CN115448884B - Cooling agent for tobacco products and preparation method and application thereof - Google Patents
Cooling agent for tobacco products and preparation method and application thereof Download PDFInfo
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- CN115448884B CN115448884B CN202211282251.4A CN202211282251A CN115448884B CN 115448884 B CN115448884 B CN 115448884B CN 202211282251 A CN202211282251 A CN 202211282251A CN 115448884 B CN115448884 B CN 115448884B
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- cooling agent
- tobacco product
- heated non
- menthol
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- 239000002826 coolant Substances 0.000 title claims abstract description 45
- 235000019505 tobacco product Nutrition 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title abstract description 8
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims abstract description 23
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims abstract description 21
- 229940041616 menthol Drugs 0.000 claims abstract description 21
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 239000003054 catalyst Substances 0.000 claims description 9
- 150000007530 organic bases Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 5
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- 230000035484 reaction time Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 abstract description 12
- LFKYBJLFJOOKAE-UHFFFAOYSA-N imidazol-2-ylidenemethanone Chemical compound O=C=C1N=CC=N1 LFKYBJLFJOOKAE-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000779 smoke Substances 0.000 abstract description 8
- 230000000391 smoking effect Effects 0.000 abstract description 7
- 241000208125 Nicotiana Species 0.000 abstract description 6
- 235000002637 Nicotiana tabacum Nutrition 0.000 abstract description 6
- 239000003205 fragrance Substances 0.000 abstract description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 32
- 235000019504 cigarettes Nutrition 0.000 description 19
- 238000005481 NMR spectroscopy Methods 0.000 description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000001953 sensory effect Effects 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 239000000796 flavoring agent Substances 0.000 description 3
- 235000019634 flavors Nutrition 0.000 description 3
- 238000004896 high resolution mass spectrometry Methods 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 230000006978 adaptation Effects 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000002045 lasting effect Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 235000019640 taste Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- 238000004252 FT/ICR mass spectrometry Methods 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia Nutrition 0.000 description 1
- BLILOGGUTRWFNI-UHFFFAOYSA-N Monomenthyl succinate Chemical compound CC(C)C1CCC(C)CC1OC(=O)CCC(O)=O BLILOGGUTRWFNI-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000005485 electric heating Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- -1 imidazole compound Chemical class 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- 238000012827 research and development Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B9/00—Essential oils; Perfumes
- C11B9/0069—Heterocyclic compounds
- C11B9/0092—Heterocyclic compounds containing only N as heteroatom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacture Of Tobacco Products (AREA)
Abstract
The invention discloses a tobacco product cooling agent, a preparation method and application thereof, and belongs to the technical field of tobacco cooling agents. The cooling agent has a structure shown in a formula I, and the colorless oily menthoxy carbonyl imidazole cooling agent is obtained by introducing a carbonyl imidazole structure into menthol. The cooling agent has slow fragrance release and easy addition, and can provide cooling with longer duration, depth and impact force. The cooling agent is added into the heated non-combustible tobacco products, so that the smoke quality can be improved, and the smoking experience of people can be improved.
Description
Technical Field
The invention relates to the technical field of tobacco cooling agents, in particular to a tobacco product cooling agent, a preparation method and application thereof.
Background
The heated non-combustible cigarette is heated to 200-400 ℃ by the electric heating device to the atomized substrate section thereof, thereby producing a sensory feel similar to that of a conventional cigarette. The heated temperature of tobacco is significantly reduced relative to the conventional cigarette combustion temperatures (typically in excess of 800 ℃). The lower suction temperature greatly reduces the release of tar and harmful substances generated at high temperature, meets the health requirements of people, and gradually becomes a research and development hot spot of tobacco companies.
At present, the types of heated non-combustible tobacco products are few, and compared with the traditional cigarettes, certain differences exist in quantity, types and quality, and the problems of fog (smoke concentration and release), aroma (aroma flavor and release), taste (mouthfeel) and the like of the products are mainly manifested. Among other features, aroma flavor and release uniformity significantly affect the smoking experience and largely determine the quality of the heated non-combusted tobacco product, so people often improve the quality of the heated non-combusted tobacco product by optimizing the aroma flavor and release characteristics.
The cooling agent for cigarettes is a general term of chemical substances which are used for various cigarette products to generate cooling effect and have weak drug properties, can be used as an important additive of mint cigarettes, can mask the bitter taste of the cigarettes, can refresh the taste, can improve the harmony and softness of the cigarette smoke, can reduce the irritation of the oral cavity and the throat, and can greatly improve the smoking experience of people, so that the cooling agent for cigarettes has wide application in the cigarette industry.
The existing cooling agent for cigarettes mainly comprises menthol and derivatives thereof, such as monomenthyl succinate, dimenthyl malate, WS series cooling agents and the like. Wherein, compared with menthol, the cooling agent of menthol derivative has longer cooling time and deeper cooling feeling, and can provide cooling without fragrance or with weak fragrance but stronger impact force. Therefore, developing a menthol derivative cooling agent suitable for heating non-combustible cigarettes is important to improve the smoke quality of the heated non-combustible tobacco products and the smoking experience of people.
