Tobacco sweetening agent as well as preparation method and application thereof
Through molecular modification, the alkyl-modified dehydrated sugar sweet aroma raw material is synthesized, which solves the problem of unstable and volatile aroma properties of traditional tobacco sweeteners, and achieves the stability of chemical properties of tobacco sweeteners and the long-term maintenance of smoke sweeteners.
Patent Information
- Application Number
- CN202411763884.6
- Authority / Receiving Office
- CN · China
- Patent Type
- Applications(China)
- Current Assignee / Owner
- Filing Date
- 2024-12-03
- Publication Date
- 2025-03-07
AI Technical Summary
Traditional tobacco sweeteners have unstable aroma properties and are easy to evaporate, making it difficult to maintain the sweetness and sensory quality of cigarettes for a long time.
The alkyl-modified dehydrated sugar sweet aroma raw material was synthesized through molecular modification, and the reaction was carried out under specific conditions using 1,4:3,6-di-dehydrated-D-glucopyranose as the starting material, including reaction under specific wavelength irradiation of the LED lamp, and the target compound was obtained through extraction, drying, purification and other steps.
It achieves stable chemical properties of tobacco sweeteners and is not easy to evaporate. It can increase the sweetness of smoke for a long time, enrich the tobacco fragrance, and improve the comfort of the aftertaste.
Smart Images
Figure CN119569796A_ABST
Abstract
Description
Technical Field
[0001] The present invention relates to the technical field of organic synthesis, and in particular to a tobacco sweetener and a preparation method and application thereof. Background Art
[0002] 1,4:3,6-dianhydro-D-pyranose glucose is commonly found in cigarette smoke and sugar pyrolysis products. It is a pyran compound generated by sugar degradation. It is volatile, fat-soluble and water-soluble, and can increase the sweetness of cigarettes. However, this compound is easy to volatilize after being added to cigarettes, and its flavoring properties are unstable.
[0003] Therefore, compounds with stable flavoring properties and highlighting the sweet taste of cigarettes can be synthesized through molecular modification design and added to cigarettes as tobacco flavorings. Summary of the invention
[0004] The technical problem to be solved by the present invention is to provide a tobacco sweetener and a preparation method and application thereof, so as to solve the problem that the flavoring properties of traditional tobacco sweeteners are unstable and volatile, and to synthesize new dehydrated sugar alkoxy compounds through molecular modification to improve the sweetness and sensory quality of cigarettes, while ensuring that the chemical properties are stable and not volatile.
[0005] The technical problem to be solved by the present invention is achieved through the following technical solutions:
[0006] A tobacco sweetener, the structural formula of the tobacco sweetener is as follows:
[0007]
[0008] A method for preparing a tobacco sweetener comprises the following steps:
[0009]
[0010] (1) Adding raw materials 1,4:3,6-dianhydro-D-pyranose glucose, alcohol, catalyst, additives and solvent into a reaction bottle, stirring the reaction system evenly, and reacting at 20-40° C. for 12-24 hours under the condition of LED light with a specific wavelength;
[0011] (2) After the reaction is completed, dichloromethane and saturated sodium chloride solution are added, and the organic phase is extracted and separated and dried over anhydrous sodium sulfate. The reaction solvent is evaporated and the residue is purified by silica gel column chromatography to obtain the target compound.
[0012] Preferably, in the above technical solution, in step (1), the catalyst is ferrous chloride, cuprous chloride or cobalt chloride; the additive is calcium chloride, magnesium chloride or zinc chloride; the solvent is selected from one or more of dichloromethane, acetone or acetonitrile; and the alcohol is ethanol, propanol, hexadecanol or heptadecanol.
[0013] Preferably, in the above technical solution, in step (1), the molar ratio of 1,4:3,6-dianhydro-D-pyranose, alcohol, catalyst and additive is 1:(1.0-5.0):(0.05-0.2):(1.0-5.0).
[0014] Preferably, in the above technical solution, in step (1), the wavelength range of the LED light is 300 to 400 nm.
[0015] Preferably, in the above technical solution, in step (2), the volume ratio of dichloromethane and saturated sodium chloride solution to the solution in step (1) is 1:1-1:2, the volume ratio of dichloromethane and saturated sodium chloride is 1:1, and the extraction time is 1-5 min.
[0016] Preferably, in the above technical solution, in step (2), the silica gel column chromatography uses petroleum ether and ethyl acetate as eluents in a volume ratio of 3:1-1:1, and gradient elution.
