CN104082845A - Application of 3-(2-hydroxycyclohexane) propionic acid in cigarettes - Google Patents
Application of 3-(2-hydroxycyclohexane) propionic acid in cigarettes Download PDFInfo
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- CN104082845A CN104082845A CN201410327674.2A CN201410327674A CN104082845A CN 104082845 A CN104082845 A CN 104082845A CN 201410327674 A CN201410327674 A CN 201410327674A CN 104082845 A CN104082845 A CN 104082845A
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- propionic acid
- cigarette
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- cyclohexyl
- cigarettes
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Abstract
The invention relates to the application of 3-(2-hydroxycyclohexane) propionic acid in cigarettes. The 3-(2-hydroxycyclohexane) propionic acid is applied to the cigarettes as an aroma enhancer, and by the weight of tobacco shreds or slices in the cigarettes, the addition amount of the 3-(2-hydroxycyclohexane) propionic acid is 1-100 ppm. By adding the aroma enhancer, the cigarettes with a proper aroma release speed, aroma release uniformity, moisture retention and bake resistance can be obtained, and the smoking quality of the cigarettes is improved.
Description
Technical field
The invention belongs to the flavouring technical field of cigarette, be specifically related to the application of 3-(2-hydroxy-cyclohexyl) propionic acid in cigarette.
Technical background
And addible fumet comprises the ester classes such as dihydroactinidiolide, octahydrocoumarin, dihydrocoumarin in existing cigarette, it has unique odor characteristic, be applied in the prior art in cigarette, as tobacco aromatics using, particularly in flue-cured tobacco, to be widely used.But due to octahydrocoumarin, dihydrocoumarin fragrance unreasonableness, and the problem such as that dihydroactinidiolide, octahydrocoumarin, dihydrocoumarin etc. all exist is volatile, fragrance rate of release is fast, make to aspirate inhomogeneous, and there is the problem of suction dried, be unfavorable for that it is used in tobacco the effective use as fumet always.Those skilled in the art is in the urgent need to searching out a kind of fumet, thereby effectively overcomes the above problems.In addition, 3-that those skilled in the art is appreciated that (2-hydroxy phenyl) propionic acid is important pharmaceutical intermediate and fine chemical product.
Summary of the invention
For the problems referred to above, the thinking that inventor is used to have according to those skilled in the art, other self is had to the ester class that is suitable for fragrance in cigarette and be applied in cigarette, but find still to exist above-mentioned fragrance to discharge fast, to discharge inhomogeneous, not ovenable roasting, suction dried problem.Inventor also just I had never expected at all and will use 3-(2-hydroxy-cyclohexyl) propionic acid at the beginning of research, because those skilled in the art can not go to expect or consider to add 3-(2-hydroxy-cyclohexyl) propionic acid this itself not have dulcet or its smell should be the composition not being suitable in cigarette, at Field of Tobacco, do not apply this class material yet.But when the present inventor finds 3-(2-hydroxy-cyclohexyl) propionic acid to be applied in cigarette by once accidental trial, can overcome well the problems referred to above.
Therefore, the object of the present invention is to provide a kind of application of compound, it has not volatile, and during suction, fragrance discharges the effect that can improve suction quality slow, that fragrance discharges uniformly, relative prior art has humectation and ovenable roasting effect.
Technical scheme of the present invention
The present invention is added into 3-(2-hydroxy-cyclohexyl) propionic acid in cigarette or cigarette products as fumet.
3-of the present invention (2-hydroxy-cyclohexyl) propionic acid is added in the pipe tobacco or reconstituted tobacoo of cigarette.With the weighing scale of pipe tobacco in cigarette or thin slice, the addition of this 3-(2-hydroxy-cyclohexyl) propionic acid is 1-100ppm.
With the weighing scale of pipe tobacco in cigarette or thin slice, the addition of 3-in cigarette (2-hydroxy-cyclohexyl) propionic acid is preferably 5-60ppm.
The addition of 3-(2-hydroxy-cyclohexyl) propionic acid is 8-50ppm more preferably.
The addition of 3-(2-hydroxy-cyclohexyl) propionic acid is further preferably 10-30ppm.
