CN111568858A - Preparation method of astaxanthin water solution - Google Patents

Preparation method of astaxanthin water solution Download PDF

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Publication number
CN111568858A
CN111568858A CN202010364701.9A CN202010364701A CN111568858A CN 111568858 A CN111568858 A CN 111568858A CN 202010364701 A CN202010364701 A CN 202010364701A CN 111568858 A CN111568858 A CN 111568858A
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astaxanthin
water
solution
organic solvent
preparation
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刘辉
曾洁琳
张孟坡
陈晓东
杨安平
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Foshan University
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
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    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • A—HUMAN NECESSITIES
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    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
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    • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

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Abstract

The invention discloses a preparation method of an astaxanthin water solution, which comprises the steps of firstly, uniformly mixing astaxanthin, an organic solvent and an emulsifier, and removing the organic solvent after fully stirring; then adding a chelating agent and stirring with a certain amount of water to obtain the astaxanthin water solution. The astaxanthin water solution overcomes the defect of poor water solubility of astaxanthin, and compared with the prior art of preparing nano-emulsion and the like, the astaxanthin water solution has the advantages of mild preparation conditions, safety, environmental protection, simple method and low preparation cost, and avoids the damage to the structure of the astaxanthin; meanwhile, the astaxanthin aqueous solution prepared by the method is easy to be absorbed by organisms, has high bioavailability and good stability, and effectively improves the oxidation resistance of the astaxanthin in application.

