A cigarette paper containing cinnamic alcohol-beta-d-glucopyranoside and a preparation method thereof
The synthesis of cinnamyl alcohol-β-D-glucopyranoside via Au-Ag nanocluster catalyst and its addition to cigarette paper solves the problems of easy oxidation and volatilization of cinnamyl alcohol and high synthesis cost of existing glycosides, achieving stable aroma release and high-end aroma texture of spicy-sweet cigarette paper.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- CHINA TOBACCO ANHUI IND CO LTD
- Filing Date
- 2024-05-29
- Publication Date
- 2026-05-19
AI Technical Summary
Cinnamyl alcohol, as a flavoring agent for tobacco, is easily oxidized and volatilized. When directly added to cigarette paper, its aroma is unstable. Existing glycoside synthesis methods are costly and cumbersome, making it difficult to achieve a stable release of spicy and sweet aroma substances.
Cinnamyl alcohol-β-D-glucopyranoside was synthesized by reacting cinnamyl alcohol with α-bromotetraacetyl glucose using Au-Ag nanocluster catalyst, and then added to cigarette paper. Spicy and sweet flavored cigarette paper was prepared by gravure coating technology.
This study achieved the stable release of a spicy and sweet aroma from cinnamyl alcohol-β-D-glucopyranoside during cigarette combustion, reducing production costs and improving the stability and consistency of the aroma, thus enhancing the flavor and texture of cigarettes.
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Figure CN118910924B_ABST
Abstract
Description
Technical Field
[0001] This invention belongs to the field of tobacco materials and flavoring preparation, specifically relating to a method for preparing a sweet and spicy cigarette paper containing cinnamyl alcohol-β-D-glucopyranoside, and a new method for synthesizing cinnamyl alcohol-β-D-glucopyranoside. Background Technology
[0002] Cigarette paper is an essential auxiliary material in the cigarette manufacturing process, used to wrap shredded tobacco to make cigarettes, which burn together with the tobacco during smoking. Therefore, in addition to flavoring the tobacco, flavoring the cigarette paper is one of the effective means of enhancing the aroma of cigarettes.
[0003] Cinnamyl alcohol is a commonly used flavoring agent in cigarettes. Adding it to cigarettes enriches the aroma, enhances the flavor profile, and produces a smoother, less irritating smoke. However, because cinnamyl alcohol is a terpene alcohol, it is chemically unstable and easily oxidized and volatilized when exposed to air after being added directly to cigarette paper. Glycoside flavorings, on the other hand, are inherently volatile and chemically stable, lacking specific aroma characteristics. However, when cigarettes are burned, they undergo decomposition, releasing the desired aroma compounds. Furthermore, the amount of aroma released remains consistent throughout the smoking process, achieving a stable aroma compensation effect.
[0004] Glycosides can be synthesized using methods such as the Fischer method, the Koenigs-Knorr method, phase-transfer catalysis, the Schmidt method, and the Helferich method. The most commonly used method is the Koenigs-Knorr method, which involves reacting fully acetylated glucose with hydrobromic acid to obtain α-acetyl bromide. Under the action of a silver salt catalyst, β-glycosides are readily obtained by attacking the anomeric carbon with other nucleophiles such as alcohols, amines, and thiols. Researchers have used this method to synthesize various monosaccharide and disaccharide glycosides, such as geraniol-β-D-glucopyranoside and geraniol-β-D-glucopyranoside. However, this method uses a large amount of precious silver salt as a catalyst, and silver salt is prone to deactivation, resulting in high cost and a cumbersome preparation process. Inspired by the excellent performance of silver-based catalysts in glycoside synthesis and the multi-site synergistic catalysis of metal clusters, this invention designs and develops atomically precise gold-silver nanocluster catalysts for efficient glycoside synthesis. Summary of the Invention
[0005] The purpose of this invention is to provide a sweet and spicy cigarette paper containing cinnamyl alcohol-β-D-glucopyranoside, aiming to provide a novel cigarette paper that can stably release the sweet and spicy substance cinnamyl alcohol during smoking.
