JP2014512825A - タバコに由来する成分及び物質 - Google Patents
タバコに由来する成分及び物質 Download PDFInfo
- Publication number
- JP2014512825A JP2014512825A JP2014508509A JP2014508509A JP2014512825A JP 2014512825 A JP2014512825 A JP 2014512825A JP 2014508509 A JP2014508509 A JP 2014508509A JP 2014508509 A JP2014508509 A JP 2014508509A JP 2014512825 A JP2014512825 A JP 2014512825A
- Authority
- JP
- Japan
- Prior art keywords
- tobacco
- isolate
- compounds
- desired compounds
- solvent
- 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
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- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
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- BJHIKXHVCXFQLS-UYFOZJQFSA-N fructose group Chemical group OCC(=O)[C@@H](O)[C@H](O)[C@H](O)CO BJHIKXHVCXFQLS-UYFOZJQFSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 239000008187 granular material Substances 0.000 description 1
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- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
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- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
- A24B15/241—Extraction of specific substances
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23G—COCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
- A23G1/00—Cocoa; Cocoa products, e.g. chocolate; Substitutes therefor
- A23G1/0003—Processes of manufacture not relating to composition or compounding ingredients
- A23G1/0006—Processes specially adapted for manufacture or treatment of cocoa or cocoa products
- A23G1/0009—Manufacture or treatment of liquid, cream, paste, granule, shred or powder
- A23G1/0016—Transformation of liquid, paste, cream, lump, powder, granule or shred into powder, granule or shred; Manufacture or treatment of powder
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B13/00—Tobacco for pipes, for cigars, e.g. cigar inserts, or for cigarettes; Chewing tobacco; Snuff
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/24—Treatment of tobacco products or tobacco substitutes by extraction; Tobacco extracts
- A24B15/26—Use of organic solvents for extraction
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
- A24B15/18—Treatment of tobacco products or tobacco substitutes
- A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
- A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/21—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a non-condensed ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
- C07C35/23—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings
- C07C35/36—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with hydroxy on a condensed ring system having two rings the condensed ring system being a (4.4.0) system, e.g. naphols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H3/00—Compounds containing only hydrogen atoms and saccharide radicals having only carbon, hydrogen, and oxygen atoms
