JPS5932451B2 - Oxidol Isomer 1 and tobacco flavor improver - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound oxidol isomer 1 and a tobacco flavor improver comprising the compound.

In recent years, tobacco preferences have shown a tendency to diversify, and in particular, preferences are shifting towards products with a lighter taste and richer 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, recycled tobacco produced by removing nicotine, so-called artificial cigarettes (hereinafter referred to as "artificial cigarettes") made from 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. From this point of view, it is an object of the present invention to provide a new compound that improves the aroma and taste of tobacco made from leaf tobacco, recycled tobacco, artificial tobacco, etc., which have poor aroma, irritation, and lack of flavor. .

A large number of compounds have been known as substances that are effective in improving the aroma and taste of tobacco, and sesquiterpenoids originally contained in leaf tobacco, such as solavetibon, solanascone, and huyuberol, are one such group of compounds.

The present inventors have conducted extensive research to isolate sesquiterpenoids based on the prediction that sesquiterpenoid compounds would be effective as they harmonize well with the aroma of tobacco, and found that Nicotiana spp. Novel compound occidol isomer 1 from the leaves of the Rustica plant
The present inventors succeeded in isolating the compound and found that it is extremely effective as a tobacco flavor improver, leading to the present invention. That is, the present invention is a compound represented by formula (I), oxidol isomer 1 (hereinafter referred to as the present compound), and a tobacco flavor improver comprising the compound. This compound was the first compound isolated from nature by the present inventors, and its synthesis method was unknown until now.

Therefore, until now, it has not been known at all that this compound exhibits excellent effects as a tobacco flavor improver. This compound is produced by inoculating the leaves of a growing Nicotiana rustica plant with a plant virus, collecting the leaves after a certain period of time, extracting the leaves with an organic solvent, performing steam distillation, and distilling the steam distillate into a silicate column. Fractionate with hexane-ether system using
It can be isolated by performing preparative gas chromatography on the fraction eluted at a volume ratio).

Next, an example of a method for isolating this compound will be shown.

Fifty Nicotiana rustica plants are grown for about two months in a field or in a greenhouse using conventional tobacco cultivation methods, and then all leaves are inoculated with tobacco mosaic virus. The method of inoculation is the usual method, i.e. 400 ml on the whole/leaf surface.
The so-called smear inoculation method may be used, which involves sprinkling ~600 bushes of carborundum and applying it to a plant virus suspended in water or 0.1M phosphate buffer (concentration 0.75 μ7/MO) while making a wound.

On the 6th day after inoculation with the plant virus, most of the lesions were approximately 1 m in diameter.
Collect leaves that have reached T1 or higher. Freeze-dry the collected leaves 8007 using a vacuum freeze dryer to obtain freeze-dried product 1.
Get 10 points. The lyophilized product is 31 dichloromethane and 3
The extraction is repeated twice, and the extracts are combined and concentrated under reduced pressure to obtain 6.4 units of crude extract concentrate. The crude extract concentrate is subjected to steam distillation and ether extraction using a steam distillation continuous extractor to obtain 300 ml of ether extract, and the ether extract is concentrated in the same manner as described above to obtain 890 ml of steam distilled ether extract concentrate. This concentrate is subjected to column fractionation using a hexane-ether system using 15 grams of silicic acid, and the fraction eluted with hexane ether=80:20 (volume ratio) is concentrated in the same manner as described above. From this concentrate, F
By performing preparative gas chromatography using a 10% FAP (free fat acid polyester) column, approximately 5η of the present compound can be obtained as white crystals in a retention time of 10 minutes. (Yield: approximately 0.05 η per dry leaf). This compound was identified as occidol isomer 1.1 based on the spectral data shown below.

