CN106496168A - Preparation method and applications of the cigarette with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester - Google Patents
Preparation method and applications of the cigarette with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester Download PDFInfo
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- CN106496168A CN106496168A CN201610880325.2A CN201610880325A CN106496168A CN 106496168 A CN106496168 A CN 106496168A CN 201610880325 A CN201610880325 A CN 201610880325A CN 106496168 A CN106496168 A CN 106496168A
- Authority
- CN
- China
- Prior art keywords
- cigarette
- alcohol ester
- furancarboxylic acid
- herba pelargonii
- pelargonii graveolentiss
- 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.)
- Pending
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- 235000019504 cigarettes Nutrition 0.000 title claims abstract description 39
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 title claims abstract description 36
- -1 alcohol ester Chemical class 0.000 title claims abstract description 34
- 239000002304 perfume Substances 0.000 title claims abstract description 19
- 239000000178 monomer Substances 0.000 title claims abstract description 18
- 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 21
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims abstract description 16
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims abstract description 13
- 239000007788 liquid Substances 0.000 claims abstract description 12
- 241000208125 Nicotiana Species 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- 208000035126 Facies Diseases 0.000 claims abstract description 10
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims abstract description 8
- 239000005792 Geraniol Substances 0.000 claims abstract description 8
- 229940113087 geraniol Drugs 0.000 claims abstract description 8
- 239000012043 crude product Substances 0.000 claims abstract description 7
- 150000003839 salts Chemical class 0.000 claims abstract description 6
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims abstract description 5
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims abstract description 5
- 239000007864 aqueous solution Substances 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 5
- 238000012544 monitoring process Methods 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 238000004440 column chromatography Methods 0.000 claims abstract description 4
- 238000000926 separation method Methods 0.000 claims abstract description 4
- 239000012467 final product Substances 0.000 claims abstract description 3
- 238000005406 washing Methods 0.000 claims abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
- 239000003208 petroleum Substances 0.000 claims description 5
- 239000007832 Na2SO4 Substances 0.000 claims description 2
- 244000061176 Nicotiana tabacum Species 0.000 claims description 2
- 239000003480 eluent Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000000047 product Substances 0.000 abstract description 8
- 239000000779 smoke Substances 0.000 abstract description 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
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 12
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-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
- 239000000463 material Substances 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 206010013786 Dry skin Diseases 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 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
- 230000006837 decompression Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 239000000243 solution Substances 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
- CNOPDZWOYFOHGN-BQYQJAHWSA-N Beta-Ionol Chemical compound CC(O)\C=C\C1=C(C)CCCC1(C)C CNOPDZWOYFOHGN-BQYQJAHWSA-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
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- CNOPDZWOYFOHGN-UHFFFAOYSA-N beta-ionol Natural products CC(O)C=CC1=C(C)CCCC1(C)C CNOPDZWOYFOHGN-UHFFFAOYSA-N 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
- 230000032050 esterification 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
- 238000010438 heat treatment Methods 0.000 description 1
- 238000006460 hydrolysis reaction Methods 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
- 229930003658 monoterpene Natural products 0.000 description 1
- 235000002577 monoterpenes Nutrition 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
- 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
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
- A24B15/406—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms in a five-membered 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)
- Manufacture Of Tobacco Products (AREA)
- Fats And Perfumes (AREA)
Abstract
The present invention provides a kind of cigarette preparation method of monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester, comprises the steps：Take furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester and geraniol is dissolved in dry dichloromethane, stirring 10min 30min, add 4 dimethylamino naphthyridines (DMAP) and 1 ethyl (3 dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate (EDCHCl), 4 12h are stirred at room temperature, TLC monitoring reactions, tracking reaction end, add water in organic faciess washing, divide liquid, washed with saturated nacl aqueous solution again, point liquid, organic faciess are dried with anhydrous Na 2SO4, crude product is concentrated to give, column chromatography for separation is then carried out and is obtained final product the cigarette monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester.Product prepared by the present invention can significantly improve the addition in Medicated cigarette, and not affect the outer fragrant kind of Medicated cigarette, be applied in Medicated cigarette as fragrance-enhancing tobacco agent, it is possible to decrease the zest of Medicated cigarette and miscellaneous QI, improve 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 monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester
Preparation method and applications.
