CN106496112B - Preparation method and application of latent aroma monomer pyridine-3,5-dicarboxylate for cigarette - Google Patents
Preparation method and application of latent aroma monomer pyridine-3,5-dicarboxylate for cigarette Download PDFInfo
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- CN106496112B CN106496112B CN201610880174.0A CN201610880174A CN106496112B CN 106496112 B CN106496112 B CN 106496112B CN 201610880174 A CN201610880174 A CN 201610880174A CN 106496112 B CN106496112 B CN 106496112B
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- pyridine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/803—Processes of preparation
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
- C07D213/80—Acids; Esters in position 3
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Pyridine Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
A kind of latent fragrant monomer pyridine -3 of cigarette, the preparation method of 5- diformic ester, include the following steps: to take pyridine -3,5- dioctyl phthalate and single hydroxyl alcohol are dissolved in dry methylene chloride, stir 10min-30min, 4-dimethylaminopyridine and 1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate is added, 4-12h is stirred at room temperature, TLC monitoring reaction, tracks reaction end, water washing is added into organic phase, liquid separation, it is washed again with saturated sodium chloride solution, liquid separation, organic phase anhydrous Na2SO4It is dry, it is concentrated to give crude product, column chromatography for separation is up to product.The present invention prepares pyridine -3, two spiceleaf alcohol ester of 5- dioctyl phthalate and pyridine -3, two-β of 5- dioctyl phthalate-ionol esters are compared with geraniol and β-ionol maternal body, it is remarkably improved the additive amount in cigarette, it is applied in cigarette, the irritation and miscellaneous gas, the mellow and full sense of raising cigarette smoke and comfort of cigarette can be reduced.
Description
Technical field
The present invention relates to flavors and fragrances and tobacco manufacture field, latent fragrant monomer pyridine -3, the 5- diformazan of specifically a kind of cigarette
The preparation method and applications of esters of gallic acid.
Background technique
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 release by the approach such as chemical hydrolysis, enzymatic hydrolysis or microbial action, pyrolysis, photodestruciton with fragrance fragrance
Compound.Because its safety is preferable, it is included in natural perfume material scope in the world, deploys certain flavor edible essence effects 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 not will 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 latent fragrant monomer pyridine -3, the 5- diformic ester of kind cigarette, and inquire into its application in perfuming cigarette.
Summary of the invention
The present invention provides a kind of new cigarette latent fragrant monomer pyridine -3,5- bis- to develop novel cigarette flavor precursors
The preparation method of formate ester and its application in cigarette.
To achieve the above object, the present invention adopts the following technical scheme:
A kind of preparation method of cigarette monomer perfume pyridine -3,5- dicarboxylic acid esters comprising following steps: it includes as follows
Step:
It takes pyridine -3,5- dioctyl phthalate and single hydroxyl alcohol to be dissolved in dry methylene chloride, stirs 10min-30min, be added
4-dimethylaminopyridine (DMAP) and 1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate (EDCHCl), room temperature
4-12h is stirred, TLC monitoring reaction tracks reaction end, water washing, liquid separation added into organic phase, then use saturated sodium chloride solution
Washing, liquid separation, organic phase anhydrous Na2SO4It is dry, it is concentrated to give crude product, column chromatography for separation is up to the latent fragrant monomer pyrrole of the cigarette
Pyridine -3,5- diformic ester.
Further, the column chromatography for separation eluent is ethyl acetate and petroleum ether, the volume ratio 100:1- of the two
20:1。
Further, the molar ratio of pyridine -3,5- dioctyl phthalate and single hydroxyl alcohol is between 0.9:1-1:0.9.
Further, the single hydroxyl alcohol is that geraniol or ionol are obtained when single hydroxyl alcohol is geraniol
Product is two spiceleaf alcohol ester of pyridine -3,5- dioctyl phthalate, and when single hydroxyl alcohol is ionol, obtained product is pyridine -3,5-
Two-β of dioctyl phthalate-ionol esters, the two structural formula are as follows:
3,5- cinchomeronic acid, two spiceleaf alcohol ester
3,5- cinchomeronic acid, two-β-ionol esters.
A kind of cigarette of method as described above preparation use latent perfume monomer benzenpropanoic acid esters as fragrance-enhancing tobacco agent in cigarette
Using as fragrance-enhancing tobacco agent applied in cigarette, additive amount is the 0.005-0.05% of pipe tobacco weight.
