JP3187916B2 - Tobacco flavor enhancer - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a tobacco flavor enhancer.

[0002]

2. Description of the Related Art Burning of raw tobacco emits its own unique flavor, and at the same time stimulates tobacco,
It also has off-flavors such as blue odor or fresh odor, as well as aversions such as astringency and 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 liquor, vanilla, and many other plant extracts have been added to raw leaf tobacco to reduce the off-flavor and unpleasant taste of raw leaf tobacco.

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

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

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

[0007] Among the components contained in the so-called tobacco flavor-enhancing agent which is added to raw leaf tobacco or artificial tobacco to improve the flavor of tobacco, particularly, for example, l-
Terpene compounds such as menthol and borneol contribute significantly to the improvement of flavor.

[0008]

However, the above-mentioned terpene compounds are generally easily volatilized. For this reason, the terpene compound volatilizes during the manufacturing process and the storage period of tobacco. The terpene compound is volatilized or thermally decomposed at, for example, 70 ° C. to 150 ° C. based on the result of thermogravimetric analysis. For this reason, in the tobacco manufacturing process, for example, in a process such as a drying process and a puffing process, the tobacco is exposed to a high temperature, and the terpene compound is volatilized or thermally decomposed. As a result, most of the terpene compound added to the raw leaf tobacco is lost, and there is a problem that the desired flavor-improving effect cannot be obtained.

The present invention has been made in view of the above points, and provides a tobacco taste improver which is stable during the manufacturing process and the storage period of tobacco and can exert a sufficient flavor improving effect when smoking. Things.

[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 used in tobacco. As a result, glucosides of l-menthol and borneol among the terpene compounds are non-volatile and stable under high-temperature conditions during the manufacturing process and storage period, but are thermally decomposed during smoking to provide an excellent flavor-improving effect. It has been found that the present invention can be exerted, and the present invention has been completed.

That is, the present invention provides a tobacco flavor improving agent comprising a terpene glucoside represented by the following general formula:

[0012]

Embedded image (Where R is

[0013]

Embedded image Or

[0014]

Embedded image The glucosides of l-menthol and borneol according to the present invention (hereinafter referred to as terpene glucosides) are white solids having no odor per se. Terpene glucoside does not thermally decompose at the temperature conditions of the manufacturing process and the storage period of tobacco, that is, at 20 ° C to 200 ° C, but at the temperature condition at the time of smoking, that is, at 350 ° C to 900 ° C near the tobacco burning cone. Decomposes to form terpene compounds (1-menthol and borneol). Actually, as a result of analyzing the smoke component of the cigarette to which terpene glucoside was added by gas chromatography, terpene was detected.

[0015] The terpene compound thus produced improves the taste of tobacco. As a result, the active ingredient can be prevented from being volatilized and thermally decomposed during the manufacturing process and the storage period of the tobacco, and at the same time, an extremely excellent flavor and taste improving effect can be obtained during smoking. That is, by adding a small amount of terpene glucoside to a smoking article, it is in excellent harmony with the original scent of tobacco, and gives the scent a roundness, which enhances tobacconess and suppresses irritation. And these effects are sustained for a long time.

As a method for producing terpene glucoside, which is an active ingredient of the flavor enhancer for tobacco of the present invention, for example, a method represented by reaction formula (1) shown in Chemical formula 7 is known (Agricultural and Biological). Chemistry, 43,3
07 (1979), CHEMISTRY LETTERS, 431, (1981)).

[0017]

Embedded image (Where RH represents a terpene compound and Ac represents acetyl) First, the terpene compound RH and pentaacetyl-β-D-
After glucose is polymerized using zinc chloride or tin chloride as a catalyst, terpene glucoside is obtained by deacetylation with sodium ethoxide or sodium methoxide.
The terpene glucoside thus obtained can be purely separated from unreacted substances by, for example, silica gel column chromatography or recrystallization.

Examples of smoking articles which can improve the flavor and taste by the addition of terpene glucoside include, for example, cigarettes, cigars and pipe tobaccos produced using ordinary leaf tobacco as raw materials, such as regenerated tobacco produced using scrap tobacco as raw materials. Or, for example, synthetic tobacco produced from natural fibers of plants other than tobacco or plant culture plants.

