CN111303995A - Clathrate compound of anion ring-opening cucurbituril and nicotine substances as well as preparation method and application thereof - Google Patents
Clathrate compound of anion ring-opening cucurbituril and nicotine substances as well as preparation method and application thereof Download PDFInfo
- Publication number
- CN111303995A CN111303995A CN202010137573.4A CN202010137573A CN111303995A CN 111303995 A CN111303995 A CN 111303995A CN 202010137573 A CN202010137573 A CN 202010137573A CN 111303995 A CN111303995 A CN 111303995A
- Authority
- CN
- China
- Prior art keywords
- nicotine
- cucurbituril
- ring
- substances
- anion ring
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- MSBXTPRURXJCPF-DQWIULQBSA-N cucurbit[6]uril Chemical compound N1([C@@H]2[C@@H]3N(C1=O)CN1[C@@H]4[C@@H]5N(C1=O)CN1[C@@H]6[C@@H]7N(C1=O)CN1[C@@H]8[C@@H]9N(C1=O)CN([C@H]1N(C%10=O)CN9C(=O)N8CN7C(=O)N6CN5C(=O)N4CN3C(=O)N2C2)C3=O)CN4C(=O)N5[C@@H]6[C@H]4N2C(=O)N6CN%10[C@H]1N3C5 MSBXTPRURXJCPF-DQWIULQBSA-N 0.000 title claims abstract description 76
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 title claims abstract description 74
- 229960002715 nicotine Drugs 0.000 title claims abstract description 74
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 title claims abstract description 73
- 150000001450 anions Chemical group 0.000 title claims abstract description 56
- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 238000007142 ring opening reaction Methods 0.000 title claims abstract description 42
- 239000000126 substance Substances 0.000 title claims abstract description 36
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 241000208125 Nicotiana Species 0.000 claims abstract description 15
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 238000010438 heat treatment Methods 0.000 claims abstract description 5
- 235000019505 tobacco product Nutrition 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- 125000000129 anionic group Chemical group 0.000 claims description 21
- 238000003756 stirring Methods 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 2
- 238000001816 cooling Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims description 2
- 238000004108 freeze drying Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000843 powder Substances 0.000 claims description 2
- 238000001694 spray drying Methods 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 230000000853 biopesticidal effect Effects 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 6
- 239000000796 flavoring agent Substances 0.000 abstract description 4
- 235000019634 flavors Nutrition 0.000 abstract description 4
- 235000019504 cigarettes Nutrition 0.000 abstract description 3
- 238000013270 controlled release Methods 0.000 abstract description 3
- 239000003205 fragrance Substances 0.000 abstract description 3
- 239000003571 electronic cigarette Substances 0.000 abstract description 2
- 230000003993 interaction Effects 0.000 abstract description 2
- 239000012153 distilled water Substances 0.000 description 12
- 238000001291 vacuum drying Methods 0.000 description 11
- MTXSIJUGVMTTMU-JTQLQIEISA-N (S)-anabasine Chemical group N1CCCC[C@H]1C1=CC=CN=C1 MTXSIJUGVMTTMU-JTQLQIEISA-N 0.000 description 5
- MYKUKUCHPMASKF-VIFPVBQESA-N (S)-nornicotine Chemical group C1CCN[C@@H]1C1=CC=CN=C1 MYKUKUCHPMASKF-VIFPVBQESA-N 0.000 description 5
- MTXSIJUGVMTTMU-UHFFFAOYSA-N Neonicotine Natural products N1CCCCC1C1=CC=CN=C1 MTXSIJUGVMTTMU-UHFFFAOYSA-N 0.000 description 5
- MYKUKUCHPMASKF-UHFFFAOYSA-N Nornicotine Natural products C1CCNC1C1=CC=CN=C1 MYKUKUCHPMASKF-UHFFFAOYSA-N 0.000 description 5
- VEKIYFGCEAJDDT-UHFFFAOYSA-N 2-pyridin-3-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CN=C1 VEKIYFGCEAJDDT-UHFFFAOYSA-N 0.000 description 4
- 230000000391 smoking effect Effects 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- 239000000575 pesticide Substances 0.000 description 3
- UIKROCXWUNQSPJ-VIFPVBQESA-N (-)-cotinine Chemical compound C1CC(=O)N(C)[C@@H]1C1=CC=CN=C1 UIKROCXWUNQSPJ-VIFPVBQESA-N 0.000 description 2
- UIKROCXWUNQSPJ-UHFFFAOYSA-N Cotinine Natural products C1CC(=O)N(C)C1C1=CC=CN=C1 UIKROCXWUNQSPJ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229950006073 cotinine Drugs 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- XKABJYQDMJTNGQ-VIFPVBQESA-N n-nitrosonornicotine Chemical group O=NN1CCC[C@H]1C1=CC=CN=C1 XKABJYQDMJTNGQ-VIFPVBQESA-N 0.000 description 2