Two spiceleaf alcohol ester of the compounds of this invention pyridine -3,5- dioctyl phthalate and two-β of pyridine -3,5- dioctyl phthalate-ionol esters
For a kind of latent aroma compounds, its property is stablized under room temperature, is colourless liquid, but it is generated by heating cleavable has obvious increase
Add tobacco aroma substance, such as 3- oxo-beta-ionone, geraniol, pyridines, monoterpene vinyl compound.
Compared to the prior art, beneficial effects of the present invention:
1. the present invention prepares two spiceleaf alcohol ester of pyridine -3,5- dioctyl phthalate and pyridine -3,5- dioctyl phthalate two-β-ionol esters
Compared with geraniol and β-ionol maternal body, the additive amount in cigarette can be significantly improved, the outer perfume (or spice) without influencing cigarette
Kind.
2. the present invention is with 4-dimethylaminopyridine/1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate
Pyridine -3,5- dioctyl phthalate and geraniol, β-ionol esterification reaction condensation reagent, can significantly improve reaction yield, simplify
Aftertreatment technology.
3. two kinds of cigarette monomer perfumes that the present invention develops are applied in cigarette as fragrance-enhancing tobacco agent for the first time,
The irritation and miscellaneous gas, the mellow and full sense of raising cigarette smoke and comfort of cigarette can be reduced.
Detailed description of the invention
Fig. 1 is two spiceleaf alcohol ester 1H NMR nuclear magnetic spectrogram of pyridine -3,5- dioctyl phthalate；
Fig. 2 is two spiceleaf alcohol ester 13C NMR nuclear magnetic spectrogram of pyridine -3,5- dioctyl phthalate；
Fig. 3 is two spiceleaf alcohol ester HRMS high-resolution spectrogram of pyridine -3,5- dioctyl phthalate；
Fig. 4 is two-β of pyridine -3,5- dioctyl phthalate-ionol esters 1H NMR nuclear magnetic spectrogram；
Fig. 5 is two-β of pyridine -3,5- dioctyl phthalate-ionol esters 13C NMR nuclear magnetic spectrogram；
Fig. 6 is two-β of pyridine -3,5- dioctyl phthalate-ionol esters HRMS high-resolution spectrogram.
Specific embodiment
The present invention is described in further detail combined with specific embodiments below, convenient for being well understood in of the invention
Hold, but they limiting the invention.
Embodiment one
The preparation method of two spiceleaf alcohol ester of tobacco aromaticss monomer pyridine -3,5- dioctyl phthalate:
10mmol geraniol and 5mmol pyridine -3,5- dioctyl phthalate is taken to be dissolved in the dry methylene chloride of 100ml, stirring
After 10min, 4-dimethylaminopyridine (DMAP) (5mmol) and 1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimine is added
Hydrochloride (EDCHCl) (11mmol), is stirred at room temperature, and TLC monitoring reaction (petroleum ether: ethyl acetate=10:1, Rf=0.5 is purple
Outer 254nm colour developing), track reaction end.Into organic phase plus water 50mL washing, liquid separation, then with 50mL saturated sodium chloride solution
Washing, liquid separation, organic phase anhydrous Na2SO4It is dry, it is concentrated to give crude product.Crude product 50mL methylene chloride dissolves, and is added
The silica gel 4g of 100-200 mesh, decompression be spin-dried for mixing sample, in the silica gel column chromatography strain of 80g 100-200 mesh use petroleum ether: ethyl acetate
=60:1 is slowly eluted, be concentrated, dry after obtain target product.
Embodiment two
The preparation method of two spiceleaf alcohol ester of tobacco aromaticss monomer pyridine -3,5- dioctyl phthalate:
10mmol geraniol and 5.2mmol pyridine -3,5- dioctyl phthalate is taken to be dissolved in the dry methylene chloride of 100ml, stirring
After 10min, 4-dimethylaminopyridine (DMAP) (4mmol) and 1- ethyl-(3- dimethylaminopropyl) phosphinylidyne diimine is added
Hydrochloride (EDCHCl) (11mmol), is stirred at room temperature, and TLC monitoring reaction (petroleum ether: ethyl acetate=10:1, Rf=0.5 is purple
Outer 254nm colour developing), track reaction end.Into organic phase plus water 50mL washing, liquid separation, then with 50mL saturated sodium chloride solution
Washing, liquid separation, organic phase anhydrous Na2SO4It is dry, it is concentrated to give crude product.Crude product 50mL methylene chloride dissolves, and is added
The silica gel 4g of 100-200 mesh, decompression be spin-dried for mixing sample, in the silica gel column chromatography strain of 80g 100-200 mesh use petroleum ether: ethyl acetate
=60:1 is slowly eluted, be concentrated, dry after obtain target product.
