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Method for synthesizing astaxanthin intermediate

A synthesis method and an intermediate technology, applied in the field of astaxanthin preparation, can solve the problems of increased reaction route steps and costs, complex reaction route, cumbersome operation, etc., to avoid multiple introductions and repeated hydrolysis, simplify the process, and ensure Yield effect

Active Publication Date: 2018-02-27
SHANGYU NHU BIOCHEM IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This leads to additional reaction steps and reaction raw materials, which increases the steps and expenses of the reaction route, and the difficulty of separation and purification; (b) the reaction route is complicated and the operation is cumbersome; (c) the yield is low

Method used

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  • Method for synthesizing astaxanthin intermediate
  • Method for synthesizing astaxanthin intermediate
  • Method for synthesizing astaxanthin intermediate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] (1) Synthesis of 3-methyl-1-pentene-4-yn-3-alcohol lithium

[0052] Take 800ml of liquid ammonia, and cool it to -45°C with dry ice alcohol, take 10.5g of lithium particles, put it into the liquid ammonia, and put it in for 20 minutes. The system temperature is -40°C, the temperature difference is within 2°C, and keep warm for 40 minutes;

[0053] Pass acetylene for 1 hour, the flow rate is 0.6L / min, the temperature is controlled at -35°C, and then the alcohol bath is raised to 0°C to volatilize the liquid ammonia. As the liquid ammonia decreases to the remaining 500-600ml, start to drop 450g of toluene, raise the temperature to 10°C, continue to volatilize the liquid ammonia, and cool to -10°C after the addition of toluene is complete.

[0054] Dissolve 90g of 1-buten-3-one in 50g of toluene and add it dropwise to the above reaction system. Control the temperature to -5°C ~ -10°C, keep the temperature for 30 minutes after dropping, and generate lithium 3-methyl-1-pent...

Embodiment 2

[0067] The reaction condition of embodiment 2 is identical with embodiment 1, but the heterodiketone added in step (3) is 3,5,5,7-tetramethyl-1,2-dioxocyclopentabicyclo[ 4,1,0]-3-conen-4-one, the added mass is 240g.

[0068] Step (3) After the condensation reaction, the sample was measured, and the total yield of the first three steps was calculated to be 87%. The final product purity of embodiment 2 is 96%, and the total yield is 76%.

Embodiment 3

[0070] The reaction condition of embodiment 3 is identical with embodiment 1, but adopts sherwood oil to replace toluene to carry out liquid ammonia replacement in step (1).

[0071] After the condensation reaction in step (3) was completed, the sample was measured, and the total yield of the first three steps was calculated to be 85%. The final product purity of embodiment 2 is 94%, and the total yield is 74%.

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Abstract

The invention relates to a method for synthesizing an astaxanthin intermediate. The method specifically comprises the following steps: 1) adding lithium into liquid ammonia to implement a reaction, introducing acetylene to synthesize acetylene-based lithium, replacing the liquid ammonia with an organic solvent, and adding 1-butene-3-ketone to implement a reaction continuously, so as to generate 3-methyl-1-amylene-4-alkyne-3-lithium alkoxide; 2) adding lithium into the liquid ammonia to implement a reaction, and further adding the product obtained in the step 1) to generate 3-methyl-1-amylene-4-alkynyl based lithium-3-lithium alkoxide; 3) performing a condensation reaction on the product obtained in the step 2) with heterogeneous diketone so as to generate a condensation compound; 4) performing acid hydrolysis on the condensation compound obtained in the step 3), and treating with a reduction triple bond so as to obtain 2,4,4-trimethyl-6-hydroxy-3-(3-methyl-1,4-dipentene-3-hydroxy)-2-cyclohexenone; 5) enabling 2,4,4-trimethyl-6-hydroxy-3-(3-methyl-1,4-dipentene-3-hydroxy)-2-cyclohexenone to react with hydrobromic acid and triphenylphosphine in sequence, thereby finally generating the astaxanthin intermediate. By adopting the method, multiple times of introduction and repeated hydrolysis of extra protection groups are avoided, so that the raw materials are saved, and the preparation route is simplified.

Description

technical field [0001] The invention relates to the field of preparation of astaxanthin, in particular to a method for synthesizing an astaxanthin intermediate. Background technique [0002] Astaxanthin is a non-provitamin A carotenoid that occurs naturally in crustaceans, fish, birds and certain microalgae. The chemical name of astaxanthin is 3,3'-dihydroxy-β,β'-carotene-4,4'-dione, molecular formula C 40 h 52 o 4 , with a relative molecular weight of 596.86, is a terpene-like unsaturated compound whose chemical structure consists of 4 isoprene units connected in the form of conjugated double bonds. There is a six-membered ring structure composed of two isoprene units at both ends, which is similar to the structure of β-carotene. Its structural formula is as follows: [0003] [0004] Now the sources of astaxanthin mainly include biological extraction and chemical synthesis, and most of the astaxanthin sold in the world today is synthetic astaxanthin. Regarding the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/54
Inventor 田金金吕国锋管敏虾傅一苇
Owner SHANGYU NHU BIOCHEM IND
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