The preparation of 3-(2-hydroxy-cyclohexyl) propionic acid can be: octahydrocoumarin is mixed with absolute ethyl alcohol, then add NaOH solution, saponification at 60-100 ℃, is cooled to room temperature after reacting completely.Under reduced pressure, remove the second alcohol and water in saponification liquor, then at normal temperatures, carry out acidification reaction, after product is separated out, reactant liquor is placed in to 0 ℃ of refrigeration and spends the night and make its ageing, decompress filter, obtains 3-of the present invention (2-hydroxy-cyclohexyl) propionic acid.
Described saponification temperature is preferably 70-80 ℃.
After saponification, except in the process of second alcohol and water, can add saturated aqueous common salt or water absorbing agent to process.
The acid solution of described use is preferably hydrochloric acid solution.
Reaction equation is as follows:
3-of the present invention (2-hydroxy-cyclohexyl) propionic acid is applied in cigarette after also can mixing with other fumet of the prior art, as long as it does not affect its effect of the present invention.
3-of the present invention (2-hydroxy-cyclohexyl) propionic acid in making an addition to pipe tobacco in cigarette and thin slice, can also make an addition in stem etc., in addition, can also be applied to separately as fumet, use in other tobacco product.
Beneficial effect of the present invention
The present invention by using self not the aromatic 3-of tool (2-hydroxy-cyclohexyl) propionic acid as fumet, add in cigarette, not only obtained good flavouring effect, experiment shows that it also has good humectation effect, mellow and full property and the comfortableness of fragrance have been improved, and fragrance discharges evenly in aspiration procedure, fine solved in prior art, use fragrance that dihydroactinidiolide, octahydrocoumarin, dihydrocoumarin or other fumet exist discharge fast, discharge inhomogeneous, suction dried and the not ovenable problem such as roasting.3-of the present invention (2-hydroxy-cyclohexyl) propionic acid is low compared to the volatility of the compositions such as dihydroactinidiolide, octahydrocoumarin, dihydrocoumarin, deposits in process and can not discharge fast because volatile problem causes fragrance; And in described 3-(2-hydroxy-cyclohexyl) propionic acid, oh group is more conducive to be firmly adsorbed on favourable depositing on the pipe tobacco of cigarette or thin slice.Meanwhile, also pleasantly surprised discovery of inventor, can in aspiration procedure, can slowly discharge fragrance, and the fragrance of its release is even by application of the present invention, humectation and ovenable roasting.The present invention is by unexpected a trial, obtained 3-(2-hydroxy-cyclohexyl) propionic acid that is suitable as very much fumet in cigarette, solved well the problem that prior art exists, by adding this fumet, can obtain that fragrance rate of release is moderate, fragrance discharges evenly, humectation and ovenable roasting cigarette, has promoted the suction quality of cigarette.In addition, the present invention is by preferably controlling the addition of 3-(2-hydroxy-cyclohexyl) propionic acid, the acquisition of the suction quality that can further ensure.
Accompanying drawing explanation
Fig. 1 is the infrared spectrum of 3-(2-hydroxy-cyclohexyl) propionic acid for preparing of octahydrocoumarin and embodiment 1;
From Fig. 1, we can find out: the hydrolysate that embodiment 1 prepares is at 3418cm
-1there is obvious hydroxyl absworption peak, and at 1715cm
-1the carbonyl peak of carboxylic acid compared with raw material octahydrocoumarin at 1740cm
-1lactone carbonyl peak have obvious red shift, meet theoretical requirement.Illustrate and successfully prepared 3-(2-hydroxy-cyclohexyl) propionic acid.
Fig. 2 is the HNMR figure of 3-(2-hydroxy-cyclohexyl) propionic acid for preparing of embodiment 1.Wherein, 1H NMR (DMSO, 500MHz), (ppm): 11.92 (s, 1H, COOH), 4.81 (s, 1H, CHOH), 3.39 (s, 1H, CHOH).
Fig. 2 further illustrates embodiment 1 and has successfully prepared 3-(2-hydroxy-cyclohexyl) propionic acid.
Specific embodiment
Following examples are intended to further illustrate the present invention, and unrestricted the present invention.
Embodiment 1
Below only for of 3-(2-hydroxy-cyclohexyl) propionic acid prepares example, concrete, the product that both can use following method to prepare in practice, 3-(2-hydroxy-cyclohexyl) propionic acid that also can use the preparation method of prior art to obtain.
