JPS5851883A - 15, 16-dinorlabudar-8(17)-ene-13-one and tobacco smoke taste modifier comprising same - Google Patents

Abstract

(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a novel compound Decahydro-5,5,8
a-trimethyl-2-methyl ene
-1-(3-oxo-butyl)-1-na p
The present invention relates to a flavor improver for tobacco ζ comprising h tha 1ene (commonly known as 1) 15.16-ditrulabdar8 (17)-7-13-ono (hereinafter also referred to as the present compound) and the present compound.

In recent years, the preference for cigarettes has shifted to lighter-tasting products with richer aromas.As a result, the raw material tobacco used in product cigarettes has become less palatable, with many having lower nicotine content. It has come to be used. However, such 11JC 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 flavoring agents for this purpose by microbial conversion of certain compounds. , same s3-xo74s
2M, No. 10153-107498, etc. From this point of view, the present inventors conducted research with the aim of obtaining a useful tobacco flavoring agent by microbially converting manur. By making certain microorganisms work under certain conditions, we discovered a new compound that is extremely effective as a converting substance in improving the flavor and suppressing irritation of tobacco, leading to the present invention.

That is, the present invention provides a compound represented by formula (1), a compound represented by formula (+
) is a compound represented by the structural formula 15.16-ditullabdar8 (17)-F-13-ono
inorlabd-8(17)-en-13-one
), which the present inventors isolated for the first time from the product obtained by microbial transformation of manur.

The 3-manul used as a substrate for microbial conversion in the present invention is a known compound represented by formula (11),
Yellow By/(Dakurijiu J. Biholme)(ye
low pine (Dacrydium bifo)
It is known as a cedar oil component such as rme)), and is also known as a synthetic raw material for fragrances.

Next, the method for producing the compound of the present invention, that is, the method by bioconversion of manur, will be explained in detail with reference to 11m'4. First, strain JTS-162 (Imitation Koken Moeyori No. 5702) is inoculated into a medium containing manur, and cultured aerobically at 28°C. After the converted culture solution is extracted with an aqueous bath medium such as gold, 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 hexa/ethyl acetate mixture using a phosphoric gel column and fractionated to collect the compound represented by formula (1).

Next, a more specific explanation will be given using manufacturing examples.

(Production example) Glucose 1.0%, monosodium glutamate 0.5%, K! I-IPo, 0.1chi, Mg5O,・7H,0
0.02%, KCtO801%, yeast extract 0.
MSG slant medium (pf (7
, 2) was prepared in a test tube, inoculated with JTS-162 strain, cultured at 28°C for 3 days, and used as [f]. Then, (NH4) x 804 2 gX KtH
P042 g, Mg 804・7H200゜2g
.

C! LCtl' 2H100,001g-, FeSO4
”7H!00.01 g.

A liquid medium (pH 7,0) consisting of 1 L of Hxo was placed in a Erlenmeyer flask and subjected to sterilization for 15 minutes at 121°C. Manur (commercial product) Ig and 1% Tween 60 (surfactant, manufactured by Kanto Kagaku Co., Ltd.) were added to the sterilized medium.
Water bath solution 10- was added. J for 1 bottle of M S G slant medium
A total of 51 Rt of the inoculum of TS-162 strain was dissolved in sterile physiological saline (0.8%, W/V), and the liquid medium 1 was added as a supplement.
Inoculated into T. 210 rI using a rotary shaker]
T+, culture was performed at 28°C for 60 hours to obtain a conversion product. The present compound was obtained from this culture. That is, 500+i of ethyl acetate was added once to the culture, and extraction with stirring was performed twice. The extracts were combined and the solvent was distilled off under reduced pressure to obtain 0.85 t of converted product. Next, a column was prepared using 5 (l) of silica gel (manufactured by Mallinckrodt, 100 ml), and the conversion product was bathed with t:hexa/:ethyl acetate (6:4 V/V), and the column was washed with a fraction collector. +l+7! fractions were collected.This compound was 15 to 17
It was eluted in the main fraction.

These were combined, the solvent was distilled off under reduced pressure, and the oily substances o, o
sr (yield: 8 cm) was obtained. The results of spectrometry of this compound are as follows.

Molecular formula Cul(no 04-tnC-NMt((CDCzs, TM8), a (pp
+n): 14.3 ((1), 17.5(t), 1
9.4(t), 2], 7(q), 24.
s (t), 29.8 (q), 33.5 (8 in 33.6
(q), 38.3(t), 38.9( enter 39.7(
8), 42.1(t).

42.7(enter s s, 5(d), 56.a(d
χ 106.4ft), 148.1 (pass 20 B, 1
(s).

IRXcm-': 2940.1720.1460
．． 1440.1360.1160.890°MS, m/@: 262(M), 247.244.23
0. 204.177.137.107.95.81
．． 55.43. .

From the above results, it was confirmed that this compound has a structure represented by formula (+).

When the compound of the present invention is added to tobacco and smoked, it harmonizes well with the original tobacco aroma, suppresses irritation, makes the aroma mellow, has a long-lasting effect, and has a low number of nuisances during the tobacco manufacturing process. It has been found that it has many excellent effects.

In order to use one dose of 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, and the concentration is 0.01 to 0.01 to
The effect by adding 30 ppm (w/w)
＆j6i4f The types to which the compounds of the present invention can be effectively applied are not limited to tobacco, and include not only tobacco obtained by cultivation, but also fresh tobacco and pipes manufactured from tobacco scraps. It is also effective against tobacco, etc.

EXAMPLES Hereinafter, the effects of the present invention will be specifically explained with reference to Examples.

Example 1 Just before rolling up, Japan Monopoly Corporation's product name 1 "Terry" shredded tobacco 10 (for liter; sword 11
After smoking, the smoked product was rolled into paper, and the odor and taste when smoked were compared using a two-point discrimination method using a rolled product of chopped Kt 1j without the addition of the present compound as a control. The evaluations of 20 professional sensory experts are as shown in Table 1.

Table 1 Note: Flavored products: Compounds added. The number indicates the number of people who said it was good. The * mark indicates a significant difference between samples with a risk rate of 1%.

Example 2 Waste tobacco is extracted with hot water at 100°C, separated into a water-bathable part and a water-insoluble part, the water-insoluble part is beaten, and 15% of dry weight kraft pulp is added to this mixture. was molded into a thin paper, and the above-mentioned water bath/sex part was returned to the thin paper to form a sorted recycled tobacco 10 (l) of the present compound t O ~
After adding 111 m to ethanol of i 3 and id, it was cut into 7 pieces and rolled up into paper, and the 7 cut and rolled pieces of the above sorting without the addition of this compound were used as a control, and two points were identified for odor, taste, and irritation. The aroma and taste were compared according to the method. The evaluations by 20 specialized sensory test panels were as shown in Table 2.

Note to Table 2: Addition of a compound, the number indicates the number of people who said it was good, and the * mark indicates a significant difference between samples with a risk factor of 1φ.

Patent issued! In Person Japan 1ji Public Corporation Procedural Amendment (Voluntary) June 1980 (0th Japan Patent Office Commissioner Shima 1) Haruki Tono1, Indication of the Case 1982 Patent Application No. 1487022, Masterpiece of Invention 15. 16-Jitullabdaa (17)-en-13
-Tobacco consisting of on and & flower gG, 4=y, 7, 41' bay, 73, Relationship with the case of the person making the amendment Patent applicant address 2-2-1 Toranomon, Minato-ku, Tokyo Name (4
56) Representative and President of Japan Monopoly Corporation Yoshinomatsu Izumi 4. Designated agent & Subject of amendment [Detailed description of the invention in the specification] 6. Existence of amendment (1) Page 5, line 2 of the specification, ``...'' Add the following sentence after "Collect."

``The microorganism J'I'S-162 used in the present invention is a microorganism isolated from soil in Yokohama city, and its mycological properties are as follows.

1. Morphological properties (1) Since it is a bacillus, the cell morphology changes as the culture progresses. At the early stage of culture, IY+1IIIi3I elongates and produces branches. After 12 to 14 hours of culture, the cells undergo irregular division and then become rod-shaped. The size is t (0.6~0.8) x (5 ~) pm at the beginning of culture,
After division: (0,6~o,o)x(o,s~1.8)μ
m.

(2) Durham staining: positive (3) acid fasting: positive (4) sporulation ability: none 5) movement Note: none 2-2. Chemical composition analysis (1) The main amino acids constituting the cell wall are meso- Diaminopimelic acid.

(2) The content of guanine + cytosine in DNA is 62.5
It's morchi.

3. Culture B: (1) Broth agar plate culture # (28℃, 6 days culture): growth is rather slow, colony shape is circular, diameter is 1.5-2,
1. The periphery is wavy, the surface is smooth, and the color is white, turning brown as the culture progresses. The color of the medium does not change.

(2) Juice agar plate culture (28°C, 4 days 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 between 28C and 613): The medium is not very cloudy. A bacterial film 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. Boxes grow on the surface 〇 = 3- (5) Lidomus milk (28°C, 6 weeks culture):
Slowly produces acid.

4. Physiological properties (1) Growth conditions: 20-30℃ is the optimum temperature for growth, pH
The optimum value is 6.5 to 8.5, and it cannot grow under anaerobic conditions.

(2) Auxotrophy: None 3) Nitrate reduction: Positive (4) Starch hydrolysis: None 5) Citric acid utilization: 1 (6) Urease: Positive (7) Oxidase: Positive (8 ) Catalase: Positive (9) Pigment production: None) 0-F test: Fermentative (9) Methyl red test: Negative (p) V-P test: Negative 0 ■ Indole production: None α-excellent Generation of acids and gases from sugars Acid gas LL-arabinose 10-2D-xylose + 3 D-glucose + -40-mannose 10-5D-fructose + 61)-galactose + -7 female bud sugar
18. Sucrose
10 -9 Lactose - 10 Trehalose + 11 I)-Sorvit +121)-Mannit + 13 Inosit + 14 Glycerin + 15 Starch - Ten......Production -......Production (b) Grows using the following compounds as carbon sources.

D, L-alanine, paraffin, pyruvic acid, propionic acid.

5- (Minute M of 171 Tween 6o: Positive 08) Decomposition of tyrosine: Negative (19) Assimilation of avienol, sclareol and manul: From the positive or higher results, Purge Aids Manual of Determinative Bacteriology (Bergey '
s Manual of I) eterninati
(ve) lacteriology), 8th edition (197
4), this strain JT8-162 was transformed into Nocardia restrifta (Noardia restrifta).
It was identified as a). ” Above 61

Claims (1)

[Scope of Claims] 1. A flavor improver for tobacco ζ, which comprises a compound represented by formula O), 2, and a compound represented by formula (1).