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Latent aroma compound with sweet and nutty aroma and its preparation method and application

A compound and latent aroma technology, applied in the field of tobacco flavor, can solve the problems of inability to use tobacco formulations well, unstable cigarette quality, poor heat-resistant processability, etc., and achieve the effects of rich varieties, small molecular weight, and high volatility

Active Publication Date: 2017-12-12
CHINA TOBACCO SICHUAN IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] However, these two types of molecules have high volatility and low threshold, so their heat resistance is poor, so that they cannot be well used in tobacco formulations, and they are easily lost during processing. Cigarette quality is unstable due to the volatilization of the agent

Method used

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  • Latent aroma compound with sweet and nutty aroma and its preparation method and application
  • Latent aroma compound with sweet and nutty aroma and its preparation method and application
  • Latent aroma compound with sweet and nutty aroma and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Add 8ml of anhydrous diethyl ether and 0.311ml (2.2mmol) of diisopropylamine in a 50ml round bottom flask, cool the solution to -60°C, then drop BuLi (2.2mmol) in 2.5N n-hexane solution into the upper reaction system, Raise the reaction system to 0°C and stir for 15min, then add the ether solution of norambrolide (500mg, 2.0mmol) dropwise at -60°C, continue to stir the reaction system for 40min, then add 2-acetylthiazole (254.3mg, 2.0 mmol) ether solution was added dropwise to the reaction system. Stir the reaction system at this temperature for 50 min, quench the reaction with water, separate the organic layer, wash with saturated salt, dry over anhydrous sodium sulfate, filter, distill off the solvent under reduced pressure, and separate the residue by silica gel column chromatography to obtain CYL-2- QX-3A, the yield is 60.0%.

[0041] 1 HNMR (CDCl 3 ):δ, ppm 0.59(td, J=12.4Hz, J=3.6Hz 1H), 0.74(s,3H), 0.83(s,3H), 0.88(s,3H), 0.89~0.93(m,1H) ,1.00~1.05(m,3H),1.24...

Embodiment 2

[0045] Add 8ml of anhydrous diethyl ether and 0.311ml (2.2mmol) of diisopropylamine in a 50ml round bottom flask, cool the solution to -60°C, then drop BuLi (2.2mmol) in 2.5N n-hexane solution into the upper reaction system, The reaction system was raised to 0°C and stirred for 15min, then a solution of norbroxolide (500mg, 2.0mmol) in ether was added dropwise at -60°C, and the reaction system was stirred for 40min, then 2,4-dimethyl-5 - Ether solution of acetylthiazole (310.4mg, 2.0mmol) was added dropwise to the above reaction system. Stir the reaction system at this temperature for 50 min, quench the reaction with water, separate the organic layer, wash with saturated brine, dry over anhydrous sodium sulfate, filter, distill off the solvent under reduced pressure, and separate the residue by silica gel column chromatography to obtain CYL-2- QX-3B, yield 57.0%.

[0046] ESI-MS(positive ion mode)(rel.int.)m / z:406([M+H] + ,100).

Embodiment 3

[0048] Add 8ml of anhydrous diethyl ether and 0.311ml (2.2mmol) of diisopropylamine in a 50ml round bottom flask, cool the solution to -60°C, then drop BuLi (2.2mmol) in 2.5N n-hexane solution into the upper reaction system, The reaction system was raised to 0°C and stirred for 15 minutes, then a diethyl ether solution of norambrolide (500mg, 2.0mmol) was added dropwise at -60°C, and the reaction system was stirred for 40 minutes, then 4-acetylthiazole (254.3.4mg, 2.0 mmol) of ether solution was added dropwise to the reaction system. Stir the reaction system at this temperature for 50 min, quench the reaction with water, separate the organic layer, wash with saturated salt, dry over anhydrous sodium sulfate, filter, distill off the solvent under reduced pressure, and separate the residue by silica gel column chromatography to obtain CYL-2- QX-3C, yield 55.0%.

[0049] ESI-MS(positive ion mode)(rel.int.)m / z:378([M+H] + ,100).

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Abstract

The invention discloses a precursor-aroma compound having sweet aroma and nut aroma as well as a preparation method and an application of the precursor-aroma compound. According to the method, ambergris lactone is dissolved in sufficient quantity of a solvent, alkali is added at the temperature ranging from subzero 78 DEG C to 50 DEG C, the mixture is stirred and reacts for more than 10 min, then acyl thiazole is added, the mixture is stirred at the temperature ranging from subzero 78 DEG C to 50 DEG C and reacts for more than 30 min, a quenching reaction is performed, and finally, the target precursor-aroma compound is obtained through postprocessing, separation and purification and added in the ratio of 0.00001%-10% by weight to a product such as tobacco which can release aroma during burning or heating. a very good model for application of small fragrance molecules with high volatility and lower threshold value is provided through design, preparation and the application of the precursor-aroma compound, meanwhile, the variety of the ambergris fragrance can be increased and enriched, the application ranges of the ambergris raw materials and acyl thiazole are broadened, and the defects of the ambergris lactone and acyl thiazole can be overcome.

Description

technical field [0001] Embodiments of the present invention relate to the field of tobacco flavors, and more specifically, embodiments of the present invention relate to novel latent aroma compounds with sweet and nutty flavors based on the covalent linking of ambroxolactone and acylthiazole with nutty flavor Its preparation method and its application in cigarette flavoring. Background technique [0002] Ambergris is one of the most valuable animal spices. It is also known as the four major animal spices along with musk, civet, and hyacinth. Because of its complex and balanced fragrance and long-lasting fragrance-fixing ability, it has medical effects such as nourishing and nourishing the body, strengthening yang, anti-inflammation, and labor pains, and has been valued by people since ancient times. Ambergris has now been made into tinctures, mainly used to prepare high-end and expensive perfumes. [0003] Ambergris is a secretion from the stomach and intestines of sperm w...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/06A24B15/36
CPCA24B15/365C07D417/06
Inventor 陶飞燕杨文敏冯广林戴亚李朝荣丁为王耀周胜周志刚邱光明刘如灿张艇
Owner CHINA TOBACCO SICHUAN IND CO LTD
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