JPS5831914B2 - Flavor improver for tobacco - Google Patents

Flavor improver for tobacco

Info

Publication number
JPS5831914B2
JPS5831914B2 JP16585481A JP16585481A JPS5831914B2 JP S5831914 B2 JPS5831914 B2 JP S5831914B2 JP 16585481 A JP16585481 A JP 16585481A JP 16585481 A JP16585481 A JP 16585481A JP S5831914 B2 JPS5831914 B2 JP S5831914B2
Authority
JP
Japan
Prior art keywords
tobacco
compound
aroma
taste
added
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
Application number
JP16585481A
Other languages
Japanese (ja)
Other versions
JPS5867175A (en
Inventor
邦雄 加藤
進 久保
令子 植垣
嶺 藤森
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Japan Tobacco Inc
Original Assignee
Japan Tobacco and Salt Public Corp
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Japan Tobacco and Salt Public Corp filed Critical Japan Tobacco and Salt Public Corp
Priority to JP16585481A priority Critical patent/JPS5831914B2/en
Publication of JPS5867175A publication Critical patent/JPS5867175A/en
Publication of JPS5831914B2 publication Critical patent/JPS5831914B2/en
Expired legal-status Critical Current

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  • Pyrane Compounds (AREA)

Description

【発明の詳細な説明】 本発明はオフシブノール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 tobacco flavor improver comprising ofsibunol.

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ってきた。
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.

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ってきている。
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.

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、更に伺等かの
物質を添加し香喫味を向上させる必要がある。
However, such tobacco raw materials generally lack aroma and are often irritating and lack flavor, so it is necessary to further add other substances such as tobacco to improve the aroma and taste.

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化合物を提供する
ことを目的とするものである。
From this point of view, it is an object of the present invention to provide a 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、フイチュ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 solavetibone, solanascone, and huituverol, 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
植物の葉からオフシブノール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喫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った。
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. The present inventors succeeded in isolating offsibunol from the leaves of Rustica plants, and also discovered that this compound is extremely effective as a tobacco flavor improver, leading to the present invention.

すなわち、本発明は(1)式で表わされる化合物オフシ
ブノール(以下本化合物という)からなるたばこ用香喫
味改良剤である。
That is, the present invention is a tobacco flavor improver comprising the compound ofsibunol (hereinafter referred to as the present compound) represented by formula (1).

本化合物は既に公知の化合物であり、ヒノキ科のニオイ
ヒバの精油成分として記載(テトラヘドロン・レターズ
誌・1970年235頁)がある。
This compound is already a known compound and has been described as an essential oil component of Hibarium nigra, a member of the Cupressaceae family (Tetrahedron Letters, p. 235, 1970).

しかし、たばこの香喫味改良剤として優れた効果を発揮
するという用途については現在まで全く知られていない
However, until now, there has been no knowledge of its use as an excellent tobacco flavor improver.

本化合物は、生育中のニコチアナ属ルスチカ植物の葉に
植物ウィ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エーテル=80:20(容積比)で
溶出してくる分画につき分取ガスクロマトグラフィーを
行うことにより単離することができる。
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 applying the steam distillate to a silicate column. It can be isolated by performing preparative gas chromatography on the fraction eluted with a hexane-ether system of 80:20 (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・ウィルスを接種する。
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.

接種の方法は通常の方法、すなわち全葉の葉面に400
〜600メ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0.1MIJン酸緩衝液に懸濁させ
た植物ウィルス(濃度0.75μ97me )を塗布す
るいわゆる塗床接種法でよい。
The method of inoculation is the usual method, that is, 400 ml of
A so-called bed inoculation method may be used, in which a plant virus (concentration 0.75μ97me) suspended in water or 0.1MIJ acid buffer is applied while sprinkling ~600 mesh of carborundum and making a wound.

植物ウィルス接種後6日目に、病斑の大部分が直径約1
間以上になった葉を採取する。
Six days after inoculation with the plant virus, most of the lesions were approximately 1 in diameter.
Harvest leaves that have grown older.