Background technology
Many excellent spice are as its high high-temp stability is poor, volatility compared with strong, fragrance remaining time is short the problems such as limit
Which is widely applied.Latent Studies of The Aromatic Substances is that a class relative molecular mass is big, the material that 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 safety preferably, listed in natural perfume material category in the world, allocated some local flavor edible essence effects with which
Very well.Different from volatility and half volatile fragrance matter, perfume class compound of diving is reducing artificial flavor and taste compensation vestige
It is not result in the significant changes of the material delivering amount such as nicotine in cigarette mainstream flue gas, tar simultaneously, more longlasting can stably provides cigarette
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 furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester is planted, and inquires into its application in perfuming cigarette.
Content of the invention
The present invention is in order to develop new cigarette flavor precursors, there is provided a kind of new cigarette is with latent perfume monomer furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester
Preparation method and its application in Medicated cigarette.
For achieving the above object, the present invention is adopted the following technical scheme that：
Preparation method of the cigarette with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester shown in a kind of formula (I), which comprises the steps：
Take furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester and geraniol is dissolved in dry dichloromethane, stir 10min-30min, add 4- diformazans
Aminopyridine (DMAP) and 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate (EDCHCl), are stirred at room temperature 4-
12h, TLC monitoring reaction (petroleum ether：Ethyl acetate=10:1, Rf=0.5, ultraviolet 254nm colour developings), reaction end is tracked, to
Add water in organic faciess washing, point liquid, then is washed with saturated nacl aqueous solution, point liquid, organic faciess anhydrous Na2SO4Dry, concentration
Crude product is obtained, column chromatography for separation is then carried out and is obtained final product the cigarette monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester.
Further, described column chromatography for separation eluent is ethyl acetate and petroleum ether, both volume ratios 100:1-
20:1.
Further, the molar ratio of described furancarboxylic acid and geraniol is 0.9:1-1:Between 0.9.
Further, the cigarette that prepared by method as defined above is with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester as fragrance-enhancing tobacco agent in volume
Application in cigarette, is applied in Medicated cigarette as fragrance-enhancing tobacco agent, 0.01-0.05% of the addition for tobacco shred weight.
The compounds of this invention furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester is a kind of latent aroma compounds, and under room temperature, which is stable in properties, is colourless liquid,
But which passes through heating cleavable generation tool and is significantly increased tobacco aroma material.Such as geraniol, monoterpene vinyl compound, furancarboxylic acid.
Compared to the prior art, beneficial effects of the present invention：
1. the present invention prepares furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester compared with β-ionol parent thing, can significantly improve adding in Medicated cigarette
Dosage, and do not affect the outer fragrant kind of Medicated cigarette.
2. the present invention with DMAP/1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate is
Furancarboxylic acid and Herba Pelargonii Graveolentiss alcohol ester esterification condensation reagent, can significantly improve reaction yield, simplify aftertreatment technology.
3. the furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester cigarette monomer perfume that the present invention is developed, is applied to as fragrance-enhancing tobacco agent first
In Medicated cigarette, it is possible to decrease the zest of Medicated cigarette and miscellaneous QI, the mellow and full sense of cigarette smoke and comfortableness is improved.
Description of the drawings
Fig. 1 is furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester 1H NMR nuclear magnetic spectrograms；
Fig. 2 is furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester 13C NMR nuclear magnetic spectrograms；
Fig. 3 is furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester HRMS high-resolution spectrograms.
