JPS61225193A - 13-hydroxysolanoscone-beta-glucoside and fragrant and flavorous improver for tobacco comprising same - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formula (R is Glc-O-). USE:A fragrant and flavorous improver for tobacco, improving fragrance and flavor of reprocessed tobacco which lacks fragrance and flavor, and has irritation, and keeping fragrance and flavor. PREPARATION:For example, yellow cigars are extracted with methanol at room temperature, the extract is dissolved in water, washed with n-hexane, and a hexane-soluble part is removed. Then, the resultant substance is extracted with n-butanol, the prepared component is adsorbed on a resin, liberated saccharides are washed with water and removed, a glycoside mixture is eluted with ethanol. The eluate is fractionated by the use of a silica gel column, and separated by high performance liquid chromatography, to give a compound shown by the formula.

Description

DETAILED DESCRIPTION OF THE INVENTION (Industrial Field of Application) The present invention relates to 13-hydroxytaranascone-β-glucoside and a tobacco flavor improver comprising the compound.

In recent years, tobacco preferences have shown a tendency to diversify, and products that are light and yet have a rich aroma and taste have become preferred. Therefore, the raw tobacco leaf used in product tobacco products has come to be increasingly used as a mild tobacco product with a light taste and low nicotine and tar content. or,
So-called tobacco substitutes (hereinafter referred to as [Artificial Tobacco-1)] made of recycled tobacco manufactured by removing nicotine, plants other than leaf tobacco, or various inorganic and organic components, etc.
etc. are also coming into use. However, such tobacco raw materials generally have poor flavor and flavor, are often irritating, and lack flavor, so it is necessary to add some substance to improve the flavor and flavor.

(Problems to be Solved by the Invention) From this point of view, the present invention aims to improve the flavor and flavor of tobacco products manufactured from leaf tobacco, recycled tobacco, artificial tobacco, etc., which are particularly poor in flavor, have irritation, and lack flavor. The purpose is to provide a new compound that improves the

A large number of compounds have been known as substances that are effective in improving the aroma and taste of tobacco.

The present inventors believed that compounds originally contained in leaf tobacco would harmonize well with the original aroma and taste of tobacco, and isolated many essential oil components from leaf tobacco.
It has been successful in improving the flavor of tobacco. It is well known that these essential oil components in leaf tobacco play an important role in tobacco aroma, but some of the non-volatile components in leaf tobacco are also effective in improving the aroma and taste of tobacco through thermal decomposition during smoking. Based on the prediction that there may be components that produce such substances, intensive research has been conducted to isolate new compounds useful for such purposes from nonvolatile components in leaf tobacco. As a result, we have isolated a new compound from yellow leaf tobacco that has an excellent effect on improving the aroma and taste of tobacco, leading to the present invention.
2. The present invention provides a compound represented by the structural formula of the following formula (1), that is, 13-hytroxyclanascone-β-glucoside (hereinafter referred to as the present compound 1), and a tobacco flavor improver comprising the compound. This is the gist of the invention.

(In the formula, R represents G+c-0-) (Means for solving the problem) The present compound is produced by extracting yellow branch leaf tobacco with methanol, removing components soluble in hexane from the extract, and then extracting it with butanol. This was extracted with IHP-20 resin, and after free sugars were removed, it was eluted with ethanol. The present compound can be isolated by subjecting the solution to various chromatographic treatments described below.

(Example 1) Next, an example of a method for isolating this compound will be shown.

After drying to a moisture content of IO%, yellow seed leaf tobacco from Parginia in the United States, which was cut into 111111 pieces, was mixed with methanol and 3%.
The extract is extracted by immersion in 1Y4I for 48 hours at room temperature, and the extract is filtered and concentrated under reduced pressure. Next, this extract was dissolved in 4 parts of water, then washed with 4 parts of hexane to remove the hexane-soluble portion, and further extracted with 3 parts of n-butanol. After concentrating this extract, it was adsorbed on HP-20 resin, free sugars were eluted and removed with 10 parts of water, and the glycoside mixture was extracted with 4 g of ethanol. This is concentrated to obtain residue No. 13. This residue was fractionated using a silica gel column, and then subjected to high performance liquid chromatography (reverse phase (trade name: μ-Bondpa).
The spectral data of the present compound are shown below.

Mass spectrometry (FD-MS) 379 Optical rotation [CI) Tl = -1,7° (c = 0.
243: Et (JH) nuclear magnetic resonance spectrum "C-NMR δ' (pPm) 17.6 (CH+i), 18.4 (
CHs ), 23.1 (Cal, ), 26.5 (C
H2) , 34.2 (CH2) , 42.1 (CH)
.

43.1 (C112), 44.5 (CH), 45.
9(C), 47.2(CH,,)49°2(CH),
50.1 (C), 50.7 (C), 62.5 (CH2)
.

71.2(CI(),, 75.8(CH), 78.
2 (CH), 78.6 (CH).

