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New quaternary phosphonium salt and synthesizing method applied for carotenoids

A technology of carotene and quaternary phosphonium salt, applied in the field of synthesis of new quaternary phosphonium salts and carotenoids, which can solve the problems of troublesome industrialization, no economic risk of reaction, and high operation requirements

Inactive Publication Date: 2007-09-19
广州巨元生化有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Another literature report adopts vinyl Grignard reagent and pseudoionone 6 to synthesize compound 3 (reaction formula is as follows), but needs to use vinyl chloride gas to generate Grignard reagent in tetrahydrofuran solvent (references: Journal of Agriculturaland Food Chemistry, 49, 2001, p 2780-2787), the reaction is not economical and has certain risks. It requires high operation for enterprises, and industrialization is also very troublesome.

Method used

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  • New quaternary phosphonium salt and synthesizing method applied for carotenoids
  • New quaternary phosphonium salt and synthesizing method applied for carotenoids
  • New quaternary phosphonium salt and synthesizing method applied for carotenoids

Examples

Experimental program
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Effect test

Embodiment 1

[0079] Embodiment 1: the preparation of 2-(triphenylphosphonium bromide)-diethyl ethyl phosphonate

[0080] In the 100ml three-necked flask, first add 20ml of dichloromethane, 3.1g (0.012mol) of triphenylphosphine, stir for 15min, N 2 Add 2.45g (0.01mol) diethyl 2-bromoethylphosphonate under protection, and stir at room temperature for 24h. A white solid was precipitated, filtered, and recrystallized from dichloromethane / methanol to obtain pure diethyl 2-(triphenylphosphonium bromide)-ethylphosphonic acid with a yield of 90%.

Embodiment 2

[0081] Embodiment 2: the preparation of 2-(triphenylphosphonium hydrogensulfate)-ethyl phosphonic acid diethyl ester

[0082] First add 5.8g (0.022mol) of triphenylphosphine, 20ml of methanol and 1.67g (0.017mol) of sulfuric acid into a 100ml three-necked flask, stir for 30min, and add 3.1g (0.017mol) of 2-hydroxyethylphosphine under the protection of N2 Acid diethyl ester, stirred at 30°C for 10h. Methanol was removed under reduced pressure, and dichloromethane / methanol recrystallized to obtain pure 2-(triphenylphosphonium hydrogensulfate)-ethylphosphonic acid diethyl ester with a yield of 88%.

Embodiment 3

[0083] Embodiment 3: Preparation of 2-(triphenylphosphonium p-toluenesulfonate)-ethylphosphonic acid diethyl ester

[0084] First add 5.8g (0.022mol) of triphenylphosphine, 20ml of methanol and 1.63g (0.017mol) of p-toluenesulfonic acid into a 100ml three-necked flask, stir for 30min, and add 3.1g (0.017mol) of 2-hydroxy Diethyl ethyl phosphonate, stirred at 30°C for 10h. Methanol was removed under reduced pressure, and dichloromethane / methanol was recrystallized to obtain pure 2-(triphenylphosphonium p-toluenesulfonate)-ethylphosphonic acid diethyl ester with a yield of 88%.

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Abstract

The invention provides a new quaternary phosphonium salt I for synthesizing the carotenoid and provides a method for preparing such compound and preparing the carotenoid compound especially lycopene by the intermediate. The method skillfully use the necessary reaction substrate activity difference of the the Writing-Homer reaction and Witting reaction and gets the target product by respectively two condensation reactions with ketone and aldehyde. The new method avoids the disadvantages and has a simple operation and an accessible raw material and does not need special reaction equipments and facilitates to achieve industrialisation.

Description

field of invention [0001] The invention relates to a new quaternary phosphorus salt and a preparation method, and the application of the quaternary phosphorus salt to the synthesis of carotenoid polyene compounds, especially lycopene. Background of the invention [0002] Carotenoids can effectively quench singlet oxygen and hydroxyl radicals, so they have disease-preventing and disease-resistant physiological activities. They are a class of compounds that are widely used as nutrients, food colorants and food additives. Specific compounds include β -Carotene, lycopene, astaxanthin, nopain, zeaxanthin, canthaxanthin, etc. Among them, the antioxidant activity of lycopene is three times that of β-carotene and 100 times that of vitamin E. At present, there are many methods for preparing lycopene in the laboratory, and there is an industrialized synthetic route as follows (references: Helvetica chimica acta, 75, 1992, p1848-1864; CN1319600, 2001, the applicant is BASF, Germany): ...

Claims

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Application Information

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IPC IPC(8): C07F9/54C07C403/24
Inventor 刘庆辉王玉良朱基美刘建新
Owner 广州巨元生化有限公司
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