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A kind of preparation method of royal jelly acid

A technology of royal jelly acid and tetraalkylammonium bromide, which is applied in the field of preparation of royal jelly acid, can solve the problems of unstable Grignard reagent, high requirements for reaction conditions, and high production cost, achieve high selectivity and yield, and be easy to industrialize The effect of easy production and operation

Inactive Publication Date: 2021-05-25
JIAXING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The preparation process of this process is relatively simple, but the oxidation uses PCC, the oxidant cannot be recycled and reused and there is heavy metal pollution
[0006] Chinese patent application CN101747181A uses 1,1-dialkoxy-6-hexylmagnesium halide as raw material to obtain royal jelly acid through a four-step reaction. The Grignard reagent used in this process is unstable and requires high reaction conditions, so it is also Not suitable for industrial production
Although the route of this method is relatively simple and has the characteristics of high total yield, it needs to be catalyzed by ionic liquid, and the production cost is relatively high.

Method used

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  • A kind of preparation method of royal jelly acid
  • A kind of preparation method of royal jelly acid
  • A kind of preparation method of royal jelly acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Add 17.4 grams (0.1mol) of 1,10-decanediol, 74.1 grams (0.23mol) of tetrabutylammonium bromide, 141.4 grams (0.23mol) of Oxone and 200 milliliters of water in a 500mL single-necked bottle, and the mixture is heated to 80 degree, and reacted at this temperature for 6h. The reaction was carried out by TLC (the developing solvent was petroleum ether / ethyl acetate (volume ratio 1:2), R f = 0.4). After the reaction was completed, the reaction solution was cooled to about 0°C, the precipitated product was filtered and washed with water, and after drying, 24.0 g of white product II was obtained, with a yield of 96.3%.

[0027] 1 HNMR (CDCl 3 , δ (ppm), TMS): δ1.25-1.30 (m, 10H), 1.55 (m, 2H), 1.99-2.25 (m, 2H), 3.62 (t, 2H), 4.08 (t, 2H).

[0028] In a 250mL single-necked flask, add 12.5 grams (0.05mol) of the II compound prepared above, 40mL15wt% NaOH (0.15mol) ethanol solution, and stir at room temperature for 3h; Add concentrated hydrochloric acid drop by drop under ic...

Embodiment 2

[0031] Add 17.4 grams (0.1mol) of 1,10-decanediol, 35.4 grams (0.23mol) of tetramethylammonium bromide, 141.4 grams (0.23mol) of Oxone and 200 milliliters of water in a 500mL single-necked bottle, and heat the mixture to 80 degree, and reacted at this temperature for 7h. The reaction was carried out by TLC (the developing solvent was petroleum ether / ethyl acetate (volume ratio 1:2), R f = 0.4). After the reaction was completed, the reaction liquid was cooled to about 0°C, the precipitated product was filtered and washed with water, and after drying, 18.70 g of white product II was obtained, with a yield of 78.0%.

[0032] Add 12.5 grams (0.05mol) of compound II prepared above and 50mL of 15wt% NaOH (0.188mol) ethanol solution in a 250mL single-necked flask, stir and react at room temperature for 2.5h; Add concentrated hydrochloric acid drop by drop in an ice bath to adjust the pH of the solution to 3-4, put it in the refrigerator overnight to crystallize, filter to obtain the ...

Embodiment 3

[0034] Add 17.4 grams (0.1mol) of 1,10-decanediol, 151.6 grams (0.23mol) of tetra-n-decylammonium bromide, 141.4 grams (0.23mol) of Oxone and 200 milliliters of water in a 500mL single-necked bottle, and the mixture is heated to 80 degrees, and react at this temperature for 10h. The reaction was carried out by TLC detection (developing solvent was petroleum ether / ethyl acetate (volume ratio 1:2),

[0035] R f = 0.4). After the reaction was completed, the reaction solution was cooled to about 0°C, the precipitated product was filtered and washed with water, and after drying, 20.5 g of white product II was obtained, with a yield of 82.4%.

[0036] The steps of preparing royal jelly acid by hydrolysis, elimination and acidification of compound II are the same as in Example 1.

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Abstract

The invention discloses a preparation method of royal jelly acid, which belongs to the field of chemical synthesis. The present invention uses 1,10-decanediol as a raw material in water as a solvent, under the action of potassium persulfate and tetraalkylammonium bromide, to obtain 2-bromodecalactone (II) compound, and the reaction adopts a one-pot Oxidation, lactonization and α-H bromination three-step reaction take place respectively, have higher selectivity and yield; II then carry out hydrolysis and elimination reaction, obtain royal jelly acid target product after final acidification, and the crude product purity can reach 95%, reaching higher than 99% after recrystallization. The invention adopts two steps to prepare royal jelly acid, and the technical route has the characteristics of short route, simple operation and easy industrial production, and is a very economical and convenient method for synthesizing royal jelly acid.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and more specifically relates to a preparation method of royal jelly acid. Background technique [0002] Royal jelly acid is the main organic component of royal jelly, and its content is one of the main indicators to measure the quality of royal jelly. Its chemical name is (E)-10-hydroxy-2-decenoic acid, or 10-HDA for short. Because of its anti-bacterial, anti-cancer, anti-radiation and strong body and other physiological functions, it has attracted the attention of workers in the fields of chemistry, biology and medicine. At present, royal jelly and its products have become best-selling products in domestic and foreign markets. Although royal jelly acid can be extracted from royal jelly, the product prepared by synthetic method has high purity and quality is easier to guarantee. There are many synthetic routes published at home and abroad, but from a practical point of view, many routes are ei...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C51/02C07C59/42C07C51/347C07D313/00
Inventor 李梦宗乾收刘雪君汪露戴晶晶张雅晶郑滟男周宏伟包琳
Owner JIAXING UNIV
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