Description

Preparation method of astaxanthin water solution
Technical Field
The invention belongs to the technical field of astaxanthin application, and particularly relates to a preparation method of an astaxanthin aqueous solution.
Background
Astaxanthin is a natural super-strong antioxidant derived from algae plants, is used as a novel cosmetic raw material, not only ensures the requirements of people on the efficacy of cosmetics, but also meets the requirements of people on pure nature of the raw material, and can be widely applied to the industries of medicines and foods.
However, astaxanthin is a carotenoid, is insoluble in water, is unstable in property and low in bioavailability, so that the application of astaxanthin is greatly limited, and in order to improve the bioavailability and the water solubility of astaxanthin, the astaxanthin is reported to be prepared into dosage forms such as nanoemulsion (CN 104042568A), self-microemulsion (CN 110693945A), solid self-microemulsion (CN 109985008A), nanoliposome (CN 110558435A) and emulsion (CN 110742862A), but the preparation process of the dosage forms is complicated, the content of astaxanthin is low, the operation process needs nitrogen protection, high temperature, freeze drying, rapid stirring and other processes, the cost is high, and the structure of astaxanthin is damaged.
Disclosure of Invention
The invention aims to solve the technical problems, and specifically adopts the following technical scheme:
a preparation method of an astaxanthin aqueous solution comprises the following steps:
step one, uniformly mixing astaxanthin, an organic solvent and an emulsifier, fully stirring until the mixture is completely transparent, and then removing the organic solvent to obtain a solution A;
and step two, adding a chelating agent and water into the solution A, and stirring to obtain an astaxanthin water solution.
Because astaxanthin is fat-soluble substance and has poor water solubility, the astaxanthin and the emulsifier are fully mixed by adding the organic solvent, and the organic solvent has certain damage to human body, so the astaxanthin is removed in the later period; and then adding a chelating agent to increase the dispersion uniformity of the astaxanthin and increase the dissolution degree of the astaxanthin mixed with the water, and to improve the oxidation resistance of the astaxanthin product, and finally adding a certain amount of water to stir to obtain a clear and transparent astaxanthin water solution.
In some preferred embodiments, the organic solvent is at least one of acetone, dichloromethane and chloroform when the astaxanthin aqueous solution is prepared.
In some preferred embodiments, in preparing the above astaxanthin aqueous solution, the emulsifier is at least one of tween 60, tween 80, sorbitol trioleate, ethylene glycol fatty acid ester, glycerol monostearate and polyoxyethylene nonylphenol ether.
In some preferred embodiments, the chelating agent is at least one of ethylenediaminetetraacetic acid, nitrilotriacetic acid, N-hydroxyethylethylenediaminetriacetic acid, and sodium thiosulfate in the preparation of the above-described aqueous astaxanthin solution.
In some preferred embodiments, in the preparation of the aqueous astaxanthin solution, the organic solvent is removed by drying under reduced pressure in step one.
In some preferred embodiments, the ratio of astaxanthin to organic solvent in preparing the aqueous astaxanthin solution is 1 mg: 0.02-5 mL.
In some preferred embodiments, the ratio of astaxanthin to emulsifier in preparing the aqueous astaxanthin solution is 1 mg: 1-10 mL.
In some preferred embodiments, the ratio of astaxanthin to the chelating agent in preparing the aqueous astaxanthin solution is 1 mg: 1-6 mL.
In some preferred embodiments, the ratio of the emulsifier to the water is 1: 1-10 by volume when the astaxanthin aqueous solution is prepared.
The invention has the beneficial effects that: the astaxanthin water solution overcomes the defect of poor water solubility of astaxanthin, and compared with the prior art of preparing nano-emulsion and the like, the astaxanthin water solution has the advantages of mild preparation conditions, safety, environmental protection, simple method and low preparation cost, and avoids the damage to the structure of the astaxanthin; meanwhile, the astaxanthin aqueous solution prepared by the method is easy to be absorbed by organisms, has high bioavailability and good stability, and effectively improves the oxidation resistance of the astaxanthin in application.
Drawings
FIG. 1 is an HPLC chromatogram of a methanol solution of astaxanthin;
FIG. 2 shows the results of the stability test of the aqueous solution of astaxanthin obtained in example 3 at 50 ℃;
FIG. 3 shows the results of the stability test of the aqueous solution of astaxanthin obtained in example 3 at 70 ℃;
FIG. 4 shows the results of the stability test of the aqueous solution of astaxanthin obtained in example 3 at 90 ℃;
FIG. 5 shows the stability test results of the astaxanthin aqueous solution prepared in example 1 at 70 ℃;
FIG. 6 shows the results of the stability test of the aqueous astaxanthin solution prepared in example 2 at 70 ℃.
Detailed Description
The concept and technical effects of the present invention will be clearly and completely described in the following embodiments to fully understand the objects, aspects and effects of the present invention. It should be noted that the embodiments and features of the embodiments in the present application may be combined with each other without conflict.
Example 1:
a preparation method of an astaxanthin aqueous solution comprises the following steps:
dissolving 0.2g of astaxanthin powder in 40mL of dichloromethane, fully stirring, adding 200mL of Tween 80, uniformly mixing, fully stirring until the mixture is completely transparent, and then drying under reduced pressure to remove the dichloromethane to obtain a solution A;
adding 40mL of ethylenediamine tetraacetic acid and 200mL of deionized water into the solution A, and fully stirring to obtain a clear and transparent astaxanthin water solution.
Example 2:
a preparation method of an astaxanthin aqueous solution comprises the following steps:
dissolving 0.1g of astaxanthin powder in 10mL of dichloromethane, fully stirring, adding 100mL of glyceryl monostearate, uniformly mixing, fully stirring until the mixture is completely transparent, and then drying under reduced pressure to remove the dichloromethane to obtain a solution A;
and adding 100mL of ethylenediamine tetraacetic acid and 100mL of deionized water into the solution A, and fully stirring to obtain a clear and transparent astaxanthin water solution.
Example 3:
a preparation method of an astaxanthin aqueous solution comprises the following steps:
dissolving 0.2g of astaxanthin powder in 200mL of dichloromethane, fully stirring, adding 1L of sorbitol trioleate, uniformly mixing, fully stirring until the mixture is completely transparent, and then drying under reduced pressure to remove the dichloromethane to obtain a solution A;
and adding 200mL of ethylenediamine tetraacetic acid and 1L of deionized water into the solution A, and fully stirring to obtain a clear and transparent astaxanthin water solution.
Example 4:
the stability of the aqueous solution of astaxanthin according to the invention was verified experimentally as follows:
preparation of astaxanthin standard curve
Weighing high-purity astaxanthin reference substances (prepared before a laboratory) to prepare the astaxanthin reference substance methanol solution. Sucking astaxanthin reference substance initial solution 0.5 mL, 1.0 mL, 2.0 mL, 3.0 mL, 4.0mL with pipette, placing in 10mL volumetric flask, metering volume with methanol, mixing, filtering with 0.45 μm filter membrane to obtain filtrate, detecting astaxanthin peak area under chromatographic conditions of mobile phase methanol-water (95:5), absorption wavelength 474nm, flow rate 1mL/min, column temperature 35 deg.C, and sample injection amount 20 μ L, taking astaxanthin peak area as ordinate, and astaxanthin concentration as astaxanthin concentrationOn the abscissa, regression is performed to obtain the equation Y3061X +19117R20.9988. The liquid phase diagram of 0.2mg/mL astaxanthin in methanol is shown in FIG. 1.
Secondly, the content of the astaxanthin in the astaxanthin water solution is changed under the conditions of different temperatures and different heating times
(1) Stability at 50 deg.C
The astaxanthin aqueous solution prepared in example 3 is respectively put into 12 10mL penicillin bottles, the concentration of the astaxanthin in the astaxanthin aqueous solution is firstly measured (according to the regression equation), then the penicillin bottles containing the astaxanthin aqueous solution are sealed and heated under the condition of a water bath at 50 ℃, then 3 penicillin bottles are respectively taken when the penicillin bottles are respectively heated for 16h, 32 h, 48 h and 64h, the penicillin bottles are cooled for 5min under ice water, 1mL of the astaxanthin aqueous solution is respectively taken and added with 9mL of methanol, sealed ultrasonic treatment is carried out for 5min, and the mixture is filtered by a 0.45-micron filter membrane and then is subjected to liquid phase content measurement.
(2) Stability at 70 deg.C
The astaxanthin aqueous solution prepared in the example 3 is respectively put into 12 penicillin bottles with the volume of 10mL, the concentration of the astaxanthin is firstly measured, then the penicillin bottles with the astaxanthin aqueous solution are sealed and heated in a water bath condition with the temperature of 70 ℃, then 3 penicillin bottles are respectively taken when the penicillin bottles are respectively heated for 4h, 8h, 12 h and 16h, the penicillin bottles are cooled for 5min under ice water, 1mL of the astaxanthin aqueous solution is respectively taken, 9mL of methanol is added, closed ultrasonic treatment is carried out for 5min, the mixture is filtered through a 0.45 mu m filter membrane, and then the liquid phase is fed for content measurement.
The same operation was carried out for the astaxanthin aqueous solution prepared in example 1-2.
(3) Stability at 90 deg.C
The astaxanthin aqueous solution prepared in the example 3 is respectively put into 12 penicillin bottles with the volume of 10mL, the concentration of the astaxanthin is firstly measured, then the penicillin bottles with the astaxanthin aqueous solution are sealed and heated in a water bath condition with the temperature of 90 ℃, then 3 penicillin bottles are respectively taken when the penicillin bottles are respectively heated for 2 hours, 4 hours, 6 hours and 8 hours, the penicillin bottles are cooled for 5 minutes under ice water, 1mL of the astaxanthin aqueous solution is respectively taken and added with 9mL of methanol, closed ultrasonic treatment is carried out for 5 minutes, the mixture is filtered through a 0.45 mu m filter membrane, and then the liquid phase is fed for content measurement.
Third, experimental results
The above results are shown in fig. 2 to 6, and the results show that after the astaxanthin aqueous solution prepared by the invention is heated for 64 hours at 50 ℃, for 16 hours at 70 ℃ and for 4 hours at 90 ℃, the astaxanthin content (the ratio of the astaxanthin concentration measured after heating to the astaxanthin concentration measured before heating) is more than 90%, which indicates that the astaxanthin aqueous solution prepared by the invention has higher stability.

