JPH0330659A - Method for improving aroma and flavor of tobacco - Google Patents
Method for improving aroma and flavor of tobaccoInfo
- Publication number
- JPH0330659A JPH0330659A JP16364189A JP16364189A JPH0330659A JP H0330659 A JPH0330659 A JP H0330659A JP 16364189 A JP16364189 A JP 16364189A JP 16364189 A JP16364189 A JP 16364189A JP H0330659 A JPH0330659 A JP H0330659A
- Authority
- JP
- Japan
- Prior art keywords
- tobacco
- aroma
- taste
- flavor
- compound
- 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.)
- Granted
Links
- 241000208125 Nicotiana Species 0.000 title claims abstract description 46
- 235000002637 Nicotiana tabacum Nutrition 0.000 title claims abstract description 46
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 11
- 235000019634 flavors Nutrition 0.000 title claims abstract description 11
- 238000000034 method Methods 0.000 title claims description 8
- 239000000463 material Substances 0.000 claims abstract description 8
- ZZEYQBNQZKUWKY-UHFFFAOYSA-N 4-Methyl-5H-furan-2-one Chemical compound CC1=CC(=O)OC1 ZZEYQBNQZKUWKY-UHFFFAOYSA-N 0.000 claims abstract description 6
- 235000019504 cigarettes Nutrition 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 6
- 230000007794 irritation Effects 0.000 abstract description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003960 organic solvent Substances 0.000 abstract description 2
- 206010016322 Feeling abnormal Diseases 0.000 abstract 1
- 235000009508 confectionery Nutrition 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 22
- 230000000694 effects Effects 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 6
- 239000000123 paper Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000012850 discrimination method Methods 0.000 description 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000000457 gamma-lactone group Chemical group 0.000 description 2
- 239000003292 glue Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229960002715 nicotine Drugs 0.000 description 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000019505 tobacco product Nutrition 0.000 description 2
- QIVUCLWGARAQIO-OLIXTKCUSA-N (3s)-n-[(3s,5s,6r)-6-methyl-2-oxo-1-(2,2,2-trifluoroethyl)-5-(2,3,6-trifluorophenyl)piperidin-3-yl]-2-oxospiro[1h-pyrrolo[2,3-b]pyridine-3,6'-5,7-dihydrocyclopenta[b]pyridine]-3'-carboxamide Chemical compound C1([C@H]2[C@H](N(C(=O)[C@@H](NC(=O)C=3C=C4C[C@]5(CC4=NC=3)C3=CC=CN=C3NC5=O)C2)CC(F)(F)F)C)=C(F)C=CC(F)=C1F QIVUCLWGARAQIO-OLIXTKCUSA-N 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
- 239000001768 carboxy methyl cellulose Substances 0.000 description 1
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 1
- 235000019506 cigar Nutrition 0.000 description 1
- 239000000039 congener Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002655 kraft paper Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 238000004161 plant tissue culture Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は３−メチル−２−ブテン−４−オリドをたばこ
および／またはたばこ製造用材料に添加して、たばこの
香喫味を改良する方法に関するものである。Detailed Description of the Invention (Industrial Application Field) The present invention provides a method for improving the aroma and taste of tobacco by adding 3-methyl-2-butene-4-olide to tobacco and/or tobacco manufacturing materials. It is related to.