89.2 (CH,), 105.4 (CH), 2
12.6 (C=0) Next, this compound 5
, 1,21,20 U/W protein) to obtain 1.5 μg of agricon 13-hydroxysolanascone represented by the following formula (It).

(It) The spectral data of the compound aglycone is shown below.

Mass spectrometry (EI-MS) 234 Nuclear magnetic resonance spectrum 'II-NMR δ: (ppm) 1.02 (3H, s), 1.14 (
IH,,d,J=10Hz),1.25(3H,s
), 1.35(Ill,m), 1.50(3
H, m) 1.70 (IH, s ), 1.92 (IH
, t, J-'11Hz), 2.10(IH, d
, J=l 01lz) , 2.12(, IH,d ,
d, J=5.12Hz), 2.26(IH, d
, J = 5.5Hz), 2.51 (IH, m)
, 2.52 (IH, m).

2.55 (1,1-1,d,d,J=5.111]z)
, 3.76 (2H, s) This compound is a white solid with no aroma by itself, but has desirable suitability as a tobacco flavor improver. In other words, it lacks aromatic flavor,
When this compound was added to various irritating tobacco raw materials 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 a rounded aroma and emphasizing the tobacco-like taste. It has been found that it has many excellent effects, including suppressing irritation and long-lasting effects.

The timing and method of adding this compound to tobacco raw materials are not limited to orange, and it can be used by adding it to shredded tobacco after dissolving it in an organic solvent such as ethanol, just like other commonly used flavorings. The effect of improving flavor and aroma can also be achieved by incorporating it into other cigarettes, manufacturing materials such as wrapping paper, glue, filters, etc. There are also no particular restrictions on the types of vine tobacco to which this compound is 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 tobacco, etc. manufactured using fibers or plant cultures during the manufacturing process or after the product has been manufactured, the aroma and taste of these products can be significantly improved. .

The amount of this compound added may be extremely small, and sufficient effects can be obtained by adding 0.0001% to 0.1%, preferably 0.001% to 0.01%, to the tobacco or tobacco manufacturing materials. There is also a great economic advantage.

(Example 2) A 0.1% ethanol solution of the present compound synthesized by the method described above was added to 50 g of shredded tobacco for Japan Monopoly Corporation's product name "Peace" just before rolling. The smoked tobacco was sprayed to a concentration of 0,001% and rolled into paper, and the above tobacco roll without the addition of this compound was used as a control product, and the inclination and taste when smoked were compared using a two-point discrimination method. . Specially trained expert panel 2
The evaluation by 0 people was as shown in Table 1.

Table 1 The numbers in the table indicate the number of people who evaluated it as good.

* indicates a significant difference at a risk rate of 5%.

From the above table, it can be seen that this compound has the effect of significantly improving the aroma and taste of product cigarettes.

(Example 3) Waste tobacco is extracted with hot water at 100°C and separated into a water-soluble part and a water-insoluble part, and then the water-insoluble part is beaten, and a coniferous kraft bulb of 15% of its dry weight is added to the water-insoluble part. The mixture to which the above-described water-soluble portion was added was molded into a thin paper, and the above-mentioned water-soluble portion was added back to the thin paper, and 60 g of shredded recycled tobacco sheet was treated with the compound isolated by the method described above in the same manner as in Example 1. The smoke 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 the present compound as a control product.

The evaluation by a specially trained expert panel of 20 people was as shown in Table 2.

Table 2 The numbers in the table indicate the number of people who evaluated it as good.

* indicates that there is a significant difference at a risk rate of 5%.

As a result, it can be seen that the aroma and taste of the 17 vegetables to which the present compound was added were significantly improved, and the effect of suppressing irritation was also remarkable.

(Example 4) Sheet-shaped recycled material manufactured in Example 2 using carboxymethyl cellulose (hereinafter abbreviated as CMC) paste, which is a paste for paper wrapping made from shredded tobacco, mixed with this compound at a concentration of 0.02%. Cut and rolled tobacco products were made, and the smoking taste of these products was compared using a two-point discrimination method using separately rolled products using a paste 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 3 The numbers in the table indicate the number of people who evaluated it as good.

* indicates a significant difference at a risk rate of 5%.

As a result, it was found that the present compound improves the aroma and taste of cigarettes even when added to glue for winding adhesive, which is a material for cigarette manufacturing, and furthermore, the irritating odor of CMC is significantly suppressed.

(Effects of the Invention) When this compound was added to various tobacco raw materials that had a irritating aroma and taste, 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 had no effect on the aroma. It has been found that it has many excellent effects, such as giving it a rounder taste, emphasizing the tobacco-like taste, suppressing irritation, and that these effects are long-lasting.

Claims (1)

[Claims] 1. A compound represented by the following formula (1) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (1) (R in the formula represents G_1_c-O-) 2. A compound represented by the following formula (1) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(1) (In the formula, R: represents G_1_c-O-)