Beta-cyclodextrin-chitosan gel microspheres, methods of making and using and methods of making collagen peptides

Abstract

The application discloses beta-cyclodextrin-chitosan gel microspheres, a preparation method and application thereof, and a preparation method of collagen peptide. The preparation method of the beta-cyclodextrin-chitosan gel microspheres comprises the following steps: mixing beta-cyclodextrin with a first alkali solution for dispersion, adding chitosan, then adding a sodium trimetaphosphate aqueous solution, and performing cross-linking reaction to prepare a beta-cyclodextrin-chitosan cross-linking product; mixing the beta-cyclodextrin-chitosan cross-linking product with an oil solution containing a surfactant, performing emulsification, washing and drying to prepare the beta-cyclodextrin-chitosan gel microspheres. The prepared beta-cyclodextrin-chitosan gel microspheres can efficiently adsorb aldehydes and other undesirable flavor substances, and are applied to a preparation process of collagen peptide and other food raw materials, so that the fishy taste, bitter taste or peculiar smell and other undesirable flavors of the food raw materials can be reduced.

Description

Technical Field

[0001] This application belongs to the field of food processing aids technology, and relates to β-cyclodextrin-chitosan gel microspheres, their preparation methods and applications, and methods for preparing collagen peptides. Background Technology

[0002] Naturally derived food ingredients rich in protein or fat, such as collagen from fish skin or animals, often possess unpleasant flavors, such as fishy, ​​bitter, or off-flavors. Traditionally, to improve the sensory quality of such products, flavorings or flavor masking agents are added to cover these unpleasant flavors, thereby increasing the overall acceptability of the product. However, the addition of flavorings does not fundamentally eliminate the chemical components that produce off-flavors, and long-term or excessive intake of certain synthetic flavorings may pose potential health risks, such as increasing the metabolic burden on the liver and kidneys; potentially irritating the gastrointestinal tract and causing discomfort; and possibly causing skin allergies, leading to symptoms such as itching and redness. Furthermore, the overly strong flavors of artificial flavorings can be unfriendly to consumers seeking a natural taste. Therefore, developing a substance that can remove unpleasant flavors from food ingredients has significant application value. Summary of the Invention

[0003] Therefore, it is necessary to provide a method for preparing β-cyclodextrin-chitosan gel microspheres that can reduce unpleasant flavors in food ingredients, as well as a method for preparing collagen peptides.

[0004] In some embodiments, a method for preparing β-cyclodextrin-chitosan gel microspheres is provided, comprising the following steps:

[0005] β-Cyclodextrin was dispersed by mixing with the first alkaline solution, chitosan was added, and then sodium trimetaphosphate aqueous solution was added to carry out a cross-linking reaction to prepare a β-cyclodextrin-chitosan cross-linked product.

[0006] The β-cyclodextrin-chitosan crosslinked product was mixed with an oil solution containing a surfactant, emulsified, washed, and dried to prepare the β-cyclodextrin-chitosan gel microspheres.

[0007] In some embodiments, the provided method for preparing β-cyclodextrin-chitosan gel microspheres satisfies one or more of the following conditions:

[0008] (1) The mass-to-volume ratio of the β-cyclodextrin to the first alkaline solution is (0.5~1) g: 5 mL;

[0009] (2) The first alkaline solution contains a first alkali and water, and the mass-volume ratio of the first alkali to the water is (3~8) g: 10 mL;

[0010] (3) The dispersion temperature is 25℃~40℃, the dispersion time is 0.5h~1h, and the dispersion is carried out at a stirring speed of 100r / min~500r / min.

[0011] In some embodiments, the provided method for preparing β-cyclodextrin-chitosan gel microspheres satisfies one or both of the following conditions:

[0012] (1) The mass ratio of sodium trimetaphosphate to β-cyclodextrin in the sodium trimetaphosphate aqueous solution is 3:(1~3);

[0013] (2) The mass-to-volume ratio of sodium trimetaphosphate to water in the sodium trimetaphosphate aqueous solution is 3g:(3~8)mL;

[0014] (3) In the step of adding sodium trimetaphosphate aqueous solution, the time required for each 3g of sodium trimetaphosphate added is greater than or equal to 30min.

[0015] In some embodiments, in the method for preparing β-cyclodextrin-chitosan gel microspheres, the mass ratio of chitosan to β-cyclodextrin is 1:(1~5).

[0016] In some embodiments, the provided method for preparing β-cyclodextrin-chitosan gel microspheres satisfies one or both of the following conditions:

[0017] (1) The temperature of the cross-linking reaction is 30℃~60℃, and the time of the cross-linking reaction is 1h~3h;

[0018] (2) The emulsification temperature is 50℃~80℃ and the emulsification time is 3h~6h.

[0019] In some embodiments, the provided method for preparing β-cyclodextrin-chitosan gel microspheres satisfies one or more of the following conditions:

[0020] (1) The mass ratio of the chitosan to the oil solution containing the surfactant is (1~1.5):(20~40);

[0021] (2) The oil solution containing surfactant includes one or two of Twine and Span, and the oil contains isopropyl myristate; optionally, the surfactant includes Twine and Span, and the mass ratio of Twine and Span is (1~3):(1~3); optionally, the mass ratio of the surfactant to the oil is 1:(20~50).

[0022] In some embodiments, β-cyclodextrin-chitosan gel microspheres are provided, prepared using the aforementioned preparation method.

[0023] In some embodiments, the β-cyclodextrin-chitosan gel microspheres are provided for use in removing undesirable flavors from food ingredients;

[0024] Optionally, the food ingredient includes at least one of animal-derived collagen tissues.

[0025] In some embodiments, a method for preparing collagen peptides is provided, comprising the following steps:

[0026] Fish skin is soaked in a second alkaline solution, and solid-liquid separation is performed to prepare soaked fish skin.

[0027] In the presence of a solvent, the soaked fish skin, alkaline protease, and β-cyclodextrin-chitosan gel microspheres are mixed and subjected to enzymatic hydrolysis. The enzyme is then inactivated, the solid and liquid are separated, and the liquid is collected to prepare the collagen peptide.

[0028] In some embodiments, the provided method for preparing collagen peptides satisfies one or more of the following conditions:

[0029] (1) The second alkaline solution contains a second alkali and water, the second alkali including sodium hydroxide, and the mass ratio of the second alkali to the water is (0.5~1):(10);

[0030] (2) Soaking time is (30~45) min;

[0031] (3) The amount of β-cyclodextrin-chitosan gel microspheres added, based on the dry weight of fish skin, is 5wt%~10wt%;

[0032] (4) The amount of alkaline protease added is 0.3wt%~0.5wt% based on the dry weight of the fish skin;

[0033] (5) The mass-to-volume ratio of the fish skin to the solvent, based on the dry weight of the fish skin, is 1 g: (5~8) mL;

[0034] (6) The temperature of the enzymatic hydrolysis reaction is 45℃~65℃, and the time of the enzymatic hydrolysis reaction is 3h~8h;

[0035] (7) The solvent is water.

