Halogenated curcumin derivative, preparation method thereof and application of halogenated curcumin derivative in preservation of aquatic products

A technology for substituting curcumin and derivatives, which is applied to halogenated curcumin derivatives, its preparation method and its application field in the preservation of aquatic products, which can solve the problems of less active oxygen and improve the preservation effect, and extend the shelf life , mild reaction conditions and simple preparation steps

Active Publication Date: 2021-11-26
ZHEJIANG OCEAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The present invention provides a halogenated curcumin in order to overcome the problem that the active oxygen generated by the photosensitizer in the photodynamic sterilization in the prior art is less and the preservation effect needs to be improved. Derivatives, their preparation methods and their application in the preservation of aquatic products, the halogenated curcumin derivatives have higher intersystem crossing efficiency under the influence of the heavy atom effect of non-metallic halogen atoms, and can obtain higher Singlet oxygen yield rate, and the preparation steps are simple, and it has a good fresh-keeping effect on aquatic products

Method used

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  • Halogenated curcumin derivative, preparation method thereof and application of halogenated curcumin derivative in preservation of aquatic products
  • Halogenated curcumin derivative, preparation method thereof and application of halogenated curcumin derivative in preservation of aquatic products
  • Halogenated curcumin derivative, preparation method thereof and application of halogenated curcumin derivative in preservation of aquatic products

Examples

Experimental program
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Effect test

Embodiment 1

[0044] A kind of bromocurcumin derivative, its structural formula is The preparation steps are as follows:

[0045] (1) At 25°C, N 2 Under protective conditions, dissolve 1mmoL of acetylacetone and equimolar amounts of boric anhydride in 20mL of ethyl acetate, and stir for 0.5h;

[0046] (2) Add 2mmoL of 4-bromo-3-methoxybenzaldehyde and 2mmoL of tributyl borate, and continue stirring for 0.5h;

[0047] (3) Add 0.01mmoL catalytic amount of n-butylamine dropwise, and continue to stir and react for 24h;

[0048] (4) After the reaction is over, add 10mL of 10% hydrochloric acid solution and continue to stir for 1h;

[0049] (5) The organic phase was separated, extracted with ethyl acetate, dried with anhydrous sodium sulfate, and rotary evaporated to obtain a crude product, which was purified by column chromatography to obtain the target bromocurcumin derivative.

[0050] The product obtained in Example 1 is detected by ESI mass spectrometry, and the detection results are as...

Embodiment 2

[0058] A photodynamic sterilization method for fresh shrimp, the steps are as follows Figure 5 Shown:

[0059] (1) prepare the aqueous solution of bromocurcumin derivatives in the light-proof water tank, and its concentration is 20 μ mol / L;

[0060] (2) Select fresh, complete, bright-colored and uniform-sized Chinese tube whip shrimp, immerse it in ice water (1:2, w / v) to freeze to death, wash it with sterile saline and drain the surface water ;

[0061] (3) Soaking is used to soak the aquatic product prepared in step (2) in the aqueous solution of halogenated curcumin derivatives prepared in step (1) for 10 minutes and then take it out;

[0062] (4) Immediately place the aquatic product obtained in step (3) under a blue LED matrix with an optical power of 10W and irradiate for 120s with a wavelength of 470nm.

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Abstract

The invention relates to the field of aquatic product processing and storage, and discloses a halogenated curcumin derivative, a preparation method thereof and an application of the halogenated curcumin derivative in aquatic product preservation in order to solve the problems that in the prior art, active oxygen generated by a photosensitizer in photodynamic sterilization is less, and the aquatic product preservation effect needs to be improved. The halogenated curcumin derivative is shown as a structural general formula I, and in the structural general formula I, R1 is one of F, Cl, Br and I; and R2 is one of F, Cl, Br, I and OH. The halogenated curcumin derivative can be prepared by a one-step method and can be used for photodynamic sterilization of aquatic products. The preparation steps are simple, the reaction conditions are mild, the singlet oxygen yield of the prepared halogenated curcumin derivative under blue light irradiation is high, the sterilization and preservation effects on aquatic products are good, the shelf life of fresh shrimps can be effectively prolonged, and the influence on food sense is small.

Description

technical field [0001] The invention relates to the field of processing and storage of aquatic products, in particular to a halogenated curcumin derivative, its preparation method and its application in preservation of aquatic products. Background technique [0002] Photodynamic sterilization is a new type of non-thermal sterilization technology. Its principle is to use photosensitizer molecules to sensitize oxygen under visible light irradiation to generate cytotoxic active oxygen (mainly singlet oxygen, 1 o 2 ) to kill pathogenic microorganisms. Because photodynamic sterilization has the advantages of broad-spectrum bactericidal properties, non-toxicity, and no drug resistance, it has great application prospects in the field of food sterilization, especially the sterilization and preservation of aquatic products. Moreover, photodynamic sterilization technology can also better maintain the original nutrients, flavor, color, taste and freshness of aquatic products on the p...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/255C07C45/74A23B4/20
CPCC07C49/255A23B4/20A23V2002/00A23V2200/10
Inventor 焦龙张宾
Owner ZHEJIANG OCEAN UNIV
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