CN110862366B - Milk-flavored tobacco sweetener, preparation method and application thereof in cigarettes - Google Patents
Milk-flavored tobacco sweetener, preparation method and application thereof in cigarettes Download PDFInfo
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- CN110862366B CN110862366B CN201911083184.1A CN201911083184A CN110862366B CN 110862366 B CN110862366 B CN 110862366B CN 201911083184 A CN201911083184 A CN 201911083184A CN 110862366 B CN110862366 B CN 110862366B
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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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- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
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- A24B3/00—Preparing tobacco in the factory
- A24B3/12—Steaming, curing, or flavouring tobacco
Abstract
The invention relates to a milk-flavored tobacco sweetener, a preparation method and application thereof in cigarettes, the technical scheme takes 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one as a raw material, two milk-flavored 2, 3-dihydro-3-hydroxy-5-acyloxy-6-methyl-4H-pyran-4-one are prepared through esterification reaction, the compound has good storage stability and flavoring stability, and the compound not only shows the effects of increasing the sweet feeling of the mouth cavity and improving the comfort of aftertaste, but also can enrich the fragrance of cigarettes, increase the permeability and the fineness of the smoke and promote the quality of the cigarettes, and has potential application value when being added into cigarettes.
Description
Technical Field
The invention belongs to the technical field of synthesis of tobacco flavors, and particularly relates to a milk-flavored 2, 3-dihydro-3-hydroxy-5-acyloxy-6-methyl-4H-pyran-4-one, a preparation method and application of the milk-flavored 2, 3-dihydro-3-hydroxy-5-acyloxy-6-methyl-4H-pyran-4-one serving as a flavor in cigarettes.
Background
2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one is commonly found in cigarette smoke, maillard reaction products, sugar cleavage products, and natural extracts. Structurally, 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one is similar to maltol, a common caramel flavor substance, and belongs to pyranenolone compounds, and most of the compounds with cyclic enolone have caramel-like flavor; compared with caramel-like fragrant substances such as maltol, the 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-ketone has better water solubility, and the "sweet" appearing on taste is more prominent; the sweet taste of the cigarette smoke is obviously and positively correlated with the sweet taste of the smoke, so that the sweet taste of the cigarette smoke can be obviously improved, and the sweet and moist taste characteristics of the cigarette are highlighted.
However, 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one has poor stability and is susceptible to deterioration and damage, making it hitherto not available as a sweetener. Therefore, the molecular structure has important influence on the flavor, and the flavor characteristics in certain aspects are enhanced, adverse influence factors in use are eliminated or weakened by purposefully modifying the 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one structure, so that the novel flavor for cigarettes has important significance in development.
In the classification of the perfume types, several perfumes of the same or similar type, which are either homologues or contain the same type of group, or isomers, mostly have similar chemical structures. Therefore, the development of structurally similar derivatives to obtain new fragrances based on 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one is an effective approach.
According to the technical scheme, 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one is used as a raw material, 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one and 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one are synthesized through esterification reaction, the chemical properties of the two compounds are stable, but the two compounds can release 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one, isobutyric acid and isovaleric acid during high-temperature pyrolysis, and the additive can not only increase the sweet feeling of an oral cavity, improve the comfort of aftertaste, but also endow cigarettes with typical milk flavor characteristics, and have potential application values.
Disclosure of Invention
The invention aims to provide a milk-flavored tobacco sweetener, a preparation method and application thereof in cigarettes, and aims to solve the problems that 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one in the prior art is poor in stability and easy to deteriorate and damage.
The invention is realized by the following technical scheme:
a milk-flavored tobacco sweetener is prepared from 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one and/or 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one.
The structural formula of the 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one is as follows:
the structural formula of the 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one is as follows:
the preparation method of any one of the milk-flavored tobacco sweetener comprises the following steps:
1) Adding 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one and an organic solvent into a reaction bottle, and cooling to-5 ℃ under the protection of nitrogen;
2) Sequentially adding organic base and an acylating reagent at the temperature of the step 1), and heating to room temperature for reacting for 4-8 hours, wherein the acylating reagent is one or more of corresponding isobutyric anhydride, isovaleric anhydride, isobutyryl chloride or isovaleryl chloride;
3) After the reaction is finished, the organic mixed solution is washed with water and saturated sodium chloride solution for 3 times, dried over anhydrous sodium sulfate, decompressed and distilled to remove the solvent, and the crude product is separated by silica gel column chromatography to obtain 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one and/or 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one.
