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Ambergris lactone based precursor-aroma compound as well as preparation method and application thereof

A technology for ambroxolide and compound, which is 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 achieves rich variety, high volatility, high smell fragrant effect

Active Publication Date: 2015-11-18
CHINA TOBACCO SICHUAN IND CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] 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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  • Ambergris lactone based precursor-aroma compound as well as preparation method and application thereof
  • Ambergris lactone based precursor-aroma compound as well as preparation method and application thereof
  • Ambergris lactone based precursor-aroma compound as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] 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 (500 mg, 2.0 mmol) was added dropwise at -60° C, and the reaction system was stirred for 40 minutes, then 3-acetylpyridine (242.2 mg, 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 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-2A (a mixture of two diastereoisomers CYL-2-QX-2A-a and CYL-2-QX-2A-b), the yield was 68.0%.

[0042] Wherein the structural representa...

Embodiment 2

[0052] 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 (500 mg, 2.0 mmol) was added dropwise at -60° C, and the reaction system was stirred for 40 minutes, then 2-acetylpyridine (242.2 mg, 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 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-2B, the yield is 63.0%.

[0053] The structure of CYL-2-QX-2B is characterized as follows:

[0054] 1 HNMR (CDCl 3 ):δ,ppm0.32(t,...

Embodiment 3

[0058] 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, the reaction system was stirred for 40min, and then 4-acetylpyridine (242.2mg, 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 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-2C, yield 61.0%.

[0059] ESIMS(positiveionmode)(rel.int.)m / z:372([M+H] + ,100).

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Abstract

The invention discloses an ambergris lactone based precursor-aroma compound as well as a preparation method and an application thereof. The preparation method comprises the following steps: 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 pyridine 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 which can release aroma during burning or heating. A very good model is provided for application of small fragrance molecules with high volatility and lower threshold value, meanwhile, the variety of the ambergris fragrance can be increased and enriched, the application ranges of the ambergris raw materials and acyl pyridine are broadened, and the defects of the ambergris lactone and acyl pyridine can be overcome.

Description

technical field [0001] Embodiments of the present invention relate to the field of tobacco flavors, more specifically, embodiments of the present invention relate to novel latent aroma compounds based on the covalent linkage of ambroxolactone and roasted aroma acylpyridine and their synthesis and flavoring in cigarettes in the application. 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 whales, resembling stones, which are ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06A24B15/30
CPCA24B15/406C07D405/06
Inventor 陶飞燕杨文敏冯广林戴亚周志刚张艇邱光明刘如灿周胜王耀李朝荣丁为
Owner CHINA TOBACCO SICHUAN IND CO LTD
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