CN116439372A - High-water-solubility lutein powder and preparation method thereof - Google Patents

High-water-solubility lutein powder and preparation method thereof Download PDF

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Publication number
CN116439372A
CN116439372A CN202210011979.7A CN202210011979A CN116439372A CN 116439372 A CN116439372 A CN 116439372A CN 202210011979 A CN202210011979 A CN 202210011979A CN 116439372 A CN116439372 A CN 116439372A
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lutein
solubility
water
powder
preparation
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宋江峰
罗树伟
李莹
张辰辰
耿宁宁
马恺扬
李大婧
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Jiangsu Academy of Agricultural Sciences
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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
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • 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
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/30—Artificial sweetening agents
    • A23L27/33—Artificial sweetening agents containing sugars or derivatives
    • A23L27/36—Terpene glycosides
    • 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
    • A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
    • A23L29/30—Foods or foodstuffs containing additives; Preparation or treatment thereof containing carbohydrate syrups; containing sugars; containing sugar alcohols, e.g. xylitol; containing starch hydrolysates, e.g. dextrin
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Nutrition Science (AREA)
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  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
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Abstract

The invention discloses high water-solubility lutein powder and a preparation method thereof, which are a process technology for modifying lutein from hydrophobicity to hydrophilicity, and belong to the technical field of processing of nutritional health foods. The lutein and the glucosyl stevioside and hypromellose interact to form a semi-interpenetrating network structure by coupling under specific conditions such as anti-solvent precipitation, dynamic ultrahigh-pressure micro-jet, spray drying and the like, so that the high-water-solubility lutein powder with amorphous form and improved stability is prepared. The apparent solubility of lutein of the product can be increased by more than 5000 times, and the storage stability of lutein is enhanced in a low-temperature light-resistant environment. The preparation method is simple, and has the characteristics of green process conditions, natural raw materials and auxiliary materials and the like.

Description

High-water-solubility lutein powder and preparation method thereof
Technical Field
The invention belongs to the technical field of processing of nutritional health foods, and relates to high-water-solubility lutein powder and a preparation method thereof.
Background
Lutein is a dihydroxycarotenoid whose polyisoprene structure contains ionone ring, and is not only related to neuroprotection and anticancer effect, but also can effectively prevent eye diseases. Lutein, zeaxanthin and meso-zeaxanthin are the primary pigments residing in the macula of the eye for absorbing actinic blue light that may cause peroxidation of retinal lipids. This property is associated with protection against age-related macular degeneration. These unique physiological functions of lutein are increasingly gaining importance in the development of nutritional health foods. However, because lutein is extremely insoluble in water, the application of lutein in liquid preparations such as beverages, oral liquids and other nutritional and healthy products is greatly influenced.
In order to widen the application range of the lutein in the food and pharmaceutical industries, researchers enhance the water solubility of the lutein by combining a solubility promoting substance with a physicochemical method. In the prior patent, a preparation method of alpha-glucosyl hesperidin modified lutein liposome (application number: 201811581803.5) is disclosed, lutein and lipid materials are dissolved to obtain lutein lipid solution, lipid membranes are hydrated, dispersion liquid is obtained after ultrasonic treatment, the alpha-glucosyl hesperidin solution is dropwise added into the dispersion liquid, stirring is carried out at room temperature overnight, and the lutein liposome is obtained after extrusion through a polycarbonate membrane. The preparation process of water soluble lutein powder is disclosed, and includes mixing lutein crystal with low boiling point organic solvent with high solubility to lutein crystal and heating to dissolve to obtain oil phase; mixing the modified starch with water, heating, dissolving and cooling to obtain a water phase; adding the oil phase into the water phase, and emulsifying to obtain a mixed solution; homogenizing with high pressure homogenizer, removing organic solvent in the emulsion system, and removing water in the emulsion by spray drying or spray fluidized bed drying to obtain water-soluble lutein dry powder. Disclosed is a water-soluble lutein granule and its preparing process (application number: 201410791127. X), wherein the water-soluble lutein granule is obtained by passing mixed powder of lutein and water-soluble polymer auxiliary material through supercritical fluid recrystallization equipment. The water-soluble lutein is prepared by adopting a solvent-free decompression melting method, and has the dissolution rate of up to 98 percent, high stability and good dispersibility. Disclosed is a method for preparing water-soluble lutein by low-temperature melt extrusion and the product (application number: 201710295890.7), wherein the water-soluble lutein with high dissolution rate is obtained by mixing lutein with nonionic polymer surfactant and extruding the mixture under a certain condition by a hot melt extruder. Disclosed is a water-soluble lutein emulsion gel and its preparing process (application number: 202010981306.5), wherein corn peptide is dispersed under water-soluble condition for incubation, and modified peptide powder is obtained through vacuum freeze drying; dispersing corn peptide in distilled water, mixing with corn oil containing lutein, homogenizing under high pressure to form coarse emulsion; the lyophilized denatured peptide powder was added to the above crude emulsion and thoroughly mixed to completely hydrate lutein, and further gluconolactone was added and incubated at 25 ℃ to obtain lutein emulsion gel. The invention discloses a green preparation method (application number: 201711178383.1) of water-soluble lutein, which takes lutein as a raw material, wherein the prescription composition and the mass ratio of lutein to stevioside=1:2-1:10, and the water-soluble lutein with high stability and high solubility is obtained by adopting low-frequency ultrasound, high-pressure shearing and natural antioxidant use through non-covalent combination of lutein and stevioside molecules and modification of specific methods and conditions.
