CN104082854A - Application of 3-(2-hydroxyphenyl) propionic acid in cigarettes - Google Patents

Application of 3-(2-hydroxyphenyl) propionic acid in cigarettes Download PDF

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Publication number
CN104082854A
CN104082854A CN201410326931.0A CN201410326931A CN104082854A CN 104082854 A CN104082854 A CN 104082854A CN 201410326931 A CN201410326931 A CN 201410326931A CN 104082854 A CN104082854 A CN 104082854A
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CN
China
Prior art keywords
propionic acid
cigarette
hydroxy phenyl
cigarettes
hydroxyphenyl
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Pending
Application number
CN201410326931.0A
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Chinese (zh)
Inventor
朱卓越
黄淑芳
杨华武
李燕春
刘金云
李亚白
邓昌健
傅见山
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China Tobacco Hunan Industrial Co Ltd
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China Tobacco Hunan Industrial Co Ltd
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Publication date
Application filed by China Tobacco Hunan Industrial Co Ltd filed Critical China Tobacco Hunan Industrial Co Ltd
Priority to CN201410326931.0A priority Critical patent/CN104082854A/en
Publication of CN104082854A publication Critical patent/CN104082854A/en
Pending legal-status Critical Current

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Abstract

The invention relates to the application of 3-(2-hydroxyphenyl) propionic acid in cigarettes. The 3-(2-hydroxyphenyl) 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-hydroxyphenyl) propionic acid is 1-100 ppm. By adding the aroma enhancer, the cigarettes with a proper aroma release speed, good aroma release uniformity, good moisture retention and good bake resistance can be obtained, and the smoking quality of the cigarettes is improved.

Description

The application of 3-(2-hydroxy phenyl) propionic acid in cigarette
Technical field
The invention belongs to the flavouring technical field of cigarette, be specifically related to the application of 3-(2-hydroxy phenyl) propionic acid in cigarette.
Background technology
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 dihydroactinidiolide, octahydrocoumarin, dihydrocoumarin etc. all exist 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, and hope can overcome the above problems effectively.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 phenyl) 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 phenyl) 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 phenyl) 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 phenyl) propionic acid in cigarette or cigarette products as fumet.
3-of the present invention (2-hydroxy phenyl) 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 phenyl) 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 phenyl) propionic acid is preferably 5-60ppm.
The addition of 3-(2-hydroxy phenyl) propionic acid is 8-50ppm more preferably.
The addition of 3-(2-hydroxy phenyl) propionic acid is further preferably 10-30ppm.
3-(2-hydroxy phenyl) propionic acid can prepare by the following method:
Dihydrocoumarin 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 phenyl) 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.
3-of the present invention (2-hydroxy phenyl) propionic acid is applied in cigarette after also can mixing with other fumet of the prior art, as long as it does not affect the effect of 3-of the present invention (2-hydroxy phenyl) propionic acid.
3-of the present invention (2-hydroxy phenyl) 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 phenyl) 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 phenyl) 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 phenyl) propionic acid, oh group is more conducive to firmly be adsorbed on the pipe tobacco or thin slice of cigarette, thereby is conducive to deposit.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 phenyl) 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 phenyl) propionic acid, the acquisition of the suction quality that can further ensure.
Accompanying drawing explanation
Fig. 1 is the INFRARED SPECTRUM collection of illustrative plates of 3-(2-hydroxy phenyl) propionic acid for preparing of dihydrocoumarin and embodiment 1;
From Fig. 1, we can find out: the hydrolysate that embodiment 1 prepares is at 3450cm -1there is obvious hydroxyl absworption peak, and at 1709cm -1the carbonyl peak of carboxylic acid compared with raw material dihydrocoumarin at 1749cm -1lactone carbonyl peak have obvious red shift, illustrate and successfully prepared product of the present invention.
Fig. 2 is the HNMR figure of 3-(2-hydroxy phenyl) propionic acid for preparing of embodiment 1.Wherein, δ 12..06 (1H), 9.34 (1H) are carboxylic hydroxyl hydrogen and phenolic hydroxyl group hydrogen, and δ 6.985.. to 7.06 (2H) and δ 6.6789. to 6.783 (2H) are respectively the 4H on phenyl ring; δ 2.723 to 2.753. (2H) and δ 2.451 to 2.511 (2H) are respectively two the methylene hydrogen (4H) on side chain.
Fig. 2 further illustrates embodiment 1 and has successfully prepared product of the present invention.
Specific embodiment
Following examples are intended to further illustrate the present invention, and unrestricted the present invention.
Embodiment 1
0.2mol dihydrocoumarin 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 76mmHg reduced pressure, above-mentioned saponification liquor evaporation is removed to ethanol and a part of water, 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 phenyl) 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 dihydrocoumarin), evaluate.
Embodiment 3
Perfuming experiment 2
Get 3-(2-hydroxy phenyl) 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 dihydrocoumarin), evaluate.
Comparative example 1
Perfuming experiment 3
Get dihydrocoumarin, 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 dihydrocoumarin, 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 phenyl) 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 dihydrocoumarin, 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 phenyl) propionic acid still to keep enough fragrance as the cigarette of fumet.

