JPH099947A - Tobacco aroma and flavor improver - Google Patents

Abstract

PURPOSE: To obtain a tobacco aroma and flavor improver containing equinatin, capable of well harmonizable with aroma of tobacco and giving roundness to aroma and emphasizing tobacco-like taste and suppressed in irritation and stabilized in quality by adding a small amount of equinatin to tobacco. CONSTITUTION: This tobacco aroma and flavor improver contains equinatin expressed by formula I and isolated and purified or synthesized. Furthermore, the amount of the tobacco aroma and flavor improver added to the cut tobacco is 1-100ppm based on weight of cut tobacco and the compound of formula I is obtained by carrying out aldol condensation of 4-hydroxy-2- methoxybenzaldehyde of formula III obtained by using 3-methoxyphenol of formula II as a starting raw material with p-hydrocyanetophenone of the formula IV.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a flavor and taste improving agent for tobacco.

[0002]

2. Description of the Related Art When raw material leaf tobacco is burned, it emits a flavor and taste peculiar to itself. It also exudes a nasty taste.

[0003] Conventionally, it has been empirically performed for a long time to correct such an inconvenient aroma and taste of cigarettes. For example, licorice, sugar, honey, rum, fruit juice, aromatic liquor, vanilla, and many other plant extracts are added to the raw material leaf tobacco to reduce the offensive odor and unpleasant taste of the raw material leaf tobacco.

On the other hand, in recent years, the taste of cigarettes has tended to diversify, and products having a light and rich flavor and taste have been favored. For this reason, as the raw material leaf tobacco to be blended with the product tobacco, those having a light aroma and mild nicotine and tar contents are often used.

Further, regenerated tobacco produced by denicotine treatment, plants other than leaf tobacco, and tobacco substitutes (hereinafter referred to as artificial tobacco) composed of various inorganic and organic components are also used.

[0006] Such raw materials for artificial tobacco generally have a poor flavor and taste, and often have a stimulative effect, and lack a good taste. Therefore, for example, the above-mentioned plant extract is added to improve the flavor and taste. There is.

[0007] As described above, among so-called tobacco flavor and taste improving agents that improve the flavor and aroma of tobacco by adding it to raw tobacco or artificial tobacco, especially plant extracts such as licorice extract improve flavor and aroma. Greatly contributes to

[0008]

However, in order to bring out the effect of improving the flavor and taste of the above-mentioned licorice extract, it is necessary to add a few% to the weight of the raw leaf tobacco. Moreover, since licorice is an agricultural product, it is susceptible to changes in the content components depending on the production area and annual production. As a result, it is cheap,
When producing tobacco of stable quality, there is a problem that the desired effect of improving the flavor and taste cannot be obtained.

The present invention has been made in view of the above points, and provides an aroma and taste improving agent which exhibits a remarkable aroma and taste improving effect characteristic of licorice extract and which is stable in quality by adding an extremely small amount. To do.

[0010]

[Means for Solving the Problems] In order to solve the above problems, the present inventors extensively searched for various compounds that have not been attempted to be used in tobacco. As a result, it was found for the first time that echinatin, which is a known natural substance present in licorice extract, exerts a remarkable flavor and taste improving effect characteristic of licorice extract by the addition of an extremely small amount to tobacco, and completed the present invention. did. That is, the present invention is a tobacco flavor and taste improving agent characterized by containing isolated and purified or synthesized echinatin represented by the formula shown in Chemical formula 2.

[0011]

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According to the present invention, a small amount of echinatin is added to a smoking article so as to be in good harmony with the original scent of tobacco and to impart a roundness to the scent, thereby enhancing the tobacco-likeness and suppressing irritation. And so on.

The method for producing echinatin, which is the active ingredient of the flavor and taste improving agent for tobacco of the present invention, includes the following methods. (1) Isolation and purification method from licorice extract Chloroform / methanol soluble part of licorice extract is fractionated sequentially with a solvent from n-hexane to ethyl acetate. The ether phase of the obtained fractions is further subjected to reverse phase silica gel column fractionation to obtain a crude echinatin fraction. The crude fraction is purified by high performance liquid chromatography to obtain echinatin.

