JPS5929176B2 - Flavor improver for tobacco - Google Patents
Flavor improver for tobaccoInfo
- Publication number
- JPS5929176B2 JPS5929176B2 JP14870281A JP14870281A JPS5929176B2 JP S5929176 B2 JPS5929176 B2 JP S5929176B2 JP 14870281 A JP14870281 A JP 14870281A JP 14870281 A JP14870281 A JP 14870281A JP S5929176 B2 JPS5929176 B2 JP S5929176B2
- Authority
- JP
- Japan
- Prior art keywords
- tobacco
- culture
- compound
- present
- positive
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- Manufacture Of Tobacco Products (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
【発明の詳細な説明】 本発明は新規な化合物Decahydro−5゜5。[Detailed description of the invention] The present invention is a novel compound Decahydro-5°5.
8a−trimethyl−2−methylene−
1−(3一oxo−butyl)−1−naphtha
lene(慣用名15016−ジノルラブダー 8(1
7)一エンー13 ーオン、以下本化合物ともいう)及
び本化合物からなるたばこ用香喫味改良剤に関するもの
である。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.
近年、たばこの嗜好は喫味が軽く香気の豊かな製品へと
移りつつあるが、これに伴なつて製品たばこに配合され
る原料葉たばこは、喫味が軽くニコチン含量が少ないも
のが多く使用されるようになつてきた。しかしながら、
このような原料葉たばこは一般に香気に乏しく、うまみ
に欠けるため、種々の香味料を添加して製品の香喫味の
向上をはかることが必要とされる。一方、かかる目的に
適する香味料をある種の化合物の微生物転換によつて製
造する研究が行なわれており、例えば、ヨノン系化合物
の微生物転換によるたばこ用香料としては特開昭53一
12498号、同53−107482号、同53−10
7498号などにその記載がみられる。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.
本発明者らは、かかる観点からマヌールを微生物転換す
ることによつて有用なたばこ香料を得ることを目的とし
て研究を行なつたところ、マヌールに一定の条件下であ
る種の微生物を働かせることにより、転換物質としてた
ばこの香喫味改善及び刺激抑制にきわめて有効な新規化
合物を見い出し、本発明をなすに至つた。すなわち、本
発明は式(I)で示される化合物、および上記(I)式
で表わされる化合物からなるたばこ用香喫味改良剤であ
る。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.
式(1)の構造式で示される化合物は15・16−ジノ
ルラブダ一8(17)一エン一13オン(15・16−
DinOrlabd−8(17)−En一13−0ne
)と称される新規化合物で、本発明者らがマヌールを微
生物転換することにより得られた生成物中より初めて単
離したものである。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.
本発明において微生物転換の基質として用いるマヌール
は式()で示される公知化合物であり、イエロ一・パイ
ン(ダクリジウム ビホルメ)〔YellOwpine
(DaeIydiumbifOrme))等の材油成分
として知られており、香料の合成原料としても知られて
いる。次に本発明の化合物の製造法、すなわちマヌール
の微生物転換による方法を順を追つて説明する。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.
まず、マヌールを含む培地にJTS−162株(微工研
菌寄第5702号)を接種し、28℃で好気的に培養を
行なう。転換の終了した培養液を、酢酸エチル、エチル
エーテル等の有機溶媒で抽出したのち、溶媒を減圧下で
留去し、転換生成物を得る。この転換生成物をシリカゲ
ルカラムを用いて、ヘキサン−酢酸エチル混液などの溶
媒により溶出し、分取することによつて式(1)で示さ
れる化合物を採取する。本発明において使用する微生物
JTS−162は横浜市内の土壌中より単離された微生
物で、その菌学的性質は以下の通りである。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.形態的性質
(1)桿菌であり、細胞の形態は培養の経過に伴ない変
化する。1. Morphological properties (1) It is a bacillus, and the cell morphology changes as the culture progresses.