[0036] In the aforementioned method for preparing β-cyclodextrin-chitosan gel microspheres, an alkaline solution is used simultaneously as a solvent for β-cyclodextrin and an alkaline medium for subsequent cross-linking reactions. A stepwise strategy is employed, first allowing sodium trimetaphosphate to form a preliminary cross-linking network with β-cyclodextrin before adding chitosan, thus avoiding competitive reactions. Subsequently, an oil solution containing surfactants is used to disperse the reaction system into a water-in-oil emulsion, which can form microspheres or nanoparticles with amphiphilic structures within microdroplets. Finally, washing effectively removes alkali, emulsifiers, and unreacted substances, ensuring product purity. The overall design achieves synergistic control over the product's structure, morphology, and properties.

[0037] The prepared β-cyclodextrin-chitosan gel microspheres can efficiently adsorb undesirable flavor substances such as aldehydes. When applied to the preparation of food raw materials such as collagen peptides, they can reduce undesirable flavors such as fishy, ​​bitter or off-flavors. Attached Figure Description

[0038] To more clearly illustrate the technical solutions in the embodiments and examples of this application, and to more completely understand this application and its beneficial effects, the accompanying drawings used in the description of the embodiments or examples will be briefly introduced below. Obviously, the drawings described below are merely some embodiments of this application. Those skilled in the art can obtain other drawings based on these drawings without any creative effort.

[0039] Figure 1 Microscopic images (40×) of the microspheres prepared in Example 1 and Comparative Example 1 are shown, where A is a microscopic image of the microspheres prepared in Example 1 and B is a microscopic image of the microspheres prepared in Comparative Example 1. The scale bar is 20 μm.

[0040] Figure 2 Radar graphs for sensory evaluation of collagen peptides prepared using the various examples and comparative examples;

[0041] Figure 3 This is a comparison chart showing changes from different sensors. Detailed Implementation

[0042] To facilitate understanding of the present invention, a more complete description will be given below with reference to the accompanying drawings. Preferred embodiments of the invention are shown in the drawings. However, the invention can be implemented in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided to provide a thorough and complete understanding of the disclosure of the invention.

[0043] It should be noted that when a component is said to be "fixed to" another component, it can be directly attached to the other component or there may be an intervening component. When a component is said to be "connected to" another component, it can be directly connected to the other component or there may be an intervening component.

[0044] Unless otherwise defined, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention pertains. The terminology used herein in the description of the invention is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and / or" as used herein includes any and all combinations of one or more of the associated listed items.

[0045] Unless otherwise stated or in case of contradiction, the terms or phrases used herein shall have the following meanings:

[0046] The terms "and / or," "or / and," and "and / or" as used in this application encompass any one of two or more related listed items, as well as any and all combinations of the related listed items. These arbitrary and all combinations include any two related listed items, any more related listed items, or a combination of all related listed items. It should be noted that when at least three items are connected using at least two conjunctions selected from "and / or," "or / and," and "and / or," it should be understood that in this application, the technical solution undoubtedly includes solutions connected by "logical AND," and also undoubtedly includes solutions connected by "logical OR." For example, "A and / or B" includes three parallel solutions: A, B, and "a combination of A and B."

[0047] In this application, the terms "multiple", "various", "multiple times", "multi-dimensional", etc., unless otherwise specified, refer to a quantity greater than or equal to 2. For example, "one or more" means one or more than or equal to two.

[0048] The terms “combinations thereof,” “any combination thereof,” and “any combination thereof” as used in this application include all suitable combinations of any two or more of the listed items.

[0049] In this application, the term "suitable" as used in "suitable combination", "suitable method", "any suitable method", etc., refers to the ability to implement the technical solution of this application, solve the technical problem of this application, and achieve the expected technical effect of this application.

[0050] In this application, terms such as "preferred," "better," "more suitable," and "ideal" are merely used to describe implementation methods or embodiments that achieve better results, and should be understood not to limit the scope of protection of this application.

[0051] In this application, terms such as "further," "even further," and "particularly" are used to describe purposes and indicate differences in content, but should not be construed as limiting the scope of protection of this application.

[0052] In this application, "optionally," "optionally," and "optional" mean that something is optional, that is, it means that it is selected from either "with" or "without." If there are multiple "optional" entries in a technical solution, unless otherwise specified, and there are no contradictions or mutual constraints, each "optional" entry shall be independent.

[0053] In this invention, the terms "first aspect," "second aspect," "third aspect," and "fourth aspect," etc., are used for descriptive purposes only and should not be construed as indicating or implying relative importance or quantity, nor should they be construed as implicitly indicating the importance or quantity of the indicated technical features. Moreover, "first," "second," "third," and "fourth," etc., serve only as a non-exhaustive enumeration and should be understood not to constitute a closed limitation on quantity.

[0054] In this application, the technical features described in an open-ended manner include both closed technical solutions consisting of the listed features and open technical solutions that include the listed features.

[0055] In this application, numerical intervals (i.e., numerical ranges) are involved. Unless otherwise specified, the selected numerical distributions within the aforementioned numerical intervals are considered continuous and include the two endpoints (i.e., the minimum and maximum values) of the numerical range, as well as every value between these two endpoints. Unless otherwise specified, when a numerical interval refers only to integers within that interval, it includes the two endpoint integers of the numerical range, as well as every integer between the two endpoints. In this document, this is equivalent to directly listing every integer. For example, if t is an integer selected from 1 to 10, it means that t is any integer selected from the group of integers consisting of 1, 2, 3, 4, 5, 6, 7, 8, 9, and 10. Furthermore, when multiple ranges are provided to describe features or characteristics, these ranges can be merged. In other words, unless otherwise specified, the ranges disclosed herein should be understood to include any and all subranges to which they are included.

[0056] Unless otherwise specified, the temperature parameters in this application are permitted to be either constant-temperature treatment or variations within a certain temperature range. It should be understood that the constant-temperature treatment allows temperature fluctuations within the precision range of the instrument control, such as ±5℃, ±4℃, ±3℃, ±2℃, or ±1℃.

[0057] In this application, % (w / w) and wt% both represent weight percentage, % (v / v) refers to volume percentage, and % (w / v) refers to mass-volume percentage.

[0058] In this application, "room temperature" generally refers to 5℃~30℃, and more preferably 25±5℃.

