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

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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 sepa

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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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Example Embodiment

[0034] Example 1:

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

Example Embodiment

[0039] Example 2:

[0040] Step 1, first use an ice bath to cool the reactor to a temperature of 5°C, then pour nitrogen into the reactor at a flow rate of 0.5L / min, and then add 50ml of 1mol / L cysteine ​​aqueous solution (containing cysteine 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 ℃, then add 55 ml of 1mol / L NaOH solution, continue to stir (400 rpm / Min) After the cysteine ​​is completely dissolved, add 0.06mol of allyl chloride, react at this temperature for 2.5 hours to obtain a deoxy alliin aqueous solution, and then stir at room temperature for 1 hour at 400 rpm ; Then it was extracted three times with ethyl acetate (200mL each time), the extracted aqueous solution was vacuum concentrated at 60°C to one-third of the original volume, the concentrated solution was cooled to room temperature and the pH was adjusted to 5.5 with hydrochloric acid. Let stand for 12 hours, precipi...

Example Embodiment

[0043] Example 3:

[0044] Step 1, first use an ice bath to cool the reactor to a temperature of 5°C, then pour nitrogen into the reactor at a flow rate of 10L / min, and then add 10ml of 1mol / L cysteine ​​aqueous solution (containing cysteine Acid 1.2g), stir for 3 minutes, the speed is 500 rpm, the temperature of the reactor is controlled within 10 ℃, then add 0.8 ml of 17mol / L ammonia solution, continue to stir until all cysteine ​​is dissolved, The rotation speed is 500 rpm, then 0.01 mol of allyl chloride (1.0 g) is added, and the reaction is at this temperature for 2.0 hours to obtain a deoxy alliin aqueous solution, and then stirred at room temperature for 1 hour, the rotation speed is 500 rpm ; Then extracted three times with petroleum ether (10mL each time), the extracted aqueous solution was vacuum concentrated at 80 ℃ one third of the original solution volume, the concentrated solution was cooled to room temperature and adjusted the pH value to 5.5 with hydrochloric acid...

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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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