Embodiment three
Two-β of tobacco aromaticss monomer pyridine -3,5- dioctyl phthalate-ionol esters preparation method:
In three-necked flask, weighed 20mmol β-ionol is added and 10mmol pyridine -3,5- dioctyl phthalate is dissolved in
In 200ml dry methylene chloride, after stirring 10min, 4-dimethylaminopyridine (DMAP) (10mmol) and 1- ethyl-is added
(3- dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate (EDCHCl) (22mmol), is stirred at room temperature, TLC monitoring reaction
(petroleum ether: ethyl acetate=10:1, Rf=0.5, ultraviolet 254nm colour developing), tracking reaction is to terminal.It is into organic phase plus pure
Water 100mL washing, liquid separation, then washed with 100mL saturated sodium chloride solution, liquid separation, organic phase anhydrous Na2SO4It is dry, concentration
Crude product.Crude product 10mL methylene chloride dissolves, and the silica gel 7g of 100-200 mesh is added, and decompression is spin-dried for mixing sample, uses 100g
The silica gel column chromatography post separation of 100-200 mesh, eluant, eluent petroleum ether: ethyl acetate=80:1 is slowly eluted, after being concentrated, drying
To target product
Example IV
Two-β of tobacco aromaticss monomer pyridine -3,5- dioctyl phthalate-ionol esters preparation method:
In three-necked flask, weighed 20mmol β-ionol is added and 10.5mmol pyridine -3,5- dioctyl phthalate is dissolved in
In 200ml dry methylene chloride, after stirring 10min, 4-dimethylaminopyridine (DMAP) (8mmol) and 1- ethyl-(3- is added
Dimethylaminopropyl) phosphinylidyne diimmonium salt hydrochlorate (EDCHCl) (22mmol), is stirred, TLC monitoring reaction (petroleum at room temperature
Ether: ethyl acetate=10:1, Rf=0.5, ultraviolet 254nm colour developing), tracking reaction is to terminal.Add pure water into organic phase
100mL washing, liquid separation, then washed with 100mL saturated sodium chloride solution, liquid separation, organic phase is dry with anhydrous Na 2SO4, concentration
Crude product.Crude product 10mL methylene chloride dissolves, and the silica gel 7g of 100-200 mesh is added, and decompression is spin-dried for mixing sample, uses 100g
The silica gel column chromatography post separation of 100-200 mesh, eluant, eluent petroleum ether: ethyl acetate=80:1 is slowly eluted, after being concentrated, drying
To 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
Two spiceleaf alcohol ester of target product pyridine -3,5- dioctyl phthalate and two-β of pyridine -3,5- dioctyl phthalate-ionol esters carry out structure table
Sign, specific data are as follows:
Two spiceleaf alcohol ester (as shown in Figs. 1-3) of pyridine -3,5- dioctyl phthalate: colourless oil liquid.1H NMR(400MHz,
CDCl3) δ ppm 9.36 (s, 2H), 8.87 (s, 1H), 5.48 (q, J=6.85,6.85,6.82Hz, 2H), 5.10 (dd, J=
14.20,7.50Hz, 2H), 4.89 (dd, J=13.30,7.25Hz, 2H), 2.22-2.07 (m, 8H), 1.62 (d, J=
12.00Hz, 6H), 1.67 (s, 6H), 1.79 (t, J=8.25,8.25Hz, 6H)；13C NMR(400MHz,CDCl3)δppm
164.54,154.15,143.38,138.01,131.95,126.31,123.63,117.70,62.64,39.55,26.26,
25.69,17.72,16.62；HRMS:m/z(ESI)[M+H]+Theoretical value 440.2801, measured value 440.2791.
Two-β of pyridine-3,5- dioctyl phthalate-ionol esters (as Figure 4-Figure 6): colourless oil liquid.1H NMR
(400MHz,CDCl3) δ ppm 9.36 (d, J=2.05Hz, 2H), 8.85 (t, J=1.89,1.89Hz, 1H), 6.25 (d, J=
15.87Hz, 2H), 5.69 (p, J=6.51,6.51,6.48,6.48Hz, 2H), 5.59-5.48 (m, 2H), 1.97 (t, J=
6.07,6.07Hz, 4H), 1.66 (s, 6H), 1.60 (dd, J=7.84,4.17Hz, 4H), 1.53 (s, 3H), 1.52 (s, 3H),
1.45 (dd, J=5.93,2.47Hz, 4H), 0.99 (s, 1H), 0.97 (s, 12H)；13C NMR(400MHz,CDCl3)δ
ppm163.80,154.00,137.91,136.37,132.08,131.18,129.49,126.66,73.60,39.31,33.88,
32.65,28.65,21.31,20.66,19.19.[M+Na]+found 542.3245(calcd.542.3246).
