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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: 2013-04-17
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, then 100 g of silica (100 mesh) was added to the solution, stirred, and then the solvent was concentrated Removed to obtain 1,8-octanediol adsorbed on silica.

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

Embodiment 2

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

[0048] 1,8-octanediol (10 g, FW: 146.22; 68.40 mmol) was dissolved in 100 ml of ether, then 50 g of silicon dioxide (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 1000mL three-necked round-bottomed flask equipped with a mechanical stirrer, a thermometer, and a constant pressure dropping funnel, the above-mentioned adsorbate, 500ml of petroleum ether, and acetyl chloride (10.74g, FW: 78.50; 136.81mmol) were sequentially added to the system . The reaction was then stirred for 12 hours at 20°C. After the completion of the reaction, the temperature of the system was cooled to room temperature, and then the mixture was filtered, and the filter cake was fully washed with ethyl acetate until there was no product in the filter cake. A colorless filtrate was obtained, the organic phases were combined and the...

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, then 100 g of silicon dioxide (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 1000mL three-neck round-bottomed flask equipped with mechanical stirring, a thermometer, and a constant pressure dropping funnel, the above-mentioned adsorbate, 500ml of petroleum ether, and propionyl chloride (12.66g, FW: 92.52; 136.81mmol) were added to the system in sequence. middle. The reaction was then stirred for 4 hours at 60°C. After the completion of the reaction, the temperature of the system was cooled to room temperature, and then the mixture was filtered, and the filter cake was fully washed with ethyl acetate until there was no product in the filter cake. A colorless filtrate was obtained, the organic phases were combi...

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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 synthesis 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-quinenoic acid, its English name is trans-10-hydroxy-2-decenoic acid, referred to 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 immune function of the body, strongly inhibit lymphoma, breast cancer and other cancer cells, and can treat acute radiation damage and chemical substances. It is good for high blood pressure, low blood pressure, anemia, vascular circulation disorder, arteriosclerosis, neurasthenia, allergic diseases of bronchial wheezing, poor physical strength, lack of energy, loss of thinking and memory, insomnia, headache, irritability and low libido, etc. healing effect. In...

Claims

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Application Information

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