（従来の技術と発明が解決しようとする課ｆｆり近年、
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（、香気の豊かな製品にその嗜好は移りつつある。(In recent years, the problems that conventional technology and inventions are trying to solve are
Cigarette preferences are showing a tendency to diversify, with preferences shifting toward products that are lighter in taste (and rich in 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ない緩和なもの
が多く使用されるようになってきた。又、脱ニコチン処
理を施して製造された、再製たばこ、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（す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。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、更に何らかの物質を添加し香喫味を向上させ
る必要がある。本発明者等はこれらの必要性から、各種
化合物の香喫味改良に有効な物質を探索すべく鋭意研究
を重ねてきた結果、本化合物が、たばこの香喫味改良に
優れた効果を示すことを見出し、本発明をなすに至った
。さらに詳細に述べると本発明者らはたばこ精油成分を
含む一般式
（但し、式中ＲＬ 、 Ｒ２は水素原子、メチル基、エ
チル基、イソプロピル基を表わし、Ｒ３は水素原子、メ
チル基を表わしＲ４は水素原子、メチル基、エチル基、
プロピル基、ブチル基、ペンチル基、ヘキシル基を表わ
し、表示＝は単結合、または二重結合を表わす。）で示
される各種γ−ラクトン同族体に着目し、たばこへの香
喫味を評価試験したところ、３−メチル−２−ブテン−
４−オリドが他のγ−ラクトン同族体には見出せないた
ばこ本来の香９とよく調和し、香りにせ奥と丸みを持た
せ、たばこらしさを強調させ、刺激を抑え、やわらかく
、スムーズな喫味感を付与し、更にこれらの効果の持続
性のあることなど多くの優れた効果を有していることが
判明した。In line with this, the raw material leaf tobacco used in product cigarettes has come to be often made of mild tobacco with a light taste and low nicotine and tar content. In addition, remanufactured cigarettes manufactured by removing nicotine, so-called artificial cigarettes made from plants other than leaf tobacco, or various inorganic and organic ingredients (hereinafter referred to as artificial cigarettes) have also come into use. There is. However, such tobacco raw materials generally lack aroma, are often irritating, and lack flavor, so it is necessary to add some substance to improve the aroma and taste. In response to these needs, the present inventors have conducted intensive research to search for substances that are effective in improving the flavor and aroma of various compounds, and as a result, they have found that the present compound exhibits an excellent effect in improving the flavor and flavor of tobacco. This finding led to the present invention. More specifically, the present inventors have developed a general formula containing tobacco essential oil components (wherein RL and R2 represent a hydrogen atom, a methyl group, an ethyl group, or an isopropyl group, R3 represents a hydrogen atom or a methyl group, and R4 represents a hydrogen atom or a methyl group). is a hydrogen atom, a methyl group, an ethyl group,
It represents a propyl group, a butyl group, a pentyl group, or a hexyl group, and the symbol = represents a single bond or a double bond. ) Focusing on various γ-lactone homologs, we conducted an evaluation test on the aroma of tobacco, and found that 3-methyl-2-butene-
4-olide harmonizes well with the natural aroma of tobacco, which cannot be found in other γ-lactone congeners, giving the aroma depth and roundness, emphasizing the tobacco-like flavor, suppressing irritation, and providing a soft, smooth taste. It has been found that it has many excellent effects, including the ability to impart and maintain these effects.
（課題を解決するための手段）
本発明は３−メチル−２−ブテン−４−オリドをたばこ
および／またはたばこ製造用材料に添加することを特徴
とするたばこの香喫味改良法である。(Means for Solving the Problems) The present invention is a method for improving the flavor and aroma of tobacco, which is characterized by adding 3-methyl-2-butene-4-olide to tobacco and/or tobacco manufacturing materials.
本化合物は既知（ヘルベチカ・キミカ・アクタ誌１９７
２年１８６６〜１８８２他）であり、下記に示されるよ
うな既知の方法で（ジャーナルオブザオルガニック ケ
ミストリー３２０１） ３３９０〜３３９４ １９Ｂ
？）に従い
３−メチル−２−ブテン−４−オリド
クロルアセトンを原料にし容易に合成でき、淡いクマリ
ン様香気を有する物質で香喫味改良剤として望ましい適
性を有する。This compound is known (Helvetica Quimica Acta 197
2, 1866-1882, etc.) and by known methods as shown below (Journal of the Organic Chemistry 3201) 3390-3394 19B
? ), it can be easily synthesized using 3-methyl-2-butene-4-olidochloroacetone as a raw material, has a light coumarin-like odor, and has desirable suitability as a flavor improver.