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 231100000572 poisoning Toxicity 0.000 description 2
- 230000000607 poisoning effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 108010009685 Cholinergic Receptors Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 241000208292 Solanaceae Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 102000034337 acetylcholine receptors Human genes 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000003958 fumigation Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 230000002045 lasting effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000003151 ovacidal effect Effects 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 230000002040 relaxant effect Effects 0.000 description 1
- 230000003938 response to stress Effects 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
Images
Classifications
-
- 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
-
- 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
- A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
- A24B15/26—Use of organic solvents for extraction
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention discloses an inclusion compound of anion ring-opened cucurbituril and nicotine substances, a preparation method and application thereof, wherein the nicotine substances and the anion ring-opened cucurbituril form an inclusion reaction; according to the invention, the anion ring-opening cucurbituril molecule is provided with the C-shaped cavity, so that an inclusion effect can be formed by matching the size of the cavity with nicotine substances, and meanwhile, the ionic property of the anion ring-opening cucurbituril molecule and the basic group of the nicotine substances have dipolar interaction, so that the binding property of the two substances is enhanced, and the thermal stability of the nicotine substances is enhanced. The nicotine inclusion compound can realize the slow release and the controlled release of nicotine in the application process of tobacco, tobacco products, electronic cigarettes and heating non-burning cigarettes, continuously keeps the physiological satisfaction of smokers and is safer. The inclusion compound can be applied to the industries of flavors and fragrances and tobacco.
Description
Technical Field
The invention relates to the field of preparation of tobacco flavors and fragrances, in particular to an inclusion compound of anion ring-opening cucurbituril and nicotine substances, a preparation method and application thereof.
Background
Nicotine is an alkaloid contained in Solanaceae plants (Solanum), and when smoking, nicotine is absorbed into body with smoke, enters blood, and binds with acetylcholine receptor, and has effects of exciting and relaxing, and reducing anxiety and stress response. The tobacco and the products thereof can provide the smokers with proper physiological intensity and beautiful flavor only if containing proper nicotine.
Nicotine in the cigarette is mainly derived from tobacco leaf raw materials, the nicotine content of different varieties, parts and the like of the tobacco leaf raw materials is different, and the nicotine content can be adjusted through a leaf group formula or modified through adding nicotine essence and spice; nicotine in new tobacco (including e-liquid and heated non-burning cartridges) is mainly achieved by adding free nicotine or nicotine salt extracted from tobacco; tobacco products such as reconstituted tobacco and the like also need to be added with a certain amount of nicotine substances to ensure the smoking quality. The nicotine substance is also applied to modern biological pesticides, is used for preventing and controlling pests, has the effects of contact poisoning, stomach poisoning and fumigation, and has a certain ovicidal effect.
In the smoking process of tobacco, novel tobacco and tobacco products, the externally added nicotine is volatile and has insufficient persistence, so that the smoking feeling is influenced; in the production process of tobacco products, the directly added nicotine is more lost by heating and has low processing resistance; in the use process of the nicotine pesticide, the nicotine is volatile, so the lasting period is short.
