RU2580682C1 - Flavoured composition for reducing adsorbed tobacco smell and cigarette - Google Patents

Abstract

FIELD: tobacco industry.

SUBSTANCE: invention relates to flavoring composition for reduction of adsorbed tobacco odour. Composition contains ionone, selected from a group, made up of alpha-ionone, beta-ionone and methyl-ionone, and another flavouring component, which is a gamma-peach lactone. Content of γ-peach lactone varies from 70 to 80 wt%, and content of ionone - from 20 to 30 wt%.

EFFECT: invention relates to a cigarette, containing the specified flavouring composition.

4 cl, 5 tbl

Description

FIELD OF THE INVENTION

The present invention relates to a flavoring composition for reducing an adsorbed tobacco odor and to a cigarette containing it.

State of the art

A variety of deodorizing technologies have been developed with respect to due to increased public alertness regarding unpleasant odors and foreign odors. In addition, a variety of deodorants have been developed, the purpose of which is to eliminate the “adsorbed odor” resulting from the adsorption of odorous substances on clothing, textiles, hair, etc. Deodorants include deodorants aimed at the “adsorbed tobacco smell” that is formed as a result of adsorption of odorous tobacco substances released along with the sidestream smoke during smoking, on clothing, textiles, hair, and the like. (see Japanese Unexamined Patent Publication (KOKAI) No. 2007-77545, Japanese National Patent Publication No. PCT No. 9-505500 and Japanese Unexamined Patent Publication (KOKAI) No. 2006-340785). However, it was not intended to add the deodorizing component to the cigarette, and if the deodorizing component is added to the cigarette in its pure form, the problem arises that the deodorizing component decomposes during the burning of the cigarette. In addition, if the deodorizing component is added to the cigarette in its pure form, it is necessary to add a large amount of the deodorizing component, and thus, as a result of the smoking process, a significant deterioration in the characteristic tobacco aroma and taste occurs. Accordingly, it is necessary that the flavoring substance to reduce the adsorbed tobacco odor exhibit the effect of reducing the adsorbed tobacco odor when added to a cigarette in a very small amount.

On the other hand, deodorants have also been developed that reduce the smell of sidestream smoke (see Japanese Pending Patent Publication (KOKAI) No. 2002-143285, Japanese Unexamined Patent Publication (KOKAI) No. 2002-143284, Japanese Unexamined Patent Publication (KOKAI) No. 2002 -146386 and Japanese Unexamined Patent Publication (KOKAI) No. 2009-179711). In addition, flavoring compositions have also been developed that are added to cigarettes to eliminate odor from the sidestream smoke (see Japanese Unexamined Patent Publication (KOKAI) No. 2009-179708 and Japanese Unexamined Patent Publication (KOKAI) No. 11-124800). The flavoring composition can effectively eliminate the odor of the sidestream smoke without causing a significant increase in the intensity of the cigarette’s overall smell (i.e., without deteriorating the characteristic tobacco aroma and taste during smoking), even if the flavor of the flavoring composition is mixed with the tobacco odor. However, not all flavoring compositions are deodorants that are intended to reduce the odor of the sidestream smoke, and they are not intended to reduce the adsorbed tobacco smell, as in the present invention. An adsorbed tobacco odor is, as described above, an odor that occurs after the tobacco odor is adsorbed on clothing, textiles, hair, and the like. In order to develop an aroma to reduce adsorbed tobacco odor, it is necessary to consider the desorption processes and the functional manifestation of the aroma after the aroma is adsorbed on clothing or hair. Thus, it is considered difficult to create a flavoring composition to eliminate the odor of the sidestream smoke, which at the same time reduces the smell of the sidestream, and also has the effect of reducing the adsorbed tobacco odor. In addition, in order to obtain a sufficient effect of reducing adsorbed tobacco odor, it is necessary to increase the amount of deodorant per unit surface area of clothing or hair. In other words, in order to mask the tobacco smell that is adsorbed on clothing or hair, it is necessary to add a flavoring agent in a significantly increased amount compared to the case of eliminating the smell of sidestream smoke. On the other hand, adding a large amount of a flavoring composition can suppress the aroma and taste during smoking, and thus it is required that the flavoring composition exhibit a strong effect of reducing the adsorbed tobacco smell even when using a very small amount of such flavoring composition to reduce adsorbed tobacco odor. If it is contemplated to add such a flavoring composition to cigarettes, research into the addition method is also necessary. The application of a flavoring composition to cigarette paper is proposed as one of the typical addition methods. As a result of applying the flavoring composition to the cigarette paper, the flavoring composition is adsorbed on clothing or hair through a sidestream smoke, and thereafter, the flavoring composition is desorbed, exhibiting its corresponding function. However, almost all of the existing flavoring compositions that exhibit an odor-reducing effect are highly volatile at ordinary temperatures, and thus cannot be held in sufficient quantities in cigarette paper for an extended period of time. In addition, it is known that the flavoring substance added to the cigarette paper is transferred over time to the crushed tobacco or wrapping material and as a result affects the aroma and taste during smoking.

