CN106478418A - The cigarette preparation method and applications of latent perfume 3 cinnamic acid esters of monomer - Google Patents
The cigarette preparation method and applications of latent perfume 3 cinnamic acid esters of monomer Download PDFInfo
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- CN106478418A CN106478418A CN201610880146.9A CN201610880146A CN106478418A CN 106478418 A CN106478418 A CN 106478418A CN 201610880146 A CN201610880146 A CN 201610880146A CN 106478418 A CN106478418 A CN 106478418A
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- Prior art keywords
- cigarette
- cinnamic acid
- ionol
- monomer
- esters
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- 235000019504 cigarettes Nutrition 0.000 title claims abstract description 37
- 239000002304 perfume Substances 0.000 title claims abstract description 18
- 239000000178 monomer Substances 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- 150000001851 cinnamic acid derivatives Chemical class 0.000 title abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000007788 liquid Substances 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims abstract description 13
- 239000012074 organic phase Substances 0.000 claims abstract description 12
- CNOPDZWOYFOHGN-BQYQJAHWSA-N Beta-Ionol Chemical compound CC(O)\C=C\C1=C(C)CCCC1(C)C CNOPDZWOYFOHGN-BQYQJAHWSA-N 0.000 claims abstract description 11
- CNOPDZWOYFOHGN-UHFFFAOYSA-N beta-ionol Natural products CC(O)C=CC1=C(C)CCCC1(C)C CNOPDZWOYFOHGN-UHFFFAOYSA-N 0.000 claims abstract description 11
- 235000013985 cinnamic acid Nutrition 0.000 claims abstract description 11
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims abstract description 11
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims abstract description 10
- 229930016911 cinnamic acid Natural products 0.000 claims abstract description 10
- 239000012043 crude product Substances 0.000 claims abstract description 9
- -1 ethyl (3 dimethylaminopropyl) Chemical group 0.000 claims abstract description 8
- 239000007832 Na2SO4 Substances 0.000 claims abstract description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 6
- 239000007864 aqueous solution Substances 0.000 claims abstract description 6
- 238000012544 monitoring process Methods 0.000 claims abstract description 6
- 229910052938 sodium sulfate Inorganic materials 0.000 claims abstract description 6
- 238000005406 washing Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 238000004440 column chromatography Methods 0.000 claims abstract description 5
- 238000000926 separation method Methods 0.000 claims abstract description 5
- 150000003839 salts Chemical class 0.000 claims abstract description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 24
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 241000208125 Nicotiana Species 0.000 claims description 13
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 13
- 239000003208 petroleum Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 239000007791 liquid phase Substances 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 238000003756 stirring Methods 0.000 abstract description 4
- 239000000779 smoke Substances 0.000 abstract description 3
- DXRFZHILMCWCNG-UHFFFAOYSA-N N,N-dimethyl-1,8-naphthyridin-2-amine Chemical class C1=CC=NC2=NC(N(C)C)=CC=C21 DXRFZHILMCWCNG-UHFFFAOYSA-N 0.000 abstract 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 17
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000001460 carbon-13 nuclear magnetic resonance spectrum Methods 0.000 description 4
- 235000019634 flavors Nutrition 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 230000006837 decompression Effects 0.000 description 3
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 3
- 229910000071 diazene Inorganic materials 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- 238000010898 silica gel chromatography Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000013068 control sample Substances 0.000 description 2
- 230000009189 diving Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 235000013599 spices Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical class OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 230000007073 chemical hydrolysis Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000003546 flue gas Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 229960002715 nicotine Drugs 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000000197 pyrolysis Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- 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
- A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A kind of cigarette preparation method of latent perfume 3 cinnamic acid esters of monomer, comprises the steps：Take 3 cinnamic acids and β ionol is dissolved in dry dichloromethane, stirring 10min 30min, 4 dimethylamino naphthyridines and 1 ethyl (3 dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate is added, 4 12h, TLC monitoring reaction is stirred at room temperature, tracking reaction end, add water in organic phase washing, point liquid, then is washed with saturated nacl aqueous solution, divide liquid, organic phase anhydrous Na2SO4Dry, crude product is concentrated to give, column chromatography for separation is carried out, that is, obtain 3 cinnamic acid β ionol esters.The present invention prepares 3 cinnamic acid β ionol esters compared with β ionol parent thing, it is remarkably improved the addition in cigarette, the outer perfume kind of cigarette is not affected, is applied in cigarette to reduce the excitant of cigarette and miscellaneous gas, improves the mellow and full sense of cigarette smoke and comfortableness.
