CN114306103A - High-stability lutein protective emulsion and preparation method thereof - Google Patents
High-stability lutein protective emulsion and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a high-stability lutein protective emulsion and a preparation method thereof. The alkali xylan is subjected to homogeneous reaction with an acetylation reagent in a metal salt organic solvent according to a proper solid-liquid ratio and purified to obtain an acetylated xylan emulsifier; fully dispersing the acetylated xylan emulsifier in water, mixing the acetylated xylan emulsifier with the lutein oil solution in a proper proportion, and homogenizing to obtain the lutein protective emulsion. The invention adopts homogeneous reaction to obtain the acetylated xylan with evenly distributed acetyl groups, and the proper acetylation degree ensures that the xylan has good hydrophilic-hydrophobic balance, so that the xylan can be well dispersed in water and can be stably adsorbed on an oil-water interface to form a stable barrier film, thereby protecting lutein in an oil phase from being oxidized and degraded. The emulsifier has the advantages of degradability, environmental protection, low cost, simple preparation process, mild preparation conditions, strong biocompatibility, higher emulsifying property, higher lutein protection effect and the like.
Description
Technical Field
The invention belongs to the field of biomass refining and emulsification, and particularly relates to a high-stability lutein protective emulsion and a preparation method thereof.
Background
Hemicellulose is a plant source polysaccharide with abundant reserves, is used as low-quality energy to be burnt in most wastes in industries such as pulping and papermaking, forestry felling and processing, crop planting and processing and the like, is used for producing small-molecular chemicals only in a small scale, and causes huge resource waste. Xylan is a typical hemicellulose, and a part of hydroxyl groups on a sugar ring of xylan are replaced by acetyl groups in a native state, so that molecules of xylan have amphipathy consisting of a hydrophilic chain segment and a hydrophobic chain segment. However, in the conventional alkaline extraction process, acetyl groups on xylan are easily removed, and the natural amphipathy of xylan is damaged. Acetyl is uniformly introduced into the alkali extraction xylan molecular chain and the substitution degree of the alkali extraction xylan molecular chain is regulated by a chemical derivatization method, so that the xylan molecular chain can be endowed with more excellent amphiphilic performance. The acetylated xylan with excellent amphiphilicity can realize higher adsorption concentration on an oil-water interface, thereby playing a good role in blocking an oil phase and protecting substances in the oil phase. Lutein is a fat-soluble antioxidant active substance, is mainly applied to the fields of health food and cosmetics, has high light and oxygen sensitivity, and is extremely easy to be oxidized and inactivated in the delivery process, so that a proper coating means is needed for reducing the oxidation of lutein. Common coating means include the construction of microcapsules and oil-water emulsion oil phase protection, the former requiring complex structural design and specific lutein release conditions, while the protective effect of the latter depends largely on the condition of the emulsifier. Compared with other commercial emulsifiers, particularly common petroleum-based emulsifiers, the acetylated xylan has the characteristics of no toxicity, no harm, natural biocompatibility and excellent amphiphilic property, and the barrier effect of the acetylated xylan can greatly reduce the permeation of ultraviolet light and oxygen, so that the acetylated xylan is advocated to be used as an efficient oil-water emulsifier for preparation and stabilization of lutein protective emulsion.
Disclosure of Invention
In order to prepare the natural polymer emulsifier with low cost and excellent emulsifying property, reduce the oxidative degradation phenomenon of lutein and other drugs in the delivery process and improve the biocompatibility of a cosmetic product containing the lutein protective emulsion, the invention mainly aims to provide the preparation method of the high-stability lutein protective emulsion, and the method has the advantages of environmental friendliness, low cost, simple preparation process and mild preparation conditions.
The invention also aims to provide a high-stability lutein protective emulsion prepared by the method.
The purpose of the invention is realized by the following technical scheme:
the preparation method of the acetylated xylan emulsifier and the high-stability lutein protective emulsion provided by the invention comprises the steps of carrying out homogeneous reaction on alkali xylan and an acetylation reagent in a metal salt organic solvent according to a proper solid-liquid ratio; mixing the reaction solution after the reaction with an alcohol organic solvent to obtain a precipitate, and separating the precipitate to obtain an acetylated xylan component with uniform acetyl distribution; dispersing an acetylated xylan component having a uniform acetyl distribution as an emulsifier in water, and dissolving lutein in an oil phase at an appropriate concentration; and finally, mixing the acetylated xylan aqueous dispersion and the lutein oil solution in a proper oil-water ratio, and mechanically homogenizing to obtain the acetylated xylan emulsified lutein protective emulsion.
