Preparation method and application of inclusion compound for increasing cinnamyl aldehyde embedding amount by amorphous beta-cyclodextrin recrystallization

Abstract

The invention belongs to the technical field of beta-cyclodextrin inclusion compounds, and relates to a preparation method and application of an inclusion compound for improving cinnamyl aldehyde embedding amount through amorphous beta-cyclodextrin recrystallization. The preparation method comprises the following steps: S1, preparing powdery amorphous beta-cyclodextrin: atomizing a beta-cyclodextrin aqueous solution to obtain amorphous beta-cyclodextrin; s2, uniformly mixing amorphous beta-cyclodextrin with cinnamyl aldehyde essential oil to obtain a physical mixture; and adjusting the moisture of the physical mixture, and crystallizing and drying to obtain the cinnamyl aldehyde inclusion compound. According to the cinnamyl aldehyde inclusion compound prepared by the method, the embedding effect is greatly improved, and the embedding rate and the loading rate of cinnamyl aldehyde are remarkably improved.

Description

TECHNICAL FIELD

[0001] The present application belongs to the technical field of β-cyclodextrin inclusion compound, and relates to a method for preparing an inclusion compound for improving the embedding amount of cinnamaldehyde by recrystallization of amorphous β-cyclodextrin and application thereof. BACKGROUND

[0002] Antibacterial active packaging is a packaging technology aiming to improve the quality of food storage and transportation, which inhibits the pollution and bacterial growth that may exist after food processing by introducing antibacterial active compounds or polymers with antibacterial properties into the packaging material. Among the antibacterial active compounds, essential oils (such as cinnamaldehyde) can freely diffuse to the irregular parts of the food as volatile antibacterial agents, increasing the contact area with the food and thus maximizing the antibacterial efficacy of the antibacterial agent. However, due to the poor stability of essential oils, they are prone to volatilization, which limits their practical application.

[0003] In order to solve the problem of poor stability of essential oils, the usual method is to use microencapsulation to improve the stability of essential oils to achieve the purpose of slow release. However, microencapsulation has the disadvantages of complex preparation process and inability to accurately control release, resulting in the antibacterial agent being unable to release according to the dynamic changes of the microenvironment of food storage. Cyclodextrin, as a cyclic oligosaccharide with a hydrophobic cavity, can load essential oils and has the performance of releasing essential oils in response to the increase of relative humidity in the environment; the respiration of fresh agricultural products during storage will rapidly increase the relative humidity inside the package to more than 98%, and this high humidity environment provides a unique advantage for the application of cyclodextrin. Therefore, cyclodextrin becomes an ideal carrier for embedding essential oils.

[0004] Through searching existing technologies, it is found that the current methods for preparing inclusion compounds using cyclodextrin (such as β-cyclodextrin) mainly include co-precipitation method and solid embedding method. The co-precipitation method is to first dissolve cyclodextrin (host molecule) to form a cyclodextrin solution, then add essential oil (guest molecule) to the cyclodextrin solution, stir to make the host molecule and the guest molecule fully contact, and then perform precipitation and drying operations. Due to the low solubility of the host molecule and the slow diffusion of the guest molecule, the time consumption is long, and the essential oil is prone to escape from the cavity, resulting in unsatisfactory embedding effect. Another solid embedding method is to directly add essential oil to cyclodextrin powder and stir to mix uniformly. Although this method is simple and time-saving, the essential oil molecules cannot enter the inner cavity of the cyclodextrin molecules due to the close and orderly arrangement of the crystal structure of cyclodextrin, so there is a problem of low embedding rate and loading rate. SUMMARY

[0005] In view of the technical problems of unsatisfactory embedding effect and low embedding rate and loading rate in the existing technology of embedding essential oils with cyclodextrin, the present application provides a method for preparing an inclusion compound for improving the embedding amount of cinnamaldehyde by recrystallization of amorphous β-cyclodextrin and application thereof.

[0006] The present application greatly improves the embedding effect and increases the embedding rate and loading rate of cinnamaldehyde essential oil by atomizing, adjusting moisture, and crystallizing amorphous recrystallized β-cyclodextrin, and then physically mixing the amorphous recrystallized β-cyclodextrin with cinnamaldehyde essential oil to obtain an inclusion compound.

