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Latent fragrance compound based on ambroxolactone and its preparation method and application

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., so as to highlight the style of cigarettes and improve the smoking quality. , the effect of high stability

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

[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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  • Latent fragrance compound based on ambroxolactone and its preparation method and application
  • Latent fragrance compound based on ambroxolactone and its preparation method and application
  • Latent fragrance compound based on ambroxolactone and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] In a 50ml round-bottomed flask, 8ml of anhydrous ether and 0.311ml (2.2mmol) of diisopropylamine were added, the solution was cooled to -60°C, and then BuLi (2.2mmol) of 2.5N n-hexane solution was added dropwise to the reaction system, The reaction system was raised to 0°C and stirred for 15min, then the ether solution of ambroxolide (500mg, 2.0mmol) was added dropwise at -60°C, the reaction system was continued to stir for 40min, and then 3-acetylpyridine (242.2mg, 2.0 mmol) was added dropwise. mmol) in ether was added dropwise to the reaction system. The reaction system was stirred at this temperature for 50 min, quenched with water, the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, distilled under reduced pressure to remove the solvent, and the residue was separated by silica gel column chromatography to obtain CYL- 2-QX-2A (a mixture of two diastereomers CYL-2-QX-2A-a and CYL-2-QX-2A-b), 68.0% yield.

[004...

Embodiment 2

[0052] In a 50ml round-bottomed flask, 8ml of anhydrous ether and 0.311ml (2.2mmol) of diisopropylamine were added, the solution was cooled to -60°C, and then BuLi (2.2mmol) of 2.5N n-hexane solution was added dropwise to the reaction system, The reaction system was raised to 0 °C and stirred for 15 min, and then a solution of ambroxolide (500 mg, 2.0 mmol) in ether was added dropwise at -60 °C, the reaction system was continued to stir for 40 min, and then 2-acetylpyridine (242.2 mg, 2.0 mmol) was added dropwise. 2.0 mmol) ether solution was added dropwise to the reaction system. The reaction system was stirred at this temperature for 50 min, quenched with water, the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, distilled under reduced pressure to remove the solvent, and the residue was separated by silica gel column chromatography to obtain CYL- 2-QX-2B, yield 63.0%.

[0053] Among them, the structure of CYL-2-QX-2B...

Embodiment 3

[0058] In a 50ml round-bottomed flask, 8ml of anhydrous ether and 0.311ml (2.2mmol) of diisopropylamine were added, the solution was cooled to -60°C, and then BuLi (2.2mmol) of 2.5N n-hexane solution was added dropwise to the reaction system, The reaction system was raised to 0°C and stirred for 15min, then the ether solution of ambroxolide (500mg, 2.0mmol) was added dropwise at -60°C, the reaction system was continued to stir for 40min, and then 4-acetylpyridine (242.2mg, 2.0 mmol) was added dropwise. mmol) in ether was added dropwise to the reaction system. The reaction system was stirred at this temperature for 50 min, quenched with water, the organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, distilled under reduced pressure to remove the solvent, and the residue was separated by silica gel column chromatography to obtain CYL-2- QX-2C, yield 61.0%.

[0059] ESI MS(positive ion mode)(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] The embodiments of the present invention relate to the field of tobacco flavors, and more particularly, the embodiments of the present invention relate to novel latent flavor compounds based on ambroxolide and roasted aromayl pyridine covalently linked, and their synthesis and flavoring in cigarettes applications in . Background technique [0002] Ambergris is one of the most valuable animal spices, and it is known as the four major animal spices together with musk, civet, and sea incense. Because of its complex and balanced fragrance and lasting fragrance-fixing ability, it has medical effects such as nourishing and nourishing, aphrodisiac, anti-inflammatory, labor pain, etc., and has been valued by people since ancient times. Ambergris has now been made into tinctures, mainly used to formulate high-end luxury perfumes. [0003] Ambergris is the gastrointestinal secretions of sperm whales, similar to stones, which are vomited or excreted on the sea ...

Claims

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Application Information

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Patent Type & Authority Patents(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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