A high-content lutein ester microcapsule powder, its preparation method and application

Abstract

This invention provides a high-content lutein ester microcapsule powder, its preparation method, and its application. The raw materials for the high-content lutein ester microcapsule powder include lutein ester crystals, emulsifier a, emulsifier b, a fat-soluble antioxidant, a water-soluble antioxidant, a carrier, and a filler material. Emulsifier a includes emulsifiers with HLB values ​​of 12-15 and 15-18; emulsifier b includes emulsifiers with HLB values ​​of 5-7 and 8-10. The raw materials for the high-content lutein ester microcapsule powder do not contain any other oily components besides lutein ester crystals. The lutein ester microcapsule powder prepared by this invention can achieve a content of 10-25.5%. The preparation process does not involve high-temperature processing, solving the instability problem caused by high-temperature melting of lutein ester during preparation. This effectively avoids the problems of instability during high-temperature sterilization or floating and sedimentation when the lutein ester microcapsule powder is placed for application.

Description

Technical Field

[0001] This invention belongs to the field of microencapsulation powder preparation technology, specifically relating to a high-content lutein ester microencapsulation powder, its preparation method, and its application. Background Technology

[0002] Lutein esters are high-content lutein ester crystals obtained from marigold flowers through processes such as dehydration, pulverization, and solvent extraction. Due to their unique eye-protecting properties, they can prevent UV damage and act as a strong antioxidant to inhibit the activity of reactive oxygen species, thus playing a role in skin and heart health and enhancing immunity. my country's Ministry of Health Announcement No. 12 of 2008 officially approved lutein esters as a functional new resource food.

[0003] Currently, lutein esters are mainly used in functional foods and dietary supplements for eye protection, primarily in tablet and solid beverage forms. However, due to the inherent instability of lutein esters, increasing attention is being paid to their encapsulation. Since the main component of lutein esters is lutein dipalmitate, although it is solid at room temperature, its melting point is relatively low; it softens above 50°C and melts at 60°C. Therefore, traditional encapsulation processes typically involve melting vegetable oil and lutein ester crystals to emulsify the lutein ester, followed by encapsulation with a wall material to obtain microencapsulated lutein ester products. However, this process not only requires carrier vegetable oil, reducing the original lutein ester crystal loading, but also necessitates a high-temperature melting process, leading to high-temperature degradation of the lutein ester, which is detrimental to the development of high-content lutein ester products. Alternatively, solvents can be used to dissolve lutein esters instead of vegetable oil, followed by solvent removal. This addresses the two aforementioned problems, but the introduction of solvents undoubtedly puts pressure on the environment, and solvent residues also pose safety risks during consumption.

[0004] CN112869155A discloses a lutein ester aqueous dispersion formulation, its preparation method, and its application. The method involves mixing 1-8% lutein ester, 10-25% oil phase carrier, and an antioxidant, and then heating the mixture to 65-80℃ to prepare a nano-sized lutein ester aqueous dispersion formulation. This method not only increases the oil phase loading, resulting in low encapsulation rate and product instability, but also increases the risk of degradation of lutein ester due to stirring at high temperatures.

[0005] CN113598304A discloses a method for preparing carotenoids, which involves subjecting the oil phase to ultra-high temperature instantaneous melting (0-300℃) for less than 5 seconds, followed by rapid cooling to below 30℃. While this method partially solves the problem of high-temperature degradation of lutein esters, it still unavoidably uses high temperatures and requires a rapid rise to 300℃ followed by a drop to 30℃. These process conditions are too demanding, placing excessive requirements on equipment that ordinary equipment cannot meet.

[0006] CN111718288A discloses a lutein ester and water-soluble lutein ester microcapsules and their preparation method. The method uses 1 part lutein ester, 1-10 parts vegetable oil, and 0.03-2.0 parts oil phase antioxidant to perform oil phase melting. The melting temperature is 70-135℃. The high preparation temperature increases the risk of degradation of lutein ester.

[0007] CN108578370A discloses a method for preparing lutein / lutein ester granules. This method involves grinding and spraying at 10-35℃ to obtain the granule product. Due to the characteristics of the process, high-content lutein ester granules can be obtained depending on the spraying time. However, this granule product can only be used in tablets and is not suitable for products such as liquid beverages that require coloring.

[0008] In summary, due to the unique properties of lutein ester crystal raw materials, the high-temperature melting or solvent method used in the existing technology for preparing lutein ester powder and microparticles by microencapsulation cannot yield microencapsulated products with high lutein ester content. Furthermore, the high-temperature process not only degrades lutein esters during processing, but also results in poor stability of the microencapsulated products during subsequent storage.

[0009] Effervescent tablets have become a popular dosage form in recent years. They utilize effervescent disintegrants to generate a large amount of carbon dioxide in water, allowing the product to disperse rapidly and providing a sparkling water experience when consumed. While lutein ester microcapsules obtained through conventional methods can also be used in effervescent tablets, they suffer from several issues, including degradation, excessive floating matter after effervescence, the generation of large amounts of acidic and alkaline components during effervescence, lutein ester floating, and low content. Furthermore, in effervescent microcapsules (1mm-3mm in size, tablet weight less than 0.1g), the lutein ester powder content obtained through conventional processes is relatively low, limiting their application.

[0010] Therefore, the preparation of a high-content lutein ester microcapsule powder with a simple and mild preparation method that effectively prevents the degradation of lutein esters and allows for stable storage when applied to beverages or effervescent tablets is a key research focus in this field. Summary of the Invention

[0011] To address the shortcomings of existing technologies, the present invention aims to provide a high-content lutein ester microcapsule powder, its preparation method, and its application. The preparation method is simple and the conditions are mild, effectively preventing the degradation of lutein esters, and it can be stored stably when applied to beverages or effervescent tablets.

[0012] To achieve this objective, the present invention employs the following technical solution:

[0013] In a first aspect, the present invention provides a high-content lutein ester microcapsule powder, wherein the raw materials of the high-content lutein ester microcapsule powder include lutein ester crystals, emulsifier a, emulsifier b, fat-soluble antioxidant, water-soluble antioxidant, carrier and filler material;

[0014] Emulsifier a includes emulsifiers with HLB values ​​of 12-15 and 15-18;

[0015] Emulsifier b includes emulsifiers with HLB values ​​of 5-7 and 8-10;

[0016] The raw materials of the high-content lutein ester microcapsule powder do not contain any oily components other than lutein ester crystals.

