JP7436517B2 - 液体たばこ抽出物、これを作製するための方法およびこれを備えたエアロゾル発生物品 - Google Patents
液体たばこ抽出物、これを作製するための方法およびこれを備えたエアロゾル発生物品 Download PDFInfo
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- JP7436517B2 JP7436517B2 JP2021568742A JP2021568742A JP7436517B2 JP 7436517 B2 JP7436517 B2 JP 7436517B2 JP 2021568742 A JP2021568742 A JP 2021568742A JP 2021568742 A JP2021568742 A JP 2021568742A JP 7436517 B2 JP7436517 B2 JP 7436517B2
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- Prior art keywords
- tobacco extract
- liquid
- weight percent
- liquid tobacco
- micrograms
- 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.)
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- 235000002637 Nicotiana tabacum Nutrition 0.000 title claims description 990
- 241000208125 Nicotiana Species 0.000 title claims description 989
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- 238000000034 method Methods 0.000 title claims description 43
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 315
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 312
- 229960002715 nicotine Drugs 0.000 claims description 312
- 239000000203 mixture Substances 0.000 claims description 265
- 238000000605 extraction Methods 0.000 claims description 178
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 126
- XPFVYQJUAUNWIW-UHFFFAOYSA-N furfuryl alcohol Chemical compound OCC1=CC=CO1 XPFVYQJUAUNWIW-UHFFFAOYSA-N 0.000 claims description 126
- 150000001875 compounds Chemical class 0.000 claims description 109
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 99
- PSQYTAPXSHCGMF-BQYQJAHWSA-N β-ionone Chemical compound CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 claims description 94
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- 239000007858 starting material Substances 0.000 claims description 88
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- 239000003125 aqueous solvent Substances 0.000 claims description 61
- INAXVXBDKKUCGI-UHFFFAOYSA-N 4-hydroxy-2,5-dimethylfuran-3-one Chemical compound CC1OC(C)=C(O)C1=O INAXVXBDKKUCGI-UHFFFAOYSA-N 0.000 claims description 56
- POIARNZEYGURDG-FNORWQNLSA-N beta-damascenone Chemical compound C\C=C\C(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-FNORWQNLSA-N 0.000 claims description 50
- POIARNZEYGURDG-UHFFFAOYSA-N beta-damascenone Natural products CC=CC(=O)C1=C(C)C=CCC1(C)C POIARNZEYGURDG-UHFFFAOYSA-N 0.000 claims description 50
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 50
- 238000010438 heat treatment Methods 0.000 claims description 50
- 229930007850 β-damascenone Natural products 0.000 claims description 50
- SFEOKXHPFMOVRM-UHFFFAOYSA-N (+)-(S)-gamma-ionone Natural products CC(=O)C=CC1C(=C)CCCC1(C)C SFEOKXHPFMOVRM-UHFFFAOYSA-N 0.000 claims description 47
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 40