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 aromatics using monomer furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester：
Take 10mmol geraniol and 10mmol furancarboxylic acids are dissolved in the dichloromethane of 100ml dryings, after stirring 10min, add
DMAP (DMAP) is (5mmol) and 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate
(EDCHCl) (11mmol), it is stirred at room temperature, TLC monitoring reactions track reaction end.The 50mL that adds water in organic faciess is washed, point
Liquid, then washed with 50mL saturated nacl aqueous solutions, point liquid, organic faciess are dried with anhydrous Na 2SO4, are concentrated to give crude product.Crude product
Dissolved with 50mL dichloromethane, add the silica gel 4g of 100-200 mesh, decompression is spin-dried for mixing sample, with the layer of silica gel of 80g 100-200 mesh
Petroleum ether is used in analysis strain：Ethyl acetate=60:1 slowly eluting, concentration, dry after obtain target product.
Embodiment two
The preparation method of tobacco aromatics using monomer furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester：
Take 10mmol geraniol and 10.5mmol furancarboxylic acids are dissolved in the dichloromethane of 100ml dryings, after stirring 10min, plus
Enter DMAP (DMAP) (4mmol) and 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate
(EDCHCl) (11mmol), it is stirred at room temperature, TLC monitoring reactions track reaction end.The 50mL that adds water in organic faciess is washed, point
Liquid, then washed with 50mL saturated nacl aqueous solutions, point liquid, organic faciess are dried with anhydrous Na 2SO4, are concentrated to give crude product.Crude product
Dissolved with 50mL dichloromethane, add the silica gel 4g of 100-200 mesh, decompression is spin-dried for mixing sample, with the layer of silica gel of 80g 100-200 mesh
Petroleum ether is used in analysis strain：Ethyl acetate=60:1 slowly eluting, concentration, 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 furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester carries out structural characterization, and concrete data are as follows：
As Figure 1-3, furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester：Colourless oil liquid.1H NMR(400MHz,CDCl3)δppm 7.57
(s, 1H), 7.18 (d, J=2.81Hz, 1H), 6.53-6.47 (m, 1H), 5.45 (q, J=7.31,7.31,7.21Hz, 1H),
5.14-5.04 (m, 1H), 4.81 (dd, J=14.06,7.23Hz, 2H), 2.19-2.02 (m, 4H), 1.77 (d, J=
12.72Hz,3H),1.67(s,3H),1.60(s,3H)；13C NMR(400MHz,CDCl3)δppm 158.81,146.16,
144.88,142.90,131.88,123.71,118.83,117.79,111.80,61.84,39.58,32.24,25.69,
23.58,16.58；HRMS:m/z(ESI)[M+Na]+Theoretical value 271.1310, measured value 271.1311.
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 furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester.
(2) perfuming research of the target product in Nicotiana tabacum L.
With 95% ethanol as solvent, the solution that target product furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester is made into mass fraction 1%.Take respectively
The above-mentioned solution containing target product of 0.5g, 1.0g, 5.0g, 10.0g and 15.0g, then uniform spray are added to five parts of non-flavoring and casings
100g blank cigarette shreds in, roll, respectively pick out 100 same weight Medicated cigarette, be placed in 22 DEG C ± 1 DEG C of temperature, humidity
48h is balanced in 60% ± 2% climatic chamber, is smoked panel test.Control sample is blank Medicated cigarette, and control sample is equally in identical epidemic disaster
Under the conditions of balance 48h.
The perfuming smoking result of 1 furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester of table
Claims (4)
1. preparation method of the cigarette with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester shown in a kind of formula (I), it is characterised in that comprise the steps：
Take furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester and geraniol is dissolved in dry dichloromethane, stir 10min-30min, add 4- dimethylaminos
Pyridine (DMAP) and 1- ethyls-(3- dimethylaminopropyls) phosphinylidyne diimmonium salt hydrochlorate (EDCHCl), are stirred at room temperature 4-12h,
TLC monitoring reactions, track reaction end, and add water in organic faciess washing, point liquid, then is washed with saturated nacl aqueous solution, point liquid,
Organic faciess anhydrous Na2SO4Dry, be concentrated to give crude product, then carry out column chromatography for separation and obtain final product the cigarette monomer perfume furancarboxylic acid
Herba Pelargonii Graveolentiss alcohol ester.
