JPS5932451B2 - Oxidol Isomer 1 and tobacco flavor improver - Google Patents
Oxidol Isomer 1 and tobacco flavor improverInfo
- Publication number
- JPS5932451B2 JPS5932451B2 JP14209482A JP14209482A JPS5932451B2 JP S5932451 B2 JPS5932451 B2 JP S5932451B2 JP 14209482 A JP14209482 A JP 14209482A JP 14209482 A JP14209482 A JP 14209482A JP S5932451 B2 JPS5932451 B2 JP S5932451B2
- Authority
- JP
- Japan
- Prior art keywords
- tobacco
- compound
- aroma
- isomer
- taste
- 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
Links
Landscapes
- Manufacture Of Tobacco Products (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
【発明の詳細な説明】
本発明は新規化合物オクシドール・アイソマー・1なら
びに該化合物よりなるたばこ用香喫味改良剤に関するも
のである。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound oxidol isomer 1 and a tobacco flavor improver comprising the compound.
近年たばこの嗜好は多様化の傾向を示しているが、特に
喫味が軽く香気の豊かな製品にその嗜好は移りつつある
。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.
これに伴い製品たばこに配合される原料葉たばこは喫味
が軽快でニコチン及びタール含量の少い緩和なものが多
く使用されるようになつてきた。又、脱ニコチン処理を
施して製造された再生たばこ、葉たばこ以外の植物或い
は各種の無機成分や有機成分等からなるいわゆる人工た
ばこ(以下人工たばこという)等も使用されるようにな
つてきている。しかし、このようなたばこ原料は一般に
香気が乏しく刺激を有することが多く旨味にも欠ける為
、更に何等かの物質を添加し香喫味を向上させる必要が
ある。本発明はかかる観点から、特に香気が乏しく刺激
を有し旨味に欠ける葉たばこ、再生たばこ、人工たばこ
等を原料とするたばこの香喫味を向上させる新規化合物
を提供することを目的とするものである。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 new 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. .
従来、たばこの香喫味改良に有効な物質としては数多く
の化合物が知られており、葉たばこの中にもともと含ま
れているセスキテルペノイドであるソラベチボン、ソラ
ナスコン、フイチユベロール等もその一つの化合物群で
ある。A large number of compounds have been known as substances that are effective in improving the aroma and taste of tobacco, and sesquiterpenoids originally contained in leaf tobacco, such as solavetibon, solanascone, and huyuberol, are one such group of compounds.
本発明者等はセスキテルペノイド系化合物であればたば
この香気とよく調和し効果的であろうとの予測に基づき
、セスキテルペノイドを単離すべく鋭意研究を重ねてき
た結果、植物ウィルスを接種したニコチアナ属ルスチカ
植物の葉から新規化合物オクシドール・アイソマー・1
を単離することに成功するとともに、本化合物がたばこ
の香気味改良剤として極めて有効であることを見出し本
発明をなすに至つた。すなわち、本発明は(I)式で表
わされる化合物オクシドール・アイソマー・1(以下本
化合物という)及び該化合物よりなるたばこ用香喫昧改
良剤である。本化合物は本発明者等により天然界より初
めて単離された化合物であり、その合成法も現在まで未
知であつた。The present inventors have conducted extensive research to isolate sesquiterpenoids based on the prediction that sesquiterpenoid compounds would be effective as they harmonize well with the aroma of tobacco, and found that Nicotiana spp. Novel compound occidol isomer 1 from the leaves of the Rustica plant
The present inventors succeeded in isolating the compound and found that it is extremely effective as a tobacco flavor improver, leading to the present invention. That is, the present invention is a compound represented by formula (I), oxidol isomer 1 (hereinafter referred to as the present compound), and a tobacco flavor improver comprising the compound. This compound was the first compound isolated from nature by the present inventors, and its synthesis method was unknown until now.
従つて、本化合物がたばこの香喫昧改良剤として優れた
効果を発揮することについても現在まで全く知られてい
ない。本化合物は、生育中のニコチアナ属ルスチカ植物
の葉に植物ウイルスを接種したのち一定期間経過後にこ
れを採取し、該葉を有機溶剤で抽出して水蒸気蒸留を行
い、水蒸気蒸留物をケイ酸カラムを用いてヘキサン−エ
ーテル系で分画し、ヘキサンリエーテル一80:20(
容量比)で溶出してくる分画につき分取ガスクロマトグ
ラフイ一を行うことにより単離することができる。Therefore, until now, it has not been known at all that this compound exhibits excellent effects as a 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 distilling the steam distillate into a silicate column. Fractionate with hexane-ether system using
It can be isolated by performing preparative gas chromatography on the fraction eluted at a volume ratio).