[0017] The HLB value is 12-15, for example, it can be 12.5, 13, 13.5, 14, 14.5, etc.

[0018] The HLB value is 15-18, for example, it can be 15.5, 16, 16.5, 17, 17.5, etc.

[0019] The HLB value is 5-7, for example, it can be 5.5, 6, 6.5, etc.

[0020] The HLB value is 8-10, for example, it can be 8.5, 9, 9.5, etc.

[0021] Preferably, by weight, the raw materials of the high-content lutein ester microcapsule powder include 12.5-32 parts of lutein ester crystals (e.g., 13, 15, 17, 19, 21, 23, 25, 27, 29, 31 parts, etc.), emulsifier a (e.g., 1.6, 1.7, 1.8, 1.9 parts, etc.), and emulsifier b. 1.5-2 parts (e.g., 1.6, 1.7, 1.8, 1.9, etc.), 0.001-0.003 parts of fat-soluble antioxidant (e.g., 0.0015, 0.002, 0.0025, etc.), 2-4 parts of water-soluble antioxidant (e.g., 2.5, 3, 3.5, etc.), 35-50 parts of carrier (e.g., 36, 38, 40, 42, 44, 46, 48, etc.), and 15-30 parts of filler material (e.g., 16, 18, 20, 22, 24, 26, 28, etc.).

[0022] Preferably, the mass ratio of emulsifiers with HLB values ​​of 12-15 and 15-18 in emulsifier a is 1:(0.8-1.2), for example, it can be 1:0.9, 1:1, 1:1.1, etc.

[0023] Preferably, the mass ratio of emulsifiers with HLB values ​​of 5-7 and 8-10 in emulsifier b is 1:(0.8-1.2), for example, it can be 1:0.9, 1:1, 1:1.1, etc.

[0024] Preferably, emulsifier a and emulsifier b are each independently selected from any one or a combination of at least two of sucrose fatty acid esters, monoglyceride fatty acid esters, diglyceride fatty acid esters, Tween or sorbitan monoglyceride fatty acid esters.

[0025] Preferably, the fat-soluble antioxidant includes ascorbyl palmitate (VC palmitate).

[0026] Preferably, the water-soluble antioxidant includes sodium ascorbate (sodium VC).

[0027] Preferably, the carrier comprises any one or a combination of at least two of modified starch, gum arabic, octenyl succinate monoarabic ester, gelatin, pectin, or sodium alginate.

[0028] Preferably, the carrier comprises modified starch and / or gum arabic.

[0029] Preferably, the filler material includes any one or a combination of at least two of the following: sucrose, glucose, glucose syrup, isomaltooligosaccharide, fructooligosaccharide, solid corn syrup, xylitol, erythritol, resistant dextrin, or fructooligosaccharide.

[0030] Preferably, the lutein ester content in the high-content lutein ester microcapsule powder is 10-25.5%, for example, it can be 11%, 12%, 13%, 14%, 15%, 16%, 17%, 18%, 19%, 20%, 21%, 22%, 23%, 24%, 25%, etc.

[0031] All other specific point values ​​within the above numerical ranges can be selected, and will not be elaborated on here.

[0032] In a second aspect, the present invention provides a method for preparing high-content lutein ester microcapsule powder as described in the first aspect, the preparation method comprising the following steps:

[0033] (1) Lutein ester crystals, fat-soluble antioxidants, emulsifier a and carrier are subjected to a first co-emulsification treatment to obtain a first co-emulsified product;

[0034] (2) The first coemulsifier obtained in step (1), the filler material, the water-soluble antioxidant, the emulsifier b and water are subjected to a second coemulsification treatment to obtain the second coemulsifier, and dried to obtain the high-content lutein ester microcapsule powder;

[0035] Preferably, the temperature of the first co-emulsification treatment is -25 to -20°C (e.g., -24°C, -23°C, -22°C, -21°C, etc.), the vacuum degree is 0.008-0.012 MPa (e.g., 0.009 MPa, 0.01 MPa, 0.011 MPa, etc.), and the emulsification time is 15-30 min, e.g., 16 min, 18 min, 20 min, 22 min, 24 min, 26 min, 28 min, etc.

[0036] Preferably, the particle size of the first co-emulsion is 10-30 μm, for example, it can be 12 μm, 15 μm, 20 μm, 25 μm, 28 μm, etc.

[0037] Preferably, the temperature of the second co-emulsification treatment is 5-15℃ (e.g., 6℃, 8℃, ...).

[0038] Temperatures can be set at 10℃, 12℃, 14℃, etc., with a vacuum degree of 0.035-0.045MPa (e.g., 0.038MPa, 0.04MPa, 0.042MPa, etc.) and an emulsification time of 15-30min (e.g., 16min, 18min, 20min, 22min, 24min, 26min, 28min, etc.).

[0039] Preferably, the particle size of the second co-emulsion is <1 μm, for example, it can be 0.9 μm, 0.8 μm, 0.7 μm, 0.6 μm, 0.5 μm, 0.4 μm, 0.3 μm, 0.2 μm, 0.1 μm, 0.05 μm, etc.

[0040] Preferably, the lutein ester crystals are prepared by the following method: marigold extract is mixed with 3-5 times (e.g., 3.5 times, 4 times, 4.5 times, etc.) of 70-95% (e.g., 75%, 80%, 85%, 90%, etc.) aqueous ethanol solution, stirred at 40-50℃ (e.g., 42℃, 44℃, 46℃, 48℃, etc.) for at least 20 minutes, then dispersed by high-speed shearing, and vacuum dried at 30-50℃ (e.g., 35℃, 40℃, 45℃, etc.) to obtain lutein ester crystals.

[0041] Preferably, the total pigment content in the lutein ester crystals is >80% (e.g., 82%, 84%, 86%, 88%, 90%, etc.), the content of trans-lutein liquid phase composition is >90% (e.g., 91%, 92%, 93%, 94%, 95%, etc.), and the water content is <5% (e.g., 4.5%, 4%, 3.5%, 3%, 2.5%, etc.).

[0042] Preferably, the first co-emulsification treatment and the second co-emulsification treatment each independently include any one of crushing, shearing or grinding.

[0043] In this invention, both the first and second co-emulsification processes are carried out under vacuum, which can effectively control the residual gas in the system and reduce the amount of foam.

