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A kind of water-soluble astaxanthin derivative and preparation method thereof

A technology of astaxanthin and derivatives, applied in food science, animal feed, additional food elements, etc., to achieve the effect of improving the application range, simple process, and expanding the application range

Active Publication Date: 2018-01-16
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] The purpose of the present invention is to provide a water-soluble astaxanthin derivative and its preparation method. The prepared derivative improves the disadvantage of astaxanthin itself being insoluble in water, increases the application range of astaxanthin, and improves the stability

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  • A kind of water-soluble astaxanthin derivative and preparation method thereof
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  • A kind of water-soluble astaxanthin derivative and preparation method thereof

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preparation example Construction

[0024] The astaxanthin succinate diester-PEG derivative of the present invention and its preparation method, the specific steps are as follows:

[0025] Raw material: use astaxanthin powder or astaxanthin solution dissolved in a specific organic solvent as the raw material, the structural formula is as formula (III);

[0026]

[0027] 1) Add succinic anhydride to the raw materials, the molar ratio of astaxanthin to succinic anhydride is 1:10~1:20, heating, temperature control at 30℃~100℃, reaction time 0.5h~20h; add after reaction The water was stirred and the precipitate was collected by centrifugation to obtain the hydroxyl esterified product (II). Since succinic anhydride is a cyclic acid anhydride, its carboxyl groups are connected, so its reaction product with hydroxyl exists in the form of dibasic acid monoester and introduces another carboxylic acid group. After the reaction, water was added to the reaction system to precipitate the produced astaxanthin succinic acid dieste...

Embodiment 1

[0031] Example 1 Preparation of astaxanthin succinate diester-PEG400 derivative

[0032] Weigh 1g of astaxanthin powder, add 3 times the molar amount of succinic anhydride, heat to 50°C, and react for 2h; after the reaction is completed, slowly add water to the reaction system and stir. When precipitation occurs, centrifuge to collect the precipitate to obtain the hydroxy ester The resulting hydroxyl esterified product, dichloromethane, was added 15 times the molar amount of polyethylene glycol 500, and reacted for 2 hours at 50°C. After the reaction was completed, the dichloromethane in the system was removed, and the precipitate was collected to obtain shrimp Penicillin succinic acid diester—PEG400 derivative, the obtained derivative was separated and characterized by TLC, and the results are as follows figure 2 As shown in 2, will figure 2 Scraper purification and saponification of the reaction components in the saponification process, using 0.05mol / L KOH / methanol solution to...

Embodiment 2

[0033] Example 2 Preparation of astaxanthin succinate diester-PEG1000 derivative

[0034] Weigh 10 mL of a dioxane solution containing 1 g of astaxanthin, add 4 times the molar amount of succinic anhydride, heat to 60°C, and react for 1.5 hours; after the reaction is completed, slowly add water to the reaction system and stir until precipitation occurs. The precipitate was collected by centrifugation to obtain the hydroxyl esterification product; the obtained hydroxyl esterification product was dissolved in acetone solution, and 10 times the molar amount of polyethylene glycol 1000 was added. The reaction was carried out at 65°C for 1 hour. After the reaction was completed, the system was removed Acetone solution, collect the precipitate to obtain the astaxanthin succinate diester—PEG1000 derivative. The obtained derivative is separated and characterized by TLC such as TLC figure 2 As shown in 3, the reaction components in 3 are subjected to scraper purification and saponificatio...

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Abstract

The invention provides water-soluble astaxanthin derivatives, particularly astaxanthin succinate PEG (polyethylene glycol) derivatives and a preparation method thereof. According to the method, fat-soluble astaxanthin is used as the raw material, succinate is introduced through hydroxy esterification, and the product and PEG with specific polymerization degree are subjected to esterification reaction to obtain the water-soluble astaxanthin derivatives. The diastaxanthin succinate PEG derivatives have favorable water solubility, greatly widen the application range of the astaxanthin, and can be applied to meat products and aquatic products as a food additive. The water-soluble astaxanthin derivatives have favorable oxidation resistance, and thus, can be used in cosmetics and pharmaceutical products and also be added into health food and the like as a functional factor.

Description

Technical field [0001] The invention belongs to the technical field of astaxanthin processing and preparation, and specifically relates to an astaxanthin succinate diester derivative and a preparation method thereof. Background technique [0002] Astaxanthin (Astaxanthin, 3,3'-dihydroxy-4,4'-dione-β,β'-carotene), also known as astaxanthin, is a carotenoid derived from non-vitamin A and belongs to terpene Class of unsaturated compounds, the structural formula is as (III). [0003] [0004] Astaxanthin has many functions such as coloring, anti-oxidation, photoprotection, prevention of myocardial damage, cancer and other chronic diseases, and has attracted the attention of domestic and foreign food, medicine, cosmetics, aquaculture and other industries. However, astaxanthin has multiple isoprene units in its structure, which reduces its polarity and makes it extremely difficult to dissolve in water, which greatly limits its research and application in aqueous solutions. At the same ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08G65/332C08G65/48A23K20/105A23L5/44A23L33/10
CPCA23V2002/00C08G65/3324C08G65/48A23V2200/044A23V2200/30
Inventor 薛长湖张婷徐杰刘炎峻王玉明李兆杰王静凤
Owner OCEAN UNIV OF CHINA