JPS6136836B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to a lycithin glycoside and a tobacco flavor improver comprising the compound. In recent years, tobacco preferences have shown a tendency to diversify, and people have come to prefer lighter products with richer flavors. In line with this trend, the raw material leaf tobacco used in tobacco products has come to be increasingly used as a mild tobacco product with a light taste and low nicotine and tar content. In addition, recycled tobacco manufactured 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 ingredients have also come into use. There is. However, such tobacco raw materials generally have poor aroma and flavor, are often irritating, and lack flavor, so it is necessary to add some kind of substance to improve the aroma and flavor. From this viewpoint, the present invention aims to provide a parent compound that improves the aroma and taste of tobacco produced from leaf tobacco, recycled tobacco, artificial tobacco, etc., which are particularly poor in aroma and taste, are irritating, and lack flavor. This is the purpose. A number of compounds have been known to be effective in improving the aroma and taste of tobacco, but the present inventors have discovered that compounds that are naturally present in leaf tobacco harmonize well with the original aroma and taste of tobacco. Thinking that this might be the case, we have isolated many essential oil components from leaf tobacco and have achieved results in improving the aroma and taste of tobacco.
It is well known that these essential oil components in leaf tobacco play an important role in imparting tobacco aroma, but some of the non-volatile components in leaf tobacco are also thermally decomposed during smoking. Based on the prediction that there may be components that produce substances effective in improving smoking taste, intensive research has been conducted to isolate new compounds useful for this purpose from the nonvolatile components of leaf tobacco. As a result, we have isolated a novel compound from yellow seed tobacco that has an excellent effect on improving the aroma and taste of tobacco, and have completed the present invention. That is, the present invention provides a lycitin glycoside (hereinafter referred to as "the present compound") which is a compound represented by the structural formula of the following formula (). and a tobacco flavor improver comprising the compound. This compound is produced by extracting yellow seed leaf tobacco with methanol, sequentially removing hexane-soluble components from the extract, then removing chloroform-soluble components to obtain a water-soluble fraction, and converting the aqueous solution into ions. Pass through an exchange resin to remove the basic and acidic fractions to obtain the non-volatile neutral part. This can be isolated by extracting it with butanol and subjecting the solution to various chromatographies. Next, an example of a method for isolating this compound will be shown. That is, 3 kg of yellow seed leaf tobacco from Virginia, USA, which was dried to about 10% moisture and finely chopped to a width of 1 mm, was extracted by immersion in 31 kg of methanol at room temperature for 48 hours, and the extract was filtered and concentrated under reduced pressure. Next, add this extract to 4 ml of water.
The solution was washed with 4 kg of hexane and then with 2 kg of chloroform to remove the hexane and chloroform soluble parts. The water-soluble fraction thus separated was transferred to ion exchange resin columns (Dowex CCR-2 (H ⁺ ) and Amberlite).
Pass through IR-45 (OH ^- )) to remove bases and acids;
The resulting neutral aqueous solution was extracted with 3 kg of n-butanol. The resulting n-butanol soluble portion was concentrated to volatilize the n-butanol, then dissolved in 200 ml of water, adsorbed on a charcoal column, eluted with methanol, and concentrated to obtain a residue. This is fractionated using a silica gel column and further separated by high performance liquid chromatography (reverse phase, 50% methanol) to obtain the present compound as a white solid. The spectral data of this compound is shown below. Optical rotation [α] _D = -34.43 (C = 0.115 EtOH) Mass spectrometry spectrum (FD-MS) M/Z569 (M + Na) ⁺ nuclear magnetic resonance spectrum ( ¹ H-NMR) δ: (ppm) 1.53 (3H, d , J = 6.8Hz) 1.72 (3H,
s) 3.66 (1H, t, J=8.5Hz) 3.8~4.6
(13H, m) 5.03 (1H, d, J = 7.1Hz) 5.37 (1H,
d, J = 6.6 Hz) This compound is a white solid with no aroma by itself, but 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 aroma and taste of tobacco, giving it a rounded aroma. , emphasizes the tobacco-like character, suppresses irritation,
Furthermore, it has been found that these effects are long-lasting and have many other excellent effects. 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 the flavor and aroma of cigarettes, and can also be incorporated into cigarettes, manufacturing materials 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 manufactured using fibers or tissue cultures of plants during the manufacturing process or after they are manufactured, the flavor and taste of these products can be significantly improved. can. The amount of this compound added may be extremely small, and is 0.0001% to 0.1% based on tobacco or tobacco manufacturing materials.
%, preferably 0.001 to 0.01%, can provide a sufficient effect, which is economically advantageous.
In addition, all percentages described in this specification indicate weight percentages. Example 1 Japan Monopoly Corporation product name “Peace” just before winding
A 0.1% ethanol solution of the present compound synthesized by the method described above is sprayed onto 50 g of shredded tobacco, so that the amount of the present compound is 0.001% relative to 50 g of shredded tobacco, and rolled into paper. Using a shredded rolled product as a control product, the aroma and taste when smoked were compared using the two-point discrimination method.
The evaluations of 20 specially trained expert panels were as shown in Table 1.

[Table] Indicates that there is.
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 hot water at 100°C, separated into a water-soluble part and a water-insoluble part, and the water-insoluble part was beaten.
A mixture of this and 15% of the dry weight of softwood kraft pulp was molded into thin paper, and 60g of sheet-shaped recycled tobacco was made by returning the water-soluble portion to this thin paper and isolated using the method described above. The obtained compound was rolled up in the same manner as in Example 1, and the taste was compared using a two-point discrimination method using the above-mentioned shredded and rolled-up sheet-shaped recycled tobacco without the addition of the compound as a control product. The evaluation by a specially trained expert panel of 20 people was as shown in Table 2.

[Table] Indicates that there is.
The numbers in the table indicate the number of people who evaluated it as good. The results show that products to which this compound is added have markedly improved aroma and taste, and also have a remarkable effect of suppressing irritation. Example 3 Using a carboxymethyl cellulose (CMC) paste, which is a paste for paper wrapping of shredded tobacco, mixed with this compound at a concentration of 0.02%, the shredded and rolled-up product of the sheet-shaped recycled tobacco produced in Example 2 was produced. Making,
Separately, the smoking taste of these products was compared using a two-point discrimination method using a rolled product made using a glue liquid without the addition of the present compound as a control product. The evaluation by a specially trained expert panel of 20 people was as shown in Table 3.

[Table] Indicates that there is.
The numbers in the table indicate the number of people who evaluated it as good. As a result, it was found that this compound improves the aroma and taste of cigarettes even when added to glue for wrapping adhesive, which is a cigarette manufacturing material, and furthermore, the irritating odor of CMC is significantly suppressed.

Claims (1)

[Claims] A compound represented by the following formula: (In the formula, R represents Glc-(l→2)-Glc-) A tobacco flavor improver comprising a compound represented by the following formula: (In the formula, R represents Glc-(l→2)-Glc-)