[0044] In the first co-emulsification process, the addition of emulsifier a (hydrophilic emulsifier) ​​can effectively change the interfacial tension of the first co-emulsifier, making it easier to blend with water and facilitating subsequent emulsification. In the second co-emulsification process, the addition of emulsifier b (lipophilic emulsifier) ​​can effectively reduce the surface tension of water, thereby increasing the time-dependent attraction between water-soluble and lipid-soluble molecules and achieving interfacial equilibrium.

[0045] Preferably, the preparation method includes the following steps:

[0046] (1) Lutein ester crystals, fat-soluble antioxidants, emulsifier a and carrier are mixed and subjected to a first co-emulsification treatment for 15-30 min at -25 to -20℃ and a vacuum degree of 0.008-0.012 MPa to obtain a first co-emulsifier with a particle size of 10-30 μm.

[0047] (2) The first coemulsifier obtained in step (1), the filler material, the water-soluble antioxidant, the emulsifier b and water are mixed and subjected to a second coemulsification treatment at 5-15℃ and vacuum degree 0.035-0.045MPa for 15-30min to obtain a second coemulsifier with a particle size <1μm. The second coemulsifier is dried to obtain the high-content lutein ester microcapsule powder.

[0048] All other specific point values ​​within the above numerical ranges can be selected, and will not be elaborated on here.

[0049] Thirdly, the present invention provides an application of high-content lutein ester microcapsule powder as described in the first aspect in beverages or effervescent tablets.

[0050] Fourthly, the present invention provides a sugar-free lutein ester beverage, wherein the sugar-free lutein ester beverage comprises, by weight, 0.1-0.5 parts (e.g., 0.2 parts, 0.3 parts, 0.4 parts, etc.) of the high-content lutein ester microcapsule powder provided in the first aspect, 5-30 parts (e.g., 15 parts, 20 parts, 25 parts, etc.) of xylitol, 1-5 parts (e.g., 2 parts, 3 parts, 4 parts, etc.) of apple juice, 0.01-0.05 parts (e.g., 0.02 parts, 0.03 parts, 0.04 parts, etc.) of apple flavoring, 0.1-3 parts (e.g., 0.2 parts, 0.5 parts, 1 part, 2 parts, 3 parts, etc.) of citric acid, and 10-100 parts (e.g., 15 parts, 30 parts, 50 parts, 80 parts, etc.) of water.

[0051] Preferably, the sugar-free lutein ester beverage is prepared by the following method:

[0052] The high-content lutein ester microcapsule powder, xylitol, apple juice, apple flavoring, citric acid and water are mixed and then passed through a 200-mesh sieve to remove insoluble matter. The mixture is heated to 90°C and kept warm for 30 minutes. It is then bottled while hot to obtain the sugar-free lutein ester beverage.

[0053] All other specific point values ​​within the above numerical ranges can be selected, and will not be elaborated on here.

[0054] Fifthly, the present invention provides a lutein ester effervescent microtablet, wherein the lutein ester effervescent microtablet comprises, by weight, 20-40 parts (e.g., 25 parts, 30 parts, 35 parts, etc.) of the high-content lutein ester microcapsule powder provided in the first aspect, 15-25 parts (e.g., 16 parts, 18 parts, 20 parts, 22 parts, 24 parts, etc.), 10-20 parts (e.g., 12 parts, 14 parts, 16 parts, 18 parts, etc.) of sodium bicarbonate, 2-8 parts (e.g., 4 parts, 5 parts, 6 parts, etc.) of mannitol, 20-30 parts (e.g., 22 parts, 24 parts, 26 parts, 28 parts, etc.) of lactose, 1-3 parts (e.g., 1.5 parts, 2 parts, 2.5 parts, etc.) of flavoring agent, and 2-4 parts (e.g., 2.5 parts, 3 parts, 3.5 parts, etc.) of leucine.

[0055] Preferably, the flavoring agent includes any one or a combination of at least two of sucralose, steviol glycosides, or other edible flavorings.

[0056] All other specific point values ​​within the above numerical ranges can be selected, and will not be elaborated on here.

[0057] Compared with the prior art, the present invention has the following beneficial effects:

[0058] 1. In the process of preparing lutein ester microcapsule powder, the present invention does not use oil as a carrier, so that the content of lutein ester in the microcapsule powder can reach 10-25.5%;

[0059] 2. The present invention does not involve high-temperature processing, which solves the instability problem caused by high-temperature melting of lutein esters during preparation and effectively avoids the problems of instability during high-temperature sterilization or floating and sedimentation when lutein ester microcapsule powder is placed during application.

[0060] 3. The preparation method of lutein ester microcapsule powder provided by the present invention does not use organic solvents, and the process is environmentally friendly and safe.

[0061] 4. The lutein ester microcapsule powder provided by this invention has a wide range of applications and can be used in liquid beverages, oral liquids, effervescent tablets and other fields. Detailed Implementation

[0062] The technical solution of the present invention will be further illustrated below through specific embodiments. Those skilled in the art should understand that the embodiments described are merely illustrative of the present invention and should not be construed as limiting the invention in any way.

[0063] The terms “comprising,” “including,” “having,” “containing,” or any other variations thereof, as used herein, are intended to cover non-exclusive inclusion. For example, a composition, step, method, article, or apparatus that includes the listed elements is not limited to those elements and may also include other elements not expressly listed or elements inherent to such composition, step, method, article, or apparatus.

[0064] "Optional" or "any one" means that the matter or event described thereafter may or may not occur, and the description includes both the possibility that the event will occur and the possibility that the event will not occur.

[0065] The indefinite articles “a” and “an” preceding an element or component of this invention do not impose any limitation on the quantity (i.e., number of times) of the element or component. Therefore, “an” or “a” should be interpreted as including one or at least one, and the singular form of an element or component also includes the plural form, unless the quantity clearly refers only to the singular form.

[0066] The terms "one embodiment," "some embodiments," "exemplary," "specific example," or "some examples," etc., used in this invention refer to specific features, structures, materials, or characteristics described in connection with that embodiment or example, which are included in at least one embodiment or example of the invention. In this document, the illustrative expressions of the above terms are not necessarily directed at the same embodiment or example.