A preparation method of a high-stability lutein protective emulsion comprises the following steps:
(1) dissolving alkali xylan in a metal salt solution, adjusting the pH value of the system to 5.0-9.0, adding an acetylation reagent, reacting at 40-90 ℃ for 1-3 hours, finishing the reaction, and purifying to obtain acetylated xylan;
(2) mixing lutein with an oil phase to obtain a lutein oil solution, dispersing the acetylated xylan in the step (1) in water to form an acetylated xylan dispersion, mixing the lutein oil solution and the acetylated xylan dispersion, and homogenizing to obtain the high-stability lutein protective emulsion.
Preferably, the alkali xylan in the step (1) is at least one of hardwood, straw, wheat straw, rice hull, bagasse, corn cob, corn stalk and oil tea fruit shell. The alkali xylan wood stocks have a low degree of branching.
Preferably, the ratio of the oven-dry mass of the alkali xylan of the step (1) to the volume of the alkali liquor is 1 g: 8 mL-1 g: 20mL of the preparation.
Preferably, the reagent for adjusting the pH in the step (1) is an organic base and/or an organic acid, and specifically at least one of triethylamine, liquid ammonia, glacial acetic acid and glutaric acid.
Preferably, the solid-to-liquid ratio of the alkali xylan to the metal salt solution in the step (1) is 1: 10-1: 100; more preferably 1: 12-1: 20; the concentration of the metal salt solution is 0.1-1 wt%.
Preferably, in the metal salt solution in step (1), the metal salt is at least one of sodium chloride, lithium chloride, sodium bromide and lithium bromide, and the solvent is at least one of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide and tetrahydrofuran.
Preferably, the acetylation reagent in step (1) is at least one of acetyl chloride, acetic anhydride and glacial acetic acid; the mass ratio of the alkali xylan to the acetylation reagent is 10: 1-20: 1.
preferably, the stirring speed of the reaction in the step (1) is 200-500 rpm.
Preferably, the purification method in step (1) is: adding the reaction product mixed solution into an alcohol organic solvent, taking the precipitate, washing the precipitate with the alcohol organic solvent, drying and grinding to obtain acetylated xylan powder; at least one of the ethanol, propanol and butanediol; the volume ratio of the reaction product mixed liquid to the alcohol organic solvent is 1: 1-1: 5.
Preferably, the quality concentration of the lutein oil solution in the step (2) is 0.1-0.5 wt%; the oil phase is at least one of dodecane, tetradecane, hexadecane, soybean oil, and triglycerides.
Preferably, the solid content of the acetylated xylan dispersion in the step (2) is 0.5 to 5 wt%.
Preferably, the mass ratio of the acetylated xylan dispersion in the step (2) to the oil phase is 9: 1-2: 1.
preferably, the homogenization treatment in the step (2) is one of ultrasonic treatment, high-speed homogenization and high-pressure homogenization; the unit volume power density of the homogenization treatment is 10-20W/mL, and the time is 20-40 min.
Preferably, the acetylated xylan in the step (2) needs to be subjected to ultrasonic treatment after being dispersed in water, the power density per unit volume of the ultrasonic treatment is 10-20W/mL, and the time is 20-40 min.
The high-stability lutein protective emulsion prepared by the method.
The acetylated xylan emulsifier provided by the invention is solid powder with structural amphipathy and good dispersibility, the solid powder is fully dispersed in an aqueous solution to form a stable dispersion solution, and the stable dispersion solution is mixed with a lutein oil solution in proportion and then mechanically homogenized to prepare the acetylated xylan lutein protective emulsion.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) in the preparation method provided by the invention, the process of acetylation of alkali xylan can realize the control of the amphipathy of xylan molecular chains and promote the amphipathy balance of acetylated xylan.