Disclosure of Invention
In view of the above, the technical problem to be solved by the invention is to provide a tobacco product cooling agent, and a preparation method and application thereof. The cooling agent can provide cooling with longer lasting, deep and impact force.
In order to achieve the above purpose, the invention adopts the following technical scheme:
the invention provides a cooling agent for tobacco products, which has a structure shown in a formula I:
the chemical name of the compound with the structure shown in the formula I is menthoxycarbonyl imidazole. By introducing the carbonyl imidazole structure on menthol, the fragrance of the cooling agent is slowly released, and cooling with longer duration, depth and impact force can be provided.
The invention provides a preparation method of a tobacco product cooling agent, which comprises the steps of mixing menthol and N, N' -carbonyl diimidazole, and reacting under the action of an organic base catalyst to obtain the cooling agent.
The preparation method of the tobacco product cooling agent provided by the invention comprises the following specific steps:
1) Uniformly mixing menthol and N, N' -carbonyl diimidazole to obtain a mixed system;
2) And adding an organic base catalyst into the mixed system to perform condensation reaction to obtain the cooling agent.
The reaction equation of the reaction is:
the order of mixing in step 1) of the above-mentioned production method is not particularly limited.
In the specific embodiment of the invention, menthol is firstly dissolved in a reaction solvent, and then N, N' -carbonyl diimidazole is slowly added to fully mix the menthol and the reaction solvent.
Preferably, the molar ratio of menthol to N, N' -carbonyl diimidazole is 1: (1-4).
Preferably, the reaction solvent is selected from one or more of dichloromethane, ethyl acetate, tetrahydrofuran, toluene and acetonitrile.
In a specific embodiment of the present invention, the reaction solution is ethyl acetate.
Preferably, the organic base catalyst is selected from one or more of pyridine, 4-dimethylaminopyridine and triethylamine.
Preferably, the molar ratio of the organic base catalyst to menthol is 1: (10-100).
In a specific embodiment of the invention the organic base catalyst is pyridine, and the molar ratio of pyridine to menthol is 1:20.
Preferably, the temperature of the reaction is room temperature, specifically 20-50 ℃.
Preferably, the reaction time is 2-3 h.
The invention also provides application of the menthoxycarbonyl imidazole compound shown in the formula I as a cooling agent of tobacco products.
Preferably, the tobacco product of the present invention is a heated non-combustible tobacco product. The cooling agent is added into the heated non-combustible tobacco product, so that smoke with lasting cooling and more coordination can be provided.
The invention also provides a heated non-combustible tobacco product comprising a heated non-combustible tobacco product and a cooling agent added to the heated non-combustible tobacco product.
Preferably, the cooling agent is the cooling agent or the cooling agent prepared by the preparation method.
Compared with the prior art, the invention obtains the colorless oily menthoxy carbonyl imidazole cooling agent by introducing the carbonyl imidazole structure on menthol. The cooling agent has slow fragrance release and easy addition, and can provide cooling with longer duration, depth and impact force. The cooling agent is added into the heated non-combustible tobacco products, so that the smoke quality can be obviously improved, and the smoking experience of people is improved.
Drawings
FIG. 1 is a high resolution mass spectrum of menthoxycarbonyl imidazole;
FIG. 2 is a 1 H NMR chart of menthoxycarbonyl imidazole;
FIG. 3 is a 13 C NMR chart of menthoxycarbonyl imidazole.
Detailed Description
Menthol, N' -carbonyl diimidazole, ethyl acetate and pyridine as organic base catalysts are all commercial products.
In order to further illustrate the present invention, the cooling agent for heating non-combustible tobacco products and the method for preparing the same according to the present invention are described in detail below with reference to examples.
Example 1
Adding 10mmol of menthol into a 100mL round-bottom flask, continuously adding 40mL of ethyl acetate serving as a reaction solvent, magnetically stirring under ice bath until the menthol is completely dissolved, slowly adding 12mmol of N, N' -Carbonyldiimidazole (CDI) into the reaction system, dissolving 0.5mmol of pyridine (Py) with 10mL of ethyl acetate, dripping into the round-bottom flask within 5 minutes, removing the ice bath to room temperature for reaction, after TLC detection reaction is complete, washing the reaction liquid with water, concentrating, and distilling under reduced pressure to obtain colorless viscous liquid, namely menthoxycarbonyl imidazole, wherein the yield is 89%, and the purity is 98%.
Characterization data for the product structure are as follows:
1) High resolution mass spectrometry (HR-MS) analysis:
HR-MS of the product menthoxycarbonyl imidazole was measured on a Bruker En Apex ultra 7.0.0 FT-MS mass spectrometer.
The mass-to-charge ratio of menthoxycarbonyl imidazole is shown in fig. 1, and the mass-to-charge ratio of menthoxycarbonyl imidazole is: [ M+H ] + M/z251.1760.
