CN114128914B - Clathrate compound, preparation method and application thereof - Google Patents
Clathrate compound, preparation method and application thereof Download PDFInfo
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- CN114128914B CN114128914B CN202111456806.8A CN202111456806A CN114128914B CN 114128914 B CN114128914 B CN 114128914B CN 202111456806 A CN202111456806 A CN 202111456806A CN 114128914 B CN114128914 B CN 114128914B
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B3/00—Preparing tobacco in the factory
- A24B3/12—Steaming, curing, or flavouring tobacco
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/281—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed
- A24B15/283—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by encapsulation of the chemical substances
- A24B15/284—Treatment of tobacco products or tobacco substitutes by chemical substances the action of the chemical substances being delayed by encapsulation of the chemical substances the additive being bound to a host by chemical, electrical or like forces, e.g. use of precursors, inclusion complexes
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/301—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by aromatic compounds
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/305—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances of undetermined constitution characterised by their preparation
Abstract
The invention discloses an inclusion compound, wherein the wall material is a mixture of dioscorea opposita polysaccharide and beta-cyclodextrin, and the core material is menthol or glycerol and propylene glycol; wherein the embedding rate of the menthol is more than 70 percent; the embedding rate of the glycerol and the propylene glycol is more than 80 percent. The invention also discloses a preparation method and application of the clathrate compound.
Description
Technical Field
The invention belongs to the technical field of preparation of an inclusion compound, and particularly relates to an inclusion compound, a preparation method and application thereof.
Background
The inclusion technique refers to a biological technique of forming an inclusion compound by one molecule being occluded in a cavity structure of another molecule, and is commonly used in the field of Chinese medicinal preparations for improving the stability, the solubility and the bioavailability of medicaments, and the like. Beta-cyclodextrin (beta-CD) is a cylindrical compound formed by connecting a plurality of glucose molecules with each other by alpha-1,4 glycosidic bonds, is a nontoxic and tasteless powdery substance, and can form an inclusion compound with organic molecules, inorganic ions, complexes and even inert gases because the outer side of a cavity contains hydrophilic groups and the inner side contains hydrophobic groups, so that the included substance is prevented from being influenced by light, heat and oxidation. Therefore, cyclodextrin is often used as a molecular microcapsule material, and is increasingly widely applied in the fields of food, medicine and the like.
Menthol is a colorless needle crystal, slightly soluble in water, and widely used in the fields of foods, cosmetics, and pharmaceuticals because of its cooling activity, but menthol is easily sublimed and unstable in light and heat. Glycerol, also known as glycerol, is a simple polyol, a colorless, sweet, non-toxic viscous liquid with high solubility and moisture retention due to its three hydroxyl groups. Propylene glycol is a viscous colorless liquid, miscible with many solvents, glycerin and propylene glycol are the main components of the electronic cigarette, glycerin is used for heating the atomizer to generate aerosol, and propylene glycol is atomized to form smoke, so as to deliver nicotine to users. Beta-cyclodextrin (beta-CD) is an ideal inclusion material, and the stability of the inclusion material can be improved after the beta-CD is adopted to include menthol or glycerol and propylene glycol, so that the inclusion compound and the application are more reported.
However, the inclusion rate of the inclusion compound obtained by taking beta-cyclodextrin as a wall material and using menthol or glycerol and propylene glycol as a core material is still relatively low, for example, the inclusion rate of menthol is difficult to exceed 50%, and the inclusion rate of glycerol and propylene glycol is difficult to exceed 70%. The present invention has been made to solve the above problems.
Disclosure of Invention
The invention provides an inclusion compound of two alcohols, a preparation method and application thereof based on the problems, wherein the preparation method is simple and easy to operate and can be used for large-scale production.
The preparation method of the two alcohol inclusion compounds comprises the following steps:
the technical scheme of the invention is as follows:
the first aspect of the invention discloses an inclusion compound, the wall material of which is a mixture of dioscorea opposita polysaccharides and beta-cyclodextrin, and the core material of which is menthol or glycerol and propylene glycol; wherein the embedding rate of the menthol is more than 70 percent; the embedding rate of the glycerol and the propylene glycol is more than 80 percent.
