CA1068095A - Pyrrole-containing tobacco products - Google Patents
Pyrrole-containing tobacco productsInfo
- Publication number
- CA1068095A CA1068095A CA245,647A CA245647A CA1068095A CA 1068095 A CA1068095 A CA 1068095A CA 245647 A CA245647 A CA 245647A CA 1068095 A CA1068095 A CA 1068095A
- Authority
- CA
- Canada
- Prior art keywords
- tobacco
- flavor
- aroma
- carbon atoms
- formylpyrrol
- 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
- 235000019505 tobacco product Nutrition 0.000 title claims abstract description 17
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 title description 4
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims abstract description 43
- 241000208125 Nicotiana Species 0.000 claims abstract description 42
- 239000000796 flavoring agent Substances 0.000 claims abstract description 20
- 235000019634 flavors Nutrition 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003233 pyrroles Chemical class 0.000 abstract 1
- 239000000654 additive Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 235000019504 cigarettes Nutrition 0.000 description 9
- 230000000996 additive effect Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 4
- 230000000391 smoking effect Effects 0.000 description 4
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
- 235000019506 cigar Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000000779 smoke Substances 0.000 description 3
- OVBFMEVBMNZIBR-UHFFFAOYSA-N -2-Methylpentanoic acid Natural products CCCC(C)C(O)=O OVBFMEVBMNZIBR-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000002708 enhancing effect Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- -1 methylpyrrol-l-yl Chemical group 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 235000019260 propionic acid Nutrition 0.000 description 2
- ZSKGQVFRTSEPJT-UHFFFAOYSA-N pyrrole-2-carboxaldehyde Chemical compound O=CC1=CC=CN1 ZSKGQVFRTSEPJT-UHFFFAOYSA-N 0.000 description 2
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 229940005605 valeric acid Drugs 0.000 description 2
- KIZPSJJWBUYJBI-UHFFFAOYSA-N 2-(2-formylpyrrol-1-yl)-3-methylbutanoic acid Chemical compound CC(C)C(C(O)=O)N1C=CC=C1C=O KIZPSJJWBUYJBI-UHFFFAOYSA-N 0.000 description 1
- IFNRDWSKKNGFGN-UHFFFAOYSA-N 2-(2-formylpyrrol-1-yl)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)N1C=CC=C1C=O IFNRDWSKKNGFGN-UHFFFAOYSA-N 0.000 description 1
- NNFDHJQLIFECSR-UHFFFAOYSA-N 2-bromo-4-methylpentanoic acid Chemical compound CC(C)CC(Br)C(O)=O NNFDHJQLIFECSR-UHFFFAOYSA-N 0.000 description 1
- LDLGGVZKMRJHFZ-UHFFFAOYSA-N 3-(2-formylpyrrol-1-yl)butanoic acid Chemical compound OC(=O)CC(C)N1C=CC=C1C=O LDLGGVZKMRJHFZ-UHFFFAOYSA-N 0.000 description 1
- HHLWLLWBHBDZGK-UHFFFAOYSA-N 4-(2-formylpyrrol-1-yl)butanoic acid Chemical compound OC(=O)CCCN1C=CC=C1C=O HHLWLLWBHBDZGK-UHFFFAOYSA-N 0.000 description 1
- XCOHBIOUUWNJKW-UHFFFAOYSA-N 8-(2-butyl-5-formylpyrrol-1-yl)octanoic acid Chemical compound CCCCC1=CC=C(C=O)N1CCCCCCCC(O)=O XCOHBIOUUWNJKW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- WKNDIVOAKRQKED-UHFFFAOYSA-N methyl 2-(2-formylpyrrol-1-yl)-4-methylpentanoate Chemical compound COC(=O)C(CC(C)C)N1C=CC=C1C=O WKNDIVOAKRQKED-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000004533 oil dispersion Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000000135 prohibitive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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
- A24B15/28—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
- A24B15/36—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring
- A24B15/38—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom
- A24B15/385—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only nitrogen as hetero atom in a five-membered ring
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Manufacture Of Tobacco Products (AREA)
- Fats And Perfumes (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/566,083 US3996940A (en) | 1975-04-08 | 1975-04-08 | Tobacco product |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1068095A true CA1068095A (en) | 1979-12-18 |
Family
ID=24261405
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA245,647A Expired CA1068095A (en) | 1975-04-08 | 1976-02-13 | Pyrrole-containing tobacco products |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3996940A (enExample) |
| JP (1) | JPS51123899A (enExample) |
| BE (1) | BE840037A (enExample) |
| CA (1) | CA1068095A (enExample) |
| FR (1) | FR2306643A1 (enExample) |
| GB (1) | GB1485103A (enExample) |
| NL (1) | NL7603694A (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3150171B1 (fr) | 2023-06-26 | 2025-08-29 | Psa Automobiles Sa | Procédé et dispositif de mémorisation d’une nouvelle position latérale d’un système de maintien dans la voie |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL130041C (enExample) * | 1964-12-08 | |||
| US3529607A (en) * | 1968-09-05 | 1970-09-22 | Werner Richard Gotthard Luttic | Method of influencing the flavor of tobacco |
-
1975
- 1975-04-08 US US05/566,083 patent/US3996940A/en not_active Expired - Lifetime
-
1976
- 1976-02-13 CA CA245,647A patent/CA1068095A/en not_active Expired
- 1976-03-25 BE BE165567A patent/BE840037A/xx unknown
- 1976-04-06 JP JP51038678A patent/JPS51123899A/ja active Pending
- 1976-04-07 FR FR7610156A patent/FR2306643A1/fr active Granted
- 1976-04-08 GB GB14414/76A patent/GB1485103A/en not_active Expired
- 1976-04-08 NL NL7603694A patent/NL7603694A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NL7603694A (nl) | 1976-10-12 |
| US3996940A (en) | 1976-12-14 |
| FR2306643A1 (fr) | 1976-11-05 |
| FR2306643B3 (enExample) | 1979-01-05 |
| GB1485103A (en) | 1977-09-08 |
| BE840037A (fr) | 1976-07-16 |
| JPS51123899A (en) | 1976-10-28 |
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