培養の初期には細胞は伸長し、分枝を生ずる。培養12
〜14時間で細胞は不規則な分断を生じ、その後短桿状
となる。大きさは培養の初期には(0.6〜0.8)X
(5〜15)μm、分断後は(0.6〜0.8)×(0
.8〜1.8)μmとなる。(2)グラム染色性:陽性
(3)抗酸性:陽性
(4)胞子形成能:なし
(5)運動性:なし
2.化学的組成分析
(1)細胞壁の構成主要アミノ酸はMesO−ジアミノ
ピメリン酸である。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) DNA中のグアニン+シトシンの含量は62.
5モル%である。(2) The content of guanine + cytosine in DNA is 62.
It is 5 mol%.
3.培養所見
(1)肉汁寒天平板培養(28℃、6日培養):生育は
やや遅くコロニーの形は円形、直径は1.5〜2篤』周
辺は波状、表面は平滑、色調は白色で培養の経過に伴い
かつ色になる。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.
培地の色は変化しない。(2)肉汁寒天斜面培養(28
℃、4日培養):生育はやや遅い。The color of the medium does not change. (2) Meat juice agar slant culture (28
℃, 4-day culture): Growth is rather slow.
形状、色調は肉汁寒天平板培養に同じ。(3)肉汁液体
培地(28℃、6日間培養):培地はあまり濁らない。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.
表面にゆつくりと菌膜が形成され、その後沈降して沈査
となる。振とうして培養すると均一な生育を示す。(4
)肉汁ゼラチン穿刺培養(28℃、6週間培養):液化
せず、表面に菌体が生育。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)リトマス・ミルク(28℃、6週間培養):ゆつ
くりと酸を生成する。(5) Litmus milk (cultivated at 28°C for 6 weeks): slowly produces acid.
4.生理的性質
(1)生育条件:20〜30℃が生育の適温、PHは6
.5〜8.5が適値、嫌気的条件下では生育できない。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)栄養要求性:なし
3)硝酸塩の還元:陽性
4)デンプンの加水分解:なし
5)クエン酸の利用:陽性
6 ウレアーゼ:陽性
7 オキシダーゼ:陽性
8)カタラーゼ:陽性
9)色素の生成:なし
0I0−Fテスト:醗酵的
(自)メチルレツドテスト:陰性
(自)V−Pテスト:陰性
(自)インドールの生成:なし
(自)以下の糖類から酸及びガスの生成
(自)以下の化合物を炭素源として生育す冫L−アラニ
ン、パラフイン、ピルビンrロピオン酸。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.
(自)エスクリンの分解:陽性
(5)ツウイーン60の分解:陽性
(自)チロシンの分解:陰性
(LIアビエノール、スクラレオール及びルの資化:陽
性
以上の結果から、バージエイズ・マニユ
※オブ・デターミネーテイブ・バクテリオロジ一(Be
rgey/SManualOfDeterminati
veBacterlOlOgy)、第8版(1974年
)に基づき、本菌株JTS−162をノカルデイア・レ
ストリクタ(NOcardiarestricta)と
同定した。(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).
次に製造例を掲げてさらに具体的に説明する。製造例グ
ルコース1.0%、グルタミン酸ナトリウム0.5%、
K2HPO4O.l%、MgSO4・7H200.02
%、KClO.Ol%、イーストエキスト0.5%、寒
天1.5%から成るMSG斜面培地(PH7.2)を試
験管内に作り、これにJTSl62株を接種し、28℃
で3日間培養し、これを種菌として用いた。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.
ついで、(NH4)2S0427、K2HPO42y.