次に本化合物の単離方法の一例を示す。Next, an example of a method for isolating this compound will be shown.
ニコチアナ属ルスチカ植物50本を通常のたばこ栽培法
により畑地もしくは温室内で約2ケ月間生育させたのち
、全葉面にタバコ・モザイク・ウイルスを接種する。接
種の方法は通常の方法、すなわち全/葉の葉面に400
〜600ブツシユのカーボランダムをふりかけ、傷をつ
けながら水もしくは0.1Mリン酸緩衝液に懸濁させた
植物ウイルム(濃度0.75μ7/MOを塗布するいわ
ゆる塗沫接種法でよい。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, i.e. 400 ml on the whole/leaf surface.
The so-called smear inoculation method may be used, which involves sprinkling ~600 bushes of carborundum and applying it to a plant virus suspended in water or 0.1M phosphate buffer (concentration 0.75 μ7/MO) while making a wound.
植物ウイルス接種後6日目に病斑の大部分が直径約1m
T1以上になつた葉を採取する。採取した葉8007を
真空凍結乾燥機を用いて凍結乾燥を行い、凍結乾燥品1
10クを得る。凍結乾燥品は31のジクロルメタンで3
回抽出を繰り返し、その抽出液を合わせて減圧濃縮を行
い粗抽出濃縮物6.4クを得る。粗抽出濃縮物は水蒸気
蒸留連続抽出装置を用いて水蒸気蒸留及びエーテル抽出
を行い300m1のエーテル抽出液を得、エーテル抽出
液は前記と同様に濃縮し水蒸気蒸留エーテル抽出濃縮物
890m9を得る。この濃縮物につきケイ酸15クを用
いてヘキサン−エーテル系でカラム分画を行い、ヘキサ
ンリエーテル=80:20(容量比)で溶出してくる分
画を前記と同様の方法で濃縮する。この濃縮物から、F
FAP(フリー・フアテイ一・アシツド・ポリエステル
)10%のカラムを用いて分取ガスクロマトグラフイ一
を行うことにより、保持時間10分に本化合物を白色結
晶として約5η得ることができる。(収率乾葉1ク当り
約0.05η)。本化合物は次に示すスペクトルデータ
によりオクシドール・アイソマ一・1であると同定され
た。On the 6th day after inoculation with the plant virus, most of the lesions were approximately 1 m in diameter.
Collect leaves that have reached T1 or higher. Freeze-dry the collected leaves 8007 using a vacuum freeze dryer to obtain freeze-dried product 1.
Get 10 points. The lyophilized product is 31 dichloromethane and 3
The extraction is repeated twice, and the extracts are combined and concentrated under reduced pressure to obtain 6.4 units of crude extract concentrate. The crude extract concentrate is subjected to steam distillation and ether extraction using a steam distillation continuous extractor to obtain 300 ml of ether extract, and the ether extract is concentrated in the same manner as described above to obtain 890 ml of steam distilled ether extract concentrate. This concentrate is subjected to column fractionation using a hexane-ether system using 15 grams of silicic acid, and the fraction eluted with hexane ether=80:20 (volume ratio) is concentrated in the same manner as described above. From this concentrate, F
By performing preparative gas chromatography using a 10% FAP (free fat acid polyester) column, approximately 5η of the present compound can be obtained as white crystals in a retention time of 10 minutes. (Yield: approximately 0.05 η per dry leaf). This compound was identified as occidol isomer 1.1 based on the spectral data shown below.