Therefore, the preparation and application of the inclusion compound of the anion ring-opening cucurbituril and the nicotine substance can effectively control the volatility and stability of nicotine in the process, realize slow release and controlled release and have practical application value, and the research of the method is not reported.
Disclosure of Invention
The invention aims to provide an anion ring-opening cucurbituril and nicotine substance clathrate compound, a preparation method and application thereof, the clathrate compound has good stability and high binding constant, and the release of nicotine substances in the clathrate compound can be realized by controlling temperature.
In order to achieve the purpose, the invention adopts the technical scheme that: a preparation method of an inclusion compound of anion ring-opened cucurbituril and nicotine substances is characterized in that the inclusion compound is formed by the inclusion reaction of the nicotine substances and the anion ring-opened cucurbituril, and the preparation method comprises the following steps: adding a type of anion ring-opening cucurbituril solid powder into a reaction kettle or a round-bottom flask, then adding a proper amount of pure water, stirring for 5-30 min at 40-100 ℃ to dissolve the solid, stopping heating and cooling to room temperature after the solid is completely dissolved, then dissolving nicotine and analogues thereof into water or an organic solvent or directly adding the nicotine and analogues thereof into a type of anion ring-opening cucurbituril solution, stirring the mixture at 20-60 ℃ for at least 6h, and then concentrating and drying under reduced pressure at 40-60 ℃, spray drying or freeze drying to obtain a nicotine substance inclusion compound; wherein the feeding molar ratio of the nicotine substance to the anionic ring-opening cucurbituril is 1-10: 1.
In a preferred embodiment of the present invention, the feeding molar ratio of the nicotine substance to the anionic ring-opened cucurbituril is 2.5: 1.
In the present invention, the anionic ring-opened cucurbiturils are selected from
Wherein R is (CH)2)nSO3Na, wherein n is 2,3 or 4.
In the invention, the structural formula of the nicotine substance is shown as
X is selected from
Namely the following substances:
further, the organic solvent is methanol, ethanol, dimethyl sulfoxide, N-dimethylformamide, acetone, chloroform or tetrahydrofuran.
The results of the clathrate of nicotine and anion ring-opened cucurbituril I, the clathrate of nornicotine and anion ring-opened cucurbituril II, and the clathrate of neonicotine and anion ring-opened cucurbituril III prepared by the preparation method are shown in figures 1-3 by using magnetic resonance hydrogen spectrum detection, and prove that the new clathrate is obtained by the method.
The thermal stability of the nicotine and anion ring-opening cucurbituril I inclusion compound prepared by the preparation method is verified at 60 ℃ and 120 ℃ respectively, and then the thermal stability is performed respectively1The HNMR researches the release degree of the nicotine substances in the inclusion compound, and the results are shown in figures 4-5, and the figure shows that the inclusion compound of the nicotine substances and the analogues thereof does not release the nicotine substances at 60 ℃ and 120 ℃, which can prove that the inclusion compound has good thermal stability.
The inclusion compound prepared by the preparation method has excellent slow release effect, can be applied to the preparation of flavors and fragrances, tobacco industry and biological pesticides, and is used as a slow release type nicotine substance, particularly the addition of nicotine in the preparation process of novel tobacco.
The beneficial technical effects of the invention are as follows: according to the invention, the anion ring-opening cucurbituril molecule is provided with the C-shaped cavity, so that an inclusion effect can be formed by matching the size of the cavity with nicotine substances, and meanwhile, the ionic property of the anion ring-opening cucurbituril molecule and the basic group of the nicotine substances have dipolar interaction, so that the binding property of the two substances is enhanced, and the thermal stability of the nicotine substances is enhanced. The nicotine inclusion compound can realize the slow release and the controlled release of nicotine in the application process of electronic cigarettes and heating non-combustible cigarettes, continuously keep the physiological satisfaction of smokers, is safer, and can be applied to the industries of essence, spice and tobacco; the preparation method is simple, convenient and feasible, has mild conditions and is suitable for industrial production.
