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Preparation method for water-soluble phytosterin organic dibasic acid sugar ester

A technology of dibasic acid sugar esters and phytosterols, applied in the direction of organic chemistry, steroids, etc., to achieve the effects of high yield, mild reaction conditions and short reaction time

Active Publication Date: 2014-08-06
湖南禾益元生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are few reports on the research on improving the water solubility of phytosterols by structural modification. Therefore, the development of a new method for the preparation of water-soluble phytosterol derivatives will help to broaden its application in water-soluble foods. Significance

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Add 2.0750 g of phytosterols and 0.7500 g of succinic anhydride to a round bottom flask, dissolve in 10 ml of toluene, add 0.1250 g of DMAP to it, and reflux at 110° C. for 6 h. TLC detects the reaction process, adopts the high performance liquid phase method to measure the esterification rate, after the reaction finishes, obtains the thick product of phytosterol succinate, uses the silica gel of sherwood oil / ethyl acetate / formic acid (13:7:0.02) with mobile phase The pure product was obtained by column chromatography separation and purification. The structure was identified by infrared and mass spectrometry analysis, and the product was confirmed to be phytosterol succinate monoester.

[0032] Dissolve 0.5000 g of pure phytosterol succinate monoester in 10 ml of DMSO, add 0.2270 g of DCC and 0.0122 g of DMAP, and stir at room temperature for 1 h. Then, 5 ml of DMSO solution dissolved with 0.1980 g of glucose and 0.0266 g of p-toluenesulfonic acid was added thereto, and...

Embodiment 2

[0034] Add 2.0750 g of phytosterols and 0.9700 g of glutaric acid into a round bottom flask, dissolve them in 10 ml of toluene, add 0.1250 g of DMAP therein, and reflux at 110° C. for 6 h. TLC detects the reaction process, adopts the high performance liquid phase method to measure the esterification rate, after the reaction finishes, obtains the thick product of phytosterol glutarate, uses the silica gel of sherwood oil / ethyl acetate / formic acid (13:7:0.02) with mobile phase The pure product was obtained by column chromatography separation and purification. The structure was identified by infrared and mass spectrometry analysis, and the product was confirmed to be phytosterol glutaric acid monoester.

[0035] Dissolve 0.5140 g of pure phytosterol glutaric acid monoester in 10 ml of DMSO, add 0.2270 g of DCC and 0.0122 g of DMAP, and stir at room temperature for 1 h. Then, 5 ml of DMSO solution dissolved with 0.3760 g of lactulose and 0.0266 g of p-toluenesulfonic acid was adde...

Embodiment 3

[0037] Add 2.0750 g of phytosterols and 1.1000 g of adipic acid into a round bottom flask, dissolve them in 10 ml of toluene, add 0.1250 g of DMAP therein, and reflux at 110° C. for 6 h. TLC detects that the phytosterol disappears and terminates the reaction, and adopts high-performance liquid phase method to measure the esterification rate. After the reaction, the thick product of phytosterol adipate is obtained, and the mobile phase is sherwood oil / ethyl acetate / formic acid (13:7: 0.02) of silica gel column chromatography separation and purification, to obtain pure product, using infrared and mass spectrometry for structural identification, determined to be phytosterol adipate monoester.

[0038] After dissolving 0.5280 g of pure phytosterol adipate monoester in 10 ml of DMSO, 0.2270 g of DCC and 0.0122 g of DMAP were added thereto, and stirred at room temperature for 1 h. Then, 5 ml of DMSO solution in which 0.3760 g of trehalose and 0.0266 g of p-toluenesulfonic acid were ...

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Abstract

The invention relates to a preparation method for phytosterin organic dibasic acid sugar ester. The invention adopts the following technical scheme: dicyclohexyl carbon imide (DCC), 4- dimethylamino pyridine (DMAP) and p-toluene sulfonic acid (p-TsOH) composite catalyst are adopted to catalyze the esterification between the phytosterin organic dibasic acid monoester and functional sugar; first of all, the DCC and the DMAP are adopted to activate the phytosterin organic dibasic acid monoester for 1 hour; then, the functional sugar and the p-Ts OH are added; an ultrasonic reaction is conducted in an ultrasonic instrument at a room temperature and the overall reaction time lasts for 10 hours; through the separation of the silica gel column chromatography, the phytosterin organic dibasic acid sugar ester is obtained after the ultrasonic reaction is completed. The phytosterin organic dibasic acid sugar ester prepared by the preparation method has the biological activity of the phytosterin and the functional sugar; the operation is simple; the reaction conditions are mild; the energy consumption is low; the productivity is high; the properties of the phytosterin organic dibasic acid sugar ester are stable, and are convenient to store.

Description

technical field [0001] The invention relates to a method for preparing phytosterol derivatives, in particular to a method for preparing water-soluble phytosterol organic dibasic acid sugar ester. The application and development of this product involves technical fields such as food, medicine, chemical industry and cosmetics. Background technique [0002] Phytosterols are natural active substances present in plants, widely distributed in nature, and are most abundant in vegetable oils, seeds and nuts, grains, and beans. There are many kinds of natural phytosterols, mainly β-sitosterol, stigmasterol and campesterol. They all belong to 4-methyl-free sterols, and their structure is similar to that of cholesterol. The main skeleton of the steroid core is cyclopentane polyhydrophenanthrene, and its C A hydroxyl group is attached to the -3 position. In recent years, studies on phytosterols have shown that it is a kind of natural active substance with no toxic and side effects on ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00
Inventor 贾承胜任明星林蔚婷张晓鸣
Owner 湖南禾益元生物科技有限公司
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