[0059] In some embodiments, a method for preparing β-cyclodextrin-chitosan gel microspheres is provided, comprising the following steps:

[0060] β-Cyclodextrin was dispersed by mixing with the first alkaline solution, chitosan was added, and then sodium trimetaphosphate aqueous solution was added to carry out a cross-linking reaction to prepare a β-cyclodextrin-chitosan cross-linked product.

[0061] The β-cyclodextrin-chitosan crosslinked product was mixed with an oil solution containing a surfactant, emulsified, washed, and dried to prepare β-cyclodextrin-chitosan gel microspheres.

[0062] The β-cyclodextrin-chitosan gel microspheres prepared by the provided method can adsorb small molecule flavor substances such as aldehydes and ketones that can produce unpleasant flavors, as well as various unpleasant flavor substances such as fat oxidation and putrefaction.

[0063] In some embodiments, the provided method for preparing β-cyclodextrin-chitosan gel microspheres uses a mass-to-volume ratio of β-cyclodextrin to the first alkaline solution of (0.5~1) g:5 mL, for example, 0.5 g:5 mL, 0.6 g:5 mL, 0.7 g:5 mL, 0.8 g:5 mL, 0.9 g:5 mL, 1.0 g:5 mL, etc., or any range of the two aforementioned ratios.

[0064] In some embodiments, the method for preparing β-cyclodextrin-chitosan gel microspheres includes a first alkali solution containing a first alkali and water, wherein the mass-volume ratio of the first alkali to water is (3~8) g:10 mL, for example, 3 g:10 mL, 4 g:10 mL, 5 g:10 mL, 6 g:10 mL, 7 g:10 mL, 8 g:10 mL, etc., or any range of the two aforementioned ratios.

[0065] In some embodiments, the method for preparing β-cyclodextrin-chitosan gel microspheres involves dispersing at a temperature of 25°C to 40°C for a time of 0.5 h to 1 h, and at a stirring speed of 100 r / min to 500 r / min. For example, the temperature can be 25°C, 30°C, 35°C, 40°C, etc., the time can be 0.5 h, 0.6 h, 0.7 h, 0.8 h, 0.9 h, 1.0 h, etc., and the stirring speed can be 100 r / min, 200 r / min, 300 r / min, 400 r / min, 500 r / min, etc., and the values ​​of each parameter can also be ranges composed of any two of the aforementioned values.

[0066] In some embodiments, the provided method for preparing β-cyclodextrin-chitosan gel microspheres uses a sodium trimetaphosphate aqueous solution with a mass ratio of sodium trimetaphosphate to β-cyclodextrin of 3:(1~3), for example, 3:1, 3:1.5, 3:2, 3:2.5, 3:3, etc., or any range of the aforementioned two ratios.

[0067] In some embodiments, the provided method for preparing β-cyclodextrin-chitosan gel microspheres uses a sodium trimetaphosphate aqueous solution with a mass-to-volume ratio of sodium trimetaphosphate to water of 3g:(3~8)mL, for example, 3g:3mL, 3g:4mL, 3g:5mL, 3g:6mL, 3g:7mL, 3g:8mL, etc., or any range of the two aforementioned ratios.

[0068] In some embodiments, the preparation method of β-cyclodextrin-chitosan gel microspheres provides a time of greater than or equal to 30 minutes required for each 3g of sodium trimetaphosphate added in the step of adding sodium trimetaphosphate aqueous solution.

[0069] In some embodiments, in the provided method for preparing β-cyclodextrin-chitosan gel microspheres, the mass ratio of chitosan to β-cyclodextrin is 1:(1~5), for example, 1:1, 1:2, 1:3, 1:4, 1:5, etc., or it can be a range of any two of the aforementioned ratios.

[0070] In some embodiments, the cross-linking reaction temperature of the provided β-cyclodextrin-chitosan gel microspheres is 30℃~60℃, and the cross-linking reaction time is 1h~3h; for example, the temperature can be 30℃, 40℃, 50℃, 60℃, etc., and the time can be 1h, 1.5h, 2h, 2.5h, 3h, etc., and the values ​​of each parameter can also be ranges composed of any two of the aforementioned values.

[0071] In some embodiments, the preparation method of β-cyclodextrin-chitosan gel microspheres provides an emulsification temperature of 50℃~80℃ and an emulsification time of 3h~6h; for example, the temperature can be 50℃, 60℃, 70℃, 80℃, etc., and the time can be 3h, 4h, 5h, 6h, etc., and the values ​​of each parameter can also be ranges composed of any two of the aforementioned values.

[0072] In some embodiments, the provided method for preparing β-cyclodextrin-chitosan gel microspheres uses a mass ratio of chitosan to an oil solution containing a surfactant of (1~1.5):(20~40), for example, 1:20, 1:25, 1:30, 1:35, 1:40, 1.5:20, 1.5:25, 1.5:30, 1.5:35, 1.5:40, etc., or any range of the aforementioned two ratios.

[0073] In some embodiments, the provided method for preparing β-cyclodextrin-chitosan gel microspheres includes an oil solution containing a surfactant, wherein the surfactant includes one or both of Tween and Span, and the oil contains isopropyl myristate.

[0074] In some embodiments, the surfactant comprises Tween and Span in a mass ratio of (1~3):(1~3), for example, 1:1, 1:2, 1:3, 2:1, 2:2, 2:3, 3:1, 3:2, 3:3, etc., or any range of the two aforementioned ratios.

[0075] In some embodiments, the mass ratio of surfactant to oil is 1:(20~50), for example, 1:20, 1:25, 1:30, 1:35, 1:40, 1:45, 1:50, etc., or it can be a range of any two of the aforementioned ratios.

[0076] In some embodiments, β-cyclodextrin-chitosan gel microspheres are provided, prepared using the aforementioned preparation method.

[0077] In some embodiments, the aforementioned β-cyclodextrin-chitosan gel microspheres are provided for use in removing undesirable flavors from food ingredients.

[0078] In some embodiments, the food ingredients provided in the provided applications include at least one of animal-derived collagen tissues.

[0079] In some embodiments, a method for preparing collagen peptides is provided, comprising the following steps:

[0080] Fish skin is soaked in a second alkaline solution, and solid-liquid separation is performed to prepare soaked fish skin.

[0081] In the presence of a solvent, soaked fish skin, alkaline protease, and the aforementioned β-cyclodextrin-chitosan gel microspheres are mixed and subjected to enzymatic hydrolysis. The enzyme is then inactivated, the solid and liquid are separated, and the liquid is collected to prepare collagen peptides.