[0007] In order to achieve the above-mentioned purpose, the technical scheme adopted by the present application is:

[0008] A preparation method of an inclusion compound for improving cinnamaldehyde embedding capacity by using amorphous β-cyclodextrin recrystallization, comprising the following steps:

[0009] S1, preparing amorphous β-cyclodextrin

[0010] Atomize the β-cyclodextrin aqueous solution to obtain powdered amorphous β-cyclodextrin;

[0011] S2, preparing a cinnamaldehyde inclusion compound

[0012] Mix the amorphous β-cyclodextrin of step S1 with cinnamaldehyde essential oil to obtain a physical mixture; adjust the moisture of the physical mixture, and then perform crystallization and drying to obtain a cinnamaldehyde inclusion compound recrystallized by amorphous β-cyclodextrin.

[0013] Further limited, in step S1, the mass concentration of the β-cyclodextrin aqueous solution is 4%-5%.

[0014] Further limited, in step S1, spray drying is used for atomization, and the inlet air temperature during spray drying is 180℃-190℃.

[0015] Further limited, in step S1, the molar ratio of amorphous β-cyclodextrin to cinnamaldehyde essential oil is 1:1.

[0016] Further limited, in step S2, the moisture content is 13%-17%; and distilled water is used to adjust the moisture.

[0017] Further limited, in step S2, the drying temperature is 45℃-50℃, and the time is 0.5h-1h.

[0018] Further limited, in step S2, the crystallization temperature is 20℃-25℃, and the crystallization time is 24h-25h.

[0019] The cinnamaldehyde inclusion compound obtained by the preparation method of the inclusion compound for improving cinnamaldehyde embedding capacity by using amorphous β-cyclodextrin recrystallization.

[0020] Application of the cinnamaldehyde inclusion compound in food packaging.

[0021] Compared with the prior art, the technical scheme adopted by the present application is:

[0022] 1、The present application can change the crystal arrangement of β-cyclodextrin molecules, expand the path of essential oil molecules into the inner cavity of β-cyclodextrin, thereby greatly improving the embedding effect, and improving the embedding rate and loading rate of cinnamaldehyde essential oil.

[0023] 2、In the preparation of the present application, by dissolving β-cyclodextrin to destroy its crystal structure, it can be brought to a disordered state, and then amorphous β-cyclodextrin is prepared by spray drying, which can ensure that the crystal structure is changed from a tight and orderly arrangement to a loose and disorderly state (see Figure 6 ), thereby reducing the hindrance of cinnamaldehyde molecules into the inner cavity; the crystal β-cyclodextrin is converted into amorphous β-cyclodextrin by spray drying method, which destroys the barrier of essential oil molecules into the inner cavity of β-cyclodextrin, and creates a kinetic advantage for molecular diffusion; by adjusting the water content, using the characteristics of amorphous β-cyclodextrin that can rebuild the crystal barrier after adding water, the cinnamaldehyde essential oil molecules are locked in the inner cavity of β-cyclodextrin. Adding a small amount of water can reduce the transition temperature of amorphous β-cyclodextrin, so that the amorphous β-cyclodextrin-cinnamaldehyde physical mixture can recrystallize at room temperature to prevent cinnamaldehyde essential oil from escaping after entering the inner cavity of β-cyclodextrin, thereby forming a β-cyclodextrin-cinnamaldehyde inclusion compound. It can be seen that the preparation method of the present application can change the crystal arrangement of β-cyclodextrin molecules, expand the path of essential oil molecules into the inner cavity of β-cyclodextrin, and improve the embedding effect.

[0024] 3、The present application found through research and testing that compared with direct physical mixing, the embedding rate, embedding efficiency and loading rate of the cinnamaldehyde inclusion compound prepared by adjusting the moisture content and crystallizing after physical mixing are increased by 39.42%, 52.04% and 4.11% respectively, and the embedding effect is much better than that of physical mixing embedding; in addition, the preparation process of the present application requires short time and simple operation, and has good storage stability. It can be seen that the preparation method of the present application effectively improves the embedding rate, loading rate and loading efficiency of cinnamaldehyde essential oil, and provides technical support for the efficient preparation of β-cyclodextrin inclusion compound and food preservation application. BRIEF DESCRIPTION OF DRAWINGS