[0006] The second objective of this invention is to design and develop a novel Au-Ag nanoclusters as a catalyst for glycosylation reactions, and to provide an efficient method for the synthesis of cinnamyl alcohol-β-D-glucopyranoside compounds. The catalyst is easy to recover, can be reused, and can reduce production costs.
[0007] The third objective of this invention is to conduct the first systematic study on the thermal stability and thermal decomposition products of cinnamyl alcohol-β-D-glucopyranoside, as well as their transfer behavior in cigarettes, providing basic data support for the application of this monomeric flavoring in cigarettes.
[0008] To achieve its objectives, the present invention employs the following technical solution:
[0009] This invention provides a sweet and spicy cigarette paper containing cinnamyl alcohol-β-D-glucopyranoside compound with the following general structural formula:
[0010]
[0011] The present invention also provides a method for synthesizing the cinnamyl alcohol-β-D-glucopyranoside compound, the reaction formula of which is shown below:
[0012]
[0013] The synthesis method includes the following steps:
[0014] Step 1: Add α-bromotetraacetyl glucose (Structure I), cinnamyl alcohol (Structure II), base, and first solvent sequentially to a round-bottom flask. Under stirring, slowly add Au-Ag nanoclusters as catalyst and react at 20-50℃ for 3-8 hours. After the reaction is complete, filter the mixture. Wash the filter residue several times with water and ethanol, dry it, and reuse it. Wash the reaction solution twice with water. Combine the aqueous phases and extract with dichloromethane. Dry the organic phase (the organic phase after combining the water-washed reaction solution and the extracted dichloromethane) with anhydrous sodium sulfate, filter it, and evaporate it under reduced pressure. Separate the intermediate product (Structure III) by silica gel column chromatography.
[0015] Step 2: Add the base and second solvent directly to intermediate III obtained in Step 1, and react at 20-50℃ for 1-4 hours. After the reaction is complete, neutralize to neutral with hydrochloric acid solution. Wash the reaction solution twice with water, combine the aqueous phases and extract with dichloromethane. Dry the organic phase with anhydrous sodium sulfate, filter, remove the organic solvent by rotary evaporation under reduced pressure, and separate by silica gel column chromatography to obtain cinnamyl alcohol-β-D-glucopyranoside.
[0016] Furthermore, the structural formula of the Au-Ag nanoclusters is [Au9Ag4(Dppp)4Cl4]. + Cl -The preparation method is as follows: 1,3-bis(diphenylphosphine)propane (abbreviated as Dppp) is added to a mixed solution of chloroauric acid tetrahydrate in ethanol and dichloromethane, and stirring is continued for 30 minutes. An ethanol solution of silver nitrate is added to the above reaction system, and stirring is maintained. Subsequently, an ethanol solution of sodium borohydride is added to the reaction system, and the mixture is aged for 3 hours. Then, concentrated hydrochloric acid is added dropwise, and after etching for 1 to 2 days, the supernatant is obtained by centrifugation. After concentration, the supernatant is washed with water and diethyl ether to obtain a solid powder. The obtained solid powder is dissolved in dichloromethane, separated by thin-layer chromatography, and the concentrated solid is precipitated as pure Au-Ag cluster crystals in a dichloromethane / n-pentane system at 4°C for two to three weeks.
[0017] Further, in step 1: the alkali is at least one of potassium hydroxide, sodium hydroxide, potassium carbonate, DBU, pyridine, and triethylamine, preferably potassium carbonate; the first solvent is at least one of tetrahydrofuran, dioxane, dichloromethane, toluene, ethyl acetate, dimethyl sulfoxide, and petroleum ether, preferably dichloromethane; the heating temperature is 20-50℃, and the reaction time is 3-8h, preferably 25℃ for 4 hours; the eluent used for silica gel column chromatography is composed of petroleum ether and ethyl acetate in a volume ratio of 1-10:1, preferably 3:1.