The means for adding terpene glucoside to these smoking articles need not be particularly limited, and the terpene glucoside can be dissolved in an organic solvent such as ethanol or water, like other commonly used fragrances. After the addition, it can be added to the tobacco cut and used. Also, it can be contained in a material for cigarette manufacturing (for example, glue).

The added amount of the tobacco flavor enhancer of the present invention is as follows:
For example, based on the tobacco cut weight, 0.1 ppm to 1000 ppm
, Preferably 1 ppm to 100 ppm.

[0021]

The present invention will be described below in detail with reference to examples.

Preparation of terpene glucoside (1) Preparation of l-menthol-β-D-glucoside Starting from 5 g of l-menthol and 12.5 g of pentaacetyl-β-D-glucose, the above-mentioned Agricultural and Biolo
According to the method disclosed in gical Chemistry, 43, 307 (1979) (hereinafter referred to as Reference Document 1), a terpene glucoside, 1-menthol-β-D-glucoside mixture, was obtained. This mixture was recrystallized in a solvent of ethanol: water = 1: 1 and separated pure to obtain 4.6 g of terpene glucoside as a white solid. The spectrum data of the obtained terpene glucoside was as follows.

L-menthol-β-D-glucoside Nuclear magnetic resonance spectrum (CD ₃ OD): δ (ppm) 0.84 (3H, d, J = 7 Hz), 0.86 (3H, d, J = 6 Hz), 0.90 ( 3H, d, J = 7H
z), 1.20-1.40 (3H, m), 1.63 (4H, m), 2.25 (3H, m), 4.36 (1H,
d, J = 8Hz), 3.86-3.12 (6H, m) Infrared absorption spectrum (KBr) :( cm ^-1 ) 3400 (OH), 1387 (isopropyl group) (2) Production of borneol-β-D-glucoside borneol 5 g and pentaacetyl-β-D-glucose
An acetylated terpene glucoside mixture was obtained according to the method disclosed in Reference 1 using 12.5 g as a starting material. The mixture was fractionated by silica gel column chromatography, the fraction eluted with hexane: ethyl acetate = 1: 1 was collected, deacetylated, and further ethanol: water =
Recrystallization in a 1: 1 solvent and pure separation gave 2.9 g of terpene glucoside as a white solid. The spectrum data of the obtained terpene glucoside was as follows.

Borneol-β-D-glucoside nuclear magnetic resonance spectrum (CD ₃ OD): δ (ppm) 0.87 (9H, 3s), 1.21 (3H, m), 1.58 (3H, m), 2.14 (2H, m ), 3.18-
4.14 (6H, m), 4.26 (1H, d, J = 8Hz) Infrared absorption spectrum (KBr) :( cm ^-1 ) 3350 (OH), 1370 Below, 1-menthol-β-D produced in this manner
-Glucoside and borneol-β-D-glucoside were used to conduct a thermal decomposition test and a sensory test.

Thermal Degradability Test The thermal degradability of terpene glucoside was determined by determining the weight loss onset temperature from the thermogravimetric curve obtained when the sample was heated at a heating rate of 10 ° C./min using a differential scanning calorimeter. evaluated. The determination of the weight loss start temperature is based on Japanese Industrial Standards (J
IS) Plastic thermogravimetry (K)
7120-1987).

As terpene glucosides, 1-menthol-β-D-glucoside and borneol-β-D-
The glucoside was subjected to thermogravimetry under the following analysis conditions, and the weight loss onset temperature was determined. Then, as a terpene,
For 1-menthol and borneol, thermogravimetry was performed under the same analysis conditions to determine the weight loss onset temperature. Table 1 shows the results.