[0025] Figure 1 Differential scanning calorimetry spectra of crystal β-cyclodextrin (crystal β-CD), amorphous β-cyclodextrin (amorphous β-CD), 13%-15% recrystallized β-cyclodextrin (Moisture content-β-cyclodextrin; MCβ-CD) prepared for examples and comparative examples;

[0026] Figure 2X-ray diffraction patterns of β-cyclodextrin, amorphous β-cyclodextrin and β-cyclodextrin-cinnamaldehyde inclusion complex prepared for comparative examples;

[0027] Figure 3 X-ray diffraction patterns of MCβ-CD and β-cyclodextrin-cinnamaldehyde inclusion complex (β-CD-IC) prepared for different examples;

[0028] Figure 4 Thermal stability curves of recrystallized β-cyclodextrin and amorphous β-cyclodextrin recrystallized cinnamaldehyde inclusion complex prepared under different example conditions;

[0029] Figure 5 Thermal stability curves of recrystallized β-cyclodextrin and amorphous β-cyclodextrin recrystallized cinnamaldehyde inclusion complex prepared under different example conditions;

[0030] Figure 6 State diagram of amorphous β-cyclodextrin before and after spray drying. DETAILED DESCRIPTION

[0031] The present application will be further described in conjunction with the accompanying drawings and examples, but the embodiments of the present application are not limited thereto. Other methods for preparing the compounds of the present application are considered to be within the scope of the present application, with some routine modifications of the reaction conditions according to the present application.

[0032] Unless otherwise defined, technical or scientific terms used in the present application shall have the same meaning as commonly understood by one of ordinary skill in the art to which the present application belongs.

[0033] Techniques, methods, and equipment known to those of ordinary skill in the relevant art can not be discussed in detail, but should be considered part of the specification where appropriate.

[0034] It should also be understood that the above-described specific examples are only used to explain the present application, and the protection scope of the present application is not limited thereto, and any person skilled in the art can make equivalent replacements or changes to the technical solutions and inventive concepts of the present application within the technical scope disclosed by the present application, which should be covered within the protection scope of the present application.

[0035] The present application provides a method for preparing an inclusion complex with improved cinnamaldehyde embedding capacity by recrystallizing amorphous β-cyclodextrin, comprising the following steps:

[0036] S1, preparing amorphous β-cyclodextrin

[0037] β-cyclodextrin was dissolved in water at 45℃ to obtain a 4%-5% (w / w) β-cyclodextrin aqueous solution. The β-cyclodextrin aqueous solution was atomized by spray drying, the inlet air temperature was 180℃, and the drying parameters were adjusted to obtain amorphous β-cyclodextrin in powder form.

[0038] S2, preparing cinnamaldehyde inclusion compound

[0039] The amorphous β-cyclodextrin prepared in step S1 was mixed with cinnamaldehyde essential oil at a molar ratio of 1:1 for 20 min to obtain a physical mixture. Distilled water was used to adjust the moisture content of the physical mixture to 13%-17% (W / W β-环糊精 ), mixed well, sealed and stored for 24 h for recrystallization, and then dried in a vacuum oven at 40℃-50℃ for 0.5h-1h to obtain a cinnamaldehyde inclusion compound.

[0040] The technical solutions provided by the present application will be described in detail below.

[0041] It should be noted that in the following examples, unless otherwise specified, the chemicals and reagents used are commercially available products commonly used in the art.

[0042] It should be noted that in the following examples, unless otherwise specified, the operations used are conventional operations; for example, unless otherwise specified, the operation temperature is room temperature operation. Unless otherwise specified, the test method is the existing standard test method in the art.

[0043] Example 1

[0044] The inclusion compound preparation method provided by the present embodiment for improving the cinnamaldehyde embedding capacity by recrystallizing amorphous β-cyclodextrin includes the following steps:

[0045] S1, preparing amorphous β-cyclodextrin

[0046] S1.1, in a 45℃ water bath stirring pot, 5g β-cyclodextrin and 120mL water were added to obtain a 4% (w / w) β-cyclodextrin aqueous solution, ensuring complete dissolution of the β-cyclodextrin.

[0047] S1.2, the β-cyclodextrin aqueous solution obtained in step S1.1 was atomized by spray drying, the inlet air temperature was 180℃, and the temperature was maintained throughout the spray drying process, the peristaltic pump flow rate was adjusted to 10r / min to obtain amorphous β-cyclodextrin in powder form; then the prepared amorphous β-cyclodextrin was packed in an aluminum bag and sealed and stored at 23±1℃ for standby.

