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Preparation method and application of tobacco latent aroma monomer pyrazine-2-carboxylates

A technology of pyrazine and latent aroma, which is applied in the field of preparation of pyrazine-2-carboxylates, a latent aroma monomer for cigarettes, can solve the problems of poor thermal stability at high temperature and short fragrance retention time, and reduce irritation and miscellaneous Gas, simplify the post-treatment process, improve the effect of reaction yield

Active Publication Date: 2019-04-26
HUBEI CHINA TOBACCO IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Many excellent spices have limited their wide application due to their poor high temperature thermal stability, strong volatility, and short fragrance retention time.

Method used

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  • Preparation method and application of tobacco latent aroma monomer pyrazine-2-carboxylates
  • Preparation method and application of tobacco latent aroma monomer pyrazine-2-carboxylates
  • Preparation method and application of tobacco latent aroma monomer pyrazine-2-carboxylates

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The preparation method of pyrazine-2-carboxylic acid geraniol ester of tobacco flavor monomer:

[0027] Take 10mmol of geraniol and 10mmol of pyrazine-2-carboxylic acid dissolved in 100ml of dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (5mmol) and 1-ethyl-(3-dimethyl Aminopropyl) carbodiimide hydrochloride (EDCHCl) (11mmol), stirring at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate = 10:1, Rf = 0.5, ultraviolet 254nm color development), tracking reaction end. Add 50 mL of water to the organic phase to wash, separate the layers, then wash with 50 mL of saturated sodium chloride solution, separate the layers, dry the organic phase with anhydrous Na2SO4, and concentrate to obtain a crude product. Dissolve the crude product in 50 mL of dichloromethane, add 4 g of 100-200 mesh silica gel, spin dry the sample under reduced pressure, and use 80 g of 100-200 mesh silica gel chromatography to slowly elute with pet...

Embodiment 2

[0029] The preparation method of pyrazine-2-carboxylic acid geraniol ester of tobacco flavor monomer:

[0030] Take 10mmol of geraniol and 10.5mmol of pyrazine-2-carboxylic acid dissolved in 100ml of dry dichloromethane, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (4mmol) and 1-ethyl-(3-dichloromethane Methylaminopropyl) carbodiimide hydrochloride (EDCHCl) (11 mmol), stirred at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate = 10:1, Rf = 0.5, ultraviolet 254nm color development), Track reaction endpoints. Add 50 mL of water to the organic phase to wash, separate the layers, then wash with 50 mL of saturated sodium chloride solution, separate the layers, dry the organic phase with anhydrous Na2SO4, and concentrate to obtain a crude product. Dissolve the crude product in 50 mL of dichloromethane, add 4 g of 100-200 mesh silica gel, spin dry the sample under reduced pressure, and use 80 g of 100-200 mesh silica gel chromatography to slo...

Embodiment 3

[0032] The preparation method of tobacco fragrance monomer pyrazine-2-formic acid-β-ionyl ester:

[0033] In a three-necked flask, add weighed 20mmol β-ionol and 20mmol pyrazine-2-carboxylic acid dissolved in 200ml dry methylene chloride, after stirring for 10min, add 4-dimethylaminopyridine (DMAP) (9mmol) and 1- Ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) (22mmol), stirring at room temperature, TLC monitoring reaction (petroleum ether: ethyl acetate = 10:1, Rf =0.5, ultraviolet 254nm color), follow the reaction to the end point. Add 100 mL of pure water to the organic phase to wash, separate the layers, then wash with 100 mL of saturated sodium chloride solution, separate the layers, dry the organic phase with anhydrous Na2SO4, and concentrate the crude product. The crude product was dissolved in 10 mL of dichloromethane, 7 g of 100-200 mesh silica gel was added, the sample was spin-dried under reduced pressure, and the sample was separated by 100 g of ...

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Abstract

The invention relates to a preparation method of a tobacco precursor-aroma monomer pyrazine-2-formate. The method includes the steps of: dissolving pyrazine-2-formic acid and beta-ionol in dry dichloromethane, performing stirring for 10min-30min, adding 4-dimethylamino pyridine and 1-ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride, conducting stirring at room temperature for 4-12h, carrying out TLC monitoring reaction, and tracking the reaction end point, adding water into an organic phase for washing, separating liquid, then using a saturated sodium chloride solution to perform washing, and separating liquid, drying the organic phase with anhydrous Na2SO4, and performing concentration to obtain a crude product, and carrying out column chromatographic separation so as to obtain the product. Compared with geraniol and beta-ionol precursors, the pyrazine-2-geranyl formate and pyrazine-2-formic acid-beta-ionol ester prepared by the method provided by the invention can significantly increase the adding amount in cigarettes, are applied as a tobacco fragrance enhancer in cigarettes, can reduce cigarette irritation and miscellaneous gas, and can improve the mellow sense and comfort of cigarette smoke.

Description

technical field [0001] The invention relates to the fields of flavors and fragrances and tobacco processing, in particular to a preparation method and application of tobacco latent aroma monomer pyrazine-2-carboxylates. Background technique [0002] Many excellent spices have limited their wide application due to their poor high-temperature thermal stability, strong volatility, and short fragrance retention time. Latent aroma substances are substances with large relative molecular weight and high boiling point, which have little or no aroma, but can release aroma and aroma substances through chemical hydrolysis, enzymatic hydrolysis, microbial action, pyrolysis, photolysis and other ways. compound. Because of its good safety, it is included in the category of natural spices in the world, and it is very effective to use it to prepare certain flavor food flavors. Unlike volatile and semi-volatile aroma substances, latent aroma compounds will not cause significant changes in ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D241/44A24B3/12A24B15/38
CPCA24B3/12A24B15/38C07D241/44
Inventor 董爱君熊国玺刘华臣赵国豪潘婷婷
Owner HUBEI CHINA TOBACCO IND