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Synthetic method of royaljelly acid

A synthesis method and a royal jelly acid technology, applied in the field of medicine, can solve the problems of poor selectivity, difficult product purification, increased side reactions, etc., and achieve the effects of high stereoselectivity, serious environmental pollution, and improved stereoselectivity

Active Publication Date: 2011-10-05
上海灏翔生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There are following problems in this route: 1,8-octanediol monobromination selectivity is relatively poor, easily obtains 1,8-dibromooctane, and this material is not easy to separate with 1,8-octanediol and causes back-step reaction side reaction At the same time, it is not easy to obtain anhydrous trimethylamine oxide industrial products, because commercially available trimethylamine oxide has two crystal waters, and anhydrous trimethylamine oxide needs to be processed more tediously
Because 8-hydroxyoctanal is not conducive to preservation, it will bring many troubles to industrialized production
At the same time, the double bond configuration of royal jelly acid is (E) formula, and there will be the problem that the isomer is (Z) formula through Wittig-Horner reaction or Knoevenagel reaction, which makes the purification of the product difficult and cannot obtain the pure target product.

Method used

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  • Synthetic method of royaljelly acid
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  • Synthetic method of royaljelly acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of 8-acetoxy-1-octanol (3)

[0044] 1,8-octanediol (10.00 g, FW: 146.22; 68.40 mmol) was dissolved in 100 ml of ethyl acetate, and then 100 g of silica (100 mesh) was added to the solution, stirred, and then the solvent was concentrated Removal, to obtain 1,8-octanediol adsorbed on the silica.

[0045] At the same time, in a 1000mL three-necked round bottom flask equipped with mechanical stirring, thermometer and constant pressure dropping funnel, the above adsorbent, 500ml cyclohexane and acetyl chloride (6.44g, FW: 78.50; 82.10mmol) were added to the system in sequence in. The reaction temperature was then raised to 60°C, and stirring was continued at this reaction temperature for 2 hours. After the reaction was completed, the temperature of the system was cooled to room temperature, and then the mixture was filtered, and the filter cake was washed thoroughly with ethyl acetate until the filter cake had no product. A colorless filtrate is obtained, the organ...

Embodiment 2

[0047] Preparation of 8-acetoxy-1-octanol (3)

[0048] 1,8-octanediol (10g, FW: 146.22; 68.40mmol) was dissolved in 100 ml of ether, and then 50 g of silica (100 mesh) was added to the solution, stirred, and then the solvent was concentrated and removed to obtain 1,8-octanediol is adsorbed on silica.

[0049] At the same time, in a 1000 mL three-necked round bottom flask equipped with mechanical stirring, thermometer, and constant pressure dropping funnel, the above-mentioned adsorbent, 500 ml of petroleum ether, and acetyl chloride (10.74g, FW: 78.50; 136.81mmol) were sequentially added to the system. . The reaction was then stirred at 20°C for 12 hours. After the reaction was completed, the temperature of the system was cooled to room temperature, and then the mixture was filtered, and the filter cake was washed thoroughly with ethyl acetate until the filter cake had no product. A colorless filtrate is obtained, the organic phases are combined and the filtrate is distilled und...

Embodiment 3

[0051] Preparation of 8-propionyloxy-1-octanol (3)

[0052] 1,8-octanediol (10g, FW: 146.22; 68.40mmol) was dissolved in 100 ml of ether, and then 100 g of silica (100 mesh) was added to the solution, stirred, and then the solvent was concentrated and removed to obtain 1 , 8-octanediol is adsorbed on silica.

[0053] At the same time, in a 1000 mL three-necked round bottom flask equipped with mechanical stirring, thermometer, and constant pressure dropping funnel, the above adsorbent, 500 ml petroleum ether, and propionyl chloride (12.66g, FW: 92.52; 136.81mmol) were added to the system in sequence in. The reaction was then continued to stir at 60°C for 4 hours. After the reaction was completed, the temperature of the system was cooled to room temperature, and then the mixture was filtered, and the filter cake was washed thoroughly with ethyl acetate until the filter cake had no product. A colorless filtrate is obtained, the organic phases are combined and the filtrate is distil...

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Abstract

The invention discloses a synthetic method of royaljelly acid, comprising steps of: firstly, performing a reaction between 8-alkanoyloxy octanal (4) and monoethyl malonate in the presence of DMAP in a solvent, and collecting (E)-10-alkanoyloxy-2-decenoic acid alkyl ester (5) from the reaction product; secondly, performing a saponification reaction of (E)-10-alkanoyloxy-2-decenoic acid alkyl ester(5) in an aqueous solution of alkaline materials, and collecting the target product royaljelly acid from the saponification product. According to the invention, the synthesis of royaljelly acid is designed again, avoiding problems of difficult product purification and low yield in traditional synthesis technology of the compound and greatly reducing production cost. Any other method can not accomplish the result in the invention. According to the invention, reagents used in the whole reaction are all easily available. The process route provided by the invention is of great innovation and convenient for industrial enforcement.

Description

Technical field [0001] The invention belongs to the technical field of medicine and relates to a novel synthetic method for preparing royal jelly acid. Background technique [0002] Royal jelly acid is also known as royal acid, its chemical name is trans-10-hydroxy-2-decenoic acid, and its English name is trans-10-hydroxy-2-decenoic acid, abbreviated as 10-HAD. Its structural formula is as follows: [0003] [0004] As a naturally occurring compound, royal jelly acid is unique to royal jelly. It can enhance the body's immune function, strongly inhibit lymphoma, breast cancer and other cancer cells, and can also treat acute radiation damage and chemical substances. Good for hypertension, hypotension, anemia, vascular circulation disorders, arteriosclerosis, neurasthenia, bronchial wheezing allergic diseases, poor physical strength, lack of energy, loss of thinking and memory, insomnia, headaches, irritability, and low libido. The healing effect. In view of the high pharmacological...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C51/377C07C59/42
Inventor 严政军金燕华
Owner 上海灏翔生物科技有限公司
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