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Method for preparing canthaxanthin by utilizing oxidized beta-carotene

A technology of carotene and canthaxanthin, which is applied in the direction of organic chemistry, can solve the problems that are difficult to apply to industrialization, low yield, unstable hypobromous acid, etc., and achieve low cost, simple operation, and environmental friendliness

Inactive Publication Date: 2013-09-04
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In 2001, Quesnel (EP1253131) reported the use of H 2 o 2 As an oxidizing agent, I 2 As a catalyst, choose chloroform or chlorobenzene as a solvent, under room temperature, the yield can reach 40%, and the oxidant H 2 o 2 No pollution, but the yield of this method is not high
The disadvantage of this method is that the generated hypobromous acid is unstable and difficult to be applied to industrialization

Method used

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Examples

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Effect test

Embodiment 1

[0023] Take 2.68g (5mmol) of β-carotene in a 250ml flask, add 50ml of dichloromethane, stir at room temperature, then take 3.21g (15mmol) of sodium periodate and dissolve it in 50ml of water, add it dropwise to the flask, and add catalyst iodine Sodium chloride 0.08g (0.5mmol), reacted for 3 hours, separated the organic phase, washed 3 times with water, then dried with anhydrous sodium sulfate, filtered, and the filtrate was spin-dried to obtain a crude product, which was recrystallized with absolute ethanol to obtain Purple-red cantharidin 1.50g, yield 53.2%. m.p.206℃-208℃; 1 H NMR (500M, δ, CDCl 3 ):6.66(dt,J=20.2Hz,7.7Hz,4H),6.30(ddd,J=36.0Hz,27.3Hz,15.6Hz,l0H),2.44-2.55(m,4H),1.95-2.06(m, 12H), 1.80-1.89 (m, 10H), 1.18 (s, 12H).

Embodiment 2

[0025] Take 2.68g (5mmol) of β-carotene in a 250ml flask, add 50ml of dichloromethane, stir at room temperature, then take 2.12g (10mmol) of sodium periodate and dissolve it in 30ml of water, add it dropwise to the flask, and add catalyst iodine Sodium chloride 0.08g (0.5mmol), reacted for 3 hours, separated the organic phase, washed 3 times with water, then dried with anhydrous sodium sulfate, filtered, the filtrate was spin-dried, and then recrystallized with absolute ethanol to obtain purple-red cantharidin 1.12 g, yield 39.7%.

Embodiment 3

[0027] Take 2.68g (5mmol) of β-carotene in a 250ml flask, add 50ml of dichloromethane, stir at room temperature, then take 4.27g (20mmol) of sodium periodate and dissolve it in 70ml of water, add it dropwise to the flask, and add catalyst iodine Sodium chloride 0.08g (0.5mmol), reacted for 3 hours, separated the organic phase, washed 3 times with water, then dried with anhydrous sodium sulfate, filtered, the filtrate was spin-dried, and then recrystallized with absolute ethanol to obtain purple-red cantharidin 1.56 g, yield 55.4%.

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Abstract

The invention discloses a method for preparing canthaxanthin by utilizing oxidized beta-carotene. The method for preparing canthaxanthin comprises the following steps of: dissolving beta-carotene shown in a formula (I) (described in the specification) into an organic solvent, dropwise adding an oxidizing agent, namely a sodium periodate (NaIO4) aqueous solution, and adding a catalyst, namely sodium iodide (NaI), then stirring and reacting to obtain canthaxanthin shown in a formula (II). The organic solvent is one or combination of more than one of the following components: halogenated hydrocarbon containing 1-6 carbon atoms and fatty acid ester containing 3-10 carbon atoms. The method for preparing canthaxanthin has the advantages of mild reaction conditions, simple operation, low cost and environmental friendliness and is applicable to industrial production.

Description

(1) Technical field [0001] The invention relates to a method for preparing canthaxanthin by catalytic oxidation of β-carotene. (2) Background technology [0002] Cantharidin (or cantharidin) is a carotenoid found in certain mushrooms, crustaceans, fish, algae, eggs, blood and liver. In 1984, FDA / WHO approved cantharidin as a food additive and formulated quality standards. Cantharidin can be used as a food additive in beverages, ice cream, waffle biscuits, sauces, processed tomato products and processed meat products. Cantharidin is added to the feed of chickens, ducks and other poultry to produce a consumer-friendly orange color in egg yolks. [0003] In 1980, Joachim Paust (US4212827) et al reported a method for preparing canthaxanthin by oxidizing β-carotene. The method is to oxidize β-carotene with chlorate or bromate in the presence of a catalyst. The disadvantages are that the reaction time is too long, the initiation is difficult, the process is unstable, and more i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/24
Inventor 沈田华宋庆宝宋小利
Owner ZHEJIANG UNIV OF TECH
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