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Synthesis of astaxanthin

A technology of astaxanthin and astaxanthin, applied in the direction of organic chemistry, can solve the problems of less than 30% total yield, many chemical reagents, complicated operation, etc., and achieves convenient operation, good reaction selectivity and simple process. Effect

Inactive Publication Date: 2006-08-16
ZHEJIANG UNIV +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0020] This route involves a total of six steps of reaction, although the single-step yield is more than 70%, but the total yield is less than 30%, and the chemical reagents used are many and the operation is complicated

Method used

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  • Synthesis of astaxanthin
  • Synthesis of astaxanthin
  • Synthesis of astaxanthin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 3.00g of astaxanthin (A) and 1000ml of methanol into a 1000ml three-neck flask, then add 3.26g of sodium methoxide according to 12 times the molar number of (A), and feed oxygen at a rate of 0.15L / min under stirring to control the reaction temperature temperature was 65°C, and the temperature was kept for 17 hours. After the reaction is completed, the solvent is removed to obtain a solid crude product, which is then dissolved with dichloromethane, filtered, and the filtrate is precipitated to obtain 0.88 g of unreacted astaxanthin (A), and then the residual solid is dissolved in water to obtain an alkaline reaction solution. Neutralize until the pH value becomes 4, stop adding acid, filter, wash and dry to obtain 2.04g of product, which contains 81.2% astaxanthin (B), and the actual yield is 78.7%.

Embodiment 2

[0032] Add 2.00g of astaxanthin (A) and 1000ml of ethanol into a 1000ml three-neck flask, then add 1.50g of potassium hydroxide according to 8 times the molar number of (A), and feed oxygen at a rate of 0.3L / min under stirring to control the reaction The temperature was 55°C, and the reaction was kept for 11 hours. After the reaction is completed, the solvent is removed to obtain a solid crude product, which is then dissolved with dichloromethane, filtered, and the filtrate is precipitated to obtain 0.43 g of unreacted astaxanthin (A), and then the residual solid is dissolved in water to obtain an alkaline reaction solution. Neutralize until the pH value becomes 5, stop adding acid, filter, wash and dry to obtain 1.53g of product, which contains 90.1% astaxanthin (B), and the actual yield is 88.4%.

Embodiment 3

[0034] Add 4.50g of astaxanthin (A) and 1000ml of isopropanol in a 1000ml three-necked flask, then add 7.61g of potassium hydroxide by 18 times the molar number of (A), and feed oxygen at a rate of 0.08L / min under stirring, Control the reaction temperature to 75° C., and keep the reaction for 28 hours. After the reaction is completed, the solvent is removed to obtain a solid crude product, which is then dissolved with dichloromethane, filtered, and the filtrate is precipitated to obtain 1.82 g of unreacted astaxanthin (A), and then the residual solid is dissolved in water to obtain an alkaline reaction solution. Neutralize until the pH value becomes 4, stop adding acid, filter, wash and dry to obtain 2.43g of product, which contains 71.2% astaxanthin (B), and the actual yield is 64.5%.

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Abstract

Synthesis of astacin is carried out by dispersing astaxanthin with mass concentration 1-6g / L and alkali in proportion 1:2-20 in alcohol solvent, agitating while inducing into oxygen, reacting at 30-80 degrees C to obtain reactant, removing alcohol solvent to obtain solid crude product, dissolving the crude product by methylene chloride, filtering, dissolving the filter residue by water to obtain alkali reactive liquid, neutralizing by acid to pH value 4-6, filtering, washing by water and drying to obtain final product. It is simple and convenient, has more yield and no by-product.

Description

technical field [0001] The invention relates to a method for synthesizing astaxanthin. Background technique [0002] Astaxanthin (astacene) is an acidic ketone carotenoid with the molecular formula C 40 h 48 o 4 , melting point 214°C, is astaxanthin (chemical name is 3,3'-dihydroxy-4,4'-diketone-β,β'-carotene, molecular formula is C 40 h 52 o 4 ) is the main oxidation product. There are two tautomers of astaxanthin, the chemical names are 3,3'-dihydroxy-2,3,2',3'-tetradehydro-β,β'-carotene-4,4' - diketone and 3,4-3',4'-tetraketo-β,β'-carotene, the former generally represents astaxanthin. The chemical structures of the two tautomers of astaxanthin and astaxanthin are shown below: [0003] [0004] Astaxanthin (A) [0005] [0006] Astaxanthin (B) [0007] Astaxanthin can be used as a feed additive. Takumi et al. have tried adding astaxanthin to rice bran to feed Artemia [Nippon Suisan Gakkaishi, 49, (1), 137-139, 1...

Claims

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Application Information

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IPC IPC(8): C07C403/24
Inventor 仇丹陈志荣石立芳黄国东吴建华梁志军
Owner ZHEJIANG UNIV
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