In order to solve the problems described above, there is provided a flavoring agent that is modified in such a way that it is stable and non-volatile during the manufacturing process of the tobacco product as well as under storage conditions, and that the flavoring substance is released from the tobacco product as a result of thermal decomposition or desorption in the conditions of smoking. For example, Japanese national patent publication PCT No. 2-501075 and US patent No. 4804002 describe a flavoring composition, which consists of a glycoside, which is a carbohydrate acetal, and a flavoring substance. However, the problem with this technology is that glycoside thermal decomposition products contaminate smoke during smoking and impair the aroma and taste of smoking. In addition, this technology cannot be applied to a flavoring substance that is not capable of forming glycosides, and thus, the flavoring agents used are limited. Japanese Unexamined Patent Publication (KOKAI) No. 5-146285, US Patent No. 5144964, Japanese National Patent Publication PCT No. 7-504080, and US Patent No. 5479949 describe techniques by which a flavoring substance is incorporated into cyclodextrin. However, these technologies also have the problem that the thermal decomposition products of cyclodextrin pollute the smoke during smoking and worsen the aroma and taste of smoking. In addition, there are restrictions on the amount of flavoring substance that may be included in cyclodextrin. There are also restrictions on the amount of cyclodextrin that can be applied to cigarette paper, taking into account the suitability of the cigarette-making device. Thus, there is also the problem with these technologies that only a small amount of flavoring agent can be used compared to the case in which the flavoring agent is applied directly to cigarette paper. Flavors that can be used in these technologies are limited to flavors, which even in small amounts are capable of exhibiting the effect of reducing adsorbed tobacco odor, and thus, the type of flavorant is limited in these technologies.

SUMMARY OF THE INVENTION

As noted above, until now, methods for reducing the tobacco odor adsorbed on clothing or hair by using a deodorant added to a cigarette, as well as examples related to this problem itself, have remained almost unknown, and no deodorants have been shown to be effective. while reducing the adsorbed tobacco smell and providing a characteristic tobacco aroma and taste during smoking.

The present invention, accordingly, is to provide a flavoring composition that is able to reduce the adsorbed tobacco odor by using it in a relatively small amount, and which does not impair the characteristic tobacco aroma and taste during smoking, as well as a cigarette that uses this composition.

The present inventors have found that when an ionone selected from the group consisting of α-ionone, β-ionone and methylionone is used in combination with another flavoring component, ionon can increase the intensity of the flavor of another flavoring component. They also found that the flavoring composition sufficiently reduces the adsorbed tobacco odor that remains as a result of adsorption on clothing or hair when it is present in an amount that does not affect the suitability of the cigarette-making device and does not impair the characteristic tobacco aroma and taste in the process. smoking. In addition, the authors found that when γ-decalactone is used as another flavoring component, the enhancement of the effect is especially pronounced.

According to one aspect of the present invention, there is provided a flavoring composition for reducing an adsorbed tobacco odor comprising an ionone selected from the group consisting of α-ionon, β-ionon and methylionone, and another flavoring component.

In the flavoring composition according to the present invention, the ionon content is preferably from 10 to 50 wt.% And more preferably from 20 to 30 wt.%.

