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Column [5] arene and anethole inclusion compound and preparation method and application thereof

A technology of anethole and clathrate, which is applied in the clathrate of pillar [5] aromatic hydrocarbons and anethole and its preparation, and can solve the problem that it cannot be directly applied to the field of tobacco, the quality of cigarettes is difficult to guarantee, and anethole has a burnt smell, etc. problem, achieve the effect of overcoming the instability and volatility, the preparation method is simple and easy, and the thermal stability is good

Pending Publication Date: 2021-01-29
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the traditional essential oils are volatile at room temperature, so it is difficult to use anethole as a flavor additive in the production of cigarettes and the quality is difficult to guarantee. How to apply anethole as a flavor additive in the field of tobacco while maintaining its stability at high temperatures is currently an issue. There are technical problems to be solved
[0004] In the prior art, Zhao Xinghua et al. studied the "Preparation Process of Natural Anethole β-cyclodextrin Inclusion Compound Using the Uniform Design Method", and used β-cyclodextrin as the inclusion compound carrier to include anethole in it. Trying to increase the sustained-release effect of anethole, but its release temperature is low, and there is a burnt smell when releasing anethole at high temperature, so it cannot be directly applied to the field of tobacco

Method used

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  • Column [5] arene and anethole inclusion compound and preparation method and application thereof
  • Column [5] arene and anethole inclusion compound and preparation method and application thereof
  • Column [5] arene and anethole inclusion compound and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0033] Embodiment 1: Preparation of methoxypillar [5] arene and anethole clathrate

[0034] Put 7.3 g of p-dimethoxybenzene in a three-necked flask, add 80 mL of dichloroethane, ultrasonically until the white solid is completely dissolved, then add 5 g of paraformaldehyde, stir for half an hour to fully dissolve, heat up to 30 °C, Add 6.5 mL of boron trifluoride diethyl ether and continue to stir until the color turns dark green to black, then add 10 mL of methanol, and finally add a large amount of methanol until the product precipitates. Separation by suction filtration, dissolving the filter residue in dichloromethane, filtering to remove insoluble impurities, and finally spin-drying to obtain the crude methoxypillar[5]arene with a yield of 90%. H NMR spectrum such as figure 1 Shown, aromatic hydrogen: methylene hydrogen: methyl hydrogen = 10:10:30.

[0035] Add 0.1 mmol of pillar[5]arene (R is -CH 3 ) and 0.1 mmol of trans-anethole were stirred at 20°C for 20 hours, th...

Embodiment 2

[0036] Embodiment 2: Preparation of ethoxylated pillar [5] arene and anethole clathrate

[0037] Put 3.78 g, 10 mmoL ethoxy-2,5-dibenzyloxymethylbenzene in a three-necked flask, add 80 mL of dichloromethane, sonicate until the white solid is completely dissolved, then add 0.172 g of p-toluenesulfonic acid, stir for half Hours to fully dissolve the mixture, raise the temperature to 40°C, and continue stirring for two hours. It was extracted and separated, and the organic phase was washed with water and saturated brine, and then dried over anhydrous sodium sulfate. After spin-drying, pass through a silica gel column, use petroleum ether: ethyl acetate = 40:1 as a developer, and finally spin-dry to obtain the crude ethoxy column [5] aromatics with a yield of 95%.

[0038] 0.2 mmol of ethoxypillar[5]arene (R is -CH 2 CH 3 ) and 0.5 mmol of trans-anethole at 50°C for 1 hour, then drop the mixture into 20 mL of organic solvent such as ethanol to precipitate the precipitate, filte...

Embodiment 3

[0039] Example 3: Preparation of Hydroxypillar [5] Arene and Anethole Inclusion Complex

[0040] Put 0.34 g of p-methoxypyr[5]arene in a flask, add 20 mL of chloroform, then add 2.4 g of boron tribromide, stir at room temperature for 96 hours, filter with suction, and wash the filter residue with water. Pass through a silica gel column, use dichloromethane: acetone = 1:1 as the developer, and spin dry to obtain 0.21 g of a white solid, 0.36 mmol, with a yield of 90%.

[0041] Stir 0.1 mmol of hydroxylated pillar[5]arene (R is -H) and 0.1 mmol of trans-anethole at 50°C for 5 hours, then drop the mixture into 30 mL of methanol to precipitate a precipitate, filter or The solution and the precipitate were separated by centrifugation, and the precipitate was dried to obtain the clathrate with a yield of 98%.

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Abstract

The invention discloses a column [5] arene and anethole inclusion compound and a preparation method and application thereof, and the preparation method comprises the following steps: mixing and stirring column [5] arene and anethole to obtain a mixed solution, dropwise adding the mixed solution into an organic solvent, stirring for inclusion reaction, dividing a reaction product into an upper layer and a lower layer, taking lower-layer precipitate through suction filtration or centrifugation, drying the precipitate in a drying oven to obtain the column [5] arene and anethole inclusion compound; the anethole is cis-anethole or trans-anethole, the structural formula of the column [5] arene is shown in the specification, R is one or more of -CH3, -CH2OH, -CH2NH2, -CH2Br, -CH2CH3, -H, -CH2COOH, -CH2COOCH3 and -CH2COOCH2CH3, and the anethole in the clathrate has good slow-release function and stability and has no burnt smell when applied to tobacco products.

Description

technical field [0001] The invention relates to the technical field of tobacco essence and fragrance, in particular to an inclusion compound of pillar[5]arene and anethole, its preparation method and application. Background technique [0002] Anethole, also known as anethole (natural), is found in Burley tobacco leaves and essential oils such as anise, cumin, and star anise oils. Cumin ( Foenicuzu vulgare Mill) is the dry ripe fruit of umbelliferous plant fennel, which is not only a condiment, but also a traditional Chinese medicine. Anethole is widely used in food, beverages, toothpaste, gargle, and can also be used as a flavoring agent and flavoring agent for medicines, a fragrance for cosmetics and soaps, a raw material for synthetic drugs, and a sensitizer for color photography. At the same time, studies have shown that anethole has a certain antibacterial effect on R. apple, but anethole monomer is volatile and unstable, so it is difficult to be directly applied to t...

Claims

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Application Information

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IPC IPC(8): C11B9/00A24B3/12
CPCC11B9/0061A24B3/12
Inventor 刘晶王海琨杨波王保兴李忠卢伟苏丹丹
Owner CHINA TOBACCO YUNNAN IND