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Method for preparing sesamol by catalyzing sesamolin

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: 2014-09-24
HENAN ACAD OF AGRI SCI
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  • Abstract
  • Description
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Problems solved by technology

But the amount of sesaminol obtained by these two methods is limited, such as Shigenori Kumazawa, Miho Koike, Yumiko Usut, etc. Isolation of Sesaminols as Antioxidative Components from Roasted Sesame Seed Oil [J]. J. Oleo Sci., 2003, 52(6):303-307 The amount of sesaminol obtained by direct isolation and extraction from sesame seeds is only 0.002%; from Sesamolin [J]. Agric. Biol. Chem., 1987, 51 (5): 1285-1289 described in the method, with acid clay decolorized sesame oil as raw material, the amount of sesamolin 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 preparation method of 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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  • Method for preparing sesamol by catalyzing sesamolin

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Embodiment 1

[0021] A method for preparing sesamol by catalyzing sesamolin, specifically: take 0.5 g of crude sesamolin (containing 62.9% sesamolin and 36.2% sesamolin) (containing 0.85 mmol of sesamolin) and add 20 mL of petroleum ether to In a 50mL three-neck flask (the initial concentration of sesamolin is 42.5mmol·L -1 ), stirred and preheated to 100°C, then added 15g of silicotungstic heteropolyacid catalyst activated at 200°C for 3h (17.6g·mmol relative to the initial sesamolin -1 ), continuously stirred and kept at 100°C for 2h, and the reaction liquid was measured by HPLC for 2h, and the yield of conversion to sesaminol was 90.2%. Suction filtration after cooling, the catalyst is washed twice with acetone, the washing liquid obtained twice is combined and the organic phase obtained by suction filtration is collected by preparative liquid chromatography at 295nm containing the sesaminol component, and the solvent is evaporated under reduced pressure. Obtained 0.22 g of yellow-brown...

Embodiment 2

[0023] A method for preparing sesamol by catalyzing sesamolin, specifically: take 80 mg (0.216 mmol) of pure sesamolin (purity: 98%) and 20 mL of ethylbenzene and add it to a 50 mL three-necked flask (the initial concentration of sesamolin is 10.8 mmol·L -1), stirred and preheated to 90°C, and then added 3 g of silicomomolybdenum heteropolyacid activated at 200°C for 3 h (13.89 g·mmol relative to the initial sesamolin -1 ), continuously stirred and kept at 90°C for 1.5h, and the reaction liquid was measured by HPLC for 1.5h, and the yield of conversion to sesaminol was 87.9%. Suction filtration after cooling, the catalyst was washed twice with ethyl acetate, the washings obtained twice were combined and together with the organic phase obtained by suction filtration, the solvent was evaporated under reduced pressure to obtain a yellow-brown paste solid, which was purified by silica gel column chromatography. N-hexane and ethyl acetate were eluted at a ratio of 5:1, detected by...

Embodiment 3

[0025] A method for preparing sesamol by catalyzing sesamolin, specifically: get 66 mg of sesamolin pure product (purity is 98%, 0.18mmol) and 10mL benzene and join in 25mL three-necked flask (sesamolin initial concentration is 18mmol. L -1 ), stirred and preheated to 70°C, then added phosphotungstic heteropolyacid cesium salt (Cs 2.5 h 0.5 PW 12 o 40 )0.72g (4 g·mmol relative to the initial sesamolin -1 ), continuously stirred and kept at 70°C for 4h, and the reaction solution at 4h was measured by HPLC, and the yield of conversion to sesaminol was 82.5%. Then, it was processed according to the method of Example 2 to obtain 43.5 mg of yellow-brown sesamol solid. The total sesamol content determined by HPLC was 98.2%, and the yield was 63.6%. Pure sesamolin 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 preparation of sesamol, and in particular relates to a method for preparing sesamol by using heteropolyacid (salt) or loaded heteropolyacid (salt) to catalyze sesamol. Background technique [0002] Sesamol, the molecular formula is C 20 h 18 o 7 , is one of the 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 sesamolin, its antioxidant capacity is the strongest, It is also the most stable. Sesamol not only has anti-oxidation properties, but also can be used as a natural antioxidant. It also has a wide range of biological activities. It can not only protect and strengthen liver function, regulate blood pressure, and lower cholesterol, but also directly act on tissues and organs to exert its excellent anti-inflammatory properties. oxidation capacity. [0003] [00...

Claims

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Application Information

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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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