[0017] Application of a tobacco sweetener in cigarettes.
[0018] Preferably, in the above technical solution, the tobacco sweetener is applied to cigarettes as a flavoring agent, and the added amount is 1 to 50 ppm based on the mass of the cigarette tobacco.
[0019] A cigarette comprising a tobacco sweetener.
[0020] The above technical solution of the present invention has the following beneficial effects:
[0021] The present application uses 1,4:3,6-dianhydro-D-pyranose glucose as the starting material to synthesize an alkyl-modified dehydrated sugar sweet flavor raw material. The flavor is added to cigarettes with stable chemical properties and is not easy to volatilize. It can increase the sweetness of smoke, enrich the smoke aroma, and improve the comfort of the aftertaste. BRIEF DESCRIPTION OF THE DRAWINGS
[0022] The accompanying drawings, which are incorporated in and constitute a part of the specification, illustrate embodiments of the invention and, together with the description, serve to explain the principles of the invention.
[0023] Figure 1 The compound obtained in Example 1 1 H NMR spectrum;
[0024] Figure 2 The compound obtained in Example 1 13 C NMR spectrum. DETAILED DESCRIPTION
[0025] Various exemplary embodiments of the present invention will now be described in detail with reference to the accompanying drawings. It should be noted that the relative arrangement of components and steps, numerical expressions and numerical values set forth in these embodiments do not limit the scope of the present invention unless otherwise specifically stated.
[0026] Unless otherwise specified, the reagents used in this application are all commercially available or obtained through commercial channels, or can be prepared by referring to existing chemical methods.
[0027] Example 1
[0028] A method for preparing a tobacco sweetener:
[0029] (1) In a 100 mL round-bottom flask, add 1.44 g (10 mmol) of 1,4:3,6-dianhydro-D-pyranose, 0.23 g (50 mmol) of ethanol, 0.126 g (1 mmol) of ferrous chloride, 2.22 g (20 mmol) of calcium chloride and 20 mL of acetonitrile. After the reaction system is stirred evenly, react at 30 °C for 12 h under the condition of irradiation with a specific wavelength of 400 nm from an LED lamp.
[0030] (2) After the reaction, dichloromethane and saturated sodium chloride solution (10 mL each) were added, and the organic phase was extracted and separated for 1-5 min and dried over anhydrous sodium sulfate. The reaction solvent was evaporated and the residue was purified by silica gel column chromatography (the eluent was a mixture of petroleum ether and ethyl acetate in a volume ratio of 3:1-1:1, gradient elution) to obtain 1.38 g of the target compound with a yield of 80.2%.
[0031] The structural formula of the target compound is shown in Formula I below:
[0032]
[0033] Its hydrogen spectrum is Figure 1 As shown, the carbon spectrum is Figure 2 shown.
[0034] Example 2
[0035] A method for preparing a tobacco sweetener:
[0036] (1) In a 100 mL round-bottom flask, add 1.44 g (10 mmol) of 1,4:3,6-dianhydro-D-pyranose, 0.30 g (50 mmol) of propanol, 0.252 g (2 mmol) of ferrous chloride, 2.22 g (20 mmol) of calcium chloride and 20 mL of dichloromethane. After the reaction system is stirred evenly, react at 30 °C for 24 h under the condition of irradiation with a specific wavelength of 400 nm from an LED lamp.
[0037] (2) After the reaction, dichloromethane and saturated sodium chloride solution (10 mL each) were added, and the organic phase was extracted and separated for 1-5 min and dried over anhydrous sodium sulfate. The reaction solvent was evaporated and the residue was purified by silica gel column chromatography (the eluent was a mixture of petroleum ether and ethyl acetate in a volume ratio of 3:1-1:1, gradient elution) to obtain 1.66 g of the target compound with a yield of 71.2%.
[0038] The structural formula of the target compound is shown in Formula II below:
[0039]
[0040] Example 3
[0041] A method for preparing a tobacco sweetener:
[0042] (1) In a 100 mL round-bottom flask, add 1.44 g (10 mmol) of 1,4:3,6-dianhydro-D-pyranose, 0.24 g (10 mmol) of hexadecanol, 0.126 g (1 mmol) of ferrous chloride, 2.22 g (20 mmol) of calcium chloride and 20 mL of acetonitrile. After the reaction system is stirred evenly, react at 30 °C for 12 h under the condition of irradiation with a specific wavelength of 400 nm from an LED lamp.