[0018] Further, in step 1, the molar ratio of α-bromotetraacetyl glucose I, cinnamyl alcohol II, base, and catalyst is 1:1-1.5:1.1-2:0.005-0.1, preferably 1:1.1:1.2:0.01.
[0019] Further, in step 2: the alkali is at least one selected from sodium methoxide, sodium hydroxide, potassium carbonate, pyridine, and triethylamine, preferably sodium methoxide; the second solvent is at least one selected from methanol, ethanol, tetrahydrofuran, dioxane, and dimethyl sulfoxide, preferably methanol; the heating temperature is 20-50℃, and the reaction time is 1-4 hours, preferably 25℃ for 2 hours. The eluent used for silica gel column chromatography is composed of dichloromethane and methanol in a volume ratio of 1-10:1, preferably 5:1.
[0020] Furthermore, in step 2, the molar ratio of intermediate product III to base is 1:0.2-1, preferably 1:0.25.
[0021] Furthermore, in the preparation of Au-Ag nanoclusters, the molar ratio of chloroauric acid tetrahydrate, 1,3-bis(diphenylphosphine)propane, silver nitrate, and sodium borohydride is 1:0.8-1.2:0.5-1:0.8-1.2, preferably 1:1:0.7:1.
[0022] This invention also provides a method for preparing a sweet and spicy cigarette paper containing cinnamyl alcohol-β-D-glucopyranoside: cinnamyl alcohol-β-D-glucopyranoside is dissolved in an alcohol-water mixed solvent to obtain a coating solution; the coating solution is coated onto the inner surface of the cigarette paper using a gravure coating method, and after hot air drying, the sweet and spicy cigarette paper containing cinnamyl alcohol-β-D-glucopyranoside is obtained.
[0023] Furthermore, the amount of cinnamyl alcohol-β-D-glucopyranoside added is 0.0001%-0.01% of the weight of cigarette paper, preferably 0.001%.
[0024] Furthermore, the alcohol-water mixed solvent is ethanol / water or propylene glycol / water, preferably ethanol / water (volume ratio of 1 / 9).
[0025] Furthermore: the coating machine speed is controlled at 80-120m / min, preferably 100m / min; the drying temperature is controlled at 50-90℃, preferably 70℃.
[0026] The spicy-sweet aroma cigarette paper prepared by this invention has no aroma at room temperature, but releases spicy and sweet aromas during cigarette combustion. It is suitable for various types of cigarettes, such as traditional cigarettes or heated tobacco products.
[0027] The beneficial effects of this invention are reflected in:
[0028] 1. This invention prepares a spicy-sweet aroma cigarette paper. Compared with blank cigarettes, the cigarette paper containing cinnamyl alcohol-β-D-glucopyranoside has a more upscale aroma, a more delicate and mellow smoke, and the spicy and sweet aroma is more stable during the smoking process, with better consistency of aroma before and after smoking.
[0029] 2. This invention develops atomically precise Au-Ag nanocluster catalysts for the efficient synthesis of glycosides. After the reaction, the clusters can be precipitated by adding a poor solvent (n-hexane or petroleum ether), which not only facilitates product purification but also makes the catalyst easy to recover, saving costs.
[0030] 3. This invention is the first to study the thermal behavior of cinnamyl alcohol-β-D-glucopyranoside flavoring. The results show that compared with cinnamyl alcohol, cinnamyl alcohol-β-D-glucopyranoside has significantly improved thermal stability. The thermal decomposition temperature increased from 76.3℃ to 194.5℃, and the maximum thermal weight loss temperature increased from 204.7℃ to 313.2℃. That is, cinnamyl alcohol-β-D-glucopyranoside has a more stable structure and is not easily oxidized and deteriorated. Attached Figure Description
[0031] Figure 1 XPS and ESI-MS spectra of Au-Ag nanoclusters.
