Preparation method of sesamin phenol

A technology of sesaminol and sesaminol, which is applied in the preparation field of sesaminol, can solve the problems of complex sesaminol method steps, can not meet the high requirements of industrialized production and equipment technical level, and achieves green technology, low cost and raw materials. easy-to-get effect

Inactive Publication Date: 2010-02-17
河南省农科院农副产品加工研究所
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Generally speaking, the above two methods for preparing sesaminol have complicated steps, high requirements for equipment technical level, low purification efficiency, and cannot meet the requirements of industrial production.

Method used

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  • Preparation method of sesamin phenol

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Experimental program
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Effect test

Embodiment 1

[0025] Get sesamolin crude product (containing sesamolin 62.9% and sesamolin 36.2%) 0.5g (containing sesamolin 0.85mmol), 20mL toluene joins in the 50mL three-necked flask (the initial concentration of sesamolin is 42.5mmol L -1 ), stirred and preheated to 100°C, then added 15g of 001x7 cation exchange resin (polystyrene matrix) treated into H type and dried (17.6g·mmol relative to the initial sesamolin -1 ), kept stirring and kept the same temperature for 2h, and HPLC measured the reaction solution when reacting for 2h, and the yield of converting sesaminol was 81.5%. Suction filtration after cooling, the catalyst was washed twice with acetone, the filtrates were combined, and the solvent was evaporated under reduced pressure to obtain a yellow-brown paste solid, which was purified by silica gel column chromatography, and first eluted with n-hexane and ethyl acetate at a ratio of 8:1 , TLC monitoring reaction (developing agent is n-hexane: ethyl acetate=4: 1), when the eluent...

Embodiment 2

[0027] Get sesamolin pure product (purity is 98%) 40mg (0.108mmol), 10mL xylene joins in the 25mL three-necked flask (sesamolin concentration is 10.8mmol L -1 ), stirred and preheated to 90°C, then added 1.5g of D001 cation exchange resin (macroporous polystyrene matrix) treated into H type and dried (13.89g·mmol relative to the initial sesamolin -1 ), kept stirring and kept the same temperature for 4h, HPLC measured the reaction solution after 4h, and converted to 73.8% of the yield of sesaminol. After cooling, it was filtered with suction, washed twice with ethyl acetate, and the filtrates were combined, and the solvent was evaporated under reduced pressure to obtain a yellow-brown paste solid, which was purified by silica gel column chromatography, eluted with n-hexane and ethyl acetate at a ratio of 4:1, monitored by TLC, and collected For the sesamol component, the solvent was evaporated under reduced pressure to obtain 25.6 mg of yellow-brown sesamol solid, the total ses...

Embodiment 3

[0029] Get sesamolin pure product (purity is 98%) 66mg (0.18mmol), 10mL benzene joins in the 25mL three-necked flask (sesamolin concentration is 18mmol L -1 ), stirred and pre-heated to 70 ° C, then added 0.72 g of 001x7 cation exchange resin (polystyrene matrix) treated into H type and dried (4 g·mmol relative to the initial sesamolin -1 ), kept stirring and kept the same temperature for 5h, and HPLC measured the reaction solution after 5h, and the yield of converting sesaminol was 68.9%. Afterwards, according to the method of Example 2, 38.7 mg of yellow-brown sesamol solid was obtained, and the total sesamol content determined by HPLC was 98.2%, and the yield was 58.6%, wherein the sesamol content was its isomer 2-episesamin 1.42 times that of phenol. Sesamolin pure product, benzene, and catalyst are dehydrated and dried before the reaction.

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Abstract

The invention relates to a preparation method of esamin phenol. Sesamolin reacts in a benzene series solvent under the action of a catalyzer at the temperature of 70-110 DEG C for 1-6h, and sesamin phenol is obtained after a reaction solution is treated, wherein the catalyzer is an H-type strongly acidic styrene which is cation exchange resin. Compared with the traditional methods, the preparationmethod has the advantages of available raw material, stable conversion process, high sesamin phenol yield, simple separation and purification, green process and the like.

Description

(1) Technical field [0001] The invention relates to a preparation method of sesaminol. (2) Background technology [0002] Sesamol is a natural antioxidant active ingredient of lignans mainly present in sesame oil, with the molecular formula C 20 h 18 o 7 , compared with other antioxidant active ingredients (structural formula shown below) in sesame oil, such as sesamol, sesamin and sesamolin, its antioxidant capacity is the strongest, and it is also the most stable. The existence of these antioxidant components is the reason why sesame oil still maintains high stability and is not easy to oxidize and deteriorate although it contains more unsaturated fatty acids such as oleic acid and linoleic acid. Sesamol not only has antioxidant properties, but also has a wide range of biological activities as a natural antioxidant. It can not only protect and strengthen liver function, regulate blood pressure, lower cholesterol, but also directly act on tissues and organs to exert its ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/04B01J31/08
Inventor 黄纪念宋国辉孙强詹传保
Owner 河南省农科院农副产品加工研究所
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