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Astaxanthin methoxy polyethylene glycol acetate and preparation method thereof

A technology of methoxy polyethylene glycol and astaxanthin acetate, applied in the field of methoxy polyethylene glycol astaxanthin acetate and preparation thereof, can solve the problem of poor water dispersibility, inability to fully play a role, and astaxanthin It is easy to aggregate and other problems, and achieves the effects of mild reaction conditions, good water solubility and simple process.

Active Publication Date: 2019-09-10
OCEAN UNIV OF CHINA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem to be solved by the present invention is that astaxanthin is easy to gather and its water dispersibility is poor, so it cannot fully play its role

Method used

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  • Astaxanthin methoxy polyethylene glycol acetate and preparation method thereof
  • Astaxanthin methoxy polyethylene glycol acetate and preparation method thereof
  • Astaxanthin methoxy polyethylene glycol acetate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Synthesis: 40mg of free astaxanthin, 1 times the molar amount of methoxypolyethylene glycol acetic acid (mPEG-CM, molecular weight about 2000), 200mg of DMAP, put into a 100ml serum bottle, add 30ml of dichloromethane and stir to dissolve; nitrogen, protected from light, and shaken for 12 hours in a constant temperature incubator (100 rpm / min) at 37°C. The synthesis rate of mPEG-CM@AST can reach 90.62%.

[0035]Purification: remove the organic solvent by rotary evaporation under reduced pressure, redissolve with 80ml of dichloromethane, wash with 200ml of hydrochloric acid solution (1mol / l), 200ml of saturated sodium bicarbonate solution, and 200ml of saturated sodium chloride solution for 3 times in sequence; anhydrous sulfuric acid Sodium in addition to water. The organic phase was recovered and rotary evaporated to dryness to obtain a crude product. A small amount of the crude product was removed and redissolved in chromatographically pure dichloromethane for TLC an...

Embodiment 2

[0037] Synthesis: 80mg of free astaxanthin, 1 times the molar amount of methoxypolyethylene glycol acetic acid (mPEG-CM, molecular weight about 2000), 150mg of EDCI, put into a 100ml serum bottle, add 25ml of acetone, fill with nitrogen, and avoid light , shaking in a constant temperature incubator (100rpm / min) at 30°C for 6h.

[0038] Purification: remove the organic solvent by rotary evaporation under reduced pressure, redissolve with 120ml of dichloromethane, wash with 350ml of hydrochloric acid solution (1mol / l), 350ml of saturated sodium bicarbonate solution, and 350ml of saturated sodium chloride solution for 3 times in sequence; anhydrous sulfuric acid Sodium in addition to water. The organic phase was recovered and rotary evaporated to dryness to obtain a crude product. A small amount of the crude product was removed and redissolved in chromatographically pure dichloromethane for TLC and HPLC detection.

Embodiment 3

[0040] Synthesis: 40mg of free astaxanthin, 4 times the molar amount of methoxypolyethylene glycol acetic acid (mPEG-CM, molecular weight about 5000), 250mg of triethylamine, put into a 100ml serum bottle, add 35ml of ethyl acetate, fill nitrogen, protected from light, and shaken for 18 hours in a constant temperature incubator (100 rpm / min) at 25°C.

[0041] Purification: Remove the organic solvent by rotary evaporation under reduced pressure, then redissolve with 200ml of dichloromethane, wash with 450ml of hydrochloric acid solution (1mol / l), 450ml of saturated sodium bicarbonate solution, and 450ml of saturated sodium chloride solution for 3 times in sequence; anhydrous sulfuric acid Sodium in addition to water. The organic phase was recovered and rotary evaporated to dryness to obtain a crude product. A small amount of the crude product was removed and redissolved in chromatographically pure dichloromethane for TLC and HPLC detection.

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Abstract

The invention relates to the technical field of astaxanthin processing and preparation, in particular to astaxanthin methoxy polyethylene glycol acetate and a preparation method thereof. A chemicallysynthesized free astaxanthin or a free astaxanthin from natural sources is used as a main skeleton, methoxy polyethylene glycol acetic acid (mPEG-CM) is used as an acyl donor and a hydrophilic group,and astaxanthin methoxy polyethylene glycol acetate with high water solubility is prepared. The prepared mPEG-CM@PEG has solubility of 32 mg / ml in ultrapure water at 25 DEG C, can be used as a feed additive for aquatic products, livestock and poultry, can be used as a food coloring agent, can be used in industries such as pharmaceuticals and cosmetics, and can be used as a functional ingredient for development of health foods. Due to good water solubility of astaxanthin methoxy polyethylene glycol acetate, an application range of astaxanthin is greatly improved.

Description

technical field [0001] The invention relates to the technical field of astaxanthin processing and preparation, in particular to a methoxypolyethylene glycol acetate astaxanthin ester and a preparation method thereof. Background technique [0002] Astaxanthin (AST for short, also known as 3,3'-dimethyl-4,4'-diketone-β, β'-carotene, molecular formula C 40 h 52 o 4 ), is a kind of carotenoid, which has bright red color and strong antioxidant properties, can enhance the body's immunity, promote antibody production, and has the ability to resist oxidation and scavenge free radicals. Due to its strong coloring ability and physiological function activity, astaxanthin has become a research hotspot in the fields of aquaculture, food, medicine and cosmetics at home and abroad in recent years. [0003] Astaxanthin is lipophilic, which greatly limits its functions in capturing active free radicals, quenching singlet oxygen, and inhibiting lipid peroxidation in aqueous solutions. In ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/331
CPCC08G65/3314
Inventor 徐杰杨鲁薛长湖乔星曹云睿李兆杰唐庆娟王玉明
Owner OCEAN UNIV OF CHINA