In the flavoring composition according to the present invention, the other flavoring component is not limited in a particular way, and it may include, for example, terpene aldehydes, such as hydroxycytronellal; terpene ketones such as piperitone; terpene alcohols such as citronellol, geraniol, linalool, rhodinol and α-terpineol; terpene esters such as terpinyl acetate; linear aliphatic alcohols such as dihydromyrceneol; linear aliphatic aldehydes such as trans-2-decenal; cyclic aliphatic ketones such as methyl dihydrojasmonate, ethyl maltol and cis-jasmonate; aliphatic esters such as anisyl acetate, benzyl butyrate, ethyl laurate and allyl cyclohexane propionate; aliphatic lactones such as γ-undecalactone, γ-decalactone, γ-nonalactone, γ-octalactone, sclareolide, ω-pentadecalactone (15-pentadecanolide), δ-dodecalactone and γ-heptalactone; aliphatic carboxylic acids such as myristic acid; aromatic aldehydes such as anisic aldehyde, ethyl vanillin, 4-isopropylbenzaldehyde, 4-ethylbenzaldehyde, cinnamaldehyde, 4-ethoxybenzaldehyde and lilial; aromatic ketones such as methylanisoleacetone, p-hydroxybenzylacetone (raspberry ketone) and methyl-β-naphthyl ketone; aromatic alcohols such as propenylguaetole; aromatic esters such as anisyl formate, phenylethyl butyrate, cinnamyl acetate, benzyl propionate, 4-methoxybenzyl phenyl acetate, cinnamyl propionate, methylanthranylate, phenylethyl isobutyrate, methyl salicylate, methyl cinnamate and ethyl cinnamate; aromatic ethers such as 4-propylanisole and anethole; aromatic lactones such as 3-propylidenephthalide; and aromatic carboxylic acids, such as 3-phenylpropionic acid. These components can be used individually or as part of an appropriate mixture (flavoring composition), if necessary. Among these components, one or more compounds selected from the group consisting of hydrocytronellal, citronellol, geraniol, linalool, rhodinol, dihydromyrceneol, trans-2-decenal, methyldihydrojasmonate, anisyl acetate, benzyl butyrate, allylcyclohexane propionactone, γ-deca γ-octalactone, ω-pentadecalactone (15-pentadecanolide), anisic aldehyde, ethyl vanillin, lilial, p-hydroxybenzyl acetone (raspberry ketone), propenyl gua teol, anisyl formate, phenylethyl butyrate, cinnamyl acetate, cinnamyl propio atom, methyl cinnamate and ethyl cinnamate. In particular, one or more compounds selected from the group consisting of citronellol, geraniol, rhodinol, anisyl acetate, γ-decalactone, γ-nonalactone, propenylguaethol and anisyl formate are more preferred.

Instead of the aforementioned flavoring components or together with the aforementioned flavoring components, a natural flavoring agent containing the aforementioned component can be used. Such natural flavors include, for example, citronella oil, rose oil, geranium oil, rose geranium oil, eucalyptus oil, geranium leaf oil, Chinese cinnamon oil, palmmarose oil, lemongrass oil, thyme oil, tea tree oil (Osmanthus fragrans var. Aurantiacus oil ), basil oil, bergamot oil, pink bergamot oil, rosewood oil, cananga oil, carrot seed oil, champagne oil, clary sage oil, coriander seed oil, ho tree leaf oil, jasmine m bed, lavender oil, lavender oil, lavender stem oil, white lavender oil, marjoram oil, absolute narcissus oil, neroli oil, orange oil, orange blossom oil, petigrene oil, kircasone snake oil, ylang-ylang oil, cananga oil, wormwood oil , coriander oil, coriander seed oil, wormwood oil, carrot leaf oil, champaka oil, cistus oil, pomegranate leaf oil, carambola oil, aniseed oil, fennel oil, calendula oil, coriander oil, recycle oil, etc.

When the other flavoring component in the flavoring composition according to the present invention is only γ-decalactone, it is preferable that the γ-decalactone content is from 70 to 80 wt.% And the ionone content is from 20 to 30 wt.%.

According to another aspect of the present invention, there is provided a cigarette that contains the aforementioned flavoring composition to reduce adsorbed tobacco odor. The flavoring composition for reducing the adsorbed tobacco odor according to the present invention can be added to a cigarette at any conventional stage of adding flavoring composition to cigarettes. As tobacco material, any type of tobacco material can be used, such as leaf tobacco (fire-dried tobacco, Burley tobacco, oriental tobacco, etc.), as well as homogenized tobacco. Typically, tobacco material is used to make cigarettes in a state of crushed tobacco. Ground tobacco may be blasted tobacco. The flavoring composition for reducing adsorbed tobacco odor according to the present invention can be added to any part of the tobacco material or non-tobacco material (such as a tobacco filter).

In addition, the inventors of the present invention have found that when an aromatic composition containing ionone is incorporated into cyclodextrin, the undesirable aroma and taste that the cyclodextrin thermal decomposition products cause during smoking can be attenuated. Accordingly, a cigarette according to the present invention is preferably a cigarette in which crushed tobacco wraps cigarette paper, and a flavoring composition included in cyclodextrin is applied or sprayed onto the cigarette paper.

In the cigarette of the present invention, the applied amount of the flavoring composition included in the cyclodextrin is preferably 100 ppm or more and 200 ppm or less.

As described above, the aroma enhancing effect of another flavoring component can be obtained by using a flavoring composition comprising an ionone.

Therefore, even if the flavoring agent provides only an insufficient masking effect in such a small amount that it can be included in cyclodextrin, the combined use of the flavoring agent and ionone enhances the flavor to such an extent that a sufficient masking effect is achieved.

As a result, the variety of usable flavoring agents expands to a greater extent than in traditional cases, and it becomes possible to expand the variety of flavor characteristics.

Description of Embodiments

The following are embodiments of the present invention.

