After the reaction was finished, the reaction solution was poured into 150 mL of acetone, and a precipitate was precipitated. The precipitate was washed with acetone and tetrahydrofuran, and then vacuum freeze-dried to obtain 3.1 g of tosylated inulin.

[0043] The product obtained above was dissolved and then reacted with 1.0 g of sodium azide at 50° C. for 16 h. After the reaction, the product was precipitated with 100 mL of acetone, washed with ether and acetone, respectively, and vacuum-dried at -50°C to obtain 1.5 g of 6-azido-6-deoxyinulin, which was ready for use.

[0044] 1.5 g of the obtained 6-azido-6-deoxyinulin and 0.6 g of lithium aluminum hydride were dissolved in 20 mL of purified 1,4-dioxane, and reacted at 55° C. for 19 h under nitrogen protection. The...

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PUM

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Abstract

The invention relates to fields of daily chemicals and pharmaceuticals industry, in particular to 6-amino-6-deoxyinulin as well as preparation and application thereof. In the 6-amino-6-deoxyinulin shown as a formula (I), the average value range of n is 10-35. The preparation comprises the steps of undergoing a helogenation reaction of inulin or undergoing esterification of inulin and sulfonyl chloride, respectively undergoing a reaction of the product obtained through the helogenation reaction of the inulin or the esterification and sodium azide or azido lithium at a temperature of 40-70 DEG C for 8-24 hours to obtain 6-azido-6-deoxyinulin, and reducing the 6-azido-6-deoxyinulin by utilizing triphenylphosphine or lithium aluminium hydride to obtain the 6-amino-6-deoxyinulin. In the invention, the 6-amino-6-deoxyinulin is obtained through an effective synthetic means; an inulin six-position easily-leaving group is obtained through utilizing halogen to substitute the primary hydroxyl ofthe inulin or through the esterification of inulin and sulfonyl chloride; and the 6-amino-6-deoxyinulin with high substitution is obtained through azido nucleophilic substitution and reduction. The 6-amino-6-deoxyinulin synthesized by the preparation method provided by the invention is simple in the synthetic step and easy to popularize; and the required equipment and raw materials are easy to get. The formula (I) is shown in the specification.

Description

technical field [0001] The invention relates to the field of daily chemicals and the pharmaceutical industry, in particular to 6-amino-6-deoxyinulin and its preparation and application. Background technique [0002] Inulin, also known as inulin, is a biological polysaccharide. It is produced by connecting D-fructofuranose molecules with β-(2,1) glycosidic bonds, and the end of each inulin molecule is connected with a glucose residue with α-(1,2) glycosidic bonds. The degree of polymerization is usually 2 to 60, and the average The degree of polymerization is 10. [0003] Inulin widely exists in some microorganisms and fungi in nature. However, it mainly exists in plants, such as Jerusalem artichoke, chicory, salsify, dahlia tubers, etc., among which Jerusalem artichoke is the main source of raw materials for inulin production. Jerusalem artichoke is commonly known as Jerusalem artichoke and ghost ginger. It is native to North America and is a perennial herb plant. It is w...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/18A61K31/733A61P39/06
Inventor 郭占勇任剑明董方冯艳彭德金
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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