JPS606191B2 - Flavor improver for tobacco - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a tobacco flavor and flavor improving agent comprising a compound effective in improving the flavor and flavor of tobacco.

In recent years, tobacco chewing preferences have shown a tendency to diversify, and in particular, preference is shifting towards products with a lighter taste and richer aroma.

In line with this, the raw leaf tobacco used in product cigarettes has come to be increasingly used as a mild tobacco with a light taste and low nicotine and tar content. In addition, some recycled tobacco manufactured by removing nicotine and synthetic tobacco made from plants other than leaf tobacco or various inorganic and organic ingredients are used to reduce the nicotine and alcohol content of tobacco products. It is starting to be used. However, when such tobacco raw materials are used for smoking, they generally lack aroma, are irritating, and lack flavor, so it is necessary to add some kind of substance to improve their sonic and smoking taste. From this point of view, it is an object of the present invention to provide a compound that improves the aroma and taste of leaf tobacco, which has a particularly poor aroma, is irritating, and lacks umami.

A large number of compounds are known to be effective in improving the aroma and taste of tobacco, and many of them are constituents of leaf tobacco.

The present inventors have conducted intensive research based on the prediction that compounds related to the components in leaf tobacco would be effective in improving the aroma and taste of tobacco. ) from among the compounds 5,6,7,8-tetrahydro-1-umbr-dimethyl-7-(1-methylethenyl)-2(neH)naphthalenone (common name: 1,2-dehydro-Q-siberone, hereinafter referred to as "this compound"). ) and found that this compound is extremely effective as a tobacco flavor improver, leading to the present invention. That is, the present invention is a tobacco flavor improver comprising the compound 1,2-dehydro-Q-siberone represented by the following formula.

This compound is the first compound isolated from nature by the present inventors, but its synthesis method is known (Canadian Journal Op.

(See Chemistry Magazine, 1967, 45, p. 1591).
However, 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 extracting dried goji fruit (wolfberry) with dichloromethane, then steam distilling the extract, obtaining the volatile neutral part by a conventional method, and subjecting the volatile neutral part to silica gel column chromatography. It can then be isolated by preparative gas chromatography.

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

That is, pulverized red-dried wolfberry (moisture 5).
5% by weight) was concentrated and extracted with 2.6k9 dichloromethane at room temperature for 2 hours, and the extract was filtered in a furnace and then extracted under reduced pressure (
20 side Hg) Concentrate at 4000 or less.

Dichloromethane is recovered and the same operation is repeated using the recovered dichloromethane. The total amount of extract at this stage was 1,632 mm, and the yield was 12.2% (hereinafter, percentages in this specification indicate weight % unless otherwise specified). The above concentrate was subjected to steam distillation, and 15 evenings of distillate were obtained per 100 evenings of concentrated liquid (distillation rate 1.9 evenings/hr).
). The distillate is saturated with common salt, extracted three times with ethyl, and the ether solution is washed with 1N aqueous hydrochloric acid and then with water. Next, it is washed with a 1N aqueous sodium hydroxide solution, washed with water, dehydrated over anhydrous sodium sulfate, and concentrated under reduced pressure at 40 qo or less (20 skin Hg). Through the above operations, 7.04% of volatile neutral parts were finally obtained (yield: 0.052%).
). This volatile neutral part was subjected to column chromatography using 250% silicic acid (manufactured by Mallinckrodt Co., USA) as a packing material and gradually increasing the polarity using a mixed solvent of hexane and ether (the column diameter was 5 mm). ).

First pass 1 hexane, then hexane; ether (9
8:2V/V) (The same applies to the following mixing ratios) Mixed liquid 1
Evening, 1 evening of the same 95:5 mixed solution, 1 of the same 90:1 good solution, 8 of the same
0:2 kelp liquid, 50:5 tail liquid, and ether are passed through in order, and separated one by one.

Since this compound exists in the hexane:ether (90; 10) mixture elution fraction mentioned above, in order to obtain it pure, this fraction was concentrated, and first, a magnetic liquid phase (5% FFAP, Nippon Chromato Preparative gas chromatography was performed using a column manufactured by Co., Ltd.), and then a nonpolar liquid phase (OV-1
01, manufactured by the same company), the same operation was performed to obtain the present compound as a colorless oily pure product with a weight of 0.8. This compound is 5.6.718 from the spectrum data shown below.
- Tetrahydro 11 - Dimethyl - 7 - ( 1 - methyl ethenyl ) - 2 ( Umbrella H ) It is identified as naphthalenone .