[0043] (2) After the reaction, dichloromethane and saturated sodium chloride solution (10 mL each) were added, and the organic phase was extracted and separated for 1-5 min and dried over anhydrous sodium sulfate. The reaction solvent was evaporated and the residue was purified by silica gel column chromatography (the eluent was a mixture of petroleum ether and ethyl acetate in a volume ratio of 3:1-1:1, gradient elution) to obtain 2.47 g of the target compound with a yield of 67.2%.
[0044] The structural formula of the target compound is shown in Formula III below:
[0045]
[0046] Flavor performance test: Weigh the sweetener obtained in Examples 1-3, dilute it with ethanol to a 1% solution for later use. Weigh 50g of blank cigarette shreds without flavoring or adding materials, spray the ethanol solution of the compound evenly on the shreds, and prepare shredded cigarettes with a compound to shreds ratio of 1ppm, 10ppm, 50ppm and 100ppm, seal and place for 4h, put in a 50℃ oven to dry, humidify with distilled water to standard moisture (12%), roll into standard cigarettes, balance moisture (humidity 60%±2%, temperature 22±1℃) for 48h before evaluation. The control sample is a blank cigarette, and the control sample is balanced for 48h under the same temperature and humidity conditions.
[0047] Table 1 Sensory evaluation results
[0048]
[0049] It can be seen from Table 1 that sweeteners have the effect of increasing the sweetness of smoke and significantly improving and modifying the aroma of cigarettes. The appropriate dosage is: 1-50ppm.
[0050] Although the present invention has been disclosed as above by the embodiments, it is not intended to limit the present invention. Any person skilled in the art may make various choices and modifications without departing from the spirit and scope of the present invention. Therefore, the protection scope of the present invention is limited by the claims and their equivalents.
Claims
1. A tobacco sweetener, characterized in that The structural formula of the tobacco sweetener is as follows:
2. The method for preparing the tobacco sweetener according to claim 1, characterized in that: The following steps are involved: (1) Adding raw materials 1,4:3,6-dianhydro-D-pyranose glucose, alcohol, catalyst, additives and solvent into a reaction bottle, stirring the reaction system evenly, and reacting at 20-40° C. for 12-24 hours under the condition of LED light with a specific wavelength; (2) After the reaction is completed, dichloromethane and saturated sodium chloride solution are added, and the organic phase is extracted and separated and dried over anhydrous sodium sulfate. The reaction solvent is evaporated and the residue is purified by silica gel column chromatography to obtain the target compound.
3. The method for preparing the tobacco sweetener according to claim 2, characterized in that: In step (1), the catalyst is ferrous chloride, cuprous chloride or cobalt chloride; the additive is calcium chloride, magnesium chloride or zinc chloride; the solvent is selected from one or more of dichloromethane, acetone or acetonitrile; and the alcohol is ethanol, propanol, hexadecanol or heptadecanol.
4. The method for preparing the tobacco sweetener according to claim 2, characterized in that: In step (1), the molar ratio of 1,4:3,6-dianhydro-D-pyranose, alcohol, catalyst and additive is 1:(1.0-5.0):(0.05-0.2):(1.0-5.0).
5. The method for preparing the tobacco sweetener according to claim 2, characterized in that: In step (1), the wavelength range of LED light is 300-400 nm.
6. The method for preparing the tobacco sweetener according to claim 2, characterized in that: In step (2), the volume ratio of dichloromethane and saturated sodium chloride solution to the solution in step (1) is 1:1-1:2, the volume ratio of dichloromethane and saturated sodium chloride is 1:1, and the extraction time is 1-5 min.
7. The method for preparing the tobacco sweetener according to claim 2, characterized in that: In step (2), the silica gel column chromatography uses petroleum ether and ethyl acetate as eluents in a volume ratio of 3:1-1:1, and gradient elution.
8. Use of the tobacco sweetener according to claim 1 or the tobacco sweetener prepared by the preparation method according to any one of claims 2 to 7 in cigarettes.
9. The use according to claim 8, characterized in that: The tobacco sweetener is used as a flavor in cigarettes, and the added amount is 1 to 50 ppm of the mass of the cigarette shreds.
10. A cigarette, characterized in that: The cigarette contains the tobacco sweetener according to claim 1 or the tobacco sweetener prepared by the preparation method according to any one of claims 2-7.