JPH1042846A - Tobacco flavor enhancer - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce a fragrance compound which is non-volatile, stable during the manufacturing process and storage period of tobacco, and thermally decomposed during smoking to give an excellent fragrance and flavor improving effect. Flavor improving agent having such excellent properties. SOLUTION: The following formula (Formula 4) (Wherein, R represents a cis-3-hexenyl group, a benzyl group,
Tobacco production of a flavor enhancer containing a perfume glycoside represented by 2-phenylethyl group, 4- (3'-oxobutyl) phenyl group, 4-allyl-2-methoxyphenyl group) as an active ingredient. Add to raw materials or tobacco,
The fragrance compound generated by thermal decomposition during smoking of tobacco suppresses off-flavors originating from raw leaf tobacco.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to a flavor improving agent for tobacco, and more particularly to a flavor improving agent which is added to a raw material for tobacco production or tobacco to suppress off-flavors originating from raw leaf tobacco during smoking. The following formula capable of imparting flavor (Formula 2)

[0002]

Embedded image (Wherein, R represents a cis-3-hexenyl group, a benzyl group,
A fragrance glycoside represented by 2-phenylethyl group, 4- (3'-oxobutyl) phenyl group or 4-allyl-2-methoxyphenyl group) as an active ingredient. It relates to a taste improver.

[0003]

2. Description of the Related Art Burning of raw tobacco emits its own unique flavor and taste, and at the same time, stimulates, peculiar odor such as green odor or fresh odor, and astringency.
Dislikes such as bitterness occur. In order to solve these problems, it has been conventionally practiced to add one or more kinds of tobacco extracts or various plant extracts or various flavor compounds to tobacco leaves as tobacco flavoring agents. ing.

[0004] However, it is known that tobacco extract has a resinous odor accompanied by a blue odor, and as such, is not very valuable as a flavoring agent for tobacco [Research Report of Central Research Institute of Japan Monopoly Corporation, No. 88] Volume, pages 1-21
(1953)]. In addition, tobacco flavors comprising various plant extracts or various flavor compounds are exposed to high temperatures during the tobacco production process, for example, in processes such as a drying process and a puffing process. Since the flavoring is volatilized or thermally decomposed, most of the tobacco flavoring agent added to the raw leaf tobacco is lost, and there is a problem that the desired flavor-improving effect cannot be obtained as expected.

[0005]

Further, in recent years, consumers have diversified their preference for tobacco, and accordingly, tobacco having various various flavors has been produced. In response to these diversifications, crocodile, which is conventionally used as a flavoring agent for leaf tobacco, or a known perfume compound such as menthol or a plant extract alone cannot meet the demand for these diversifications. There is a strong demand for the development of new fragrance materials that can replace fragrances.

On the other hand, for the purpose of exhibiting a sufficient flavor-improving effect during smoking during the production process and the storage period of cigarettes, several tobacco flavor-improving agents containing a flavor glycoside have been proposed. I have. For example, as a fragrance glycoside,
A tobacco flavor enhancer containing terpene glucoside of menthol or borneol
According to Japanese Patent No. 219929), although the flavor and taste during smoking are improved to some extent, the terpenes are unstable to heat, so that the thermal decomposition during smoking causes generation of off-flavors such as decomposed odors. As a result, it is not possible to sufficiently satisfy the preference of smokers for diversified tobacco, and the appearance of further improved tobacco flavor improving agents is awaited.

[0007]

The present inventors have conducted intensive studies to solve the above-mentioned problems. As a result, the compound of formula (I) is non-volatile and stable under high temperature conditions as well as during the production and storage of tobacco, but during smoking, the fragrance glycoside is thermally decomposed and formed by pyrolysis. The fragrance compound has an excellent effect on improving the flavor and taste of tobacco, and the tobacco-like aroma and flavor are clearly displayed. The present invention was found to have an effect of improving aroma and flavor. That is, the present invention provides a compound represented by the following formula:

Embedded image (Wherein, R represents a cis-3-hexenyl group, a benzyl group,
A fragrance glycoside represented by 2-phenylethyl group, 4- (3'-oxobutyl) phenyl group or 4-allyl-2-methoxyphenyl group) as an active ingredient. It is a taste improver. Therefore, an object of the present invention is to add a fragrance glycoside that has not been used in conventional tobacco to tobacco and obtain a conventional flavor enhancer by using a fragrance compound generated by thermal decomposition during smoking. It is an object of the present invention to provide a flavor improving agent having excellent properties capable of reducing unseen green odor, astringency, and pungency, and increasing softness and swelling.

