CN112480051A - 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geranyl carbonate alcohol ester and application thereof - Google Patents
2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geranyl carbonate alcohol ester and application thereof Download PDFInfo
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- CN112480051A CN112480051A CN202011458314.8A CN202011458314A CN112480051A CN 112480051 A CN112480051 A CN 112480051A CN 202011458314 A CN202011458314 A CN 202011458314A CN 112480051 A CN112480051 A CN 112480051A
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- pyran
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/32—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
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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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Abstract
The invention relates to a 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-geraniol carbonate and application thereof, the technical scheme takes 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone and geraniol as raw materials to prepare the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-geraniol carbonate, the compound has good storage stability and flavoring stability, the tobacco flavor raw material at least comprising the compound is added into cigarettes, the compound can be cracked to release 2, 3-dihydro-3, the 5-dihydroxy-6-methyl-4H-pyran-4-one and the geraniol have the effects of increasing sweet feeling of the oral cavity and improving aftertaste comfort, can increase the fragrance of the smoke, improve the fragrance quality of the cigarette and have potential application value.
Description
Technical Field
The invention belongs to the technical field of tobacco flavor synthesis, and particularly relates to 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geranyl carbonate and application thereof.
Background
The 'sweet taste' of smoke is a key index influencing the sensory quality and the style characteristics of cigarettes, and in order to show the characteristics, substances such as saccharides, extractum, Maillard reactants and the like are generally used in the flavoring of Chinese cigarettes. These substances can generate sweet taste in smoke, mainly because they contain or crack to generate volatile sweet substances such as pyrones and dehydrated saccharides, but because the content of these sweet substances is very low, the cigarette 'sweet taste' characteristics are not good. Therefore, the volatile sweet substances are directly used as the fragrant raw materials, so that the content of the sweet substances in the smoke can be obviously improved, and the 'sweet taste' characteristic of the Chinese cigarette is effectively displayed.
2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) is commonly present in cigarette smoke, Maillard reaction products, sugar cracking products and natural extractum. The 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone has better water solubility, presents prominent sweet taste in taste sense, is in obvious positive correlation with the sweet taste of smoke, can obviously improve the sweet return feeling of the smoke of the cigarette, and highlights the taste characteristics of the sweet taste and the moist taste of the cigarette. However, the stability of DDMP is poor, and the DDMP has not been applied as a tobacco fragrance raw material to date. Through literature and experimental research, 5-enol-type exposed hydroxyl is a main factor of deterioration of the compound, and the stability of the compound can be obviously improved by bonding 5-hydroxyl.
Disclosure of Invention
The invention aims to provide 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geraniol carbonate and application thereof, so as to solve the problems that DDMP is poor in stability, easy to deteriorate and damage and incapable of being used as a perfume raw material.
In order to achieve the purpose, the invention provides the following technical scheme:
a2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geranyl carbonate ester has the structure:
the preparation method of the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geraniol carbonate comprises the following steps:
1) adding geraniol and an organic solvent into a reaction bottle under the protection of nitrogen, cooling to-5 ℃, sequentially adding alkali and bis (trichloromethyl) carbonate into a reaction system, and heating to room temperature for reaction for 2-3 hours;
2) adding 2, 3-dihydro-3, 5-hydroxy-6-methyl-4H-pyran-4-one into the reaction system, and continuously reacting for 2-3H at room temperature;
3) after the reaction is finished, washing the organic mixed solution by using a saturated sodium chloride solution, drying the organic mixed solution by using anhydrous sodium sulfate, evaporating the solvent under reduced pressure, and separating a crude product by using silica gel column chromatography to obtain the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-geranyl carbonate.
Further, the organic solvent in the step 1) is one of tetrahydrofuran, dimethyl sulfoxide or 1, 4-dioxane.
Further, the base in the step 1) is one of diethylamine, triethylamine or diisopropylethylamine.
Further, the mole ratio of geraniol to base, bis (trichloromethyl) carbonate and 2, 3-dihydro-3, 5-hydroxy-6-methyl-4H-pyran-4-one is 1: (1-3): (0.33-1): (1-2).
The use of any one of the above 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geraniol carbonate in a cigarette.
Further, the alcoholic solution of the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geraniol carbonate is sprayed on the cut tobacco.
Further, the addition amount of the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geraniol carbonate is 1-50 ppm of the mass of the cut tobacco.
