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A kind of preparation method of gallic acid phytosterol ester

A technology of phytosterol esters and gallic acid, which is applied in the field of preparation of new oil-soluble phytosterol esters, can solve the problems of no industrial application value, high reaction temperature, and many by-products, so as to improve oil solubility, biological activity, and reaction efficiency High and simple steps

Inactive Publication Date: 2016-06-15
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] There is no report about gallic acid phytosterol esters at present. It is common to report that gallic acid reacts with long-chain sugar alcohols, but their common points are that the reaction temperature is high, there are many by-products, and the whole reaction process is too toxic. no industrial value

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: the synthesis of triacetyl gallic acid

[0034] Weigh 17.0g of gallic acid, add it into 200mL sodium hydroxide solution with a concentration of 1.5mol / L under ice bath, stir at low speed to dissolve the solid, slowly add 18.8mL of acetic anhydride in total dropwise, keep stirring at low speed during this period, and react at room temperature for 2.5 hours . After the reaction, concentrated hydrochloric acid was added to adjust the pH of the solution to 1, and a white solid was precipitated. The solution was filtered with suction, washed with a small amount of cold water, and dried to obtain 27.4 g of triacetyl gallic acid with a yield of 92.6%. Structural identification was performed by mass spectrometry.

[0035] Triacetyl gallic acid: HPLC retention time (min) 1.945; MSm / z319 (triacetyl gallic acid M + +Na).

Embodiment 2

[0036] Embodiment 2: the synthesis one of triacetyl gallic acid phytosterol ester

[0037] Will homemade TiO 2 The carrier was impregnated with 1mol / L concentrated sulfuric acid solution at 15mL / g for 2 hours, then filtered, washed the filter cake twice with deionized water, dried at 100°C for 12 hours, and calcined in a muffle furnace at 400°C for 3 hours. Obtain solid superacid SO4 2- / TiO 2 .

[0038] Weigh 16.52g of phytosterols and 5.92g of triacetyl gallic acid, add them to the flask with 300mL dimethylformamide in advance, and after they are completely dissolved, add the self-made solid super acid SO 4 2- / TiO 2 0.71g, react in a bath-type ultrasonic generator with a frequency of 25KHz at room temperature, control the ultrasonic power to 700W, take samples every 0.5 hours, use high-performance liquid chromatography to detect the reaction process, stop the reaction for 5 hours, remove the catalyst by suction filtration, and evaporate to dryness The filtrate obtains...

Embodiment 3

[0040] Embodiment 3: the synthetic two of triacetyl gallic acid phytosterol ester

[0041] Dissolve 5g of sodium tungstate in 10mL of distilled water, heat to boiling, add 0.6g of disodium hydrogen phosphate, adjust the pH to 1.5 with concentrated hydrochloric acid, then cool and filter, take the filtrate and add 4mL of concentrated sulfuric acid drop by drop, let stand to separate layers, and remove the lower layer Phosphotungstic heteropolyacid PW obtained by drying 12 (H 3 PW 12 o 40 .nH 2 O). Take 2gPW 12 Dissolve in absolute ethanol, add 10g of tin oxide solid powder, stir until the ethanol is volatilized, and calcinate the solid in a muffle furnace at 300°C for 4 hours to obtain a tin oxide immobilized phosphotungstic compound with a solid loading capacity of 20%. sour.

[0042] Weigh 12.36g of stigmasterol and 2.96g of triacetyl gallic acid, and add them to a flask with 200mL of dimethylformamide in advance. Polyacid 0.24g, react in a bath type ultrasonic genera...

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PUM

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Abstract

The invention relates to a method for preparing phytosterol ester, in particular relates to a preparation method of gallate phytosterol ester, belongs to the technical field of foods, medicines, chemical engineering and cosmetics according to the application and development, and aims at solving the problem that the current study on modification of phytosterol ester focuses on the synthesis of fatty acid phytosterol ester and little study is performed for aromatic acid, and most of the studies suffer from the shortages like high reaction temperature and low practicability. The preparation method aims at synthesizing gallate phytosterol ester to improve the solubility and biological activity of phytosterol ester. The method comprises the following steps: a) synthesizing triacetyl gallate by the aqueous phase process; b) enabling phytosterol ester to react with triacetyl gallate at room temperature under the ultrasonic assisting catalyzing to generate triacetyl phytosterol ester; c) performing refluxing and deacetylation through a trichloromethane-methyl alcohol-sodium carbonate solution to generate oil-soluble gallate phytosterol ester. The method is simple in experimental operation, small in energy consumption, high in efficiency, high in yield and suitable for industrial food production.

Description

technical field [0001] The invention relates to a preparation method of a novel oil-soluble phytosterol ester, which belongs to the technical fields of food, medicine, chemical industry, cosmetics and the like. Background technique [0002] Phytosterols, also known as phytosterols, are a class of steroidal compounds with cyclopentaneperhydrophenanthrene as the main skeleton, and are an important plant active ingredient. 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. Phytosterols mainly include β-sitosterol, stigmasterol, brassicasterol and campesterol, among which β-sitosterol is the main one. Phytosterols are best known for their cholesterol-lowering effects. In recent years, it has also been found that phytosterols play an important role in anti-cancer, anti-inflammation, anti-virus and improving immunity. [0003] Phytosterols have a very g...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J9/00
CPCC07J9/00
Inventor 贾承胜霍振宇张晓鸣
Owner JIANGNAN UNIV