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Preparation method and application of pyrone flavor raw material capable of highlighting sweet taste characteristic of Chinese cigarettes

A technology for pyrone incense and cigarettes, which is applied in the field of tobacco flavor synthesis, can solve the problems of difficulty in realizing large-scale industrial production, low yield, and unused raw materials for tobacco flavor, and achieve potential application value and reaction yield Enhance and enrich the effect of smoke aroma

Active Publication Date: 2021-04-06
CHINA TOBACCO HENAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the current synthesis of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one mainly uses glucose and piperidine as raw materials, the yield is low, and it is difficult to realize large-scale Due to industrial production, it has not been used as a raw material for tobacco flavor

Method used

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  • Preparation method and application of pyrone flavor raw material capable of highlighting sweet taste characteristic of Chinese cigarettes
  • Preparation method and application of pyrone flavor raw material capable of highlighting sweet taste characteristic of Chinese cigarettes
  • Preparation method and application of pyrone flavor raw material capable of highlighting sweet taste characteristic of Chinese cigarettes

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] Preparation of maltol epoxide: In a 50 mL round bottom flask, add 1.26 g maltol (10 mmol), 0.58 g cobalt phthalocyanine (1.0 mmol), 0.23 g α, α, α-terpyridine (1.0 mmol) and 10 mL Acetonitrile, stirred at 25°C for 30 minutes until completely dissolved, then cooled the reaction system to 0°C, and added dropwise 0.68g of 50% H 2 o 2 aqueous solution (10mmol), reacted at 25°C for 2 hours, after the reaction was completed, 10mL of saturated Na 2 S 2 o 3 solution and saturated 10mL NaCl solution, extracted and separated to obtain the organic phase and washed with anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated under reduced pressure and purified by silica gel column chromatography to obtain 1.34 g of maltol epoxide with a yield of 94.3%.

[0021] The preparation of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one target compound: In a 100mL round bottom flask, add maltol epoxide (10mmol), 10mL tetrahydrofuran and 0.1g Pd / C, use a round-bottomed flask to...

Embodiment 2

[0023] Preparation of maltol epoxide: In a 50 mL round bottom flask, add 1.26 g maltol (10 mmol), 0.09 g cobalt hydroxide (1.0 mmol), 0.16 g 2,2'-bipyridine (1.0 mmol) and 10 mL THF was stirred at 25°C for 30 minutes until it was completely dissolved, then the reaction system was cooled to 0°C, and 0.68g of 50% H 2 o 2 Aqueous solution (10mmol), react at 25°C for 1 hour, after the reaction is completed, add 10mL saturated Na 2 S 2 o 3 solution and saturated 10mL NaCl solution, extracted and separated to obtain the organic phase and washed with anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated under reduced pressure and purified by silica gel column chromatography to obtain 1.29 g of maltol epoxide with a yield of 90.8%.

[0024] The preparation of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one target compound: In a 100mL round bottom flask, add maltol epoxide (10mmol), 10mL of acetonitrile and 0.1g of Raney nickel were replaced with nitrogen 3 times and h...

Embodiment 3

[0026] Preparation of maltol epoxide: In a 50 mL round bottom flask, add 1.26 g of maltol (10 mmol), 0.31 g of cobalt acetate (1.0 mmol), 0.18 g of 1,10-phenanthroline (1.0 mmol) and 10 mL of tetrahydrofuran , stirred at 25°C for 30 minutes until completely dissolved, then cooled the reaction system to 0°C, and added dropwise 0.68g of 50% H 2 o 2 Aqueous solution (10mmol), react at 25°C for 1 hour, after the reaction is completed, add 10mL saturated Na 2 S 2 o 3 solution and saturated 10mL NaCl solution, extracted and separated to obtain the organic phase and washed with anhydrous NaCl 2 SO 4 After drying, the solvent was evaporated under reduced pressure and purified by silica gel column chromatography to obtain 1.27 g of maltol epoxide with a yield of 89.4%.

[0027]The preparation of 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one target compound: In a 100mL round bottom flask, add maltol epoxide (10mmol), 10mL of dichloromethane and 0.1g of zinc powder, use a round...

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Abstract

The invention relates to a preparation method and application of a pyrone flavor raw material capable of highlighting the sweet taste characteristics of Chinese cigarettes. According to a technical scheme in the invention, maltol is used as a raw material and undergoes an olefin epoxidation reaction at first to obtain maltol epoxide, and then a hydrogenation reaction is carried out to obtain 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-pyran-4-one. Compared with reported literature, the method has the advantages that reaction yield is remarkably increased, and the total yield of two-step reactions is 85% or above. As the pyrone flavor raw material is added into a cigarette, cigarette fragrance can be enriched, the smoke permeability and fineness of the cigarette can be improved, aftertaste comfort can be improved, the sweet taste of the cigarette in the oral cavity can be improved, and the sweet taste characteristics of the Chinese cigarettes can be highlighted; and the pyrone flavor raw material has potential application value.

Description

technical field [0001] The invention belongs to the technical field of synthesis of flavorings for tobacco, and in particular relates to a raw material of pyrone aroma, 2,3-dihydro-3,5-dihydroxy-6-methyl-4H-2,3-dihydro-3,5-dihydroxy-6-methyl-4H- A preparation method of pyrone-4-one and its application in cigarettes as a raw material of pyrone aroma. Background technique [0002] Cigarette style characteristics are the core component of cigarette products and an important symbol that distinguishes a cigarette brand from other brands. The unique "sweet taste" of Chinese-style cigarettes is one of the important signs that distinguish them from American-style, British-style, and Japanese-style cigarettes. In order to highlight this feature, substances such as sugars, extracts, and Maillard reactants are usually used in Chinese cigarette flavoring; the reason why these substances can sweeten the smoke is mainly because they contain or crack to produce pyrone However, due to the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C11B9/00A24B3/12
CPCC11B9/008A24B3/12
Inventor 陈芝飞席高磊马宇平王清福赵志伟付瑜锋蔡莉莉赵旭刘强
Owner CHINA TOBACCO HENAN IND
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