Claims (4)

  1. The application of 1.3-(2-hydroxy phenyl) propionic acid in cigarette, is characterized in that, 3-(2-hydroxy phenyl) propionic acid is added in cigarette or cigarette products as fumet.
  2. 2. application according to claim 1, is characterized in that, 3-(2-hydroxy phenyl) 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 phenyl) propionic acid is 1-100ppm.
  3. 3. application according to claim 1, is characterized in that, with the weighing scale of pipe tobacco in cigarette or thin slice, the addition of 3-(2-hydroxy phenyl) propionic acid is 5-60ppm.
  4. 4. application according to claim 1, is characterized in that, with the weighing scale of pipe tobacco in cigarette or thin slice, the addition of 3-(2-hydroxy phenyl) propionic acid is 10-30ppm.
CN201410326931.0A 2014-07-10 2014-07-10 Application of 3-(2-hydroxyphenyl) propionic acid in cigarettes Pending CN104082854A (en)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113277947A (en) * 2021-06-04 2021-08-20 安徽中烟工业有限责任公司 Monomer spice 3- (2-hydroxyphenyl) propionic acid-2 hydroxypropyl ester for cigarette and synthetic method and application thereof

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US4036237A (en) * 1976-02-20 1977-07-19 Philip Morris Incorporated Smoking composition
US4178458A (en) * 1976-02-20 1979-12-11 Philip Morris, Inc. Smoking composition
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
CN102002440A (en) * 2010-11-19 2011-04-06 成都宏亿实业集团有限公司 Essence for tonka bean odor type cigarettes
CN102154060A (en) * 2011-03-02 2011-08-17 广州市澳键香料有限公司 Formula of tobacco additive essence of hami melon fragrance
CN102304423A (en) * 2011-03-17 2012-01-04 广州市澳键丰泽生物科技有限公司 Fragrance-enhancing tobacco essence
CN102948921A (en) * 2012-11-12 2013-03-06 武汉黄鹤楼香精香料有限公司 Flavoring base material for tobacco
CN103584276A (en) * 2013-11-13 2014-02-19 川渝中烟工业有限责任公司 Ambergris cigarette and ambergris spices
CN103695173A (en) * 2012-09-27 2014-04-02 邢娜 Mango flavor tobacco essence

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4036237A (en) * 1976-02-20 1977-07-19 Philip Morris Incorporated Smoking composition
US4141906A (en) * 1976-02-20 1979-02-27 Philip Morris Incorporated Smoking composition and compounds therefor
US4178458A (en) * 1976-02-20 1979-12-11 Philip Morris, Inc. Smoking composition
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
CN102002440A (en) * 2010-11-19 2011-04-06 成都宏亿实业集团有限公司 Essence for tonka bean odor type cigarettes
CN102154060A (en) * 2011-03-02 2011-08-17 广州市澳键香料有限公司 Formula of tobacco additive essence of hami melon fragrance
CN102304423A (en) * 2011-03-17 2012-01-04 广州市澳键丰泽生物科技有限公司 Fragrance-enhancing tobacco essence
CN103695173A (en) * 2012-09-27 2014-04-02 邢娜 Mango flavor tobacco essence
CN102948921A (en) * 2012-11-12 2013-03-06 武汉黄鹤楼香精香料有限公司 Flavoring base material for tobacco
CN103584276A (en) * 2013-11-13 2014-02-19 川渝中烟工业有限责任公司 Ambergris cigarette and ambergris spices

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113277947A (en) * 2021-06-04 2021-08-20 安徽中烟工业有限责任公司 Monomer spice 3- (2-hydroxyphenyl) propionic acid-2 hydroxypropyl ester for cigarette and synthetic method and application thereof
CN113277947B (en) * 2021-06-04 2023-10-03 安徽中烟工业有限责任公司 3- (2-hydroxyphenyl) propionic acid-2-hydroxypropyl ester as cigarette monomer spice and synthesis method and application thereof

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Application publication date: 20141008