Study 1

We studied the effect of ionon on the weakening of undesirable aroma and taste during smoking caused by the products of thermal decomposition of cyclodextrin.

Cigarette making

Example 1A: 75 parts by weight cyclodextrin (CD) was mixed with 25 parts by weight β-ionone (BI) included in cyclodextrin (BI included in CD) in powder state. The mixed powder was dispersed in an aqueous solution containing 6.0 wt.% Carboxymethyl cellulose, obtaining a final concentration of 16 wt.%, And as a result, a dispersion was prepared. A grooved roller coater manufactured by Yasui Seiki Co., Ltd. was used, and the dispersion was coated with a grooved roller into a center portion of a width of 7 mm of cigarette paper (P35) having a width of 27 mm. As a result of the analysis, using a gas chromatograph / mass selective detector (GC-MSD), it was determined that β-ionone had a cyclodextrin incorporation coefficient of 9.2%, and the amount of β-ionone deposited on the cigarette was 23.2 parts per million. Using the manufactured cigarette paper, a cigarette sample was made in Example 1A. As a cigarette, a conventional commercially available cigarette was used.

As a control for the cigarette sample in Example 1A, cigarette samples in comparative examples 1A, 1B and 1C were made. The following cigarette papers were used for cigarette samples in comparative examples 1A, 1B and 1C. Cigarette papers used in cigarette samples in comparative examples 1B and 1C were made by coating with a grooved roller using a dispersion in the same manner as described above. Using each of the manufactured cigarette papers, cigarette samples were made in comparative examples 1A, 1B and 1C. As a cigarette, the same commercially available cigarette was used as in Example 1A.

Comparative Example 1A: No Coating

Comparative example 1B: coating containing cyclodextrin (CD)

Comparative Example 1C: Coating Containing (CD) + γ-Decalactone (DL) Included in Cyclodextrin (DL Included in CD)

Evaluation of aroma and taste during smoking

Evaluation of aroma and taste during smoking of manufactured cigarette samples using the rating scale was carried out by three of the company's own expert appraiser. Evaluation points are determined as follows:

1 point = very unsatisfactory aroma and taste during smoking;

2 points = unsatisfactory aroma and taste during smoking;

3 points = not quite satisfactory aroma and taste during smoking;

4 points = not quite good aroma and taste during smoking;

5 points = good aroma and taste during smoking; and

6 points = very good aroma and taste during smoking.

The number of points in the evaluation of each sample was the arithmetic average of the estimated points of three expert evaluators. Evaluation points were calculated to the first decimal place. The results are presented in table 1.

Table 1 The ratio of components of the flavoring composition (wt.%) The applied amount of BI The applied amount of DL The number of points in the evaluation of aroma and taste during smoking CD BI included in CD DL included on CD mcg per cigarette ppm per cigarette mcg per cigarette ppm per cigarette Average value Comparative Example 1A 0 0 0 0 0 0 0 5.7 Comparative Example 1B one hundred 0 0 0 0 0 0 2.0 Example 1A 75 25 0 15.1 23,2 0 0 4.3 Comparative Example 1C 75 0 25 0 0 15.1 23,2 2,3

The following information was determined from Table 1. The cigarette in Comparative Example 1B using pure CD coated cigarette paper had a weaker aroma and taste during smoking compared to the cigarette in Comparative Example 1A using uncoated cigarette paper. The cigarette in Example 1A using cigarette paper coated with CD and BI included in the CD showed the enhanced effect of improving aroma and taste during smoking compared to the cigarette in Comparative Example 1B, and the number of rating points in Example 1A is close to the rating of cigarettes in comparative example 1A. The cigarette in comparative example 1C using cigarette paper coated with CD and DL included in the CD did not show the effect of improving aroma and taste during smoking compared to the cigarette in comparative example 1B.

In addition, in the case where α-ionone or methylionone was used instead of β-ionone, the effect of improving aroma and taste during smoking was observed, as for the cigarette in Example 1A.

Study 2

We studied the effect of ionon on enhancing the aroma of another flavoring component. Another flavoring component used in this study is γ-decalactone.

Production of flavoring solution

As a flavoring solution, a solution was prepared containing only γ-decalactone (pure DL); a solution containing γ-decalactone and ionon (I + DL) in a mixture; and a solution containing only ionon (pure I). As the ionone, α-ionone, β-ionone or methylionone were used. The content of γ-decalactone and ionone in each solution is presented in table 2. Propylene glycol (PG) was used as a solvent. A solution containing only γ-decalactone and a solution containing a mixture of γ-decalactone and ionone was prepared by adding 20 μl of flavoring agent and 1000 μl of PG to a screw-forming vessel, and a solution of flavoring substance in PG was obtained. The aroma content in a solution containing only ionon was recalculated for the ionon content in a solution containing a mixture of γ-decalactone and ionon in PG.

