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Method for synthesizing astaxsanthin

An astaxanthin and compound technology, which is applied in the field of new synthesis of astaxanthin, can solve the problems of high cost and difficult preparation of intermediates, and achieves the effects of convenient operation, low raw material cost and good reaction selectivity.

Active Publication Date: 2006-06-21
ZHEJIANG UNIV +3
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The preparation of intermediates (L) and (P) of this route is more difficult and the cost is higher

Method used

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  • Method for synthesizing astaxsanthin
  • Method for synthesizing astaxsanthin
  • Method for synthesizing astaxsanthin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] a. trans C 6 Preparation of phosphonium salt (T)

[0023] Add 9.6g of C6 alcohol and 200ml of dichloromethane into a 500ml three-neck flask, add 20g of 58% hydrobromic acid dropwise at room temperature, keep the reaction for 30 minutes after dropping, add 100ml of water, and separate the dichloromethane layer. Concentrate the dichloromethane layer to 50ml, add ethyl acetate 150ml, PPh 3 28g, reacted at room temperature for 24 hours, filtered, and the filter cake was washed with 30ml ethyl acetate, dried in vacuo to obtain C 6 Phosphonium salt 26g. The mother liquor was concentrated to about 100ml, cooled, and 8g of phosphine salt was precipitated, with a total yield of 81%.

[0024] b.C 22 Preparation of Diyne Polyene Compound (U)

[0025] Add 21g of C into a 1000ml four-neck flask 6 Phosphonium salt, 4g C 10 Dialdehyde (F), 250ml of methanol, control the reaction temperature at about 10°C, add 70ml of methanol solution of 10% potassium tert-butoxide dropwise wit...

Embodiment 2

[0031] a. trans C 6 Preparation of phosphonium salt (T)

[0032] Add 9.6g of C6 alcohol and 200ml of dichloromethane into a 500ml three-neck flask, add 10g of 30% hydrochloric acid dropwise at room temperature, keep the reaction for 30 minutes after dropping, add 100ml of water, and separate the dichloromethane layer. Concentrate the dichloromethane layer to 50ml, add 150ml of methyl acetate, PPh 3 28g, reacted at room temperature for 24 hours, filtered, and the filter cake was washed with 30ml ethyl acetate, dried in vacuo to obtain C 6 Phosphonium salt 26g. The mother liquor was concentrated to about 100ml, cooled, and 7g of phosphine salt was precipitated, with a total yield of 71%.

[0033] b.C 22 Preparation of Diyne Polyene Compound (U)

[0034] Add 21g of C into a 1000ml four-neck flask 6 Phosphonium salt, 4g C 10 Dialdehyde (F), 250ml of ethanol, control the reaction temperature at about 10°C, stir and add 70ml of methanol solution of 10% potassium tert-butoxide...

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Abstract

The present invention relates to a new method for the synthesis of astaxanthin, which consists of the following reactions: ∴ The method uses the by-product trans-C in the production of vitamin A 6 Alcohol is used as the starting material, and astaxanthin is synthesized through four-step reactions, which is a process with good reaction selectivity, high reaction yield, less pollution and simple operation.

Description

technical field [0001] The invention relates to a new synthesis process of astaxanthin. Background technique [0002] Astaxanthin is a kind of carotenoid, which is found in the shell of shrimp and crab, and can make animals or food produce bright colors. Astaxanthin is mainly used in the farming of aquatic products. The synthetic methods of astaxanthin reported in the literature mainly contain the following types: [0003] 1. C proposed by E.widmer et al. 15 +C 10 +C 15 Route [Helv.Chim.Acta 64,2436, (1981)], this route is made up of following several step reactions: [0004] [0005] This route is the industrialized route of Roche Company, and its disadvantage is that the reaction yield from (C) to (E) is not high, because (C) to (D) reduction reaction can produce hydroxyl and double bond addition reaction and produce Dihydrofuran or dihydropyran by-products. [0006] 2.H.Ernst et al proposed improved C 15 +C 10 +C 15 Route (USP 5652099), because the route prop...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C403/24
Inventor 陈志荣李浩然王纯超刘信洪黄国东曾庆宇
Owner ZHEJIANG UNIV
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