The organic solvent in the step 1) is one of dichloromethane, chloroform, toluene, acetonitrile, n-hexane, tetrahydrofuran or cyclohexane.
The organic base in the step 2) is one of triethylamine, pyridine or diisopropylmethylamine.
The molar ratio of the 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one, the organic base and the acylating agent is 1: (1-1.5): (1-2).
The sour flavor tobacco sweetener of any one of the above, applied to cigarettes.
Further, the alcohol solution of the sour-flavor tobacco sweetener is sprayed on the cut tobacco.
Further, the addition amount of the sour-flavor tobacco sweetener is 1-20 ppm of the mass of tobacco shreds.
The beneficial effects of the invention are as follows:
according to the technical scheme, 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one is used as a raw material, two milk-flavored 2, 3-dihydro-3-hydroxy-5-acyloxy-6-methyl-4H-pyran-4-one are prepared through esterification reaction, the compound has good storage stability and flavoring stability, and the effect of increasing the sweet feeling of an oral cavity and improving the comfort of aftertaste is shown by adding the compound into cigarettes, so that the smoke flavor can be enriched, the smoke permeability and the fineness are increased, and the cigarette flavor quality is improved, and the compound has potential application value.
Drawings
FIG. 1 is a nuclear magnetic resonance hydrogen spectrum of 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one;
FIG. 2 is a nuclear magnetic resonance carbon spectrum of 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one;
FIG. 3 is a mass spectrum of 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one;
FIG. 4 is a nuclear magnetic resonance hydrogen spectrum of 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one;
FIG. 5 is a nuclear magnetic resonance carbon spectrum of 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one;
FIG. 6 is a mass spectrum of 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one.
Detailed Description
The following examples are given by way of illustration only and are not to be construed as limiting the scope of the invention.
The following are some of the reagents and instruments used in the examples.
2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (analytically pure, homemade); isobutyric anhydride, isovaleric anhydride, isobutyryl chloride, isovaleryl chloride, sodium chloride (analytically pure, national pharmaceutical systems chemical reagent limited); triethylamine, pyridine, diisopropylmethylamine (analytically pure, shanghai darifenacin fine chemicals limited); dichloromethane, chloroform, toluene, acetonitrile, n-hexane, tetrahydrofuran, cyclohexane, anhydrous sodium sulfate (analytically pure, beijing chemical plant); petroleum ether, ethyl acetate (analytically pure, shanghai darifenacin fine chemicals limited).
0.0001g analytical balance (Sartorius company, germany); HH-6 thermostatic water bath (Jiangsu gold altar Honghua Instrument works); DF-101S heat collection type constant temperature heating magnetic stirrer (Henan province, hehua Instrument Limited liability company); SHZ-D (III) circulating water type vacuum pump (Henan province, ministry of China, instrument Limited); rotary evaporator (IKA group, germany); bruker Avance AMX-600 Nuclear magnetic resonance spectrometer (Bruker Co., U.S.); ultra performance liquid chromatography-electrospray ion source-mass spectrometer (company agilent technologies, usa).
In the technical scheme of the application, the milk-flavored tobacco sweetener consists of 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one and/or 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one.
The structural formula of the 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one is as follows:
the structural formula of the 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one is as follows:
the preparation method of the milk-flavored sweetener has the structural formula:
Example 1
In a 100mL round bottom flask, 2.88g of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (20 mmol) and 30mL of anhydrous dichloromethane were added, cooled to 0℃and 2.42g of triethylamine (24 mmol) and 2.56g of isobutyryl chloride (24 mmol) were sequentially added under nitrogen protection, then the mixture was allowed to react at room temperature for 6 hours, after the reaction was completed, the reaction mixture was sequentially washed with water and saturated sodium chloride solution for 3 times, the organic phase was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure (in this example and the following examples, the degree of vacuum of the reduced pressure was determined according to the actual conditions or needs and did not affect the realization of the technical scheme of the present application), and the crude product was purified by silica gel column chromatography, petroleum ether (V): ethyl acetate (V) =4:1 afforded 4.04g of colorless oil as 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one in 94.39% yield.