0.2mol octahydrocoumarin is added in there-necked flask, and continue to add 0.3mol absolute ethyl alcohol, in oil bath pan, heat stirring and dissolving, then the NaOH solution that adds 0.6mol10mol/L, reaction at 80 ℃, through chromatogram, detect, after feedstock conversion is complete, stop heating and being cooled to room temperature, obtain saponification liquor.
Under the condition of 76mmHg decompression, above-mentioned saponification liquor is removed to ethanol and a part of water by evaporation, and add wherein saturated common salt solution or the water absorbing agent sodium sulphate of 30mL, the saponification liquor after being concentrated;
Measure 300mL2.0mol/L HCl solution, and add wherein 70.0g NaCl solid particle, rapid stirring that it is dissolved, added at normal temperatures in the saponification liquor after concentrated and carry out acidifying, separate out product, be placed in 0 ℃ of refrigeration and spend the night and make its ageing.Finally, by decompress filter, obtain product.
By expert group, aspirate, following perfuming experimental result is evaluated.
Embodiment 2
Perfuming experiment 1
Get 3-(2-hydroxy-cyclohexyl) propionic acid that embodiment 1 prepares, with the Daqu spirit of China of 52 ℃, being diluted to concentration is 2.0g/L solution.Get above-mentioned solution 5mL, adopt spray pattern perfuming, above-mentioned solution is evenly sprayed on 1000g pipe tobacco, balance 48h under the condition of 22 ℃ and relative humidity 60%, baking, takes out and makes cigarette, smoke panel test, with control sample contrast (adding octahydrocoumarin), evaluate.
Embodiment 3
Perfuming experiment 2
Get 3-(2-hydroxy-cyclohexyl) propionic acid that embodiment 1 prepares, with the Daqu spirit of China of 52 ℃, being diluted to concentration is 2.0g/L solution.Get above-mentioned solution 5mL, adopt spray pattern perfuming, above-mentioned solution is evenly sprayed on 1000g thin slice, balance 48h under the condition of 22 ℃ and relative humidity 60%, baking, takes out and makes cigarette, smoke panel test, with control sample contrast (adding octahydrocoumarin), evaluate.
Comparative example 1
Perfuming experiment 3
Get octahydrocoumarin, with the Daqu spirit of China of 52 ℃, being diluted to concentration is 2.0g/L solution.Get above-mentioned solution 5mL, adopt spray pattern perfuming, above-mentioned solution is evenly sprayed on 1000g pipe tobacco, balance 48h under the condition of 22 ℃ and relative humidity 60%, baking, takes out and makes cigarette, smokes panel test.
Comparative example 2
Perfuming experiment 4
Get octahydrocoumarin, with the Daqu spirit of China of 52 ℃, being diluted to concentration is 2.0g/L solution.Get above-mentioned solution 5mL, adopt spray pattern perfuming, above-mentioned solution is evenly sprayed on 1000g thin slice, balance 48h under the condition of 22 ℃ and relative humidity 60%, baking, takes out and makes cigarette, smokes panel test.
The evaluation and analysis result of embodiment 2,3 and comparative example 1,2 is as shown in table 1 below.
Table 1
From the evaluation and analysis result of table 1, can find out, with respect to comparative example 1 and comparative example 2, embodiment 2 and embodiment 3 not only fragrance discharge evenly, and fragrance rate of release is moderate, and has good humectation and ovenable roasting property.
And evaluate and analyse result and show, no matter be that 3-of the present invention (2-hydroxy-cyclohexyl) propionic acid is sprayed on pipe tobacco or is sprayed on thin slice, its cigarette of making all can obtain uniform fragrance, good humectation and ovenable roasting property.
Embodiment 4
Perfuming experiment 5
The cigarette that embodiment 2 is prepared was placed after one week, then evaluated and analysed.
Embodiment 5
Perfuming experiment 6
The cigarette that embodiment 3 is prepared was placed after one week, then evaluated and analysed.
Comparative example 3
Perfuming experiment 7
The cigarette that comparative example 1 is prepared was placed after one week, then evaluated and analysed.
Comparative example 4
Perfuming experiment 8
The cigarette that comparative example 2 is prepared was placed after one week, then evaluated and analysed.
The evaluation and analysis comparing result of embodiment 4,5 and comparative example 3,4 is as shown in table 2 below.
