CN113461536A - Phenethyl alcohol ambroxol carbonate latent aroma compound and preparation method and application thereof - Google Patents
Phenethyl alcohol ambroxol carbonate latent aroma compound and preparation method and application thereof Download PDFInfo
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- CN113461536A CN113461536A CN202110897651.5A CN202110897651A CN113461536A CN 113461536 A CN113461536 A CN 113461536A CN 202110897651 A CN202110897651 A CN 202110897651A CN 113461536 A CN113461536 A CN 113461536A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/96—Esters of carbonic or haloformic acids
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- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B3/00—Preparing tobacco in the factory
- A24B3/12—Steaming, curing, or flavouring tobacco
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C68/00—Preparation of esters of carbonic or haloformic acids
- C07C68/06—Preparation of esters of carbonic or haloformic acids from organic carbonates
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/14—All rings being cycloaliphatic
- C07C2602/26—All rings being cycloaliphatic the ring system containing ten carbon atoms
- C07C2602/28—Hydrogenated naphthalenes
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Abstract
The invention discloses a phenylethanol norambroxol carbonate latent aromatic substance and a preparation method and application thereof, wherein phenylethanol and 1, 1' -carbonyl diimidazole are dissolved in dry tetrahydrofuran and are heated and stirred for reaction; tracking the reaction end point by TLC, after the reaction is finished, adding dichloromethane and deionized water into the organic phase, separating liquid, removing water from the organic phase by using anhydrous magnesium sulfate, and concentrating to obtain liquid A; adding ambroxol and N, N-dimethylformamide into the liquid A, heating and stirring for reaction, and cooling to room temperature after reaction; adding deionized water and dichloromethane into the organic phase, separating the liquid, washing the organic phase with deionized water and saturated NaCl solution successively, dewatering the organic phase with anhydrous magnesium sulfate, concentrating to obtain oily liquid, and separating and purifying by column chromatography to obtain the phenylethanol ambrox carbonate latent aroma. The invention provides a good model for the application of perfume micromolecules with high volatility and smaller threshold value, can increase and enrich ambergris scent and sweet scent, and broadens the application range of ambergris scent raw materials and phenethyl alcohol.
Description
Technical Field
The invention relates to the field of tobacco flavors, in particular to a latent aroma with ambergris aroma, honey-sweet rose aroma and sweetening function based on ester bond connection of ambergris diol and phenethyl alcohol and application thereof in cigarette flavoring.
Background
Ambergris is a very popular blending perfume in the market, and is called four big animal perfumes together with musk, civet and marigold. Ambrox is a precious ambergris raw material, has strong and special ambergris fragrance, is called the fragrance of ambergris by the unique fragrance fixing ability, is described as the mild ambergris fragrance as delicate velvet, has ambergris effect, is the fragrance of ambergris, is an excellent fragrance fixing agent, and is the highest one of all synthetic ambergris fragrances. Has been used as a substitute of natural ambergris, is used in high-grade perfume and cosmetic essence, and is very suitable for perfuming skin, hair and fabrics because of no irritation to human body and no allergic reaction to animals.
Ambrox exists in Turkish tobacco, is a product of degradation of Labdane substances, gives sweet aroma, flower aroma and costustoot aroma to cigarette smoke, can cover up crude miscellaneous gas of tobacco, gives pleasant characteristic aroma to the tobacco, makes the cigarette soft and mellow, leaves long aftertaste, is an effective aroma-enhancing and flavoring agent, and is tuned and combined with the costustoot with the characteristics of the tobacco.
However, ambrox has small molecular weight, high volatility, heavy smell and low threshold. The loss is easy in the cigarette processing process, the fragrance is not uniformly released in the cigarette smoking process, and the quality of the cigarettes is unstable due to the volatilization and the loss of the flavoring agent during the storage period.
The phenethyl alcohol exists in some natural products in a free state or in an esterification combination, such as rose extract, rose absolute (containing 60 percent of phenethyl alcohol) and the like, also exists in essential oil of orange blossom, cananga odorata, narcissus, hyacinth, tea leaves and the like, is an edible spice which is important in aromatic compounds for spices and has wide application, is also used as tobacco essence, has sweet rose smell, can improve the taste of tobacco, increases the mellow flavor of cigarette and the taste of saliva, is soft but not lasting, is easy to volatilize in the processing and storage processes, loses the characteristic aroma, and cannot be well applied to tobacco formulas.