[0067] The reagents or instruments used in the following examples are from the following sources:

[0068] The raw materials used in the embodiments, comparative examples, or application examples of this invention are all conventional commercially available products;

[0069] It should be noted that, in the following examples and comparative examples, the lipid-soluble antioxidants used in the raw materials for preparing lutein ester microcapsule powder are measured by content (unit: ppm) due to their small amount, while other raw materials are measured by weight.

[0070] Preparation Example 1

[0071] This preparation example provides a lutein ester crystal, and the preparation method of the lutein ester crystal is as follows:

[0072] Marigold extract was mixed with 4 times the amount of 85% ethanol aqueous solution, stirred at 45°C for 25 minutes, then dispersed by high-speed shearing, and dried under vacuum at 40°C to obtain lutein ester crystals.

[0073] The lutein ester crystals were found to contain 86% total pigment, 93% trans-lutein liquid phase composition, and 3% water.

[0074] Example 1

[0075] This embodiment provides a high-content lutein ester microcapsule powder, the raw materials of which include:

[0076] Preparation Example 1: 20 parts of lutein ester crystals, 2 parts of emulsifier a, 2 parts of emulsifier b, 20 ppm of VC palmitate, 3 parts of VC sodium, 48 parts of modified starch, and 25 parts of xylitol;

[0077] Emulsifier A includes: 1 part of Tween with an HLB value of 12-15 and 1 part of Tween with an HLB value of 15-18;

[0078] Emulsifier b includes: 1 part Tween with an HLB value of 5-7 and 1 part Tween with an HLB value of 8-10;

[0079] The preparation method of the high-content lutein ester microcapsule powder is as follows:

[0080] (1) Lutein ester crystals, VC palmitate, emulsifier a and modified starch were mixed and sheared and emulsified at -23℃ and vacuum degree 0.01MPa for 20 min to obtain the first co-emulsion;

[0081] (2) The first coemulsifier obtained in step (1), xylitol, sodium VC, emulsifier b and 150 parts of water are mixed and sheared and emulsified at 10°C and vacuum degree 0.04MPa for 20 min to obtain the second coemulsifier. The second coemulsifier is spray-dried to obtain the high content lutein ester microcapsule powder.

[0082] Example 2

[0083] This embodiment provides a high-content lutein ester microcapsule powder, the raw materials of which include:

[0084] Preparation Example 1: 12.5 parts of lutein ester crystals, 1.6 parts of emulsifier a, 2 parts of emulsifier b, 10 ppm of VC palmitate, 4 parts of sodium VC, 49.5 parts of gum arabic, and 30 parts of glucose;

[0085] Emulsifier A includes: 0.8 parts of sucrose fatty acid ester with HLB value of 12-15 and 0.8 parts of sucrose fatty acid ester with HLB value of 15-18;

[0086] Emulsifier b includes: 1 part of sucrose fatty acid ester with HLB value of 5-7 and 1 part of sucrose fatty acid ester with HLB value of 8-10.

[0087] The preparation method of the high-content lutein ester microcapsule powder is as follows:

[0088] (1) Lutein ester crystals, VC palmitate, emulsifier a and gum arabic were mixed and sheared and emulsified at -20℃ and vacuum degree 0.01MPa for 30 min to obtain the first co-emulsion;

[0089] (2) The first coemulsifier obtained in step (1), glucose, sodium VC, emulsifier b and 150 parts of water are mixed and sheared and emulsified at 15°C and vacuum degree 0.04MPa for 15 min to obtain the second coemulsifier. The second coemulsifier is spray-dried to obtain the high content lutein ester microcapsule powder.

[0090] Example 3

[0091] This embodiment provides a high-content lutein ester microcapsule powder, the raw materials of which include:

[0092] Preparation Example 1: 32 parts of lutein ester crystals, 2 parts of emulsifier a, 1.6 parts of emulsifier b, 30 ppm of VC palmitate, 2 parts of sodium VC, 42.4 parts of modified starch, and 20 parts of isomaltooligosaccharide;

[0093] Emulsifier A includes: 1 part of Tween with an HLB value of 12-15 and 1 part of Tween with an HLB value of 15-18;

[0094] Emulsifier b includes: 0.8 parts of Tween with an HLB value of 5-7 and 0.8 parts of Tween with an HLB value of 8-10;

[0095] The preparation method of the high-content lutein ester microcapsule powder is as follows:

[0096] (1) Lutein ester crystals, VC palmitate, emulsifier a and modified starch were mixed and sheared and emulsified at -25℃ and vacuum degree 0.01MPa for 15min to obtain the first co-emulsion;

[0097] (2) The first coemulsifier obtained in step (1), isomaltooligosaccharide, sodium VC, emulsifier b and 150 parts of water are mixed and sheared and emulsified at 5°C and vacuum degree 0.04MPa for 30 min to obtain the second coemulsifier. The second coemulsifier is spray-dried to obtain the high content lutein ester microcapsule powder.

[0098] Example 4

[0099] This embodiment provides a high-content lutein ester microcapsule powder, which differs from Example 1 only in the emulsifier a. In this embodiment, emulsifier a includes: 1.2 parts of Tween with an HLB value of 12-15 and 0.8 parts of Tween with an HLB value of 15-18; other raw materials, dosages and preparation methods are the same as in Example 1.

[0100] Example 5

[0101] This embodiment provides a high-content lutein ester microcapsule powder, which differs from Example 1 only in the emulsifier a. In this embodiment, emulsifier a includes: 0.8 parts of Tween with an HLB value of 12-15 and 1.2 parts of Tween with an HLB value of 15-18; other raw materials, dosages and preparation methods are the same as in Example 1.

[0102] Example 6

[0103] This embodiment provides a high-content lutein ester microcapsule powder, which differs from Example 1 only in the emulsifier b. In this embodiment, emulsifier b includes: 1.2 parts of Tween with an HLB value of 5-7 and 0.8 parts of Tween with an HLB value of 8-10; other raw materials, dosages and preparation methods are the same as in Example 1.

[0104] Example 7

[0105] This embodiment provides a high-content lutein ester microcapsule powder, which differs from Example 1 only in the emulsifier b. In this embodiment, emulsifier b includes: 0.8 parts of Tween with an HLB value of 5-7 and 1.2 parts of Tween with an HLB value of 8-10; other raw materials, dosages and preparation methods are the same as in Example 1.