(2) The acetylated xylan emulsifier with evenly distributed acetyl groups prepared by the invention has good water dispersibility and balanced amphipathy, can be well dispersed in water, and can be stably adsorbed on an oil-water interface to form a stable barrier film, so that lutein in an oil phase is protected from being oxidized and degraded, and the stability of the acetylated xylan serving as the emulsifier to the lutein protective emulsion is improved.
(3) The acetylated xylan emulsifier prepared by the invention has the advantages of degradability, environmental protection, low cost, simple preparation process, mild preparation conditions, strong biocompatibility, higher emulsifying property, higher lutein protection effect and the like.
Drawings
FIG. 1 is a graph of the effect of lutein emulsions prepared from the acetylated xylan dispersions of examples 1-3 with 1.0 wt%, 2.0 wt% and 4.0 wt% solids after standing for 7 days.
FIG. 2 shows the lutein emulsion of example 1 at 15W/m2Is (a) retention of lutein upon continuous irradiation at an ultraviolet lamp (about two orders of magnitude higher than the solar radiation power at the equator), wherein MCT is lutein emulsion prepared in pure oil phase, T80 is lutein emulsion prepared with tween 80 as an emulsifier and other conditions the same as in example, AX is lutein emulsion prepared in example.
FIG. 3 is the lutein emulsion of example 2 at 15W/m2Under an ultraviolet lamp for 0h and 48h continuously, demulsifying with ethanol and diluting to 100 times.
Detailed Description
The present invention will be described in further detail with reference to examples and drawings, but the embodiments of the present invention are not limited thereto.
Those who do not specify specific conditions in the examples of the present invention follow conventional conditions or conditions recommended by the manufacturer. The raw materials, reagents and the like which are not indicated for manufacturers are all conventional products which can be obtained by commercial purchase.
Example 1
Preparing a lithium chloride dimethyl sulfoxide solution with the concentration of 1 wt%, weighing bagasse alkali xylan (dried in air at the temperature of 25 ℃ and RH of 50 g) with the air-dried mass of 10g and the lithium chloride dimethyl sulfoxide solution (with the concentration of 1 wt%) according to the solid-to-liquid ratio of 1: 12 (m: v, unit is g/mL), adjusting the pH of the system to 7 by using triethylamine and glacial acetic acid, adding 1g of acetyl chloride, and stirring and reacting for 3 hours at 50 ℃ and 200 rpm; after the reaction is finished, cooling the reaction solution to room temperature, adding the reaction solution into absolute ethyl alcohol (the volume ratio of the reaction solution to the absolute ethyl alcohol is 1: 3) to precipitate the acetylated xylan, standing for more than 6 hours, and then carrying out solid-liquid separation on the acetylated xylan by adopting a centrifugal method; and continuously washing the separated acetylated xylan precipitate for more than three times by using an ethanol solution with the volume percentage concentration of 70%, placing the ethanol solution in a ventilation place to volatilize ethanol, and drying to obtain the acetylated xylan.
Weighing 1g of the extracted acetylated xylan, dispersing the acetylated xylan in deionized water to prepare 100mL of dispersion liquid with the concentration of 1 wt%, and continuously treating the acetylated xylan dispersion liquid for more than 30min by using an ultrasonic probe under the ice bath condition at the power mixing liquid volume ratio of 10W/mL to obtain uniformly dispersed acetylated xylan dispersion liquid (namely the acetylated xylan emulsifier); dissolving 0.3g lutein in 100mL triglyceride to prepare lutein oil solution; the acetylated xylan dispersion obtained was mixed with a lutein oil solution at a ratio of 4: 1, and carrying out primary mixing at 300rpm for 3 min; and (3) mechanically treating 100mL of the mixed oil-water mixed solution by using an ultrasonic probe, wherein the power density of the treated unit volume is 15W/mL, the treatment time is 30min, and carrying out ultrasonic treatment again at an interval of 5s every 5s until the ultrasonic treatment is accumulated for 30min to obtain the stable acetylated xylan emulsion (figure 1).
