Synthesis method of sterol ferulate

A technology of sterol ferulate and synthesis method, which is applied in the field of oleochemical industry, can solve the problems of separation of intermediate products, cumbersome reaction steps, and low conversion rate, and achieve the effects of less by-products, improved industrial production level, and low cost

Inactive Publication Date: 2021-03-26
江苏禾丰粮油工业有限公司 +1
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Problems solved by technology

Although the existing technology can successfully synthesize sterol ferulate, the existing method has the disadvantages of cumbersome reaction steps, separation of intermediate products, many by-products, low conversion rate, and the need for highly toxic reagents.

Method used

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preparation example Construction

[0015] A method for synthesizing ferulic acid sterol esters, comprising the following steps: respectively weighing a certain amount of ferulic acid / ferulic acid esters, phytosterols, catalysts, and reaction solvents, adding them to a round bottom flask, and fixing the oil bath heating device , start the stirring and adjust to the required temperature to start the reaction, stop the heating reaction after a period of time, and obtain the pure sterol ferulate through separation and purification.

[0016] In this embodiment, the catalysts are sodium dodecylbenzenesulfonate, copper dodecylbenzenesulfonate, zinc dodecylbenzenesulfonate, and magnesium dodecylbenzenesulfonate.

[0017] In this embodiment, the phytosterol is one of stigmasterol, β-sitosterol, brassicasterol and campesterol or a mixture of more than one in any proportion.

[0018] In the present embodiment, ferulic acid is a mixture of one or more of cis-ferulic acid and trans-ferulic acid in any proportion; the feruli...

Embodiment 1

[0024] Weigh 0.19g (1 mmol) of ferulic acid, 0.21g (0.5 mmol) of sitosterol, and 4% sodium dodecylbenzenesulfonate into a round bottom flask, add 10mL of tetrahydrofuran, and heat in an oil bath at 100oC for 2h. After the reaction was complete, samples of the toluene layer were collected by rotary evaporation. The collected samples were separated by silica gel column chromatography, and the eluent was petroleum ether (60~90oC) / ethyl acetate (4:1, v / v). After separation, 0.15g of pure product was obtained, and the pure product was used Based on the structural characterization analysis, the specific results are as follows.

[0025] FT-IR: The absorption peak at 2952 cm-1 is -CH3 stretching vibration absorption, the absorption peak at 2868 cm-1 is the stretching vibration absorption of -CH2, the bending vibration absorption at 1464 cm-1 is -CH3, and 1366 cm-1 It is the bending vibration absorption of -CH2, the strong absorption peak at 1732cm-1 is the stretching vibration absorp...

Embodiment 2

[0028] Add 0.33g phytosterols, 0.93g ferulic acid, and 2% magnesium dodecylbenzenesulfonate to a reflux reaction device equipped with stirring and oil bath temperature control, respectively, and add 10mL of N,N'-dimethylformaldehyde Amide, start stirring and adjust the temperature to 80°C, and react for 9h. The conversion rate of sterol ferulate can reach 90.3% as detected by HPLC. After the reaction was completed, the reaction sample was collected by rotary evaporation and separated by silica gel column chromatography to obtain 0.40 g sterol ferulate with a purity of 98%.

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Abstract

The invention relates to the technical field of grease chemical engineering, and discloses a synthesis method of sterol ferulate, which comprises the following steps: respectively weighing a certain amount of ferulic acid / ferulate, phytosterol, a catalyst and a reaction solvent, adding into a round-bottom flask, fixing an oil bath heating device, starting stirring, adjusting to the required temperature, starting reaction to obtain sterol ferulate, and after a period of time, stopping the heating reaction, and separating and purifying to obtain a pure product of the steryl ferulate. The methodis simple in process operation, only one-step esterification reaction is needed, intermediate product separation and purification are not needed, time consumption is short, byproducts are few, and energy consumption is low. The purity of the sterol ferulate prepared by the method can reach 97% or above, the yield can reach 84% or above, the reaction time is shorter than 10 h, the cost is low, industrial production is facilitated, and the method has important significance in improving the industrial production level of the sterol ferulate.

Description

technical field [0001] The invention relates to the technical field of oleochemical industry, in particular to a method for synthesizing sterol ferulate. Background technique [0002] Ferulic acid is a phenolic acid naturally occurring in plants, which can be extracted from rice bran, sugar cane, corn and other grains and their by-products. Ferulic acid is also one of the main components of traditional Chinese medicines such as Angelica, Chuanxiong, and Cimicifuga. Studies have shown that ferulic acid has many activities such as anti-oxidation, regulating blood lipids, promoting blood circulation and removing blood stasis, anti-thrombotic, anti-bacterial and anti-inflammatory, whitening, etc., and has broad application prospects in food, medicine, cosmetics and other industries. Among many biological activities, the antioxidant activity of ferulic acid has attracted much attention. In the body, ferulic acid has a strong scavenging effect on hydrogen peroxide, superoxide fr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/005
Inventor 何文森孙玉莹蔡兆海王艳崔凤杰施建成
Owner 江苏禾丰粮油工业有限公司
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