[0008]

BEST MODE FOR CARRYING OUT THE INVENTION Hereinafter, the present invention will be described in detail.
As the fragrance glycosides (hereinafter, also referred to as glucosides) included in the above formula (Chemical Formula 1) of the present invention, R is cis-3-hexenyl glucoside of a cis-3-hexenyl group, and R is benzyl. Group benzyl glucoside, where R is 2-
2-phenylethyl glucoside of phenylethyl group, R
Is a raspberry ketone glucoside having a 4- (3′-oxobutyl) phenyl group, and eugenol glucoside having a R is 4-allyl-2-methoxyphenyl group. These glucosides are, for example, compounds described in the conventional literature as components of raspberry fruit extracts (Phytochemistry 29 (12) 3853-3858, 1990).

According to the present invention, the production of the fragrance glycoside of the formula (Formula 1) can be easily carried out by reacting glucose and the corresponding alcohol by a known method. For example, about 2 to about 20 parts by weight of the above alcohols per 1 part by weight of glucose is added in the presence of about 0.1 to about 10 parts by weight of an acid such as hydrochloric acid, sulfuric acid, or an acidic ion exchange resin. The reaction is carried out at a temperature in the range of about -20 ° C to about 100 ° C for about 0.5 to about 24 hours. If necessary, the acid is removed by neutralization or filtration, and the alcohol is easily synthesized by recovering excess alcohols. it can. Furthermore, these glycosides can be purified using a means such as column chromatography. In addition, it is also possible to synthesize by using the conventionally known Koenigs-Knorr reaction [C
hem. Ber. , 34 957 (1901)].

The compound of the formula (Chemical Formula 1) of the present invention, which can be obtained as described above, is a colorless and odorless solid substance. It can impart floral-like (rose-like), honey-like, and spice-like aromas and sweetness to sweets, and can also impart tobacco, especially burley tobacco-like aroma and flavor characteristics. That is, by adding the fragrance glycoside of the formula (Formula 1) alone or together with another fragrance composition for tobacco to a cigarette, a pipe tobacco, etc., a green odor, a fresh odor, and a chemical during smoking of various tobacco leaves are obtained. Off-flavors such as odors, off-flavors such as cellulose decomposition odors, astringency, bitterness, pungency, off-flavors and irritations to the nose, throat, mouth, etc. As a result of the sensory test, it was clearly recognized that the original tobacco-like fragrance flavor had many excellent effects, such as a straightforward flavor, a swelling flavor, and an increase in smoke.

Further, by adding the tobacco flavor improving agent of the present invention to a tobacco-producing material such as a filter, the off-flavor and odor of mainstream smoke of tobacco can be suppressed, and the tobacco-like flavor and especially the smoke odor can be enhanced. Smooth, swelling and soft feeling. In addition, bone, recycled tobacco,
By adding it to artificial tobacco or the like, the same effect as described above can be obtained, and a tobacco product with a rich smoke sensation and improved flavor can be obtained.

The method, timing and means for adding the tobacco flavor enhancer obtained by the present invention are not particularly limited.
It can be added at an appropriate time by an appropriate means, but generally, the fragrance glycoside of the formula (Chemical Formula 1) is, like the other commonly used fragrance compounds, an organic solvent such as ethanol. Alternatively, after dissolving in water to obtain a flavor-improving agent, it can be added during a normal production process in the same manner as a water-soluble flavor or an alcohol-soluble flavor. Further, the amount of the fragrance glycoside added in the present invention is not particularly limited,
About 0.1% for raw tobacco or tobacco filter, etc.
Additions of the order of 00001 to about 0.1% by weight are often employed.

[0013]

The embodiments of the present invention will be described more specifically with reference to the following examples.

(Production Example 1) Synthesis of cis-3-hexenylglucoside 8 parts by weight of D-glucose, 6 parts by weight of cis-3-hexenol, and 0.2 parts by weight of a strongly acidic ion exchange resin were charged.
React for 8 hours at 0-85 ° C. After cooling the reaction mixture, the mixture is filtered through celite, and excess cis-3-hexenol is recovered from the mother liquor under reduced pressure. After adding three times the amount of water to the obtained crude product, it is washed with toluene to remove impurities. The toluene was recovered to obtain crude cis-3-hexenylglucoside (yield: 63.5%).