[0032] Figure 2 This is an analytical diagram of the single-crystal structure of Au-Ag nanoclusters.
[0033] Figure 3 The figures show the stability test results of Au-Ag nanoclusters in different solvents. The left figure shows the initial state of Au-Ag nanoclusters in different solvents and after one week of storage. The right figure shows the absorption spectrum of Au-Ag nanoclusters in ethanol over time.
[0034] Figure 4 Cinnamyl alcohol-β-D-glucopyranoside 1 H NMR spectrum.
[0035] Figure 5 Cinnamyl alcohol-β-D-glucopyranoside 13 C10 NMR spectrum.
[0036] Figure 6 This is the high-resolution mass spectrum of cinnamyl alcohol-β-D-glucopyranoside.
[0037] Figure 7 The thermogravimetric analysis (TG-DTG) curves of cinnamyl alcohol and cinnamyl alcohol-β-D-glucopyranoside are shown, where (a) is the TG curve and (b) is the DTG curve.
[0038] Figure 8 This is the GC spectrum of the thermal decomposition product of cinnamyl alcohol-β-D-glucopyranoside at 300℃. Detailed Implementation
[0039] To make the above-mentioned objects, features, and advantages of the present invention more apparent and understandable, the specific embodiments of the present invention will be described in detail below with reference to the accompanying drawings and examples. The following content is merely illustrative and explanatory of the concept of the present invention. Those skilled in the art can make various modifications or additions to the described specific embodiments or use similar methods to replace them, as long as they do not deviate from the inventive concept or exceed the scope defined by the claims, all of which should fall within the protection scope of the present invention.
[0040] Example 1: Au-Ag nanoclusters ([Au9Ag4(Dppp)4Cl4]) + Cl - Catalyst preparation
[0041] Chloroauric acid tetrahydrate (40 mg, 0.1 mmol) was dissolved in a mixture of 5 mL ethanol and 10 mL dichloromethane and stirred uniformly for 30 minutes. Then, 1,3-bis(diphenylphosphine)propane (Dppp, 42 mg, 0.1 mmol) was added to the reaction system and stirring continued for another 30 minutes. Silver nitrate (12 mg, 0.07 mmol) was dissolved in 2 mL ethanol and added to the reaction system; the solution gradually changed from pale yellow to milky white, and stirring continued for 1 hour. Sodium borohydride (4 mg, 0.1 mmol) was dissolved in 2 mL ethanol and added rapidly in one go; the reaction solution gradually turned black. After aging for 3 hours, 0.5 mL concentrated hydrochloric acid was added dropwise to the reaction system. After etching for 1 to 2 days, the precipitate was removed by centrifugation. The supernatant was concentrated and washed several times with water and ether to obtain a solid powder. This solid powder was dissolved in 5 mL dichloromethane and separated by thin-layer chromatography (developing solvent V). 二氯甲烷 V 甲醇 The ratio of the two groups is 20:1. The least polar bands are collected, concentrated, and then dissolved in a small amount of dichloromethane. The mixture is then precipitated with n-hexane. The resulting solid precipitates pure cluster crystals in a dichloromethane / n-pentane system at 4°C for two to three weeks, thus obtaining the Au-Ag nanocluster catalyst.
[0042] Figure 1 XPS (a) and ESI-MS spectra (b) of Au-Ag nanoclusters, from Figure 1 In a, it can be clearly seen that the metal core of the nanoclusters includes two metals, Au and Ag, and its peripheral ligands are mainly composed of phosphine and chlorine. Figure 1 A single mass spectrum peak can be observed in b, which is assigned to [Au9Ag4(Dppp)4Cl4]. + The molecular ion peaks indicate the precise composition of the clusters.
[0043] Figure 2 The image shows the analytical structure of a single crystal Au-Ag nanoclusters. In the image: yellow - Au; red - Ag; green - Cl; pink - P; gray - C, H. The left image shows the precise structure of a single Au-Ag nanocluster molecule, and the right image shows the distribution of four nanocluster molecules within a single Au-Ag nanocluster unit cell.
