2, 3-dihydro-3-O-acyl-5-hydroxy-6-methyl-4H-pyran-4-one, and preparation method and application thereof

A technology of dihydroxy and methyl, which is applied in the field of synthesis of tobacco flavors, can solve the problems of perishable damage, failure to make cigarettes, application, poor stability, etc.

Inactive Publication Date: 2021-03-09
CHINA TOBACCO HENAN IND +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The object of the present invention is to provide a kind of 2,3-dihydro-3-O-acyl-5-hydroxyl-6-methyl-4H-pyran-4-one, preparation method and application in cigarette, to solve The problem that 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one in the prior art is poor in stability, easy to deteriorate and damaged, and cannot be used in cigarettes

Method used

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  • 2, 3-dihydro-3-O-acyl-5-hydroxy-6-methyl-4H-pyran-4-one, and preparation method and application thereof
  • 2, 3-dihydro-3-O-acyl-5-hydroxy-6-methyl-4H-pyran-4-one, and preparation method and application thereof
  • 2, 3-dihydro-3-O-acyl-5-hydroxy-6-methyl-4H-pyran-4-one, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] In a 50mL reaction flask, DDMP (1.44g, 10mmol) was dissolved in 20mL of anhydrous dichloromethane, and the catalyst 4-dimethylaminopyridine (DMAP) (0.06g, 0.5mmol), triethylamine (1.2g, 11mmol) were added successively ), BOC 2 O (2.3g, 10.5mmol), reacted at room temperature for 3h, evaporated the solvent, and the residue was subjected to silica gel column chromatography, eluting with petroleum ether / ethyl acetate=3 / 1 to obtain 2.0g of DDMP-5-BoC compound, the yield 95%.

[0031] DDMP-5-BoC compound (0.68g, 2.8mmol) was dissolved in 20mL of anhydrous dichloromethane, cooled to 0°C, triethylamine (0.36g, 3.6mmol), acetyl chloride (0.24g, 3.1mmol) were added successively, After adding, it was raised to room temperature for 4h, and the reaction solution was successively washed with saturated NaHCO 3 , washed with saturated NaCl, and the organic phase was washed with anhydrous NaCl 2 SO 4 After drying, 0.76 g of DDMP-5-BoC-3-acetate compound was obtained with a yield of ...

Embodiment 2

[0034] In a 50mL reaction flask, successively add DDMP (1.44g, 10mmol) dissolved in 20mL of anhydrous methanol, successively add triethylamine (1.2g, 11mmol), DMAP (0.06g, 0.5mmol), BOC 2 O (2.3g, 10.5mmol), reacted at room temperature for 3h, evaporated the solvent, and the residue was subjected to silica gel column chromatography, eluting with petroleum ether / ethyl acetate=3 / 1 to obtain 2.0g of DDMP-5-BoC compound, the yield 95%.

[0035] DDMP-5-BoC compound (0.6g, 2.8mmol) was dissolved in 20mL of anhydrous dichloromethane, cooled to 0°C, and triethylamine (0.36g, 3.6mmol) and phenylacetyl chloride (0.48g, 3.1mmol) were added successively , Add Bi rose to room temperature for 6h. The reaction solution was sequentially washed with saturated NaHCO 3 , washed with saturated NaCl, and the organic phase was washed with anhydrous NaCl 2 SO 4 After drying, 0.88 g of DDMP-5-BoC-3-benzoate compound was obtained with a yield of 90%.

[0036] DDMP-5-BoC-3-benzoate compound (0.35g...

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Abstract

The invention relates to 2, 3-dihydro-3-O-acyl-5-hydroxy-6-methyl-4H-pyran-4-one, a preparation method and application thereof, and the technical scheme is as follows that: DDMP is used as a raw material, and the 2, 3-dihydro-3-O-acyl-5-hydroxy-6-methyl-4-Hpyran-4-one is prepared by three steps of reaction of DDMP5-site hydroxyl acetylation protection, 3-site hydroxyl esterification and 5-site hydroxyl deacetylation protection. Compared with DDMP, the 3, 3-dihydro-3-O-acyl-5-hydroxyl-6-methyl-4-hpyran-4-one compound has good storage stability and perfuming stability, and when the 3, 3-dihydro-3-O-acyl-5-hydroxyl-6-methyl-4H-pyran-4-one compound is added into cigarettes, the effects of increasing the sweet feeling of the oral cavity and improving the aftertaste comfort of the DDMP are shown, the cigarette fragrance can be enriched, and the smoke permeability and fineness are improved, therefore, the method has potential application value.

Description

technical field [0001] The invention belongs to the technical field of flavor synthesis for tobacco, and specifically relates to 2,3-dihydro-3-O-acyl-5-hydroxyl-6-methyl-4H-pyran-4-one, its preparation method 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, and is one of the important signs that distinguish Chinese-style cigarettes from American-style, British-style, Japanese-style and other cigarettes. 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one belongs to the class of pyranolone compounds, which are commonly found in cigarette smoke, Maillard reaction products, sugar Cracking products and natural extracts; it has a significant positive correlation with the "sweetness" of smoke, which can significantly improve the sweetness of cigarette smoke, highlighting 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): C07D309/32A24B15/40A24B3/12
CPCC07D309/32A24B15/403A24B3/12
Inventor 王清福陈芝飞席高磊白冰付瑜锋刘强许克静徐永明马宇平
Owner CHINA TOBACCO HENAN IND
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