The problems of the technology are that 1) the emulsifier and the organic reagent with larger toxicity are used more, the environment pollution is caused, and the prepared water-soluble lutein has harmful reagent residues with different degrees; 2) The obtained water-soluble lutein has an unobvious dissolution promoting effect, and the solution can be subjected to a resolution phenomenon in the storage process; the temperature in the preparation process is higher, and the degradation loss of lutein is easy to cause; 3) Lutein in the obtained product is totally embedded in amphiphilic substances, and the lutein absorption and utilization are limited by the capacity of micelle to release lutein. Therefore, a new green preparation method or process technology is required to be sought, the use of toxic and harmful reagents is reduced while the water solubility is increased, and the water solubility stability and bioavailability of lutein are effectively improved.
Disclosure of Invention
Technical problem
The invention aims to provide water-soluble lutein powder with high water solubility and high stability and a preparation method thereof.
Technical proposal
A high water-solubility lutein powder and a preparation method thereof are characterized in that lutein, glucosyl stevioside and hypromellose molecules are interacted to form a semi-interpenetrating network structure by coupling specific conditions such as anti-solvent precipitation, dynamic ultrahigh-pressure micro-jet, spray drying and the like, so that the high water-solubility lutein powder with amorphous state and improved stability is prepared.
The preparation method of the water-soluble lutein powder comprises the following steps:
(1) Fully dissolving high-purity lutein in absolute ethyl alcohol, then slowly and uniformly adding the high-purity lutein into an aqueous solution containing glucosyl stevioside, hypromellose and natural water-soluble antioxidants under a magnetic stirring state, and stirring for 20-30 minutes at a magnetic stirring rotating speed of 400-600 rpm to obtain a suspension;
(2) Carrying out dynamic ultrahigh pressure micro-jet circulation treatment on the suspension obtained in the step (1) for 3 times at a treatment pressure of 100-150 MPa to obtain a micro-jet homogeneous solution;
(3) And (3) carrying out spray drying on the micro-jet homogeneous solution obtained in the step (2), controlling the air inlet temperature to be 180 ℃, the feeding temperature to be 50-60 ℃ and the feeding speed to be 5mL/min, so as to obtain water-soluble lutein powder, and packaging by adopting vacuum aluminum foil.
The volume ratio of the lutein absolute ethyl alcohol solution to the aqueous solution containing glucosyl stevioside and hypromellose is 1:100-1:200.
The mass ratio of lutein, glucosyl stevioside and hypromellose in the high water-solubility lutein powder is 1:40:0.5.
The water-soluble lutein powder has good water solubility, and the apparent solubility of lutein reaches more than 2800 mug/mL.