[0044] Figure 3This image shows the stability test results of Au-Ag nanoclusters in different solvents. 5.0 mg of Au-Ag nanoclusters were dissolved in 5.0 mL of ethanol, acetonitrile, dichloromethane, and chloroform, respectively. Absorption spectra of the four nanocluster solutions were obtained using a UV-Vis-NIR spectrophotometer. The absorption spectra of the nanocluster solutions were then measured at 30 minutes, 1 hour, 5 hours, 12 hours, 1 day, 3 days, 5 days, and 7 days. The stability of the Au-Ag nanoclusters in the solvents was determined by the characteristic absorption of the spectra. The absorption spectrum of the cluster in ethanol over time is shown below. Figure 3 As shown on the right. This spectrum demonstrates that the Au-Ag nanoclusters maintain extremely high stability in the dissolved state, with their absorption spectrum remaining unchanged for 7 days.
[0045] Example 2: Synthesis of Cinnamyl alcohol-β-D-glucopyranoside
[0046] A method for synthesizing cinnamyl alcohol-β-D-glucopyranoside, comprising the following steps:
[0047] Step 1: In a 250 mL round-bottom flask, α-bromotetraacetyl glucose (4.10 g, 10 mmol), cinnamyl alcohol (1.48 g, 11 mmol), K₂CO₃ (1.66 g, 12 mmol), and 100 mL of dichloromethane were added sequentially as solvent. Au-Ag nanoclusters (4.03 g, 0.1 mmol) were slowly added under stirring. The reaction was carried out at 25 °C for 4 h. After filtration, the residue was washed three times with 20 mL of water and ethanol, and then air-dried to obtain cluster crystals, which were the Au-Ag nanocluster catalyst. The resulting reaction solution was washed twice with water, and the aqueous phases were combined and extracted with dichloromethane. The organic phase was dried over anhydrous sodium sulfate, filtered, and then separated by rotary evaporation under reduced pressure. Separation was performed by silica gel column chromatography (eluent V). 石油醚 V 乙酸乙酯 The ratio was 3:1, yielding cinnamyl alcohol-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside (white solid, 2.00 g, yield 43.4%).
[0048] Step 2: In a reaction flask, add cinnamyl alcohol-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside (1.86 g, 4.0 mmol), 50 mL of methanol, and sodium methoxide (54.02 mg, 1.0 mmol) sequentially. React at 25 °C for 2 h, then neutralize with hydrochloric acid solution. Wash the reaction solution twice with water, combine the aqueous phases, and extract with dichloromethane. Dry the organic phase with anhydrous sodium sulfate, filter, and remove the organic solvent by rotary evaporation under reduced pressure. Separate by silica gel column chromatography (eluent V). 二氯甲烷 V 甲醇 The ratio was 5:1, yielding cinnamyl alcohol-β-D-glucopyranoside (white powder, 1.15 g, yield 96.9%).
[0049] The product was characterized by various spectra, and the data are as follows:
[0050] 1 H NMR (400MHz, CDCl3): δ7.26(d,J=8.0Hz,2H),7.18(t,J=8.0Hz,2H),7.12(d,J=8.0Hz,1H),6.48(d,J=12.0Hz,1H),6.20( d,J=16.0Hz,1H),5.56(s,1H),5.28(s,1H),5.19(s,1H),4.34(d,J=12.0Hz,2H),4.14(s,2H),3.56(s,5H),3.19(s,1H); 13 C NMR (100MHz, CDCl3): δ136.4,133.1,128.6,127.8,126.6,125.1,101.9,76.2,75.6,73.3,70.3,69.3,61.0.HRMS(ESI)calcd for C 16 H 26 O6[M+Na] + 319.1152, found 319.1158.