- UNYNVICDCJHOPO-UHFFFAOYSA-N sotolone Chemical compound CC1OC(=O)C(O)=C1C UNYNVICDCJHOPO-UHFFFAOYSA-N 0.000 claims description 40
- JZBCTZLGKSYRSF-UHFFFAOYSA-N 2-Ethyl-3,5-dimethylpyrazine Chemical compound CCC1=NC=C(C)N=C1C JZBCTZLGKSYRSF-UHFFFAOYSA-N 0.000 claims description 38
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 36
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 35
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 34
- FLAQQSHRLBFIEZ-UHFFFAOYSA-N N-Methyl-N-nitroso-4-oxo-4-(3-pyridyl)butyl amine Chemical compound O=NN(C)CCCC(=O)C1=CC=CN=C1 FLAQQSHRLBFIEZ-UHFFFAOYSA-N 0.000 claims description 32
- ZJOFAFWTOKDIFH-UHFFFAOYSA-N 3-(1-nitroso-3,6-dihydro-2h-pyridin-2-yl)pyridine Chemical compound O=NN1CC=CCC1C1=CC=CN=C1 ZJOFAFWTOKDIFH-UHFFFAOYSA-N 0.000 claims description 28
- XKABJYQDMJTNGQ-VIFPVBQESA-N n-nitrosonornicotine Chemical compound O=NN1CCC[C@H]1C1=CC=CN=C1 XKABJYQDMJTNGQ-VIFPVBQESA-N 0.000 claims description 28
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 claims description 28
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- PSINWXIDJYEXLO-UHFFFAOYSA-N 2,3-Diethyl-5-methylpyrazine Chemical compound CCC1=NC=C(C)N=C1CC PSINWXIDJYEXLO-UHFFFAOYSA-N 0.000 claims description 21
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 claims description 20
- 239000005770 Eugenol Substances 0.000 claims description 20
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 claims description 20
- 229960002217 eugenol Drugs 0.000 claims description 20
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 20
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 claims description 20
- 235000012141 vanillin Nutrition 0.000 claims description 20
- 239000001363 2-ethyl-3,5-dimethylpyrazine Substances 0.000 claims description 19
- BGVBGAIWXAXBLP-UHFFFAOYSA-N 3-Methyl-2,4-nonanedione Chemical compound CCCCCC(=O)C(C)C(C)=O BGVBGAIWXAXBLP-UHFFFAOYSA-N 0.000 claims description 19
- WLAMNBDJUVNPJU-BYPYZUCNSA-N 2-Methylbutanoic acid Natural products CC[C@H](C)C(O)=O WLAMNBDJUVNPJU-BYPYZUCNSA-N 0.000 claims description 17
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 claims description 17
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 17
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 14
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 14
- 239000001087 glyceryl triacetate Substances 0.000 claims description 14
- 235000013773 glyceryl triacetate Nutrition 0.000 claims description 14
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 14
- 229960002622 triacetin Drugs 0.000 claims description 14
- 239000000463 material Substances 0.000 description 82
- 239000002904 solvent Substances 0.000 description 60
- 239000000796 flavoring agent Substances 0.000 description 55
- 239000000443 aerosol Substances 0.000 description 52