The invention has the beneficial effects that:
the technical scheme takes 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) and geraniol as raw materials to prepare 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geraniol carbonate (DDMP geraniol carbonate), the compound has good storage stability and perfuming stability, the tobacco fragrance raw materials at least comprising the DDMP geraniol carbonate are added into cigarettes, the DDMP geraniol carbonate can be cracked to release 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one and geraniol, and the effects of increasing the sweet feeling of the oral cavity and improving the aftertaste comfort can be achieved, can also enrich the cigarette fragrance, improve the cigarette fragrance quality and have potential application value.
Detailed Description
The technical solutions of the present invention are described in detail below by examples, and the following examples are only exemplary and can be used only for explaining and explaining the technical solutions of the present invention, but not construed as limiting the technical solutions of the present invention.
Example 1
Under the protection of nitrogen, geraniol (1.54g,10mmol) is dissolved in 30mL of anhydrous tetrahydrofuran, the reaction system is cooled to 0 ℃, triethylamine (2.42g,24mmol) and bis (trichloromethyl) carbonate (0.98g,3.3mmol) are sequentially added, after the addition is finished, the reaction is carried out at room temperature for 2H, then 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (1.44g,10mmol) is added into the reaction system, the reaction is continued for 3H at room temperature, after the reaction is finished, the reaction solution is washed by saturated sodium chloride solution, an organic layer is separated, anhydrous sodium sulfate is dried, the solvent is evaporated, and the residue is purified by silica gel column chromatography, and petroleum ether (V): ethyl acetate (V) ═ 5:1 elution was carried out to obtain 2.66g of the target 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geranyl carbonate in a yield of 82.6%.
Example 2
Under the protection of nitrogen, geraniol (1.54g,10mmol) is dissolved in 30mL of dimethyl sulfoxide, the reaction system is cooled to 0 ℃, diethylamine (2.20g,30mmol) and bis (trichloromethyl) carbonate (0.98g,3.3mmol) are sequentially added, after the addition is finished, the reaction is carried out at room temperature for 2H, then 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (1.44g,10mmol) is added into the reaction system, the reaction is continued for 3H at room temperature, after the reaction is finished, the reaction solution is washed by saturated sodium chloride solution, an organic layer is separated, anhydrous sodium sulfate is dried, the solvent is evaporated, and the residue is purified by silica gel column chromatography, petroleum ether (V): ethyl acetate (V) ═ 5:1 elution was carried out to obtain 2.56g of the target 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geranyl carbonate in 79.0% yield.
Example 3
Under the protection of nitrogen, geraniol (1.54g,10mmol) is dissolved in 30mL of anhydrous 1, 4-dioxane, the reaction system is cooled to 0 ℃, diisopropylethylamine (3.88g,30mmol) and bis (trichloromethyl) carbonate (1.19g,4mmol) are sequentially added, reaction is carried out at room temperature for 3H after the addition is finished, then 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (1.44g,10mmol) is added into the reaction system, reaction is continued for 3H at room temperature, after the reaction is finished, the reaction solution is washed by saturated sodium chloride solution, an organic layer is separated, anhydrous sodium sulfate is dried, a solvent is evaporated, and the residue is purified by silica gel column chromatography, petroleum ether (V): ethyl acetate (V) ═ 5:1 elution was carried out to obtain 2.24g of the target 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geranyl carbonate in 69.1% yield.
Example 4
Under the protection of nitrogen, geraniol (1.54g,10mmol) is dissolved in 30mL of anhydrous tetrahydrofuran, the reaction system is cooled to 0 ℃, triethylamine (3.03g,30mmol) and bis (trichloromethyl) carbonate (1.19g,4mmol) are sequentially added, after the addition is finished, the reaction is carried out at room temperature for 3H, then 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (1.73g,12mmol) is added into the reaction system, the reaction is continued for 3H at room temperature, after the reaction is finished, the reaction solution is washed by saturated sodium chloride solution, an organic layer is separated, anhydrous sodium sulfate is dried, the solvent is evaporated, and the residue is purified by silica gel column chromatography, and petroleum ether (V): ethyl acetate (V) ═ 5:1 elution was carried out to obtain 2.31g of the target 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geranyl carbonate in a yield of 71.3%.
The application also relates to a tobacco flavor which at least comprises 2, 3-dihydro-3-hydroxy-5-O-geraniol carbonate-6-methyl-4H-pyran-4-ketone.
