CN106478418B - The preparation method and applications of the latent fragrant monomer 3- cinnamic acid esters of cigarette - Google Patents
The preparation method and applications of the latent fragrant monomer 3- cinnamic acid esters of cigarette Download PDFInfo
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- CN106478418B CN106478418B CN201610880146.9A CN201610880146A CN106478418B CN 106478418 B CN106478418 B CN 106478418B CN 201610880146 A CN201610880146 A CN 201610880146A CN 106478418 B CN106478418 B CN 106478418B
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- ionol
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- 235000019504 cigarettes Nutrition 0.000 title claims abstract description 37
- 239000000178 monomer Substances 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 27
- 238000000926 separation method Methods 0.000 claims abstract description 17
- 239000007788 liquid Substances 0.000 claims abstract description 15
- 238000006243 chemical reaction Methods 0.000 claims abstract description 12
- 239000012074 organic phase Substances 0.000 claims abstract description 12
- 235000013985 cinnamic acid Nutrition 0.000 claims abstract description 11
- 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 10
- CNOPDZWOYFOHGN-UHFFFAOYSA-N beta-ionol Natural products CC(O)C=CC1=C(C)CCCC1(C)C CNOPDZWOYFOHGN-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000012043 crude product Substances 0.000 claims abstract description 9
- 238000005406 washing Methods 0.000 claims abstract description 9
- 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
- 238000003756 stirring 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
- 239000000654 additive Substances 0.000 claims abstract description 4
- 230000000996 additive effect Effects 0.000 claims abstract description 4
- 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
- 241000208125 Nicotiana Species 0.000 claims description 13
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 8
- 239000002304 perfume Substances 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 5
- 150000001253 acrylic acids Chemical class 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
- 238000000034 method Methods 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 claims 1
- 230000007794 irritation Effects 0.000 abstract description 2
- 239000000779 smoke Substances 0.000 abstract description 2
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 abstract 3
- -1 ethyl (3 dimethylaminopropyl) Chemical group 0.000 abstract 3
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 abstract 2
- 229930016911 cinnamic acid Natural products 0.000 abstract 2
- 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
- 150000001851 cinnamic acid derivatives Chemical class 0.000 abstract 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 8
- 239000000796 flavoring agent Substances 0.000 description 6
- 239000003205 fragrance Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 235000019634 flavors Nutrition 0.000 description 5
- 239000000126 substance 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
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 206010013786 Dry skin Diseases 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
- 150000002170 ethers Chemical class 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
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000463 material 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
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical class CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-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
- 230000009189 diving 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
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 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
- SVEUVITYHIHZQE-UHFFFAOYSA-N n-methylpyridin-2-amine Chemical compound CNC1=CC=CC=N1 SVEUVITYHIHZQE-UHFFFAOYSA-N 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 3 cinnamic acid esters of latent fragrant monomer, includes the following steps：3 cinnamic acids and β ionols are taken to be dissolved in dry dichloromethane, stir 10min 30min, 4 dimethylamino naphthyridines and 1 ethyl (3 dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate are added, 4 12h, TLC monitoring reactions is stirred at room temperature, track reaction end, add water washing, liquid separation into organic phase, then is washed with saturated nacl aqueous solution, liquid separation, organic phase anhydrous Na2SO4It is dry, it is concentrated to give crude product, carries out column chromatography for separation to get to 3 cinnamic acid β ionol esters.The present invention prepares 3 cinnamic acid β ionol esters compared with β ionol parent objects, it is remarkably improved the additive amount in cigarette, the outer fragrant kind for not influencing cigarette improves the mellow and full sense of cigarette smoke and comfort applied to the irritation and miscellaneous gas that can reduce cigarette in cigarette.
Description
Technical field
The present invention relates to essence and flavoring agent and tobacco manufacture field, the latent fragrant monomer 3- cinnamic acid esters of specifically a kind of cigarette
Preparation method and applications.
Background technology
Many excellent fragrance due to its high high-temp stability is poor, volatility compared with strong, fragrance remaining time is short the problems such as limit
It is widely applied.Latent Studies of The Aromatic Substances is that a kind of relative molecular mass is big, the higher substance of boiling point, and fragrance is less or itself is without perfume
Gas, but can be released with fragrance fragrance by the approach such as chemical hydrolysis, enzymolysis or microbial action, pyrolysis, photodestruciton
Compound.Because its safety is preferable, it is included in natural perfume material scope in the world, certain flavor food flavor effects are allocated with it
Very well.Different from volatility and half volatile fragrance matter, perfume class compound of diving is reducing artificial flavor and taste compensation trace
It will not lead to the significant changes of the substances delivering amount such as nicotine in cigarette mainstream flue gas, tar simultaneously, it can more longlasting stable offer cigarette
Gas characteristic chicken flavor.In the prior art, latent Studies of The Aromatic Substances is widely applied in the adding technology of cigarette shreds, and the present invention provides one
The preparation method of the latent fragrant monomer benzenpropanoic acid esters of kind cigarette, and inquire into its application in perfuming cigarette.