Drawings
FIG. 1 shows the nuclear magnetic resonance hydrogen spectrum of the clathrate of nicotine and anion ring-opening cucurbituril I (I) ((1H NMR) comparison plot, wherein (a) nicotine; (b) nicotine and anion ring-opening cucurbituril clathrate compound I (the molar ratio is 1: 1); (c) nicotine and anion ring-opening cucurbituril I clathrate (molar ratio is 1: 2); (d) anion ring-opening cucurbituril I.
FIG. 2 shows NMR spectra of nornicotine and anion ring-opened cucurbituril II clathrate released at 60 deg.C for different time1H NMR) comparison plot, wherein (a) nornicotine and anionic ring-opened cucurbituril ii inclusion compounds were released at 60 ℃ for 18H; (b) the cotinine and the anion ring-opening cucurbituril II inclusion compound are released for 40min at 60 ℃; (c) untreated cotinine substances and an anion ring-opening cucurbituril II clathrate compound.
FIG. 3 shows NMR spectra of neonicotinoid and anion ring-opened cucurbituril III clathrate released at 120 deg.C for different time1H NMR) comparison plot, wherein (a) the neonicotinoid and anionic ring-opened cucurbituril iii inclusion compounds were released at 120 ℃ for 18H; (b) releasing the N-nitrosonornicotine and anion ring-opening cucurbituril III clathrate compound for 40min at 120 ℃; (c) untreated N-nitrosonornicotine and anionic ring-opened cucurbituril iii clathrates.
Figure 460 ℃ profile of nicotine release;
figure 5120 ℃ profile of nicotine release results;
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
Example 1
0.154mmol of anionic ring-opened cucurbituril I (R is (CH)2)nSO3Na, n is 3)Dissolving in 25mL of distilled water, stirring at 20 ℃ until dissolving, adding 0.16mmol of nicotine into the anion ring-opened cucurbituril solution, stirring at 25 ℃ for 7 days, performing reduced pressure concentration at 40 ℃ to remove water, and performing vacuum drying to obtain the anion ring-opened cucurbituril I and nicotine clathrate compound with the yield of 96%.
Example 2
0.154mmol of anionic ring-opened cucurbituril I (R is (CH)2)nSO3Na and n are 2), dissolving in 12mL of distilled water, stirring at 60 ℃ until the solution is dissolved, adding 0.8mmol of nornicotine into the anion ring-opened cucurbituril solution, stirring at 20 ℃ for 6h, performing reduced pressure concentration at 20 ℃ to remove water, and performing vacuum drying to obtain the clathrate of the anion ring-opened cucurbituril I and the nornicotine, wherein the yield is 97%.
Example 3
0.154mmol of anionic ring-opened cucurbituril I (R is (CH)2)nSO3Na and n are 4) is dissolved in 40mL of distilled water, the mixture is stirred to be dissolved at 40 ℃, 0.16mmol of dehydro-demethyl nicotine is added into the anion ring-opening cucurbituril solution, the mixture is stirred for 3 days at 60 ℃, water is removed by decompression and concentration at 60 ℃, and the clathrate compound of the anion ring-opening cucurbituril I and the dehydro-demethyl nicotine is prepared by vacuum drying, wherein the yield is 95%.
Example 4
0.154mmol of anionic ring-opened cucurbituril I (R is (CH)2)nSO3Na and n are 3), dissolving in 6mL of distilled water, stirring at 25 ℃ until the solution is dissolved, adding 0.16mmol of demethyldiennicotin into the anion ring-opening cucurbituril solution, stirring at 40 ℃ for 18 hours, performing reduced pressure concentration at 40 ℃ to remove water, and performing vacuum drying to obtain the inclusion compound of the anion ring-opening cucurbituril I and the demethyldiennicotin, wherein the yield is 98%.