[0082] Applying the provided β-cyclodextrin-chitosan gel microspheres to the preparation of food ingredients such as collagen peptides can reduce unpleasant flavors in the prepared collagen peptides. This can reduce the amount of flavoring added in downstream products containing these collagen peptides, thereby lowering product formulation costs, maximizing the preservation of the original taste and texture of the raw materials, avoiding allergic reactions and gastrointestinal irritation, and ensuring the flavor and texture of beverages while maximizing product safety.

[0083] Compared with adsorbents such as activated carbon and diatomaceous earth, the collagen peptides prepared using the β-cyclodextrin-chitosan gel microspheres provided in this application have a higher yield.

[0084] In some embodiments, the provided method for preparing collagen peptides includes a second alkali solution containing a second alkali and water. The second alkali includes sodium hydroxide, and the mass ratio of the second alkali to water is (0.5~1):(10), for example, 0.5:10, 0.6:10, 0.7:10, 0.8:10, 0.9:10, 1.0:10, etc., or it can be a range of any two of the aforementioned ratios.

[0085] In some embodiments, the preparation method of collagen peptides provides a soaking time of 30 min to 45 min, for example, 30 min, 32 min, 35 min, 38 min, 40 min, 42 min, 45 min, etc., or it can be a range composed of any two of the aforementioned values.

[0086] In some embodiments, the collagen peptide preparation method provides that the amount of β-cyclodextrin-chitosan gel microspheres added, based on the dry weight of fish skin, is 5wt% to 10wt%, for example, 5wt%, 6wt%, 7wt%, 8wt%, 9wt%, 10wt%, etc., or can be any range of the two aforementioned values.

[0087] In some embodiments, the provided method for preparing collagen peptides involves adding alkaline protease at a rate of 0.3 wt% to 0.5 wt% based on the dry weight of fish skin, for example, 0.3 wt%, 0.35 wt%, 0.4 wt%, 0.45 wt%, 0.5 wt%, etc., or any range of the aforementioned two values.

[0088] In some embodiments, the collagen peptide preparation method provides a mass-volume ratio of fish skin to solvent of 1g:(5~8)mL based on the dry weight of fish skin, for example, 1g:5mL, 1g:6mL, 1g:7mL, 1g:8mL, etc., or any range of the two aforementioned ratios.

[0089] In some embodiments, the provided method for preparing collagen peptides involves an enzymatic hydrolysis reaction at a temperature of 45°C to 65°C and a reaction time of 3 hours to 8 hours. For example, the temperature can be 45°C, 50°C, 55°C, 60°C, 65°C, etc., and the time can be 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, etc. The values ​​of each parameter can also be ranges composed of any two of the aforementioned values.

[0090] In some embodiments, the provided method for preparing collagen peptides uses water as the solvent.

[0091] The following are specific embodiments. They are intended to provide a more detailed description of this application to help those skilled in the art and researchers better understand it. The technical conditions described do not constitute any limitation on this application. Any modifications made within the scope of the claims of this application are protected by the claims.

[0092] Unless otherwise stated, all raw materials and reagents used in the following examples are commercially available or can be prepared by known methods. Experimental methods not specifying particular conditions in the examples were performed under conventional conditions, such as those described in literature, books, or methods recommended by the manufacturer.

[0093] Example 1

[0094] (1) Preparation of NaOH solution and β-cyclodextrin dispersion: Accurately weigh 5g of sodium hydroxide (NaOH), dissolve it in 10mL of deionized water, and stir evenly to obtain NaOH solution; then weigh 2g of β-cyclodextrin, add it to the above NaOH solution, heat the system to 30℃, and continue stirring for 0.5h until β-cyclodextrin is evenly dispersed;

[0095] (2) Crosslinking reaction and chitosan addition: After the β-cyclodextrin is evenly dispersed, add 1g of chitosan and stir at 30℃ for 15min to allow the chitosan to swell and mix thoroughly with the β-cyclodextrin. Dissolve 3.0g of sodium tripolyphosphate in 5mL of deionized water and slowly add it dropwise to the above solution over 30min, stirring continuously during the addition. After the addition is complete, heat the system to 50℃ and continue the reaction for 60min. Then add 30g of isopropyl myristate mixed with 1g of Span 80 and Tween 20 (mass ratio 3:1). Heat the system to 60℃ and react for 4h.

[0096] (3) Post-processing of products: After the reaction is completed, the reaction products are washed with hydrochloric acid, ethanol and distilled water in sequence to remove impurities and unreacted raw materials. After washing, the powder is dried to obtain β-cyclodextrin-chitosan gel microspheres.

[0097] (4) Soak the skin of the large yellow croaker in an alkaline solution for 30 min. The alkaline solution contains sodium hydroxide and water in a mass ratio of 1:10. Mix the cleaned fish skin, alkaline protease, β-cyclodextrin-chitosan gel microspheres and water. The mass-volume ratio of the dry fish skin to the solvent water is 1 g: 6 mL. The mass of the alkaline protease added is 0.5% of the dry weight of the fish skin, and the mass of the β-cyclodextrin-chitosan gel microspheres added is 5% of the dry weight of the fish skin. Under 50℃ conditions, stir at 200 r / min for 4 h to enzymatically hydrolyze the fish skin. There are no obvious large pieces of fish skin. Then, heat at 95℃ for 10 min to inactivate the enzyme.

[0098] (5) Centrifuge the enzyme hydrolysate at 500 r / min for 3 min, filter the supernatant with filter paper, and freeze-dry the filtered liquid to obtain collagen peptide samples.

[0099] Example 2

[0100] (1) Preparation of NaOH solution and β-cyclodextrin dispersion: Accurately weigh 5g of sodium hydroxide (NaOH), dissolve it in 10mL of deionized water, and stir evenly to obtain NaOH solution; then weigh 2g of β-cyclodextrin, add it to the above NaOH solution, heat the system to 40℃, and continue stirring for 0.5h until β-cyclodextrin is evenly dispersed;

[0101] (2) Crosslinking reaction and chitosan addition: After the β-cyclodextrin is evenly dispersed, add 1g of chitosan and stir at 30℃ for 15min to allow the chitosan to swell and mix thoroughly with the β-cyclodextrin. Dissolve 3.0g of sodium tripolyphosphate in 5mL of deionized water and slowly add it dropwise to the above solution over 30min, stirring continuously during the addition. After the addition is complete, heat the system to 50℃ and continue the reaction for 60min. Then add 30g of isopropyl myristate mixed with 1g of Span 80 and Tween 20 (mass ratio 3:1). Heat the system to 60℃ and react for 4h.

[0102] (3) Post-processing of products: After the reaction is completed, the reaction products are washed with hydrochloric acid, ethanol and distilled water in sequence to remove impurities and unreacted raw materials. After washing, the powder is dried to obtain β-cyclodextrin-chitosan gel microspheres.