[0048] S2, preparing cinnamaldehyde inclusion compound

[0049] S2.1, 10 g of recrystallized β-cyclodextrin was mixed with 1110 μL of cinnamaldehyde essential oil (molar ratio 1:1) using a spatula for 20 min to obtain an amorphous β-cyclodextrin-cinnamaldehyde physical mixture, referred to as a physical mixture;

[0050] S2.1, 2 g of amorphous β-cyclodextrin-cinnamaldehyde physical mixture was adjusted to a water content of 13% (W / W β-环糊精 ) using 204.14 μL of distilled water, and stirring was continued for 5 min until uniform. The uniform product was then loaded into a glass bottle, sealed and stored for 24 h for recrystallization, and dried in a vacuum oven at 45°C for 0.5 h to obtain a cinnamaldehyde inclusion complex with a water content of 13%.

[0051] Example 2

[0052] The inclusion complex preparation method provided in this example uses amorphous β-cyclodextrin recrystallization to increase the cinnamaldehyde inclusion amount, and includes the following steps:

[0053] S1, Preparation of amorphous β-cyclodextrin

[0054] This step refers to Example 1;

[0055] S2, Preparation of cinnamaldehyde inclusion complex

[0056] This step refers to Example 1, except that:

[0057] S2.2, 2 g of amorphous β-cyclodextrin-cinnamaldehyde physical mixture was adjusted to a water content of 15% (W / W β-环糊精 ) using 256.00 μL of distilled water, and stirring was continued for 5 min until uniform. The uniform product was then loaded into a glass bottle, sealed and stored for 24 h for recrystallization, and dried in a vacuum oven at 45°C for 0.5 h to obtain a cinnamaldehyde inclusion complex with a water content of 15%.

[0058] Example 3

[0059] The inclusion complex preparation method provided in this example uses amorphous β-cyclodextrin recrystallization to increase the cinnamaldehyde inclusion amount, and includes the following steps:

[0060] S1, Preparation of amorphous β-cyclodextrin

[0061] This step refers to Example 1;

[0062] S2, Preparation of cinnamaldehyde inclusion complex

[0063] This step refers to Example 1, except that:

[0064] S2.2, 310.36 μL of distilled water was used to adjust the water content of 2 g of the physical mixture of amorphous β-cyclodextrin-cinnamaldehyde to 17% (W / W β-环糊精 The uniform product was then loaded into a glass bottle, sealed and stored for 24 h for recrystallization, and then dried in a vacuum oven at 45°C for 0.5 h to obtain a cinnamaldehyde inclusion compound with a water content of 17%.

[0065] Example 4

[0066] The preparation method of the inclusion compound provided in the embodiment for improving the embedding amount of cinnamaldehyde by recrystallization of amorphous β-cyclodextrin includes the following steps:

[0067] S1, Preparation of amorphous β-cyclodextrin

[0068] This step refers to Example 1;

[0069] S2, Preparation of cinnamaldehyde inclusion compound

[0070] This step refers to Example 1, except that:

[0071] S2.2, 310.36 μL of distilled water was used to adjust the water content of 2 g of the physical mixture of amorphous β-cyclodextrin-cinnamaldehyde to 19% (W / W β-环糊精 The uniform product was then loaded into a glass bottle, sealed and stored for 24 h for recrystallization, and then dried in a vacuum oven at 45°C for 0.5 h to obtain a cinnamaldehyde inclusion compound with a water content of 19%.

[0072] Further tests were conducted on the performance of the cinnamaldehyde inclusion compound prepared in the above examples, and the following comparative examples were designed to highlight the innovative points of the preparation method of the present application.

[0073] Comparative Example 1

[0074] The difference from Example 1 is that amorphous β-cyclodextrin is directly mixed with cinnamaldehyde essential oil (without moisture adjustment and recrystallization).

[0075] S1, Preparation of amorphous β-cyclodextrin

[0076] S1.1, 5 g of β-cyclodextrin and 120 mL of water were added to a water bath stirring pot at 45°C to ensure complete dissolution of the β-cyclodextrin, obtaining a 4% (w / w) β-cyclodextrin aqueous solution.