Example 5
0.154mmol of anionic ring-opened cucurbituril II (R is (CH)2)nSO3Na and n are 3) is dissolved in 25mL distilled water, stirred at 20 deg.C until dissolved, 0.16mmol nicotine is added to the anion ring-opened cucurbituril solution, stirred at 25 deg.C for 7 days, concentrated at 40 deg.C under reduced pressure to remove water, and vacuum concentratedDrying to obtain the clathrate compound of the anion ring-opening cucurbituril II and the nicotine, wherein the yield is 99%.
Example 6
0.154mmol of anionic ring-opened cucurbituril II (R is (CH)2)nSO3Na and n are 3), dissolving in 6mL of distilled water, stirring at 25 ℃ until the solution is dissolved, adding 0.16mmol of diene nicotine into the anion ring-opening cucurbituril solution, stirring at 40 ℃ for 18 hours, performing reduced pressure concentration at 40 ℃ to remove water, and performing vacuum drying to obtain the anion ring-opening cucurbituril II and diene nicotine clathrate compound, wherein the yield is 98%.
Example 7
0.154mmol of anionic ring-opened cucurbituril II (R is (CH)2)nSO3Na and n are 2), dissolving in 12mL of distilled water, stirring at 60 ℃ until the solution is dissolved, adding 0.8mmol of neonicotine into the anion ring-opening cucurbituril solution, stirring at 20 ℃ for 6h, performing reduced pressure concentration at 20 ℃ to remove water, and performing vacuum drying to obtain the clathrate compound of the anion ring-opening cucurbituril II and the neonicotine, wherein the yield is 97%.
Example 8
0.154mmol of anionic ring-opened cucurbituril II (R is (CH)2)nSO3Na and n are 4) is dissolved in 40mL of distilled water, the mixture is stirred to be dissolved at 40 ℃, 0.16mmol of methyl neonicotinoid is added into the anion ring-opening cucurbituril solution, the mixture is stirred for 3 days at 60 ℃, water is removed by decompression and concentration at 60 ℃, and the inclusion compound of the anion ring-opening cucurbituril II and the methyl neonicotinoid is prepared by vacuum drying, wherein the yield is 98%.
Example 9
0.154mmol of anionic ring-opened cucurbituril III (R is (CH)2)nSO3Na and n are 3), dissolving in 25mL of distilled water, stirring at 20 ℃ until the solution is dissolved, adding 0.16mmol of nicotine into the anion ring-opening cucurbituril solution, stirring at 25 ℃ for 7 days, performing reduced pressure concentration at 40 ℃ to remove water, and performing vacuum drying to obtain the anion ring-opening cucurbituril III and nicotine clathrate compound with the yield of 96%.
Example 10
0.154mmol of anionic ring-opened cucurbituril III (R is (CH)2)nSO3Na and n are 2), dissolving in 12mL of distilled water, stirring at 60 ℃ until the solution is dissolved, adding 0.8mmol of denitrified nicotine into the anion ring-opened cucurbituril solution, stirring at 20 ℃ for 6h, performing reduced pressure concentration at 20 ℃ to remove water, and performing vacuum drying to obtain the clathrate compound of the anion ring-opened cucurbituril III and the denitrified nicotine, wherein the yield is 97%.
Example 11
0.154mmol of anionic ring-opened cucurbituril III (R is (CH)2)nSO3Na and N are 3), dissolving in 6mL of distilled water, stirring at 25 ℃ until the solution is dissolved, adding 0.16mmol of N-methyl denitrogenated neonicotine into the anion ring-opening cucurbituril solution, stirring at 40 ℃ for 18 hours, performing reduced pressure concentration at 40 ℃ to remove water, and performing vacuum drying to obtain the inclusion compound of the anion ring-opening cucurbituril III and the N-methyl denitrogenated neonicotine, wherein the yield is 98%.
