JP3215787B2 - Tobacco flavor enhancer - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a flavor enhancer for tobacco.

[0002]

2. Description of the Related Art Raw leaf tobacco emits a peculiar and pleasant taste when burned, but at the same time, eliminates the stimulus, green odor or fishy odor peculiar to leaf tobacco, as well as astringency,
It also has a bitter taste, such as bitterness.

Hitherto, it has been empirical to rectify such inconvenient flavors of tobacco for a long time. For example, licorice, sugar, honey, rum, fruit juice, aromatic wine, vanilla, and many other plant extracts have been added to raw leaf tobacco to reduce the habit and taste of raw leaf tobacco.

[0004] On the other hand, in recent years, the taste of tobacco has been diversifying, and products that are light and rich in flavor have been favored. For this reason, as the raw leaf tobacco to be blended with the product tobacco, those having a light flavor and moderate nicotine and tar contents are often used.

[0005] In addition, regenerated tobacco produced by subjecting to denicotine treatment, tobacco substitutes (hereinafter referred to as artificial tobacco) comprising plants other than leaf tobacco or various inorganic and organic components are also used.

[0006] Such artificial tobacco raw materials generally have poor flavor, lack flavor and are often irritating. For example, the above-mentioned plant extract is added to improve the flavor. ing.

[0007] As described above, substances that improve the taste of tobacco by adding to raw leaf tobacco or artificial tobacco are generally called tobacco flavor enhancers. Among these tobacco flavor enhancers, plant extracts such as licorice extract, for example, contribute significantly to the improvement of flavor.

[0008]

However, in order to achieve the above-mentioned effect of improving the flavor and taste of the licorice extract, it is necessary to add several percent to the weight of the raw leaf tobacco. In addition, since licorice is an agricultural product, it is susceptible to changes in content components depending on the place of production and annual production. As a result, when producing cheap tobacco with stable quality, there is a problem that the desired flavor and taste improvement effect cannot be obtained.

[0009] The present invention has been made in view of the above-mentioned points, and is intended to provide a flavor-improving agent exhibiting a remarkable flavor-improving effect, which is characteristic of a licorice extract, and having a stable quality by adding a trace amount thereof. To provide.

[0010]

Means for Solving the Problems In order to solve the above-mentioned problems, the present inventors have conducted a wide search for various compounds which have not been tried to use in tobacco. As a result, it has been found for the first time that apigenin, which is a known natural substance present in licorice extract, exerts a remarkable flavor-improving effect characteristic of licorice extract by adding a trace amount to tobacco, and completed the present invention. . That is, the present invention provides
The present invention relates to a tobacco flavor improving agent containing apigenin, which is isolated, purified or synthesized, represented by the following formula:

[0011]

Embedded image

According to the present invention, by adding a small amount of apigenin to a smoking article, the fragrance is harmonized with the original scent of the tobacco, and the scent is rounded to enhance the tobacco quality and to reduce irritation. It is possible to obtain an excellent effect such as the above.

[0013]

BEST MODE FOR CARRYING OUT THE INVENTION Apigenin, which is an active ingredient of the flavor improving agent for tobacco of the present invention, can be produced, for example, by the following method. (1) Isolation / Purification Method from Licorice Extract The chloroform-methanol soluble part of licorice extract is fractionated sequentially with a solvent ranging from n-hexane to ethyl acetate. The ether phase of the obtained fraction is further subjected to reverse phase silica gel column fractionation to obtain a crude apigenin fraction. This crude fraction is purified by high performance liquid chromatography to obtain apigenin.

(2) Synthetic method For example, Archiv der Pharmazie (Weinheim, German) is known which has a method as shown in the reaction formula (1) shown in Chemical formula 3.
y), 316, 219 (1983).

[0015]

Embedded image

The known natural compound naringenin (2) is
Apigenin (1) can be obtained by heating with excess iodine in a pyridine solvent, for example, at 90 ° C. for 10 hours. In addition, naringenin (2) is a bitter component of grapefruit, and can be obtained easily and inexpensively.

Although the tobacco flavor improving agent of the present invention is based on the effect of apigenin, other flavor improving components and additives may be mixed. Among them, licorice components are also included. Therefore, according to the present invention, it is also possible to prepare a composition similar to the licorice extract, and such a similar composition is also included in the present invention. However, such a simulated composition is completely different from natural licorice extract, and in particular, is completely different from natural licorice extract in that the content of apigenin can be arbitrarily and precisely controlled.