- C07H3/04—Disaccharides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Toxicology (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Manufacture Of Tobacco Products (AREA)
Abstract
【選択図】なし
Description
Stillら、J.Org.Chem.42:2923−2925(1978)及びAndrewsへの米国特許第4,591,442号にて議論されている。Biotage、Teledyne Isco、Grace Davison Discovery Sciences及びBuchiを含むメーカーから種々の自動化されたフラッシュクロマトグラフィ方式が利用可能である。フラッシュクロマトグラフィは、カラムが通常相対的に大きな粒子サイズを有し(たとえば、大まかに30〜40μm)、大量の試料を収容することができ、注入当たり単離されるさらに多くの当該化合物を可能にするので、合理的に大量の化合物を提供するのに望ましくてもよい。
ゆるく乾燥した嗅ぎ薬、噛みタバコ、粉砕したタバコ片(たとえば、丸薬、錠剤、球形、コイン、ビーズ、横長形又は豆の形状を有する)、押し出した又は形成されたタバコ細長片、小片、ロッド、円筒又は棒、微細に分割し、磨り潰した粉、紛体化した小片及び成分の微細に分割した又は粉にした塊、薄片様の小片、成形し、加工したタバコ片、タバコを含有するガムの小片、テープ様の膜の巻物、水に溶けやすい又は水分散性の膜若しくは細片(Chanへの米国特許出願公開番号2006/0198873)、又は外殻を加工しているカプセル様の物質(たとえば、天然では透明、無色、半透明である又は高度に着色している、曲げやすい又は硬質の外殻)及び内部領域を加工しているタバコ又はタバコ風味(たとえば、一部の形態のタバコを組み入れるNewtoniam液又はチキソトロピー液)のような無煙タバコ製品に組み入れることができる。種々の種類の無煙タバコ製品は、それぞれ参照によって本明細書に組み入れられるSchwartzへの米国特許第1,376,586号;Leviへの同第3,696,917号;Pittmanらへの同第4,513,756号;Sensabaugh,Jr.らへの同第4,528,993号;Storyらへの同第4,624,269号;Townsendへの同第4,987,907号;Sprinkle,IIIらへの同第5,092,352号;及びWhiteらへの同第5,387,416号;Stricklandらへの米国特許出願公開番号2005/0244521及びEngstromらへの同2008/0196730;ArnarpらへのPCT WO04/095959.;AtchleyらへのPCT WO05/063060;BjorkholmへのPCT WO05/016036及びQuinterらへのPCT WO05/041699にて言及されている。それぞれ参照によって本明細書に組み入れられるAtchleyらへの米国特許第6,953,040号及びAtchleyらへの同第7,032,601号;Williamshwへの同米国特許出願公開番号2002/0162562;Williamsへの同2002/0162563;Atchleyらへの同2003/0070687;Williamsへの同2004/0020503;Breslinらへの同2005/0178398;Stricklandらへの同2006/0191548;Holton,Jr.らへの同2007/0062549;Holton,Jr.らへの同2007/0186941;Stricklandらへの同2007/0186942;Dubeらへの同2008/0029110;Robinsonらへの同2008/0029116;Muaらへの2008/0029117;Robinsonらへの同2008/0173317及びNeilsenらへの2008/0209586にて言及された種類の無煙タバコの配合組成、成分及び加工方法も参照のこと。
本発明の特定の態様を説明するために言及され、その限定として解釈されるべきではない以下の実施例によって本発明の態様をさらに完全に説明する。
スクロースエステル、ルテイン、センブラトリエンジオール及びシス−アビエノールの抽出及び単離
抽出
分取用規模の液体クロマトグラフィを一般に用いて複雑な混合物における当該化合物を分離し、回収する(たとえば、Waters2707自動試料採取器、Waters DAD検出器、Waters2545四次勾配モジュール、及びWatersフラクションコレクターIIIを含み、WatersμBondapak C18 19x300mmのカラムとフラクションコレクターを備えたWatersの分取用LC方式を用いて)。
分取用規模の液体クロマトグラフィによってタール様の層からスクロースエステルを単離する。タール様の混合物をメタノールに溶解し(大まかに20mg/ml)、36ml/分の流速、75:25のメタノール:水の均一濃度分析、及び214nmでのWatersのDAD検出器によって操作する上述のWatersの分取用LC方式に注入する(1ml)。スクロースエステル標準の既知の保持時間に相当する分画(約1.0と約5.6分の間に回収される)を回収し、合わせる。およそ1.6分でスクロースエステルと一緒に溶出する別の主要ピークに注目する。これら分画のHR−LC−MS解析は、このピークがクエルセチン−3−ルチノシド又はルチンに相当することを示す。HR−LC−MS解析によって決定されるタール様混合物におけるルチンの濃度はおよそ800μg/gである。
上述のように先ずルチノシドを取り除くように処理するタール様の層から分取用LC方式によってルテインを単離する。常温にて対称分取用C18、19×300mm、7μm粒子のカラムを含み、26m1/分の流速、当初比75:25、10分で75:25、15分で100:0及び25分で75:25のメタノールと水の溶媒系:水、及び443nmでのWatersのDAD検出器で操作する分取用LC方式(10ml、注入体積)にルチノシドを含まない混合物を注入する。合計分析時間30分で試行全体を通して40秒分画を回収するようにフラクションコレクターを設定する。これらの条件下(分取用LC方式に以前注入したルテイン標準と相関して)にてルテインはおよそ18.7分で溶出する。