Preferably, the embedding rate of the menthol is 70.69%; the embedding rate of the glycerol and the propylene glycol is 80.58%.
Preferably, the menthol inclusion compound has a moisture content of 4.7wt% and a solubility of 44.67%; the water content of the glycerin and propylene glycol inclusion compound is 5.3wt%; the solubility was 68.14%.
Preferably, the dioscorea opposita polysaccharide is 1-10wt% of the weight of the wall material beta-cyclodextrin and the dioscorea opposita polysaccharide.
The second aspect of the invention discloses a preparation method of the beta-cyclodextrin inclusion compound, which comprises the following steps:
(1) dissolving Chinese yam polysaccharide and beta-cyclodextrin in a certain proportion at a certain temperature to prepare a saturated solution of Chinese yam polysaccharide and beta-cyclodextrin;
(2) dissolving menthol or glycerol and propylene glycol in absolute ethyl alcohol to form a solution, then slowly dripping the solution into the saturated solution of the dioscorea opposita polysaccharide and the beta-cyclodextrin in the step (1), and mixing at constant temperature;
(3) and (3) cooling the mixed solution obtained in the step (2) to room temperature, standing in a low-temperature environment, and then separating and drying to obtain the clathrate compound.
Preferably, the temperature of step (1) is 50-80 ℃.
Preferably, the temperature of the step (2) is 40-60 ℃, and the mixing time is 1-4h; the mixing is stirring, and the stirring speed is 400-700r/min.
Preferably, the standing temperature in the step (3) is 0-8 ℃ and the drying temperature is 40-60 ℃.
Preferably, the preparation method of the dioscorea opposita polysaccharide comprises the following steps: pulverizing rhizoma Dioscoreae into powder, dissolving with water, filtering, and collecting clear liquid; adding ethanol to precipitate rhizoma Dioscoreae polysaccharide, centrifuging, filtering, and freeze drying the solid phase to obtain the rhizoma Dioscoreae polysaccharide.
In a third aspect of the invention, the application of the inclusion compound in tobacco is disclosed.
The invention has the beneficial effects that:
1. the embedding rate of two alcohols of the two-alcohol inclusion compound is obviously improved. Wherein the embedding rate of the menthol can reach 70.69%; the embedding rate of the glycerol and the propylene glycol can reach 80.58 percent. The embedding rate of menthol in the prior art is difficult to exceed 50 percent, and the embedding rate of glycerol and propylene glycol is difficult to exceed 70 percent.
2. According to the preparation method of the clathrate compound, a small amount of dioscorea opposita polysaccharide is added as a wall material, so that the embedding rate of the obtained two alcohol clathrate compounds is obviously improved, and the clathrate compound is high in solubility and low in moisture content. The application of the compound in food, medicine and tobacco is expanded.
3. The preparation method is simple, and the preparation method of the dioscorea opposita polysaccharide is simple.
Drawings
FIG. 1 is an infrared spectrum of a menthol clathrate (top) and a clathrate (bottom) of glycerin and propylene glycol obtained in example 1.
FIG. 2 is a scanning electron micrograph of the menthol clathrate and the glycerin-propylene glycol clathrate obtained in example 1. The upper is wall material beta-cyclodextrin powder; the middle is menthol inclusion compound; the following is a propylene glycol and glycerol inclusion compound.
Fig. 3 shows thermogravimetric curves of the menthol inclusion compound (upper) and the glycerin and propylene glycol inclusion compound (lower) obtained in example 1.
Fig. 4 is a graph showing the release in air of the menthol inclusion compound (upper) and the inclusion compound of glycerin and propylene glycol (lower) obtained in example 1.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail by examples and experimental data below. The specific embodiments described herein are merely illustrative of the invention and do not delimit the invention.
