JPH058667B2 - - Google Patents

Description

[Detailed description of the invention]

(Industrial Application Field) The present invention is based on the general formula [However, n is 9 or 10 and R is

[Formula] or

[Formula]] This invention relates to a tobacco flavor improver comprising coenzyme Q (R=) or its reduced form (R=) represented by the following formula, and is a technology used in the tobacco industry. Coenzyme Q has the general formula It is a general term for compounds represented by the number n, such as coenzyme Q ₉ [hereinafter referred to as compound (1)], coenzyme Q ₁₀ [hereinafter referred to as compound (2)], and is widely used in animals and plants. It exists in the world as an essential component of the electron transport system. In addition, the reduced form of coenzyme Q ₉ represented by n=9 and R= is the following compound (3), n=10,
The reduced form of coenzyme Q ₁₀ represented by R= will be hereinafter referred to as compound (4). (Prior Art) Many compounds originally contained in leaf tobacco are known as substances effective in improving the aroma and taste of tobacco. Ionone compounds, which are carotenoid decomposition products, and sesquiterpenoids are representative compound groups. (Problems to be Solved by the Invention) In recent years, preferences for cigarettes have shown a tendency to diversify, and in particular, preferences are shifting toward products that are light in taste and rich in aroma. In line with this trend, many leaf tobaccos are being used as raw material for tobacco products, with a light taste and low nicotine and tar content. In addition, so-called artificial cigarettes (hereinafter referred to as "artificial cigarettes") made of leaf tobacco produced by removing nicotine, plants other than leaf tobacco, or various inorganic and organic components have also come into use. However, such tobacco raw materials generally lack aroma and are often irritating and lack flavor, so it is necessary to add some substance to improve the aroma and taste. (Means for Solving the Problems) The present inventors have conducted intensive research to solve the above problems, and have particularly improved the taste of cigarettes made from leaf tobacco, artificial tobacco, etc., which lack aroma and flavor. We conducted a search for compounds that cause Coenzyme Q, which is easily available by synthesis, and its reduced forms, compounds (1) to (4), were added to various tobacco raw materials that lack aroma and taste and are irritating, and tests were conducted to evaluate their aroma and taste. However, compound (1)
- (4) have many excellent effects, such as harmonizing well with the original tobacco aroma, giving the aroma a roundness, emphasizing the tobacco-like character, suppressing irritation, and having these effects last long. found. The timing and means of adding compounds (1) to (4) to tobacco raw materials are not particularly limited, and they can be added to shredded tobacco after being dissolved in an organic solvent such as ethanol, like other commonly used flavorings. It can also be used to improve flavor and aroma by incorporating it into other materials for manufacturing cigarettes, such as wrapping paper, glue, or filters. There are no particular restrictions on the types of tobacco to which compounds (1) to (4) can be applied, including cigarettes made from regular leaf tobacco, pipe tobacco, cigar tobacco, etc., as well as natural fibers or plant tissue culture. The flavor and aroma of artificial cigarettes can also be improved by adding the present compound during the manufacturing process or after the product is manufactured. The amount of the present compound to be added may be extremely small, and a sufficient effect can be obtained by adding 0.00001 to 0.01% (by weight), preferably 0.0001 to 0.001% (by weight) to the tobacco or tobacco manufacturing materials. Example 1 Japan Tobacco brand name “Cheery” just before rolling
A 0.01% by weight ethanol solution of compound (1) was added to 50 g of shredded tobacco.
After spraying and adding compound (1) to an amount of 0.0001% by weight, it was rolled up into paper, and the odor and taste when smoked were compared with the above-mentioned rolled tobacco without compound (1) added. Comparisons were made using the two-point discrimination method. Rated first by a specially trained expert panel of 20
It was as shown in the table.

[Table] From the above table, it can be seen that compound (1) has the effect of significantly improving the odor and taste of tobacco products. Example 2 Waste tobacco was extracted with hot water at 100°C, separated into a water-soluble part and a water-insoluble part, and then the water-insoluble part was beaten, and coniferous kraft pulp corresponding to 15% of its dry weight was added. The mixture was molded into a thin paper, and compound (1) was added in the same manner as in Example 1 to 60 g of sheet-shaped recycled tobacco made by returning the water-soluble portion to the thin paper so that the amount of addition was 0.0005% by weight. After spraying and adding it, it was shredded and rolled up, and the odor, taste, and irritation when smoked were evaluated using the two-point discrimination method using the shredded and rolled-up products of the above sheet-shaped recycled tobacco without the addition of compound (1) as a control. compared. The evaluations of 20 specially trained expert panels were as shown in Table 2.

【represent.
* indicates a significant difference at a 5% risk rate
shows.
The results show that the odor and taste are significantly improved in the products to which Compound (1) is added, and the irritation suppressing effect is also significant. Example 3 0.01 of compound (2) for 50 g of shredded tobacco for Japan Tobacco brand name "Seven Star" just before rolling
A wt% ethanol solution was sprayed and added so that the amount of compound (2) to the shredded tobacco was 0.0001 wt%, and then rolled into paper. The smell and taste when smoked were compared using the two-point discrimination method. The evaluation by a specially trained expert panel of 20 people ranked 3rd.
It was as shown in the table.

[Table] From the above table, it can be seen that compound (2) has the effect of significantly improving the odor and taste of product tobacco. Example 4 A shredded and rolled-up product of sheet-shaped recycled tobacco produced in Example 2 using CMC (carboxymethyl cellulose) glue, which is a glue for shredding tobacco paper, mixed with this compound at a concentration of 0.001% by weight. The smoking taste of these products was compared using the two-point discrimination method using a control product made using a paste solution without the addition of Compound (2). The evaluation by a specially trained expert panel of 20 people was as shown in Table 4.

【represent.
* indicates a significant difference with a 5% risk rate.
As a result, it was found that compound (2) improves the aroma and taste of cigarettes even when added to glue for rolling adhesive, which is a material for cigarette manufacturing, and furthermore, the irritating odor caused by CMC is significantly suppressed. Example 5 Japan Tobacco brand name “Cheery” just before rolling
Add a 0.01 wt% ethanol solution of compound (3) to 50 g of shredded tobacco.
After adding it by spraying so that the amount of compound (3) was 0.0001% by weight, it was rolled into paper and the above-mentioned rolled tobacco without compound (3) was used as a control product. compared. The evaluations of 20 specially trained expert panels were as shown in Table 5.

[Table] From the above table, it can be seen that compound (3) has the effect of significantly improving the odor and taste of product cigarettes. Example 6 Compound (4) was added to 50 g of shredded tobacco for Japan Tobacco brand name “Seven Star” just before rolling.
A 0.001% by weight ethanol solution was sprayed and added so that the amount of compound (4) was 0.0001% by weight relative to the shredded tobacco, and the paper was rolled. The smell and taste when smoked were compared using the two-point discrimination method. The evaluations by a specially trained panel of 20 experts are as shown in Table 1.

[Table] From the above table, it can be seen that compound (4) has the effect of significantly improving the odor and taste of product cigarettes. (Effect of the invention) As is clear from the above examples, compounds (1) to
(4) is very useful as a tobacco flavor improver.

Claims (1)

[Claims] 1. General formula [However, n is 9 or 10, and R is [Formula] or [Formula]] A tobacco flavor improver comprising coenzyme Q (R=) or its reduced form (R=) represented by the following formula.