Description
Technical field
The present invention relates to essence and flavoring agent and tobacco manufacture field, specifically a kind of cigarette perfume monomer 3- cinnamic acid esters of diving
Preparation method and applications.
Background technology
Many excellent spices are as its high high-temp stability is poor, volatility is limited the problems such as short compared with strong, fragrance remaining time
Which is widely applied.Latent Studies of The Aromatic Substances is the material that a class relative molecular mass is big, boiling point is higher, and fragrance is less or does not have perfume (or spice) in itself
Gas, but can discharge with fragrance fragrance through the approach such as chemical hydrolysis, enzymolysis or microbial action, pyrolysis, photodestruciton
Compound.Because of its security preferably, natural perfume material category is listed in the world in, with its some local flavor flavoring essence effect of allotment
Very well.Different from volatility and half volatile fragrance matter, perfume class of diving compound is reducing artificial flavor and taste compensation vestige
While the significant changes of the material delivering amount such as nicotine in cigarette mainstream flue gas, tar are not result in, more longlasting cigarette can be stably provided
Gas characteristic chicken flavor.In prior art, latent Studies of The Aromatic Substances is widely applied in the adding technology of cigarette shreds, and the present invention provides one
Preparation method of the cigarette with latent perfume monomer benzenpropanoic acid esters is planted, and inquires into its application in perfuming cigarette.
Content of the invention
The present invention provides a kind of cigarette with latent perfume monomer 3- cinnamic acid esters to develop new cigarette flavor precursors
Preparation method and its application in cigarette.
For achieving the above object, the present invention is adopted the following technical scheme that：
A kind of cigarette preparation method of monomer perfume 3- bezene acrylic acid, which comprises the steps：
Take 3- cinnamic acid and β-ionol is dissolved in dry dichloromethane, 10min-30min is stirred, add 4- bis-
Methylamino pyridine (DMAP) and 1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate (EDCHCl), are stirred at room temperature
4-12h, TLC monitoring reaction, tracks reaction end, and add water in organic phase washing, point liquid, then is washed with saturated nacl aqueous solution
Wash, point liquid, organic phase anhydrous Na2SO4Dry, crude product is concentrated to give, then column chromatography for separation is carried out, obtain the cigarette single
Body note material 3- bezene acrylic acid, i.e. 3- cinnamic acid-β-ionol esters, its structural formula is shown in formula I.
Further, described column chromatography for separation eluent is the mixing of ethyl acetate and petroleum ether, both volume ratios
100:1-20:1.
Further, the molar ratio of described 3- cinnamic acid and β-ionol is 0.9:1-1:Between 0.9.
Further, application of the 3- cinnamic acid-β-ionol esters as fragrance-enhancing tobacco agent in cigarette, by which
It is applied in cigarette as fragrance-enhancing tobacco agent, addition is the 0.01-0.10% of pipe tobacco weight.
The compounds of this invention 3- cinnamic acid-β-ionol esters are a kind of latent aroma compounds, and under normal temperature, which is stable in properties,
For colourless liquid, but which passes through to heat cleavable and produces tool and be significantly increased tobacco aroma material, such as 3- oxo-beta-violet
Ketone.
Compared to the prior art, beneficial effects of the present invention：
1. the present invention prepares 3- cinnamic acid-β-ionol esters compared with β-ionol parent thing, significantly can improve
Addition in cigarette, and do not affect the outer perfume kind of cigarette.
2. the present invention with DMAP/1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate is
3- cinnamic acid and β-ionol esterification reaction condensation reagent, can significantly improve reaction yield, simplify aftertreatment technology.
3. the 3- cinnamic acid-β that the present invention is developed-ionol esters cigarette monomer perfume, first as tobacco
Fumet is applied in cigarette, it is possible to decrease the excitant of cigarette and miscellaneous gas, improves the mellow and full sense of cigarette smoke and comfortableness.