採取した葉5ooyを真空凍結乾燥機を用いて凍結乾燥
を行い、凍結乾燥品110gを得る。
5ooy of the collected leaves are freeze-dried using a vacuum freeze dryer to obtain 110 g of a freeze-dried product.

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
6.4gを得る。
The freeze-dried product was extracted three times with dichloromethane (No. 31), and the extracts were combined and concentrated under reduced pressure to obtain 6.4 g of a crude extract concentrate.

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300ydのエーテル抽出
液を得、エーテル抽出液は前記と同様濃縮し水蒸気蒸留
エーテル抽出濃縮物890ηを得る。
The crude extract concentrate was subjected to steam distillation and ether extraction using a steam distillation continuous extractor to obtain 300 yd of ether extract, and the ether extract was concentrated in the same manner as above to obtain 890 η of steam distilled ether extract concentrate.

この濃縮物につきケイ酸IFI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:エーテル=8
0:20(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。
This concentrate was subjected to column fractionation using a hexane-ether system using silicate IFI, and hexane:ether = 8
The fraction eluted at 0:20 (volume ratio) is concentrated in the same manner as above.

この濃縮物から、FFAP(フリー・ファテイー・アシ
ッド・ポリエステル)10%、1mのカラムを用いて1
00°Cから240℃まで10℃/yrunの昇温で分
取ガスクロマトグラフィーを行うことにより保持時間1
0分に、本化合物を白色結晶として計約10■得ること
ができる。
From this concentrate, 10% FFAP (Free Fatty Acid Polyester) was added using a 1 m column.
By performing preparative gas chromatography at a temperature increase of 10°C/yrun from 00°C to 240°C, the retention time 1
In 0 minutes, a total of about 10 cm of this compound can be obtained as white crystals.

(収率、乾葉1g当り約0.097n?)。(Yield, about 0.097 n/g dry leaf?).

本化合物は次のようなスペクトルを示す。This compound shows the following spectrum.

質量分析スペクトル(70eV) : m/z (%)
44(72)、59(100)、77(23)、79(
32)、91(26)、93(22)、95(52)、
107(36)、108(31)、121(24)、1
35(29)、203(11)、+ 218(10)、221(8)、236(M。
Mass spectrometry spectrum (70eV): m/z (%)
44 (72), 59 (100), 77 (23), 79 (
32), 91 (26), 93 (22), 95 (52),
107 (36), 108 (31), 121 (24), 1
35 (29), 203 (11), + 218 (10), 221 (8), 236 (M.

12)。12).

赤外線吸収スペクトル(液膜) : cm ’3420
.1655.1200,1130.1100゜ 核磁気共鳴スペクトル(CDCl2):δ(ppm)1
.11(3H−s )、1.23 (6H−s)、1.
653H−d)、2.28 (I H−ddd)、4.
25LH−dd)、5.98 (IH−d)、5.98
(IH・brs )。
Infrared absorption spectrum (liquid film): cm '3420
.. 1655.1200, 1130.1100° Nuclear magnetic resonance spectrum (CDCl2): δ (ppm) 1
.. 11 (3H-s), 1.23 (6H-s), 1.
653H-d), 2.28 (I H-ddd), 4.
25LH-dd), 5.98 (IH-d), 5.98
(IH・brs).

本化合物は、甘い花様香気を有する物質で、たばこの香
喫味改良剤として望ましい適性を有する。
The present compound is a substance with a sweet flower-like aroma, and has desirable suitability as a tobacco flavor improver.

すなわち、香喫味に欠は刺激を有する種々のたばこ原料
に本化合物を添加し、これらの香喫味について評価試験
を行ったところ、本化合物はたばこ本来の香りとよく調
和し、香りに丸味をもたせ、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 had a irritating aroma and flavor, and an evaluation test was conducted on the aroma and taste of these materials, it was found that this compound harmonized well with the original tobacco aroma and gave a rounded flavor to the aroma. , emphasizes the tobacco-like character,
It has been found that it has many excellent effects, such as suppressing irritation and 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、その他紙巻きたばこ製造用の材料品
例えば巻紙、糊或いはフィルター等に含有させることに
よっ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
きたばこ、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。
There are also 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く微量で良く、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 is 0.00001 to 0.01% by weight based on tobacco or tobacco manufacturing materials.
Desirably, a sufficient effect can be obtained by adding 0.0001 to 0.001% by weight, which is economically advantageous.