[0106] Example 8

[0107] This embodiment provides a high-content lutein ester microcapsule powder, which differs from Example 1 only in that VC palmitate is replaced with an equal amount of VE (vitamin E); other raw materials, dosages and preparation methods are the same as in Example 1.

[0108] Example 9

[0109] This embodiment provides a high-content lutein ester microcapsule powder, which differs from Example 1 only in that sodium VC is replaced with an equal amount of VC (vitamin C); other raw materials, dosages and preparation methods are the same as in Example 1.

[0110] Comparative Example 1

[0111] This comparative example provides a high-content lutein ester microcapsule powder, which differs from Example 1 only in that Tween with an HLB value of 15-18 is not added to emulsifier a, the total amount of emulsifier a remains unchanged, and the insufficient part is made up by Tween with an HLB value of 12-15. Other raw materials, dosages and preparation methods are the same as in Example 1.

[0112] Comparative Example 2

[0113] This comparative example provides a high-content lutein ester microcapsule powder, which differs from Example 1 only in that Tween with an HLB value of 12-15 is not added to emulsifier a, the total amount of emulsifier a remains unchanged, and the insufficient part is made up by Tween with an HLB value of 15-18. Other raw materials, dosages and preparation methods are the same as in Example 1.

[0114] Comparative Example 3

[0115] This comparative example provides a high-content lutein ester microcapsule powder, which differs from Example 1 only in that Tween with an HLB value of 8-10 is not added to emulsifier b, the total amount of emulsifier b remains unchanged, and the insufficient part is made up by Tween with an HLB value of 5-7. Other raw materials, dosages and preparation methods are the same as in Example 1.

[0116] Comparative Example 4

[0117] This comparative example provides a high-content lutein ester microcapsule powder, which differs from Example 1 only in that Tween with an HLB value of 5-7 is not added to emulsifier b, the total amount of emulsifier b remains unchanged, and the insufficient part is made up by Tween with an HLB value of 8-10. Other raw materials, dosages and preparation methods are the same as in Example 1.

[0118] Comparative Example 5

[0119] This comparative example provides a lutein ester microcapsule powder, which differs from Example 1 only in its preparation method. The preparation method of this comparative example is as follows:

[0120] (1) Lutein ester crystals, VC palmitate, emulsifier a, modified starch, xylitol, sodium VC, emulsifier b and 150 parts of water are mixed evenly and subjected to shear emulsification treatment at 10°C and vacuum degree 0.04MPa for 20 min to obtain a co-emulsion. The co-emulsion is spray-dried to obtain the lutein ester microcapsule powder.

[0121] Comparative Example 6

[0122] This comparative example provides a lutein ester microcapsule powder, which differs from Example 1 only in its preparation method. The preparation method of this comparative example is as follows:

[0123] Refer to the method in Example 1 of CN112869155A:

[0124] Ingredients: 25g lutein ester crystals, 112.5g molecularly distilled monoglyceride, 150g sodium octenyl succinate starch, 115g maltodextrin, 60g sucrose, 12.5g L-ascorbic acid, and 25g vitamin E.

[0125] Preparation method:

[0126] (1) Dissolve the above weight of sodium octenyl succinate starch, maltodextrin, sucrose and L-ascorbic acid in pure water at 70°C to obtain an aqueous phase;

[0127] (2) Lutein ester was melted in molecularly distilled monoglyceride containing vitamin E at 70℃ to obtain the oil phase;

[0128] (3) Under high shear emulsification conditions of 7000 r / min, the oil phase was added to the aqueous phase. After the addition was complete, emulsification was continued for 10 min to obtain the primary emulsion.

[0129] (4) First, grind the primary emulsion to a particle size of 0.25μm using zirconia balls with a particle size of 0.4-0.6mm, then replace with zirconia balls with a particle size of 0.2-0.4mm to continue grinding the emulsion until the particle size of the emulsion is 0.08μm.

[0130] (5) Spray dry the ground emulsion to obtain the final product.

[0131] Test Example 1

[0132] The product sterilization evaluation method adopted in this invention at 90℃ is as follows: Lutein ester microcapsule powder prepared in the examples and comparative examples was weighed according to a concentration of 12 mg lutein ester / 100 mL water, and a liquid solution was prepared. The pH was then adjusted to 3.5 using sodium citrate and sodium carbonate. The adjusted solution was heated to 90℃ and held at that temperature for 30 min. The lutein ester content was measured to determine its retention rate during sterilization. The results of the 90℃ sterilization retention rate determination are shown in Table 1.

[0133] Test Example 2

[0134] The particle size of the product of this invention was measured by a laser particle size analyzer, and the D90 value was recorded in μm. The measurement results are shown in Table 1.

[0135] Test Example 3

[0136] Referring to the Chinese Pharmacopoeia's accelerated stability evaluation method, under conditions of 40℃ and 75% RH, the pigment content at different times was measured to determine its stability, and the pigment retention rate was used to represent product stability. The pigment retention rate is the ratio of the product content at different times to the initial content, expressed as a percentage. "Trace oil droplets" indicates that the surface oil droplet area is ≤5%; "Oil droplets +" indicates that the surface oil droplet area is 10-25%; "Oil droplets +" indicates that the surface oil droplet area is 25-40%; "Oil droplets +++" indicates that the surface oil droplet area is 40-60%; "Oil droplets" indicates that oil droplets or oil layers are obvious. The results are shown in Table 1.

[0137] Table 1

[0138]

[0139] According to the table data, when using emulsifier a and emulsifier b provided by this invention, the lutein ester content in the microcapsule powder is the highest, and the stability of the microcapsule powder is the best. When the proportion of emulsifier a with an HLB value of 12-15 is too high or too low, the emulsification effect is poor, and it does not play a bridging role. When the proportion of emulsifier b with an HLB value of 5-7 is too high, there is too much lipophilic emulsifier, which affects the water-oil balance. When the proportion is too low, it is insufficient to provide emulsifier with a low HLB value, and the oil phase emulsification effect deteriorates. When VE is used as a fat-soluble antioxidant, the antioxidant capacity of the oil phase weakens, the product stability deteriorates, and VE does not... Facilitating emulsification leads to an increase in particle size and a decrease in stability. When VC is used as a water-soluble antioxidant, the pH of the aqueous phase changes, preventing it from forming a buffer ion pair with citric acid during 90°C sterilization, unlike sodium VC, thus negatively impacting stability. When emulsifier a is a single emulsifier with an HLB value of 15-18 or 12-15, a good emulsion system is not formed, resulting in insufficient hydrophilicity of the first co-emulsion. When emulsifier b is a single emulsifier with an HLB value of 8-10 or 5-7, the affinity for the oil phase is insufficient or the connection with the aqueous phase emulsifier is inadequate.