[0077] S1.2, atomize the β-cyclodextrin aqueous solution obtained in step S1.1 by spray drying, the inlet temperature is 180℃, adjust the drying parameters to obtain amorphous β-cyclodextrin in powder form; then the prepared amorphous β-cyclodextrin is packed in an aluminum bag and stored at 23±1℃ after sealing, ready for use.

[0078] S2, preparation of cinnamaldehyde inclusion complex

[0079] S2.1, mix 10g of amorphous β-cyclodextrin with 1110μL of cinnamaldehyde essential oil using a spatula for 20min to obtain an amorphous β-cyclodextrin-cinnamaldehyde physical mixture.

[0080] S2.2, adjust the water content of 2g of the amorphous β-cyclodextrin-cinnamaldehyde physical mixture to 13%(W / W β-环糊精 ) using 204.14μL of distilled water, continue stirring for 5min until uniform. Pack the sample in a glass bottle, seal and store for 24h for recrystallization, then dry in a vacuum oven at 45℃ for 0.5h to obtain a 13% moisture content cinnamaldehyde inclusion complex.

[0081] Comparative Example 2

[0082] The difference from Example 1 is that the recrystallized β-cyclodextrin is replaced by commercially available crystalline β-cyclodextrin.

[0083] S1, mix amorphous β-cyclodextrin and cinnamaldehyde essential oil in a molar ratio of 1:1 using a spatula for 20min to obtain a β-cyclodextrin-cinnamaldehyde physical mixture.

[0084] S2, adjust the water content of 2g of the β-cyclodextrin-cinnamaldehyde physical mixture to 13%(W / W β-环糊精 ) using 204.14μL of distilled water, continue stirring for 5min until uniform. Pack the sample in a glass bottle, seal and store for 24h for recrystallization, then dry in a vacuum oven at 45℃ for 0.5h to obtain a 13% moisture content cinnamaldehyde inclusion complex.

[0085] Specifically, performance testing is carried out by crystallization kinetics detection, crystallization effect detection, embedding effect and stability.

[0086] I. Crystallization kinetics detection

[0087] The cinnamaldehyde inclusion complexes prepared in Examples 1-3 (13% MC-β-CD, 15% MC-β-CD and 17% MC-β-CD), the cinnamaldehyde inclusion complex in Comparative Example 1 (denoted as amorphous β-CD) and the cinnamaldehyde inclusion complex in Comparative Example 2 (denoted as commercially available crystalline β-CD) are tested by differential scanning calorimetry, and the test results are shown in Table 1.

[0088] Table 1 Crystallization kinetics data of recrystallized β-CD prepared under different conditions of different examples

[0089]

[0090] As can be seen from Table 1, due to the destruction of the crystalline domain, spray drying significantly reduces the crystallization enthalpy from 233.33 J / g (crystalline β-CD) to 137.33 J / g (amorphous β-CD). The subsequent moisture adjustment recrystallization gradually restores the crystallinity, and the enthalpy value proves this (184.73 J / g, 227.66 J / g and 263.85 J / g for 13% MC β-CD, 15% MC β-CD and 17% MC β-CD, respectively). This phenomenon can be attributed to water-mediated plasticization: the incorporation of water molecules lowers the glass transition temperature (Tg) of amorphous β-CD, thereby enhancing the molecular mobility at ambient temperature. This promotes molecular collisions and nucleation, ultimately promoting recrystallization.

[0091] Table 1 further shows that the moisture content accelerates the crystallization kinetics of β-CD, and the crystalline structure of β-CD plays a key role as a diffusion barrier to prevent the release of guest molecules; slow crystallization kinetics cannot establish an effective barrier, leading to premature escape of guest molecules. Therefore, by adjusting the moisture content, the crystalline structure of β-CD can be optimized, not only improving the embedding efficiency, but also enhancing the stability of the resulting inclusion complex.

[0092] II. Detection of crystallization effect

[0093] 1. Detection of crystallization effect by differential scanning calorimetry

[0094] A differential scanning calorimeter was used to detect the crystallization effect of the cinnamaldehyde inclusion complexes prepared in Examples 1-3 (13% MC-β-CD, 15% MC-β-CD and 17% MC-β-CD), the cinnamaldehyde inclusion complex in Comparative Example 1 (denoted as amorphous β-CD) and the cinnamaldehyde inclusion complex in Comparative Example 2 (denoted as crystalline β-CD).

