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Latent aroma compound with sweet and roasted 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 poor use of tobacco formula, unstable quality of cigarettes, poor heat-resistant processability, etc., and achieve the effect of rich variety, small molecular weight, and heavy smell

Active Publication Date: 2018-08-14
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 aroma compound with sweet and roasted aroma and its preparation method and application
  • Latent aroma compound with sweet and roasted aroma and its preparation method and application
  • Latent aroma compound with sweet and roasted aroma and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] 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 ambroxolide (500 mg, 2.0 mmol) was added dropwise at -60° C, and the reaction system was stirred for 40 minutes, then 2-acetylpyrazine (244.2 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-4A (mixture of two diastereoisomers CYL-2-QX-4A-a and CYL-2-QX-4A-b), yield 61.0%, structure of its diastereomers Characterized as fo...

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 ambroxolide (500 mg, 2.0 mmol) was added dropwise at -60° C, and the reaction system was stirred for 40 minutes, and then 3-methyl-2-acetylpyrrolide was added A diethyl ether solution of oxazine (273.3mg, 2.0mmol) 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-4B, yield 59.0%.

[0053] Structural characterization of CYL-2-QX-4B:

[0054] 1 HNMR (CDCl...

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 40 minutes, and then 5-methoxy-2-acetyl Ether solution of pyrazine (304.3 mg, 2.0 mmol) 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-4C, yield 55.0%.

[0059] ESI-MS(positive ion mode)(rel.int.)m / z:403([M+H] + ,100).

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PUM

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Abstract

The invention discloses a precursor-aroma compound with sweet aroma and roasting aroma and a preparation method for the precursor-aroma compound and application of the precursor-aroma compound. The preparation method comprises: dissolving ambrox lactone in a sufficient solvent, adding alkali at (-78) DEG C to 50 DEG C, and stirring the mixture to react for over 10 minutes; then adding acryl pyrazine, continuously stirring the mixture to react for over 30 minutes at (-78) DEG C to 50 DEG C, and then carrying out a quenching reaction; and finally, carrying out post-treatment, separation and purification to obtain the target precursor-aroma compound which is added into a product, such as a cigarette, which releases aroma in a combusting or heating process in proportion of 0.00001%-10% by weight. The design, preparation and application of the precursor-aroma compound disclosed by the invention provide a good example for application of spice small molecules which are high in volatility and relatively small in threshold value, and meanwhile, the type of ambergris spice can be increased and enriched, the application of ambergris raw materials and acyl pyrazine is expanded, and the defects of ambrox lactone and acyl pyrazine can be further overcome.

Description

technical field [0001] The embodiments of the present invention relate to the field of tobacco flavors, and more specifically, the embodiments of the present invention relate to a new type of sweet and roasted aroma based on the covalent linkage of ambroxolactone and roasted aroma acyl pyrazine Latent aroma compound and 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...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06C11B9/00A24B3/12
Inventor 陶飞燕杨文敏冯广林戴亚周胜周志刚邱光明刘如灿丁为张艇王耀李朝荣
Owner CHINA TOBACCO SICHUAN IND CO LTD
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