A kind of method that catalyzes sesamolin to prepare sesamol

A technology of sesamol and sesamolin, which is applied in the field of preparation of sesamol, can solve problems such as unsatisfactory industrial production, high technical level requirements for equipment, limited amount of sesamol, etc., and achieve low cost, green process and chemical properties stable effect

Active Publication Date: 2016-06-15
HENAN ACAD OF AGRI SCI
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Problems solved by technology

But the amount of sesaminol obtained by these two methods is limited, such as ShigenoriKumazawa, MihoKoike, YumikoUsut, etc.IsolationofSesaminolsasAntioxidativeComponentsfromRoastedSesameSeedOil[J].J.OleoSci.,2003,52(6):303-307 directly isolated from sesame seeds , the amount of sesamolin obtained by extracting is only 0.002%; The method uses acid clay decolorized sesame oil as raw material, and the amount of sesaminol obtained by separation and purification is only 0.015%
The above two methods for preparing sesaminol have complex steps, high technical requirements for equipment, and low purification efficiency, which cannot meet the requirements of industrial production.
Patent ZL00910065650.3 (a method for preparing sesamol) discloses a method for preparing sesamol by using H-type strongly acidic styrene-based cation exchange resin as a catalyst to catalyze sesamol in a benzene-based solvent, although the method Compared with the traditional method, the conversion process is stable, the yield of sesaminol is high, the separation and purification is simple, and the process is green, etc., but the reaction solvent used is a benzene-based solvent, which is highly toxic and limits the scope of use of the product to a certain extent.

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  • A kind of method that catalyzes sesamolin to prepare sesamol

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Embodiment 1

[0021] A method for catalyzing sesalin for the preparation of sesaminol, specifically: taking sesalin crude product (containing sesalin 62.9% and sesamin 36.2%) 0.5g (containing sesalin 0.85mmol) and 20mL petroleum ether and added it to the In a 50mL three-necked flask (the initial concentration of sesaline is 42.5mmol·L -1 ), stirred and preheated to 100 °C, and then added 15 g of silicotungstic heteropolyacid catalyst activated at 200 °C for 3 h (17.6 g·mmol relative to the initial sesamin -1 ), continue to stir and keep the reaction at 100 °C for 2 hours, and the reaction solution at the time of HPLC determination of the reaction for 2 hours is converted into sesaminol with a yield of 90.2%. After cooling, suction filtration, the catalyzer is washed twice with acetone again, and the washing solution obtained twice is combined with the organic phase obtained by suction filtration and adopts preparative liquid chromatography to collect the sesaminol component at 295 nm, and t...

Embodiment 2

[0023] A method for preparing sesaminol by catalyzing sesalin, specifically: get sesalin pure product (purity is 98%) 80mg (0.216mmol) and 20mL ethylbenzene and join in the 50mL three-necked flask (the sesalin initial concentration is 10.8 mmol·L -1 ), stirred and pre-heated to 90°C, and then added 3 g of silico-molybdenum heteropolyacid activated at 200°C for 3 h (13.89 g·mmol relative to the initial sesamin -1), continue to stir and keep the reaction at 90°C for 1.5h, the reaction solution at 1.5h was measured by HPLC, and the yield of sesaminol was 87.9%. After cooling, suction filtration, wash the catalyst twice with ethyl acetate, combine the washings obtained twice and evaporate the solvent under reduced pressure together with the organic phase obtained by suction filtration to obtain a yellow-brown paste-like solid, which is purified by silica gel column chromatography. N-hexane and ethyl acetate are eluted at 5:1, TLC detects, collects sesaminol components, evaporates...

Embodiment 3

[0025] A method of catalyzing sesalin for the preparation of sesaminol, specifically: get sesalin pure product 66mg (purity is 98%, 0.18mmol) and 10mL benzene join in the 25mL three-necked flask (the sesalin initial concentration is 18mmol L -1 ), stirred and pre-heated to 70 °C, and then added cesium phosphotungstic heteropolyacid (Cs) activated at 200 °C for 2 h 2.5 H 0.5 PW 12 O 40 ) 0.72g (4g mmol relative to initial sesaline -1 ), continue to stir and keep the reaction at 70°C for 4h, the reaction solution at 4h was measured by HPLC, and the yield of sesaminol after conversion was 82.5%. Then handle according to the method of embodiment 2, obtain yellow-brown sesaminol solid 43.5mg, HPLC measures total sesaminol content to be 98.2%, and yield is 63.6%. The pure sesaline and benzene were dehydrated and dried before the reaction.

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Abstract

The invention relates to a method for preparing sesamol by catalyzing sesamolin, which comprises the following steps: reacting sesamolin in a non-active hydrogen solvent at 70-110 DEG C under the action of a catalyst for 1-6 hours, and carrying out after-treatment on the reaction solution to obtain sesamol, wherein the catalyst is heteropoly acid, heteropoly acid salt, loaded heteropoly acid or loaded heteropoly acid salt. The catalyst in the method can be recovered only by simple washing, drying and activating treatment, and has the advantages of low cost and environmental protection. Compared with the traditional method, the method provided by the invention has the advantages of accessible raw materials, stable conversion technique, high sesamol yield, simple separation and purification, green technique and the like.

Description

technical field [0001] The invention belongs to the technical field of sesaminol preparation, and in particular relates to a method for preparing sesaminol by utilizing heteropolyacid (salt) or loaded heteropolyacid (salt) to catalyze sesaminol. Background technique [0002] Sesaminol, molecular formula C 20 H 18 O 7 , is a kind of natural antioxidant active ingredients of sesame lignans. Compared with other antioxidant active ingredients (structural formula shown below) in sesame oil such as sesamol, sesamin and sesamin, its antioxidant capacity is the strongest, It is also the most stable. Sesaminol not only has antioxidant properties, it can be used as a natural antioxidant, but also has a wide range of biological activities. 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 excellent antioxidant properties. oxidative capacity. [0003] [0004] Sesame and ses...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 张丽霞孙强宋国辉芦鑫黄纪念
Owner HENAN ACAD OF AGRI SCI
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