Organoleptic assessment

Three of the company's own appraisal experts placed each of the perfumes prepared on the edge of the odor test paper, and scent intensity was evaluated using a six-point rating scale. In the case of a solution containing only γ-decalactone and a solution containing a mixture of γ-decalactone and ionone, the aroma intensity of γ-decalactone in the solution was evaluated. In the case of a solution containing only ionon, the intensity of the ionon aroma was evaluated. Evaluation points are determined as follows:

1 point = very low aroma intensity;

2 points = low aroma intensity;

3 points = not very low flavor intensity;

4 points = not very high flavor intensity;

5 points = high aroma intensity; and

6 points = very high flavor intensity.

The number of rating points of each sample was the arithmetic average of the rating points of three expert evaluators. Evaluation points were calculated to the first decimal place. The results are presented in table 2.

table 2

Ionon concentration 0% 0.1% 1,0% 10.0% 20.0% 30.0% 50.0% DL only I + DL Only i I + DL Only i I + DL Only i I + DL Only i I + DL Only i I + DL Only i Ionon content - 0.02 0.02 0.20 0.20 2.00 2.00 4.00 4.00 6.00 6.00 10.00 10.00 Γ-decalactone content 20.00 19.98 - 19.80 - 18.00 - 16.00 - 14.00 - 10.00 - The number of estimated points of aroma intensity when using α-ionon 3.2 3.3 1.3 3,5 1.3 4.3 2.0 4,5 1.8 4.8 2.1 4.0 2,3 The number of estimated points of aroma intensity when using β-ionone 3,7 1,0 3,7 1,0 5.2 1.7 5.3 1,5 5.7 2.0 4.6 2,4 The number of estimated points of aroma intensity when using methylion 3.3 1,0 3.6 1,0 4,5 2.2 4.6 2.1 4.8 2.2 4.3 2,3

The following information was determined from Table 2. In each of the solutions containing a mixture of γ-decalactone and ionon, the aroma intensity of γ-decalactone is increased compared to the intensity (3.2) of the aroma of a solution containing only γ decalactone. It was found that although the content of γ-decalactone decreases with increasing ion content, the intensity of the aroma of γ-decalactone significantly increases. According to estimates, the greater the difference between the number of estimated intensity points of aroma of γ-decalactone for a sample solution and the number of estimated intensity points of aroma of γ-decalactone for a solution containing only γ-decalactone (without adding an ion), the greater the enhancement effect. Thus, the ionon content in a solution containing a mixture of γ-decalactone and ionon is preferably from 10 to 50 wt.%, More preferably from 20 to 30 wt.%. This trend can be observed in all cases in which any ionon is used, including α-ionon, β-ionon, and methylionone.

On the other hand, the number of estimated intensity points of the aroma of the solution in which only the ionon was contained was 2.4 or less in each case, i.e. the aroma intensity was relatively low. This shows that the intensity of the aroma can generally increase without changing the overall characteristics of the aroma, in other words, while maintaining the aroma characteristics of γ-decalactone.

Study 3

The effect of reducing adsorbed tobacco odor was investigated.

Cigarette making

Aromatic compositions were prepared having component ratios that are presented in table 3 and table 4 (based on 100% of the total weight). The same cigarette used as Example 1A was used as a cigarette.

1. Examples 3A-3H and comparative examples 3A-3D

Each flavoring composition was dissolved in ethanol, and then a solution was applied to the entire surface of the cigarette paper using a syringe. The applied amount of ethanol solution of each flavoring composition was 10 μl per cigarette. The amount added (parts per million) in Table 3 is the amount of flavoring composition added per cigarette (containing powdered tobacco weighing 650 mg). For example, when the amount added is 150 ppm, 97.5 ng (= 650 mg × 150 ppm) of the flavoring composition is dissolved in 10 μl of an ethanol solution of the flavoring composition. A cigarette was made using manufactured cigarette paper, and an organoleptic evaluation was performed.

2. Examples 3I-3M

Each flavoring composition was included in cyclodextrin. The aroma composition included in cyclodextrin was dispersed in an aqueous solution containing 6.0 wt.% Carboxymethyl cellulose in the same manner as in Study 1, and as a result, a dispersion was prepared. A grooved roller coater was used, and the dispersion was coated with a grooved roller into the center portion of a width of 7 mm of cigarette paper having a width of 27 mm. The added amount (parts per million) in Table 4 is the added amount of the flavoring composition, which was determined based on the added amount of the flavoring composition included in the cyclodextrin and the content ratio of each flavoring composition. A cigarette was made using manufactured cigarette paper, and an organoleptic evaluation was performed.