Claims (9)

1. A preparation method of an astaxanthin aqueous solution is characterized by comprising the following steps:
step one, uniformly mixing astaxanthin, an organic solvent and an emulsifier, fully stirring until the mixture is completely transparent, and then removing the organic solvent to obtain a solution A;
and step two, adding a chelating agent and water into the solution A, and stirring to obtain an astaxanthin water solution.
2. The method according to claim 1, wherein the organic solvent is at least one of acetone, dichloromethane, and chloroform.
3. The method according to claim 1, wherein the emulsifier is at least one selected from the group consisting of tween 60, tween 80, sorbitan trioleate, ethylene glycol fatty acid ester, glycerol monostearate and polyoxyethylene nonylphenol ether.
4. The method according to claim 1, wherein the chelating agent is at least one of ethylenediaminetetraacetic acid, nitrilotriacetic acid, N-hydroxyethylethylenediaminetriacetic acid, and sodium thiosulfate.
5. The method according to claim 1, wherein in the first step, the organic solvent is removed by drying under reduced pressure.
6. The method according to claim 1, wherein the ratio of astaxanthin to the organic solvent is 1 mg: 0.02-5 mL.
7. The method according to claim 1, wherein the ratio of astaxanthin to emulsifier is 1 mg: 1-10 mL.
8. The method according to claim 1, wherein the ratio of astaxanthin to the chelating agent is 1 mg: 1-6 mL.
9. The preparation method according to claim 1, wherein the volume ratio of the emulsifier to the water is 1:1 to 10.
CN202010364701.9A 2020-04-30 2020-04-30 Preparation method of astaxanthin water solution Pending CN111568858A (en)

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CN110140958A (en) * 2019-04-19 2019-08-20 浙江清荣生物科技发展有限公司 A kind of astaxanthin oral solution and preparation method thereof
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