[0103] (4) Soak the skin of the large yellow croaker in an alkaline solution for 30 min. The alkaline solution contains sodium hydroxide and water in a mass ratio of 1:10. Mix the cleaned fish skin, alkaline protease, β-cyclodextrin-chitosan gel microspheres and water. The mass-volume ratio of the dry fish skin to the solvent water is 1 g: 8 mL. The mass of the alkaline protease added is 0.5% of the dry weight of the fish skin, and the mass of the β-cyclodextrin-chitosan gel microspheres added is 10% of the dry weight of the fish skin. Under 50℃ conditions, stir at 200 r / min for 8 h to enzymatically hydrolyze the fish skin. There are no obvious large pieces of fish skin. Then, heat at 95℃ for 10 min to inactivate the enzyme.

[0104] (5) Centrifuge the enzyme hydrolysate at 500 r / min for 3 min, filter the supernatant with filter paper, and freeze-dry the filtered liquid to obtain collagen peptide samples.

[0105] Example 3

[0106] (1) Preparation of NaOH solution and β-cyclodextrin dispersion: Accurately weigh 5g of sodium hydroxide (NaOH), dissolve it in 10mL of deionized water, and stir evenly to obtain NaOH solution; then weigh 2g of β-cyclodextrin, add it to the above NaOH solution, heat the system to 30℃, and continue stirring for 0.5h until β-cyclodextrin is evenly dispersed;

[0107] (2) Crosslinking reaction and chitosan addition: After the β-cyclodextrin is evenly dispersed, add 1g of chitosan and stir at 30℃ for 15min to allow the chitosan to swell and mix thoroughly with the β-cyclodextrin. Dissolve 3.0g of sodium tripolyphosphate in 5mL of deionized water and slowly add it dropwise to the above solution over 30min, stirring continuously during the addition. After the addition is complete, heat the system to 50℃ and continue the reaction for 90min. Then add 30g of isopropyl myristate mixed with 1g of Span 80 and Tween 20 (mass ratio 3:1). Heat the system to 60℃ and react for 4h.

[0108] (3) Post-processing of products: After the reaction is completed, the reaction products are washed with hydrochloric acid, ethanol and distilled water in sequence to remove impurities and unreacted raw materials. After washing, the powder is dried to obtain β-cyclodextrin-chitosan gel microspheres.

[0109] (4) The skin of the large yellow croaker was soaked and washed in an alkaline solution, and then enzymatically hydrolyzed with alkaline protease. The alkaline solution contained sodium hydroxide and water in a mass ratio of 1:10. The washed fish skin, alkaline protease, β-cyclodextrin-chitosan gel microspheres and water were mixed. The mass-volume ratio of the dry fish skin to the solvent water was 1 g: 6 mL. The mass of the alkaline protease added was 0.5% of the dry weight of the fish skin, and the mass of the β-cyclodextrin-chitosan gel microspheres added was 5% of the dry weight of the fish skin. The fish skin was stirred at 200 r / min for 4 h at 50 °C. No large pieces of fish skin were found. Then the fish skin was heated at 95 °C for 10 min to inactivate the enzyme.

[0110] (5) Centrifuge the enzyme hydrolysate at 500 r / min for 3 min, filter the supernatant with filter paper, and freeze-dry the filtered liquid to obtain collagen peptide samples.

[0111] Example 4

[0112] (1) Preparation of NaOH solution and β-cyclodextrin dispersion: Accurately weigh 5g of sodium hydroxide (NaOH), dissolve it in 10mL of deionized water, and stir evenly to obtain NaOH solution; then weigh 2g of β-cyclodextrin, add it to the above NaOH solution, heat the system to 30℃, and continue stirring for 0.5h until β-cyclodextrin is evenly dispersed;

[0113] (2) Crosslinking reaction and chitosan addition: After the β-cyclodextrin is evenly dispersed, add 1g of chitosan and stir at 30℃ for 15min to allow the chitosan to swell and mix thoroughly with the β-cyclodextrin. Dissolve 3.0g of sodium tripolyphosphate in 5mL of deionized water and slowly add it dropwise to the above solution over 30min, stirring continuously during the addition. After the addition is complete, heat the system to 50℃ and continue the reaction for 60min. Then add 25g of isopropyl myristate mixed with 1g of Span 80 and Tween 20 (mass ratio 3:1). Heat the system to 60℃ and react for 4h.

[0114] (3) Post-processing of products: After the reaction is completed, the reaction products are washed with hydrochloric acid, ethanol and distilled water in sequence to remove impurities and unreacted raw materials. After washing, the powder is dried to obtain β-cyclodextrin-chitosan gel microspheres.

[0115] (4) The skin of the large yellow croaker was soaked and washed in an alkaline solution containing sodium hydroxide and water in a mass ratio of 1:10. The washed fish skin, alkaline protease, β-cyclodextrin-chitosan gel microspheres and water were mixed. The mass-volume ratio of the dried fish skin to the solvent water was 1 g: 6 mL. The mass of the alkaline protease added was 0.5% of the dry weight of the fish skin, and the mass of the β-cyclodextrin-chitosan gel microspheres added was 5% of the dry weight of the fish skin. The fish skin was stirred at 200 r / min at 50 °C for 4 h without any obvious large pieces of fish skin. Then, the fish skin was heated at 95 °C for 10 min to inactivate the enzyme.

[0116] (5) Centrifuge the enzyme hydrolysate at 500 r / min for 3 min, filter the supernatant with filter paper, and freeze-dry the filtered liquid to obtain collagen peptide samples.

[0117] Comparative Example 1

[0118] (1) Preparation of NaOH solution and β-cyclodextrin dispersion: Accurately weigh 5g of sodium hydroxide (NaOH), dissolve it in 10mL of deionized water, and stir evenly to obtain NaOH solution; then weigh 2g of β-cyclodextrin, add it to the above NaOH solution, heat the system to 30℃, and continue stirring for 0.5h until β-cyclodextrin is evenly dispersed;

[0119] (2) Crosslinking reaction and chitosan addition: After the β-cyclodextrin is evenly dispersed, 1g of chitosan is added, the system temperature is maintained, and the reaction continues for 90min; then 30g of isopropyl myristate mixed with 1g Span 80 and Tween 20 (mass ratio 3:1) is added, the mixture is stirred quickly and evenly, and the system is heated to 60℃ and reacted for 4h.

[0120] (3) Post-processing of products: After the reaction is completed, the reaction products are washed with hydrochloric acid, ethanol and distilled water in sequence to remove impurities and unreacted raw materials. After washing, the powder is dried to obtain β-cyclodextrin-chitosan gel microspheres.

