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Method for synthesizing alliin with optical activity and reaction device thereof

A synthetic method and optically active technology, applied in chemical instruments and methods, organic chemistry, preparation of organic compounds, etc., can solve the problems of shortage of bromine resources, difficult separation, high reactivity, etc., to improve body immunity, promote blood The effect of circulation and high product yield

Inactive Publication Date: 2014-01-01
JINAN UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is simple and convenient, with low cost and high efficiency, but there are also the following problems: 1) the obtained product is a racemate; 2) the reactivity of allyl bromide is relatively large, and it is easy to generate by-products such as allyl alcohol, Cause separation difficulties; 3) The sodium bromide produced by the reaction and the sodium chloride produced in the separation process are difficult to separate, resulting in waste of resources, etc.; 4) Bromine resources are relatively short, and the price of allyl bromide is relatively high

Method used

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  • Method for synthesizing alliin with optical activity and reaction device thereof
  • Method for synthesizing alliin with optical activity and reaction device thereof

Examples

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Embodiment 1

[0035]Step 1, first cool the closed reactor 1 with an ice bath until the temperature is 0°C, open the feed valve 6, close the circulation valve 5, and feed nitrogen into the closed reactor 1 from the feed pipe 7 at a flow rate of 1.0 L / min , then add 100 milliliters of 1mol / L cysteine ​​aqueous solution (containing 12.1 grams of cysteine) to it, close the feed valve 6, then open the circulation valve 5, and stir for 5 minutes with the stirring paddle 2 at a speed of 500 rpm; when the temperature of closed reactor 1 is controlled within 10°C, add 110 ml of 1mol / L NaOH solution and continue stirring (500 rpm) until all cysteine ​​is dissolved, then add 0.12 mol of allyl chloride (about 9.2 grams), reacted at this temperature for 2.5 hours to obtain a deoxyalliin aqueous solution, and then stirred at room temperature for 1 hour at a speed of 500 rpm; then extracted three times with ethyl acetate (each 200mL each time), the extracted aqueous solution was vacuum concentrated at 60°...

Embodiment 2

[0040] Step 1, when cooling the reactor with an ice bath until the temperature is 5°C, feed nitrogen into the reactor with a flow rate of 0.5L / min, and then add 50 ml of 1mol / L cysteine ​​aqueous solution (containing cysteine amino acid 6.0 g), and turn on the stirrer for 3 minutes, the stirring speed is 400 rpm, and the temperature of the reactor is controlled within 10°C, then add 55 ml of 1mol / L NaOH solution, and continue to stir (400 rpm / min) until the cysteine ​​is completely dissolved, then add 0.06mol of allyl chloride, react at this temperature for 2.5 hours to obtain a deoxyalliin aqueous solution, and then stir for 1 hour at room temperature, with a speed of 400 rpm ; Then extract three times with ethyl acetate (200mL each time), concentrate the extracted aqueous solution to one-third of the original volume by vacuum at 60°C, and adjust the pH value to 5.5 with hydrochloric acid after the concentrated solution is cooled to room temperature. Stand still for 12 hours...

Embodiment 3

[0044] Step 1, when cooling the reactor with an ice bath until the temperature is 5°C, feed nitrogen into the reactor with a flow rate of 10 L / min, and then add 10 milliliters of 1mol / L cysteine ​​aqueous solution (containing cysteine acid 1.2 g), stirred for 3 minutes, the rotation speed was 500 rpm, and when the temperature of the reactor was controlled within 10°C, 0.8 ml of 17mol / L ammonia solution was added, and the stirring was continued until the cysteine ​​was completely dissolved. The number of rotations is 500 rpm, then add 0.01mol of allyl chloride (1.0 g), and react at this temperature for 2.0 hours to obtain a deoxyalliin aqueous solution, then stir at room temperature for 1 hour, and the number of rotations is 500 rpm ; Then extract three times with petroleum ether (10 mL each time), concentrate the extracted aqueous solution to one-third of the volume of the original solution in vacuum at 80 ° C, and adjust the pH value to 5.5 with hydrochloric acid after the con...

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Abstract

The invention discloses a method for synthesizing alliin with the optical activity and a reaction device thereof. The method for synthesizing the alliin comprises the following steps: adding a sulfo-aminolactic acid aqueous solution, alkali and allyl chloride in a reactor under the stirring situation, conducting the stirring reaction for 0.5-3 hours at the temperature of -5-10 DEG C, obtaining a deoxidized alliin aqueous solution, after the complete reaction, continuously conducting stirring for 1-3 hours, conducting vacuum concentration on the aqueous solution, adjusting the pH value to be 5.2-5.5 by the acid, conducting standing and sedimentation, obtaining a deoxidized alliin product, manufacturing the deoxidized alliin product to be the aqueous solution, then adding the aqueous solution into the reactor, then adding hydrogen peroxide, conducting the stirring reaction for 5-20 hours at the temperature of -5-10 DEG C, then conducting the vacuum concentration on reaction liquid until the reaction liquid is dried, obtaining an alliin crude product, dissolving the alliin crude product into the mixed solvent, conducting crystallization, then filtering, taking the crystalline solid, and obtaining the alliin with the optical activity synthesized in the method. The method is easy to operate, higher in product yield and suitable for industrial production.

Description

technical field [0001] The invention belongs to the field of chemical synthesis and preparation, and in particular relates to a method for synthesizing optically active alliin and a reaction device thereof. Background technique [0002] Alliin is a substance found and extracted from garlic, which has a wide range of biological activities: it has a strong killing effect on common pathogenic bacteria such as Staphylococcus aureus, Mycobacterium tuberculosis, and Neisseria meningitidis It also has significant curative effects on microbial infectious diseases such as insect diseases; in addition, it also has good effects on reducing blood fat, improving human immunity, anti-aging, anti-cancer and anti-cancer. At present, alliin health care products are mainly used in the prevention of myocardial infarction, cerebral infarction and blood fat reduction abroad. In view of the excellent efficacy of alliin in the prevention and treatment of cardiovascular and cerebrovascular disease...

Claims

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Application Information

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IPC IPC(8): C07C317/48C07C315/02C07C323/58C07C319/14
Inventor 周华周美云欧仕益吴建中
Owner JINAN UNIVERSITY
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