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Method for Synthesizing Astaxanthin Intermediate Using 2,6,6-trimethyl-3,4-dihydroxy-2-cyclohexen-1-one

A dihydroxy, cyclohexene technology, applied in the preparation of heterocyclic compounds, organic chemistry and other directions, can solve the problems of difficult separation and purification, product isomerization, affecting product yield, etc., to improve reaction yield, good separation, The effect of reducing the concentration of acid

Active Publication Date: 2015-07-29
广州巨元生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] In the total synthesis of astaxanthin, the most mature industrial route is 2(C9+C6)+C10=C40 (Pure.Appl.Chem., Vol.74, No.8, pp1369-1382, 2002,), where C9 The construction of fragments generally adopts the protection method of acetone acetal, but the deprotection of acetone acetal requires more severe conditions, which easily leads to isomerization of the product, and the acetone produced by the reaction is evaporated together with the reaction solvent, forming a difficult to separate and purify mixed solvent
[0004] Both Chinese patent applications CN 1098101A and CN 101148433A mention the use of vinyl ether as a protective agent, but dichloromethane is used as a solvent in the reaction process, and complex processes such as washing, extraction, and concentration are still required for the completion of the reaction
Moreover, in the subsequent deprotection step, a two-phase reaction is adopted, and it is necessary to use a higher concentration of acid to completely deprotect, which not only affects the yield of the product but also leads to isomerization of the product

Method used

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  • Method for Synthesizing Astaxanthin Intermediate Using 2,6,6-trimethyl-3,4-dihydroxy-2-cyclohexen-1-one

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Embodiment 1

[0032] A method for synthesizing an astaxanthin intermediate, the specific steps are as follows: add 170g (1.0mol) 2,6,6-trimethyl-3,4-dihydroxy-2-cyclohexen-1-one crystals to Put it into a 1000ml four-necked bottle equipped with a mechanical stirrer, a thermometer, a condenser tube and a drying tube. Add 350ml of n-heptane and stir to disperse, add 0.3g (1.6mmol) of p-toluenesulfonic acid, add 144g (2.0mol) of vinyl ethyl ether dropwise at room temperature, and drop it in 45 minutes. After stirring at room temperature for 30 minutes, raise the temperature to 60°C for 1 hour, add 1 g of triethylamine, and cool down to room temperature to obtain a reaction solution containing structural formula V, which can be directly reacted with alkynyllithium to obtain a product of structural formula VI ; Then add 200ml of 75% ethanol and 1g (0.01mol) of concentrated sulfuric acid in a 1000ml four-necked flask equipped with a mechanical stirrer, a thermometer, a condenser tube and a nitroge...

Embodiment 2

[0036] A method for synthesizing an astaxanthin intermediate, the specific steps are as follows: add 170g (1.0mol) crystal 2,6,6-trimethyl-3,4-dihydroxy-2-cyclohexen-1-one to Put it into a 1000ml four-necked bottle equipped with a mechanical stirrer, a thermometer, a condenser tube and a drying tube. Add 300ml cyclohexane and stir to disperse, add 0.6g (3.2mmol) p-toluenesulfonic acid, add 172g (2.0mol) propenyl ethyl ether dropwise at room temperature, and drop it in 45 minutes. After stirring at room temperature for 30 minutes, the temperature was raised to 70°C for 1 hour, 2 g of triethylamine was added, and the temperature was lowered to room temperature to obtain a reaction solution containing the structural formula VIII, which was directly reacted with alkynyl lithium to obtain the product of the structural formula IX ; Then add 200ml of 75% ethanol and 1g (0.01mol) of concentrated sulfuric acid in a 1000ml four-necked flask equipped with a mechanical stirrer, a thermome...

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Abstract

The invention discloses a method for synthesizing an astaxanthin intermediate by utilizing 2, 6, 6-trimethyl-3, 4-dihydroxy-2-cyclohexene-1-one. The method comprises the following steps of: dispersing the 2, 6, 6-trimethyl-3, 4-dihydroxy-2-cyclohexene-1-one in a non-polar solvent, adding an acid catalyst, dripping enol ether at room temperature for reaction, adding tertiary amine for termination reaction, then cooling, directly dissolving a reaction solution into an ethanol water solution with a compound obtained by reaction of an alkynyl reagent, then dripping into the ethanol water solution dissolving an acid, adding sodium carbonate for termination reaction after the end of dripping, performing reduced pressure distillation and recovery of the solvent, adding water into residues for stratification, extracting a water phase with dichloromethane, merging and drying organic phases, and then concentrating so as to synthesize the astaxanthin intermediate. The method disclosed by the invention has the advantages of high yield of products, low isomerization of the products and the like.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a method for synthesizing an astaxanthin intermediate by using 2,6,6-trimethyl-3,4-dihydroxy-2-cyclohexen-1-one. Background technique [0002] Astaxanthin has a natural purple color and strong antioxidant effect, and is widely used in medicine, food, cosmetics, health products and feed additives. It can not only play the role of coloring, but also have the functions of fresh-keeping, anti-aging, anti-oxidation and improving immunity. [0003] In the total synthesis of astaxanthin, the most mature industrial route is 2(C9+C6)+C10=C40 (Pure.Appl.Chem., Vol.74, No.8, pp1369-1382, 2002,), where C9 The construction of fragments generally adopts the protection method of acetone acetal, but the deprotection of acetone acetal requires more severe conditions, which easily leads to isomerization of the product, and the acetone produced by the reaction is evaporated together with the react...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/743C07C45/59C07D317/46
Inventor 姚伟平刘庆辉廖艳金
Owner 广州巨元生化有限公司
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