[0121] (4) Soak the skin of the large yellow croaker in an alkaline solution for 30 min. The alkaline solution contains sodium hydroxide and water in a mass ratio of 1:10. Mix the cleaned fish skin, alkaline protease, β-cyclodextrin-chitosan gel microspheres and water. The mass-volume ratio of the dry fish skin to the solvent water is 1 g: 6 mL. The mass of the alkaline protease added is 0.5% of the dry weight of the fish skin, and the mass of the β-cyclodextrin-chitosan gel microspheres added is 5% of the dry weight of the fish skin. Under 50℃ conditions, stir at 200 r / min for 4 h to enzymatically hydrolyze the fish skin. There are no obvious large pieces of fish skin. Then, heat at 95℃ for 10 min to inactivate the enzyme.

[0122] (5) Centrifuge the enzyme hydrolysate at 500 r / min for 3 min, filter the supernatant with filter paper, and freeze-dry the filtered liquid to obtain collagen peptide samples.

[0123] Comparative Example 2

[0124] (1) Preparation of NaOH solution and β-cyclodextrin dispersion: Accurately weigh 5g of sodium hydroxide (NaOH), dissolve it in 10mL of deionized water, and stir evenly to obtain NaOH solution; then weigh 2g of β-cyclodextrin, add it to the above NaOH solution, heat the system to 30℃, and continue stirring for 0.5h until β-cyclodextrin is evenly dispersed;

[0125] (2) Cross-linking reaction and addition of chitosan: After the β-cyclodextrin is evenly dispersed, add 1g of chitosan and stir at 30℃ for 15min to allow the chitosan to swell and mix thoroughly with the β-cyclodextrin. Dissolve 3.0g of sodium tripolyphosphate in 5mL of deionized water and slowly add it dropwise to the above solution over 30min, stirring continuously during the addition. After the addition is complete, raise the temperature of the system to 50℃ and continue the reaction for 60min. Add 30g of isopropyl myristate, stir quickly and evenly, raise the temperature of the system to 60℃, and react for 4h.

[0126] (3) Post-processing of products: After the reaction is completed, the reaction products are washed with hydrochloric acid, ethanol and distilled water in sequence to remove impurities and unreacted raw materials. After washing, the powder is dried to obtain β-cyclodextrin-chitosan gel microspheres.

[0127] (4) Soak the skin of the large yellow croaker in an alkaline solution for 30 min. The alkaline solution contains sodium hydroxide and water in a mass ratio of 1:10. Mix the cleaned fish skin, alkaline protease, β-cyclodextrin-chitosan gel microspheres and water. The mass-volume ratio of the dry fish skin to the solvent water is 1 g: 6 mL. The mass of the alkaline protease added is 0.5% of the dry weight of the fish skin, and the mass of the β-cyclodextrin-chitosan gel microspheres added is 5% of the dry weight of the fish skin. Under 50℃ conditions, stir at 200 r / min for 4 h to enzymatically hydrolyze the fish skin. There are no obvious large pieces of fish skin. Then, heat at 95℃ for 10 min to inactivate the enzyme.

[0128] (5) Centrifuge the enzyme hydrolysate at 500 r / min for 3 min, filter the supernatant with filter paper, and freeze-dry the filtered liquid to obtain collagen peptide samples.

[0129] Comparative Example 3

[0130] (1) Preparation of NaOH solution and β-cyclodextrin dispersion: Accurately weigh 5g of sodium hydroxide (NaOH), dissolve it in 10mL of deionized water, and stir evenly to obtain NaOH solution; then weigh 2g of β-cyclodextrin, add it to the above NaOH solution, heat the system to 30℃, and continue stirring for 0.5h until β-cyclodextrin is evenly dispersed;

[0131] (2) Crosslinking reaction: After the β-cyclodextrin is evenly dispersed, 3.0 g of sodium trimetaphosphate is dissolved in 5 mL of deionized water and slowly added dropwise to the above solution over 30 min, while stirring during the addition. After the addition is complete, the system is heated to 50 °C and the reaction continues for 60 min. Then, 30 g of isopropyl myristate mixed with 1 g of Span 80 and Tween 20 (mass ratio 3:1) is added. The system is heated to 60 °C and the reaction is carried out for 4 h.

[0132] (3) Product post-processing: After the reaction is completed, the reaction product is washed with hydrochloric acid, ethanol and distilled water in sequence to remove impurities and unreacted raw materials. After washing, the powder is dried to obtain β-cyclodextrin gel microspheres.

[0133] (4) Soak the skin of the large yellow croaker in an alkaline solution for 30 min. The alkaline solution contains sodium hydroxide and water in a mass ratio of 1:10. Mix the cleaned fish skin, alkaline protease, β-cyclodextrin-chitosan gel microspheres and water. The mass-volume ratio of the dry fish skin to the solvent water is 1 g: 6 mL. The mass of the alkaline protease added is 0.5% of the dry weight of the fish skin, and the mass of the β-cyclodextrin-chitosan gel microspheres added is 5% of the dry weight of the fish skin. Under 50℃ conditions, stir at 200 r / min for 4 h to enzymatically hydrolyze the fish skin. There are no obvious large pieces of fish skin. Then, heat at 95℃ for 10 min to inactivate the enzyme.

[0134] (5) Centrifuge the enzyme hydrolysate at 500 r / min for 3 min, filter the supernatant with filter paper, and freeze-dry the filtered liquid to obtain collagen peptide samples.

[0135] Comparative Example 4

[0136] (1) Preparation of NaOH solution and β-cyclodextrin dispersion: Accurately weigh 5g of sodium hydroxide (NaOH), dissolve it in 10mL of deionized water, and stir evenly to obtain NaOH solution; then weigh 2g of β-cyclodextrin, add it to the above NaOH solution, heat the system to 30℃, and continue stirring for 0.5h until β-cyclodextrin is evenly dispersed;

[0137] (2) Crosslinking reaction and chitosan addition: After the β-cyclodextrin is evenly dispersed, add 1g of chitosan and stir at 30℃ for 15min to allow the chitosan to swell and mix thoroughly with the β-cyclodextrin. Dissolve 3.0g of sodium trimetaphosphate in 5mL of deionized water and slowly add it dropwise to the above solution over 30min, stirring continuously during the addition. After the addition is complete, heat the system to 50℃ and continue the reaction for 60min. Then add 30g of N,N-dimethylformamide, stir rapidly until homogeneous, and heat the system to 60℃ for 4h.

[0138] (3) Post-processing of products: After the reaction is completed, the reaction products are washed with hydrochloric acid, ethanol and distilled water in sequence to remove impurities and unreacted raw materials. After washing, the powder is dried to obtain β-cyclodextrin-chitosan gel microspheres.