Example 2
In a 100mL round bottom flask, 2.88g of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (20 mmol) and 30mL of anhydrous toluene were added, cooled to-5℃and 1.90g of pyridine (24 mmol) and 4.74g of isobutyric anhydride (30 mmol) were added in sequence under the protection of nitrogen, then the reaction was allowed to proceed to room temperature for 8 hours, after the reaction was completed, the reaction solution was washed in sequence with water and saturated sodium chloride solution for 3 times, the organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the crude product was separated and purified by silica gel column chromatography, petroleum ether (V): ethyl acetate (V) =4:1 afforded 3.95g of colorless oil as 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one in 92.29% yield.
Example 3
In a 100mL round bottom flask, 2.88g of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (20 mmol) and 30mL of anhydrous chloroform were added, cooled to 0℃and 2.76g of diisopropylmethylamine (24 mmol) and 2.89g of isovaleryl chloride (24 mmol) were added in sequence under nitrogen protection, then the mixture was allowed to react at room temperature for 6H, after the reaction was completed, the reaction solution was washed with water and saturated sodium chloride solution in sequence for 3 times, the organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the crude product was separated and purified by silica gel column chromatography, petroleum ether (V): ethyl acetate (V) =4:1 afforded 4.31g of colorless oil as 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one in 94.51% yield.
Example 4
In a 100mL round bottom flask, 2.88g of 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one (20 mmol) and 30mL of acetonitrile were added, cooled to-5℃and 2.42g of triethylamine (24 mmol) and 5.58g of isovaleric anhydride (30 mmol) were added in sequence under nitrogen protection, then the reaction was allowed to proceed to room temperature for 8 hours, after the reaction was completed, the reaction solution was washed in sequence with water and saturated sodium chloride solution for 3 times, the organic phase was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the crude product was separated and purified by silica gel column chromatography, petroleum ether (V): ethyl acetate (V) =4:1 afforded 4.17g of colorless oil as 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one in 91.45% yield.
Structural characterization data for 2, 3-dihydro-3-hydroxy-5-acyloxy-6-methyl-4H-pyran-4-one:
as shown in fig. 1 to 3, 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one: 1 H NMR(600MHz,CDCl 3 )δ4.59(dd,J＝10.9,J＝6.2Hz,1H),4.44(dd,J＝13.4,J＝6.2Hz,1H),4.12(dd,J＝13.3,J＝10.9Hz,1H),2.79(dt,J＝14.0,J＝7.0Hz,1H),1.99(s,3H),1.29(d,J＝7.0Hz,6H). 13 C NMR(150MHz,CDCl 3 )δ:186.6,174.7,168.6,126.5,71.1,67.1,33.6,18.9,16.2.MS-EI,m/z 214,144,101,71,43。
as shown in fig. 4 to 6, 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one: 1 H NMR(600MHz,CDCl 3 )δ4.59(dd,J＝10.9,J＝6.2Hz,1H),4.44(dd,J＝13.3,J＝6.2Hz,1H),4.12(dd,J＝13.3,J＝11.0Hz,1H),2.42–2.38(m,2H),2.20(dt,J＝13.6,J＝6.8Hz,1H),2.00(s,3H),1.04(d,J＝6.7Hz,6H). 13 C NMR(150MHz,CDCl 3 )δ186.6,170.5,168.7,126.5,71.1,67.1,42.6,25.9,22.4,16.4.MS-EI,m/z 228,144,101,85,57,41。
fragrance performance test: a certain amount of 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one (compound 1), 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one (compound 2) and maltol were weighed separately and diluted with ethanol to a 5% solution for use. 100g of blank cigarette tobacco shreds without flavoring are weighed and evenly spread in a clean tray, the flavored tobacco shreds of 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one, 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one and maltol solution are respectively and evenly sprayed on the tobacco shreds, 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one, 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one and maltol with specific gravity of 1ppm, 2ppm, 5ppm, 10ppm, 15ppm and 20ppm are respectively, the tobacco shreds are placed in a sealed condition for 4 hours, are put into a 50 ℃ oven for drying, the tobacco shreds are humidified by distilled water until standard moisture (12%) is obtained, and standard cigarettes are prepared, and the balanced moisture (60% +/-2% temperature is 22+/-48 ℃ C.) after the evaluation is carried out. The control sample is a blank cigarette and is balanced for 48 hours under the same temperature and humidity conditions.