The technical effects are as follows:
1. the glucosyl stevioside is a safe food additive, is obtained by modifying natural stevioside by an enzyme method, and covers the bitter taste of a natural stevioside aglycone mother nucleus structure. Glycosylation is an important step in the structural modification of biologically active compounds, and the aggregated nanostructure of the glycosylated species plays an important role in enhancing the apparent solubility of hydrophobic biologically active species by forming a shell self-associated micelle-like structure having a hydrophobic backbone core and surrounded by sugar groups. Hypromellose is a polymer crystallization inhibitor, and can improve the solubility of active substances, maintain a high-level supersaturation state, and further inhibit the formation of crystallization and precipitation in a liquid environment. By utilizing the respective performance characteristics of the two substances and adopting specific methods and conditions such as an anti-solvent precipitation method, ultra-high pressure micro-jet and the like, a lutein compound system is constructed, so that the apparent solubility of lutein is increased by more than 5000 times, and the stability is good. In the invention, on one hand, the non-covalent combination of hydrogen bond, hydrophobic effect, van der Waals force and the like between glucosyl stevioside and lutein is utilized to form a water-soluble compound, and on the other hand, the hydroxypropyl methylcellulose is used to enable the compound to reach a supersaturated stable state, so that the formation of crystals is inhibited. In addition, the interaction between molecules in the solution is enhanced by utilizing an impinging stream technology through ultrahigh pressure microjet, so that the particle size of the lutein compound is reduced, and the uniform and stable lutein supersaturated solution is obtained.
2. Compared with the prior art, the preparation method mainly utilizes special interaction between compound molecules and coupling with physical and chemical means, uses natural and safe auxiliary materials, and has green and efficient preparation process. The lutein is in a supersaturated state by adopting operations such as ultra-high pressure shearing homogenization treatment, precipitation inhibitors and the like, so that substances such as lutein are prevented from being separated out in a solution, and the stability of water-soluble lutein is enhanced.
3. The existing researches show that the glucosyl stevioside is a natural sweetener, has a certain antioxidant activity, has the functions of reducing blood sugar, preventing decayed teeth, resisting diarrhea, promoting urination, relieving fatigue and the like, and has the auxiliary treatment effect on patients with diabetes, heart disease, hypertension, arteriosclerosis and the like; the glucosyl stevioside covers the original after-bitter taste on the basis of the stevioside, and the glucosyl stevioside is used for enabling the lutein compound system to form a supersaturated system in the water phase, so that the apparent solubility of lutein is promoted. However, since the supersaturated system is in a thermodynamically metastable state, the system is likely to be shifted to a direction in which free energy is reduced, such as precipitation or phase separation. The stability of the supersaturated solution is maintained by the addition of the precipitation inhibitor, hydroxypropyl cellulose. And hydroxypropyl cellulose is a cellulose derivative, an auxiliary material for oral and external preparations, and also often used for foods and cosmetics, and is considered to be a nontoxic, non-irritating substance. The addition of the hydroxypropyl methylcellulose can further improve the apparent solubility of lutein, form stable supersaturated solution and improve the absorption and utilization of lutein in intestinal tracts. Therefore, the water-soluble lutein compound system formed by combining glucosyl stevioside and hypromellose to load lutein plays an important role in improving the bioavailability of lutein.
Drawings
FIG. 1 is a graph showing apparent solubility of water-soluble xanthophylls.
FIG. 2 is an infrared spectrum of water-soluble lutein.
Detailed Description
The invention is further described in connection with the following description, but the scope of the invention as claimed is not limited to the examples described.
Example 1
Taking 50mg of lutein with the purity of 80% to be fully dissolved in 8mL of absolute ethyl alcohol solution, then slowly and uniformly adding the lutein into 800mL of water solution containing hypromellose and 0.05% of ascorbic acid under the magnetic stirring state, and stirring for 20 minutes at the magnetic stirring rotating speed of 400rpm to obtain suspension, wherein the mass ratio of lutein to hypromellose is 1:0.5-1:5. Carrying out dynamic ultrahigh pressure microjet treatment on the obtained suspension for 1 time, wherein the treatment pressure is 104MPa; the micro-jet homogeneous solution is subjected to spray drying treatment, the air inlet temperature is controlled to be 125 ℃, the feeding temperature is controlled to be 50 ℃, and the feeding speed is controlled to be 10mL/min. Obtaining water-soluble lutein powder, and packaging by adopting vacuum aluminum foil.
The obtained binary water-soluble lutein powder has apparent solubility of 0-350 mug/mL by high performance liquid chromatography analysis, wherein the optimal mass ratio of lutein to hypromellose is 1:0.5, and the apparent solubility of lutein is 320.75 mug/mL.