[0140] In addition, Comparative Example 6 prepared lutein ester microcapsule powder according to CN112869155A. The theoretical content of the obtained microcapsule powder was 5.0%, while the actual measured content was 4.1%, indicating that there was processing loss of lutein ester during the high-temperature preparation process. The loss rate was 18%, that is, 18% of the lutein ester was lost due to high temperature during the high-temperature processing.

[0141] Test Example 4

[0142] Determination of total carotenoid (UV) content

[0143] Weigh an appropriate amount (0.02 g - 0.20 g) of lutein ester microcapsule powder prepared in the examples and comparative examples, accurate to 0.1 mg, and place it in a 100 mL brown volumetric flask. Add 10 mL of water and sonicate for 2 min. Add 40 mL of tetrahydrofuran, mix well, and extract by sonication for 2 min. After returning to room temperature, dilute to volume with anhydrous ethanol and shake well. Obtain 1 mL of the supernatant solution by centrifugation or filtration membrane and place it in a 25 mL brown volumetric flask. Dilute to volume with anhydrous ethanol and shake well. Place the sample in a 1 cm cuvette, using anhydrous ethanol as a blank control, and measure the absorbance at the maximum absorption wavelength of 445 nm using a visible spectrophotometer. (The absorbance should be controlled between 0.3 and 0.7; otherwise, adjust the sample solution concentration and remeasure the absorbance.)

[0144] The calculation formula is: W0=(A-A0)×d / (m×1394);

[0145] W0—Total carotenoid ester content, expressed in grams per 100 grams (g / 100g);

[0146] A—The absorbance of the actual sample solution being measured;

[0147] A0—Absorbance of the blank sample;

[0148] d—Dilution factor of the tested sample;

[0149] m—Sample mass, in grams (g);

[0150] 1394—Absorption coefficient of the sample solution at a wavelength of 445 nm. The measurement results are shown in Table 2.

[0151] Test Example 5

[0152] Determination of pigment composition and content by high-performance liquid chromatography (HPLC)

[0153] Weigh the lutein ester microcapsule powder prepared in the examples and comparative examples into a 50 mL centrifuge tube, add 10 mL of water to form an emulsion (if emulsion formation is difficult, add 0.1 g of trypsin and incubate at 40 °C for about 10 min), then add 3 g of sodium chloride, vortex for 2 min, then add 10 mL of anhydrous ethanol and mix well, then add 20 mL of petroleum ether, seal, shake vigorously for 1 min, centrifuge at 3000 rpm for 5 min, and transfer the petroleum ether layer to a rotary evaporator flask and evaporate to dryness under reduced pressure at 60 °C. Take the evaporated sample, add 30 mL of isopropanol and 2 mL of 0.4 g / mL potassium hydroxide-methanol solution, and saponify in a 55 °C water bath in the dark for 30 min. After reaction, remove and immediately cool to room temperature. Transfer 1 mL of the saponification reaction solution to a 25 mL centrifuge tube. Add 0.5 mL of tetrahydrofuran and 1.5 mL of n-hexane. Vortex for 1 min. Add 10 mL of aqueous solution and gently shake for 10 s. Centrifuge at 3000 rpm for 5 min. Note that no pigment should precipitate from the aqueous layer at this point; otherwise, the extraction process must be repeated. Immediately collect the supernatant and add 0.5 g of anhydrous sodium sulfate to remove water before use. Reference liquid chromatography pigment conditions are as follows:

[0154] a) Chromatographic column: silica gel column, 4.6 mm × 250 mm, particle size 5 μm;

[0155] b) Mobile phase: n-hexane:ethyl acetate = 70:30 (V / V);

[0156] c) Column temperature: 40℃;

[0157] d) Flow rate: 1.5 mL / min;

[0158] e) Ultraviolet detection wavelength: 445nm;

[0159] f) Injection volume: 20 μL.

[0160] Lutein ester content, expressed as a mass fraction, is calculated in grams per 100 grams (g / 100g) using the formula: w1=W0×A1;

[0161] W0—Total carotenoid ester content, expressed in grams per 100 grams (g / 100g);

[0162] w1—Content of lutein esters (calculated as lutein dipalmitate), in grams per 100 grams (g / 100g);

[0163] A1—Percentage of lutein peak area in the chromatogram.

[0164] The product content (%) was tested using the method in Test Example 3: 40℃, 75% RH humidity, after 3 months; and the product content (%) was tested using the method in Test Example 1: sterilized at 90℃ for 30 minutes. The results are shown in Table 2.

[0165] Table 2

[0166]

[0167]

[0168] According to the data in the table, the lutein ester prepared using the technical solution of this invention exhibits good stability during both the product acceleration process and the beverage sterilization process. In Examples 1-3, the product retention rate after 3 months of acceleration at 40°C and 75% RH humidity was over 98%, while the retention rate after high-temperature acid sterilization was also over 96%. However, Examples 8 and 9, which involved changing the antioxidant, affected product stability, with the product retention rate after acceleration at 90-92% and the retention rate after high-temperature acid sterilization at 75%-80%. Data from Comparative Examples 1-5 show that changes in emulsifiers or process flow significantly reduced product stability, with the product retention rate after acceleration at 92%-93% and the retention rate after high-temperature acid sterilization at 80%-83%. High temperatures are not suitable for the preparation of lutein esters. The content of the product can remain unchanged during the processing. However, in Comparative Example 6, the lutein ester product was prepared by simulating high temperature treatment. The theoretical content was 5%, and the actual content was 4.1%, indicating that the content was degraded by 18% during the processing. In the subsequent stability test, the content retention rate was only 64.3% and 55.27%, which is far lower than the level of this patent.

[0169] Test Example 6

[0170] Blue light damage resistance test - animal experiment

[0171] Laboratory animals:

[0172] Kunming mice (KM), male, with an average weight of 33g, were purchased from Liaoning Changsheng Biotechnology Co., Ltd. They were housed for 4-6 weeks, with 12 hours of lighting daily and an ample supply of water and food. All animal experiments were conducted in accordance with the approval of the Animal Care and Use Committee of Dalian Medical University (ethics number: AEE21112).