- 235000019634 flavors Nutrition 0.000 description 45
- 239000000499 gel Substances 0.000 description 38
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 27
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
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- BXYPVKMROLGXJI-UHFFFAOYSA-N N'-Nitrosoanabasine Chemical compound O=NN1CCCCC1C1=CC=CN=C1 BXYPVKMROLGXJI-UHFFFAOYSA-N 0.000 description 16
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 16
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- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 14
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- 150000007524 organic acids Chemical class 0.000 description 13
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- 239000011261 inert gas Substances 0.000 description 12
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- 239000004615 ingredient Substances 0.000 description 10
- 241000894007 species Species 0.000 description 10
- 229910021529 ammonia Inorganic materials 0.000 description 9
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- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
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- A24B15/10—Chemical features of tobacco products or tobacco substitutes
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- A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
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- A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
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- A24B15/18—Treatment of tobacco products or tobacco substitutes
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- A—HUMAN NECESSITIES
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- A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
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Description
火力乾燥ブライトたばこ材料からたばこ出発材料を調製する。たばこ材料を、2.5ミリメートル×2.5ミリメートルの寸法を有するたばこ断片を形成するように切断し、たばこ断片を、圧縮することなく、抽出チャンバーに装填する。たばこ出発材料を、抽出チャンバー内で3時間の間摂氏130度の温度に加熱する。加熱中、窒素の流れが、約40リットル/分の流量で抽出チャンバーを通過する。
本実施例は、摂氏130度の温度で3時間の別個の抽出プロセスから得られた二つの濃縮たばこ抽出物を提供し、各プロセス後、液体たばこ抽出物の水分レベルをおよそ6パーセントに低減するための乾燥工程が続く。両方の液体たばこ抽出物は、液体たばこ抽出物の重量に基づいて0.2重量パーセントを超えるニコチンを含有する。さらに、両方の液体たばこ抽出物において、(β-イオノン+β-ダマセノン)対(フェノール)の重量比は、0.25を超える。
実施例2aは、火力乾燥ブライトたばこ材料に由来する濃縮たばこ抽出物に関する。実施例2aの液体たばこ抽出物の含有量は以下の通りである。
・ニコチン:0.53%w/w
・プロピレングリコール:91.8%w/w
・水:6.3%w/w
・残り(以下の表1に詳述される風味剤を含む):1.57%w/w
実施例2bは、バーレー種たばこ材料に由来する濃縮たばこ抽出物に関する。実施例2bの液体たばこ抽出物の含有量は以下の通りである。
・ニコチン:1.82%w/w
・プロピレングリコール:89.6%w/w
・水:5.7%w/w
・残り(以下の表1に詳述される風味剤を含む):2.88%w/w
本実施例は、摂氏130度の温度で3時間の別個の抽出プロセスから得られた三つの濃縮たばこ抽出物を提供し、それぞれ、液体たばこ抽出物の水分レベルをおよそ12.5パーセントに低減するための乾燥工程が続く。これらの全ての液体たばこ抽出物は、液体たばこ抽出物の重量に基づいて0.2重量パーセントを超えるニコチンを含有する。さらに、これらの液体たばこ抽出物において、(β-イオノン+β-ダマセノン)対(フェノール)の重量比は、0.25を超える。
実施例3aは、オリエンタル種ブライトたばこ材料に由来する濃縮たばこ抽出物に関する。実施例3aの濃縮たばこ抽出物の含有量は以下の通りである。