Mass spectrometry spectrum (70eV): m/z (%) 59 (
53), 119 (26), 145 (21), 157 (1
00), 159 (23), 185 (37), 200 (2
6), 218 (M+, 5) Infrared absorption spectrum: CTIl-1 3450, 1605, 1460, 1385, Nuclear magnetic resonance spectrum (CDCl3): δ (Ppm) proton 1
．． 28 (6H.Σ), 2.20 (6H.s), 6.90
(2H,.S) Carbon 14.9 (↓), 20.4 (t), 24.0 (V), 2
6.6 (J), 27.3 (le), 28.9 (y), 30
．． 7 (t), 46.3 (su), 72.7 (foot), 125
．． 9(d), 127.1(d), 133.5(s), 1
34.2(s), 134.9(s), This compound is a substance that has a light woody aroma accompanied by a refreshing feeling, and has desirable suitability as a tobacco flavor improver.

In other words, when this compound was added to various tobacco raw materials that lacked aroma and were irritating, and an evaluation test was conducted on the aroma of these materials, it was found that this compound harmonized well with the original tobacco aroma and was completely immersed in the aroma. It has been found that it has many excellent effects, such as enhancing tobacco flavor, emphasizing the tobacco-like taste, suppressing irritation, and having long-lasting effects.

The timing and means of adding this compound to tobacco raw materials are not particularly limited, and it can be used by dissolving it in an organic solvent such as ethanol and adding it to shredded tobacco like other commonly used flavorings, or by adding it to shredded tobacco. The effect of improving flavor and aroma can also be achieved by incorporating it into materials for manufacturing cigarettes, such as wrapping paper, glue, filters, etc.

Furthermore, there are no particular restrictions on the types of tobacco to which this compound can be applied, including cigarettes, pipe tobacco, cigar tobacco, etc. made from regular leaf tobacco, recycled tobacco made from scrap tobacco, and natural tobacco. By adding this compound to synthetic cigarettes, etc. manufactured using fibers or tissue cultures of plants during the manufacturing process or after the product is manufactured, the aroma and taste of these products can be significantly improved. .

The amount of this compound 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. Therefore, there is a great economic advantage.

Example 1 A 0.01 wt % ethanol solution of the present compound isolated by the above method was added to 50 y of shredded tobacco of Japan Monopoly Corporation's brand name "For Thierry" just before rolling, until the amount of the present compound relative to the shredded tobacco was 0. After adding the compound by spraying it to a concentration of .0001% by weight, it was rolled up into paper, and the odor and taste when smoked were compared using a two-point discrimination method using the roll of the above-mentioned shredded tobacco without the addition of this compound as a control product.

The evaluations of 20 specially trained expert panels were as shown in Table 1. From the above table, it can be seen that this compound has the effect of significantly improving the aroma and taste of product tobacco. 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 15% of the dry weight of softwood kraft pulp was added thereto. The mixture was molded into a thin paper, and the above-mentioned water-soluble portion was added back to the thin paper to make 60 sheets of recycled tobacco.The compound isolated by the method described above was added in the same manner as in Example 1, and the amount of addition was adjusted. It was added by spraying to a concentration of 0.0005% by weight, then shredded and rolled up, and the taste was compared using a two-point discrimination method using a shredded and rolled-up product of the above-mentioned sheet-shaped recycled tobacco without the addition of this compound as a control product.

The evaluation by a specially trained expert panel of 20 people was as shown in Table 2. As a result, it was found that the products to which this compound was added had a marked improvement in aroma and taste, and also had a remarkable effect of suppressing irritation.

Example 3 C. M. C. (Carboxymethyl cellulose) 0.001% by weight of this compound in the paste liquid
Cut and rolled products of the sheet-shaped recycled tobacco manufactured in Example 2 were made using the mixture such that We compared the tastes of these.

The evaluation by a specially trained expert panel of 20 people was as shown in Table 3. As a result, this compound improves the aroma and taste of cigarettes even when added to glue for rolling adhesive, which is a material for cigarette manufacturing, and also improves the aroma and taste of cigarettes. M. C. It was found that the irritating odor caused by

Claims (1)

[Claims] A compound represented by the primary formula (I)▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) A compound represented by the secondary formula (I)
A tobacco flavor improver consisting of the compound represented by I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I)