Example 12
0.154mmol of anionic ring-opened cucurbituril III (R is (CH)2)nSO3Na and n are 4) is dissolved in 40mL of distilled water, the mixture is stirred to be dissolved at 40 ℃, 0.16mmol of 2,3 '-bipyridine is added into the anion ring-opening cucurbituril solution, the mixture is stirred for 3 days at 60 ℃, water is removed by decompression concentration at 60 ℃, and the clathrate compound of the anion ring-opening cucurbituril III and the 2, 3' -bipyridine is prepared by vacuum drying, wherein the yield is 95%.
Claims (10)
1. A preparation method of an inclusion compound of anion ring-opening cucurbituril and nicotine substances is characterized in that the inclusion compound is formed by the inclusion reaction of nicotine substances and anion ring-opening cucurbituril, and the preparation method comprises the following steps: adding a type of anion ring-opening cucurbituril solid powder into a reaction kettle or a round-bottom flask, then adding a proper amount of pure water, stirring for 5-30 min at 40-100 ℃ to dissolve the solid, stopping heating and cooling to room temperature after the solid is completely dissolved, then dissolving nicotine and analogues thereof into water or an organic solvent or directly adding the nicotine and analogues thereof into a type of anion ring-opening cucurbituril solution, stirring the mixture at 20-60 ℃ for at least 6h, and then concentrating and drying under reduced pressure at 40-60 ℃, spray drying or freeze drying to obtain a nicotine substance inclusion compound; wherein the feeding molar ratio of the nicotine substance to the anionic ring-opening cucurbituril is 1-10: 1.
2. The preparation method according to claim 1, wherein the feeding molar ratio of the nicotine-based substance to the anionic ring-opened cucurbituril is 2.5: 1.
3. The method according to claim 1, wherein the anionic ring-opened cucurbituril is selected from the group consisting of cucurbiturils
Wherein R is (CH)2)nSO3Na, wherein n is 2,3 or 4.
4. The method according to claim 1, wherein the nicotinic substance has the structural formula
5. The method according to claim 4, wherein X is selected from the group consisting of
6. The method according to claim 1, wherein the organic solvent is methanol, ethanol, dimethylsulfoxide, N-dimethylformamide, acetone, chloroform or tetrahydrofuran.
7. A clathrate compound produced by the production method described in any one of claims 1 to 6.
8. The use of the clathrate compound according to claim 7 in biopesticides.
9. Use of the inclusion compound according to claim 7 in tobacco.
10. A tobacco product comprising the inclusion compound prepared by the preparation method according to any one of claims 1 to 6.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010137573.4A CN111303995B (en) | 2020-03-02 | 2020-03-02 | Clathrate compound of anion ring-opening cucurbituril and nicotine substances as well as preparation method and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010137573.4A CN111303995B (en) | 2020-03-02 | 2020-03-02 | Clathrate compound of anion ring-opening cucurbituril and nicotine substances as well as preparation method and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN111303995A true CN111303995A (en) | 2020-06-19 |
| CN111303995B CN111303995B (en) | 2023-03-03 |
Family
ID=71152079
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010137573.4A Active CN111303995B (en) | 2020-03-02 | 2020-03-02 | Clathrate compound of anion ring-opening cucurbituril and nicotine substances as well as preparation method and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN111303995B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112362624A (en) * | 2020-11-10 | 2021-02-12 | 云南中烟工业有限责任公司 | Supermolecule fluorescence analysis method for detecting alcohol perfume compounds |
| CN114057690A (en) * | 2021-11-30 | 2022-02-18 | 昆明理工大学 | Clathrate compound of semi-cucurbit [6] uril and tobacco alkaloid, preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108771675A (en) * | 2018-07-19 | 2018-11-09 | 昆明理工大学 | The inclusion compound and preparation method thereof of artemisinin-based drug and open loop Cucurbituril |
