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Perillyl alcohol ambradiol carbonate precursor aroma substance as well as preparation method and application of perillyl alcohol ambradiol carbonate precursor aroma substance

A technology for perillyl alcohol and ambergris, which is applied in the field of tobacco flavors, can solve the problems of inability to use tobacco formulations well, volatilization during processing and storage, loss of characteristic aroma and the like, and achieves low cost, small molecular weight, and easy operation. Effect

Pending Publication Date: 2021-10-08
SICHUAN SANLIAN NEW MATERIAL CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is also used in tobacco flavors, used in tobacco flavors, can enhance the fragrance of flowers, coordinate with the aroma of cigarettes, raise the smoke, improve the taste, but it is not long-lasting, and it is easy to volatilize and lose its characteristics during processing and storage Aroma, does not work well in tobacco formulations

Method used

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  • Perillyl alcohol ambradiol carbonate precursor aroma substance as well as preparation method and application of perillyl alcohol ambradiol carbonate precursor aroma substance
  • Perillyl alcohol ambradiol carbonate precursor aroma substance as well as preparation method and application of perillyl alcohol ambradiol carbonate precursor aroma substance
  • Perillyl alcohol ambradiol carbonate precursor aroma substance as well as preparation method and application of perillyl alcohol ambradiol carbonate precursor aroma substance

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Dissolve 1 mmol of perillyl alcohol and 3 mmol of 1,1'-carbonyldiimidazole in 20 mL of dry tetrahydrofuran, heat to 23 °C and stir for 3 h. TLC monitors perillyl alcohol and the reaction product of perillyl alcohol and 1,1'-carbonyldiimidazole, tracks the reaction end point, adds 25mL dichloromethane and 2×15mL deionized water to the organic phase for washing (2×15mL, means deionized Wash twice with deionized water (15 mL each time), separate the layers, dehydrate the organic phase with anhydrous magnesium sulfate, and concentrate to obtain Liquid A.

[0029] Add 1.2 mmol of Ambroxol and 20 mL of N,N-dimethylformamide to the above liquid A, heat to 90°C and stir for 6 hours. Cool down to room temperature after the reaction, add 50mL deionized water and 50mL dichloromethane to the organic phase, separate the liquids, wash the organic phase with 15mL deionized water and 15mL saturated NaCl solution successively, dewater the organic phase with anhydrous magnesium sulfate, ...

Embodiment 2

[0031] Dissolve 1 mmol of perillyl alcohol and 2 mmol of 1,1'-carbonyldiimidazole in 20 mL of dry tetrahydrofuran, heat to 25 °C and stir for 4 h. TLC monitors perillyl alcohol and the reaction product of perillyl alcohol and 1,1'-carbonyldiimidazole, tracks the reaction end point, adds 25mL dichloromethane and 2×15mL deionized water to the organic phase for washing, separates the liquid, and uses it for the organic phase Remove water with anhydrous magnesium sulfate and concentrate to obtain liquid A.

[0032] Add 1.5 mmol of Ambroxol and 20 mL of N,N-dimethylformamide to the above liquid A, heat to 60°C and stir for 6 hours. Cool down to room temperature after the reaction, add 50mL deionized water and 50mL dichloromethane to the organic phase, separate the liquids, wash the organic phase with 15mL deionized water and 15mL saturated NaCl solution successively, dewater the organic phase with anhydrous magnesium sulfate, concentrate The oily liquid is obtained, and then separ...

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Abstract

The invention discloses a perillyl alcohol ambradiol carbonate precursor aroma substance and a preparation method and application thereof. The preparation method comprises the steps of dissolving perillyl alcohol and 1,1'-carbonyldiimidazole in dry tetrahydrofuran, and conducting heating and stirring for a reaction; tracking the reaction endpoint by TLC, after the reaction is completed, adding dichloromethane and deionized water into the organic phase, carrying out liquid separation, removing water from the organic phase by using anhydrous magnesium sulfate, and conducting concentrating to obtain a liquid A; adding ambradiol and N,N-dimethylformamide into the liquid A, conducting heating and stirring to react, and conducting cooling to room temperature after the reaction; and adding deionized water and dichloromethane into the organic phase, conducting liquid separation, washing the organic phase with deionized water and a saturated NaCl solution in sequence, dewatering the organic phase with anhydrous magnesium sulfate, conducting concentrating to obtain oily liquid, and then conducting column chromatography separation and purification to obtain the perillyl alcohol ambradiol carbonate precursor aroma substance. According to the invention, a good model is provided for the application of perfume micromolecules with high volatility and smaller threshold value, the ambergris note and the flower note can be increased and enriched, and the application range of the ambergris raw material and the perilla alcohol is widened.

Description

technical field [0001] The present invention relates to the field of tobacco spices, more specifically, the present invention and a latent aroma substance with ambergris and floral notes based on ambroxol and perillyl alcohol connected by an ester bond and its application in cigarette flavoring. Background technique [0002] Ambergris is a very popular blending spice in the market. It is also known as the four major animal spices together with musk, civet, and kelp. Ambrox ((-)-Ambrox) is a precious raw material of ambergris, which has a strong and special aroma of ambergris. Described as having a "subtle and velvety" ambergris aroma, with an "ambergris effect", it is the soul of ambergris, an excellent fixative, and is the best among all synthetic ambergris fragrances The highest kind. It has been used as a substitute for natural ambergris in high-end perfumes and cosmetic essences. Because it is non-irritating to the human body and has no allergic reactions to animals, i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/96C07C68/00C07C68/06A24B3/12
CPCC07C69/96C07C68/00C07C68/06A24B3/12C07C2602/28C07C2602/10
Inventor 陶飞燕丁玉王益明崔韬杨柳天壹常丹丹朱笛恺吴雷邓永张艇杨庆国郭刚
Owner SICHUAN SANLIAN NEW MATERIAL CO LTD
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