分取用規模の液体クロマトグラフィによってタール様の層からセンブラトリエンジオールを単離する。上述のようなタール様の層の試料をフラッシュクロマトグラフィ方式に注入する(1ml、注入体積)。36ml/分の流速、均一濃度の溶媒系(75:25のメタノール:水)及び214nmで設定した検出器によってフラッシュクロマトグラフィ方式を操作する。214nmでシグナルを生じる分画をフラッシュクロマトグラフィ方式にて回収した。合計分析時間10分で試行全体を通して20秒分画を回収するようにフラクションコレクターを設定する。β−センブラトリエンジオール及びα−センブラトリエンジオールの標準の保持時間を用いて、これらの化合物のそれぞれに相当する分画を回収し、別々に合せた。この方式では、β−センブラトリエンジオールは9.0分で溶出し、α−センブラトリエンジオールは6.9分で溶出する。
分取用規模の液体クロマトグラフィによってタール様の層からシス−アビエノールを単離する。タール様の層の試料を上述のように先ず、ルチノシドを取り除くように処理する。常温にて対称分取用C18、19×300mm、10μm粒子のカラムを含み、36m1/分の流速、75:25の比のメタノールと水の一定濃度の溶媒系、及び214nmでのWatersのDAD検出器で操作する分取用LC方式(10ml、注入体積)にルチノシドを含まない混合物を注入する。合計分析時間20分で試行(各12mlの)全体を通して20秒分画を回収するようにフラクションコレクターを設定する。これらの条件下にてシス−アビエノールはおよそ17.0分で溶出する。
スクロースエステル、ルテイン、センブラトリエンジオール及びシス−アビエノールの抽出及び単離
スクロースエステル及びセンブラトリエンジオールの抽出及び単離
Claims (29)
- 風味物質として有用なNicotiana種の植物から化合物を抽出し、単離する方法であって、
Nicotiana種の植物物質を受け取ることと、
植物物質から1以上の所望の化合物を溶媒に抽出するのに十分な時間及び条件下で植物物質を溶媒に接触させることと、
抽出した植物物質から1以上の所望の化合物を含有する溶媒を分離することと、
1以上の所望の化合物を含有する溶媒を精製して少なくとも約75重量パーセントの1以上の所望の化合物を含む単離物を提供することを含み、
1以上の所望の化合物が、ソラノン、ネオフィタジエン、メガスティグマトリエノン、β−ダマセノン、ノルソラナジオン、シス−アビエノール、α−センブラトリエンジオール、β−センブラトリエンジオール、スクロースエステル、ルテイン、それらの分解産物、及びそれらの混合物から成る群から選択される方法。 - Nicotiana種の植物物質が、葉全体、積層物、切断充填物、拡大した体積、葉柄、切断して巻いた葉柄、切断して膨らませた葉柄、再構成したタバコ、及び粒子状物質から成る群から選択される形態である請求項1の方法。
- Nicotiana種の植物物質が、緑葉形態又は乾燥した形態で提供される請求項1の方法。
- 溶媒がメタノールである請求項1の方法。
- 1以上の所望の化合物が、シス−アビエノール、α−センブラトリエンジオール、β−センブラトリエンジオール、スクロースエステル、及びルテインから成る群から選択される請求項4の方法。
- 溶媒が乾燥蒸気である請求項1の方法。
- 1以上の所望の化合物が、ソラノン、ネオフィタジエン、メガスティグマトリエノン、β−ダマセノン、及びノルソラナジオンから成る群から選択される請求項6の方法。
- 接触工程がさらに蒸留物を回収することを含む請求項6の方法。
- 蒸留物が水性層及び油性層を含む請求項8の方法。
- 1以上の所望の化合物を含有する溶媒が、油性層、水性層、及び蒸留工程から生成される廃棄蒸気から成る群から選択される請求項9の方法。
- 精製工程が分取用規模の液体クロマトグラフィを使用することを含む請求項1の方法。
- 精製工程がフラッシュクロマトグラフィを使用することを含む請求項1の方法。
- 精製工程が、約90重量%を超える1以上の所望の化合物を含む単離物を提供する請求項1の方法。
- 精製工程が、約95重量%を超える1以上の所望の化合物を含む単離物を提供する請求項1の方法。
- 単離物を処理してそれから1以上の分解産物を提供することをさらに含み、処理することが酸化、熱処理及びそれらの組み合わせから選択される請求項1の方法。
- 単離物がルテインを含み、1以上の分解産物がメガスティグマトリエノン、β−ダマセノン及びそれらの混合物から成る群から選択される請求項15の方法。
- 単離物がシス−アビエノールを含み、1以上の分解産物がスクラレオリド、スクラレオール及びそれらの混合物から成る群から選択される請求項15の方法。
- 喫煙物品又は無煙タバコ組成物での使用に適合させたタバコ組成物に単離物を加えることをさらに含む請求項1〜17のいずれかの方法。
- 単離物が、タバコ細長片に適用される外皮配合若しくは先端装飾配合の形態で、又は再構成されたタバコ材料の成分の形態で加えられる請求項18の方法。
- タバコ組成物が喫煙物品での使用に適合させたタバコ材料を含む請求項18の方法。
- タバコ組成物における単離物の量が、喫煙物品におけるタバコ材料の総乾燥重量に基づいて約5ppm〜約5重量パーセントの間である請求項20の方法。
- タバコ組成物が、無煙タバコ製品での使用に適合させたタバコ材料を含む請求項18の方法。
- タバコ組成物における単離物の量が、無煙タバコ製品におけるタバコ材料の総乾燥重量に基づいて約5ppm〜約5重量パーセントの間である請求項22の方法。
- Nicotiana種の植物又はその成分に由来する単離物であって、単離物が、少なくとも約75重量パーセントの、ソラノン、ネオフィタジエン、メガスティグマトリエノン、β−ダマセノン、ノルソラナジオン、シス−アビエノール、α−センブラトリエンジオール、β−センブラトリエンジオール、スクロースエステル、ルテイン、及びそれらの分解産物から成る群から選択される1以上の所望の化合物を含む単離物。
- 単離物が、約90重量%を超える1以上の所望の化合物を含む請求項24の単離物。
- 単離物が、約95重量%を超える1以上の所望の化合物を含む請求項24の単離物。
- 単離物が、メガスティグマトリエノン、β−ダマセノン及びそれらの混合物から成る群から選択される、ルテインの1以上の分解産物を含む請求項24の単離物。
- 単離物が、スクラレオリド、スクラレオール及びそれらの混合物から成る群から選択される、シス−アビエノールの1以上の分解産物を含む請求項24の単離物。
- 請求項24の単離物を含む喫煙物品又は無煙タバコ組成物で使用するためのタバコ組成物。
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