Example 2
Preparing a lithium chloride N, N-dimethylformamide solution with the concentration of 0.5 wt%, weighing bagasse alkali xylan with the air-dried mass of 20g (air-dried in air at the temperature of 25 ℃ and RH of 40%) and a lithium bromide N, N-dimethylformamide solution (with the concentration of 0.5 wt%) according to the solid-to-liquid ratio of 1: 20 (m: v, unit is g/mL), adjusting the pH of the system to 6 by using liquid ammonia and glutaric acid, adding 1g of acetic anhydride, and stirring and reacting at 50 ℃ and 200rpm for 2 hours; after the reaction is finished, cooling the reaction solution to room temperature, adding the reaction solution into anhydrous methanol (the volume ratio of the reaction solution to the anhydrous methanol is 1: 4) to precipitate the acetylated xylan, standing for more than 6 hours, and then carrying out solid-liquid separation on the acetylated xylan by adopting a centrifugal method; and continuously washing the separated acetylated xylan precipitate for more than three times by using a methanol solution with the volume percentage concentration of 70%, placing the precipitate in a ventilation place to volatilize methanol, and drying to obtain the acetylated xylan.
Weighing 2g of the extracted acetylated xylan, dispersing the acetylated xylan in deionized water to prepare 100mL of dispersion liquid with the concentration of 2 wt%, and continuously treating the acetylated xylan dispersion liquid for more than 30min at the power density of 10W/mL under the ice bath condition by using an ultrasonic probe to obtain uniformly dispersed acetylated xylan dispersion liquid (namely the acetylated xylan emulsifier); dissolving 0.1g lutein in 100mL soybean oil to prepare lutein oil solution; the acetylated xylan dispersion obtained was mixed with a lutein oil solution at a ratio of 5: 1, and carrying out primary mixing at 300rpm for 3 min; and (3) mechanically treating 100mL of the mixed oil-water mixed solution by using an ultrasonic probe, wherein the unit volume power density of the treatment is 20W/mL, the treatment time is 30min, and carrying out ultrasonic treatment again at an interval of 5s every 5s until the ultrasonic treatment is accumulated for 30min to obtain the stable lutein protective emulsion (figure 1).
Example 3
Preparing a sodium chloride tetrahydrofuran solution with the concentration of 0.5 wt%, weighing 10g of bagasse alkali xylan (dried in air at the temperature of 25 ℃ and RH of 60) and the sodium chloride tetrahydrofuran solution (with the concentration of 0.5 wt%) in an air-dried mass, wherein the solid-to-liquid ratio is 1: 30 (m: v, unit is g/mL), adjusting the pH of the system to 5 by using triethylamine and glacial acetic acid, adding 1g of glacial acetic acid, and stirring and reacting for 1h at 60 ℃ and 200 rpm; after the reaction is finished, cooling the reaction liquid to room temperature, adding the reaction liquid into anhydrous propanol (the volume ratio of the reaction liquid to the anhydrous propanol is 1: 5) to precipitate the acetylated xylan, standing for more than 6 hours, and then carrying out solid-liquid separation on the acetylated xylan by adopting a centrifugal method; and continuously washing the separated acetylated xylan precipitate for more than three times by using a propanol solution with the volume percentage concentration of 70%, placing the precipitate in a ventilation place to volatilize propanol, and drying to obtain the acetylated xylan.
Weighing 4.0g of the extracted acetylated xylan, dispersing the acetylated xylan in deionized water to prepare 100mL of dispersion liquid with the concentration of 4 wt%, and continuously treating the acetylated xylan dispersion liquid for more than 30min at the power density of 10W/mL under the ice bath condition by using an ultrasonic probe to obtain uniformly dispersed acetylated xylan dispersion liquid (namely the acetylated xylan emulsifier); dissolving 0.5g lutein in 100mL soybean oil to prepare lutein oil solution; the acetylated xylan dispersion obtained was mixed with a lutein oil solution at a ratio of 3: 1, and carrying out primary mixing at 300rpm for 3 min; and (3) mechanically treating 100mL of the mixed oil-water mixed solution by using an ultrasonic probe, wherein the unit volume power density of the treatment is 10W/mL, the treatment time is 30min, and carrying out ultrasonic treatment again at an interval of 5s every 5s until the ultrasonic treatment is accumulated for 30min to obtain the stable lutein protective emulsion (figure 1).