Examples of smoking articles which can improve flavor and taste by adding apigenin include, for example, cigarettes, cigarettes and pipe tobaccos manufactured using ordinary leaf tobacco as a raw material, such as regenerated tobacco manufactured using scrap tobacco as a raw material, Or, for example, natural tobacco other than tobacco or synthetic tobacco produced from plant culture plants is included.

The flavor enhancer of the present invention is particularly effective especially when applied to tobacco products containing Burley variety. This is because Burleigh leaf tobacco is more irritating than other leaf tobaccos, so that the effect of the flavor enhancer of the present invention appears more remarkably. In addition, the ability to alleviate the unique stimulus of the burley variety has a special significance in meeting the recent taste of enjoying light flavor. That is, tobacco that emphasizes lightness usually sacrifices the response to drinking that is unique to tobacco. In contrast, Burley leaf tobacco has a great effect of imparting a unique drinking response to tobacco. Thus, the ability to mitigate the unique irritations of Burley can be blended with modern tobacco products that have a lighter flavor without the unique irritations, and have been sacrificed to achieve lightness. It means that it is possible to provide tobacco.

The means for adding apigenin to these smoking articles is not particularly limited. For example, as with other commonly used fragrances, apigenin can be dissolved in an organic solvent such as ethanol or water and then added to tobacco cuts for use. Further, it can be contained in a material (for example, a paste) for producing cigarettes.

The added amount of the flavor enhancer for tobacco of the present invention is 0.01 to 1000 ppm, preferably 0.1 to 1000 ppm, based on the tobacco cut weight, as the amount of apigenin.
10 ppm.

[0022]

The present invention will be described in detail with reference to the following examples. I. Production of apigenin (1) Isolation and purification from licorice extract
After dissolving in 50% methanol and washing with n-hexane, methanol was removed and extracted with diethyl ether. After the ether extract was fractionated with chloroform / methanol / water, the upper phase was fractionated with ether / water. The ether phase was subjected to reverse phase silica gel column chromatography, and eluted sequentially with water / acetonitrile. The effluent near water / acetonitrile (6: 4) was collected and concentrated under reduced pressure to obtain a crude fraction. The crude fraction was purified by high performance liquid chromatography under the following conditions. The elution time was 25.5 minutes. The eluate was extracted with ethyl acetate, and dried under reduced pressure to obtain 1.2 mg of apigenin. The spectrum data of the obtained apigenin agreed with the data of the synthetic product and the literature values.

<High performance liquid chromatography conditions> Column: Reversed phase silica gel column Solvent: 0.1% phosphoric acid / acetonitrile (8: 2 to 5: 5, linear gradient 50 minutes) Flow rate: 1 ml / min Detection: UV detector (Detection wavelength: 254 nm) <Spectral data> Apigenin (derived from licorice extract) ¹ H-nuclear magnetic resonance spectrum [CD ₃ OD] (ppm): 6.19 (1H, d,
J = 2.1Hz, 6-H), 6.44 (1H, d, J = 2.1Hz, 8-H), 6.58 (1H, s, 3-
H), 6.92 (2H, d, J = 8.9Hz, 3 '/ 5'-H), 7.85 (2H, d, J = 8.9Hz,
2 '/ 6'-H) High resolution FAB mass spectrum [glycerol + _{thioglycerol]: 271.06367 (C 15 H 10} O 5 + H) UV absorption spectrum [0.1% phosphoric acid / acetonitrile, 65: 3
5] λmax (nm): 266, 339 (2) Synthesis method 2.72 g of naringenin (2) 2.5 g of iodine in 15 ml of pyridine
At 90 ° C. for 8 hours. The reaction mixture was cooled on ice,
After adding 40 ml of 7.5% sodium hydroxide, add glacial acetic acid
The pH was adjusted to 5.3. The resulting crystals were filtered by suction, and recrystallized from a mixed solvent of dimethylformamide and water to obtain 2.55 g (86% yield) of pure apigenin (1) crystals.