(2) Synthetic method For example, a method represented by the reaction formula (1) shown in Chemical formula 3 is known (Chem. Pharm. Bull. 26 (1), 144 (1978), P.
hytochemistry, 19, 2179 (1980)).

[0015]

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First, 4-hydroxy-2-methoxy-benzaldehyde (3) is obtained from 3-methoxyphenol (2) by a Gattermann reaction. This compound (3) was aldol condensed with p-hydroxyacetophenone (4) to give echinatin.
(1) can be obtained.

Examples of smoking substances which can improve the flavor and taste by the addition of echinatin include, for example, cigarettes produced from ordinary leaf tobacco as raw materials, cigar cigarettes and pipe tobacco, for example, regenerated tobacco produced from waste tobacco, Alternatively, for example, synthetic tobacco produced by using natural fibers of plants other than tobacco or cultured plant plants as raw materials is included.

The means for adding echinatin to these smoking articles is not particularly limited. For example, as with other commonly used flavors, echinatin can be dissolved in an organic solvent such as ethanol or water and then added to the cut tobacco for use. Also, the material used to make cigarettes (eg glue).
Can also be contained. The amount of the flavor enhancer for tobacco of the present invention added is, for example, 0.01 ppm to 1000 ppm, preferably 1 ppm to 100 ppm, based on the cut weight of tobacco.
It is.

[0019]

The present invention will be described in detail with reference to the following examples. [A]. Production of Echinatin (1) Isolation and purification method from licorice extract 150 g of licorice extract chloroform / methanol extract
After dissolving in 50% methanol and washing with n-hexane, the methanol was removed and the mixture was extracted with diethyl ether. After fractionating the ether extract 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 successively with water / acetonitrile system. The effluent around 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 give 23.9 mg of echinatin. The spectral data of the echinatin obtained was in agreement 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 (linear gradient, 8: 2 to 5: 5, 50 minutes) Flow rate: 1 ml / min Detection: UV detection Instrument (Detection wavelength: 254 nm) <Spectral data>: Echinatin (derived from licorice extract) ¹³ C-NMR [CD ₃ OD] (ppm): 56.0, 99.9, 109.2, 116.3,
116.7, 119.4, 131.4, 131.7, 132.1, 141.3, 162.1, 16
3.1, 163.5, 191.6 ¹ H-NMR [CD ₃ OD] (ppm): 3.89 (3H, s, OMe), 6.43 (1H, d.
d, 8.6 / 2.3Hz, 5-H), 6.47 (1H, d, 2.3Hz, 3-H), 6.87 (2H, d,
8.8Hz, 3 '/ 5'-H), 7.60 (1H, d, 15.7Hz, Hα), 7.60 (1H, d, 8.
2Hz, 6-H), 7.95 (2H, d, 8.8Hz, 2 '/ 6'-H), 8.03 (1H, d, 15.7H
z, Hβ) EI mass spectrum (m / e, relative intensity): 270 (50), 255 (37),
239 (67), 177 (56), 121 (100), 93 (90) FAB mass spectrum [m-nitrobenzyl alcohol]: 2
71.07 (M + H) UV absorption spectrum [0.1% phosphoric acid / acetonitrile, 35: 6
5] λmax (nm): 237, 312, 370

(2) Synthetic method 10 g of zinc cyanide was suspended in ether, 5 g of 3-methoxyphenol (2) was added, and hydrogen chloride gas was blown thereinto to react for 2 hours. After ether was added to the lower phase for washing, ice water was added to the product and the mixture was stirred. The mixture was heated to 60 ° C. to volatilize the ether and left overnight at room temperature. The reaction mixture was extracted with ether to remove the solvent, and the obtained crude crystals were filtered and washed with carbon tetrachloride and recrystallized from ethyl acetate / hexane to give 2.2 g of 4-hydroxy-2-methoxy-benzaldehyde (3). Obtained.

1.1 g of p-hydroxyacetophenone (4)
(3) 1.5 g was dissolved in ethanol, added to 60% potassium hydroxide, and reacted at 60 ° C. for 3 days. The reaction mixture was poured into ice water, adjusted to pH 3 with concentrated hydrochloric acid, extracted with ether,
The solvent was removed to obtain 1.0 g of (1).

