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2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate and application thereof

A technology of methyl alcohol ester and benzyl alcohol, applied in the field of cigarette fragrance synthesis, can solve problems such as poor stability of DDMP, which has not yet been applied, etc.

Pending Publication Date: 2021-03-26
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 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-ketone-5-O-benzyl carbonate and application thereof
  • 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate and application thereof
  • 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] DDMP (2.88g, 20mmol) was dissolved in 50mL of anhydrous dichloromethane, cooled to 0°C, and under nitrogen protection, triethylamine (2.42g, 24mmol) and benzyl chloroformate (3.58g, 21mmol) were added successively, and Bi rose to 25 ° C for 6h. The reaction solution was washed with saturated sodium chloride solution, the organic layer was separated, dried over anhydrous sodium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography to obtain 5.06 g of the target 2,3-dihydro-3-hydroxy-6 -Methyl-4H-pyran-4-one-5-O-benzyl carbonate, yield 91.0%.

Embodiment 2

[0025] DDMP (2.88g, 20mmol) was dissolved in 50mL of anhydrous chloroform, cooled to 0°C, and under nitrogen protection, pyridine (1.90g, 20mmol) and benzyl chloroformate (4.26g, 25mmol) were added successively, and Bi l Reaction at 25°C for 6h. The reaction solution was washed with saturated sodium chloride solution, the organic layer was separated, dried over anhydrous sodium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography to obtain 4.89 g of the target 2,3-dihydro-3-hydroxy-6 -Methyl-4H-pyran-4-one-5-O-benzyl carbonate, yield 87.9%.

Embodiment 3

[0027] DDMP (2.88g, 20mmol) was dissolved in 50mL of acetonitrile, cooled to 0°C, and under nitrogen protection, pyridine (2.28g, 24mmol) and benzyl chloroformate (4.26g, 25mmol) were added successively, and the reaction was completed at 25°C 6h. The reaction solution was washed with saturated sodium chloride solution, the organic layer was separated, dried over anhydrous sodium sulfate, the solvent was evaporated, and the residue was purified by silica gel column chromatography to obtain 5.01 g of the target product 2,3-dihydro-3-hydroxy-6 -Methyl-4H-pyran-4-one-5-O-benzyl carbonate, yield 90.1%.

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Abstract

The invention relates to 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate and application thereof. According to the technical scheme, 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone is used as a raw material, and 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-benzyl carbonate is prepared through esterification reaction. The compound has good storage stability and perfuming stability, and can be cracked to release 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone and benzyl alcohol after being added into cigarettes, the effects of increasing the sweet feeling of the oral cavity and improving the aftertaste comfort can be achieved, the cigarette aroma can be enriched, the cigarette aroma quality is improved, and the potential application value is achieved.

Description

technical field [0001] The invention belongs to the technical field of flavor synthesis for tobacco, in particular to 2,3-dihydro-3-hydroxyl-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate and its use as flavor in cigarettes in the application. Background technique [0002] The "sweetness" of smoke is a key indicator that affects the sensory quality and style characteristics of cigarettes. In order to highlight this characteristic, substances such as sugars, extracts and Maillard reactants are usually used in Chinese cigarette flavoring, mainly because these substances Contains or can be cracked to produce volatile sweetening substances such as pyrones and anhydrosugars, but due to the extremely low content of these sweetening substances, the effect of highlighting the "sweetness" characteristics of cigarettes is not good. [0003] 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 ...

Claims

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Application Information

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IPC IPC(8): C07D309/32A24B15/40A24B3/12
CPCC07D309/32A24B3/12A24B15/403
Inventor 王清福陈芝飞赵志伟刘强付瑜锋孙志涛蔡莉莉许克静杜佳
Owner CHINA TOBACCO HENAN IND
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