Table 1 results of compound 1, compound 2 and maltol perfuming and sucking evaluation
As can be seen from table 1: the 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one ( compound 1, 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one (compound 2) and maltol each have the effects of significantly improving and modifying the aroma of cigarettes, reducing irritation, improving taste and making the aftertaste clean and comfortable, wherein, compared with maltol, compound 1 and compound 2 have better solubility, the "sweet" exhibited in taste is more prominent, the "sweet" characteristic of cigarette smoke is remarkably improved, the taste characteristics of the cigarette "sweet" and "moist" are highlighted, and at the same time, the aroma amount of cigarettes can also be increased, the aroma of milk is increased, but after the amount of the compound 1 and compound 2 exceeds 15ppm, the milk aroma is too heavy, the sweet feel occurs, the aroma is also scorched, the aroma is influenced, and the aftertaste is poor, and uncomfortable is suggested to be produced, namely 10-15 ppm.
Although embodiments of the present invention have been shown and described, it will be understood by those skilled in the art that various changes, modifications, substitutions and alterations can be made therein without departing from the spirit and scope of the invention as defined by the appended claims and their equivalents.
Claims (6)
1. A milk-flavored tobacco sweetener is characterized by comprising 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one and/or 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one composition;
the 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-ones of the formula:
；
the 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-ones of the formula:
；
the method comprises the following steps:
1) 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4 was added to a reaction flaskH-pyran-4-one and organic solvent, under the protection of nitrogen, cooling to-5 ℃;
2) Sequentially adding organic base and an acylating reagent at the temperature of the step 1), and heating to room temperature for reacting for 4-8 hours, wherein the acylating reagent is one or a combination of more than one of corresponding isobutyric anhydride, isovaleric anhydride, isobutyryl chloride or isovaleryl chloride;
3) After the reaction is finished, the organic mixed solution is washed with water and saturated sodium chloride solution for 3 times in sequence, dried with anhydrous sodium sulfate, the solvent is distilled off under reduced pressure, and the crude product is separated by silica gel column chromatography to obtain 2, 3-dihydro-3-hydroxy-5-isobutyryloxy-6-methyl-4H-pyran-4-one and/or 2, 3-dihydro-3-hydroxy-5-isovaleryloxy-6-methyl-4H-pyran-4-one;
the molar ratio of the 2, 3-dihydro-3, 5-dihydroxy-6-methyl-4H-pyran-4-one, the organic base and the acylating agent is 1: (1-1.5): (1-2).
2. The milk-flavored tobacco sweetener of claim 1, wherein the organic solvent of step 1) is one of methylene chloride, chloroform, toluene, acetonitrile, n-hexane, tetrahydrofuran, or cyclohexane.
3. The milk-flavored tobacco sweetener of claim 1, wherein the organic base in step 2) is one of triethylamine, pyridine, or diisopropylmethylamine.
4. Use of the milk-flavored tobacco sweetener of claim 1 in cigarettes.
5. The use according to claim 4, wherein the alcoholic solution of a milk-flavored tobacco sweetener is sprayed onto tobacco shreds.
6. The use according to claim 5, wherein the milk-flavored tobacco sweetener is added in an amount of 1 to 20ppm based on the mass of the cut tobacco.
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| CN112574151A (en) * | 2020-12-10 | 2021-03-30 | 河南中烟工业有限责任公司 | 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-phenylethanol carbonate and application thereof |
| CN112574152A (en) * | 2020-12-10 | 2021-03-30 | 河南中烟工业有限责任公司 | 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-neryl carbonate and application thereof |
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| CN112552271A (en) * | 2020-12-10 | 2021-03-26 | 河南中烟工业有限责任公司 | 2, 3-dihydro-3-hydroxy-6-methyl-4H-pyran-4-one-5-O-benzyl carbonate and application thereof |
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