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (10)
1. A preparation method of a high-stability lutein protective emulsion is characterized by comprising the following steps:
(1) dissolving alkali xylan in a metal salt solution, adjusting the pH value of the system to 5.0-9.0, adding an acetylation reagent, reacting at 40-90 ℃ for 1-3 hours, finishing the reaction, and purifying to obtain acetylated xylan;
(2) mixing lutein with an oil phase to obtain a lutein oil solution, dispersing the acetylated xylan in the step (1) in water to form an acetylated xylan dispersion, mixing the lutein oil solution and the acetylated xylan dispersion, and homogenizing to obtain the high-stability lutein protective emulsion.
2. The method for preparing a high stable lutein protective emulsion according to claim 1, wherein the acetylation reagent of step (1) is at least one of acetyl chloride, acetic anhydride and glacial acetic acid; the mass ratio of the alkali xylan to the acetylation reagent is 10: 1-20: 1.
3. the preparation method of the high-stability lutein protective emulsion according to claim 1, wherein the solid-to-liquid ratio of the alkali xylan and the metal salt solution in the step (1) is 1:10 to 1: 100; the concentration of the metal salt solution is 0.1-1 wt%; in the metal salt solution, the metal salt is at least one of sodium chloride, lithium chloride, sodium bromide and lithium bromide.
4. The method for preparing a high-stability lutein protective emulsion according to claim 1, wherein the quality concentration of the lutein oil solution in the step (2) is 0.1-0.5 wt%; the solid content of the acetylated xylan dispersion is 0.5-5 wt%; the mass ratio of the acetylated xylan dispersion to the oil phase is 9: 1-2: 1.
5. the method for preparing a high stable lutein protective emulsion according to claim 1, wherein the oil phase in step (2) is at least one of dodecane, tetradecane, hexadecane, soybean oil and triglyceride.
6. The method for preparing a high stable lutein protective emulsion according to claim 1, wherein the reagent for adjusting pH in step (1) is at least one of organic base and/or organic acid, specifically triethylamine, liquid ammonia, glacial acetic acid and glutaric acid.
7. The method for preparing a high stable lutein protective emulsion according to claim 1, wherein the homogenizing treatment in step (2) is one of ultrasonic treatment, high speed homogenization and high pressure homogenization; the unit volume power density of the homogenization treatment is 10-20W/mL, and the time is 20-40 min.
8. The method for preparing a highly stable lutein protective emulsion according to claim 1, wherein the raw material of the alkali xylan of step (1) is at least one of broadleaf wood, rice straw, wheat straw, rice hull, bagasse, corn cob, corn stalk and oil tea fruit shell;
the alkali xylan in the step (1) is prepared by mixing the following components in parts by volume of alkali liquor according to the ratio of the absolute dry mass of a wood fiber raw material to the volume of the alkali liquor of 1 g: 8 mL-1 g: 20mL of the preparation.
9. The method for preparing a highly stable lutein protective emulsion according to claim 1, wherein the solvent of the metal salt solution of step (1) is at least one of N, N-dimethylformamide, N-dimethylacetamide, dimethylsulfoxide and tetrahydrofuran; the stirring speed of the reaction in the step (1) is 200-500 rpm;
the purification method in the step (1) comprises the following steps: adding the reaction product mixed solution into an alcohol organic solvent, taking the precipitate, washing the precipitate with the alcohol organic solvent, drying and grinding to obtain acetylated xylan powder; at least one of the ethanol, propanol and butanediol; the volume ratio of the reaction product mixed solution to the alcohol organic solvent is 1: 1-1: 5;
and (3) carrying out ultrasonic treatment after the acetylated xylan is dispersed in water, wherein the power density per unit volume of the ultrasonic treatment is 10-20W/mL, and the time is 20-40 min.
10. A high stable lutein protective emulsion obtained by the method of any one of claims 1 to 9.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN115282085A (en) * | 2022-08-31 | 2022-11-04 | 华南理工大学 | Application of acetylated xylan as functional additive in cosmetics |
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| US5430142A (en) * | 1993-08-06 | 1995-07-04 | The Center For Innovative Technology | Thermoplastic pentosan-rich polysaccharides from biomass |
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