Mass spectrometry spectrum (7 degrees V): m/z (%) 216 (
M+, 4), 201 (24), 188 (7), 173 (
36), 159 (28), 145 (40), 105 (8
0) "91 (100), 79 (50), 77 (33)
, 67(51), 65(45).

Infrared absorption spectrum (liquid film): Enemy-116 spots, 162
91603 880 829. Nuclear magnetic resonance spectrum (
CDC13): 66.76 (IH, d, J = 10HZ)
, 6.23 (IH, d, J=10HZ), 4.81 (ga, m), 1.92 (ban, s), 1.80 (pan' s),
1.25 (thin, s).

Ultraviolet absorption spectrum (MeOH): n (log)
238 (3.66), 264 (Sh, 3.53).

This compound is a colorless oily substance with a dull grass-like odor, 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 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 and imparted tobacco flavor. At the same time, it has been found to have many excellent effects, including increasing the volume of smoke and reducing irritation, and these effects are long-lasting.

There are no particular restrictions on the timing or means of adding this compound to tobacco raw materials, and it can be added to shredded tobacco after being dissolved in an organic solvent such as ethanol, just like other commonly used flavorings. It can also be used to improve flavor and aroma by incorporating it into other materials for cigarette manufacturing, such as wrapping paper, glue, or filters.

Furthermore, there are no particular restrictions on the types of tobacco to which this compound can be applied, including cigarettes, pipe tobacco, and cigar tobacco made from regular leaf tobacco, recycled tobacco made from shoulder tobacco, and natural tobacco. By adding this compound to synthetic cigarettes, etc. manufactured using fibers or plant tissue cultures during the manufacturing process or after they have been commercialized, the aroma and taste of these products can be significantly improved. . The amount of this compound added may be as little as 0.00001% based on the tobacco or tobacco manufacturing materials.
~0.01% preferably 0.0001% ~ 0.001%
Since a sufficient effect can be obtained by adding , there is a great economic advantage.

Example 1 50 shredded tobacco for product name "Cherry" just before rolling
0.01 of the present compound isolated by the method described above.
% ethanol solution was exposed so that the amount of this compound to shredded tobacco was 0.0001% and rolled up into paper, and a rolled piece of shredded shredded tobacco without the addition of this compound was used as a control product, and when these were smoked. Odor and taste were compared using the two-point discrimination method.

The evaluations of 20 specially trained expert panels were as shown in Table 1. Table 1 * indicates that there is a significant difference at a risk rate of 5%.

The numbers in the table indicate the number of people who evaluated it as good.

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 100 qo of hot water, 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 coniferous kraft valve was added to it. The added mixture was formed into a thin paper, and the above-mentioned water port part was added back to the thin paper to make a sheet-shaped regenerated tobacco 6M, and the present compound isolated by the above method was added in the same manner as in Example 1. After adjusting the amount to 0.005%, cut it and roll it up.
The smoking taste was compared using a two-point discrimination method using a shredded and rolled-up product of the above sheet-shaped recycled tobacco to which the present compound was not added as a control product.

The evaluation by a specially trained expert panel of 20 people was as shown in Table 2. Table 2 * indicates that there is a significant difference at a risk rate of 5%.

, The numbers in the table indicate the number of people who rated it as good.

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. (Carboxymethylcellulose) A size solution containing 0.002% of this compound was used to make cut and rolled up products of the sheet-shaped recycled tobacco produced in Example 2, and a size solution without the addition of this compound was prepared separately. The smoking taste of these products was compared using a two-point discrimination method using a rolled product using the same method as a control product.

The evaluation by a specially trained expert panel of 20 people was as shown in Table 3. Table 3 * indicates that there is a significant difference at a risk rate of 5%.

The numbers in the table indicate the number of people who evaluated it as good.

As a result, this compound improves the aroma and taste of cigarettes even when added to the glue for wrapping adhesive, which is a material for cigarette manufacturing, and also improves the aroma and taste of cigarettes. M. C. Based on this, it was found that the irritating odor was significantly suppressed.

Claims (1)

[Scope of Claims] A tobacco flavor improver comprising the compound 1,2-dehydro-α-cyperone represented by the following formula: ▲Contains mathematical formulas, chemical formulas, tables, etc.▼