質量分析スペクトル(70eV):m/z(%)59(
53)、119(26)、145(21)、157(1
00)、159(23)、185(37)、200(2
6)、
218(M+、5)
赤外線吸収スペクトル:CTIl−1
3450、1605、1460、1385、核磁気共鳴
スペクトル(CDCl3) :δ(Ppm)プロトン1
.28(6H.Σ)、2.20(6H.s)、6.90
(2H,.S)カーボン
14.9(↓)、20.4(t)、24.0(V)、2
6.6(J)、27.3(ル)、28.9(y)、30
.7(t)、46.3(す)、72.7(足)、125
.9(d)、127.1(d)、133.5(s)、1
34.2(s)、
134.9(s)、
本化合物は清涼感を伴う薄い木様香気を有する物質であ
り、たばこの香喫昧改良剤として望ましい適性を有する
。Mass spectrometry spectrum (70eV): m/z (%) 59 (
53), 119 (26), 145 (21), 157 (1
00), 159 (23), 185 (37), 200 (2
6), 218 (M+, 5) Infrared absorption spectrum: CTIl-1 3450, 1605, 1460, 1385, Nuclear magnetic resonance spectrum (CDCl3): δ (Ppm) proton 1
.. 28 (6H.Σ), 2.20 (6H.s), 6.90
(2H,.S) Carbon 14.9 (↓), 20.4 (t), 24.0 (V), 2
6.6 (J), 27.3 (le), 28.9 (y), 30
.. 7 (t), 46.3 (su), 72.7 (foot), 125
.. 9(d), 127.1(d), 133.5(s), 1
34.2(s), 134.9(s), This compound is a substance that has a light woody aroma accompanied by a refreshing feeling, and has desirable suitability as a tobacco flavor improver.
すなわち、香喫昧に欠け刺激を有する種々のたばこ原料
に本化合物を添加し、これらの香喫昧について評価試験
を行つたところ、本化合物はたばこ本来の香りとよく調
和し、香りに丸昧をもたせ、たばこらしさを強調させ刺
激を抑え、更にこれらの効果に持続性のあることなど多
くの優れた効果を有することが判明した。In other words, when this compound was added to various tobacco raw materials that lacked aroma and were irritating, and an evaluation test was conducted on the aroma of these materials, it was found that this compound harmonized well with the original tobacco aroma and was completely immersed in the aroma. It has been found that it has many excellent effects, such as enhancing tobacco flavor, emphasizing the tobacco-like taste, suppressing irritation, and having long-lasting effects.
本化合物をたばこ原料に添加する時期及び手段は特に限
定されるものではなく、他の通常使用される香料と同様
にエタノール等の有機溶剤に溶かした後、たばこ刻みに
添加して使用でき、その他紙巻たばこ製造用の材料品例
えば巻紙、糊或いはフイルタ一等に含有させることによ
つても香喫味改良の効果をあげることができる。The timing and means of adding this compound to tobacco raw materials are not particularly limited, and it can be used by dissolving it in an organic solvent such as ethanol and adding it to shredded tobacco like other commonly used flavorings, or by adding it to shredded tobacco. The effect of improving flavor and aroma can also be achieved by incorporating it into materials for manufacturing cigarettes, such as wrapping paper, glue, filters, etc.
又、本化合物を適用しうるたばこの種類についても特に
制限はなく、通常の葉たばこを原料として製造する紙巻
たばこ、パイプたばこ、葉巻たばこ等の他、屑たばこを
原料として製造される再生たばこ、天然の繊維或いは植
物の組織培養物を用い製造される合成たばこ等に対して
もこれらの製造工程中又は製品化された後本化合物を添
加することにより、これらの香喫味を著しく改良するこ
とができる。Furthermore, there are no particular restrictions on the types of tobacco to which this compound can be applied, including cigarettes, pipe tobacco, cigar tobacco, etc. made from regular leaf tobacco, recycled tobacco made from scrap tobacco, and natural tobacco. 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. .
本化合物の添加量は極微量で良く、たばこ又はたばこ製
造用材料品に対し、0.00001〜0.01重量%望
ましくは0.0001〜0.001重量%の添加で充分
な効果が得られるので経済的にも大きな利点がある。The amount of this compound added may be extremely small, and a sufficient effect can be obtained by adding 0.00001 to 0.01% by weight, preferably 0.0001 to 0.001% by weight, to the tobacco or tobacco manufacturing materials. Therefore, there is a great economic advantage.