[0173] Drugs and reagents:

[0174] Malondialdehyde (MDA) kit, total superoxide dismutase (T-SOD) kit, and glutathione peroxidase (GSH-PX) kit were all purchased from Nanjing Jiancheng Bioengineering Institute.

[0175] Experimental methods:

[0176] Establishment of a mouse model of blue light damage and administration of a high-anti-blue light composition: According to the experimental grouping design, mice were divided into groups:

[0177] Control group: Normal saline was administered for 14 consecutive days, and after the administration was completed, the dark conditions were maintained for 12 hours.

[0178] Blue light group: The patient was given saline solution for 14 consecutive days. After the administration was completed, the patient was irradiated with blue light with an average illuminance of 4000-5333 Lux for 12 hours.

[0179] Experimental group: Each mouse was given 20 mg / kg of the test substance (equivalent to 20 mg / kg of lutein ester) daily for 14 consecutive days. After the administration was completed, the mice were exposed to blue light with an average illuminance of 4000-5333 Lux for 12 hours. The test substance was: lutein ester crystals, Example 1;

[0180] After the blue light irradiation ended, the mice used in the experiment were euthanized, and serum (without hemolysis) and retinal tissue (with nerves and blood vessels removed) were collected. The levels of MDA, T-SOD, and GSH-PX in the serum were measured according to the instructions of the MDA, T-SOD, and GSH-PX kits, respectively.

[0181] Results Analysis: Based on the results of the blank group, the content of all indicators in each group was calculated. Results analysis compared each experimental group with the blue light group, presenting the results as the fold increase / decrease in content.

[0182] The calculation formula is:

[0183] T-SOD growth factor = (experimental group / blue light group - 1);

[0184] GSH-PX growth factor = (experimental group / blue light group - 1);

[0185] MDA reduction factor = Blue light group / Experimental group - 1. The test results are shown in Table 3.

[0186] Table 3

[0187] sample MDA decrease factor T-SOD growth factor GSH-PX growth multiple Lutein ester crystals 0.13 2.35 1.56 Example 1 0.44 4.20 1.85

[0188] Animal experiments have shown that the lutein ester microcapsule powder prepared in this patent has a better protective effect against oxidative damage caused by blue light. The MDA reduction factor is three times that of lutein ester crystals.

[0189] Application Example 1

[0190] This application example provides a sugar-free beverage, the preparation method of which is as follows:

[0191] 0.2 parts of lutein ester microcapsule powder, 28 parts of xylitol, 5 parts of apple juice, 0.01 parts of apple flavoring and 1 part of citric acid prepared in Example 1 were dissolved in 100 parts of water. The fully dissolved solution was passed through a 200-mesh sieve to remove insoluble matter, heated to 90°C, kept warm for 30 minutes, and filled while hot to obtain the sugar-free beverage.

[0192] Application Example 2-3

[0193] This application example provides a sugar-free beverage, which differs from Application Example 1 only in that the lutein ester microcapsule powder prepared in Example 1 is replaced with an equal amount of lutein ester microcapsule powder prepared in Examples 8-9. All other raw materials, amounts, and preparation methods are the same as in Application Example 1.

[0194] Comparative Application Examples 1-6

[0195] This application example provides a sugar-free beverage, the preparation method of which is as follows:

[0196] The only difference between this example and Application Example 1 is that the lutein ester microcapsule powder prepared in Example 1 is replaced with an equal amount of lutein ester microcapsule powder prepared in Comparative Examples 1-6. All other raw materials, amounts, and preparation methods are the same as in Application Example 1.

[0197] Test Example 7

[0198] Accelerated testing was conducted for 3 months at 37℃±2℃ and relative humidity of 60%±5% to examine the stability of the sugar-free beverage and to detect the retention rate of lutein esters in the sugar-free beverage. The test results are shown in Table 4.

[0199] Table 4

[0200] sample Content retention rate (%) Product Status Application Example 1 90 Homogeneous liquid, without floating or sedimentation Application Example 2 75 Trace amount of oil Application Example 3 77 Trace amounts of oil droplets and trace amounts of sediment accumulation. Comparative Application Example 1 73 Significant rise Comparative Application Example 2 75 Significant rise Comparative Application Example 3 72 Trace amount floats, precipitates Comparative Application Example 4 77 Trace amount floats, precipitates Comparative Application Example 5 68 Trace amount floats, precipitates Comparative Application Example 6 35 It rises noticeably and has an oil ring.

[0201] According to the table data, when emulsifier a is a single emulsifier with an HLB value of 15-18 or 12-15, significant floating occurs after application to ready-to-drink beverages. When emulsifier a is a single emulsifier with an HLB value of 8-10 or 5-7, slight floating and bottom sedimentation occur. For products prepared using a one-step method, the beverage stability is poor, and floating and sedimentation occur. In comparative application example 6, which uses vegetable oil as a carrier, obvious oil rings appear during acceleration, and stability is poor.

[0202] Application Example 4

[0203] This application example provides a lutein ester effervescent microtablet, the preparation method of which is as follows:

[0204] 30 parts of the lutein ester microcapsule powder prepared in Example 3, 20 parts of citric acid, 16 parts of sodium bicarbonate, 5 parts of mannitol, 24 parts of lactose, 2 parts of sucralose, and 3 parts of leucine were tableted using a rotary tableting machine to obtain the lutein ester effervescent microtablets. The tablet weight was 0.05 g, and the tablet hardness was 40 N.

[0205] Comparative Application Example 7

[0206] This comparative application example provides a lutein ester effervescent microtablet, the preparation method of which is as follows:

[0207] The only difference between this example and Application Example 4 is that the lutein ester microcapsule powder prepared in Example 3 is replaced with an equal amount of the lutein ester microcapsule powder prepared in Comparative Example 6. All other raw materials, amounts, and preparation methods are the same as in Application Example 4.

[0208] Test Example 8

[0209] Accelerated testing was conducted for 3 months at 40℃±2℃ and relative humidity of 75%±5% to investigate the stability of lutein ester effervescent tablets and to detect the retention rate of lutein ester content in the effervescent tablets. The test results are shown in Table 5.

[0210] Table 5

[0211]

[0212] According to the recommendations for new resource foods, the dosage of lutein esters should not exceed 12mg / day. The lutein ester microbubble tablets provided by this invention can achieve the required dosage of 11mg / day by taking 3 tablets a day. They are convenient to take and have stable content. However, the lutein ester microbubble tablets prepared using Comparative Example 6 have a content of only 0.61mg, requiring nearly 20 tablets a day to meet the requirement, which greatly increases the difficulty of taking them.

[0213] The applicant declares that the present invention is illustrated by the above embodiments, but the present invention is not limited to the above embodiments, that is, it does not mean that the present invention must rely on the above embodiments to be implemented. Those skilled in the art should understand that any improvements to the present invention, equivalent substitutions of raw materials for the product of the present invention, addition of auxiliary components, selection of specific methods, etc., all fall within the protection scope and disclosure scope of the present invention.

Claims

1. A high-content lutein ester microcapsule powder, characterized in that, The raw materials of the high-content lutein ester microcapsule powder include lutein ester crystals, emulsifier a, emulsifier b, fat-soluble antioxidant, water-soluble antioxidant, carrier, and filler material. Emulsifier a comprises emulsifiers with HLB values ​​of 12-15 and 15-18; the mass ratio of emulsifiers with HLB values ​​of 12-15 and 15-18 in emulsifier a is 1:(0.8-1.2); emulsifier a is a hydrophilic emulsifier; Emulsifier b comprises emulsifiers with HLB values ​​of 5-7 and 8-10; the mass ratio of emulsifiers with HLB values ​​of 5-7 and 8-10 in emulsifier b is 1:(0.8-1.2); emulsifier b is a lipophilic emulsifier; The raw materials of the high-content lutein ester microcapsule powder do not contain any oily components other than lutein ester crystals. The high-content lutein ester microcapsule powder is prepared by the following method, which includes the following steps: (1) Lutein ester crystals, fat-soluble antioxidants, emulsifier a and carrier are subjected to a first co-emulsification treatment to obtain a first co-emulsified product; the temperature of the first co-emulsification treatment is -25~-20℃, the vacuum degree is 0.008-0.012 MPa, and the emulsification time is 15-30 min; (2) The first coemulsifier obtained in step (1), the filler material, the water-soluble antioxidant, the emulsifier b and water are subjected to a second coemulsification treatment to obtain a second coemulsifier, and dried to obtain the high-content lutein ester microcapsule powder; the temperature of the second coemulsification treatment is 5-15℃, the vacuum degree is 0.035-0.045 MPa and the emulsification time is 15-30 min.

2. The high-content lutein ester microcapsule powder according to claim 1, characterized in that, By weight, the raw materials of the high-content lutein ester microcapsule powder include 12.5-32 parts of lutein ester crystals, 1.5-2 parts of emulsifier a, 1.5-2 parts of emulsifier b, 0.001-0.003 parts of fat-soluble antioxidant, 2-4 parts of water-soluble antioxidant, 35-50 parts of carrier, and 15-30 parts of filler material.

3. The high-content lutein ester microcapsule powder according to claim 1, characterized in that, The emulsifier a and emulsifier b are each independently selected from any one or a combination of at least two of sucrose fatty acid esters, monoglyceride fatty acid esters, diglyceride fatty acid esters, Tween or sorbitan monoglyceride fatty acid esters.

4. The high-content lutein ester microcapsule powder according to claim 1, wherein the fat-soluble antioxidant includes ascorbyl palmitate.

5. The high-content lutein ester microcapsule powder according to claim 1, wherein the water-soluble antioxidant comprises sodium ascorbate.

6. The high-content lutein ester microcapsule powder according to claim 1, characterized in that, The carrier comprises any one or a combination of at least two of the following: modified starch, gum arabic, octenyl succinate monoarabic ester, gelatin, pectin, or sodium alginate.

7. The high-content lutein ester microcapsule powder according to claim 6, wherein the carrier comprises modified starch and / or gum arabic.

8. The high-content lutein ester microcapsule powder according to claim 1, wherein the filling material comprises any one or a combination of at least two of sucrose, glucose, glucose syrup, isomaltooligosaccharide, fructooligosaccharide, solid corn syrup, xylitol, erythritol, resistant dextrin, or fructooligosaccharide.

9. The high-content lutein ester microcapsule powder according to claim 1, wherein the lutein ester content in the high-content lutein ester microcapsule powder is 10-25.5%.

10. The high-content lutein ester microcapsule powder according to claim 1, characterized in that, The particle size of the first coemulsion is 10-30 μm.

11. The high-content lutein ester microcapsule powder according to claim 1, wherein the particle size of the second coemulsifier is <1 μm.

12. The high-content lutein ester microcapsule powder according to claim 1, characterized in that, The preparation method of the high-content lutein ester microcapsule powder includes the following steps: (1) Lutein ester crystals, fat-soluble antioxidants, emulsifier a and carrier are mixed and subjected to a first co-emulsification treatment at -25~-20℃ and vacuum degree 0.008-0.012MPa for 15-30 min to obtain a first co-emulsifier with a particle size of 10-30 μm; (2) The first coemulsifier obtained in step (1), the filler material, the water-soluble antioxidant, the emulsifier b and water are mixed and subjected to a second coemulsification treatment at 5-15℃ and vacuum degree 0.035-0.045 MPa for 15-30 min to obtain a second coemulsifier with a particle size <1 μm. The second coemulsifier is dried to obtain the high content lutein ester microcapsule powder.

13. The use of a high-content lutein ester microcapsule powder as described in any one of claims 1-12 in beverages or effervescent tablets.

14. A sugar-free lutein ester beverage, characterized in that, The sugar-free lutein ester beverage comprises, by weight: 0.1-0.5 parts of the high-content lutein ester microcapsule powder as described in any one of claims 1-12, 5-30 parts of xylitol, 1-5 parts of apple juice, 0.01-0.05 parts of apple flavoring, 0.1-3 parts of citric acid, and 10-100 parts of water.

15. A lutein ester effervescent microtablet, characterized in that, The lutein ester effervescent microplates comprise, by weight, 20-40 parts of the high-content lutein ester microcapsule powder as described in any one of claims 1-12, 15-25 parts of citric acid, 10-20 parts of sodium bicarbonate, 2-8 parts of mannitol, 20-30 parts of lactose, 1-3 parts of flavoring agent, and 2-4 parts of leucine.

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