Table 2
From the evaluation and analysis result of table 2, can find out, with respect to comparative example 3 and comparative example 4, the cigarette of embodiment 4 and embodiment 5 not only fragrance discharges evenly, and fragrance rate of release is moderate, has good humectation and ovenable roasting property; And after placing one week, due to the high volatility of octahydrocoumarin, its content in cigarette reduces in a large number, causes the fragrance of cigarette too light, but adds 3-of the present invention (2-hydroxy-cyclohexyl) propionic acid still to keep enough fragrance as the cigarette of fumet.
Claims (4)
- The application of 1.3-(2-hydroxy-cyclohexyl) propionic acid in cigarette, is characterized in that, 3-(2-hydroxy-cyclohexyl) propionic acid is added in cigarette or cigarette products as fumet.
- 2. application according to claim 1, is characterized in that, 3-(2-hydroxy-cyclohexyl) propionic acid is added in the pipe tobacco or reconstituted tobacoo of cigarette; With the weighing scale of pipe tobacco in cigarette or thin slice, the addition of 3-(2-hydroxy-cyclohexyl) propionic acid is 1-100ppm.
- 3. application according to claim 1, is characterized in that, the addition of 3-(2-hydroxy-cyclohexyl) propionic acid is 5-60ppm.
- 4. application according to claim 1, is characterized in that, the addition of 3-(2-hydroxy-cyclohexyl) propionic acid is 10-30ppm.
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| CN201410327674.2A CN104082845A (en) | 2014-07-10 | 2014-07-10 | Application of 3-(2-hydroxycyclohexane) propionic acid in cigarettes |
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| CN201410327674.2A CN104082845A (en) | 2014-07-10 | 2014-07-10 | Application of 3-(2-hydroxycyclohexane) propionic acid in cigarettes |
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Citations (5)
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| JPH0670736A (en) * | 1991-11-04 | 1994-03-15 | Quest Internatl Bv | Diterpenoid alcohol for perfuming purpose |
| CN101250100A (en) * | 2008-01-31 | 2008-08-27 | 上海英华香精香料有限公司 | Preparation of novel flavoring agents capable of remarkably intensifying tobacco fragrance and smoking smell |
| CN101557725A (en) * | 2006-12-13 | 2009-10-14 | 奇华顿荷兰服务有限责任公司 | Flavour modulating derivative of a carboxylic acid and a purine, pyrimidine, nucleoside or nucleotide |
| CN102161935A (en) * | 2010-12-31 | 2011-08-24 | 广东中烟工业有限责任公司 | Endogenous perfume from tobacco as well as preparation method and application thereof |
| CN102423114A (en) * | 2011-07-25 | 2012-04-25 | 红塔烟草(集团)有限责任公司 | Low-tar cigarette aroma compensation method |
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2014
- 2014-07-10 CN CN201410327674.2A patent/CN104082845A/en active Pending
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0670736A (en) * | 1991-11-04 | 1994-03-15 | Quest Internatl Bv | Diterpenoid alcohol for perfuming purpose |
| CN101557725A (en) * | 2006-12-13 | 2009-10-14 | 奇华顿荷兰服务有限责任公司 | Flavour modulating derivative of a carboxylic acid and a purine, pyrimidine, nucleoside or nucleotide |
| CN101250100A (en) * | 2008-01-31 | 2008-08-27 | 上海英华香精香料有限公司 | Preparation of novel flavoring agents capable of remarkably intensifying tobacco fragrance and smoking smell |
| CN102161935A (en) * | 2010-12-31 | 2011-08-24 | 广东中烟工业有限责任公司 | Endogenous perfume from tobacco as well as preparation method and application thereof |
| CN102423114A (en) * | 2011-07-25 | 2012-04-25 | 红塔烟草(集团)有限责任公司 | Low-tar cigarette aroma compensation method |
Non-Patent Citations (5)
| Title |
|---|
| 张岩磊: "《卷烟降焦工程》", 31 October 2000, 中国轻工业出版社 * |
| 曾晓鹰等: "《卷烟调香体系构建-以云烟品牌为例》", 28 February 2013, 西南交通大学出版社 * |
| 罗志臣等: "香豆素-3-羧酸的合成工艺研究", 《化工科技》 * |
| 谢剑平: "《烟草香料技术原理与应用》", 31 March 2009, 化学工业出版社 * |
| 韩云辉: "《烟用材料生产技术与应用》", 31 March 2012, 中国质检出版社 * |
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