Example 1: the preparation of two kinds of inclusion compounds comprises the following steps:
1. fully dissolving 5wt% of dioscorea opposita polysaccharide and beta-cyclodextrin in deionized water at 70 ℃ to prepare saturated solution;
2. dissolving menthol or glycerol-propylene glycol in a small amount of absolute ethyl alcohol, slowly dripping the menthol or glycerol-propylene glycol solution into a saturated solution of beta-cyclodextrin, and stirring for 2 hours at a constant temperature of 50 ℃ and 500 r/min;
3. cooling to room temperature, standing at 4 deg.C for 24 hr, vacuum filtering, and drying at 50 deg.C to obtain two white powdered clathrate compounds.
Example 2: embedding rate analysis of two inclusion compounds
Two kinds of clathrates (W) were obtained by collecting 1g of each of the clathrates of example 1 1 ) Adding into a small dry beaker, adding 20mL of hot water, stirring to dissolve completely, and then adding 10mL of absolute ethyl alcohol, 10mL of absolute ethyl ether and 10mL of petroleum ether in sequence to extract menthol or glycerol-propylene glycol. The extraction was repeated twice, the combined extracts transferred to a beaker of constant weight (W) 2 ) Evaporating the solvent to constant weight to obtain purified clathrate (W) 3 ). According to the formula
And calculating the embedding rate. The results were: the embedding rate of menthol is 70.69%, the embedding rate of glycerol-propylene glycol is 87.58%, the embedding effect is ideal, and the embedding rate is improved by about 20% compared with that of a beta-CD single-wall material inclusion compound.
Example 3: water content analysis of two clathrates
10g (m) of the two clathrates obtained in example 1 were weighed out separately and dried in an oven at 105 ℃ for 2 hours, and then cooled to room temperature in a drierWarm, weighing m 1 Repeating the above operation for 1h, and weighing to m 2 The difference between the two is not more than 0.05g;
the results were: the water content of the menthol inclusion compound was 4.7%, and the water content of the glycerin-propylene glycol inclusion compound was 5.3%. The water content of the two inclusion compounds is about 5%. Therefore, the storage stability is not easy to mildew, absorb moisture and agglomerate in the storage process.
Example 4: solubility analysis of the two Inclusions
Respectively weighing 5.0g (w) of the two inclusion compounds obtained in the example 1 into a 50mL centrifuge tube, adding a proper amount of water with the temperature of 25-30 ℃, plugging, fully shaking for dissolving for 5min, placing the centrifuge tube into a centrifuge, centrifuging the centrifuge tube at the rotating speed of 1000rmp for 10min, pouring off the supernatant, adding a proper amount of water with the temperature of 25-30 ℃ into the centrifuge tube, fully shaking for 5min, centrifuging the centrifuge tube for 10min, then pouring off the supernatant, repeating the step until the precipitate is not dissolved, and washing the precipitate into a weight with a small amount of water (w) with known mass (w 1 ) Drying in boiling water, transferring into 105 deg.C oven, and drying to constant weight (w) 2 ). The calculation formula is as follows:
the results were: the solubility of the menthol inclusion compound is 44.67%, and the solubility of the glycerol-propylene glycol inclusion compound is 68.14%. Thus, the solubility of the encapsulated menthol is improved.
Example 5: infrared analysis of two clathrates
Respectively tabletting menthol, glycerol-propylene glycol, beta-cyclodextrin and two inclusion compounds by using potassium bromide at the concentration of 500-4500 cm -1 And (4) performing infrared spectrum measurement. The results are shown in FIG. 1.
