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Synthetic Technology of High Purity α-Mangostin

A synthesis process and technology of mangostin, which is applied to the synthesis process of high-purity natural product α-mangostin, and the field of natural product synthesis, which can solve the problems of low overall yield, high cost, and long route, and achieve post-processing Simple, convenient synthesis, high yield effect

Inactive Publication Date: 2016-09-28
BOMAI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, α-mangostin is mainly extracted from mangosteen husk, but the crude product contains β-mangostin and γ-mangostin with similar properties, and it is difficult to achieve purity through simple recrystallization. very high alpha-mangostin
In terms of industry, α-mangostin with a purity of >70% or even >90% can be obtained through natural extraction, recrystallization, etc., but the cost is high, and it is impossible to obtain high-purity α-mangostin that meets the requirements of pharmaceutical raw materials ( 95%~99.9%) products
[0006] The structure of α-mangostin is complex, and only a few literatures report the synthesis methods of α-mangostin, but the routes are long, the overall yield is low, and the cost is high, so industrial production cannot be realized

Method used

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  • Synthetic Technology of High Purity α-Mangostin
  • Synthetic Technology of High Purity α-Mangostin
  • Synthetic Technology of High Purity α-Mangostin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The synthetic route 1 of the synthetic process method of high-purity natural product α-mangostin is as follows:

[0028]

[0029] On the acetyl group:

[0030] Weigh 250g of α-mangostin crude product SM_1 (purity>70%) into a 5L three-neck flask, add 1L of pyridine under the condition of stirring in an ice bath, slowly add acetic anhydride (1.25L), and control the temperature in the kettle at 10 below the degree. After dropping, heat to reflux for 3h. Concentrate the excess pyridine, add 1.2L of dichloromethane to the concentrate, wash the organic phase twice with 5% dilute hydrochloric acid 600mL×2, back-extract the dilute hydrochloric acid layer with 300mL×2 dichloromethane, and combine the organic phases. The organic phase was washed with 300 mL of saturated brine, dried over anhydrous sodium sulfate, and spin-dried to obtain 326 g of a brown oil, which became solid after cooling at room temperature. The crude product was recrystallized twice with dichloromethan...

Embodiment 2

[0053] The synthesis route of the synthesis process of α-mangostin in this embodiment is the same as that in Example 1.

[0054] On the acetyl group:

[0055] Weigh 250g of the crude α-mangostin SM_1 (purity>70%) into a 5L three-neck flask, add 1L of pyridine under the condition of stirring in an ice bath, slowly add acetyl chloride (470g), and control the temperature in the kettle at 10 degrees the following. After dropping, heat to reflux for 3h. Concentrate the excess pyridine, add 1.2L dichloromethane to the concentrated solution, wash the organic phase twice with 5% dilute hydrochloric acid 600mL×2, separate the layers, back-extract the dilute hydrochloric acid layer with 300mL×2 dichloromethane, and combine the organic phases . The organic phase was washed with 300 mL of saturated brine, dried over anhydrous sodium sulfate, and spin-dried to obtain 300 g of a brown oil, which became solid after cooling at room temperature. The crude product was recrystallized twice w...

Embodiment 3

[0059] The synthetic route 2 of the synthetic process method of high-purity natural product α-mangostin is as follows:

[0060]

[0061] Weigh 250g of α-mangostin crude product SM_1 (purity>70%) into a 5L three-necked flask, add 1L of pyridine under the condition of stirring in an ice bath, and start slowly dropwise when the temperature in the reactor drops below 10 degrees Chlorine acetate (95g), the temperature in the kettle is controlled below 10 degrees, and the dropping time is about 0.5h. After dropping, react overnight at room temperature. Rotary evaporate excess pyridine, add 1.2L dichloromethane to the concentrated solution, wash the organic phase twice with 5% dilute hydrochloric acid 600mL×2, separate the layers, back-extract the dilute hydrochloric acid layer with 300mL×2 dichloromethane, and combine The organic phase. The organic phase was washed with 300 mL of saturated brine, dried over anhydrous sodium sulfate, and spin-dried to obtain 250 g of a brown oil...

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Abstract

The invention relates to a synthesis process method of high-purity natural product alpha-mangostin, comprising the following steps: (1) reacting alpha-mangostin extracted through a process as an initial raw material with different acylation reagents in an alkaline solvent, recrystallizing to remove partial impurity to obtain phenolic hydroxy substituted alpha-mangostin with higher purity; (2) reacting the synthesized intermediate phenolic hydroxy substituted alpha-mangostin with different reagents in the solvent to remove protecting group, reverse extracting through acid-base, recrystallizing, decoloring, and further purifying to obtain the high-purity alpha-mangostin. The method provided by the invention is convenient to synthesize, high in yield, and capable of meeting the demand of the medicine to the quality.

Description

technical field [0001] The invention relates to a synthesis method of a natural product with anti-senile dementia and anti-dysentery effects in the technical field of medicinal chemistry, in particular to a synthesis process method of a high-purity natural product α-mangostin. Background technique [0002] α-Mangostin, the chemical name is 1,3,6-trihydroxy-7-methoxy-2,8-bis(3-methyl-2-butenyl)-9H-oxanthene-9- Ketone is a xanthone compound extracted from the plant Mangosteen, and its structure is as follows. [0003] [0004] Recently, it has been reported in the literature that α-mangostin has pharmacological effects such as anti-senile dementia and anti-dysentery, and has certain medicinal application value. In addition, α-mangostin is derived from the active ingredients of natural mangosteen, which is safe, non-toxic and has a long history of consumption. It provides a theoretical and application basis for in-depth research on α-mangostin as a drug. [0005] At presen...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/86
CPCY02P20/55
Inventor 夏铮余沛霖朱义平杨巍瞿国伟刘振明刘路英
Owner BOMAI