2. preparation method of the cigarette as claimed in claim 1 with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester, it is characterised in that：Described post
Chromatography eluent is ethyl acetate and petroleum ether, both volume ratios 100:1-20:1.
3. preparation method of the cigarette as claimed in claim 1 with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester, it is characterised in that：Described bran
Acid and the molar ratio of geraniol are 0.9:1-1:Between 0.9.
4. a kind of cigarette such as the preparation of any one of claim 1-3 methods described is increased as Nicotiana tabacum L. with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester
Application of the pastil in Medicated cigarette, is applied in Medicated cigarette as fragrance-enhancing tobacco agent, 0.01- of the addition for tobacco shred weight
0.05%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610880325.2A CN106496168A (en) | 2016-10-09 | 2016-10-09 | Preparation method and applications of the cigarette with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610880325.2A CN106496168A (en) | 2016-10-09 | 2016-10-09 | Preparation method and applications of the cigarette with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN106496168A true CN106496168A (en) | 2017-03-15 |
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| CN201610880325.2A Pending CN106496168A (en) | 2016-10-09 | 2016-10-09 | Preparation method and applications of the cigarette with monomer perfume furancarboxylic acid Herba Pelargonii Graveolentiss alcohol ester |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299359A (en) * | 2018-03-20 | 2018-07-20 | 东南大学 | A kind of furans esters of gallic acid tobacco aromaticss and preparation method thereof and the application in cigarette |
| CN111685360A (en) * | 2019-03-12 | 2020-09-22 | 湖南中烟工业有限责任公司 | Hydroxy acid alcohol ester cigarette latent aroma, preparation thereof and application thereof in cigarettes |
| CN115141133A (en) * | 2022-06-24 | 2022-10-04 | 河南中烟工业有限责任公司 | Latent aroma substance for cigarettes as well as preparation method and application thereof |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002090481A1 (en) * | 2001-05-04 | 2002-11-14 | The Procter & Gamble Company | Compositions and articles for effective deposition of perfume |
| WO2003066618A1 (en) * | 2002-02-07 | 2003-08-14 | Galileo Pharmaceuticals, Inc. | Cytoprotective benzofuran derivatives |
-
2016
- 2016-10-09 CN CN201610880325.2A patent/CN106496168A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002090481A1 (en) * | 2001-05-04 | 2002-11-14 | The Procter & Gamble Company | Compositions and articles for effective deposition of perfume |
| WO2003066618A1 (en) * | 2002-02-07 | 2003-08-14 | Galileo Pharmaceuticals, Inc. | Cytoprotective benzofuran derivatives |
Non-Patent Citations (2)
| Title |
|---|
| 张峻松 等: "糠酸酯的合成及香气研究", 《香料香精化妆品》 * |
| 秦耀果 等: "不同杂环取代(E)-β-Farnesene 类似物的合成及生物活性研究", 《有机化学》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299359A (en) * | 2018-03-20 | 2018-07-20 | 东南大学 | A kind of furans esters of gallic acid tobacco aromaticss and preparation method thereof and the application in cigarette |
| CN111685360A (en) * | 2019-03-12 | 2020-09-22 | 湖南中烟工业有限责任公司 | Hydroxy acid alcohol ester cigarette latent aroma, preparation thereof and application thereof in cigarettes |
| CN115141133A (en) * | 2022-06-24 | 2022-10-04 | 河南中烟工业有限责任公司 | Latent aroma substance for cigarettes as well as preparation method and application thereof |
| CN115141133B (en) * | 2022-06-24 | 2023-06-16 | 河南中烟工业有限责任公司 | Tobacco aroma-suppressing substance and preparation method and application thereof |
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