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New synthesis method of epsilon-carotene

A technology of carotene and synthesis method, which is applied in the new synthesis field of ε-carotene, can solve the problems of difficulty in the source of raw material C4 phosphonate, influence on product quality of carotene, influence on large-scale application, etc., and achieves good industrialization value and cost. Low, easy-to-operate effect

Inactive Publication Date: 2018-07-20
SHAOXING UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In the above route, before the key intermediate C15 phosphonate is condensed with C10 dialdehyde, the 1,2-position double bond needs to be transferred to the 2,3-position double bond, and if the double bond shift in this step is not complete, it will affect the final carrot Prime product quality
In addition, the source of raw material C4 phosphonate in this route is difficult, which restricts the large-scale preparation of C14 enol ether and affects the large-scale application of the entire preparation route of ε-carotene

Method used

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Examples

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Embodiment 1

[0030] Under nitrogen protection, in a 500mL three-necked flask, add potassium tert-butoxide (32.5g, 0.288mol) and a mixture of 100mL tetrahydrofuran and dimethyl sulfoxide (the volume ratio of the two is 8:1), start the mechanical stirring, wait until the temperature When cooling to -30°C, add the decacarbon bisphosphonate (53.1g, 0.13mol) dropwise, keep at -30-25°C, drop it for about half an hour, continue to heat and stir for about 1 hour to make the decacarbon bisphosphonate Complete dissociation into the corresponding carbanion. Then, at -30-25°C, pentadecaldehyde (56.7 g, 0.26 mol) was added dropwise, and the dropwise addition was completed in about 1 hour. The stirring was continued for about half an hour, followed by gas chromatography until the reaction was completed. Add 80 mL of water and 150 mL of diethyl ether, stir for 10 minutes, separate layers, wash the diethyl ether layer with 5% aqueous sodium chloride solution (3*50 mL), dry the organic layer with anhydrous...

Embodiment 2- Embodiment 8

[0034] Similar to Example 1, the difference is only to use different lye, solvent and temperature, specifically as shown in the following table:

[0035]

[0036]

[0037] In summary, the present invention has the following advantages:

[0038] 1. The preparation method provided by the present invention has the characteristics of simple process route, convenient operation, high yield, low cost, and recyclable by-products, etc., and has good industrial value.

[0039] 2. The present invention adopts the addition of deionized water to remove the by-product diethyl phosphonate in a layered manner to achieve the effect of improving the purity, and at the same time helps to recycle the by-product waste water.

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Abstract

The invention belongs to the field of carotenoids, and particularly relates to a new synthesis method of epsilon-carotene. The method comprises the following steps: dissolving 2,7-dimethyl-2,4,6-octanetriene-1,8-bisphosphonate in an anhydrous solvent, adding an alkali solution under the protection of nitrogen, and performing stirring to obtain a reaction solution 1; dropwise adding 3-methyl-5-(2,6,6-trimethyl-2-cyclohexane-1-yl)-2,4-pentadienal dissolved in the anhydrous solvent to the reaction solution 1, dropwise adding deionized water after the above dropwise addition reaction is completed,and performing uniform stirring to obtain a reaction solution 2; performing reduced pressure distillation on the reaction solution 2 to remove the organic solvent in order to obtain an aqueous solution, performing extraction by using the organic solvent, drying the obtained extract by anhydrous magnesium sulfate, and filtering the dried extract to obtain an organic solution; and distilling off the organic solvent in the organic solution, adding an alcohol solvent, performing a refluxing reaction under the protection of nitrogen, and cooling and filtering the obtained reaction solution to obtain the epsilon-carotene. The preparation method has the characteristics of simple process route, convenience in operation, high yield, low cost, recyclable byproducts and good industrialization values.

Description

technical field [0001] The invention belongs to the technical field of carotenoid preparation, and in particular relates to a new synthesis method of ε-carotene. Background technique [0002] ε-carotene (ε-carotene) (1) is a member of the carotenoid family, which has a good free radical quenching effect, so it has a good antioxidant effect and can effectively block the intracellular chain free radical reaction. The human body will naturally produce antioxidant substances between oxidation and anti-oxidation to achieve a balance. However, when people are aging or sick, the endogenous antioxidants are insufficient, and human body lipids are prone to peroxidation, leading to the occurrence of degenerative diseases And development. ε-carotene can be used as a supplementary exogenous natural antioxidant, which is one of the important ways to delay or reduce the harm to the human body due to oxidation. At the same time, ε-carotene can also be widely used in cosmetics, food and ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C403/24
CPCC07C403/24
Inventor 吴春雷沈润溥
Owner SHAOXING UNIVERSITY
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