Example 2
50mg of lutein with the purity of 85% is fully dissolved in 8mL of absolute ethanol solution, and then slowly and uniformly added into 800mL of water solution containing glucosyl stevioside and 0.05% of ascorbic acid under the magnetic stirring state. The magnetic stirring speed is 500rpm, the stirring time is 20 minutes, and the suspension is obtained, and the mass ratio of lutein to glucosyl stevioside is 1:1-1:40. Carrying out dynamic ultrahigh pressure microjet circulation treatment on the obtained suspension for 2 times, wherein the treatment pressure is 110MPa; the micro-jet homogeneous solution is subjected to spray drying treatment, the air inlet temperature is controlled to be 130 ℃, the feeding temperature is controlled to be 45 ℃, and the feeding speed is controlled to be 8mL/min. Obtaining water-soluble lutein powder, and packaging by adopting vacuum aluminum foil.
The obtained binary water-soluble lutein powder has apparent solubility of 0-800 mug/mL by high performance liquid chromatography analysis, wherein the optimal mass ratio of lutein to glucosyl stevioside is 1:20, and the apparent solubility of lutein is 683.08 mug/mL.
Example 3
50mg of lutein with the purity of 85% is fully dissolved in 8mL of absolute ethanol solution, and then slowly and uniformly added into 1200mL of aqueous solution containing 0.5g of glucosyl stevioside, different mass of hypromellose and 0.01% of tea polyphenol under the magnetic stirring state. The magnetic stirring speed is 400rpm, the stirring time is 25 minutes, and the suspension is obtained, and the mass ratio of lutein to hypromellose is 1:0.5-1:2. Carrying out dynamic ultrahigh pressure microjet circulation treatment on the obtained suspension for 2 times, wherein the treatment pressure is 124MPa; the micro-jet homogeneous solution is subjected to spray drying treatment, the air inlet temperature is controlled to 140 ℃, the feeding temperature is controlled to 45 ℃, and the feeding speed is controlled to 6mL/min. Obtaining water-soluble lutein powder, and packaging by adopting vacuum aluminum foil.
The apparent solubility of the lutein obtained by high performance liquid chromatography analysis of the ternary water-soluble lutein powder reaches 500-1500 mug/mL, wherein the optimal mass ratio of the lutein to the glucosyl stevioside to the hypromellose is 1:10:0.5, and the apparent solubility of the lutein is 1245.40 mug/mL.
Example 4
50mg of lutein with purity of 90% is fully dissolved in 8mL of absolute ethanol solution, and then slowly and uniformly added into 1600mL of aqueous solution containing 1g of glucosyl stevioside, different mass of hypromellose and 0.01% of tea polyphenol under the magnetic stirring state. The magnetic stirring speed is 550rpm, the stirring time is 25 minutes, and the suspension is obtained, and the mass ratio of lutein to hypromellose is 1:0.5-1:5. Carrying out dynamic ultrahigh pressure micro-jet circulation treatment on the suspension for 2 times, wherein the treatment pressure is 138MPa; the micro-jet homogeneous solution is subjected to spray drying treatment, the air inlet temperature is controlled to be 165 ℃, the feeding temperature is controlled to be 40 ℃, and the feeding speed is controlled to be 6mL/min. Obtaining water-soluble lutein powder, and packaging by adopting vacuum aluminum foil.
The apparent solubility of the lutein obtained by high performance liquid chromatography analysis of the ternary water-soluble lutein powder reaches 1500-2000 mug/mL, wherein the optimal mass ratio of the lutein to the glucosyl stevioside to the hypromellose is 1:20:2, and the apparent solubility of the lutein is 2093.30 mug/mL.
Example 5
50mg of lutein with the purity of 95% is fully dissolved in 8mL of absolute ethanol solution, then slowly and uniformly added to the solution under the magnetic stirring state, and the solution contains 2g of glucosyl stevioside, different mass hydroxypropyl methylcellulose and 0.01% tea polyphenol, and the solution is respectively added into 1600mL of aqueous solution. The magnetic stirring speed is 600rpm, the stirring time is 30 minutes, a suspension is obtained, and the mass ratio of lutein to hypromellose is 1:0.5-1:5. Carrying out dynamic ultrahigh pressure micro-jet circulation treatment on the suspension for 3 times, wherein the treatment pressure is 138MPa; the micro-jet homogeneous solution is subjected to spray drying treatment, the air inlet temperature is controlled to be 165 ℃, the feeding temperature is controlled to be 35 ℃, and the feeding speed is controlled to be 6mL/min. Obtaining water-soluble lutein powder, and packaging by adopting vacuum aluminum foil.