Organoleptic assessment

1) Assessment of adsorbed tobacco odor

The smoke that was formed during the burning of the cigarettes was adsorbed using each material, including polyester, cotton and hair, and the adsorbed tobacco smell was evaluated using a pairwise comparison method (blind assessment) of 48 of the company's own appraisers. A detailed description is provided below.

Polyester (polyester sample measuring 5 × 5 cm according to JIS Japanese industry standard), cotton (canequim cotton sample (unbleached plain weave muslin) No. 3 measuring 5 × 5 cm according to JIS standard) or hair (100% black human hair manufactured by Osaka Brush Co., Ltd.) was hung in each of a pair of containers having the same volume. A cigarette containing a flavoring composition and a cigarette not containing a flavoring composition were burned in each container, respectively, and a sidestream smoke was generated in the container. This sidestream smoke was adsorbed on each material in the container. After burning the cigarette, material was removed from each container, including the container in which the cigarette containing the flavoring composition was burned, and in the container in which the cigarette containing the flavoring composition was burned. The material was placed in a screw vessel to which a three-digit number was attached. Evaluation experts compared the tobacco odor adsorbed on the materials in the case of burning a cigarette containing a flavoring composition and in the case of burning a cigarette not containing a flavoring composition, and selected a material having a lower intensity of adsorbed tobacco smell.

In order to determine whether the flavoring composition being tested has the ability to reduce adsorbed tobacco odor or not, a binomial study (two-sided study) was carried out for a cigarette containing a flavoring composition and in the case of a cigarette not containing a flavoring composition, and the rating was set based on the following criteria:

good = there is a significant difference with a reliability of 95% or more;

satisfactory = there is a significant difference with a reliability of 90% or more; and

unsatisfactory = no significant difference.

2) Assessment of the total intensity of the aroma

Assessment of the total intensity of the aroma of each material on which tobacco smoke was adsorbed was carried out using a rating scale by three of the company's own expert appraisers. Evaluation points are determined as follows:

0 points = lack of aroma;

1 point = very low aroma intensity;

2 points = low aroma intensity;

3 points = not very low flavor intensity;

4 points = not very high flavor intensity;

5 points = high aroma intensity; and

6 points = very high flavor intensity.

The number of rating points of each sample was the arithmetic average of the rating points of three expert evaluators. Evaluation points were calculated to the first decimal place.

3) Assessment of aroma and taste during smoking

Evaluation of aroma and taste during smoking of manufactured cigarette samples using the rating scale was carried out by three of the company's own expert appraiser. Evaluation points are determined as follows:

1 point = very unsatisfactory aroma and taste during smoking;

2 points = unsatisfactory aroma and taste during smoking;

3 points = not very satisfactory aroma and taste during smoking;

4 points = not very good aroma and taste during smoking;

5 points = good aroma and taste during smoking; and

6 points = very good aroma and taste during smoking.

The number of rating points of each sample was the arithmetic average of the rating points of three expert evaluators. Evaluation points were calculated to the first decimal place.

The results of the study are presented in table 3 and table 4.

Table 3 Example 3A Comparative Example 3A Example 3B Example 3C Reference Example 3B 3D example Anisyl acetate 60 67 Anisyl formate fifteen 17 60 67 36 Citronellol Geraniol Propenylgualeol fifteen 17 Rodinol γ-decalactone 90 thirty 33 28 γ nonalactone 8 α-ionone β-ionone 10 10 10 28 Methylionone Total one hundred one hundred one hundred one hundred one hundred one hundred The results of organoleptic evaluation of adsorbed tobacco odor Amount to be added (parts per million) 150 150 150 150 150 245 Polyester Good Unsatisfactory Good Good Satisfactorily Good Cotton Satisfactorily Unsatisfactory Good Good Satisfactorily Good Hair Satisfactorily Unsatisfactory Good Good Satisfactorily Good The number of rating points for the total flavor intensity (average for all materials) 3,7 2,4 4.7 4.3 2,3 6.0 The number of estimated points of aroma and taste during smoking 4.3 3.0 4.0 4.3 3.0 2.0

(To be continued)

Table 3 Example 3E Example 3F Comparative Example 3C 3G example Example 3H 3D Comparative Example Anisyl acetate Anisyl formate Citronellol 27 40 Geraniol 10 fifteen Propenylgualeol Rodinol thirty 45 γ-decalactone 75 60 one hundred 75 γ nonalactone 10 α-ionone 25 β-ionone 25 thirty Methylionone 33 Total one hundred one hundred one hundred one hundred one hundred one hundred The results of organoleptic evaluation of adsorbed tobacco odor Amount to be added (parts per million) 150 150 150 150 150 150 Polyester Good Good Unsatisfactory Good Good Unsatisfactory Cotton Good Good Unsatisfactory Good Good Unsatisfactory Hair Good Good Unsatisfactory Good Good Unsatisfactory The number of rating points for the total flavor intensity (average for all materials) 5.3 5,0 2.7 5.3 4.3 3.0 The number of estimated points of aroma and taste during smoking 4.3 4.3 2,3 4.3 4.3 3.0