The precursor of the flavoring agent is synthesized by a physical or chemical means, has no or little flavor at normal temperature, and is pyrolyzed into one or more molecular fragments under the smoking state of the cigarette to release the flavoring agent, thereby playing the role of improving the quality of the mainstream smoke of the cigarette and achieving the aim of flavoring. The fragrance precursor compound can endow the cigarette with a characteristic style, and fragrance components can be slowly released in the smoking process of the cigarette, so that the fragrance is improved, and the quality of the cigarette is further improved. Meanwhile, the amount of the essence can be reduced, the stability and the storage property of the essence are improved, and the perfuming process is simple and convenient. And the influence on the taste of the cigarettes caused by other factors in the processing process is also avoided.
Disclosure of Invention
The invention overcomes the defects of the prior art and provides the preparation of the carbonate latent aroma with ambergris aroma and honey-sweet rose aroma based on ester bond connection of ambergris diol and phenethyl alcohol and the application of the carbonate latent aroma in cigarette flavoring.
The invention adopts the following technical scheme:
a phenylethanol ambergris carbonate latent aroma with ambergris aroma and honey-sweet rose aroma has the following structural formula:
the latent perfume has the characteristics of high stability and strong processing resistance, and can overcome the defects of volatility, small threshold value, nonuniform release, easy loss in the processing process and the like of ambergris ether and phenethyl alcohol. Meanwhile, the ambroxol ester can be cracked at high temperature (under the condition of smoking) to release corresponding phenethyl alcohol and can be cyclized to generate ambroxol ether fragrance substances at the same time, so that the smoking quality of cigarettes is improved, and the style of the cigarettes is revealed.
The preparation method of the phenethyl alcohol ambroxol carbonate latent aroma comprises the following steps:
the method comprises the following steps: dissolving phenethyl alcohol and 1, 1' -carbonyl diimidazole in dry tetrahydrofuran, and heating and stirring for reaction; monitoring the reaction product of phenethyl alcohol and 1, 1' -carbonyl diimidazole by TLC, tracking the reaction end point, adding dichloromethane and deionized water into an organic phase after the reaction is finished, separating liquid, removing water from the organic phase by using anhydrous magnesium sulfate, and concentrating to obtain liquid A;
step two: adding ambroxol and N, N-dimethylformamide into the liquid A, heating and stirring for reaction, and cooling to room temperature after reaction; adding deionized water and dichloromethane into the organic phase, separating the liquid, washing the organic phase with deionized water and saturated NaCl solution successively, dewatering the organic phase with anhydrous magnesium sulfate, concentrating to obtain oily liquid, and separating and purifying by column chromatography to obtain the phenylethanol ambrox carbonate latent aroma.
The molar ratio of the phenethyl alcohol, the 1, 1' -carbonyl diimidazole and the ambroxol is 1 (1.5-3) to 1-1.5.
The heating stirring reaction in the step one refers to a reaction at 15-40 ℃ for 1-6 h.
The heating stirring reaction in the second step means reaction at 30-120 ℃ for 1-12 h.
The application method of the phenylethanol ambroxol carbonate latent aroma substance is that the phenylethanol ambroxol carbonate latent aroma substance is added into tobacco according to the adding proportion of 0.00001-2% of the weight of the tobacco.
The method for adding the phenylethanol ambroxite latent aroma into tobacco comprises adding surface aroma, adding material aroma or perfuming thin sheets, wherein the tobacco is a mixed type or flue-cured tobacco type cigarette product or a novel tobacco product.
Compared with the prior art, the invention has at least the following beneficial effects:
compared with the traditional carbonic acid diester preparation method, the preparation method has the advantages of low cost, simple and convenient operation and the like. The preparation and the application of the latent aroma compound provide a good model for the application of small aroma molecules with high volatility and smaller threshold, and simultaneously can increase and enrich the ambergris aroma and the honey-sweet rose aroma, widen the application range of ambergris aroma raw materials and phenethyl alcohol, and overcome the self defects of ambergris ether and phenethyl alcohol, such as: small molecular weight, easy volatilization, small threshold, uneven release, easy loss in the processing process and the like.