| CN109908116A (en) * | 2019-04-09 | 2019-06-21 | 栾云鹏 | A kind of inclusion compound and preparation method thereof of cannabidiol and open loop Cucurbituril |
-
2020
- 2020-03-02 CN CN202010137573.4A patent/CN111303995B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108771675A (en) * | 2018-07-19 | 2018-11-09 | 昆明理工大学 | The inclusion compound and preparation method thereof of artemisinin-based drug and open loop Cucurbituril |
| CN109908116A (en) * | 2019-04-09 | 2019-06-21 | 栾云鹏 | A kind of inclusion compound and preparation method thereof of cannabidiol and open loop Cucurbituril |
Non-Patent Citations (1)
| Title |
|---|
| TSUYOSHI MINAMI等: "Supramolecular Sensor for Cancer-Associated Nitrosamines", 《J. AM. CHEM. SOC.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112362624A (en) * | 2020-11-10 | 2021-02-12 | 云南中烟工业有限责任公司 | Supermolecule fluorescence analysis method for detecting alcohol perfume compounds |
| CN114057690A (en) * | 2021-11-30 | 2022-02-18 | 昆明理工大学 | Clathrate compound of semi-cucurbit [6] uril and tobacco alkaloid, preparation method and application thereof |
| CN114057690B (en) * | 2021-11-30 | 2024-02-27 | 昆明理工大学 | Clathrate compound of semi-cucurbit [6] urils and tobacco alkaloids, and preparation method and application thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN111303995B (en) | 2023-03-03 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4641667A (en) | Process of preparing nicotine N'-oxide and smoking products containing it | |
| DE3874417T2 (en) | SIDE SMOKING PRODUCT CONTAINING TOBACCO. | |
| KR102642690B1 (en) | Nicotine composition, manufacturing method, and aerosol-generating article comprising the same | |
| CN111303995B (en) | Clathrate compound of anion ring-opening cucurbituril and nicotine substances as well as preparation method and application thereof | |
| US6695924B1 (en) | Method of improving flavor in smoking article | |
| US4638816A (en) | Smoking compositions containing a glycosylamine flavorant additive | |
| CN111961032A (en) | Preparation method of synthetic nicotine salt and composition thereof | |
| ES2954965T3 (en) | Liquid tobacco extract, method of manufacturing it and aerosol-generating articles comprising it | |
| US20240016199A1 (en) | Improved method of producing a liquid tobacco extract | |
| ES2965700T3 (en) | Improved method for producing a liquid tobacco extract | |
| KR20250140125A (en) | A novel tobacco product for improving sensory evaluation quality and a manufacturing method for its heating section and thick paste sheet | |
| CN105394805A (en) | Method for enabling carbon dioxide expanded tobacco to highlight sweet aroma style | |
| Burton et al. | Changes in chemical composition of burley tobacco during sensecence and curing. 2. acylated pyridine alkaloids | |
| Spiegelhalder et al. | A method for the determination of tobacco-specific nitrosamines (TSNA), nitrate and nitrite in tobacco leaves and processed tobacco | |
| US4538627A (en) | Smoking compositions containing a β-hydroxy-γ-ketoester flavorant-release additive | |
| US4532944A (en) | Smoking compositions containing a dicarbonate ester flavorant-release additive | |
| US4578486A (en) | Smoking compositions containing a dicarbonate ester flavorant-release additive | |
| EP0510817A1 (en) | Smoking compositions containing a vanillin-release additive | |
| CN110584186A (en) | Tobacco tar and preparation method thereof | |
| US4690157A (en) | Smoking compositions containing a flavorant-release additive | |
| US4540004A (en) | Smoking compositions containing a flavorant-release additive | |
| US4538628A (en) | Smoking compositions containing a dioxane diester flavorant-release additive | |
| US4872918A (en) | Heterocyclic esters and smoking compositions containing a heterocyclic ester flavorant-release additive | |
| EP0514202A2 (en) | Smoking compositions containing a vanillin-release additive | |
| CN1256900C (en) | A method for treating latent aroma of shredded tobacco leaves and its application |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |