JPS5929176B2 - Flavor improver for tobacco - Google Patents

Description

[Detailed description of the invention] The present invention is a novel compound Decahydro-5°5.

8a-trimethyl-2-methylene-
1-(3-oxo-butyl)-1-naphtha
lene (common name 15016-ginollabder 8(1)
7) 1-en-13-one (hereinafter also referred to as the present compound) and a tobacco flavor improver comprising the present compound.

In recent years, the preference for cigarettes has been shifting towards lighter-tasting, richer-flavored tobacco products.As a result, the leaf tobacco used in product cigarettes is often lighter in flavor and contains less nicotine. I'm getting used to it. however,
Such raw leaf tobacco generally lacks aroma and flavor, so it is necessary to add various flavoring agents to improve the aroma and taste of the product. On the other hand, research is being conducted to produce flavorings suitable for such purposes through microbial conversion of certain compounds. No. 53-107482, No. 53-10
The description can be found in No. 7498, etc.

From this point of view, the present inventors conducted research with the aim of obtaining a useful tobacco flavoring agent by converting manur with microorganisms. The present inventors have discovered a new compound that is extremely effective as a converting substance for improving tobacco flavor and suppressing irritation, and has accomplished the present invention. That is, the present invention is a tobacco flavor improver comprising a compound represented by formula (I) and a compound represented by formula (I) above.

The compound represented by the structural formula of formula (1) is 15,16-dinollabda-8(17)-ene-13one (15,16-
DinOrlabd-8(17)-En-13-0ne
), which the present inventors isolated for the first time from the product obtained by microbial transformation of manur.

Manur used as a substrate for microbial conversion in the present invention is a known compound represented by the formula (
It is known as a raw material oil component such as (DaeIydium bif orme), and is also known as a synthetic raw material for fragrances. Next, the method for producing the compound of the present invention, ie, the method by microbial conversion of manur, will be explained step by step.

First, the JTS-162 strain (Feikoken Kyoiku No. 5702) is inoculated into a medium containing manur, and cultured aerobically at 28°C. After the converted culture solution is extracted with an organic solvent such as ethyl acetate or ethyl ether, the solvent is distilled off under reduced pressure to obtain a converted product. This conversion product is eluted with a solvent such as a hexane-ethyl acetate mixture using a silica gel column, and the compound represented by formula (1) is collected by fractionation. The microorganism JTS-162 used in the present invention is a microorganism isolated from the soil in Yokohama city, and its mycological properties are as follows.

1. Morphological properties (1) It is a bacillus, and the cell morphology changes as the culture progresses.

At the beginning of culture, cells elongate and branch. Culture 12
In ~14 hours, the cells undergo irregular division and then become rod-shaped. The size is (0.6-0.8)X at the early stage of culture.
(5 to 15) μm, (0.6 to 0.8) × (0
．． 8 to 1.8) μm. (2) Gram staining: Positive (3) Acid-fastness: Positive (4) Spore forming ability: None (5) Motility: None 2. Chemical composition analysis (1) The main amino acid constituting the cell wall is MesO-diaminopimelic acid.

(2) The content of guanine + cytosine in DNA is 62.
It is 5 mol%.

3. Culture findings (1) Broth agar plate culture (28℃, 6 days culture): Growth is rather slow, colony shape is circular, diameter is 1.5 to 2 inches. The periphery is wavy, the surface is smooth, and the color is white. As time passes, the color changes.

The color of the medium does not change. (2) Meat juice agar slant culture (28
℃, 4-day culture): Growth is rather slow.

The shape and color tone are the same as those for broth agar plate culture. (3) Meat juice liquid medium (cultured at 28°C for 6 days): The medium is not very cloudy.

A fungal film slowly forms on the surface and then settles to become sediment. When cultured with shaking, it shows uniform growth. (4
) Meat juice gelatin puncture culture (28°C, 6 weeks culture): No liquefaction, bacterial cells grew on the surface.

(5) Litmus milk (cultivated at 28°C for 6 weeks): slowly produces acid.

4. Physiological properties (1) Growth conditions: 20-30℃ is the optimum temperature for growth, pH is 6
．． The optimum value is 5 to 8.5; it cannot grow under anaerobic conditions.

2) Auxotrophy: None 3) Nitrate reduction: Positive 4) Starch hydrolysis: None 5) Citric acid utilization: Positive 6 Urease: Positive 7 Oxidase: Positive 8) Catalase: Positive 9) Pigment production: None 0I0-F test: Fermentative (auto) methyl red test: Negative (auto) V-P test: Negative (auto) Production of indole: None (auto) Production of acid and gas from the following sugars (auto) The following L-alanine, paraffin, pyruvate and ropionic acid grown using compounds as carbon sources.

(auto) Aesculin degradation: Positive (5) Tween 60 degradation: Positive (auto) Tyrosine degradation: Negative (LI avienol, sclareol, and L assimilation: Positive or higher results, Verges Manu* of Determination Be Bacteriology
rgey/SManualOfDeterminati
The present bacterial strain JTS-162 was identified as Nocardia restricta based on the 8th edition (1974).

Next, a more specific explanation will be given with reference to manufacturing examples. Production example Glucose 1.0%, Monosodium glutamate 0.5%,
K2HPO4O. l%, MgSO4・7H200.02
%, KClO. A MSG slant medium (PH7.2) consisting of Ol%, yeast extract 0.5%, and agar 1.5% was prepared in a test tube, inoculated with JTSl62 strain, and incubated at 28°C.
The cells were cultured for 3 days and used as a seed culture.

Then, (NH4)2S0427, K2HPO42y.
MgSO4・7H200.2y, CaCl2・2H20
0.0017, FeSO4・7H200.01t. H2
011! A liquid medium (PH 7.0) consisting of the following was placed in a 31-volume Erlenmeyer flask and sterilized at 121°C for 15 minutes. Add Manur 1 (commercial product) 1y and 1% T to the sterilized medium.
10 d of ween6O (surfactant, manufactured by Kanto Kagaku Co., Ltd.) aqueous solution was added. JTS-1 for 1 bottle of MSG slant medium
The inoculum of 62 strains was added to 5 ml of sterilized physiological saline (0.8%
, W/V) and inoculated into the liquid medium 11 described above. 6 at 210 rpm and 128°C using a rotary shaker.
After culturing for 0 hours, a conversion product was obtained. The present compound was obtained from this culture. That is, 1 ethyl acetate was added to the culture.
Extraction with stirring was carried out twice by adding 500 ml each time. The extracts were combined and the solvent was distilled off under reduced pressure.
A convertible product was obtained. Next, a column was made using 507 silica gel (manufactured by Mallinckrodt, 100 mesh),
The converted product was eluted with hexane:ethyl acetate (6:4/V) and collected in 8 ml portions using a fraction collector. This compound was eluted in the 15th to 17th fractions. These were combined, the solvent was distilled off under reduced pressure, and 0.0% of the oil was obtained.
087 (yield 8%) was obtained.

The results of spectrometry of this compound were as follows. Molecular formula Cl8H3OOl3C-NMRCCDC
l3, TMS], δ (Ppm): 14.3 (q), 17
．． 5(t), 19.4(t), 21.7(q), 24.
5(t), 29.8(q), 33.5(s), 33.6
(q), 38.3(t), 38.9(t), 39.7(
s), 42.1(t), 42.7(t), 55.5(d
), 56.3(d), 106,4(t), 148,1(
8), 208.1(s).

IR,. ? -1 :2940, 17201146011
440, 1360, 116018900MS. m/z:
262 (M+), 247, 244, 230, 204, 1
77, 13710795, 81, 55, 430 From the above results, it was confirmed that the present compound has a structure represented by formula ().

When added to tobacco and smoked, the compound of the present invention harmonizes well with the natural tobacco aroma, suppresses irritation, mellows the aroma, has a long-lasting effect, and is free from dissipation during the tobacco manufacturing process. It has been found that it has many excellent effects, including less

In order to use the compound of the present invention as a tobacco flavor improver, it is diluted with a solvent such as ethanol or ethylene glycol to an appropriate concentration of 0.01 to 3
The effect is exhibited by adding 0 ppm (w/w).

The types of tobacco to which the compounds of the present invention can be effectively applied are not particularly limited, and are effective not only for tobacco obtained through cultivation, but also for recycled tobacco, pipe tobacco, etc. manufactured from tobacco scraps. . EXAMPLES Hereinafter, the effects of the present invention will be specifically explained with reference to Examples.

Example 1 0.5~ of this compound was dissolved in 3 ml of ethanol, sprayed and added to shredded tobacco 1007 manufactured by Japan Monopoly Corporation (trade name: ``Chieri Ichi'') immediately before being rolled up, and the mixture was rolled into paper without the addition of this compound. Using the above-mentioned shredded tobacco rolls as a control, the odor and aroma when smoked were compared using a two-point discrimination method.

The evaluations by 20 specialized sensory test panels were as shown in Table 1. Example 2 Waste tobacco was 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 was beaten and 15% of the dry matter amount of kraft pulp was added to make a mixture. 1.0 of this compound was dissolved in 3 ml of ethanol and sprayed and added to the sheet-shaped recycled tobacco 1007, which was formed into a thin paper and the water-soluble portion was returned to the thin paper. The product was chopped and rolled into paper, and the aroma, aroma, and taste were compared using a two-point discrimination method using the cut and rolled paper of the above-mentioned sheet without the addition of the present compound as a control.

Claims (1)

[Claims] 1. A compound represented by formula (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) 2. Formula ( I
) A tobacco flavor improver consisting of a compound represented by: ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I)