JPH05186397A - Glycerol derivative and flavor and taste improver for tobacco containing the same compound as active ingredient - Google Patents

Abstract

PURPOSE:To obtain the subject new compound, capable of readily imparting and enhancing excellent flavor and taste as a tobacco flavor and taste improver to tobacco simply by adding a small amount to shredded tobacco and useful for improving, etc., the flavor and taste of cigarettes directing to low nicotine and tar contents. CONSTITUTION:A compound expressed by the formula (R1 to R3 are acetyl or 8-20C terminal branched acyl, except that all the R1 to R3 are acetyl). This compound is preferably obtained by immersing a wild species tobacco plant such as Nicotiana benthamiana in an organic solvent such as chloroform or hexane, extracting the plant, then concentrating the resultant extract, successively subjecting the prepared resin fraction to silica gel chromatography and high- performance liquid chromatography, separating and purifying the fraction. When this compound expressed by the formula is used as a flavor and taste improver for tobacco, it is preferably added in an amount of 0.01-100ppm based on the weight of shredded tobacco.

Description

Detailed Description of the Invention

[0001]

TECHNICAL FIELD The present invention relates to a glycerol derivative and a tobacco flavor improving agent containing the compound as an active ingredient.

[0002]

2. Description of the Related Art In recent years, tobacco consumers have been
It is shifting to low nicotine and low tar cigarettes,
When these cigarettes are smoked, they tend to have a low flavor and a small amount of smoke, and have a drawback that the consumer cannot be sufficiently satisfied.

For this reason, it has been empirically attempted to compensate for this defect by adding sugars such as sugar and honey, but it is not effective unless a large amount of these sugars is used. A substance effective in is desired.

The present invention has been made in view of the above points, and an object of the present invention is to provide a compound capable of imparting or enhancing the flavor and smoke amount of tobacco in a trace amount.

[0005]

In order to solve the above-mentioned problems, the present inventor has conducted a wide search for effective compounds and is effective in imparting or enhancing flavor and smoke amount in wild-type tobacco extract. The present invention has been accomplished by discovering such a compound and further elucidating that the compound is a novel compound not described in the literature.

That is, the present invention provides a glycerol derivative represented by the following formula [1] (wherein R1, R2 and R3 are acetyl groups or branched acyl groups having 18 to 20 carbon atoms, and R1, R2 and R3 are all acetyl groups).

[0007]

[Chemical 3]

Furthermore, the present invention provides a glycerol derivative represented by the following formula [1] (wherein R1, R2 and R3 are acetyl groups or acyl groups having a branched chain of 18 to 20 carbon atoms and R1 and R2 The present invention provides a flavor and taste improving agent for tobacco, which comprises R2 and R3 (excluding cases where all are acetyl groups) as an active ingredient.

[0009]

[Chemical 4] $ This compound was found to be contained in the leaves, flowers, and stems of plants of the genus Nicotiana in the Solanaceae family, and in particular, was found to be contained in large amounts in wild-type tobacco plants such as Nicotiana benthamiana.

This compound was extracted by dipping Nicotiana plants in an organic solvent such as chloroform, hexane, ethyl acetate, acetone, methanol and the like, and then concentrating the extract to obtain a resin fraction, which was then subjected to silica gel chromatography, followed by high speed chromatography. It is obtained by sequential separation by liquid chromatography.

When this compound is used as a flavor and taste improving agent for tobacco, its addition amount is, for example, 0.01 ppm to 100 pp based on the weight of cut tobacco.
The range of m is preferable, but it should be increased or decreased according to the flavor and taste quality of the raw tobacco.

[0012]

The present invention will be described in more detail with reference to the following examples.

Example 1 An example of the method for producing the compound of the present invention will be described below.

Fresh leaves of Nicotiana benthamiana 10k
g is immersed in 50 liters of chloroform for about 3 minutes to extract the chloroform-soluble leaf surface resin component. The extract thus obtained is filtered with a filter paper, and the filtrate is concentrated under a rotary evaporator at 35 ° C. to obtain 60 g of a leaf surface resin.

The entire amount of the leaf surface resin is dissolved in a small amount of chloroform, and silica gel column chromatography is performed. A column (diameter 40 mm, height 300 mm) was packed with Wakogel C200 (manufactured by Wako Pure Chemical Industries, Ltd.), and chloroform, chloroform / acetone = 1/1, acetone, and methanol were sequentially eluted with 1 liter each, and 4 fractions were obtained. (27.6
g (fraction 1), 25.3 g (fraction 2), 3.3 g (fraction 3) and 3.7 g (fraction 4)) are obtained.