実施例 1
巻き上げ直前の日本専売公社商品名「チエリー用」のた
ばこ刻み50yに対して前述の方法で単離した本化合物
の0.01重量%エタノール溶液を、たばこ刻みに対す
る本化合物の量が0.0001重量%になるよう噴霧し
て添加したのち紙巻し、本化合物無添加の上記たばこ刻
みの巻上品を対照品として、これらを喫煙した時の匂い
、味について二点識別法により比較した。Example 1 A 0.01 wt % ethanol solution of the present compound isolated by the above method was added to 50 y of shredded tobacco of Japan Monopoly Corporation's brand name "For Thierry" just before rolling, until the amount of the present compound relative to the shredded tobacco was 0. After adding the compound by spraying it to a concentration of .0001% by weight, it was rolled up into paper, and the odor and taste when smoked were compared using a two-point discrimination method using the roll of the above-mentioned shredded tobacco without the addition of this compound as a control product.
特に訓練された専門パネル20人の評価は第1表に示す
通りであつた。上表から本化合物は製品たばこの香り及
び味を著しく改良する効果を有することが分る。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
性部とに分けた後水不溶性部を叩解し、これにその乾物
重量の15%の針葉樹のクラフトパルプを加えた混合物
を薄紙状に成型し、この薄紙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60クに対し前述の方法で
単離した本化合物を実施例1と同様にしてその添加量が
0.0005重量%になるよう噴霧して添加した後裁刻
して巻き上げ、本化合物無添加の上記シート状再生たば
この裁刻巻き上げ品を対照品として二点識別法により喫
味を比較した。The evaluations of 20 specially trained expert panels were 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 15% of the dry weight of softwood kraft pulp was added thereto. The mixture was molded into a thin paper, and the above-mentioned water-soluble portion was added back to the thin paper to make 60 sheets of recycled tobacco.The compound isolated by the method described above was added in the same manner as in Example 1, and the amount of addition was adjusted. It was added by spraying to a concentration of 0.0005% by weight, then shredded and rolled up, and the taste 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.
特に訓練された専門パネル20人による評価は第2表に
示す通りであつた。この結果、本化合物を添加したもの
は香り及び味が著しく改善されると共に刺激の抑制効果
も顕著であることが分る。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.
実施例 3
たばこ刻みの紙巻用糊であるC.M.C.(カルボキシ
メチルセルロース)糊液に本化合物を0.001重量%
になるよう混合したものを用いて実施例2で製造したシ
ート状再生たばこの裁刻巻き上げ品を作り、別途本化合
物無添加の糊液を用いた巻き上げ品を対照品として、二
点識別法によりこれらの喫味を比較した。Example 3 C. M. C. (Carboxymethyl cellulose) 0.001% by weight of this compound in the paste liquid
Cut and rolled products of the sheet-shaped recycled tobacco manufactured in Example 2 were made using the mixture such that We compared the tastes of these.
特に訓練された専門パネル20人による評価は第3表に
示す通りであつた。この結果、本化合物はたばこ製造用
材料品である巻き上げ接着用の糊に添加してもたばこの
香り及び味を改善し、更にC.M.C.に基づく刺激臭
が著しく抑制されることが判明した。The evaluation by a specially trained expert panel of 20 people was 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 also improves the aroma and taste of cigarettes. M. C. It was found that the irritating odor caused by
Claims (1)
I )で表わされる化合物より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] A compound represented by the primary formula (I)▲There are mathematical formulas, chemical formulas, tables, etc.▼(I) A compound represented by the secondary formula (I)
A tobacco flavor improver consisting of the compound represented by I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(I)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14209482A JPS5932451B2 (en) | 1982-08-18 | 1982-08-18 | Oxidol Isomer 1 and tobacco flavor improver |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP14209482A JPS5932451B2 (en) | 1982-08-18 | 1982-08-18 | Oxidol Isomer 1 and tobacco flavor improver |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS5931722A JPS5931722A (en) | 1984-02-20 |
JPS5932451B2 true JPS5932451B2 (en) | 1984-08-09 |
Family
ID=15307282
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP14209482A Expired JPS5932451B2 (en) | 1982-08-18 | 1982-08-18 | Oxidol Isomer 1 and tobacco flavor improver |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPS5932451B2 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6156058U (en) * | 1984-09-14 | 1986-04-15 |
-
1982
- 1982-08-18 JP JP14209482A patent/JPS5932451B2/en not_active Expired
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6156058U (en) * | 1984-09-14 | 1986-04-15 |
Also Published As
Publication number | Publication date |
---|---|
JPS5931722A (en) | 1984-02-20 |
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