Drawings
FIG. 1 shows phenylethanol norambroxol carbonate as a fragrance precursor1H NMR spectrum.
FIG. 2 shows phenylethanol norambroxol carbonate as a fragrance13C NMR spectrum.
FIG. 3 is an IR spectrum of a phenylethanol norambroxate latent aroma.
FIG. 4 is a HRMS spectrum of phenylethanol norambroxate daptomatite.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is further described in detail with reference to the following embodiments. It should be understood that the specific embodiments described herein are merely illustrative of the invention and are not intended to limit the invention.
Example 1
1mmol of phenethyl alcohol and 3mmol of 1, 1' -carbonyldiimidazole are dissolved in 20mL of dry tetrahydrofuran, heated to 23 ℃ and stirred for reaction for 3 hours. TLC is used for monitoring the reaction product of the phenethyl alcohol and the 1, 1' -carbonyl diimidazole, the reaction end point is tracked, 25mL of dichloromethane and 2X 15mL of deionized water are added into the organic phase for washing (2X 15mL represents that the deionized water is washed twice, each time is 15mL), liquid separation is carried out, the organic phase is dewatered by anhydrous magnesium sulfate, and liquid A is obtained by concentration.
Adding 1.2mmol of ambroxol and 20mL of N, N-dimethylformamide into the liquid A, heating to 90 ℃, and stirring for reacting for 6 h. And cooling to room temperature after reaction, adding 50mL of deionized water and 50mL of dichloromethane into the organic phase, separating the solution, washing the organic phase with 15mL of deionized water and 15mL of saturated NaCl solution in turn, dewatering the organic phase with anhydrous magnesium sulfate, concentrating to obtain an oily liquid, and then performing column chromatography separation, purification, concentration and drying to obtain the phenethyl alcohol ambroxol ester latent aroma.
Example 2
1mmol of phenethyl alcohol and 2mmol of 1, 1' -carbonyldiimidazole are dissolved in 20mL of dry tetrahydrofuran and heated to 25 ℃ for stirring reaction for 4 h. And monitoring the reaction product of the phenethyl alcohol and the 1, 1' -carbonyl diimidazole by TLC (thin layer chromatography), tracking the reaction end point, adding 25mL of dichloromethane and 2X 15mL of deionized water into the organic phase, washing with water, separating, removing water from the organic phase by using anhydrous magnesium sulfate, and concentrating to obtain liquid A.
Adding 1.5mmol of ambroxol and 20mL of N, N-dimethylformamide into the liquid A, heating to 60 ℃, and stirring for reacting for 6 h. And cooling to room temperature after reaction, adding 50mL of deionized water and 50mL of dichloromethane into the organic phase, separating the solution, washing the organic phase with 15mL of deionized water and 15mL of saturated NaCl solution in turn, dewatering the organic phase with anhydrous magnesium sulfate, concentrating to obtain an oily liquid, and then performing column chromatography separation, purification, concentration and drying to obtain the phenethyl alcohol ambroxol ester latent aroma.
(I) structural characterization of the target product
By infrared spectroscopy, nuclear magnetic resonance (1H NMR and13c NMR and High Resolution Mass Spectrometry (HRMS) are respectively used for carrying out structural characterization on the target product phenylethanol norsalic carbonate latent aroma obtained in example 1, and the specific data are as follows (shown in attached figures 1-4):
phenylethanol norambroxol carbonate: white transparent liquid.1H NMR(300MHz,CDCl3)δ7.27(ddd,J＝13.3,7.5,2.8Hz,5H),4.33(t,J＝7.2Hz,2H),4.18(t,J＝7.6Hz,2H),2.98(t,J＝7.2Hz,2H),2.04(s,1H),1.88(dt,J＝11.7,2.8Hz,1H),1.84–1.71(m,1H),1.71–1.59(m,3H),1.50–1.42(m,2H),1.38(d,J＝14.8Hz,2H),1.33–1.21(m,1H),1.20–1.12(m,4H),1.10(t,J＝4.4Hz,1H),0.96–0.86(m,5H),0.79(s,6H)；13C NMR(75MHz,CDCl3)δ155.17,137.30,128.91,128.51,126.60,73.50,69.77,68.10,57.57,56.01,44.49,41.85,39.54,38.69,35.15,33.35,33.23,24.53,23.88,21.43,20.46,18.38,15.27；IR,ν/cm-1:3496.68,3028.30，2933.61,1740.42,1497.74,1455.95,1401.86,1267.54；HRMS:C25H38NaO4The calculated value was 425.266230, found 425.266434.