After concentrating fraction 1 in the above 4 fractions, 27
g is again subjected to silica gel column chromatography.
Wakogel C on a column (diameter 50 mm, height 120 mm)
300 (manufactured by Wako Pure Chemical Industries, Ltd.) was filled, and hexane / acetone = 9/1, hexane / acetone = 8/2, hexane / acetone = 7/3, and acetone were sequentially eluted with 300 ml of each, and further 4 strokes were drawn. Fractions (fractions 1-1 to 1-4) are obtained.

Fraction 1-1 of the above fractions is concentrated and subjected to high performance liquid chromatography under the following conditions to obtain 350 mg of lipid 1.

Column: Silica gel column type (YMC-made, YMC-PACK A014SIL) Solvent: Hexane / Ethyl acetate = 9/1 Flow rate: 1.5 ml / min

The retention time of the obtained lipid 1 is
It was 21 minutes.

The lipid 1 thus obtained was subjected to thin-layer chromatography (developing solvent: hexane / ethyl acetate = 7) using a normal-phase thin layer plate (Merck, Art 5642).
In / 3), one spot was shown, and its Rf value was 0.61.

The 1H-NMR spectrum, 13C-NMR spectrum, IR spectrum and GC-MS analysis result of the obtained lipid 1 after methanolysis were as follows. The GC-MS analysis after methanolysis was 5%.
Methylation was performed overnight (40 ° C.) with sulfuric acid-methanol, and hexane extraction was performed as a sample.

1 H-NMR (δ ppm, CDCl ₃ ):
5.27 (m, 1H), 4.22 (dddd, 4H) 13 C-NMR (δppm, CDCl ₃ ): 173.0 (CO), 1
70.5 (CO), 68.7, 62, 3 IR (cm ^-1 ): 1750 (C = O) GC-MS: 16-methylhexadecanoylmethyl ester (M + 298, 255, 199, 143, 74, 43), 18-methylhexadecanoyl methyl ester (M + 326, 283, 227, 199, 14
(3, 74, 43)

From these results, lipid 1 was identified as a triacylglycerol having an acyl group consisting of an acetyl group, a 16-methylheptadecanoyl group and an 18-methylnonadecanoyl group.

Example 2 Dissolved in ethanol so that the added amount of the lipid 1 isolated in Example 1 was 0.01 ppm and 100 ppm per unit weight of cut tobacco, respectively, and sprayed on the cut tobacco of cigarette leaf set. Was added uniformly. After this,
After leaving it at room temperature (25 ° C.) for 2 days to adapt it well to the cut tobacco, it was rolled up into a cigarette form to obtain a fragrance product.

A sensory test was conducted on the flavor and smoke amount of the obtained fragrance product by a two-point discrimination test method from a fragrance-free product to which no compound was added, by a panel of 20 people who specialize in taste and taste of cigarettes. .. The results are shown in Table 1 below.

Table 1 Classification Flavor Smoke amount Perfumed products Lipid 1 0.01 ppm 19 19 Lipid 1 100 ppm 19 19 * Number indicates the number of panel members who were considered better than unscented product.

As can be seen from Table 1 above, in the case of perfumed products, both the flavor and smoke amount increased at both addition amounts of 0.01 ppm and 100 ppm, and the excellent tobacco flavor and taste improvement were obtained. It was confirmed to have an effect.

[0028]

As described above, according to the compound of the present invention, by adding a small amount to the cut tobacco, it is possible to impart or enhance excellent flavor and smoke amount to tobacco, and low nicotine and low smoke. The present invention has an effect such that the flavor and taste quality of a cigarette oriented to tar can be easily improved.

Claims (2)

[Claims] 1. A glycerol derivative represented by the following formula [1]. (However, in the formula, R1, R2, and R3 are an acetyl group or an acyl group having a branched chain of 18 to 20 carbon atoms,
Except when 1, R2 and R3 are all acetyl groups) 2. A flavor and taste improving agent for tobacco, comprising a glycerol derivative represented by the following formula [1] as an active ingredient. (However, in the formula, R1, R2, and R3 are acetyl groups or 1 carbon atoms.
The terminal of 8 to 20 is a branched acyl group, and R1, R2,
Except when all R3 are acetyl groups)