Invention content
The present invention provides a kind of cigarette latent fragrant monomer 3- cinnamic acid esters to develop novel cigarette flavor precursors
Preparation method and its application in cigarette.
To achieve the above object, the present invention adopts the following technical scheme that：
A kind of preparation method of cigarette monomer perfume 3- bezene acrylic acids comprising following steps：
It takes 3- cinnamic acids and β-ionol to be dissolved in dry dichloromethane, stirs 10min-30min, 4- bis- is added
Methylamino pyridine (DMAP) and 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate (EDCHCl), are stirred at room temperature
4-12h, TLC monitoring reaction, track reaction end, water washing, liquid separation are added into organic phase, then washed with saturated nacl aqueous solution
It washs, liquid separation, organic phase anhydrous Na2SO4It is dry, it is concentrated to give crude product, then carries out column chromatography for separation, it is single to obtain the cigarette
Body note material 3- bezene acrylic acids, i.e. 3- cinnamic acids-β-ionol esters, structural formula are shown in formula I.
Further, the column chromatography for separation eluent is the mixing of ethyl acetate and petroleum ether, the volume ratio of the two
100:1-20:1。
Further, the molar ratio of the 3- cinnamic acids and β-ionol is 0.9:1-1:Between 0.9.
Further, the 3- cinnamic acids-β-application of the ionol esters as fragrance-enhancing tobacco agent in cigarette, by it
It is applied in cigarette as fragrance-enhancing tobacco agent, additive amount is the 0.01-0.10% of pipe tobacco weight.
The compounds of this invention 3- cinnamic acids-β-ionol esters are a kind of latent aroma compounds, its property is stablized under room temperature,
For colourless liquid, but it generates to have by heating cleavable and obviously increases tobacco aroma substance, such as 3- oxo-betas-violet
Ketone.
Compared to the prior art, beneficial effects of the present invention：
1. the present invention prepares 3- cinnamic acids-β-ionol esters compared with β-ionol parent object, can significantly improve
Additive amount in cigarette, the outer fragrant kind without influencing cigarette.
2. the present invention is with 4-dimethylaminopyridine/1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate
3- cinnamic acids and β-ionol esterification reaction condensation reagent, can significantly improve reaction yield, simplify aftertreatment technology.
3. the 3- cinnamic acids-β that the present invention develops-ionol esters cigarette monomer perfume, for the first time as tobacco
Fumet is applied in cigarette, can reduce the irritation of cigarette and miscellaneous gas, improves the mellow and full sense of cigarette smoke and comfort.
Description of the drawings
Fig. 1 is 3- cinnamic acids-β-ionol esters 1H NMR nuclear magnetic spectrograms；
Fig. 2 is-cinnamic acid-β-ionol esters 13C NMR nuclear magnetic spectrograms；
Fig. 3 is-cinnamic acid-β-ionol esters HRMS high-resolution spectrograms.
Specific implementation mode
With reference to specific embodiment, the present invention is described in further detail, convenient for being well understood in the present invention
Hold, but they do not constitute the present invention and limit.
Embodiment one
The preparation method of tobacco aromaticss monomer 3- cinnamic acids-β-ionol esters：
10mmol β-ionol and 10mmol 3- cinnamic acids is taken to be dissolved in the dichloromethane of 100ml dryings, stirring
After 10min, 4-dimethylaminopyridine (DMAP) (5mmol) and 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimine is added
Hydrochloride (EDCHCl) (11mmol), is stirred at room temperature, TLC monitoring reaction (petroleum ethers：Ethyl acetate=10:1, Rf=0.5, it is purple
Outer 254nm colour developings), track reaction end.Into organic phase plus water 50mL washing, liquid separation, then with 50mL saturated nacl aqueous solutions
Washing, liquid separation, organic phase anhydrous Na2SO4It is dry, it is concentrated to give crude product.Crude product 50mL dichloromethane dissolves, and is added
The silica gel 4g of 100-200 mesh, decompression are spin-dried for mixing sample, and petroleum ether is used in the silica gel column chromatography strain of 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 acids-β-ionol esters：
10mmol β-ionol and 10.5mmol 3- cinnamic acids is taken to be dissolved in the dichloromethane of 100ml dryings, stirring
After 10min, 4-dimethylaminopyridine (DMAP) (4mmol) and 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimine is added
Hydrochloride (EDCHCl) (11mmol), is stirred at room temperature, TLC monitoring reaction (petroleum ethers：Ethyl acetate=10:1, Rf=0.5, it is purple
Outer 254nm colour developings), track reaction end.Into organic phase plus water 50mL washing, liquid separation, then with 50mL saturated nacl aqueous solutions
Washing, liquid separation, organic phase anhydrous Na2SO4It is dry, it is concentrated to give crude product.Crude product 50mL dichloromethane dissolves, and is added
The silica gel 4g of 100-200 mesh, decompression are spin-dried for mixing sample, and petroleum ether is used in the silica gel column chromatography strain of 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 acids-β-ionol esters：
10.5mmol β-ionol and 10mmol 3- cinnamic acids is taken to be dissolved in the dichloromethane of 100ml dryings, stirring
After 10min, 4-dimethylaminopyridine (DMAP) (6mmol) and 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimine is added
Hydrochloride (EDCHCl) (12mmol), is stirred at room temperature, TLC monitoring reaction (petroleum ethers：Ethyl acetate=10:1, Rf=0.5, it is purple
Outer 254nm colour developings), track reaction end.Into organic phase plus water 50mL washing, liquid separation, then with 50mL saturated nacl aqueous solutions
Washing, liquid separation, organic phase anhydrous Na2SO4It is dry, it is concentrated to give crude product.Crude product 50mL dichloromethane dissolves, and is added
The silica gel 4g of 100-200 mesh, decompression are spin-dried for mixing sample, and petroleum ether is used in the silica gel column chromatography strain of 80g 100-200 mesh：Ethyl acetate
=60:1 slowly elutes, concentrate, dry after obtain target product.