[0095] The detection results are shown in Table 2. Figure 1 As can be seen from Table 2, with the increase of the initial moisture content, the crystallization enthalpy and crystallization rate of the recrystallized β-cyclodextrin with a moisture content of 13%, 15% and 17% also increase accordingly. The higher the crystallization enthalpy, the faster the crystallization rate, and the better the crystallization effect of the recrystallized β-cyclodextrin. The recrystallized β-cyclodextrin prepared in Example 3 with a moisture content of 17% has the best crystallization performance and can effectively prevent the escape of cinnamaldehyde essential oil from the cavity.

[0096] 2. Detection of crystallization effect by X-ray diffraction

[0097] X-ray diffractometer was used to obtain the X-ray diffraction patterns of the cinnamaldehyde inclusion compounds prepared in Examples 1-3 (13% MC-β-CD, 15% MC-β-CD and 17% MC-β-CD), the cinnamaldehyde inclusion compound in Comparative Example 1 (denoted as amorphous β-CD) and the cinnamaldehyde inclusion compound in Comparative Example 2 (denoted as crystalline β-CD), and the results are shown in Figure 2 and Figure 3 .

[0098] As can be seen from Figure 2 and Figure 3 , after spray drying, the X-ray diffraction pattern of the obtained amorphous β-CD only has two broad peaks, and the sharp peaks are completely disappeared, indicating that the β-cyclodextrin has been converted from a crystalline structure to an amorphous structure Figure 2 . In addition, the crystallinity of the recrystallized β-cyclodextrin with 13%, 15% and 17% moisture content is 29.18±3.73%, 44.70±4.44%, 75.85±2.59% respectively, which is proportional to the amount of water added Figure 3 . This indicates that the recrystallized β-cyclodextrin with 17% moisture content prepared in Example 3 has good crystallization performance and excellent embedding potential.

[0099] III. Determination of embedding rate, loading rate and embedding efficiency

[0100] The cinnamaldehyde inclusion compounds prepared in Examples 1-4 (13% MC-β-CD, 15% MC-β-CD, 17% MC-β-CD and 19% MC-β-CD) and the amorphous β-cyclodextrin recrystallization-cinnamaldehyde physical mixture (amorphous β-cyclodextrin-cinnamaldehyde physical mixture in step S2 in Example 3, denoted as PM) were tested for their embedding rate, loading rate and embedding efficiency, as shown in Table 1.

[0101] Table 1. Embedding rate, loading rate and embedding efficiency of different samples

[0102] Sample Embedding rate (%) Embedding efficiency (%) Loading rate (%) 13% MC β-CD-IC 49.17±1.43 83.80±0.55 5.13±0.15 15% MC β-CD-IC 62.20±3.30 87.96±0.62 6.49±0.34 17% MC β-CD-IC 86.44±2.15 91.35±0.22 9.01±0.22 19% MC β-CD-IC 87.64±3.60 91.30±1.43 9.16±0.34 PM 47.02±0.95 39.31±1.23 4.90±0.10

[0103] As can be seen from Table 1, with the increase of the water content of the recrystallized β-cyclodextrin, the embedding rate, the loading rate and the embedding efficiency all show a trend of obvious increase. It is shown that after the addition of water molecules, on the one hand, the water content increases the molecular mobility of the cyclodextrin molecules, thereby helping the cinnamon aldehyde essential oil to diffuse into the cavity of the β-cyclodextrin, on the other hand, it promotes the recrystallization of the amorphous β-cyclodextrin-cinnamon aldehyde physical mixture to generate a barrier to suppress the loss of the cinnamon aldehyde molecules. Therefore, the increase of the water content in the inclusion can improve the embedding rate, the loading rate and the embedding efficiency of the cinnamon aldehyde inclusion; however, when the water content is increased to 19%, the improvement of the embedding rate, the loading rate and the embedding efficiency is very small, which is close to the embedding effect of the water content of 17%. Therefore, the water content of 17% is a relatively optimal condition, and the cinnamon aldehyde inclusion prepared at this time has good embedding performance.

