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Preparation method and application of 8-methoxycoumarin-3-glucose ester formate

A technology of methoxy coumarin and glucose ester, which is applied in the field of preparation of tobacco flavors and fragrances, can solve the problems of short fragrance retention time and limited use, improve smoke and taste, increase production cost, and aroma retention time lengthening effect

Inactive Publication Date: 2014-08-06
CHINA TOBACCO HEBEI INDUSTRIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Sugar ester compounds are one of the important components of tobacco flavor raw materials. As the precursors of volatile flavor components, this type of compound has been recognized and valued by researchers in the tobacco flavor and fragrance industry at home and abroad, and its related research is also increasing. Many, but the fragrance lasts for a short time, which limits its use to a certain extent

Method used

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  • Preparation method and application of 8-methoxycoumarin-3-glucose ester formate
  • Preparation method and application of 8-methoxycoumarin-3-glucose ester formate
  • Preparation method and application of 8-methoxycoumarin-3-glucose ester formate

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] a. After adding 0.04mol or 8.8g of 8-methoxycoumarin-3-carboxylic acid and 0.20mol or 23.8g of thionyl chloride into the three-necked flask, stir and reflux at 80°C for 4 hours. After the reaction Rotary evaporation removes excess thionyl chloride to obtain light yellow solid powder 8-methoxycoumarin-3-formyl chloride;

[0025] b. After adding 25ml of dichloromethane, 12.14g (0.12mol) of anhydrous triethylamine and 9.0g (0.05mol) of glucose into the above container, stir the reaction at 40°C for 4h, add 30ml of distilled water after the reaction, and then use 20ml Petroleum ether was extracted 4 times, then dried with anhydrous sodium sulfate (or anhydrous magnesium sulfate or anhydrous calcium chloride) to remove the solvent, and further purified by silica gel column chromatography, wherein the eluent was petroleum ether and acetone at a ratio of 10: The mixed solution prepared in a volume ratio of 1 was purified to obtain 4.36 g of bean-flavored flavor 8-methoxycoum...

Embodiment 2

[0026] Embodiment 2: the difference between this embodiment and embodiment 1 is:

[0027] a. After adding 0.04mol or 8.8g of 8-methoxycoumarin-3-carboxylic acid and 0.08mol or 9.52g of thionyl chloride into the three-necked flask, stir and reflux at 80°C for 4 hours, and rotate after the reaction Evaporate and remove excess thionyl chloride to obtain light yellow solid powder 8-methoxycoumarin-3-formyl chloride;

[0028] b. After adding 25ml of dichloromethane, 12.66g (0.16mol) of anhydrous pyridine and 5.4g (0.03mol) of glucose into the above container, stir the reaction at 30°C for 4 hours, add 30ml of distilled water after the reaction, and then use 20ml of petroleum ether Extract 3 times, then dry with anhydrous magnesium sulfate (or anhydrous sodium sulfate or anhydrous calcium chloride), remove the solvent, and use silica gel column chromatography for further purification, wherein the eluent uses petroleum ether and acetone at a volume ratio of 10:1 Compared with the ...

Embodiment 3

[0029] Embodiment 3: the differences between this embodiment and embodiment 1 are:

[0030] a. After adding 0.04mol or 8.8g of 8-methoxycoumarin-3-carboxylic acid and 0.20mol or 23.8g of thionyl chloride into the three-necked flask, stir and reflux at 80°C for 4 hours, and rotate after the reaction Evaporate and remove excess thionyl chloride to obtain light yellow solid powder 8-methoxycoumarin-3-formyl chloride;

[0031] b. After adding 20ml of dichloromethane, 12.14g (0.12mol) of anhydrous triethylamine and 14.41g (0.08mol) of glucose into the above container, stir and react at 40°C for 3 hours, add 20ml of distilled water after the reaction, and then use 20ml Petroleum ether was extracted 3 times, then dried with anhydrous calcium chloride (or anhydrous magnesium sulfate or anhydrous sodium sulfate) to remove the solvent, and further purified by silica gel column chromatography, wherein the eluent was petroleum ether and acetone at a ratio of 10: The mixed solution prep...

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Abstract

The invention discloses a preparation method and an application of 8-methoxycoumarin-3-glucose ester formate. The preparation method comprises the following steps: mixing 8-methoxycoumarin-3-formic acid with thionyl chloride, subsequently performing backflow reaction till the 8-methoxycoumarin-3-formic acid is completely reacted, removing excessive thionyl chloride, further adding a solvent, a catalyst and glucose, reacting for 2-6 hours at 10-40 DEG C, and after the reaction is accomplished, separating and purifying to obtain a tobacco bean fragrance type condiment, namely, the 8-methoxycoumarin-3-glucose ester formate. The 8-methoxycoumarin-3-glucose ester formate is used in tobacco for improving the harmony and the gentleness of smoke of cigarette and reducing the oral and throat irritation and can remarkably improve the taste of cigarette, the fragrance is similar to that of 8-methoxycoumarin, but the fragrance lasts longer. The preparation process is simple, the reaction condition is gentle and safe, the industrial production is easy to achieve, a remarkable effect of improving the smoke of cigarette can be achieved by only adding a small amount of the 8-methoxycoumarin-3-glucose ester formate, the production cost of cigarette is hardly influenced, and great practicability is achieved.

Description

technical field [0001] The invention relates to a preparation method and application of flavor and fragrance for tobacco. Background technique [0002] Sugar ester compounds are one of the important components of tobacco flavor raw materials. As the precursors of volatile flavor components, this type of compound has been recognized and valued by researchers in the tobacco flavor and fragrance industry at home and abroad, and its related research is also increasing. Many, but the fragrance lasts for a short time, which limits its use to a certain extent. Using chemical methods to introduce some relatively stable groups to improve its thermal stability will effectively improve the perfuming effect, and the structure of coumarin derivatives has a relatively stable conjugated system, making coumarin derivatives more Coumarin itself has lower volatility and lower threshold, and coumarin derivatives have a similar aroma to tonka bean, and some derivatives have strong medicinal va...

Claims

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Application Information

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IPC IPC(8): C07H13/10C07H1/00A24B15/40
Inventor 潘文亮马洪亮姜兴涛王玉林李维娜霍晓辉郝建辉张彦伟胡立朝郝红铃鲍峰伟任志强
Owner CHINA TOBACCO HEBEI INDUSTRIAL CO LTD
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