・ニコチン:0.4%w/w
・プロピレングリコール:84%w/w
・酢酸:1.0%w/w
・水:12.5%w/w
・残り(風味剤を含む):2.1%w/w
実施例3bは、火力乾燥ブライトたばこ材料に由来する濃縮たばこ抽出物に関する。実施例3bの濃縮たばこ抽出物の含有量は以下の通りである。
・ニコチン:1.2%w/w
・プロピレングリコール:84%w/w
・酢酸:1.0%w/w
・水:12.5%w/w
・残り(風味剤を含む):1.3%w/w
実施例3cは、バーレー種たばこ材料に由来する濃縮たばこ抽出物に関する。実施例3cの濃縮たばこ抽出物の含有量は以下の通りである。
・ニコチン:2.6%w/w
・プロピレングリコール:84%w/w
・酢酸:0.5%w/w
・水:12.5%w/w
・残り(風味剤を含む):0.4%w/w
実施例1の液体たばこ抽出物を乾燥プロセスで濃縮して、液体たばこ抽出物の水分レベルをおよそ15パーセントに低減した。
実施例5は、ゲルの形態のニコチン組成物に関する。ゲルニコチン組成物は、実施例1の液体たばこ抽出物から形成される。ゲルニコチン組成物の含有量は以下の通りである。
・実施例1の液体たばこ抽出物:99.0%w/w
・寒天:1.0%w/w
火力乾燥ブライトたばこ材料(6A)、バーレー種たばこ材料(6B)、およびオリエント種たばこ材料(6C)それぞれから本発明による三つのたばこ出発材料を調製する。
火力乾燥ブライトたばこ材料(CE1、CE2)から二つのたばこ出発材料を調製する。バーレー種たばこ材料(CE3、CE4)から二つのさらなるたばこ出発材料を調製する。四つの出発たばこ材料のそれぞれを切断して、2.5ミリメートル×2.5ミリメートルの寸法を有するたばこ断片を形成する。
Claims (15)
- 液体たばこ抽出物であって、非水性溶媒、前記液体たばこ抽出物の重量に基づいて少なくとも0.2重量パーセントのニコチン、および0.25を超える(β-イオノン+β-ダマセノン)対(フェノール)の重量比を含む、液体たばこ抽出物。
- 水をさらに含み、前記液体たばこ抽出物が、前記液体たばこ抽出物の前記重量に基づいて20重量パーセントを超える水を含む、請求項1に記載の液体たばこ抽出物。
- 前記液体たばこ抽出物が、前記液体たばこ抽出物の前記重量に基づいて少なくとも約40重量パーセントの水、好ましくは前記液体たばこ抽出物の前記重量に基づいて40重量パーセント~70重量パーセントの水を含む、請求項2に記載の液体たばこ抽出物。
- 水をさらに含み、前記液体たばこ抽出物が、濃縮たばこ抽出物の重量に基づいて、約20重量パーセント以下の水、好ましくは8重量パーセント~15重量パーセントの水を含む前記濃縮たばこ抽出物である、請求項1に記載の液体たばこ抽出物。
- (β-イオノン+β-ダマセノン)対(フェノール)の前記重量比が、0.5を超え、より好ましくは1を超え、なおより好ましくは1.5を超え、最も好ましくは2を超える、例えば、2~10または2~5である、請求項1~4のいずれか一項に記載の液体たばこ抽出物。
- 前記液体たばこ抽出物が、前記液体たばこ抽出物の前記重量に基づいて、0.4重量パーセント~3.6重量パーセントのニコチンを含む、請求項1~5のいずれか一項に記載の液体たばこ抽出物。
- 1.5を超える(β-イオノン+β-ダマセノン)対(4-(メチルニトロソアミノ)-1-(3-ピリジル)-1-ブタノン+(R,S)-N-ニトロソアナタビン+(R,S)-N-ニトロソアナバシン+N-ニトロソノルニコチン+((2-フランメタノール)/600))の重量比をさらに含む、請求項1~6のいずれか一項に記載の液体たばこ抽出物。
- 前記液体たばこ抽出物が、バーレー種たばこおよびブライトたばこに由来する、請求項1~7のいずれかに記載の液体たばこ抽出物。
- 前記ブライトたばこが、オリエント種たばこおよび火力乾燥たばこのうちの一つ以上である、請求項8に記載の液体たばこ抽出物。
- 前記非水性溶媒が、グリセリン、プロピレングリコール、トリアセチン、1,3-プロパンジオール、またはそれらの混合物である、請求項1~9のいずれかに記載の液体たばこ抽出物。
- フラネオール、2,3-ジエチル-5-メチルピラジン、酢酸、バニリン、2-エチル-3,5-ジメチルピラジン、2-メチルブタン酸、3-メチルブタン酸、3-メチル-2,4-ノナンジオン、2-メトキシフェノール、2-フェニルエタノール、オイゲノール、およびソトロンのうちの一つ以上をさらに含む、請求項1~10のいずれかに記載の液体たばこ抽出物。
- 前記液体たばこ抽出物が、前記液体たばこ抽出物1グラム当たり少なくとも300マイクログラムの酢酸を含む、請求項1~11のいずれかに記載の液体たばこ抽出物。
- カートリッジであって、
ニコチン組成物であって、請求項1~12のいずれかの液体たばこ抽出物を含むニコチン組成物、を含む、カートリッジ。 - 請求項1~12のいずれかに記載の液体たばこ抽出物を調製する方法であって、
たばこ出発材料を摂氏100度~摂氏160度の抽出温度で少なくとも90分間加熱する工程と、
前記加熱工程中に、前記たばこ出発材料から放出される揮発性化合物を非水性溶媒中で捕捉して、収集された揮発性化合物を形成する工程と、
前記収集された揮発性化合物を含む液体たばこ抽出物を形成する工程と、
を含む方法。 - 前記液体たばこ抽出物が、水をさらに含み、前記方法が、
前記液体たばこ抽出物を乾燥させて濃縮たばこ抽出物を得ることをさらに含む、請求項14に記載の方法。
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HUE062528T2 (hu) | 2023-11-28 |
EP3979820B1 (en) | 2023-08-02 |
AU2020288848A1 (en) | 2021-08-19 |
US20220240563A1 (en) | 2022-08-04 |
JP2022534870A (ja) | 2022-08-04 |
PL3979820T3 (pl) | 2024-01-15 |
MX2021014464A (es) | 2022-01-06 |
IL288435A (en) | 2022-01-01 |
ES2954965T3 (es) | 2023-11-27 |
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