Method for preparing canthaxanthin

A technology of cantharidin and oxidant, applied in the directions of organic chemistry, organic chemistry, etc., can solve the problems of large amount of oxidant and low yield of cantharidin, and achieve the effects of shortening reaction time, reducing dosage and improving yield.

Active Publication Date: 2019-02-22
XIAMEN KINGDOMWAY VI TAMIN INC +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0011] The purpose of the present invention is to solve the disadvantages of lower yield and larger consumption of oxidant wh

Method used

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  • Method for preparing canthaxanthin

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specific Embodiment approach

[0033] The method of dissolving the β-carotene, the oxidizing agent I and the phase transfer catalyst in the organic solvent is not particularly limited in the present invention, and the above three substances can be added into the organic solvent in any order for dissolution. According to a specific embodiment of the present invention, the method of dissolving the β-carotene, the oxidizing agent I and the phase transfer catalyst in the organic solvent is to dissolve the β-carotene in the organic solvent first, and then add the oxidizing agent I and the phase transfer catalyst. The phase transfer catalyst is dissolved.

[0034] In the present invention, the temperature of the system needs to be controlled at 0-15° C. when adding the oxidizing agent I, that is, after the β-carotene, the oxidizing agent I and the phase transfer catalyst are dissolved in the organic solvent, the temperature of the system is higher than 15° C. °C or lower than 0 °C, the temperature of the system n...

Embodiment 1

[0046] Add 6g beta-carotene (99%, 0.01106mol) and 120ml methylene dichloride in 500ml four-necked flask, add 8g hydrogen peroxide aqueous solution (10%w / w, 0.02352mol) and 0.03g tetrabutylammonium bromide, Vacuumize and replenish nitrogen three times, cool down to 0-5°C, add 27.6g of sodium hypochlorite aqueous solution (available chlorine content is 1.5wt%, 0.01166mol, pH value is adjusted to 7) which is pre-cooled to 5°C very slowly, and the temperature of the dropping process is Control at 0-5°C, keep warm at this temperature for 6 hours after the dropwise addition, stand and separate to obtain an oil layer and a water layer, extract the water layer once with 30ml dichloromethane, combine the extracted dichloromethane layer and the oil layer with 100ml Wash once with 2% w / v sodium sulfite aqueous solution, once with 100ml of water, concentrate the oil layer to dryness, add 50ml of ethanol, perform isomerization reaction at 70°C for 8 hours, lower to normal temperature, filte...

Embodiment 2

[0048] The 8g hydrogen peroxide aqueous solution (10%w / w, 0.02352mol) in embodiment 1 is replaced by 6.41g tert-butyl alcohol peroxide aqueous solution (70%w / w, 0.04979mol), dropwise temperature and follow-up insulation temperature All are replaced with 5~10 ℃, all the other are with embodiment 1, obtain 5.70g cantharidin, content is 95.23%, and molar yield is 87.02%.

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Abstract

The invention belongs to the field of organic synthesis, and specifically discloses a method for preparing canthaxanthin. The method comprises the following steps: dissolving beta-carotene, an oxidantI and a phase transfer catalyst in an organic solvent; adding an oxidant II at 0-15 DEG C; performing oxidation reaction at 0-15 DEG C after the addition is completed; and then, separating an oil phase from the obtained oxidation reaction product and performing isomerization reaction to obtain all-trans canthaxanthin, wherein the oxidant I is a peroxide oxidant, and the oxidant II is a hypochlorite oxidant. The method for preparing canthaxanthin provided by the invention can be adopted to significantly increase the yield of reaction, reduce the dosage of the oxidants and shorten the reactiontime.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and in particular relates to a preparation method of cantharidin. Background technique [0002] Cantharidin is a carotenoid that widely exists in nature and is mainly used in food colorants and feed additives, and has important commercial value. The molecular formula of cantharidin is C 40 h 52 o 2 , the structural formula is shown in the following formula. [0003] [0004] There are two main synthetic methods of cantharidin, namely total synthesis and one-step oxidation. [0005] Described total synthesis method is the C that proposed by Roche company in 1979 15 +C 10 +C 15 Synthetic routes, specifically, the 3-oxo-ionone-based C 15 Triphenylphosphine bromide and C 10 Triene dialdehyde is used as raw material, and canthaxanthin is obtained through wittig-horner reaction (see Michael Rosenberger, Patrick McDougal, Gabriel Saucy et al. New Approaches to the Synthesis of Canthaxanthin....

Claims

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Application Information

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IPC IPC(8): C07C403/24
CPCC07B2200/13C07C403/24C07C2601/16
Inventor 赵家宇林兴蔡育森何剑洋刘敏
Owner XIAMEN KINGDOMWAY VI TAMIN INC
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