Table 4 Example 3I Example 3J Example 3K Example 3L Example 3M Anisyl acetate 60 Anisyl formate fifteen Citronellol 27 Geraniol 10 Propenylgualeol fifteen Rodinol thirty γ-decalactone 75 60 75 γ nonalactone 10 α-ionone 25 β-ionone 10 25 thirty Methylionone 33 Total one hundred one hundred one hundred one hundred one hundred The results of organoleptic evaluation of adsorbed tobacco odor Amount to be added (parts per million) 150 150 150 150 150 Polyester Good Good Good Good Good Cotton Satisfactorily Good Good Good Good Hair Satisfactorily Good Good Good Good The number of rating points for the total flavor intensity (average for all materials) 3.6 5.3 4.1 4.9 5.3 The number of estimated points of aroma and taste during smoking 3,1 4.0 3.0 3.9 4.0

From the results presented in table 3, the following information was determined.

By comparing Example 3A with Comparative Example 3A, comparing Example 3C with Comparative Example 3B, comparing Example 3G with Comparative Example 3C, and comparing Example 3H with Comparative Example 3D, the inventors found that the fragrance composition containing any ionone, including including α-ionon, β-ionon and methylionone, it has a significantly increased ability to reduce the adsorbed tobacco odor of each material, and also provides an increased overall aroma intensity, as well as improved aroma in cus during smoking compared to flavoring compositions that do not contain any ionon.

In addition, it was found that a flavoring composition containing ionon and γ-decalactone as another flavoring component, had an increased ability to reduce the adsorbed tobacco odor of each material and produced an increased flavor enhancement effect compared to a flavoring composition containing ionon and a flavoring component, different from γ-decalactone, as another flavoring component. For example, the flavoring composition in Example 3A, which does not contain γ-decalactone, had good ability to reduce adsorbed tobacco odor in the case of polyester, but showed a slightly lower ability to reduce adsorbed tobacco odor in the case of cotton or hair. On the other hand, in the case of flavoring compositions in Examples 3B-3G that contained γ-decalactone, a good ability to reduce the adsorbed tobacco smell of any of the materials, including polyester, cotton and hair, was shown.

In addition, when comparing Example 3A with Comparative Example 3A, where γ-decalactone is not contained in both cases, the coefficient of increase in flavor intensity is 3.7 / 2.4≈1.5; while when comparing example 3E with comparative example 3C, where γ-decalactone is contained in both cases, the coefficient of increase in flavor intensity is 5.3 / 2.7≈2.0. As described above, a flavoring composition containing ionon and γ-decalactone as another flavoring component produced a more significant aroma enhancing effect compared to a flavoring composition containing ionone and a flavoring component that was different from γ-decalactone as another flavoring component.

In addition, in the case where the flavoring composition consisted only of ionon and γ-decalactone, when the content of γ-decalactone is from 70 to 80 wt.% And the ionon content is from 20 to 30 wt.%, An especially good ability to reduce adsorbed tobacco odor, especially high overall aroma intensity, and also particularly good aroma and taste during smoking (Example 3E and Example 3G).

As can be seen from comparative example 3C, when γ-decalactone was used individually, the ability to reduce adsorbed tobacco odor was not manifested when the amount added was 150 ppm.

From the results presented in table 4, the following information was determined.

In addition, when the flavoring composition was included in cyclodextrin, and the resulting product was applied to cigarette paper to make a cigarette as shown in Examples 3I-3M, it became possible to obtain an enhancement effect of another flavoring component by ionone, and good adsorption reduction ability was observed. tobacco smell, as well as good aroma and taste during smoking.

Study 4

Investigated the preferred applied amount of a flavoring composition containing ionone.

Cigarette making

Each substance, including γ-decalactone and β-ionone, was included in cyclodextrin, which was applied to cigarette paper, and as a result a cigarette was made (DL-CD + BI-CD = 75 wt.% + 25 wt.%). The same cigarette used in Example 1A was used as a cigarette in all cases.

75 parts by weight were mixed. γ-decalactone included in cyclodextrin, and 25 parts by weight β-ionone included in cyclodextrin is in powder state. The mixed powder was dispersed in an aqueous solution containing 6.0 wt.% Carboxymethyl cellulose, and as a result, a dispersion was prepared. After that, this dispersion was applied to a central part having a width of 7 mm of cigarette paper 27 mm wide using a grooved roller coater. The amounts applied are shown in Table 5. The concentration of the fragrance-containing cyclodextrin composition was adjusted so that the desired surface density of the coating was obtained.