As can be seen from fig. 1, the infrared spectra of the menthol-beta-CD clathrate and beta-CD are very similar, and the peak positions are approximately the same. The beta-CD is 3402.3cm -1 An absorption peak appears, which corresponds to a stretching vibration peak of-OH on a glucose ring. The stretching vibration peak of-OH in the menthol-beta-CD generates red shift, and the peak position is 3390.7cm -1 . Menthol is at 2922.0cm -1 The absorption peak appears corresponding to-CH 3 And in the beta-CD and menthol beta-CD inclusion compound, the intensity of the vibration peak is obviously weakened. The bending vibration of the O-H bond of the beta-CD is also 1651.0cm -1 Bathochromic shift to 1639.4cm after clathration -1 . From this, it is presumed that menthol and β -CD have undergone an inclusion reaction. In general, the infrared characteristic absorption peaks of menthol- β -CD and β -CD vary little, primarily by the mechanism of inclusion, generally speaking, the proportion of guest molecules in the inclusion complex is usually not more than 25%, and are included in the hydrophobic cavity, so that the characteristic peak of the guest molecule is masked and not easily recognized by the characteristic peak of the host molecule β -CD itself. Similarly, there are similar cases in glycerol-propylene glycol, β -CD and β -CD clathrates, and the relevant parameters are shown in FIG. 1.
Example 6: surface structures of two clathrates
The surface structure of the inclusion compound was observed by a Scanning Electron Microscope (SEM). Fixing the dried inclusion compound on a metal short rod with a double-sided adhesive tape to uniformly distribute sample powder, spraying gold, and observing under the magnification of 1000 times. The results are shown in FIG. 2.
The morphological structure difference between the wall material beta-CD and the inclusion compound is observed through a scanning electron microscope, as shown in figure 2, the shapes and the sizes of the wall material and the two inclusion compounds are obviously different, wherein the surface of the wall material beta-CD is rough, the edge of the wall material beta-CD is irregular, and the surfaces of the two inclusion compounds are smooth, and the edge of the two inclusion compounds is relatively flat. The shape and size difference between the beta-cyclodextrin and the inclusion compound shows that the core material and the wall material beta-CD form a new stable inclusion state, and the embedding effect is ideal.
Example 7: thermal stability analysis of the two clathrates
And (3) carrying out thermal stability analysis on the menthol, the menthol inclusion compound, the glycerol-propylene glycol inclusion compound and the mixture of the dioscorea opposita polysaccharide and the beta-cyclodextrin by adopting a comprehensive thermal analyzer. Weighing a proper amount of the inclusion compound, placing the inclusion compound in a sample cell of an instrument, wherein the atmosphere is nitrogen, and the flow is as follows: 20cm 3 At a temperature rise rate of 10 ℃/minThermogravimetric analysis was performed at a temperature ranging from room temperature to 800 ℃. The results are shown in FIG. 3.
The thermogravimetric analysis curve of the inclusion compound is shown in fig. 3, and as can be seen from fig. 3, the thermal weight loss process of menthol is mainly 30-160 ℃, the mass loss is close to 100%, mainly caused by violent volatilization, and the weight loss process of beta-CD is divided into several stages: the residual moisture is volatilized at the temperature of 30-110 ℃, the mass loss is 15 percent, the temperature is between 110-290 ℃, the mass loss is only 1.3 percent in a stable region, and the decomposition weight loss is 80 percent when the temperature is 300 ℃. The thermal weight loss process of the menthol inclusion compound has the following stages: the volatilization weight loss of free moisture and a small amount of menthol is 8 percent at the temperature of between 30 and 90 ℃; the quality is slowly reduced at 90-290 ℃, the mass loss is 5.2 percent mainly caused by slow volatilization of menthol from a beta-CD cavity, the mass loss is 5.2 percent at 300-700 ℃, the decomposition weight loss of the wall material is mainly caused, the maximum decomposition temperature is 350 ℃, and the mass loss is 83 percent. It can be seen that the thermal stability of the inclusion compound is significantly improved compared to that of core material menthol. Similarly, similar behavior is observed in the inclusion system of glycerol-propylene glycol.
