JPS5933582B2 - Oxidol acetate and tobacco flavor improver - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound occidole acetate 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 novel 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. It is.

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 solavetibone, 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. The present inventors succeeded in isolating a new compound, occidole acetate, from the leaves of the Rustica plant, and also discovered that this compound is extremely effective as a tobacco flavor improver, leading to the present invention. That is, the present invention is a compound occidole acetate (hereinafter referred to as the present compound) represented by the formula (J) and a flavor improver for tobacco 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. It can be isolated by performing preparative gas chromatography on the fraction eluted with a hexane-ether system of 95:5 (volume ratio) using hexane-ether.

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, that is, 400 ~
A so-called smear inoculation method may be used, in which 600 mesh of carborundum is sprinkled on the surface and a plant virus (concentration 0.75 μg/d) suspended in water or 0.1M phosphate buffer is applied while making a wound. Six days after inoculation with the plant virus, leaves with most of the lesions having a diameter of about 1171 mm or more are collected. The collected leaves 800f are freeze-dried using a vacuum freeze dryer to obtain a freeze-dried product 1107. (The lyophilized product is extracted 3 times with dichloromethane No. 31, and the extracts are combined and concentrated under reduced pressure to obtain a crude extract concentrate of 6.4 y. 300 ml of ether extract was obtained by steam distillation and ether extraction, and the ether extract was concentrated in the same manner as above to obtain 890 ml of steam distilled ether extract concentrate. Using silicic acid 151, this concentrate was diluted with hexane-ether. Column fractionation was performed using the system, and hexane ether = 95:
The fraction eluted at 5 (volume ratio) is concentrated in the same manner as above. From this concentrate, by performing preparative gas chromatography using a 10% FFAP (free fat acid polyester) column, a total of about 10 η of this compound can be obtained as a colorless oily substance. (Yield: approximately 0.09 per 1f of dry leaves). This compound was identified as occidole acetate based on the spectral data shown below.

Mass spectrometry spectrum (70eV): m/z (%) 44 (
42), 128 (16), 132 (21), 143 (1
7), 157 (100), 158 (16), 185 (5
3), 200 (38), 260 (M+, 0) Infrared absorption spectrum (liquid film): Cm-11740, 1600, 1
450, 1390, 1250, 800 nuclear magnetic resonance spectrum (CDCI3): δ (Ppm) 1.55 (6H-s
), 2.01 (3H-s), 2.

20 (6H-s), 6.92 (2H-s) This compound is also a compound known as occidol (Britain of the Agricultural Chemicals Japan magazine 1959
23, p. 143).

That is, in an ether solution of occidol (17), 1
．． When one volume of isopropenyl acetate and a catalytic amount of boron fluoride were added and stirred overnight at room temperature, this compound was reduced to about 800η.
can get.

This reaction can be expressed using a chemical structural formula as follows. This compound is a substance that has a light woody aroma accompanied by a refreshing feeling, and has desirable suitability as a tobacco aroma improver.

That is, when this compound was added to various tobacco raw materials that lacked aroma and taste and were irritating, and an evaluation test was conducted on the aroma and taste of these materials, it was found that this compound harmonized well with the original tobacco aroma, gave roundness to the aroma, Emphasizes the tobacco-like character,
It has been found that it has many excellent effects, including suppressing irritation and 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 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 they have been made into products, the aroma and smell of these products can be significantly improved. can.

The amount of this compound added may be extremely small, and is 0.00001 to 0.01% by weight based on tobacco or tobacco manufacturing materials.
Desirably, a sufficient effect can be obtained by adding 0.0001 to 0.001% by weight, which is economically advantageous.

Example 1 A 0.01% by weight ethanol solution of the present compound isolated by the method described above was added to shredded tobacco 507 for Japan Monopoly Corporation's product name "Cheriichi" just before rolling, until the amount of the present compound relative to the shredded tobacco was The compound was added by spraying to a concentration of 0,0001% by weight, then rolled into paper, and the above-mentioned rolled tobacco without the addition of this compound was used as a control product, and the odor and aroma when smoked were compared using a two-point discrimination method. .

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 flavor 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 the above-mentioned water-soluble portion was added back to the thin paper to make a sheet-shaped recycled tobacco 607. This compound isolated by the method described above was added in the same manner as in Example 1, and the amount added was 0. After adding the tobacco to a concentration of 0.0005% by weight, it was 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
A shredded rolled-up product of the sheet-shaped recycled tobacco produced in Example 2 was made using the mixture such that
These flaws were compared using the two-point discrimination method.

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) Quadratic formula (
A tobacco flavor improver comprising a compound represented by I). ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I)