実施例 1 巻き上げ直前の日本専売公社商品名「チェリー」用のた
ばこ刻み50.9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% by weight ethanol solution of the present compound isolated by the above method was added to 50.9 pieces of tobacco for Japan Monopoly Corporation (trade name: Cherry) just before rolling, and the amount of the present compound relative to the chopped tobacco was added. The compound was added by spraying to a concentration of 0.0001% by weight, then rolled into paper, and the odor and taste when smoked were compared using the two-point discrimination method using the rolled tobacco of the above-mentioned shredded tobacco without the addition of this compound as a control product. did.

特に訓練された専門パネル20人の評価は第1表に示す
通りであった。
The evaluations of 20 specially trained expert panels are as shown in Table 1.

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。
From the above table, it can be seen that this compound has the effect of significantly improving the aroma and taste of product tobacco.

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%にあたる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
もどして作ったシート状再生たばこ6CB9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。
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 coniferous kraft pulp corresponding to 15% of its dry weight was added. The mixture was molded into a thin paper, and the above-mentioned water-soluble portion was added back to the thin paper to make a sheet-shaped recycled tobacco 6CB9. This compound isolated by the above method was added in the same manner as in Example 1, and the amount added was 0. After spraying and adding the compound to a concentration of .0005% by weight, the tobacco was cut and rolled up, and the taste was compared using a two-point discrimination method using a cut 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
示す通りであった。
The evaluation by a specially trained expert panel of 20 people was as shown in Table 2.

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。
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G、M、C,(カルボキシ
メチルセルロース)糊液に本化合物をo、ooi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 The present compound was added to G, M, C, (carboxymethylcellulose) glue, which is a glue for cigarette shredded paper, in an amount of o, ooi weight percent.
A shredded rolled-up product of the sheet-shaped recycled tobacco produced in Example 2 was made using the mixture such that
These smoking tastes were compared using the two-point discrimination method.

特に訓練された専門パネル20人による評価は第3表に
示す通りであった。
The evaluation by a specially trained expert panel of 20 people was as shown in Table 3.

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。
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 furthermore, the irritating odor based on C, M, and C is significantly suppressed. found.

Claims (1)

【特許請求の範囲】[Claims] 1(1)式で表わされる化合物オフシブノールよりなる
たばこ用喫味改良剤。
1. A tobacco flavor improver comprising the compound offsibunol represented by formula (1).
JP16585481A 1981-10-19 1981-10-19 Flavor improver for tobacco Expired JPS5831914B2 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP16585481A JPS5831914B2 (en) 1981-10-19 1981-10-19 Flavor improver for tobacco

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP16585481A JPS5831914B2 (en) 1981-10-19 1981-10-19 Flavor improver for tobacco

Publications (2)

Publication Number Publication Date
JPS5867175A JPS5867175A (en) 1983-04-21
JPS5831914B2 true JPS5831914B2 (en) 1983-07-09

Family

ID=15820251

Family Applications (1)

Application Number Title Priority Date Filing Date
JP16585481A Expired JPS5831914B2 (en) 1981-10-19 1981-10-19 Flavor improver for tobacco

Country Status (1)

Country Link
JP (1) JPS5831914B2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103524472A (en) * 2013-10-23 2014-01-22 云南烟草科学研究院 Phenolic compound, and preparation method and application thereof

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9329157B2 (en) 2012-08-10 2016-05-03 Dionex Softron Gmbh Switching valve for liquid chromatography

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103524472A (en) * 2013-10-23 2014-01-22 云南烟草科学研究院 Phenolic compound, and preparation method and application thereof

Also Published As

Publication number Publication date
JPS5867175A (en) 1983-04-21

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