Preparation method of phytosterol cinnamate

A technology for phytosterol esters and phytosterols, which is applied in the field of preparing phytosterol derivatives, can solve the problems of poor water solubility and fat solubility of phytosterols, limited application scope and the like, and achieves the effects of convenient preparation, widening application scope and improving fat solubility.

Inactive Publication Date: 2013-12-25
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, the water solubility and fat solubility of phytosterols are very poor, which limits its practical application range.

Method used

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  • Preparation method of phytosterol cinnamate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Add 0.2056g (0.5mmol) stigmasterol and 0.1480g (1mmol) cinnamic acid in the reaction flask with branch tube, feed N 2 After melting completely at 120°C under magnetic stirring, add 0.0038g (0.0125mmol) N-sulfonic acid propylpyrrolidone bisulfate and 0.0073g (0.0125mmol) cerous trifluoromethanesulfonate composite catalyst, at 120°C The reaction was incubated for 4 hours, and the reaction progress was detected by HPLC and TLC. After the reaction, the crude stigmasteryl cinnamate product was obtained, which was separated and purified by column chromatography to obtain the stigmasteryl cinnamate product, and its structure was identified by infrared, mass spectrometry and nuclear magnetic resonance spectrum analysis.

[0025] Stigmasteryl cinnamate: HPLC retention time (min) 7.345; IR (v, cm -1 )2942, 2866(C=C-H), 1710(C=O), 1640, 1454(C=C); MS m / z565.5(M + +Na), 475.4 (M + -C 7 h 6 +Na); 1 H NMR (400MHz, CDCl 3 , δ, ppm) 0.71 (3H, s, 18-H), 0.80 (6H, d, J=7.2Hz, 26-2...

Embodiment 2

[0027] Add 0.4102g (1mmol) stigmasterol and 0.1480g (1mmol) cinnamic acid in the reaction flask with branch tube, pass into N 2After melting completely at 160°C under magnetic stirring, add 0.0049g (0.02mmol) of N-sulfonic acid propylpyrrolidone chloride and 0.0117g (0.02mmol) of cerous trifluoromethanesulfonate composite catalyst, and keep warm at 160°C The reaction was carried out for 6 h, and the reaction progress was detected by HPLC and TLC. After the reaction, the crude product of stigmasteryl cinnamate was obtained, which was separated and purified by column chromatography to obtain the product of stigmasteryl cinnamate, and its structure was identified by infrared, mass spectrometry and nuclear magnetic resonance spectrum analysis, the data of which were the same as in Example 1.

Embodiment 3

[0029] Add 0.4082g (1mmol) phytosterol and 0.222g (1.5mmol) cinnamic acid in the reaction bottle with branch tube, pass into N 2 After melting completely at 140°C under magnetic stirring conditions, add 0.0041g (0.015mmol) N-sulfonic acid propylpyrrolidone nitrate and 0.0088g (0.015mmol) cerous trifluoromethanesulfonate composite catalyst, at 140°C The reaction was incubated for 3 h, and the reaction progress was detected by HPLC and TLC. After the reaction, the crude phytosteryl cinnamate product is obtained, which is separated and purified by column chromatography to obtain the phytosteryl cinnamate product, and its structure is identified by infrared, mass spectrometry and nuclear magnetic resonance spectrum analysis.

[0030] Cinnamic acid phytosterol ester: HPLC retention time (min) 6.321 ~ 8.159; IR (v, cm -1 ) 2940, 2866 (C=C-H), 1711 (C=O), 1639, 1450 (C=C); MS m / z553.4 (camesterol M + +Na), 565.5 (stigmasterol M + +Na), 567.5 (β-sitosterol M + +Na), 463.3 (cameste...

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Abstract

The invention relates to a novel preparation method of phytosterol cinnamate. According to the technical scheme, the preparation method comprises the following steps of: adding cinnamic acid and phytosterol to a reaction bottle with a branch pipe under the conditions of no solvent and nitrogen introduction, heating until the mixture is completely melted, next, adding an ionic liquid and a cerous triflate compound catalyst, carrying out an esterification reaction at a temperature in the range from 100 to 170 DEG C for 2-10 h, detecting the reaction process by using high performance liquid chromatography and thin-layer chromatography, and separating through column chromatography to obtain the pure phytosterol cinnamate product after the reaction is finished. The method provided by the invention is simple to operate, high in yield and friendly to environment; the catalyst is easy to recover and can be reutilized.

Description

technical field [0001] The invention relates to a method for preparing phytosterol derivatives, in particular to a method for preparing phytosterol cinnamate. The application and development of this product involves technical fields such as food, medicine, chemical industry and cosmetics. Background technique [0002] Phytosterols, also known as phytosterols, belong to plant steroid compounds, which are important components of plant cells and also a plant active ingredient. Phytosterols have cyclopentaneperhydrophenanthrene as the skeleton and belong to 4-methyl-free sterols. They mainly exist in nuts, seeds and grains, mainly including β-sitosterol, stigmasterol, brassicasterol and campesterol. Mainly β-sitosterol and stigmasterol. Phytosterols are generally extracted from the deodorized distillate during vegetable oil refining, and large-scale industrial production has been carried out in China at present. [0003] It was found that the more dietary intake of phytostero...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00C07J75/00
Inventor 贾承胜郭素洁张晓鸣
Owner JIANGNAN UNIV
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