MgSO4・7H200.2y、CaCl2・2H20
0.0017、FeSO4・7H200.01t.H2
011!から成る液体培地(PH7.O)を31容三角
フラスコに入れ、121℃で15分間滅菌を行なう。滅
菌後の培地にマヌール1 (市販品)1yと、1%のT
ween6O(界面活性剤、関東化学株式会社製)水溶
液10dを加えた。MSG斜面培地1本分のJTS−1
62株の種菌体を5m1の滅菌済生理食塩水(0.8%
、W/V)にけんだくし、前述の液体培地11に接種し
た。回転振とう機を用いて、210rpm128℃で6
0時間培養を行ない転換生成物を得た。この培養物から
本化合物を得た。すなわち、該培養物へ酢酸エチルを1
回当り500m1ずつ加えて、2回攪拌抽出を行なつた
。抽出液を合して、溶媒を減圧下で留去し、0.857
の転換物を得た。次いで507のシリカゲル(マリンク
ロツト社製、100メツシユ)を用いてカラムを作り、
転換生成物をヘキサン:酢酸エチル(6:4/V)で溶
出し、フラクシヨンコレクタ一で8m1ずつ分取Cした
。本化合物は15〜17本目の分取液中に溶出していた
。これらを合し、溶媒を減圧下で留去し、油状物質0.
087(収率8%)を得た。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.
本化合物のスペクトロメトリ一の結果は以下のようであ
つた。分子式 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)。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
以上の結果より、本化合物は式()で示される構造であ
ることが確認された。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 ().
本発明の化合物は、たばこに添加して喫煙した場合、た
ばこ本来の香りとよく調和し、刺激を抑え、香りをまろ
やかにし、さらに効果に持続性があり、たばこの製造工
程中における逸散が少ないなど多くのすぐれた効果を有
していることが判明した。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
本発明の化合物をたばこの香喫味改良剤として使用する
には、エタノール、エチレングリコール等の溶媒で適当
な濃度に希釈し、製品たばこ原料に対応し0.01〜3
0ppm(w/w)添加することによりその効果を発揮
する。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).
本発明の化合物を有効に適用しうるたばこの種類は特に
限定されるものではなく、栽培により得られるたばこの
みならず、屑たばこを原料として製造される再生たばこ
及びパイプたばこ等にも有効である。以下、実施例によ
り本発明の効果を具体的に説明する。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.
実施例 1
巻上直前の日本専売公社商品名[チエリ一」用たばこ刻
み1007に対し、本化合物0.5〜を3m1のエタノ
ールに溶解して噴霧一添加した後、紙巻し、本化合物無
添加の上記たばこ刻みの巻上品を対照として、これらを
喫煙したときのにおい及び昧について二点識別法により
比較した。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.
専門官能検査パネル20人の評価は第1表に示すとおり
であつた。実施例 2
屑たばこを100℃の熱水で抽出し、水溶性部と水不溶
性部に分けた後、水不溶性部を叩解し、これに乾物量の
15%のクラフトパルプを加えた混合品を薄紙状に成型
し、この薄紙状に上記の水溶性部をもどして作つたシー
ト状再生たばこ1007に対して、本化合物1.0即を
3m1のエタノールに溶解して噴霧・添加したのち、才
刻して紙巻し、本化合物無添加の上記シートの才刻、巻
上品を対照として、におい、昧、および刺激について二
点識別法により香喫味を比較した。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)
)で示される化合物からなるたばこ用香喫味改良剤。 ▲数式、化学式、表等があります▼( I )[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)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14870281A JPS5929176B2 (en) | 1981-09-22 | 1981-09-22 | Flavor improver for tobacco |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14870281A JPS5929176B2 (en) | 1981-09-22 | 1981-09-22 | Flavor improver for tobacco |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5851883A JPS5851883A (en) | 1983-03-26 |
JPS5929176B2 true JPS5929176B2 (en) | 1984-07-18 |
Family
ID=15458681
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14870281A Expired JPS5929176B2 (en) | 1981-09-22 | 1981-09-22 | Flavor improver for tobacco |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5929176B2 (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5501862A (en) * | 1993-12-22 | 1996-03-26 | Givaudan-Roure Corporation | Alkyl carbonate derivatives of sclareol diol |
-
1981
- 1981-09-22 JP JP14870281A patent/JPS5929176B2/en not_active Expired
Also Published As
Publication number | Publication date |
---|---|
JPS5851883A (en) | 1983-03-26 |
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