It is analyzed from spectrum elucidation, in conjunction with infrared spectroscopy (IR), high resolution mass spec (1HR-MS) and carbon-13 nmr spectra
(13C-NMR) can determine that gained compound is two-β of two spiceleaf alcohol ester of pyridine -3,5- dioctyl phthalate and pyridine -3,5- dioctyl phthalate -
Ionol esters.
(2) flavoring research of the target product in tobacco
With 95% ethanol as solvent, by two spiceleaf alcohol ester of target product pyridine -3,5- dioctyl phthalate and pyridine -3,5- dioctyl phthalate
Two-β-ionol esters are made into the solution of mass fraction 1% respectively.It takes on 0.5g, 1.0g, 5.0g, 10.0g and 15.0g respectively
The solution containing target product is stated, then uniformly spray is added in the 100g blank cigarette shreds of five parts of non-flavoring and casings, is rolled, is respectively chosen
100 same weight cigarette are selected, 22 DEG C ± 1 DEG C of temperature is placed in, balances 48h in the climatic chamber of humidity 60% ± 2%, comment
It inhales.Control sample is blank cigarette, and control sample equally balances 48h under the conditions of identical epidemic disaster.
The flavoring smoking result of 1 pyridine -3,5- dioctyl phthalate of table, two spiceleaf alcohol ester
2 pyridine -3,5- dioctyl phthalate of table, two-β-ionol esters flavoring smoking result
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, any changes or substitutions that can be easily thought of, all answers
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 pyridine -3,5- diformic ester, it is characterised in that include the following steps: to take
Pyridine -3,5- dioctyl phthalate and single hydroxyl alcohol are dissolved in dry methylene chloride, stir 10min-30min, and 4- dimethylamino is added
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, water washing, liquid separation is added into organic phase, then washed with saturated sodium chloride solution, liquid separation,
Organic phase anhydrous Na2SO4It is dry, it is concentrated to give crude product, column chromatography for separation is up to the latent fragrant monomer pyridine -3,5- bis- of the cigarette
Formate ester；The single hydroxyl alcohol is geraniol or ionol, and when single hydroxyl alcohol is geraniol, obtained product is pyrrole
Two spiceleaf alcohol ester of pyridine -3,5- dioctyl phthalate, when single hydroxyl alcohol is ionol, obtained product is pyridine -3,5- dioctyl phthalate two -
β-ionol esters, the two structural formula are as follows:
2. the cigarette as described in claim 1 preparation method of latent fragrant monomer pyridine -3,5- diformic ester, it is characterised in that:
The column chromatography for separation eluent is ethyl acetate and petroleum ether, the volume ratio 100:1-20:1 of the two.
3. the cigarette as described in claim 1 preparation method of latent fragrant monomer pyridine -3,5- diformic ester, it is characterised in that:
The molar ratio of the pyridine -3,5- dioctyl phthalate and single hydroxyl alcohol is between 0.9:1-1:0.9.
4. a kind of cigarette such as any one of claim 1-3 the method preparation is used latent fragrant monomer benzenpropanoic acid esters as tobacco and is increased
Application of the pastil in cigarette is applied in cigarette as fragrance-enhancing tobacco agent, and additive amount is the 0.005- of pipe tobacco weight
0.05%.
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| US5172706A (en) * | 1992-01-21 | 1992-12-22 | Philip Morris Incorporated | Smoking compositions containing an oxalate flavorant-release additive |
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| CN102286033A (en) * | 2011-09-05 | 2011-12-21 | 川渝中烟工业公司 | Monosaccharide beta-ionol carbonate diester compound as well as preparation method and application thereof |
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-
2016
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5172706A (en) * | 1992-01-21 | 1992-12-22 | Philip Morris Incorporated | Smoking compositions containing an oxalate flavorant-release additive |
| CN101686719A (en) * | 2007-07-25 | 2010-03-31 | 菲利普莫里斯生产公司 | Perfume ester salts of polycarboxylic acids and method for releasing hydroxyl-containing perfumes |
| CN101486645A (en) * | 2008-01-18 | 2009-07-22 | 河南中烟工业公司 | Flavouring essences for tobacco and preparation thereof |
| CN102286033A (en) * | 2011-09-05 | 2011-12-21 | 川渝中烟工业公司 | Monosaccharide beta-ionol carbonate diester compound as well as preparation method and application thereof |
| CN102304155A (en) * | 2011-09-05 | 2012-01-04 | 川渝中烟工业公司 | Monosaccharide geraniol carbonate diester compound, preparation method and use thereof |
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