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Aromatic phenolic ester precursor-aroma compound as well as preparation method and application thereof

A technology for aromatic phenolic esters and compounds, which is applied in the direction of condensation preparation of carbonyl compounds, preparation of tobacco, essential oils/spice, etc., can solve the problems of affecting the quality stability, unstable content and high volatility of tobacco products, and achieves rich variety, widen Scope of application, effect of high volatility

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

[0003] However, the above-mentioned molecules have the characteristics of high volatility and low threshold value, and their direct application in tobacco formulations will bring the disadvantages of easy volatility and unstable content, which will affect the quality stability of tobacco products

Method used

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  • Aromatic phenolic ester precursor-aroma compound as well as preparation method and application thereof
  • Aromatic phenolic ester precursor-aroma compound as well as preparation method and application thereof
  • Aromatic phenolic ester precursor-aroma compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Add 15ml of dichloromethane and 0.8ml of triethylamine to 5mmol of vanillin, and stir in an ice bath for 10 minutes; dissolve 5mmol of acid chloride in 5ml of dichloromethane, slowly drop into the vanillin solution, and stir at 25°C for 8h. Add 200ml of dichloromethane to the reaction product, wash with 1M dilute hydrochloric acid three times, 50ml each time, and then wash once with 50ml of saturated brine, concentrate in vacuo to remove solvent, and use petroleum ether: ethyl acetate = 20:1-15:1 column chromatography The product LSD8 was isolated with a yield of 76%.

[0040] Test results such as Figure 1-3 As shown, wherein the structural representation is as follows:

[0041] LSD-08: 1HNMR (400MHz, CDCl3): δ, ppm 0.88(t, 3H), 1.26~1.43(m, 16H), 1.73~1.80(m, 2H), 2.6(t, 2H), 3.89(s, 3H),7.21(d,1H),7.46~7.49(m,2H),9.95(s,1H); 13CNMR(100MHz,CDCl3):δ,ppm 191.1,171.2,152.0,145.1,135.1,124.8,123.4, 110.8, 56.0, 34.0, 31.9, 29.6, 29.5, 29.3, 29.0, 24.9, 22.7; ESI-MS (m / ...

Embodiment 2

[0043]Add 15ml of dichloromethane and 0.8ml of triethylamine to 5mmol of ethyl vanillin, and stir in an ice bath for 10 minutes; dissolve 5mmol of tetradecanoyl chloride in 5ml of dichloromethane, and slowly add it dropwise to the vanillin solution at 25°C Under stirring for 8h. Add 200ml of dichloromethane to the reaction product, wash with 1M dilute hydrochloric acid three times, 50ml each time, and then wash once with 50ml of saturated brine, concentrate in vacuo to remove the solvent, and use petroleum ether: ethyl acetate = 20:1-15:1 column chromatography The product LSD13 was isolated in 89% yield.

[0044] Test results such as Figure 4-6 As shown, wherein the structural representation is as follows:

[0045] LSD-13: 1HNMR (400MHz, CDCl3): δ, ppm 0.88(t, 3H), 1.26~1.36(m, 18H), 1.40~1.46(m, 5H), 1.74~1.81(m, 2H), 2.59( t, 2H), 4.13 (dd, 2H), 7.20 (d, 1H), 7.44~7.47 (m, 2H), 9.93 (s, 1H); 13CNMR (100MHz, CDCl3): δ, ppm 191.1, 171.2, 151.4 ,145.3,135.1,124.6,123.4,111...

Embodiment 3

[0047] Add 15ml of dichloromethane and 0.8ml of triethylamine to 5mmol of maltol, and stir in an ice bath for 10 minutes; dissolve 5mmol of oleoyl chloride in 5ml of dichloromethane, slowly drop into the vanillin solution, and stir at 25°C for 8h. Add 200ml of dichloromethane to the reaction product, wash with 1M dilute hydrochloric acid three times, 50ml each time, and then wash once with 50ml of saturated brine, concentrate in vacuo to remove the solvent, and use petroleum ether: ethyl acetate = 20:1-15:1 column chromatography The product LSD18 was isolated with a yield of 82%.

[0048] Test results such as Figure 7-9 As shown, wherein the structural representation is as follows:

[0049] LSD-18: 1HNMR (400MHz, CDCl3): δ, ppm 0.88(t, 3H), 1.23~1.43(m, 20H), 1.72~1.77(m, 2H), 1.96~2.06(m, 5H), 2.25( s,3H),2.60(t,2H),4.12(q,1H),5.33~5.38(m,2H),6.39(d,2H),7.67(d,1H); 13CNMR(100MHz,CDCl3):δ ESI- MS(m / z):399.2492[M+Na]+

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Abstract

The invention discloses an aromatic phenolic ester precursor-aroma compound as well as preparation method and application thereof. The preparation method comprises the steps: stirring and dissolving aromatic phenol and a catalyst in a sufficient amount of solvent at the temperature of -10 DEG C-10 DEG C, slowly dropwise adding acyl chloride dissolved in the sufficient amount of solvent, and stirring at the temperature of 0 DEG C-50 DEG C for 6 hours or more; and finally, carrying out post-treatment separation and purification to obtain the target aromatic phenolic ester 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 of aromatic phenol and acid compounds under a heating condition, meanwhile, the variety of aromatic phenol spices can be increased and enriched, the application range of aromatic phenol aroma raw materials and acyl chloride can be widened, and the defects, such as high volatility, small threshold, heavy smell and easy loss during processing, of aromatic phenol and acyl chloride can be overcome.

Description

technical field [0001] The invention relates to the technical field of tobacco essence, in particular to an aromatic phenol ester latent aroma compound, a preparation method and an application. Background technique [0002] Aromatic phenolic compounds are widely used in tobacco flavors. Among them, vanillin has a sweet, bean, and milky aroma, which is similar to the characteristic smell of vanilla beans. It has a long-lasting aroma and can increase the sweetness of milk. Improve the fullness and concentration of gas, reduce miscellaneous gas and irritation, make the smoke soft and clean aftertaste. Ethyl vanillin, the aroma is similar to vanillin, but the aroma is stronger, the aroma intensity is 3-4 times that of vanillin, showing a strong, sweet, vanilla-like smell, often used to prepare milky, Sweet and fragrant tobacco flavor, which can increase the sweetness of milk, enhance the richness of tobacco aroma and smoke concentration, and soften the smoke. Eugenol, with mi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D309/38C07C49/86C07C49/84C07C45/45A24B3/12C11B9/00
CPCC07D309/38C07C49/86C07C49/84A24B3/12C11B9/008C11B9/0061A24B15/301A24D1/002A24B15/403
Inventor 陶飞燕朱笛恺丁玉崔韬邓发达杨柳天壹常丹丹王益明杨涓张学建丁为吴雷宋光富王耀杨军申屠洪钎朱宇
Owner CHINA TOBACCO SICHUAN IND CO LTD
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