Description of the drawings
Fig. 1 is 3- cinnamic acid-β-ionol esters 1H NMR nuclear magnetic spectrogram；
Fig. 2 is-cinnamic acid-β-ionol esters 13C NMR nuclear magnetic spectrogram；
Fig. 3 is-cinnamic acid-β-ionol esters HRMS high-resolution spectrogram.
Specific embodiment
With reference to specific embodiment, the present invention is described in further detail, is easy to be well understood to the interior of the present invention
Hold, but they do not constitute to the present invention and limit.
Embodiment one
The preparation method of tobacco aromaticss monomer 3- cinnamic acid-β-ionol esters：
Take 10mmol β-ionol and 10mmol 3- cinnamic acid is dissolved in the dichloromethane of 100ml drying, stirring
After 10min, DMAP (DMAP) (5mmol) and 1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimine is added
Hydrochloride (EDCHCl) (11mmol), is stirred at room temperature, TLC monitoring reaction (petroleum ether：Ethyl acetate=10:1, Rf=0.5, purple
Outer 254nm colour developing), track reaction end.The 50mL that adds water in organic phase is washed, point liquid, then uses 50mL saturated nacl aqueous solution
Washing, point liquid, organic phase anhydrous Na2SO4Dry, be concentrated to give crude product.Crude product 50mL dichloromethane dissolves, and adds
The silica gel 4g of 100-200 mesh, decompression are spin-dried for mixing sample, use petroleum ether in the silica gel column chromatography strain with 80g 100-200 mesh：Ethyl acetate
=60:1 slowly elutes, concentrate, dry after obtain target product.
Embodiment two
The preparation method of tobacco aromaticss monomer 3- cinnamic acid-β-ionol esters：
Take 10mmol β-ionol and 10.5mmol 3- cinnamic acid is dissolved in the dichloromethane of 100ml drying, stirring
After 10min, DMAP (DMAP) (4mmol) and 1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimine is added
Hydrochloride (EDCHCl) (11mmol), is stirred at room temperature, TLC monitoring reaction (petroleum ether：Ethyl acetate=10:1, Rf=0.5, purple
Outer 254nm colour developing), track reaction end.The 50mL that adds water in organic phase is washed, point liquid, then uses 50mL saturated nacl aqueous solution
Washing, point liquid, organic phase anhydrous Na2SO4Dry, be concentrated to give crude product.Crude product 50mL dichloromethane dissolves, and adds
The silica gel 4g of 100-200 mesh, decompression are spin-dried for mixing sample, use petroleum ether in the silica gel column chromatography strain with 80g 100-200 mesh：Ethyl acetate
=60:1 slowly elutes, concentrate, dry after obtain target product.
Embodiment three
The preparation method of tobacco aromaticss monomer 3- cinnamic acid-β-ionol esters：
Take 10.5mmol β-ionol and 10mmol 3- cinnamic acid is dissolved in the dichloromethane of 100ml drying, stirring
After 10min, DMAP (DMAP) (6mmol) and 1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimine is added
Hydrochloride (EDCHCl) (12mmol), is stirred at room temperature, TLC monitoring reaction (petroleum ether：Ethyl acetate=10:1, Rf=0.5, purple
Outer 254nm colour developing), track reaction end.The 50mL that adds water in organic phase is washed, point liquid, then uses 50mL saturated nacl aqueous solution
Washing, point liquid, organic phase anhydrous Na2SO4Dry, be concentrated to give crude product.Crude product 50mL dichloromethane dissolves, and adds
The silica gel 4g of 100-200 mesh, decompression are spin-dried for mixing sample, use petroleum ether in the silica gel column chromatography strain with 80g 100-200 mesh：Ethyl acetate
=60:1 slowly elutes, concentrate, dry after obtain target product.