[0139] (4) Soak the skin of the large yellow croaker in an alkaline solution for 30 min. The alkaline solution contains sodium hydroxide and water in a mass ratio of 1:10. Mix the cleaned fish skin, alkaline protease, β-cyclodextrin-chitosan gel microspheres and water. The mass-volume ratio of the dry fish skin to the solvent water is 1 g: 6 mL. The mass of the alkaline protease added is 0.5% of the dry weight of the fish skin, and the mass of the β-cyclodextrin-chitosan gel microspheres added is 5% of the dry weight of the fish skin. Under 50℃ conditions, stir at 200 r / min for 4 h to enzymatically hydrolyze the fish skin. There are no obvious large pieces of fish skin. Then, heat at 95℃ for 10 min to inactivate the enzyme.

[0140] (5) Centrifuge the enzyme hydrolysate at 500 r / min for 3 min, filter the supernatant with filter paper, and freeze-dry the filtered liquid to obtain collagen peptide samples.

[0141] Micromorphology detection

[0142] The microstructure of the microspheres prepared in Example 1 and Comparative Example 1 was qualitatively observed using an inverted microscope. After pretreatment, the samples were laid flat in the observation area to ensure a smooth surface free of air bubbles. Bright-field observation mode was selected to complete the morphology observation, imaging, and recording. The results are as follows: Figure 1 As shown. Figure 1 In the image, A is a microscopic image of the microspheres prepared in Example 1. Figure 1 B in the figure is a microscopic image of the microspheres prepared in Comparative Example 1.

[0143] like Figure 1 The results of the A-level test showed that the microspheres prepared in Example 1 were round and uniform in size, and evenly dispersed without large-area agglomeration or flocculation. Figure 1 The results of the B test showed that no formed microspheres were observed in the microscopic image of Comparative Example 1, but significant large-scale flocculation could be seen in the image.

[0144] Test case

[0145] (1) Sensory evaluation of taste

[0146] Eight sensory evaluators aged 19-25 years with a balanced male-female ratio were selected to conduct a comprehensive evaluation of the collagen peptide samples obtained in the examples and comparative examples. The evaluation was mainly based on taste of the different large yellow croaker skin collagen peptides. The evaluation method was to prepare a 10% fish skin peptide aqueous solution and conduct taste evaluation by oral administration.

[0147] The relevant evaluation content and standards are shown in Table 1. Specifically, there were 4 male and 4 female evaluators, all of whom had received one year of sensory training and were familiar with bitterness, umami, fishiness, and sourness. The evaluators conducted blind evaluations of the samples according to the evaluation standards and gave scores for each indicator.

[0148] Table 1 Evaluation Criteria for Taste Sensory Functions

[0149]

[0150] Sensory evaluation results such as Figure 2 As shown. From Figure 2The data shows that Examples 1-4 are significantly better than Comparative Examples 1-4 in improving the fishy smell, indicating that the addition of β-cyclodextrin and chitosan cross-linked products, i.e., gel microspheres, can effectively improve the fishy smell components in fish skin hydrolysate. Among them, Examples 1-4 have a complete process to prepare effective gel microspheres that play an adsorption role, while Comparative Example 1, due to the lack of cross-linking agent, cannot successfully cross-link β-cyclodextrin and chitosan. In Comparative Example 2, the lack of emulsifier resulted in excessive cross-linking of β-cyclodextrin and chitosan, which lost its effect. In Comparative Example 3, the lack of chitosan prevented the cross-linking effect of β-cyclodextrin and chitosan from being achieved. In Comparative Example 4, N,N-dimethylformamide failed to uniformly disperse the microspheres, resulting in excessive cross-linking of the microspheres. According to relevant studies, the main causes of unpleasant odors such as fishy smell in fish skin enzymatic hydrolysate are the production of small molecule flavor substances such as aldehydes and ketones during the enzymatic hydrolysis process, as well as various unpleasant flavor substances such as fat oxidation and putrefaction. Among them, aldehydes are the main source of unpleasant flavors in enzymatic hydrolysate. Related studies have shown that reducing aldehydes can effectively alleviate the unpleasant odors in fish skin enzymatic hydrolysate.

[0151] In an alkaline environment, the electronegativity of the carbonyl oxygen on aldehydes is enhanced. The hydroxyl hydrogen on the hydrophilic outer cavity of β-cyclodextrin and the amino group on chitosan have enhanced adsorption for hydrogen protons in an alkaline environment, thus making it easier to form hydrogen bonds. Therefore, more aldehydes are adsorbed on the cross-linked gel microspheres of β-cyclodextrin and chitosan in this environment.

[0152] (2) Detection of volatile component content

[0153] The content of volatile components in the collagen peptide samples obtained in the examples and comparative examples was detected by gas chromatography-mass spectrometry (GC-MS). GC-MS data analysis of Example 1 and Comparative Example 1 were performed. The mass spectrometry data of volatile components were automatically retrieved using the NIST20.L spectral library, and the search results were manually verified. The names and molecular formulas of compounds formed based on each peak position were checked. Example 1 and Comparative Example 1 identified 27 and 25 components, respectively, accounting for 99.9% of the total components. The content of the main volatile components was obtained using the peak area normalization method, and the results are shown in Table 2.

[0154] Table 2 Main chemical components of Example 1 and Comparative Example 1

[0155]

[0156] Table 2 shows that the main volatile aldehydes are heptanal, octanal, nonanal, trans-2-octenal, 2,4-heptadienal, and benzaldehyde. In Example 1, all aldehydes showed varying degrees of reduction compared to Comparative Example 1. Studies indicate that aldehydes are the main contributors to the unpleasant fishy odor in fish skin enzymatic hydrolysis products. Adding β-cyclodextrin and chitosan cross-linked gel microspheres during enzymatic hydrolysis effectively adsorbed aldehydes, significantly reducing the aldehyde content detected by GCMS in Example 1. Meanwhile, research shows that ketones are second only to aldehydes in their role as contributors to unpleasant odors. The detection data shows that most components in Example 1 showed significant reductions compared to Comparative Example 1. Other substances, such as alcohols, esters, acids, and other components, showed little difference in flavor composition between the two processes, or substances with significant differences in composition had a relatively small impact on flavor.

[0157] (3) Electronic nose detection

[0158] This experiment used an electronic nose consisting of a 14-sensor array; the sensor response characteristics are shown in Table 3. The samples were analyzed using the electronic nose. 5g of each sample from Example 1 and Comparative Example 1 were weighed and placed in headspace vials, then equilibrated at room temperature for 30 min. The electronic nose was set to an injection time of 5 s, a washing time of 60 s, a detection time of 90 s, and a pump duty cycle of 20%. Each sample was detected in triplicate. The resulting data were processed and analyzed after the experiment.

[0159] Table 3 Performance Description of Electronic Nose Sensor

[0160]

[0161] Test results as follows Figure 3 As shown, based on a comprehensive analysis of the corresponding intensity, response dynamics, and relative response intensity of each set of sensor data, it can be seen that sensors S2, S6, S7, and S8 are highly sensitive and show significant changes, corresponding to broad-spectrum aldehydes and ketones; broad-spectrum alcohols, ethers, and acids; broad-spectrum esters and nitrogen compounds; and short-chain alkanes and alkenes, respectively.

[0162] The main comparative analysis focuses on the data from Example 1 compared to Comparative Example 1 across the four sensors. S2 corresponds to broad-spectrum aldehydes and ketones. Data shows a significant decrease in S2. Combined with GCMS detection data, it is evident that aldehydes such as heptanal, octanal, nonanal, trans-2-octenal, 2,4-heptadienal, and benzaldehyde all decreased to varying degrees. Ketones such as 2-heptanone and 2,3-octanedione also decreased to varying degrees. S6 corresponds to broad-spectrum alcohols, ethers, and acids. Combined with GCMS data on alcohols and acids, the overall trend is downward. S7 and S8 correspond to broad-spectrum esters, nitrogen compounds, and short-chain alkanes and alkenes, which generally have a smaller impact on flavor.

[0163] In summary, the gel microsphere samples provided in this application, when applied to the preparation of food raw materials such as collagen peptides, can effectively adsorb unpleasant odors and reduce the unpleasant flavors of food raw materials.

[0164] The technical features of the above embodiments can be combined in any way. For the sake of brevity, not all possible combinations of the technical features in the above embodiments are described. However, as long as there is no contradiction in the combination of these technical features, they should be considered to be within the scope of this specification.

[0165] The embodiments described above are merely illustrative of several implementations of the present invention, and while the descriptions are relatively specific and detailed, they should not be construed as limiting the scope of the invention. It should be noted that those skilled in the art can make various modifications and improvements without departing from the concept of the present invention, and these all fall within the protection scope of the present invention. Therefore, the protection scope of this invention should be determined by the appended claims, and the specification and drawings can be used to interpret the content of the claims.

Claims

1. A method for preparing β-cyclodextrin-chitosan gel microspheres, characterized in that, Includes the following steps: β-Cyclodextrin was dispersed by mixing with the first alkaline solution, chitosan was added, and then sodium trimetaphosphate aqueous solution was added to carry out a cross-linking reaction to prepare a β-cyclodextrin-chitosan cross-linked product. The β-cyclodextrin-chitosan crosslinked product was mixed with an oil solution containing a surfactant, emulsified, washed, and dried to prepare the β-cyclodextrin-chitosan gel microspheres.

2. The method for preparing β-cyclodextrin-chitosan gel microspheres according to claim 1, characterized in that, One or more of the following conditions must be met: (1) The mass-to-volume ratio of the β-cyclodextrin to the first alkaline solution is (0.5~1) g: 5 mL; (2) The first alkaline solution contains a first alkali and water, and the mass-volume ratio of the first alkali to the water is (3~8) g: 10 mL; (3) The dispersion temperature is 25℃~40℃, the dispersion time is 0.5h~1h, and the dispersion is carried out at a stirring speed of 100r / min~500r / min.

3. The method for preparing β-cyclodextrin-chitosan gel microspheres according to claim 1, characterized in that, One or both of the following conditions must be met: (1) The mass ratio of sodium trimetaphosphate to β-cyclodextrin in the sodium trimetaphosphate aqueous solution is 3:(1~3); (2) The mass-to-volume ratio of sodium trimetaphosphate to water in the sodium trimetaphosphate aqueous solution is 3g:(3~8)mL; (3) In the step of adding sodium trimetaphosphate aqueous solution, the time required for each 3g of sodium trimetaphosphate added is greater than or equal to 30min.

4. The method for preparing β-cyclodextrin-chitosan gel microspheres according to any one of claims 1 to 3, characterized in that, The mass ratio of chitosan to β-cyclodextrin is 1:(1~5).

5. The method for preparing β-cyclodextrin-chitosan gel microspheres according to any one of claims 1 to 3, characterized in that, One or both of the following conditions must be met: (1) The temperature of the cross-linking reaction is 30℃~60℃, and the time of the cross-linking reaction is 1h~3h; (2) The emulsification temperature is 50℃~80℃ and the emulsification time is 3h~6h.

6. The method for preparing β-cyclodextrin-chitosan gel microspheres according to any one of claims 1 to 3, characterized in that, One or more of the following conditions must be met: (1) The mass ratio of the chitosan to the oil solution containing the surfactant is (1~1.5):(20~40); (2) The oil solution containing surfactant includes one or two of Twine and Span, and the oil contains isopropyl myristate; optionally, the surfactant includes Twine and Span, and the mass ratio of Twine and Span is (1~3):(1~3); optionally, the mass ratio of the surfactant to the oil is 1:(20~50).

7. A β-cyclodextrin-chitosan gel microsphere, characterized in that, It is prepared by the preparation method according to any one of claims 1 to 6.

8. The application of the β-cyclodextrin-chitosan gel microspheres according to claim 7 in removing undesirable flavors from food ingredients; Optionally, the food ingredient includes at least one of animal-derived collagen tissues.

9. A method for preparing collagen peptides, characterized in that, Includes the following steps: Fish skin is soaked in a second alkaline solution, and solid-liquid separation is performed to prepare soaked fish skin. In the presence of a solvent, the soaked fish skin, alkaline protease, and the β-cyclodextrin-chitosan gel microspheres of claim 7 are mixed and subjected to enzymatic hydrolysis to inactivate the enzyme, separate the solid and liquid, collect the liquid, and prepare the collagen peptide.

10. The method for preparing collagen peptides according to claim 9, characterized in that, One or more of the following conditions must be met: (1) The second alkaline solution contains a second alkali and water, the second alkali including sodium hydroxide, and the mass ratio of the second alkali to the water is (0.5~1):(10); (2) Soaking time is (30~45) min; (3) The amount of β-cyclodextrin-chitosan gel microspheres added, based on the dry weight of fish skin, is 5wt%~10wt%; (4) The amount of alkaline protease added is 0.3wt%~0.5wt% based on the dry weight of the fish skin; (5) The mass-to-volume ratio of the fish skin to the solvent, based on the dry weight of the fish skin, is 1 g: (5~8) mL; (6) The temperature of the enzymatic hydrolysis reaction is 45℃~65℃, and the time of the enzymatic hydrolysis reaction is 3h~8h; (7) The solvent is water.

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