Preparation method of acetylated epigallocatechin gallate

A technology of epigallocatechin and gallate, applied in the field of preparing acetylated epigallocatechin gallate

Inactive Publication Date: 2012-03-21
宜昌绿源生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Studies have shown that after being treated with 50gmol / L pro-EGCG for 24 hours, the activity of chymotrypsin is inhibited by 48%, while the inhibitory effect of (-)-EGCG at the same dose is only 8%.

Method used

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  • Preparation method of acetylated epigallocatechin gallate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Add 9.2g (about 0.02mol) of EGCG to a 250ml three-neck flask with a magnet, dissolve it with 40-200ml of ethyl acetate, preferably 60-100ml of ethyl acetate as a solvent, add 20-160ml of acetic anhydride (about 0.1 ~0.8mol), the best dosage is 30-60ml.

[0026] Add catalyst ZnCl 2 1.36~27.6g (about 0.01~0.2mol), preferably 6.8~20.4g (0.05~0.15mol) as the catalyst. Stir at room temperature for 3-8 hours. As the reaction continued, the homogeneity of the system continued to increase, and the system gradually changed from a yellow turbid liquid to a transparent light brown liquid, and the reaction was detected by TLC. Add 80~200ml of saturated sodium bicarbonate, continue to stir for 1 h, separate the ethyl acetate layer, then extract the water phase with ethyl acetate (100ml / time) for 3 times, combine and dry the ethyl ester layer, and remove the ethyl acetate by rotary evaporation. 16g of light brown transparent oil was obtained, with a yield of 98%. Recrystallized onc...

Embodiment 2

[0028] Add 9.2g (about 0.02mol) of EGCG to a 250ml three-neck flask with a magnet, dissolve it with 40-200ml of ethyl acetate, preferably 60-100ml of ethyl acetate as a solvent, add 20-160ml of acetic anhydride (about 0.1 ~0.8mol), the best dosage is 30-60ml.

[0029] Add catalyst ZnAc 24.25~37g (about 0.025~0.2 mol) The best dosage can be 13.88~24 (about 0.075~0.12mol). Stirred at 80 DEG C for 5h, along with the continuous progress of the reaction, the uniformity of the system was continuously enhanced, and the system gradually changed from a yellow turbid liquid to a transparent dark brown liquid, and the TLC detection reaction ended. Add 80ml of saturated sodium bicarbonate, continue to stir for 1 h, separate the ethyl acetate layer, then extract the water phase with ethyl acetate (100ml / time) for 3 times, combine and dry the ethyl ester layers, remove the ethyl ester by rotary evaporation, and obtain 15.7 g Dark brown transparent oil, yield 96%, recrystallized once with ...

Embodiment 3

[0031] Add 1840g (about 4mol) of EGCG into a 50L reactor equipped with mechanical stirring, dissolve it with 8~36L of ethyl acetate, the optimum solvent volume is 12~24L, add 6-16L of acetic anhydride (about 30~80mol), and add the catalyst ZnCl 2 170~1360g (about 1.25~10mol), the best dosage is 510~1020g (about 3.65~7.5mol), and the system is a heterogeneous system. Stirring at room temperature for 7 hours, as the reaction continued to increase the uniformity of the system, the system gradually changed from a yellow turbid liquid to a transparent light yellowish brown liquid, and TLC detected that the reaction was over. Add 16L of saturated sodium bicarbonate, continue to stir for 1 h, separate the ethyl acetate layer, and then extract the water phase with ethyl acetate (20L / time) in the extraction tower for 3 times, combine and dry the ethyl layer, and remove the ethyl acetate layer by rotary evaporation. Esters, about 3100g light brown transparent oil was obtained, with a y...

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Abstract

The invention discloses a preparation method of acetylated epigallocatechin gallate. The preparation method comprises the following steps of taking dissolved EGCG (epigallocatechin gallate) as a raw material; adding an acetylating reagent and an esterification catalyst; performing acetylization reaction on EGCG at 0-120 DEG C while stirring; after reacting for 1-24 hours and when a system becomes from a yellow turbid liquid into a transparent hazel liquid, ending the acetylization reaction; and purifying to obtain the acetylated epigallocatechin gallate. The preparation method of the acetylated epigallocatechin gallate has the characteristics that the acetylation is complete, the conversion rate is higher than 98%, and the yield is high.

Description

technical field [0001] The invention relates to a method for preparing acetylated epigallocatechin gallate. Background technique [0002] (-)-Epigallocatechin gallate (EGCG) is a major component extracted from Chinese green tea. It is the main active and water-soluble component of green tea. 9%-13% of the gross weight of green tea. Because of its special stereochemical structure, EGCG has very strong antioxidant activity and plays an important role in anti-cancer and cardiovascular diseases. In addition, it is also used as a reversal agent of tumor multidrug resistance, which can improve the sensitivity of cancer cells to chemotherapy and reduce the toxicity to the heart. [0003] (-)-Epigallocatechin gallate (EGCG) is the most effective antioxidant polyphenol in green tea, which has antioxidative, anticancer, antimutagenic and other activities. The antioxidant activity is at least 100 times that of vitamin C and 25 times that of vitamin E. It can protect cells and DNA fro...

Claims

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Application Information

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IPC IPC(8): C07D311/62
Inventor 王军伟龙清书尤庆亮邓道静
Owner 宜昌绿源生物技术有限公司
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