The spectrum data of the obtained apigenin are as follows, and completely matched those derived from the licorice extract. <Spectral data> Apigenin (synthetic product) ¹ H-nuclear magnetic resonance spectrum [CD ₃ OD] (ppm): 6.19 (1H, d,
J = 2.1Hz, 6-H), 6.44 (1H, d, J = 2.1Hz, 8-H), 6.58 (1H, s, 3-
H), 6.92 (2H, d, J = 8.9Hz, 3 '/ 5'-H), 7.85 (2H, d, J = 8.9Hz,
2 '/ 6'-H) High resolution FAB mass spectrum [glycerol + _{thioglycerol]: 271.06367 (C 15 H 10} O 5 + H) UV absorption spectrum [0.1% phosphoric acid / acetonitrile, 6
5:35] λmax (nm): 266, 339 II. Sensory test (1) Improving the flavor and taste of leaf tobacco Mild Seven (brand name) (trade name of Nippon Tobacco Co., Ltd.) was added to a leaf tobacco cut (burley type) with an ethanol solution of apigenin, and the amount added was 0.
It sprayed uniformly so that it might be set to 01, 0.1, 1, and 10 ppm.
Thereafter, the tobacco cut was rolled into cigarettes to produce perfumed products. These scented products were compared by a two-point comparison method for the scent, taste, and irritation when smoking, using a cigarette-cut rolled product without apigenin as a control. Professional sensory test panel 20
The evaluation of the names was as shown in Table 1.

In the sensory test, 0 point is given when there is no difference between the test sample and the control sample, 2 points when there is a slight difference, and 3 points when there is a very large difference. Is rated as (+) when good and as (-) when bad. The test sample was determined as a blind sample so that the contents of the test could not be understood. The results are shown in Table 1. As is clear from Table 1, apigenin was confirmed to significantly improve the taste and irritation of tobacco.

[0026]

[Table 1]

(2) Improving Flavor Taste of Recycled Tobacco Scrap tobacco was extracted with hot water at 100 ° C. and divided into a water-soluble part and a water-insoluble part. Next, the water-insoluble portion was beaten, and to this was added 15% of its dry matter softwood kraft pulp. The resulting mixture was formed into a thin paper, and the water-soluble portion was returned to the thin paper to produce a sheet-shaped regenerated tobacco. The regenerated tobacco was sprayed uniformly with an ethanol solution of apigenin in an amount of 0.1, 1, 10, and 100 ppm per unit weight of the regenerated tobacco, and then cut and wound to produce a flavored product. . For these flavored products, the scent when smoking was used as a control, with the cigarette-chopped rolled product without apigenin as a control,
These tastes were compared for taste and irritation by a two-point comparison method. The evaluations of the 20 panelists were as shown in Table 2.

In the sensory test, 0 point is given when there is no difference between the test sample and the control sample, 2 points when there is a slight difference, and 3 points when there is a very large difference. Is rated as (+) when good and as (-) when bad. The test sample was determined as a blind sample so that the contents of the test could not be understood. The results are shown in Table 2.

[0029]

[Table 2]

[0030]

As described above, the tobacco flavor-enhancing agent of the present invention, by adding a small amount to a smoking article, harmonizes well with the original scent of tobacco and imparts a rounded scent. It has remarkable effects such as emphasizing tobacco and suppressing stimulation.

Continued on the front page (72) Inventor Michinori Yokoi 6-2 Umegaoka, Aoba-ku, Aoba-ku, Yokohama-shi, Kanagawa Pref. Japan Tobacco Inc. Tobacco Central Research Institute (72) Inventor Masataka Mori 6-2 Umegaoka, Aoba-ku, Yokohama-shi, Kanagawa Japan Tobacco Inc. (56) References JP-A-64-2565 (JP, A) JP-A-5-199860 (JP, A) JP-A-55-57583 (JP, A) JP-A-2-101013 (JP, A) (58) Field surveyed (Int. Cl. ⁷ , DB name) A24B 15/40 A24B 3/12 C07D 311/30

Claims (3)

(57) [Claims] 1. A tobacco flavor enhancer comprising an isolated and purified or synthesized apigenin represented by the formula shown in Chemical formula 1. Embedded image 2. Based on the applied tobacco cut weight,
Apigenin is added in an amount of 0.01 ppm to 1000 ppm, preferably 0.1 ppm.
The tobacco flavor enhancer according to claim 1, which is applied so as to be 1 ppm to 10 ppm. 3. The tobacco flavor enhancer according to claim 1, which is applied to a leaf tobacco raw material of Burley variety.