[0051] Example 3: Thermal stability
[0052] Depend on Figure 7 It can be seen that cinnamyl alcohol begins to decompose at 76.3℃, exhibiting significant weight loss in the temperature range of 76.3-222.7℃, with the highest weight loss rate at 204.7℃ and a total weight loss rate of 99.9%. Cinnamyl alcohol-β-D-glucopyranoside begins to decompose at 194.5℃, exhibiting significant weight loss in the temperature range of 194.5-501.7℃, with the highest weight loss rate at 313.2℃ and a total weight loss rate of 93.6%. The data show that compared to cinnamyl alcohol, the thermal decomposition temperature of cinnamyl alcohol-β-D-glucopyranoside increases from 76.3℃ to 194.5℃, significantly improving thermal stability. Furthermore, the maximum thermal weight loss temperature increases from 204.7℃ to 313.2℃, which is close to the operating temperature for heating non-combustible cigarettes, indicating its potential application value in the formulation design of such tobacco products.
[0053] Example 4: Thermal pyrolysis products of cinnamyl alcohol-β-D-glucopyranoside
[0054] Accurately weigh 2 mg of cinnamyl alcohol-β-D-glucopyranoside and place it in a pyrolysis apparatus. Under a helium atmosphere, rapidly heat to 300 °C at a heating rate of 20 °C / ms. The total ion chromatogram of the pyrolysis products is shown below. Figure 8As shown in the figure, cinnamyl alcohol-β-D-glucopyranoside can effectively release cinnamyl alcohol flavoring substances upon heating.
[0055] Example 5: Preparation and sensory evaluation of cigarette paper containing cinnamyl alcohol-β-D-glucopyranoside
[0056] 5g of cinnamyl alcohol-β-D-glucopyranoside was weighed and dissolved in 995g of anhydrous ethanol to prepare a 0.5% solution. Then, 9000g of water was added to this ethanol solution to dilute it and obtain a coating solution with a mass percentage of 0.05%. The coating was applied to the inner surface of cigarette paper using an offline gravure coating machine at a speed of 100m / min. Hot air drying was used, and the oven temperature was controlled at 70℃. After coating, the sample roll was rewound and stretched, then slit to obtain cigarette paper samples, in which the cinnamyl alcohol-β-D-glucopyranoside content was approximately 0.005%.
[0057] Cigarettes were made using tobacco from a specific specification of Huangshan brand cigarettes and the aforementioned cigarette paper. The control group consisted of cigarettes made with the same tobacco and cigarette paper without added cinnamyl alcohol-β-D-glucopyranoside.
[0058] The evaluation results showed that cigarettes using cigarette paper containing cinnamyl alcohol-β-D-glucopyranoside can enhance the spicy and sweet aroma during smoking, resulting in a better aroma quality, increased smoke concentration, a more delicate and mellow smoke, reduced off-flavors and irritation, and a cleaner and more comfortable mouthfeel. Furthermore, the aroma content at the beginning and end of the smoking process was not significantly different from the beginning, showing good consistency.
[0059] The above description is merely an exemplary embodiment of the present invention and is not intended to limit the present invention. Any modifications, equivalent substitutions, and improvements made within the spirit and principles of the present invention should be included within the protection scope of the present invention.
