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Method for preparing astaxanthin by oxidizing canthaxanthin

A technology of canthaxanthin and astaxanthin, applied in the direction of organic chemistry, can solve the problems of high price, high risk, and easy decomposition of n-butyl lithium, and achieve increased production safety, short process route, and less reaction materials Effect

Active Publication Date: 2020-10-09
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage of this route is that the price of the important reagent n-butyllithium used is high, and there are safety hazards that are easy to catch fire and easily decompose during use, which makes this route have the disadvantages of high cost and high risk.

Method used

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  • Method for preparing astaxanthin by oxidizing canthaxanthin
  • Method for preparing astaxanthin by oxidizing canthaxanthin
  • Method for preparing astaxanthin by oxidizing canthaxanthin

Examples

Experimental program
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Effect test

Embodiment 1

[0043] Under the protection of nitrogen, put 5.64g (10mmol) of canthaxanthin into a 500ml three-necked flask, add 180ml of methanol to dissolve, then add 3.30g (15mmol) of oxidant iodosobenzene, lower the reaction temperature to 10°C, stir and mix evenly, Dissolve 0.20 g (5.0 mmol) of catalyst sodium hydroxide in 20 ml of methanol, and slowly add it dropwise to the reaction system within 30 minutes. Methanol was removed, water and dichloromethane were added for washing, and the layers were separated to obtain an organic phase containing crude dialkoxy ketal.

[0044] The above-mentioned organic phase was transferred to a 500ml three-necked flask, and 1.96g (1.0mmol) of 5wt% sulfuric acid aqueous solution was added, and the reaction was stirred at room temperature. After reacting for 5h, adding a 5wt% aqueous solution containing 2.0mmol sodium bicarbonate was quenched. The reaction was washed with water three times, the organic phase was separated, dried over anhydrous magnesiu...

Embodiment 2

[0047]Under nitrogen protection, put 5.64g (10mmol) of canthaxanthin into a 500ml three-necked flask, add 180ml of methanol to dissolve, then add 3.99g (12mmol) of iodobenzene acetate as an oxidant, lower the reaction temperature to 10°C, stir and mix evenly, and Catalyst potassium hydroxide 0.28g (5.0mmol) was dissolved in 20ml of methanol, slowly added dropwise to the reaction system within 30 minutes, after the dropwise addition was completed, the temperature was raised to room temperature, the reaction pressure was normal pressure, the reaction time was 12h, and the reaction ended Afterwards, methanol was removed under reduced pressure, water and dichloromethane were added for washing, and the layers were separated to obtain an organic phase containing crude dialkoxy ketal.

[0048] The above-mentioned organic phase was transferred to a 500ml three-necked flask, and 1.96g (1.0mmol) of 5wt% sulfuric acid aqueous solution was added, and the reaction was stirred at room temper...

Embodiment 3

[0050] Under the protection of nitrogen, put 5.64g (10mmol) of canthaxanthin into a 500ml three-necked flask, add 180ml of methanol to dissolve, then add 3.30g (15mmol) of oxidant iodosobenzene, lower the reaction temperature to 0°C, stir and mix evenly, Dissolve 0.20 g (5.0 mmol) of catalyst sodium hydroxide in 20 ml of methanol, and slowly add it dropwise to the reaction system within 30 minutes. After the dropwise addition is completed, the temperature is raised to 40° C., the reaction pressure is normal pressure, and the reaction time is 10 hours. After the reaction, methanol was removed under reduced pressure, water and dichloromethane were added for washing, and liquid separation was carried out to obtain an organic phase containing crude dialkoxy ketal.

[0051] The above-mentioned organic phase was transferred to a 500ml three-necked flask, and 1.96g (1.0mmol) of 5wt% sulfuric acid aqueous solution was added, and the reaction was stirred at room temperature. After react...

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Abstract

The invention discloses a method for preparing astaxanthin by oxidizing canthaxanthin. The method comprises the following steps: dissolving a substrate canthaxanthin in an organic solvent; performingreacting by using a high-valence iodide as an oxidant to prepare a dialkoxy ketal compound; and hydrolyzing the ketal compound under acidic conditions to obtain astaxanthin. Therefore, problems of complex route and harsh conditions in the prior art are solved, and a safer and more practical method is provided for astaxanthin synthesis.

Description

technical field [0001] The invention relates to a method for preparing astaxanthin by oxidizing canthaxanthin. Background technique [0002] Astaxanthin is a non-vitamin A carotenoid that widely exists in animals and is mainly produced by plants and microalgae in nature. Although the term "astaxanthin" is not commonly used in everyday life, astaxanthin is found in many human foods. The red color of most crustaceans such as shrimp, lobster, crab, etc. is due to the accumulation of astaxanthin, and the flesh color of some fish such as frogfish is also the result of astaxanthin accumulation. Astaxanthin is the compound with the most difficult synthesis and the highest value among several carotenoid products that have been industrially produced at present. It is now widely used in the fields of health care products, medicines, cosmetics, food and feed. [0003] There are two main sources of astaxanthin on the market, one is natural astaxanthin, derived from fermentation extrac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/24
CPCC07C403/24C07C2601/16
Inventor 沈宏强张涛王嘉辉张弈宇郭田辉潘亚男
Owner WANHUA CHEM GRP CO LTD
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