Testing the performance of the spice: an amount of 2, 3-dihydro-3-hydroxy-5-O-geraniol carbonate-6-methyl-4H-pyran-4-one (DDMP geraniol carbonate) and an amount of 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (DDMP) prepared in any of the above examples were weighed out separately and diluted with ethanol to a 5% solution for use. Weighing 100g of blank cigarette cut tobacco without flavoring, evenly spreading the blank cigarette cut tobacco in a clean tray, evenly spraying DDMP geraniol carbonate and DDMP solution on the cut tobacco respectively to prepare flavored cut tobacco with the proportion of DDMP geraniol carbonate, DDMP and the cut tobacco of 5ppm, 10ppm, 20ppm, 30ppm and 50ppm, sealing and placing for 4h, placing in a 50 ℃ oven for drying, humidifying to standard moisture (12%) with distilled water, rolling into standard cigarettes, balancing the moisture (the humidity is 60% +/-2%, the temperature is 22 +/-1 ℃) for 48h, and then evaluating the smoking. The control sample was a blank cigarette and the control sample was equilibrated for 48h under the same temperature and humidity conditions.
TABLE 1 DDMP geraniol carbonate and DDMP perfuming smoke panel test results
As can be seen from Table 1: the DDMP geraniol carbonate and the DDMP have the characteristics of remarkably improving the 'sweet back' of cigarette smoke, highlighting the 'sweet' and 'moist' taste characteristics of cigarettes, improving and modifying the fragrance of the cigarettes, reducing the irritation, improving the smoking taste and enabling the aftertaste to be clean and comfortable. Compared with DDMP, the DDMP geraniol carbonate can also increase the fragrance and fineness of the smoke, improve the fragrance quality of the cigarette and have potential application value. However, when the content of DDMP geraniol carbonate exceeds 30ppm, the fragrance of the smoke is affected, the aftertaste is poor, and the uncomfortable feeling is generated, the recommended dosage is as follows: 10 to 30 ppm.
Although embodiments of the present invention have been shown and described, it will be appreciated by those skilled in the art that changes, modifications, substitutions and alterations can be made in these embodiments without departing from the principles and spirit of the invention, the scope of which is defined in the appended claims and their equivalents.
Claims (8)
1. A 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geranyl carbonate ester characterized by the structure:
2.2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonic acid geraniol ester according to claim 1, characterized in that the preparation method comprises the following steps:
1) adding geraniol and an organic solvent into a reaction bottle under the protection of nitrogen, cooling to-5 ℃, sequentially adding alkali and bis (trichloromethyl) carbonate into a reaction system, and heating to room temperature for reaction for 2-3 hours;
2) adding 2, 3-dihydro-3, 5-hydroxy-6-methyl-4H-pyran-4-one into the reaction system, and continuously reacting for 2-3H at room temperature;
3) after the reaction is finished, washing the organic mixed solution by using a saturated sodium chloride solution, drying the organic mixed solution by using anhydrous sodium sulfate, evaporating the solvent under reduced pressure, and separating a crude product by using silica gel column chromatography to obtain the 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-ketone-5-O-geranyl carbonate.
3. The 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonic acid geraniol ester according to claim 2, wherein the organic solvent in step 1) is one of tetrahydrofuran, dimethyl sulfoxide or 1, 4-dioxane.
4. The 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geranylcarbonate ester according to claim 2, wherein the base in step 1) is one of diethylamine, triethylamine, or diisopropylethylamine.
5. The 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate geraniol ester according to claim 2, wherein the molar ratio of geraniol to base, bis (trichloromethyl) carbonate and 2, 3-dihydro-3, 5-hydroxy-6-methyl-4H-pyran-4-one is 1: (1-3): (0.33-1): (1-2).
6. Use of 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geraniol carbonate, characterized in that the use of 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geraniol carbonate according to any one of claims 1 to 5 in cigarettes.
7. Use of geraniol 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate according to claim 6, wherein the alcoholic solution of geraniol 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-carbonate is sprayed onto cut tobacco.
8. The use of 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geraniol carbonate according to claim 6, wherein the amount of 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-geraniol carbonate added is 1-50 ppm of the mass of the tobacco shred.
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Cited By (2)
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| CN113461535A (en) * | 2021-08-05 | 2021-10-01 | 四川三联新材料有限公司 | Geraniol ambroxol carbonate latent aromatic, and preparation method and application thereof |
| CN116286185A (en) * | 2023-03-29 | 2023-06-23 | 河南中烟工业有限责任公司 | Sweet essence for heating cigarettes, tobacco sheet and heating cigarettes |
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Application publication date: 20210312 |