Using manufactured cigarette paper, a cigarette was made. The suitability for making cigarettes, the adsorbed tobacco smell, and the aroma and taste during smoking were evaluated.

As control, cigarette paper made in the same manner as described above was used, except that only γ-decalactone was contained in the cyclodextrin. Using manufactured cigarette paper with cyclodextrin containing only γ-decalactone, a cigarette was made. The suitability for making cigarettes, the adsorbed tobacco smell, and the aroma and taste during smoking were evaluated.

Suitability for making cigarettes

The assessment was carried out by staff members making cigarettes. Cigarettes were made by means of a cigarette-making device using manufactured cigarette paper. With the continuous production of 40,000 cigarettes, the frequency of production of defective cigarettes, the state of distribution of the cyclodextrin in the manufacture of the cigarettes, and the state of adhesion of the cyclodextrin to the roller feeding the cigarette paper, or to the part in contact with the cigarette paper, were observed. Suitability was comprehensively evaluated as follows:

good = making a very good cigarette;

satisfactory = cigarette making possible; and

unsatisfactory = cigarette making impossible.

Organoleptic assessment

1) Assessment of adsorbed tobacco odor

The smoke that formed during the burning of the cigarette was adsorbed on each material, and the adsorbed tobacco odor was estimated using the rating scale by 12 of the company's own expert evaluators. Evaluated samples were made in the same way as in the above study 3. The material used was polyester, cotton, hair and wool (a wool sample measuring 5 × 5 cm according to the JIS standard). Evaluation experts examined the adsorbed tobacco odor and evaluated the degree of reduction of the adsorbed tobacco odor. Appraisers examined each material. Evaluation points are determined as follows:

1 point = functionality (ability to reduce adsorbed tobacco odor) is absent;

2 points = almost no functionality;

3 points = functionality is present;

4 points = high functionality is present.

The number of rating points for each sample was the arithmetic average of the rating points of 12 expert evaluators. Evaluation points were calculated to the first decimal place.

2) Assessment of aroma and taste during smoking

Evaluation of aroma and taste during smoking of manufactured cigarette samples using the rating scale was carried out by four of the company's own expert appraiser. Evaluation points are determined as follows:

1 point = unsatisfactory (aroma and taste during smoking);

2 points = satisfactory;

3 points = not very good; and

4 points = good.

The number of rating points of each sample was the arithmetic average of the rating points of three expert evaluators. Evaluation points were calculated to the first decimal place.

The results are presented in table 5.

Table 5 Amount applied (parts per million) Suitability for making cigarettes DL-only CD DL-CD + BI-CD = 75 wt.% + 25 wt.% The number of estimated points of adsorbed tobacco odor The number of estimated points of aroma and taste during smoking The number of estimated points of adsorbed tobacco odor The number of estimated points of aroma and taste during smoking Polyester Cotton Hair Wool Polyester Cotton Hair Wool fifty Good 1,1 1,0 1,0 1,0 2.9 1.7 1.3 1.3 1.7 4.0 one hundred Good 1,1 1,0 1,1 1,1 2,5 2.7 2,4 2.6 2,3 3.8 150 Good 1,2 1,1 1.3 1.3 1.8 4.0 3.4 4.0 3.3 3.0 200 Satisfactorily 1.7 1.8 2.0 1.7 1,0 4.0 3,5 4.0 3,5 2.0 250 Unsatisfactory 2,3 2.0 2,3 2,3 1,0 4.0 3.6 4.0 3,7 1,0

From table 5 it was found that the preferred surface density of the coating of the flavoring composition was 100 ppm or more and 200 ppm or less, while providing satisfactory suitability for making cigarettes, the ability to reduce adsorbed tobacco odor, and aroma and taste in smoking process.

Claims (4)

1. A flavoring composition to reduce adsorbed tobacco odor, comprising:
an ionone selected from the group consisting of alpha-ionon, beta-ionon and methylionone, and
another flavoring component
in which the other flavoring component is only gamma decalactone, the content of gamma decalactone is from 70 to 80 wt.% and the ion content is from 20 to 30 wt.%. 2. A cigarette containing a flavoring composition according to claim 1. 3. The cigarette according to claim 2, in which the crushed tobacco wraps cigarette paper, and on the cigarette paper applied or sprayed flavoring composition included in cyclodextrin. 4. The cigarette according to claim 3, in which the applied amount of flavoring composition included in cyclodextrin is 100 parts per million or more and 200 parts per million or less.