The apparent solubility of lutein obtained by high-water-solubility lutein powder is 1500-3000 mug/mL by high performance liquid chromatography analysis, wherein the optimal mass ratio of lutein to glucosyl stevioside to hypromellose is 1:40:0.5, and the apparent solubility of lutein is 2805.47 mug/mL.
Example 6
Determination of lutein content in water-soluble lutein powder:
high performance liquid chromatography (C) was performed with 5mL of methanol reconstituted water-soluble lutein powder 30 -HPLC) analysis.
C 30 HPLC-DAD analysis conditions: chromatographic column: YMC-C 30 Chromatographic column (4.6 mm. Times.250 mm,5 μm); mobile phase: a is water-MTBE-methanol (5:25:75, V/V/V), B is water-MTBE-methanol (5:85:10, V/V/V); elution gradient setup: 0-4.5 min,95% -80% A;4.5 to 12.5min,80 percent to 50 percent of A; 12.5-15 min,50% -95% A.
Determination of apparent solubility of lutein in water-soluble lutein powder:
drawing a lutein standard curve: 40mg of lutein is taken out into a clean 100mL volumetric flask, dissolved with absolute ethanol and fixed in volume to obtain a lutein stock solution of 400 mug/mL. Respectively precisely weighing standard stock solutions of 0.4, 0.8, 1.2, 1.6, 2.0 and 2.4mL in a volumetric flask of 10mL, diluting to scale with absolute ethanol, shaking uniformly to obtain solutions with mass concentrations of 16, 32, 48, 64, 80 and 96 mug/mL respectively, passing through a 0.45 mu m filter membrane, performing sample injection measurement, and drawing a lutein standard curve by taking the lutein serial standard solution mass concentration as an abscissa and the corresponding absorption peak area as an ordinate to obtain a regression equation: y=0.0093X-0.0082, r 2 ＝0.9996。
The apparent solubility of lutein in the water-soluble lutein powder is calculated as follows:
wherein: lutein content in C-powder, mg/g; y-absorption peak area; l-volume of redissolved solvent, mL; m-sample mass, g.

Claims (5)

1. A high water-solubility lutein powder and a preparation method thereof are characterized in that lutein, glucosyl stevioside and hypromellose molecules are interacted to form a semi-interpenetrating network structure by coupling specific conditions such as anti-solvent precipitation, dynamic ultrahigh-pressure micro-jet, spray drying and the like, so that the high water-solubility lutein powder with amorphous state and improved stability is prepared.
2. The lutein powder with high water solubility and the preparation method thereof are characterized by comprising the following steps:
(1) Fully dissolving high-purity lutein in absolute ethyl alcohol, then slowly and uniformly adding the high-purity lutein into an aqueous solution containing glucosyl stevioside, hypromellose and natural water-soluble antioxidants under a magnetic stirring state, and stirring for 20-30 minutes at a magnetic stirring rotating speed of 400-600 rpm to obtain a suspension;
(2) Carrying out dynamic ultrahigh pressure micro-jet circulation treatment on the suspension obtained in the step (1) for 3 times at a treatment pressure of 100-150 MPa to obtain a micro-jet homogeneous solution;
(3) And (3) carrying out spray drying on the micro-jet homogeneous solution obtained in the step (2), controlling the air inlet temperature to be 180 ℃, the feeding temperature to be 50-60 ℃ and the feeding speed to be 5mL/min, so as to obtain water-soluble lutein powder, and vacuum packaging by adopting aluminum foil.
3. The high water-solubility lutein powder and the preparation method thereof according to claim 2, wherein the volume ratio of the lutein absolute ethyl alcohol solution to the aqueous solution containing glucosyl stevioside and hypromellose in the step (1) is 1:100-1:200.
4. The high water-soluble lutein powder and the preparation method thereof according to claim 1 or 2, wherein the mass ratio of lutein, glucosyl stevioside and hypromellose in the high water-soluble lutein powder is 1:40:0.5.
5. The high water-solubility lutein powder and the preparation method thereof according to claim 1 or 2, wherein the high water-solubility lutein powder has good water solubility, and the apparent solubility of lutein reaches more than 2800 mug/mL.
CN202210011979.7A 2022-01-06 2022-01-06 High-water-solubility lutein powder and preparation method thereof Pending CN116439372A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117964534A (en) * 2024-03-28 2024-05-03 中国农业大学 Amorphous lutein with improved solubility and preparation method thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117964534A (en) * 2024-03-28 2024-05-03 中国农业大学 Amorphous lutein with improved solubility and preparation method thereof

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