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Synthetic method of effective component-royaljelly acid of royal jelly

A technology of effective components and synthesis methods, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of low coupling reaction yield, limited use, cumbersome synthesis routes, etc., to avoid difficulties in product purification , high yield and mild reaction conditions

Inactive Publication Date: 2010-06-23
邵阳市科瑞化学品有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis route of this method is cumbersome, and the yield of the key step coupling reaction is also low, which limits its use in industrial production

Method used

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  • Synthetic method of effective component-royaljelly acid of royal jelly
  • Synthetic method of effective component-royaljelly acid of royal jelly
  • Synthetic method of effective component-royaljelly acid of royal jelly

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of 8-acetoxyoctanal:

[0037] Add bromoethanol acetate (70.3mmol), N-methyl-2-pyrrolidone (27.88g, 0.281 mol, 4 equivalents based on bromoethanol acetate), 30 mL of anhydrous tetrahydrofuran, then the temperature of the system was lowered to -10 ° C, cuprous iodide (2.11 mmol, 3 equiv%), and then 1,1-ethylenedioxy -6-Hexylmagnesium bromide (1.1 equivalents based on bromoethanol acetate) was transferred to a constant pressure dropping funnel.

[0038] Slowly add 1,1-ethylenedioxy-6-hexylmagnesium bromide dropwise to the system, stir vigorously, keep the temperature of the system at -10°C, and the dropwise addition is completed in about 1 hour. After the dropwise addition, the system was kept at -10°C for 0.5h. After the reaction was completed, 10 mL of saturated ammonium chloride aqueous solution was added dropwise to the system, and then 2M hydrochloric acid was added to the system to adjust the pH to 4-5. The system continued to stir for 24 hours. Most o...

Embodiment 2

[0042] Preparation of 8-propionyloxyoctanal

[0043]Add bromoethanol propionate (70.3mmol), N-methyl-2-pyrrolidone (27.88g, 0.281 mol, 4 equivalents based on bromoethanol propionate), 30 mL of anhydrous tetrahydrofuran, then the temperature of the system was lowered to -50 °C, cuprous chloride (4.22 mmol, 6 equiv%), and then 1,1-dimethoxy -6-hexylmagnesium chloride (1.1 equivalents based on bromoethanol propionate) was transferred to a constant pressure dropping funnel. Slowly add 1,1-dimethoxy-6-hexylmagnesium chloride dropwise to the system, stir vigorously, keep the temperature of the system at -50°C, and the dropwise addition is completed in about 1 hour. After the dropwise addition, the system was kept at -50° C. for 0.5 h. After the reaction was completed, 10 mL of saturated ammonium chloride aqueous solution was added dropwise to the system, and then 10% phosphoric acid was added to the system to adjust the pH value to 4-5. The system continued to stir for 24 hours. ...

Embodiment 3

[0046] Preparation of 8-Acetoxyoctanal

[0047] Add bromoethanol propionate (70.3mmol), N-methyl-2-pyrrolidone (0.352mol, based on 5 equivalents of bromoethanol propionate), 30mL of anhydrous tetrahydrofuran, then the temperature of the system was raised to 50°C, Li 2 CuCl 4 (4.22mmol, 6mol%), and then its 1,1-dimethoxy-6-hexylmagnesium bromide (1.1 equivalents based on bromoethanol propionate) was transferred to a constant pressure dropping funnel. Slowly add 1,1-diethoxy-6-hexylmagnesium bromide dropwise to the system, stir vigorously, keep the temperature of the system at 50°C, and the dropwise addition is completed in about 1 hour. After the dropwise addition, the system was kept at 50° C. for 0.5 h. After the reaction was completed, 10 mL of saturated ammonium chloride aqueous solution was added dropwise to the system, and then 0.5 g of p-toluenesulfonic acid was added to the system. The system continued to stir for 24 hours. Most of the tetrahydrofuran was then disti...

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Abstract

The invention provides a synthetic method of an effective component-royaljelly acid of royal jelly, comprising the following steps: allowing (1,1-bialkoxy-6-hexyl magnesiumhalide) to react with bromoethanol alkyl acid ester in the solvent in the presence of an auxiliary agent N-methyl-2-pyrrolidone under catalysis of catalytic amount of a copper catalyst; removing acetal protection under acid conditions to obtain 8-alkyl acyloxy caprylicaldehyde; and then adopting Knoevenagel condensation method to obtain the royaljelly acid in formula (1). The method adopted by the invention is characterized by mild reaction conditions, simple operation ('one pot method'), high yield and the like, and avoids the problems of difficult purification, low yield and the like encountered by the traditional synthetic technology of the compound, thus greatly reducing production cost. The reagent used in the whole reaction is available, thus being convenient for industrial implementation.

Description

technical field [0001] The invention relates to a method for preparing royal jelly acid. Background technique [0002] Royal jelly acid, also known as royal jelly acid, its chemical name is trans-10-hydroxy-2-decenoic acid, the English name is trans-10-hydroxy-2-decenoic acid, referred to as 10-HAD, which is a unique component of royal jelly, and It is one of the main active ingredients of royal jelly. It can enhance the immune function of the body, strongly inhibit various cancer cells such as lymphoma and breast cancer, and can treat acute radiation damage and chemical damage at the same time. In view of the medical effect of royal jelly acid and its unique characteristics of royal jelly, the content of royal jelly acid has been used as the main index to measure the quality of royal jelly. [0003] Now royal jelly acid is mainly obtained through two ways, one is extraction from royal jelly, and the other is chemical synthesis. Because the method for extracting royal jel...

Claims

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Application Information

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IPC IPC(8): C07C59/42C07C51/353C07C51/347
Inventor 左前进羊向新刘喜荣
Owner 邵阳市科瑞化学品有限公司
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