(1) structural characterization of target product
As red high resolution mass spectrum (HR-MS), carbon-13 nmr spectra (1H-NMR 13C-NMR) respectively to obtained by embodiment
Target product 3- cinnamic acids-β-ionol esters carry out structural characterization, and specific data are following (as shown in Figs. 1-3)：
3- cinnamic acids-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).
It is analyzed 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 acids-β-ionol esters.
(2) flavoring research of the target product in tobacco
With 95% ethanol as solvent, target product 3- cinnamic acids-β-ionol esters are made into the molten of mass fraction 1%
Liquid.The above-mentioned solution containing target product of 0.5g, 1.0g, 5.0g, 10.0g and 15.0g is taken respectively, and then uniformly spray is added to five parts not
It in the 100g blank cigarette shreds of flavoring and casing, rolls, respectively picks out 100 same weight cigarette, be placed in temperature 22 DEG C ± 1
DEG C, 48h is balanced in the climatic chamber of humidity 60% ± 2%, is smoked panel test.Control sample is blank cigarette, and control sample is equally identical
48h is balanced under the conditions of epidemic disaster.
The flavoring smoking result of 1 3- cinnamic acids-β of table-ionol esters
The above description is merely a specific embodiment, but scope of protection of the present invention is not limited thereto, any
Belong to those skilled in the art in the technical scope disclosed by the present invention, the change or replacement that can be readily occurred in all are answered
It is included within the scope of the present invention.Therefore, protection scope of the present invention should be subject to the protection scope in claims.
Claims (4)
1. a kind of cigarette preparation method of latent fragrant monomer 3- cinnamic acid esters, it is characterised in that include the following steps：
It takes 3- cinnamic acids and β-ionol to be dissolved in dry dichloromethane, stirs 10min-30min, 4- diformazan ammonia is added
4-12h is stirred at room temperature in yl pyridines and 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate, and TLC monitorings are reacted,
Reaction end is tracked, into organic phase plus water washing, liquid separation, then washed with saturated nacl aqueous solution, liquid separation, organic phase is with anhydrous
Na2SO4It is dry, it is concentrated to give crude product, then carries out column chromatography for separation, obtains the cigarette monomer perfume 3- bezene acrylic acids, i.e.,
3- cinnamic acids-β-ionol esters, structural formula are shown in formula I：
2. the cigarette as described in claim 1 preparation method of latent fragrant monomer 3- cinnamic acid esters, it is characterised in that：Described
Column chromatography for separation eluent is the mixing of ethyl acetate and petroleum ether, the volume ratio 100 of the two:1-20:1.
3. the cigarette as described in claim 1 preparation method of latent fragrant monomer 3- cinnamic acid esters, it is characterised in that：Described
The molar ratio of 3- cinnamic acids and β-ionol is 0.9:1-1:Between 0.9.
4. a kind of cigarette prepared such as any the methods of claim 1-3 uses latent fragrant monomer 3- cinnamic acids esters to increase as tobacco
Application of the pastil in cigarette is applied to as fragrance-enhancing tobacco agent in cigarette, and additive amount is the 0.01- of pipe tobacco weight
0.10%.
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| 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 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4461309A (en) * | 1977-06-27 | 1984-07-24 | Givaudan Corporation | Ionyl-alkyl and ionyl alkenyl ethers as flavorants for tobacco |
| US4992106A (en) * | 1988-02-23 | 1991-02-12 | Basf Corporation | Novel oxo-ionol carbonates useful as tobacco flavorants |
| CN1434016A (en) * | 2003-01-24 | 2003-08-06 | 华宝香化科技发展（上海）有限公司 | Method for producing perfume using ionol ester as raw material by thermo-wacking rectifying |
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