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Coenzyme Q10 synthesizing process

A technology of coenzyme and hydroquinone, which is applied in the field of synthesizing coenzyme Q10, can solve the problems of unfavorable industrial production, harsh reaction conditions, and no yield, and achieve the effects of safe and controllable production process, mild reaction conditions, and easy operation

Inactive Publication Date: 2007-03-21
KUNMING TONGFA IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] In 2002, the patent US 2002 / 0156302 A1 of Daniel Dacvid West in the United States provided a coenzyme Q 0 Preparation of Coenzyme Q by the Reaction of Hydroquinone and Isodecadecaprenyl Alcohol 10 method, the reaction was carried out in n-hexane at 43°C, and finally coenzyme Q was obtained by silica gel chromatography 10 , but there is no description of the yield and other aspects in this method
[0014] The publication number US 2006 / 0167289 A1 invented by Bruce H. Lipshutz et al. in 2006 provides a high-yield synthetic coenzyme Q 10 method, the synthesis yield is 68%, but the method needs to be carried out at -78°C, the reaction conditions are too harsh, the reagents are expensive, flammable and explosive, which is not conducive to industrial production
[0015] In summary, the above coenzyme Q 10 There are many defects in the preparation method, the yield is not high, the price of the reagent is expensive, the reaction conditions are harsh, the synthetic route is loaded down with trivial details etc.

Method used

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  • Coenzyme Q10 synthesizing process
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  • Coenzyme Q10 synthesizing process

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 30g coenzyme Q 0 Mix hydroquinone with 160ml of dry toluene, replace the air with nitrogen, heat and reflux in nitrogen atmosphere, and remove coenzyme Q through a water separator 0 Moisture contained in hydroquinone, finally evaporate toluene to dryness under reduced pressure, monitor moisture, coenzyme Q with moisture 0 Hydroquinone was stored under dry nitrogen for later use.

[0043] Mix 50g of isodecadecaprenyl alcohol with 330ml of toluene, and use a similar method to reflux under reduced pressure to separate and remove the moisture in the isodecadecaprenyl alcohol. Prenyl Alcohol is set aside.

Embodiment 2

[0045] Take the prepared coenzyme Q 0 Hydroquinone 3.68g (0.02mmol) and content are the isodecadecaprenyl alcohol 17.95g (0.025mmol) of 97.2%, join in the 100ml there-necked flask that is filled with nitrogen, add 12ml dichloromethane and 40ml of cyclopentane was stirred to dissolve all the raw materials, cerium trifluoromethanesulfonate with 1% isodecadecaprenyl alcohol was added to catalyze the reaction, the reaction was monitored by TLC, and the reaction was carried out at room temperature for 80 minutes. After the reaction is complete, add the reaction liquid into 50 ml of an oxidizing agent composed of hydrogen peroxide and ferric chloride solution, stir, monitor the reaction by TLC, and react at room temperature for 1 hour. Transfer to a separatory funnel for static layering, release the oxidant in the lower layer, wash the upper organic layer once with 20ml saturated brine, discard the brine layer, add 5g of anhydrous magnesium sulfate and dry for 2 hours, recover the s...

Embodiment 3

[0048] Take the dehydrated coenzyme Q 0 Hydroquinone 4.6g (0.025mmol) and content are 17.95g (0.025mmol) of isodecadecaprenyl alcohol of 97.2%, join in the 100ml there-necked bottle that is filled with nitrogen, add 8ml chloroform and 40ml n-hexyl in the bottle alkane, stirring to dissolve all the raw materials, adding hafnium trifluoromethanesulfonate with a molar weight of 3% isodecadecaprenyl alcohol to catalyze the reaction, monitoring the reaction by TLC, and reacting at room temperature for 120 minutes. After the reaction is complete, add the reaction solution into 60 ml of an oxidizing agent composed of hydrogen peroxide and ferric chloride solution, stir, monitor the reaction by TLC, and react at room temperature for 1.5 hours. Transfer to a separatory funnel for static layering, release the oxidant in the lower layer, wash the upper organic layer once with 20ml of saturated brine, discard the brine layer, add 5g of anhydrous magnesium sulfate to dry for 2 hours, recov...

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Abstract

The coenzyme Q10 synthesizing process with coenzyme Q0 hydroquinone and isodecyl alcohol deca-isopentyl alcohol of purity not lower than 95 % as material includes dewatering and condensation reaction at room temperature under the catalysis of trifluoro methane sulfonic acid in no oxygen environment to obtain coenzyme Q10 hydroquinone, the oxidation of the reacted product without passing through any treatment with hydrogen peroxide and water solution of ferric trichloride to obtain crude coenzyme Q10 product, and crystallization of the crude coenzyme Q10 product in acetone to obtain yellow coenzyme Q10 product powder in content over 99 % and yield over 65 %. The present invention has simple operation, easy purification of the product, high yield, mild reaction condition, safe and controllable production process and industrial production value.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry. Specifically related to a synthetic coenzyme Q 10 Methods. Background technique [0002] coenzyme Q 10 (Coenzyme Q 10 , abbreviated as CoQ 10 ), also known as decenoquinone, ubiquinone-10 (Ubiquinone-10), is a natural product that exists in many animal and plant tissues, especially in the mitochondria-rich biofilm of mammals, in human heart, liver , kidney and pancreas, which were isolated from bovine heart by Crane P.L. in 1957, and its structure was identified in 1958 as: 2,3-dimethoxy-5-methyl-6-decyl isoprenyl-1 , 4-benzoquinone (2,3-dimethoxy-5-methyl-6-decaprenyl-1,4-benzoquinone). [0003] Numerous studies have shown that coenzyme Q 10 It is fat-soluble and has the characteristics of common vitamins, and its chemical structure is similar to vitamin K. It plays an important role in mitochondrial electron transfer in biofilm, participates in protein and fat metabolism, is...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C50/28C07C46/06
Inventor 王国平申醒朱锡英符涛
Owner KUNMING TONGFA IND
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