JPS5831915B2 - Flavor improver for tobacco - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a tobacco flavor improver comprising occidenchlor.

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 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.

Conventionally, many compounds have been known as substances effective in improving the aroma and taste of tobacco, and sesquiterpenoids originally contained in single-leaf tobacco, such as solavetibone, solanascone, and huituverol, are one of these compounds.

The present inventors predicted that a sesquiterpenoid compound would be effective as it would harmonize well with the aroma of tobacco.

As a result of intensive research aimed at isolating sesquiterpenoids, we succeeded in isolating occidentalol from the leaves of Nicotiana rustica plants inoculated with plant viruses, and found that this compound is extremely useful as a tobacco flavor improver. The present inventors have found that this is effective and have come up with the present invention.

That is, the present invention is a tobacco flavor improver comprising the compound occidentalol (hereinafter referred to as the present compound) represented by formula (I).

This compound is already a known compound, and has been described as an essential oil component of Hibarium nigra, which belongs to the Cupressaceae family.

(Bulletin of the Agricultural Chemicals of Japan, 1956, Vol. 20, p. 215).

However, until now, there has been no knowledge of its use as an excellent 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 converting the steam distillate to silicic acid. It can be isolated by fractionating with a hexane-ether system using a column and performing preparative gas chromatography on the fraction eluted with hexane:ether 80:20 (volume ratio).

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 ml of
The so-called bed inoculation method involves sprinkling ~500 mesh of carborundum and applying a plant virus suspended in water or 0.1 MIJ acid buffer (acidity 0.75μ'/TILl) under sunlight. good.

Six days after inoculation with the plant virus, most of the lesions were approximately 1 in diameter.
Collect leaves that have reached rnm or higher.

80 oz of collected leaves were freeze-dried using a vacuum freeze dryer to produce a freeze-dried product of 110 oz. get.

The freeze-dried product was extracted three times with 3 tons of dichloromethane, and the extracts were combined and concentrated under reduced pressure to obtain a crude extract concentrate 64y'.

The crude extract concentrate is subjected to steam distillation and ether extraction using a steam distillation continuous extractor to obtain 300 TrLl of ether extract, and the ether eluate is concentrated in the same manner as above to obtain steam distilled ether extract concentrate 8907n9.

This concentrate was subjected to column fractionation in a hexane-ether system using 15P silicic acid, and hexane:ether-8
The fraction eluted at 0:20 (volume ratio) is concentrated in the same manner as above.

From this concentrate, preparative gas chromatography is performed using a 1 m column of 10% F'F'AP (free fat acid polyester) at a temperature increase of 10 °C/step from 100 °C to 240 °C. By this, approximately 10 m9 of the present compound can be obtained as white crystals within a holding time of 9 minutes.

(Yield: about 0.09 square meters per 1z of dry leaves) This compound shows the following spectrum.

Mass spectrometry spectrum (70eV): m/z (%
) 44 (49), 59 (52), 105 (48).

119 (47), 131 (100), 145 (46),
159(48), 187(25).

202 (18), 220 (M, 17) Infrared absorption spectrum (liquid film): C1rL'3.450, 1,590
．． 845.720 nuclear magnetic resonance spectrum (CDCI3)
: δ (ppIII) 0.90 (3H-s) jl, 22 (
6H-s).

1.72 (3H-s), 5.55-5.84
(3H-m) This compound is a substance having a woody aroma accompanied by a camphor aroma, and has desirable suitability as a tobacco flavor improver.

In other words, when this compound was added to various tobacco raw materials that had a irritating aroma and flavor, 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 gave a rounded flavor to the aroma. , emphasizes the tobacco-like character,
It has been found that it has many excellent effects, including suppressing stinging and having 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 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 materials for manufacturing cigarettes, such as wrapping paper, glue, filters, etc.

In addition, there are no particular restrictions on the types of vine tobacco to which this compound can be applied.In addition to cigarettes, pipe tobacco, cigar tobacco, etc. made from regular leaf tobacco, recycled tobacco made from scrap tobacco, natural tobacco, etc. By adding this compound to synthetic cigarettes, etc. manufactured using fibers or tissue cultures of plants during the manufacturing process or after the product is manufactured, the aroma and taste of these products can be significantly improved. .

The amount of this compound added may be extremely small, and is 0.00001-0.01% 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 applied to shredded tobacco 502 for Japan Monopoly Corporation's brand name "Cherry" just before rolling, until the amount of the present compound relative to the shredded tobacco was 0. After spraying and adding the compound to a concentration of .0001% by weight, it was rolled into paper, and the smell and taste when smoked were compared using the two-point discrimination method using the rolled tobacco of the above-mentioned shredded tobacco without the addition of this compound as a control product. .

In particular, the evaluations of 20 well-trained expert panels are 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 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 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 60S'. This compound isolated by the above method was added in the same manner as in Example 1, and the amount of -C added was added. was added by spraying to a concentration of 0.0005% by weight, then shredded and rolled up. The taste of the tobacco 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 This compound was added to C, M, C, (carboxymethylcellulose) paste, which is a paste for cigarette paper wrapping, at a concentration of 0.001 weight 7
A shredded rolled-up product of the sheet-shaped recycled tobacco produced in Example 2 was made using the mixture such that the ratio of 0. The taste of these products was compared using the following method.

The evaluation by a specially trained expert panel of 20 people was 0 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 furthermore, the irritating odor based on C, M, and C is significantly suppressed. found.

Claims (1)

[Claims] 1. A tobacco flavor improver comprising the compound occidenchlor represented by formula (1).