Example 8: release rule of two inclusion compounds in air
Respectively weighing 1.1g of the dried menthol inclusion compound, the mixture of the menthol and the dioscorea opposita polysaccharide and the beta-cyclodextrin, and the mixture of the glycerol-propylene glycol inclusion compound, the glycerol-propylene glycol, the dioscorea opposita polysaccharide and the beta-cyclodextrin, respectively, placing the mixture in an oven at 30 ℃,50 ℃ and 70 ℃, respectively, measuring the residual mass of the sample at intervals, and observing the release rule of the inclusion compound in the air, wherein the result is shown in figure 4.
As can be seen from fig. 4, the release rates of the inclusion compound in the air are different under different temperature conditions, the release rate of the menthol inclusion compound is increased with the increase of the temperature, the release rate is gradually gentle with the increase of the time, the release rule of the glycerin-propylene glycol inclusion compound is not greatly different at 30 ℃ and 50 ℃, the release rate is obviously increased at 70 ℃, and the quality of the inclusion compound is slightly increased at 30 ℃ due to the use of the glycerin-propylene glycol with higher proportion and high hygroscopicity as the core material, probably because the substitution of the object and the water molecule in the inclusion compound occurs. Because the embedding and releasing need the participation of moisture, the moisture content in the environment has certain influence on the release of the core material in the inclusion compound.
Example 8: application of two inclusion compounds in electronic cigarette
Preparation of two clathrate tobacco liquids: respectively preparing the two inclusion compounds into electronic cigarette liquid; the control smoke solution is menthol, glycerol and propylene glycol, and the proportion of the control smoke solution is the same as that of the clathrate smoke solution. The prepared clathrate compound tobacco juice and the control juice were added to the cartridges of electronic cigarettes, respectively, in the same amounts, and subjected to sensory evaluation by a panel.
The evaluation finds that the sensory quality of the two clathrate compound tobacco liquids is better than that of a control tobacco liquid, the aroma of the clathrate compound tobacco liquid is better, and the specific expression is that the aroma of the clathrate compound tobacco liquid is longer and the uniformity of single-mouth smoking is better.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (6)
1. The preparation method of the inclusion compound is characterized in that the wall material of the inclusion compound is a mixture of dioscorea opposita polysaccharide and beta-cyclodextrin, and the core material of the inclusion compound is menthol; wherein the embedding rate of the menthol is more than 70 percent; the Chinese yam polysaccharide is 1-10wt% of the wall material beta-cyclodextrin and the Chinese yam polysaccharide; the menthol clathrate had a moisture content of 4.7wt% and a solubility of 44.67%;
the preparation method of the clathrate compound comprises the following steps:
(1) dissolving Chinese yam polysaccharide and beta-cyclodextrin in water at a certain temperature according to a certain proportion to prepare a saturated solution of Chinese yam polysaccharide and beta-cyclodextrin;
(2) dissolving menthol in absolute ethanol to form a solution, then slowly dropwise adding the solution into the saturated solution of the dioscorea opposita polysaccharide and the beta-cyclodextrin in the step (1), and mixing at constant temperature;
(3) and (3) cooling the mixed solution obtained in the step (2) to room temperature, standing in a low-temperature environment, and then separating and drying to obtain the clathrate compound.
2. The method according to claim 1, wherein the temperature in the step (1) is 50 to 80 ℃.
3. The method according to claim 1, wherein the temperature in step (2) is 40-60 ℃ and the mixing time is 1-4h; the mixing is stirring at a speed of 400-700r/min.
4. The production method according to claim 1, wherein the temperature of the standing in the step (3) is 0 to 8 ℃ and the temperature of the drying is 40 to 60 ℃.
5. The preparation method of claim 1, wherein the dioscorea opposita polysaccharide is prepared by the following steps: pulverizing rhizoma Dioscoreae into powder, dissolving with water, filtering, and collecting clear liquid; adding ethanol to precipitate rhizoma Dioscoreae polysaccharide, centrifuging, filtering, and freeze drying the solid phase to obtain the rhizoma Dioscoreae polysaccharide.
6. Use of the inclusion compound prepared by the preparation method according to any one of claims 1 to 5 in tobacco.
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