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、他の通常使用されろたばこ香料
と同様にエタノール等の有機溶媒または水に溶かした後
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
乙とによっても香喫味改良の効果をあげることができる
。又本化合物を適用しうるたばこの種類についても特に
限定されるものではなく、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、天然の１ａ誰或いは、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
は製品化されたのち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。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０．０００１〜０００１重五％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 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 or water and then adding it in pieces, like other commonly used tobacco flavorings. The effect of improving the aroma and taste can also be achieved by incorporating it into other materials for manufacturing cigarettes, such as wrapping paper, glue, or filters. There are no particular limitations on the types of tobacco to which this compound can be applied; in addition to cigarettes, pipe tobacco, cigar tobacco, etc. made from regular leaf tobacco, natural tobacco, or plant tissue culture. By adding the present compound to synthetic tobacco, etc., which are manufactured using synthetic tobacco products, during the manufacturing process or after the product has been manufactured, the aroma and taste of these products can be significantly improved. The amount of this compound added may be very small, and sufficient effects can be obtained at 0.00001 to 0.01% by weight, preferably 0.0001 to 0.5% by weight, based on tobacco or tobacco manufacturing materials, making it economical. There are also big advantages.
以下に実施例を挙げて本発明をさらに説明する。The present invention will be further explained below with reference to Examples.
（実施例−１）
巻き上げ直前の日本たばこ産業■商品名ｒｓｅｖｅｎ
５ｔａｒｓＪ用のたばこ刻み５０ｇに対して前述の方法
で合成した本化合物の０．１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％
になるように噴霧して添加した浸紙巻きし、本化合物無
添加の上記たばこ刻みの巻上量を対照品としてこれらを
喫煙した時の香り、味について二点識別法により比較し
た。特に訓練した専門パネル２０人の評価は第１表に示
す通りであった。(Example-1) Japan Tobacco Industry just before rolling ■Product name rseven
A 0.1% by weight ethanol solution of this compound synthesized by the above method was added to 50g of chopped tobacco for 5tarsJ.
The amount of this compound based on shredded tobacco is 0.0001% by weight
The aroma and taste when smoking these products were compared using the two-point discrimination method using the rolled up amount of the above-mentioned shredded tobacco to which the present compound was added as a control product. The evaluations of the 20 specially trained expert panels are shown in Table 1.
第１表 表中の数字は良いと評価した人数を示す。Table 1 The numbers in the table indicate the number of people who rated it as good.
印は危険率５％で有意差があることを示す。（以下同様
）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かる。The mark indicates a significant difference at a risk rate of 5%. (Similarly below) 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）
黄色種たばこ（上位葉茶）のたばこ刻み５００ｇに対し
、本化合物の１％水溶液をたばこ刻みに対する本化合物
の量が０、０００２重量％になるように噴霧添加して紙
巻きし、本化合物無添加の上記たばこ刻みの巻上げ品を
対照品として、これらを喫煙した時の香り、味及びくせ
について二点識別法により比較した。特に訓練した専門
パネル２０名の評価は第２表に示す通りであった。(Example-2) A 1% aqueous solution of the present compound was sprayed to 500 g of shredded yellow tobacco (upper leaf tea) so that the amount of the present compound relative to the shredded tobacco was 0,0002% by weight, and the paper was rolled. The aroma, taste, and habit of these products when smoked were compared using a two-point discrimination method using the above-mentioned rolled tobacco products without the addition of the present compound as a control product. The evaluations of the 20 specially trained expert panels are as shown in Table 2.
第２表
上′表から本化合物がたばこの香り、味およびくせを著
しく改善することが分かる。It can be seen from Table 2, top '', that this compound significantly improves the aroma, taste and habit of tobacco.
