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2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonic acid nerol ester and application thereof

A technology of nerol ester and nerol, applied in the field of cigarette flavor synthesis, can solve the problems of easy deterioration and damage, poor stability of DDMP and the like

Inactive Publication Date: 2021-03-30
CHINA TOBACCO HENAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, DDMP has poor stability and is easy to deteriorate and damage, so it has not been used as a raw material for tobacco aroma.

Method used

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  • 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonic acid nerol ester and application thereof
  • 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonic acid nerol ester and application thereof
  • 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonic acid nerol ester and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Under nitrogen protection, nerol (1.54g, 10mmol) was dissolved in 30mL of anhydrous dichloromethane, the reaction system was cooled to 0°C, and triethylamine (2.42g, 24mmol) and trichloromethyl chloroformate ( 0.98g, 3.3mmol), after the addition, react at room temperature for 2h, then add 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (1.44g , 10mmol), continue the reaction at room temperature for 3h, wash the reaction solution with saturated sodium chloride solution after the reaction, separate the organic layer, dry over anhydrous sodium sulfate, evaporate the solvent, and the residue is purified by silica gel column chromatography, petroleum ether ( V): Elution with ethyl acetate (V)=5:1 to obtain 2.66g of the target product 2,3-dihydro-3-hydroxyl-6-methyl-4H-pyran-4-one-5-O- Neryl carbonate (DDMP neryl carbonate), yield 82.6%.

Embodiment 2

[0023] Under nitrogen protection, nerol (1.54g, 10mmol) was dissolved in 30mL of anhydrous chloroform, the reaction system was cooled to 0°C, and pyridine (2.37g, 30mmol) and trichloromethyl chloroformate (0.98g ,3.3mmol), after the addition, react at room temperature for 2h, then add 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (1.44g, 10mmol ), continue to react for 3h at room temperature, wash the reaction solution with saturated sodium chloride solution after the reaction, separate the organic layer, dry over anhydrous sodium sulfate, evaporate the solvent, and the residue is purified by silica gel column chromatography, petroleum ether (V) : Elution with ethyl acetate (V) = 5:1 to obtain 2.56g of target 2,3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-orange carbonate Ethyl alcohol ester (DDMP neryl carbonate), yield 79.0%.

Embodiment 3

[0025] Under nitrogen protection, dissolve nerol (1.54g, 10mmol) in 30mL of anhydrous 1,2-dichloroethane, cool the reaction system to 0°C, and add diisopropylethylamine (3.88g, 30mmol) in sequence and trichloromethyl chloroformate (1.19g, 4mmol), react at room temperature for 3h after the addition, and then add 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran to the reaction system -4-ketone (1.44g, 10mmol), continue to react at room temperature for 3h, wash the reaction solution with saturated sodium chloride solution after the reaction, separate the organic layer, dry over anhydrous sodium sulfate, evaporate the solvent, and pass the residue through silica gel Purified by column chromatography, eluting with petroleum ether (V): ethyl acetate (V) = 5:1, to obtain 2.24 g of the target product 2,3-dihydro-3-hydroxy-6-methyl-4H-pyran-4 - Keto-5-O-nerol carbonate (DDMP nerol carbonate), yield 69.1%.

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Abstract

The invention relates to 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonic acid nerol ester and application thereof, and the technical scheme is as follows: 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone and nerol are used as raw materials to prepare 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonic acid nerol ester. The compound has good storage stability and perfumingstability, and can be split to release 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone and nerol after the cigarette raw material containing the compound is added into cigarettes, so that theeffects of increasing the sweet feeling of the oral cavity and improving the aftertaste comfort can be achieved. The fragrance of smoke can be increased, the aroma quality of cigarettes is improved, and potential application value is achieved.

Description

technical field [0001] The invention belongs to the technical field of synthesis of tobacco spices, in particular to 2,3-dihydro-3-hydroxyl-6-methyl-4H-pyran-4-one-5-O-nerol carbonate and its use as a spice in Application in cigarettes. Background technique [0002] The "sweetness" feature is the most basic and important component in the taste profile of cigarettes, and it is also one of the most concerned style features in cigarette flavoring. In order to improve the sweet taste of cigarettes, substances such as sugars, extracts and Maillard reactants are usually used in cigarette flavoring. 2,3-Dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) is commonly found in cigarette smoke, Maillard reaction products, sugar cleavage products and natural extracts middle. It has a significant positive correlation with the "sweetness" of smoke, which can significantly improve the sweetness of cigarette smoke and highlight the "sweet" and "moist" taste characteristics of cigarette...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/32A24B3/12A24B15/40
CPCC07D309/32A24B15/403A24B3/12
Inventor 席高磊陈芝飞付瑜锋赵志伟王清福刘强段鹍马宇平
Owner CHINA TOBACCO HENAN IND
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