[0104] As can be seen from Table 1, the embedding rate, the embedding efficiency and the loading rate of the inclusion obtained after the recrystallization of the amorphous β-cyclodextrin and the physical mixture of the cinnamon aldehyde are 47.02%, 39.31% and 4.90% respectively; the embedding rate, the embedding efficiency and the loading rate of the cinnamon aldehyde inclusion obtained after the further water content adjustment and crystallization of the physical mixture in Example 3 are 86.44%, 91.35% and 9.01% respectively. Compared with the direct physical mixing, the embedding rate, the embedding efficiency and the loading rate of the cinnamon aldehyde inclusion prepared by the water content adjustment and crystallization after the physical mixing are increased by 39.42%, 52.04% and 4.11% respectively. It can be seen that the water content adjustment and crystallization can synergistically improve the embedding effect and increase the embedding rate and the loading rate of the cinnamon aldehyde essential oil.

[0105] IV. Thermal stability detection

[0106] The amorphous β-cyclodextrin in Example 3 was adjusted for water content, crystallized and dried according to the method of Example 3. Specifically, the water content of the amorphous β-cyclodextrin powder was measured by the direct drying method, and the water content was 4.12±0.11%. 2g of the amorphous β-cyclodextrin powder was taken, and distilled water was added to adjust the water content to 17% (W / W β-环糊精 ), and stirred for 5 min until uniform; then the uniform product was loaded into a glass bottle, sealed and stored for 24 h for recrystallization, and then dried in a vacuum oven at 45°C for 0.5 h to obtain recrystallized β-cyclodextrin with a water content of 17% (denoted as 17%MCβ-CD).

[0107] The stability of the recrystallized β-cyclodextrin (denoted as 17%MCβ-CD) and the cinnamon aldehyde inclusion prepared by the recrystallization of the amorphous β-cyclodextrin in Example 3 (17%MCβ-CD-IC) was tested.

[0108] The results are shown in Figure 4 and Figure 5As shown, it can be seen that the thermal stability of cinnamyl aldehyde after embedding under the conditions of Example 3 is higher than that in the state of β-cyclodextrin monomer, and has good thermal stability.

[0109] The above are several preferred embodiments of the preparation method of the present application, but cannot be taken as a limitation on the technical solutions protected by the present application. Any alternative solution obtained by ordinary technical personnel based on the technical idea of the present application without creative labor shall fall within the protection scope of the present application.

Claims

1. A method for preparing a clathrate compound with enhanced cinnamaldehyde encapsulation using amorphous β-cyclodextrin recrystallization, characterized by, It comprises the following steps: S1, preparing amorphous β-cyclodextrin Spray the β-cyclodextrin aqueous solution to obtain amorphous β-cyclodextrin powder in powder form; S2, preparing cinnamaldehyde inclusion compound Mix the amorphous β-cyclodextrin of step S1 with cinnamaldehyde essential oil to obtain a physical mixture; adjust the moisture content of the physical mixture, and then crystallize and dry to obtain the cinnamaldehyde inclusion compound, i.e. the inclusion compound.

2. The method of claim 1, wherein the method is characterized by, In step S1, the mass concentration of the β-cyclodextrin aqueous solution is 4%-5%.

3. The method of claim 1, wherein the method is characterized by, In step S1, spray drying is used for atomization, and the inlet air temperature during spray drying is 180℃-190℃.

4. The method of claim 1, wherein the method is characterized by, In step S1, the molar ratio of recrystallized β-cyclodextrin to cinnamaldehyde essential oil is 1:

1.

5. The method of claim 1, wherein the method is characterized by, In step S2, the moisture content is 13%-17%; distilled water is used to adjust the moisture content.

6. The method of preparing inclusion complex with enhanced cinnamaldehyde entrapment using recrystallization of amorphous β-cyclodextrin as claimed in claim 1, wherein, In step S2, the drying temperature is 40℃-50℃, and the time is 0.5h-1h.

7. The method of preparing inclusion complex with enhanced cinnamaldehyde entrapment using recrystallization of amorphous β-cyclodextrin as claimed in claim 1, wherein, In step S2, the crystallization temperature is 20℃-25℃, and the crystallization time is 24h-25h.

8. The cinnamaldehyde inclusion compound obtained by the preparation method of claim 1-7.

9. The use of the cinnamaldehyde inclusion compound of claim 8 in food packaging.

Images