2) Nuclear magnetic resonance hydrogen spectrum analysis of the product:
the nuclear magnetic resonance hydrogen spectrum of the menthoxycarbonyl imidazole is obtained through a nuclear magnetic resonance apparatus Bruker AV400 superconducting nuclear magnetic resonance apparatus test.
The analysis result of the nuclear magnetic resonance hydrogen spectrum is shown in the figure 2：1H NMR(400MHz,Chloroform-d)δ8.06(s,1H),7.36(s,1H),6.99(s,1H),4.85-4.79(m,1H),2.11-2.09(m,1H),1.88-1.83(m,1H),1.70-1.66(m,2H),1.51-1.46(m,2H),1.13-1.00(m,2H),0.89-0.76(m,7H),0.75(d,J＝6.99Hz,3H).
3) Nuclear magnetic resonance carbon spectrum analysis of the product:
the nuclear magnetic resonance carbon spectrum of the menthoxycarbonyl imidazole is obtained by testing with a nuclear magnetic resonance apparatus Bruker AV400 superconducting nuclear magnetic resonance apparatus.
The analysis result of nuclear magnetic resonance carbon spectrum is shown in the figure 3：13C NMR(101MHz,Chloroform-d)δ148.3,137.0,130.5,117.1,79.4,47.0,40.6,33.9,31.4,26.5,23.5,21.9,20.6,16.4.
Example 2
The menthoxy carbonyl imidazole cooling agent is dissolved in food grade ethanol, added into the tobacco powder according to the proportion of 0.02wt%, pressed into tablets, cut into threads and made into the heating non-burning cigarettes, and the heating non-burning cigarettes added with the menthoxy carbonyl imidazole cooling agent are found through professional smoking, so that the cooling effect is obvious and durable, the release is uniform and consistent before and after release, the smoke is smooth, and the aroma is coordinated.
Comparative example 1
The menthol cooling agent is dissolved in food grade ethanol, added into the tobacco powder according to the proportion of 0.02wt%, pressed into tablets, shredded into filaments and made into the heated non-combustible cigarettes, and the special evaluation shows that the heated non-combustible cigarettes added with the menthol cooling agent have insignificant cooling effect and short holding time.
The professional smoker refers to national standard (sensory technical requirements) GB5606.4-2005, and performs sensory quality scoring according to the characteristics of the heated non-combustible cigarettes, and the results are shown in Table 1.
TABLE 1
The above results were taken as an average of the sensory quality scores of 7 professional panelists.
In conclusion, the menthoxy carbonyl imidazole cooling agent effectively improves the effect of the cooling agent by introducing carbonyl imidazole groups into menthol, and can provide cooling with longer duration, depth and impact force. The cooling agent is added into the heated non-combustible cigarettes, so that the smoke quality can be improved, and the smoking experience of people can be improved.
The above description of the embodiments is only for aiding in the understanding of the method of the present invention and its core ideas. It should be noted that it will be apparent to those skilled in the art that various modifications and adaptations of the invention can be made without departing from the principles of the invention and these modifications and adaptations are intended to be within the scope of the invention as defined in the following claims.
Claims (7)
1. A heated non-combustible tobacco product comprising a heated non-combustible tobacco product and a cooling agent added to the heated non-combustible tobacco product;
The cooling agent has a structure shown in formula I:
2. The heated non-combustible tobacco product of claim 1 wherein the cooling agent is prepared according to the following method:
mixing menthol and N, N' -carbonyl diimidazole, and reacting under the action of an organic base catalyst to obtain the cooling agent.
3. The heated non-combusted tobacco product of claim 2, wherein said menthol to N, N' -carbonyldiimidazole molar ratio is 1: (1-4).
4. The heated non-combustible tobacco product of claim 2 wherein the reaction solvent is selected from one or more of dichloromethane, ethyl acetate, tetrahydrofuran, toluene, acetonitrile.
5. The heated non-combustible tobacco product of claim 2 wherein the organic base catalyst is selected from one or more of pyridine, 4-dimethylaminopyridine, triethylamine;
The molar ratio of the organic base catalyst to menthol is 1: (10-100).
6. The heated non-combustible tobacco product of claim 2 wherein the temperature of the reaction is room temperature.
7. A heated non-combustible tobacco product according to claim 2 in which the reaction time is from 2 to 3 hours.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211282251.4A CN115448884B (en) | 2022-10-19 | 2022-10-19 | Cooling agent for tobacco products and preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202211282251.4A CN115448884B (en) | 2022-10-19 | 2022-10-19 | Cooling agent for tobacco products and preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN115448884A CN115448884A (en) | 2022-12-09 |
| CN115448884B true CN115448884B (en) | 2024-04-26 |
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| CN202211282251.4A Active CN115448884B (en) | 2022-10-19 | 2022-10-19 | Cooling agent for tobacco products and preparation method and application thereof |
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Citations (6)
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|---|---|---|---|---|
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| CN101486645A (en) * | 2008-01-18 | 2009-07-22 | 河南中烟工业公司 | Flavouring essences for tobacco and preparation thereof |
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2022
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| Title |
|---|
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| CN115448884A (en) | 2022-12-09 |
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