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Menthol formate precursor-aroma compound as well as preparation method and application thereof

A technology of alcohol formate and compounds, which is applied in the field of menthyl formate latent aroma compounds, can solve the problems of mint flavor loss, poor stability, and high volatility, and achieve the effects of high volatility, stable properties, and increased types

Pending Publication Date: 2021-12-17
CHINA TOBACCO SICHUAN IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although solving the problem of mint flavor loss in menthol cigarettes is the original intention of using latent aroma substances in cigarettes, the menthol ester compounds synthesized in the prior art have problems such as high volatility and poor stability. Therefore, the field of tobacco flavors and fragrances is stable in preparation properties. There is still an urgent need for menthyl esters that can release fragrance components evenly

Method used

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  • Menthol formate precursor-aroma compound as well as preparation method and application thereof
  • Menthol formate precursor-aroma compound as well as preparation method and application thereof
  • Menthol formate precursor-aroma compound as well as preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Methol (0.75 g, 4.81 mmol) was added (no water) dichloromethane (10 mL) to dissolve, and three light gas (0.58 g, 1.77 mmol, water-water dichloromethane dissolved) was stirred, and pyridine (0.4 ml, 4.91) mmol). 50-60 ° C was stirred for 5 h, and the reduced pressure was concentrated (about 1.75 g, about 4.8 mmol) was added, and dichloromethane was dissolved, and the fragrant of 4 mmol was added, and the catalytic amount of triethylamine was added, stirred even about 20 min. After slow adding to the above solution, the reaction overnight, the TLC point plate was almost reacted. The reaction system was dried, the water and ethyl acetate were added, and the organic phase was retained, and the water was washed twice. The product LY1 was isolated by petroleum ether: ethyl acetate = 20: 1-15: 1 column chromatography obtained by 78% yield.

[0038] Test results Figure 1-3 As shown, the structure characterization is as follows:

[0039] 1 HNMR (400MHz, CDCL 3 : δ, PPM 0.85 (D, 3H)...

Embodiment 2

[0041]Methol (0.75 g, 4.81 mmol) was added (no water) dichloromethane (10 mL) to dissolve, and three light gas (0.58 g, 1.77 mmol, water-water dichloromethane dissolved) was stirred, and pyridine (0.4 ml, 4.91) mmol). 50-60 ° C was stirred for 5 h, concentrated under reduced pressure (lysolated solid 1.75 g, about 4.8 mmol), dissolved in dichloromethane, and additionally ethylcetin 4 mmol, add catalytic amount of triethylamine, stir well After about 20 min, slowly added to the above solution, and the reaction was overnight. The reaction system was dried, the water and ethyl acetate were added, and the organic phase was retained, and the water was washed twice. The product Ly2 was isolated by petroleum ether: ethyl acetate = 20: 1-15: 1 column chromatography was isolated from 76% yield.

[0042] Test results Figure 4-6 As shown, the structure characterization is as follows:

[0043] 1 HNMR (400MHz, CDCL 3 : δ, PPM 0.85 (D, 3H), 0.95 (D, 6H), 1.03 ~ 1.46 (m, 3H), 1.42 ~ 1.46 (M, 3H)...

Embodiment 3

[0045] Methol (0.75 g, 4.81 mmol) was added (no water) dichloromethane (10 mL) to dissolve, and three light gas (0.58 g, 1.77 mmol, water-water dichloromethane dissolved) was stirred, and pyridine (0.4 ml, 4.91) mmol). 50-60 ° C for 5 h, concentrated under reduced pressure (about 1.75 g, about 4.8 mmol), and dichloromethane dissolved, and maltol 4mmol, add catalytic amount of triethylamine, stir evenly about 20 minutes. Added to the above solution, the reaction overnight. The reaction system was dried, the water and ethyl acetate were added, and the organic phase was retained, and the water was washed twice. The product LY4 was isolated by petroleum ether: ethyl acetate = 20: 1-15: 1 column chromatography was obtained from the product LY4, and the yield was 72%.

[0046] Test results Figure 7-9 As shown, the structure characterization is as follows:

[0047] 1 HNMR (400MHz, CDCL 3 : δ, PPM 0.85 (D, 3H), 0.94 (D, 6H), 1.02 ~ 1.54 (m, 2H), 1.68 ~ 1.73 (m, 2H), 2.03 ~ 2.10 ( M, 1H), ...

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PUM

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Abstract

The invention discloses a menthol formate precursor-aroma compound as well as a preparation method and application thereof. The preparation method comprises the steps: dissolving menthol in a sufficient amount of a solvent, adding triphosgene, stirring for 1 min or more, adding pyridine, carrying out a stirring reaction for 2 h or more at a temperature of 50-60 DEG C, carrying out vacuum concentration, dissolving with a solvent, slowly adding the obtained solution into aromatic phenol which is mixed and stirred with a catalyst for 10 min or more, reacting for 8 h or more, then spin-drying the reaction system, and finally carrying out post-treatment, separation and purification to obtain the target menthol formate precursor-aroma compound. The precursor-aroma compound disclosed by the invention has the characteristics of stable property in a normal-temperature environment and capability of uniformly releasing aroma under a heating condition, meanwhile, the variety of menthol aroma materials can be increased and enriched, the application range of menthol aroma raw materials and aromatic phenol can be widened, and the defects, such as high volatility, low threshold, heavy smell and easy loss during processing, of menthol and aromatic phenol can be overcome.

Description

Technical field [0001] The present invention relates to the technical field of tobacco flavor, and more particularly to a menthol carboxylate, preparation method and use. Background technique [0002] Mint, also known as menthol, with cool mint, cool taste, commonly used to formulate cigarette cooling agents, with flue gas transition, freshness, stunning, and complicated. Aromatic phenolic compounds are commonly used in cigarettes. Among them, the vanosin, with sweet fragrance, smelt, like Xiangliang bean characteristics, the aroma is lasting, it can increase the sweet milk, often used to formulate milk, sweet fragrant rhyme, with flavor, have improved smoke The fullness and concentration of air is reduced, the impurities and stimulus, make the smoke soft, and the lifeline is clean. Ethyl fraranges, aroma is similar to withcellin, but the aroma is more strong, the aroma strength is 3-4 times the vanillin, showing strong, sweet, similar vanilla, often used to formulate milk, Sweet...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/96C07C68/02C07D309/40A24B3/12
CPCC07C69/96C07C68/02C07D309/40A24B3/12C07C2601/14
Inventor 朱笛恺陶飞燕丁玉杨柳天壹常丹丹王益明崔韬张学建吴雷潘凌郭彦旭郭刚张艇申屠洪钎
Owner CHINA TOBACCO SICHUAN IND CO LTD
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