Analysis conditions Apparatus: Differential scanning calorimeter (TG-DSC, Rigaku C)
orp., DPS-8151) Atmosphere: Helium 50ml / min Air flow Measurement temperature: Approx. 40 ° C to 500 ° C (heating rate 10 ° C / min) Sample weight: 4 to 10mg

[0028]

[Table 1] As is clear from Table 1, the temperature at which the terpene glycoside starts to lose weight is higher than the temperature condition of 20 ° C. to 200 ° C. (hereinafter referred to as “manufacturing / storage temperature”) during the manufacturing process and the storage period of tobacco. Temperature around the cone 350
C. to 900 C. (hereinafter referred to as smoking temperature). Thereby, it was confirmed that the compound exists stably without volatilizing or decomposing during production and storage, and can exhibit a flavor-improving effect by volatilizing or thermally decomposing during smoking.

On the other hand, the terpene weight loss starting temperature is determined by
Lower than the maximum storage temperature. Therefore, it was confirmed that the tobacco was thermally decomposed during the production and storage period.

Sensory Test (1) Improving Flavor Taste of Leaf Tobacco Ethanol solution of l-menthol-β-D-glucoside and borneol-β-D-glucoside in leaf tobacco cuts for Seven Star (brand name) (Japanese tobacco trade name) Of 1 ppm and 10 ppm
It was sprayed uniformly to be ppm. Thereafter, the tobacco cut was rolled into cigarettes to produce perfumed products. These flavored products were compared by a two-point discrimination method with respect to the fragrance, taste, and habit when smoking, using the cigarette-cut rolled product without terpene glucoside as a control. The evaluations of the 20 panelists were as shown in Table 2.

The perfumed products 1 and 2 represent l-menthol-β-D-glucoside and borneol-β-D-glucoside, respectively, and the numbers in the table indicate the number of persons evaluated as good. The mark indicates that there is a significant difference at 5%.

[0032]

[Table 2] As is clear from Table 2, 1-menthol-β-D-glucoside and borneol-β-D-glucoside are:
All were confirmed to significantly improve the tobacco aroma, taste and habit.

(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. An ethanol solution of l-menthol-β-D-glucoside and borneol-β-D-glucoside was added to the regenerated tobacco at an amount of 10 ppm and 100 ppm per unit weight of the regenerated tobacco.
After spraying uniformly, the resultant was cut and wound up to produce a flavored product. The taste of these flavored products was compared by using a two-point discrimination method with respect to the aroma, taste and irritation when smoking, using a rolled product made of regenerated tobacco without pentaglucoside as a control. Professional sensory test panel 20
The evaluation of the names was as shown in Table 3.

In Table 3, the flavored products 1 and 2 are 1-menthol-β-D-glucoside and borneol-β, respectively.
-D-glucoside, the numbers in the table indicate the number of people evaluated as good, and the * mark indicates that there is a significant difference at 5%.

[0035]

[Table 3] From Table 3, it was recognized that l-menthol-β-D-glucoside and borneol-β-D-glucoside both have an effect of remarkably improving aroma and taste and suppressing irritation.

[0036]

As described above, the tobacco flavor enhancer of the present invention is non-volatile and stable during the manufacturing process and the storage period of tobacco, and volatilizes or thermally decomposes during smoking to produce active ingredients. . This makes it possible to substantially completely prevent the active ingredient from being lost during the production and storage periods, and to exhibit a remarkable effect such as an excellent flavor and taste improving effect during smoking.

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Yasuhiro Shinozaki 6-2, Umegaoka, Midori-ku, Yokohama-shi, Kanagawa Pref. Japan Tobacco Inc. Tobacco Central Research Institute (72) Inventor Toshiaki Matsuzaki 6 Umegaoka, Midori-ku, Yokohama-shi, Kanagawa Address 2 Inside the Tobacco Central Research Laboratory, Tobacco Inc. Japan (56) References JP-A-3-47177 (JP, A) JP-A-4-267870 (JP, A) JP-A-3-266969 (JP, A (58) Fields surveyed (Int. Cl. ⁷ , DB name) A24B 15/40 A24B 3/12

Claims (1)

(57) [Claims] 1. A tobacco flavor enhancer comprising a terpene glucoside represented by the general formula shown in Chemical formula 1. Embedded image (Wherein R is Or Represents)