(II) perfuming application of target latent aroma in tobacco
Weighing a certain amount of phenethyl alcohol ambroxol carbonate latent aroma, dissolving with 95% ethanol, adding on certain flue-cured tobacco type tobacco shred according to the proportion of 0.001%, 0.005%, 0.01%, 0.05% and 0.2%, and rolling into experimental cigarette. And (5) adding ethanol with the same proportion to the same cut tobacco, and rolling into blank cigarettes. The blank cigarette in the experiment has the defects of irritation, heavy miscellaneous gas and the like, and the comparison and the smoking evaluation show that the smoking evaluation result is shown in the following table compared with the control sample.
TABLE 1 perfuming smoke panel test results of phenylethanol norambrox carbonate
The research on the thermal cracking product of the latent aroma shows that: the main thermal cracking products analyzed by the thermal cracking gas chromatography mass spectrogram of the latent aromatic substance at 300 ℃ are phenethyl alcohol and ambrox. Comparing the smoking results, the cigarette added with the latent aroma has the effects of increasing the aroma of rich honey, sweet aroma, flower aroma, costustoot and ambergris aroma, reducing the stimulation, covering miscellaneous gas, and enabling the smoke to be pure and fine.
Although the invention has been described herein with reference to illustrative embodiments thereof, it should be understood that numerous other modifications and embodiments can be devised by those skilled in the art that will fall within the spirit and scope of the principles of this disclosure.
Claims (7)
1. A phenylethanol ambroxol carbonate latent aroma substance is characterized in that the structural formula is as follows:
2. the method of preparing a phenylethanol norambroxate ester latent aroma as claimed in claim 1, characterized in that it comprises the steps of:
the method comprises the following steps: dissolving phenethyl alcohol and 1, 1' -carbonyl diimidazole in dry tetrahydrofuran, and heating and stirring for reaction; monitoring the reaction product of phenethyl alcohol and 1, 1' -carbonyl diimidazole by TLC, tracking the reaction end point, adding dichloromethane and deionized water into an organic phase after the reaction is finished, separating liquid, removing water from the organic phase by using anhydrous magnesium sulfate, and concentrating to obtain liquid A;
step two: adding ambroxol and N, N-dimethylformamide into the liquid A, heating and stirring for reaction, and cooling to room temperature after reaction; adding deionized water and dichloromethane into the organic phase, separating the liquid, washing the organic phase with deionized water and saturated NaCl solution successively, dewatering the organic phase with anhydrous magnesium sulfate, concentrating to obtain oily liquid, and separating and purifying by column chromatography to obtain the phenylethanol ambrox carbonate latent aroma.
3. The method of claim 2, wherein the molar ratio of the phenethyl alcohol, the 1, 1' -carbonyldiimidazole and the ambroxol is 1 (1.5-3) to (1-1.5).
4. The method for preparing phenylethanol norambroxol carbonate latently fragrant substance according to claim 2, wherein the heating and stirring reaction in the first step is carried out at 15-40 ℃ for 1-6 h.
5. The method for preparing phenylethanol norambroxol carbonate latently fragrant substance according to claim 2, wherein the heating and stirring reaction in the second step is a reaction at 30-120 ℃ for 1-12 h.
6. The use of the phenylethanol norambrox carbonate latent according to claim 1, wherein the phenylethanol norambrox carbonate latent is added to tobacco in an addition ratio of 0.00001% to 2% by weight of tobacco.
7. The use of the phenylethanol norambroxate ester pro-fragrance as claimed in claim 6, wherein the phenylethanol norambroxate ester pro-fragrance is added to tobacco by adding top notes, flavoring notes or sheet flavoring, wherein the tobacco is a blended or flue-cured type of cigarette product, or is a novel tobacco product.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN114539062A (en) * | 2022-04-08 | 2022-05-27 | 安徽中烟工业有限责任公司 | Nicotine carbonate, synthetic method thereof and application thereof in cigarette preparation |
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