（実施例−３）
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バルブを加えた
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６０ｇ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ｏ、 ｏｏｏｓ重量％になるように噴霧した後
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。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。(Example 3) Waste tobacco is extracted with hot water at 100°C, separated into a water-soluble part and a water-insoluble part, and then the water-insoluble part is beaten, and a coniferous kraft valve corresponding to 15% of its dry weight is added to the water-insoluble part. A mixture of the above was added was molded into a thin paper, and the above-mentioned water-soluble portion was added back to the thin paper to form a recycled tobacco sheet.The present compound isolated by the method described above was added to 60 g of sheet-shaped recycled tobacco in the same manner as in Example-1. After spraying so that the additive amount was o, ooos weight %, the product was cut and rolled up, and the taste was compared using a two-point discrimination method using the cut and rolled-up product of the above-mentioned sheet-shaped recycled tobacco without the addition of the present compound as a control product. The evaluation by a specially trained expert panel of 20 people was as shown in Table 3.
第３表
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
分かる。Table 3 The results show that the products to which this compound was added had a marked improvement in aroma and taste, as well as a remarkable effect of suppressing irritation.
（実施例−４）
たばこ刻みの紙巻き用糊であるＣ、Ｍ、Ｃ，（カルボキ
シメチルセルロース）糊液に本化合物を０００１重景％
になるように混合したものを用いて、実施例−３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。特に訓練
された専門パネル２０人による評価は第４表に示す通り
であった。(Example-4) This compound was added to C, M, C, (carboxymethylcellulose) paste, which is paste for paper wrapping of shredded tobacco, at a concentration of 0001%.
Using the mixture so that The taste of these products was compared using the following method. The evaluation by a specially trained expert panel of 20 people was as shown in Table 4.
第４表
Ｃ，Ｍ、Ｃ，に基づく刺激臭が著しく抑制されろことが
分かる。It can be seen that the irritating odors based on C, M, and C in Table 4 are significantly suppressed.
（発明の効果）
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（調和し、香
りにせ奥と丸味を持たせ、たばこらしさを強調させ、刺
激を抑え、やわらかくスムーズな喫味感を付与し、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。(Effects of the Invention) When this compound was added to various tobacco raw materials that had a irritating aroma and taste, and an evaluation test was conducted on the aroma and taste of these materials, it was found that this compound was in harmony with the original tobacco aroma, It has been found to have many excellent effects, including giving the aroma a deeper and rounder flavor, emphasizing the tobacco-like character, suppressing irritation, giving a soft and smooth taste, and that these effects are long-lasting. .
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二゛で
鳩、′ｌ４ＨＪ＞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.
Claims (1)
またはたばこ製造用材料に添加することを特徴とするた
ばこの香喫味改良法。3-Methyl-2-butene-4-olide in tobacco and/or
Or a method for improving the flavor and aroma of tobacco, which is characterized by adding it to materials for cigarette manufacturing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16364189A JPH0740909B2 (en) | 1989-06-28 | 1989-06-28 | Tobacco flavor improvement method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16364189A JPH0740909B2 (en) | 1989-06-28 | 1989-06-28 | Tobacco flavor improvement method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0330659A true JPH0330659A (en) | 1991-02-08 |
| JPH0740909B2 JPH0740909B2 (en) | 1995-05-10 |
Family
ID=15777807
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16364189A Expired - Lifetime JPH0740909B2 (en) | 1989-06-28 | 1989-06-28 | Tobacco flavor improvement method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0740909B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH063123U (en) * | 1992-06-29 | 1994-01-18 | 株式会社堅徳商会 | Shoulder strap for shoulder bag Top end fitting |
| CN104522875A (en) * | 2014-12-28 | 2015-04-22 | 中国烟草总公司郑州烟草研究院 | Cigarette sweet aroma spice module formula |
-
1989
- 1989-06-28 JP JP16364189A patent/JPH0740909B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH063123U (en) * | 1992-06-29 | 1994-01-18 | 株式会社堅徳商会 | Shoulder strap for shoulder bag Top end fitting |
| CN104522875A (en) * | 2014-12-28 | 2015-04-22 | 中国烟草总公司郑州烟草研究院 | Cigarette sweet aroma spice module formula |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0740909B2 (en) | 1995-05-10 |
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