(Production Example 2) Benzyl glucoside and 2
-Synthesis of phenylethyl glucoside. The corresponding benzyl glucoside and 2-phenylethyl glucoside were synthesized in the same manner as in Production Example 1, except that benzyl alcohol and 2-phenylethyl alcohol were used instead of cis-3-hexenol in Production Example 1.

(Production Example 3) Synthesis of raspberry ketone glucoside. Charged raspberry ketone 1 part by weight, pentaacetylglucose 2.5 parts by weight, 10 parts by weight of toluene, BF ₃ ·
0.3 parts by weight of the ether complex are added at 20-25 ° C. After stirring at room temperature for 16 hours, the mixture is poured into water and extracted with toluene.
The oil layer is washed with a 5% aqueous sodium hydroxide solution and then with a 5% saline solution to recover toluene. To 1 part by weight of the obtained residual liquid, 3 parts by weight of methanol and 0.05 part by weight of a 28% sodium methoxide solution are added, and the mixture is stirred at room temperature for 1 hour. After neutralization with acetic acid, the solution was recovered to obtain raspberry ketone glucoside.

(Production Example 4) Synthesis of eugenol glucoside. Eugenol glucoside was synthesized in the same manner as in Production Example 3 except that Eugenol was used in place of Raspberry Ketone in Production Example 3.

Example 1 Cis-3 obtained in Production Example 1
-Hexenyl glucoside was dissolved in ethanol to give 0.0005% by weight of "Shinsei" brand engraved product and injected with a syringe to obtain Example 1. As a result of comparing the flavor of the product of Example 1 with the control product to which cis-3-hexenylglucoside was not added by a sensory test at the time of smoking by a specialized panel of 20 sensory inspectors, the flavor of the product of Example 1 was found. Is significantly reduced in blue odor, fishy odor, astringency, bitterness, and pungency compared to the control product.
Everyone acknowledged that the amount of smoke and body had increased significantly.

(Examples 2 to 5) Instead of cis-3-hexenyl glucoside used in Example 1, benzyl glucoside (Example product 2), 2-phenylethyl glucoside (Example product 3), raspberry ketone glucoside (Example product 4) and eugenol glucoside (Example product 5) were separately used in the same manner as in Example 1 using cigarettes added in exactly the same manner as in Example 1 to compare the aroma and flavor. The evaluation of the inspector was as shown in the following (Table 1).

[0020]

[Table 1]

The numbers in the table indicate that the flavor of the embodiment product or the control product is greenish, fresh, astringent,
Shows the number of specialized panelists who are judged to be superior in terms of increased tobacco-like aroma, smoke and body feeling with reduced bitterness and pungency. As is clear from (Table 1), the flavor improving agent containing the flavoring glycoside as an active ingredient in the present invention has remarkably blue, odor, astringency, bitterness, and pungency of tobacco leaves caused by tobacco raw materials. As a result, the tobacco flavor, smoke volume, and body feeling increased remarkably, and it was confirmed that the tobacco leaves had an excellent effect of improving the flavor and taste.

[0022]

According to the present invention, when the flavor enhancer of the present invention containing the flavor glycoside represented by the above formula (Formula 1) as an active ingredient is added to a raw material for tobacco production or tobacco, the raw leaf tobacco during smoking of the tobacco is added. The resulting off-flavor and off-odor can be suppressed, and the flavor and taste of tobacco leaves can be improved.

 ──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Masamichi Ito 335 Kariya, Hasegawa Nakagawa-ku, Kawasaki City, Kanagawa Prefecture Inside the Technical Research Institute (72) Inventor Toru Tachihara 335 Karijuku Hasegawa, Nakahara-ku, Kawasaki City, Kanagawa Prefecture Inside the company technology laboratory

Claims (1)

[Claims] (1) The following formula (Formula 1) (Wherein, R represents a cis-3-hexenyl group, a benzyl group,
A fragrance glycoside represented by 2-phenylethyl group, 4- (3'-oxobutyl) phenyl group or 4-allyl-2-methoxyphenyl group) as an active ingredient. Taste improver.