Claims
1. A method for preparing a sweet and spicy cigarette paper containing cinnamyl alcohol-β-D-glucopyranoside, characterized in that: Cinnamyl alcohol-β-D-glucopyranoside was dissolved in an alcohol-water mixed solvent to obtain a coating solution; the coating solution was coated onto the inner surface of cigarette paper using a gravure coating method, and after hot air drying, the sweet and spicy cigarette paper containing cinnamyl alcohol-β-D-glucopyranoside was obtained. The general structural formula of the cinnamyl alcohol-β-D-glucopyranoside compound is: ; The reaction formula for the synthesis of the cinnamyl alcohol-β-D-glucopyranoside compound is shown below: ； The synthesis method includes the following steps: Step 1: Add α-bromotetraacetyl glucose (Structure I), cinnamyl alcohol (Structure II), base, and first solvent sequentially to a round-bottom flask. Under stirring, slowly add Au-Ag nanoclusters as catalyst and react at 20-50°C for 3-8 h. After the reaction is complete, filter the mixture. The resulting residue is washed, dried, and recycled. Wash the resulting reaction solution twice with water. Combine the aqueous phases and extract with dichloromethane. Dry the organic phase with anhydrous sodium sulfate, filter, and evaporate under reduced pressure. Separate the intermediate product (Structure III) by silica gel column chromatography. Step 2: Add the base and the second solvent directly to the intermediate product obtained in Step 1, and react at 20-50℃ for 1-4 h; after the reaction is completed, add hydrochloric acid solution to neutralize to neutral. The reaction solution was washed twice with water, the aqueous phases were combined and extracted with dichloromethane, the organic phase was dried with anhydrous sodium sulfate, filtered and the organic solvent was removed by rotary evaporation under reduced pressure, and separated by silica gel column chromatography to obtain cinnamyl alcohol-β-D-glucopyranoside with the structural formula shown in Formula IV. The structural formula of the Au-Ag nanoclusters is [Au9Ag4(Dppp)4Cl4]. + Cl - It is prepared by the following method: To a mixed solution of ethanol and dichloromethane containing chloroauric acid tetrahydrate, 1,3-bis(diphenylphosphine)propane Dppp was added and stirred for 30 minutes. An ethanol solution containing silver nitrate was added to the reaction system while stirring. Subsequently, an ethanol solution containing sodium borohydride was added to the reaction system, and the mixture was aged for 3 hours. Then, concentrated hydrochloric acid was added dropwise, and after etching for 1 to 2 days, the supernatant was obtained by centrifugation. The supernatant was concentrated and washed with water and ether to obtain a solid powder. The obtained solid powder was dissolved in dichloromethane, separated by thin-layer chromatography, and the concentrated solid precipitated as pure Au-Ag cluster crystals in a dichloromethane / n-pentane system at 4°C for two to three weeks.
2. The preparation method according to claim 1, characterized in that, In step 1: the base is at least one of potassium hydroxide, sodium hydroxide, potassium carbonate, DBU, pyridine, and triethylamine; the first solvent is at least one of tetrahydrofuran, dioxane, dichloromethane, toluene, ethyl acetate, dimethyl sulfoxide, and petroleum ether; the eluent used for silica gel column chromatography is composed of petroleum ether and ethyl acetate in a volume ratio of 1-10:
1.
3. The preparation method according to claim 1, characterized in that: In step 1, the molar ratio of α-bromotetraacetyl glucose, cinnamyl alcohol, base, and catalyst is 1:1-1.5:1.1-2:0.005-0.
1.
4. The preparation method according to claim 1, characterized in that, In step 2: the alkali is at least one of sodium methoxide, sodium hydroxide, potassium carbonate, pyridine, and triethylamine; the second solvent is at least one of methanol, ethanol, tetrahydrofuran, dioxane, and dimethyl sulfoxide; the eluent used for silica gel column chromatography is composed of dichloromethane and methanol in a volume ratio of 1-10:
1.
5. The preparation method according to claim 1, characterized in that: In step 2, the molar ratio of the intermediate product to the base is 1:0.2-1.
6. The preparation method according to claim 1, characterized in that: The molar ratio of chloroauric acid tetrahydrate, 1,3-bis(diphenylphosphine)propane, silver nitrate, and sodium borohydride is 1:0.8-1.2:0.5-1:0.8-1.
2.
7. The preparation method according to claim 1, characterized in that: The amount of cinnamyl alcohol-β-D-glucopyranoside added is 0.0001%-0.01% of the weight of cigarette paper.
8. The preparation method according to claim 1, characterized in that: The alcohol-water mixed solvent is ethanol / water or propylene glycol / water.
9. The preparation method according to claim 1, characterized in that: The coating machine speed is controlled at 80-120 m / min, and the drying temperature is controlled at 50-90℃.