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Synthetic method of paradol

A synthetic method, the technology of zingerol, applied in the field of drug synthesis, can solve the problems of unfavorable large-scale industrial production, incomplete reaction of raw materials, production of large by-products, etc., achieve short reaction time, improve purity and yield, and simple steps Effect

Inactive Publication Date: 2014-02-05
SUZHOU UUGENE BIOPHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although both of these two patent documents have produced gingerol, there are problems in the synthesis process: one, the first step of condensation reaction using vanillin and 2-nonanone will cause some raw materials to react incompletely, resulting in raw materials The conversion rate is low, and sodium bisulfite needs to be added to remove unreacted vanillin during post-reaction treatment; 2. In the second step of hydrogenation reduction, ethanol is selected as the solvent. In the reaction, not only the ethylenic bond will be reduced, but also the molecular The reduction of the ketone group produces a large number of by-products and reduces the yield of the product; the third and second steps of the reaction require column chromatography purification, which is cumbersome to handle and has a low total yield of only 52.2%, which is not conducive to large-scale industrial production

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 50g of 4-bromo-2-methoxyphenol and 38g of 1-undecen-3-one to the reaction flask in turn and dissolve them in 500mL of acetonitrile to form a reaction solution. Stir until the raw materials are completely dissolved, then add 50g of triethylamine and 19.4g of triphenyl base phosphorus, 1.66g of palladium acetate, after the addition, replace the air in the reaction bottle with nitrogen, raise the temperature of the reaction solution to 60°C and stir for 10 hours until the reaction is complete, condense the complete reaction solution to dryness, and then add 500mL of ethyl acetate and 100mL saturated aqueous sodium bicarbonate solution, stirred until completely dissolved, then separated to obtain an organic phase, dried and concentrated to obtain 60g of 1-(4-hydroxy-3-methoxyphenyl)undecen-3-one;

[0031] Dissolve 60g of 1-(4-hydroxy-3-methoxyphenyl)undecen-3-one prepared above in 300mL ether to form a reaction solution, stir until completely dissolved, add 6g of palladi...

Embodiment 2

[0033] Add 60g of 4-bromo-2-methoxyphenol and 45.6g of 1-undecen-3-one as raw materials to the reaction bottle and dissolve them in 600mL of dioxane to form a reaction solution. Stir until the raw materials are completely dissolved, then add 40g of imidazole and 10.2g of Tetrakis(triphenylphosphine)palladium, replace the air in the reaction bottle with nitrogen after the addition, raise the temperature of the reaction solution to 50°C and stir for 8 hours until the reaction is complete, concentrate the reaction solution to dryness and add 500mL of isopropyl acetate ester and 120mL saturated aqueous sodium bicarbonate solution, stirred until completely dissolved, and separated to obtain an organic phase, which was dried and concentrated to obtain 71g of 1-(4-hydroxy-3-methoxyphenyl)undecen-3-one;

[0034] Dissolve 71g of 1-(4-hydroxy-3-methoxyphenyl)undecen-3-one prepared above in 350mL isopropyl ether to form a reaction solution, stir until completely dissolved, then add 6.5g o...

Embodiment 3

[0036] Add raw materials 70g of 4-bromo-2-methoxyphenol and 53.2g of 1-undecen-3-one to the reaction flask and dissolve them in 700mL N,N-dimethylformamide to form a reaction solution, stir until the raw materials are completely dissolved, then add 54.5 g pyridine, 27.5 g diphenylcyclohexylphosphine, 2.5 g palladium acetate, after the addition, replace the air in the reaction flask with nitrogen, raise the temperature of the reaction solution to 55 ° C and stir for 9 hours until the reaction is complete, and the complete reaction solution After concentrating to dryness, add 700mL isopropyl acetate and 150mL saturated aqueous sodium bicarbonate solution, stir until completely dissolved, then separate to obtain an organic phase, dry the organic phase, and concentrate to obtain 76g of 1-(4-hydroxy-3-methoxyphenyl)dec One en-3-one;

[0037] Dissolve 76g of 1-(4-hydroxy-3-methoxyphenyl)undecen-3-one prepared above in 400mL of diethyl ether to form a reaction solution, stir until comp...

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Abstract

The invention relates to a synthetic method of paradol. The synthetic method comprises the following steps: firstly sequentially dissolving raw materials, namely 4-bromine-2-methoxyphenol and 1-hendecene-3-ketone into a solvent to form a reaction liquid; stirring till the raw materials are all dissolved, and then adding organic alkali and a catalyst; then displacing air by using nitrogen; heating the reaction liquid to 50-70 DEG C, stirring for 8-12 hours till the reaction is complete, and carrying out post processing to obtain 1-(4-hydroxy-3-methoxyphenyl)hendecene-3-ketone; then dissolving the 1-(4-hydroxy-3-methoxyphenyl)hendecene-3-ketone into the solvent, stirring till the 1-(4-hydroxy-3-methoxyphenyl)hendecene-3-ketone is all dissolved, and then adding the catalyst; stirring at the atmosphere (normal pressure) of hydrogen at room temperature overnight, and finally carrying out post processing to obtain the product paradol. The synthetic method disclosed by the invention has the advantages of simple step, moderate reaction condition and short time, can obtain the intermediate product and the end product by directly using a next-step reaction or through recrystallization without purifying through column chromatography, increases the purity, yield and production efficiency of products and is suitable for industrialized production.

Description

technical field [0001] The invention relates to a method for synthesizing zingerol, which belongs to the technical field of drug synthesis. Background technique [0002] Zingerol, its chemical name: 1-(4-hydroxy-3-methoxyphenyl)-3-decanone, molecular formula C 17 h 26 o 3 , CAS registry number: 277113-22-0. On the one hand, zingerol can improve the wrinkles of the skin (especially the exposed part of the skin) with aging, so zingerol can be used as a wrinkle improving agent to keep the skin in a so-called healthy state in dermatology and cosmetics, and cooperate with it The external skin composition of this wrinkle improving agent. On the other hand, zingerol can promote the reduction of systemic or local adipose tissue, thereby improving obesity. Therefore, zingerol can be used as a skin external composition that can effectively inhibit or prevent obesity or a food additive added to food. The structural formula of zingerol is as follows: [0003] [0004] The docum...

Claims

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Application Information

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IPC IPC(8): C07C45/62C07C49/255
CPCC07C45/62C07C45/68C07C49/255
Inventor 李志强储成钢贺世杰王伸勇王晓俊胡隽恺
Owner SUZHOU UUGENE BIOPHARMA