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A kind of (e) type solanone, its preparation method and application

A technology of solanone and isopropyl, which is applied in the field of organic synthesis, can solve the problems of long routes, increased safety risks and costs, and achieve the effects of high safety, enhanced aroma elegance, and enhanced smoke fullness

Active Publication Date: 2022-03-25
CHINA TOBACCO YUNNAN IND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of these synthetic methods have long routes and use alkyl metal reagents that are sensitive to air and moisture, which increases safety risks and costs in production
In addition, none of the existing solanone synthesis methods takes into account the stereo configuration control of the product (C5 chiral carbon R, S configuration), and what is obtained is a stereo configuration mixture or a racemate of solanone, Pure solanone such as (S,E)-5-isopropyl-8-methyl-6,8-dien-2-one of (E) type, or (R,E)-5-isopropyl -8-Methyl-6,8-dien-2-one not available yet

Method used

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  • A kind of (e) type solanone, its preparation method and application
  • A kind of (e) type solanone, its preparation method and application
  • A kind of (e) type solanone, its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: the synthesis of (S)-2-isopropyl-5-carbonyl hexanal

[0027] Place 73mg (about 0.4mmol) of ethyl 3,4-dihydroxybenzoate in a round bottom flask, and add 53.48mg (0.2mmol) of (S)-2-(methoxybenzhydryl)pyrrole in sequence alkanes, 215 μL (approximately 2 mmol) of isovaleraldehyde and 243 μL (approximately 3 mmol) of methyl vinyl ketone, the reaction was stirred at room temperature, the solid dissolved, and stirred for 24 hours.

[0028] After the reaction was finished, the remaining methyl vinyl ketone was removed by rotary evaporation, and the remaining liquid was separated by column chromatography of sherwood oil: ethyl acetate=20:1 to obtain 230.1 mg of a light yellow liquid, with a yield of 74%; analyzed as (S )-2-isopropyl-5-carbonylhexanal. analyse as below:

[0029] 1 H NMR (400MHz, Chloroform-d) δ9.59((d, J=2.8Hz, 1H), 2.47(m, 1H), 2.35(m, 1H), 2.11(s, 3H), 2.07-1.99(m , 2H), 1.85-1.70 (m, 2H), 0.98 (d, J=6.6Hz, 3H), 0.95 (d, J=6.6Hz, 3H). 13 C NM...

Embodiment 2

[0032] Embodiment 2: the synthesis of (E)-solanone

[0033] Put 5.2 g (about 27.3 mmol) of (2-methylallyl) diethyl phosphonate in the reaction flask, add 70 mL of methyl tert-butyl ether to dissolve, and 9.5 mL (about 54.6 mmol) of hexamethyl Phosphoric triamide, the system was cooled to minus 78°C; 13.7mL of 2M (about 27.3mmol) sodium hexamethyldisilazide tetrahydrofuran solution was added dropwise, and stirred at minus 78°C for 30 minutes, Finally, a solution of 3.3 g (about 21 mmol) of (S)-2-isopropyl-5-carbonyl hexanal obtained in Example 1 in 70 mL of methyl tert-butyl ether was added, and the temperature was slowly raised to room temperature within 6 hours , and stirred for another 10 hours at room temperature.

[0034] After the reaction, 100 mL of water was added to the system, extracted three times with ether, the combined organic phases were dried over anhydrous sodium sulfate, concentrated, and the remaining liquid was subjected to column chromatography with petrol...

Embodiment 3

[0038] Embodiment 3: the application of (E) type solanone in cigarette shredded tobacco flavoring

[0039] Taking a certain Yunproduct brand sample cigarette as the experimental object, the added amount of spices was calculated according to the weight of shredded tobacco, and two pure (E) type solanones synthesized in Example 2 of the present invention: (S, E)-5-isopropyl- 8-Methyl-6,8-dien-2-one (injection plus cigarette as sample 1) and (R,E)-5-isopropyl-8-methyl-6,8-diene-2 -ketone (injection plus cigarettes is sample 2) is made into ethanol solution of a certain concentration, and with CIJECTOR flavor and fragrance injection machine, its ethanol solution is evenly injected into cigarettes according to the percentage of spices in tobacco shreds by 0.005% by weight; inject under the same conditions The cigarette branch (sample 0) of same volume ethanol is control sample, at relative humidity 60%, 22 ℃ of conditions balance 48 hours, according to tobacco industry standard " t...

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Abstract

The invention discloses an (E)-type solanone, whose three-dimensional structural formula is: or its name is: (S,E)-5-isopropyl-8-methyl-6,8-diene-2-one , or (R,E)‑5‑isopropyl‑8‑methyl‑6,8‑dien‑2‑one. The invention also discloses the preparation method of the (E) type solanone and its use for flavoring shredded tobacco of cigarettes.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to (E) type solanone, its preparation method and its use in tobacco flavoring. Background technique [0002] Solanone is one of the most important aroma components in tobacco, which plays an important role in improving the taste of tobacco and enhancing the characteristics of smoke. Used in the flavoring of tobacco products, solanone can make the smoke richer and fuller, improve the taste, and have fresh black tea, fragrance, grass and other aromas, and have a slightly sweet aroma. Foreign flavor companies import a large amount of tobacco flavor to my country every year, but so far they are unwilling to import solanone, a single flavor, to my country. Because solanone is added to any shredded tobacco, it shows a unique effect, and no single fragrance can match it in terms of deodorization, flavor and strength, and coordination with shredded tobacco. The produc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C49/227C07C45/68A24B3/12
CPCC07C49/227A24B3/12C07B2200/07
Inventor 雷声刘志华李振杰冒德寿王凯王昆淼付磊者为杨影周强辉
Owner CHINA TOBACCO YUNNAN IND
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