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Menthol perfume precursor compound, preparation method and application of menthol perfume precursor compound

A technology of precursor compounds, menthol, applied in the fields of application, food science, organic chemistry, etc., to achieve the effect of promoting research on cigarette flavoring, low volatility, and large-scale production research value

Active Publication Date: 2017-11-24
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although some menthyl ester compounds have been put into use, their volatility and stability still need to be further improved

Method used

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  • Menthol perfume precursor compound, preparation method and application of menthol perfume precursor compound
  • Menthol perfume precursor compound, preparation method and application of menthol perfume precursor compound
  • Menthol perfume precursor compound, preparation method and application of menthol perfume precursor compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Preparation of menthyl succinate monoester by melting method: add 10mmol menthol to a 100ml round bottom flask, heat until melted, then add 10mmol succinic anhydride, 0.1mmol p-toluenesulfonic acid as a catalyst, and stir at 100°C for 1h. The obtained product was separated by silica gel column chromatography (petroleum ether: ethyl acetate volume ratio = 10:1) to obtain pure menthyl succinate.

[0037] Preparation of acid chloride: Add 10 mmol of menthyl succinate and 10 mmol of thionyl chloride to a 50 ml round-bottomed flask successively, and stir at 0°C for 3 h. Remove excess thionyl chloride by rotary evaporation to obtain the acyl chloride substrate (succinic acid menthyl chloride).

[0038] Preparation of menthol maltol succinate:

[0039] Add 20mmol of anhydrous sodium carbonate, 100ml of dichloromethane, 20mmol of maltol, and 20mmol of the acid chloride obtained in Example 2 to a 250ml round-bottomed flask, stir at room temperature, and add 0.02mmol of triethyl...

Embodiment 2

[0045]Preparation of menthyl succinate monoester by melting method: add 100mmol menthol to a 100ml round bottom flask, heat until melted, then add 10mmol succinic anhydride, 10mmol p-toluenesulfonic acid as a catalyst, and stir at 160°C for 10h. The obtained product was separated by silica gel column chromatography (petroleum ether: ethyl acetate volume ratio = 10:1) to obtain pure menthyl succinate.

[0046] Preparation of acid chloride: Add 10 mmol of menthyl succinate and 100 mmol of thionyl chloride to a 50 ml round bottom flask successively, and stir at 80° C. for 8 h. Remove excess thionyl chloride by rotary evaporation to obtain the acyl chloride substrate (succinic acid menthyl chloride).

[0047] Preparation of menthol maltol succinate:

[0048] Add 10mmol of anhydrous sodium carbonate, 100ml of dichloromethane, 1mmol of maltol, 10mmol of the acid chloride prepared above in Example 2 to a 100ml round-bottom flask in turn, stir at room temperature, and add 0.01mmol of...

Embodiment 3

[0050] Preparation of menthyl succinate monoester by melting method: add 50mmol menthol to a 100ml round bottom flask, heat until melted, then add 10mmol succinic anhydride, 1.5mmol p-toluenesulfonic acid as a catalyst, and stir at 120°C for 6h. The obtained product was separated by silica gel column chromatography (petroleum ether: ethyl acetate volume ratio = 10:1) to obtain pure menthyl succinate.

[0051] Preparation of acid chloride: Add 10 mmol of menthyl succinate and 50 mmol of thionyl chloride to a 50 ml round bottom flask successively, and stir at 60°C for 5 h. Remove excess thionyl chloride by rotary evaporation to obtain the acyl chloride substrate (succinic acid menthyl chloride).

[0052] Preparation of menthol maltol succinate:

[0053] Add 40mmol of anhydrous sodium carbonate, 100ml of dichloromethane, 10mmol of maltol, 50mmol of the acid chloride prepared above in Example 3 to a 250ml round-bottomed flask in turn, stir at room temperature, and add 0.05mmol of...

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Abstract

The invention relates to a menthol perfume precursor compound, a preparation method and application of the menthol perfume precursor compound, belonging to the technical field of perfume chemistry. The compound provided by the invention is the compound as shown in formula (I) described in the specification or the salt of the compound as shown in the formula (I). The preparation method comprises the following steps: by taking menthol and succinic anhydride as raw materials and reacting under the catalytic effect of p-toluenesulfonic acid, thereby acquiring monobutyl succinate monoester; reacting monoester with thionyl chloride, thereby acquiring acyl chloride; reacting acyl chloride with maltol, thereby acquiring the final product (menthol maltol ester). The compound acquired according to the technical scheme provided by the invention has high stability; the volatility of the compound is lower than that of the traditional perfume menthol; the compound has peppermint fragrant and sweet flavor; the operation process is simple; the application prospect is wide.

Description

technical field [0001] The invention belongs to the technical field of fragrance chemistry, and in particular relates to a menthol fragrance precursor compound and a preparation method and application thereof. Background technique [0002] In the process of cigarette production, many tobacco flavoring agents have problems such as strong volatility and easy sublimation, and the life of cigarettes will be shortened due to the volatilization and escape of flavoring agents during storage. On the other hand, too much flavoring agent for tobacco may destroy the tobacco natural aroma of cigarettes. Recent research has involved the incorporation of low volatility organic additives into vaping products. When burned, the additive pyrolyzes into one or more fragments that improve the taste and aroma of mainstream and sidestream smoke. This organic additive is called latent aroma substance for tobacco. [0003] There are some latent aroma substances in tobacco itself, such as cibarde...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/40A24B15/40
CPCA24B15/403C07D309/40
Inventor 孙柏旺钱东尔余佳张雅雯朱岭军周其荣季明星孙鹏缪明明王昆淼刘志华
Owner CHINA TOBACCO YUNNAN IND
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