(1) structural characterization of target product
By red high resolution mass spectrum (HR-MS), carbon-13 nmr spectra (1H-NMR 13C-NMR) respectively to embodiment gained
Target product 3- cinnamic acid-β-ionol esters carry out structural characterization, and concrete data are following (as Figure 1-3)：
3- cinnamic acid-β-ionol esters：Colourless oil liquid.1H NMR(400MHz,CDCl3)δppm 7.68(d,J
=15.98Hz, 1H), 7.56-7.49 (m, 2H), 7.38 (d, J=2.20Hz, 3H), 6.45 (d, J=16.02Hz, 1H), 6.16
(d, J=15.40Hz, 1H), 5.58-5.43 (m, 2H), 1.97 (t, J=5.91,5.91Hz, 2H), 1.66 (s, 3H), 1.64-
1.54 (m, 2H), 1.49-1.38 (m, 6H), 0.99 (d, J=2.90Hz, 6H)；13C NMR(400MHz,CDCl3)δ
ppm166.28,144.39,136.57,134.55,132.89,130.16,130.07,129.10,128.86,128.06,
118.76,71.79,39.36,33.92,32.67,28.68,21.35,20.73,19.247.[M+Na]+found 347.1985
(calcd.347.1987).
Analyze from spectrum elucidation, in conjunction with infrared spectrum (IR), high resolution mass spec (1HR-MS) and carbon-13 nmr spectra
(13C-NMR) can determine that gained compound is 3- cinnamic acid-β-ionol esters.
(2) perfuming research of the target product in tobacco
With 95% ethanol as solvent, target product 3- cinnamic acid-β-ionol esters are made into the molten of mass fraction 1%
Liquid.0.5g, 1.0g, 5.0g, 10.0g and 15.0g above-mentioned solution containing target product is taken respectively, and then uniform spray is added to five parts not
In the 100g blank cigarette shreds of flavoring and casing, roll, 100 same weight cigarette are respectively picked out, be placed in temperature 22 DEG C ± 1
DEG C, 48h is balanced in the climatic chamber of humidity 60% ± 2%, smoke panel test.Control sample is blank cigarette, and control sample is equally identical
48h is balanced under the conditions of epidemic disaster.
The perfuming smoking result of 1 3- cinnamic acid-β of table-ionol esters
The above, the only specific embodiment of the present invention, but protection scope of the present invention is not limited thereto, and any
Belong to those skilled in the art the invention discloses technical scope in, the change or replacement that can readily occur in, all answer
It is included within the scope of the present invention.Therefore, protection scope of the present invention should be defined by scope of the claims.
Claims (4)
1. a kind of cigarette preparation method and applications of latent perfume monomer 3- cinnamic acid esters, it is characterised in that including following step
Suddenly：
Take 3- cinnamic acid and β-ionol is dissolved in dry dichloromethane, 10min-30min is stirred, add 4- diformazan ammonia
Yl pyridines and 1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate, are stirred at room temperature 4-12h, TLC monitoring reaction,
Tracking reaction end, add water in organic phase washing, point liquid, then is washed with saturated nacl aqueous solution, divides liquid, and organic phase is with anhydrous
Na2SO4Dry, crude product is concentrated to give, then column chromatography for separation is carried out, the cigarette monomer perfume 3- bezene acrylic acid is obtained, i.e.,
3- cinnamic acid-β-ionol esters, its structural formula is shown in formula I：
2. cigarette as claimed in claim 1 preparation method and applications of latent perfume monomer 3- cinnamic acid esters, its feature exist
In：Described column chromatography for separation eluent is the mixing of ethyl acetate and petroleum ether, both volume ratios 100:1-20:1.
3. cigarette as claimed in claim 1 preparation method and applications of latent perfume monomer 3- cinnamic acid esters, its feature exist
In：The molar ratio of described 3- cinnamic acid and β-ionol is 0.9:1-1:Between 0.9.
4. a kind of cigarette as the arbitrary methods described preparation of claim 1-3 is increased as tobacco with latent perfume monomer 3- cinnamic acid esters
Application of the pastil in cigarette, is applied in cigarette as fragrance-enhancing tobacco agent, and addition is the 0.01- of pipe tobacco weight
0.10%.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113876022A (en) * | 2021-09-20 | 2022-01-04 | 河南中烟工业有限责任公司 | High-molecular latent-fragrance slow-release material and application thereof in heating cigarettes |
| CN115141131A (en) * | 2021-03-30 | 2022-10-04 | 湖北中烟工业有限责任公司 | 3,4-diacetyl-2,5-dimethylpyrrole compound and preparation method and application thereof |
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