The spectral data of the echinatin obtained was as follows. <Spectral data>: Echinatin (synthetic) IR spectrum [KBr] (cm ^-1 ): 1623 (CO-CH = CH-phenyl) ¹³ C-NMR [CD ₃ OD] (ppm): 56.0, 99.9, 109.2, 116.3,
116.7, 119.4, 131.4, 131.6, 132.1,141.3, 162.1, 16
3.1, 163.5, 191.6 ¹ H-NMR [CD ₃ OD] (ppm): 3.89 (3H, s, OMe), 6.44 (1H, d.
d, 8.6 / 2.3Hz, 5-H), 6.47 (1H, d, 2.3Hz, 3-H), 6.87 (2H, d,
8.8Hz, 3 '/ 5'-H), 7.60 (1H, d, 15.7Hz, Hα), 7.61 (1H, d, 8.
9Hz, 6-H), 7.96 (2H, d, 8.9Hz, 2 '/ 6'-H), 8.03 (1H, d, 15.7H
z, Hβ) High resolution FAB mass spectrum [m-nitrobenzyl alcohol] mass: 271.09855 (C ₁₆ H ₁₄ O ₄ + H) EI mass spectrum (m / e, relative intensity): 270 (49), 255 (33) ,
239 (70), 177 (54), 121 (100), 93 (70) UV absorption spectrum (0.1% phosphoric acid / acetonitrile, 35: 6)
5) λmax (nm): 237, 312, 370

[B]. Sensory test (1) Improvement of flavor and aroma of leaf tobacco Echinatin ethanol solution was added to the cut tobacco at 0.1, 1, 10 and 100 pp per unit weight of cut tobacco.
It was sprayed uniformly so that the particle size became m. After that, the tobacco pieces were wrapped with paper to produce a fragrance product. For these perfumed products,
As a control, the rolled product of chopped tobacco without echinatin added,
The two-point comparison method was used to compare the scent, taste, and irritation when smoking. The evaluations of 20 professional sensory test panels are shown in Table 1.

The sensory test was 0 points when there was no difference between the test sample and the control sample, 2 points when there was a slight difference, and 3 points when there was a very large difference. The score was rated as (+) when the score was good, and as (−) when the score was bad. The test sample was judged 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, it was confirmed that echinatine significantly improved the taste and irritation of tobacco.

[0026]

[Table 1]

(2) Improvement of flavor and taste of regenerated tobacco Waste tobacco was extracted with hot water at 100 ° C. and separated into a water-soluble part and a water-insoluble part. Next, the water-insoluble part was beaten, and 15% of the dry matter weight of softwood kraft pulp was added thereto. The obtained mixture was formed into a thin paper, and the water-soluble portion was returned to the thin paper to prepare a sheet-shaped regenerated cigarette. An ethanol solution of echinatine was uniformly sprayed onto the regenerated cigarette so that the added amount was 1, 10, 100 and 1000 ppm per unit weight of the regenerated cigarette, and then chopped and rolled to produce a fragrance product. For these fragranced products, the scent when smoking was used as a control, with the rolled product of tobacco cut with no echinatin added,
These tastes were compared in terms of taste and stimulus by the two-point comparison method. The evaluations of 20 professional sensory test panels were as shown in Table 2.

In the sensory test, when there was no difference between the test sample and the control sample, 0 point was given, when there was a slight difference, 2 points were given, and when there was a very different difference, 3 points were given. The score was rated as (+) when the score was good, and as (−) when the score was bad. The test sample was judged 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 and taste improving agent of the present invention is added to a smoking material in a small amount so as to be in good harmony with the original aroma of tobacco and to impart a roundness to the aroma. , And has a remarkable effect such that the cigarette is emphasized and the stimulation is suppressed.

 ─────────────────────────────────────────────────── ─── Continued Front Page (72) Inventor Masataka Mori 6th, Umegaoka, Aoba-ku, Yokohama, Kanagawa Pref. Tobacco Central Research Institute, Tobacco Inc.

Claims (1)

[Claims] 1. A tobacco flavor taste improving agent comprising isolated and purified or synthesized echinatin represented by the formula shown in Chemical formula 1. Embedded image