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Ingenol and preparation method therefor

A technology of ingenol and methanol, which is applied in the field of ingenol and its preparation, can solve problems such as environmental pollution, complicated steps, and human damage, and achieve the effects of reducing production costs, simplifying separation steps, and simplifying the production process

Active Publication Date: 2015-11-18
无锡紫杉药业股份有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although this invention can realize the separation of ingenol, its steps are more complicated, the hydrolysis efficiency of step a is low, a large amount of strong alkali solution is needed and a large amount of highly volatile toxic solvent such as THF is used in the separation process, which is easy to harm the human body Cause damage, cause pollution to the environment, not suitable for industrial production, do not meet the requirements of green environmental protection, and in the purification process of products using gravity silica gel column chromatography, it needs to be eluted with gradient petroleum ether-ethyl acetate, and the solvent cannot be recovered Reuse, the cost is high, is not conducive to industrial production, and the product purity must reach more than 99%, it must be separated by silica gel column for many times, and it can be realized by multiple gradient elutions

Method used

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  • Ingenol and preparation method therefor
  • Ingenol and preparation method therefor
  • Ingenol and preparation method therefor

Examples

Experimental program
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Effect test

Embodiment 1

[0058] In this embodiment, ingenol is prepared by the following method, which specifically includes the following steps:

[0059] (1) Pulverize 10kg caper seeds, add 30L industrial methanol solvent to the pulverized caper seeds, extract by cold soaking for 3 times, each time for 12 hours, combine the extracts, concentrate the extracts to 4L, reclaim methanol ;

[0060] (2) add 10L sherwood oil to the extract that step (1) obtains and extract 3 times, take the methanol solution of the lower layer, concentrate, and obtain about 220g of the concentrate;

[0061] (3) Add 2.2L0.1mol / L LiOH to the concentrate obtained in step (2) and stir for 15 hours. After the reaction, add 2.2L0.1mol / L acetic acid to neutralize, and then concentrate and evaporate to dryness to obtain ingenol-containing sample;

[0062] (4) Dissolve 220g of the sample obtained in step (3) in methanol, then mix with 220g of silica gel, grind evenly, dry, and carry out chromatographic separation. The column chroma...

Embodiment 2

[0067] In this embodiment, ingenol is prepared by the following method, which specifically includes the following steps:

[0068] (1) Pulverize 20kg caper seeds, add 60L industrial methanol solvent to the pulverized caper seeds, extract by cold soaking twice, each time for 12 hours, combine the extracts, concentrate the extracts to 4L, reclaim methanol ;

[0069] (2) add 20L sherwood oil to the extract obtained in step (1) and extract for 2 times, take the methanol solution in the lower layer, and concentrate to obtain about 440g of the concentrate;

[0070] (3) Add 4.4L0.2mol / L LiOH to the concentrate obtained in step (2) and stir for 12 hours. After the reaction, add 4.4L0.2mol / L acetic acid to neutralize, and then concentrate and evaporate to dryness to obtain ingenol-containing sample;

[0071] (4) Dissolve 440g of the sample obtained in step (3) in methanol, then mix with 440g of silica gel, grind evenly, dry, and carry out chromatographic separation. The column chromat...

Embodiment 3

[0075] In this embodiment, ingenol is prepared by the following method, which specifically includes the following steps:

[0076] (1) 50kg of caper seeds are pulverized, 150L of industrial methanol solvent is added to the pulverized caper seeds, cold extraction is extracted 3 times, each time for 12 hours, the extracts are combined, and the extracts are concentrated to 10L;

[0077] (2) Add 50L sherwood oil to the extract obtained in step (1) to extract 3 times, take the methanol solution in the lower layer, and concentrate to obtain about 1100g of the concentrate;

[0078] (3) Add 11L0.4mol / L LiOH to the concentrate obtained in step (2) and stir for 10 hours. After the reaction, add 11L0.4mol / L acetic acid for neutralization, then concentrate and evaporate to dryness to obtain a sample containing ingenol ;

[0079] (4) Dissolve 1100g of the sample obtained in step (3) in methanol, then mix with 1100g of silica gel, grind evenly, dry, and carry out chromatographic separation....

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Abstract

The present invention provides ingenol and a preparation method therefor. The method comprises: by taking euphorbia lathyris seeds as raw materials, obtaining the ingenol through recovery, extraction, hydrolysis reaction and silica gel column chromatography. According to the ingenol and the preparation method therefor, types off solvents used in the whole preparation process are less; both an extraction solvent and an extracting solvent are methanol; the solvent can be reused, so that the production cost is reduced, and the production process is simplified; the hydrolysis reaction of an ingenol esterified compound is performed by use of a strong base; by virtue of this reaction, an esterified compound of the ingenol can be converted into the ingenol, so that the separation process is simplified; and the ingenol with purity higher than 98% can be acquired through silica gel column chromatography for separation, so that use of a high-pressure reversed phase chromatography system is avoided, and the separation conditions are simplified. By use of the preparation method provided by the present invention, industrial preparation of the ingenol can be achieved, the preparation yield is high, and the product purity is high.

Description

technical field [0001] The invention belongs to the technical field of separation and purification, and relates to ingenol and a preparation method thereof. Background technique [0002] Picato gel is currently the first and only preparation that can be used to treat actinic keratosis (AK). It has a certain effect on the early detection and treatment of skin cancer, and the preparation has a broad market prospect. The main component of Picato gel is ingenol methacrylate, which is mainly obtained from the synthesis of ingenol and angelic acid glycosides derived from the seeds of Capsicum sativa. The preparation of ingenol has been reported in related literatures, but the preparation scale is still in the laboratory stage, and the cost of industrial preparation is relatively high. [0003] For example, CN103694096A discloses a method for separation and purification of ingenol monomer. The invention is based on Euphorbiaceae Euphorbiaceae traditional Chinese medicine Daffodil ...

Claims

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Application Information

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IPC IPC(8): C07C45/78C07C45/85C07C45/80C07C49/727
CPCC07C45/78C07C45/80C07C45/85C07C49/727
Inventor 王永毅朱海波葛月兰
Owner 无锡紫杉药业股份有限公司
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