US3563248A - Tobacco product - Google Patents
Tobacco product Download PDFInfo
- Publication number
- US3563248A US3563248A US825421A US3563248DA US3563248A US 3563248 A US3563248 A US 3563248A US 825421 A US825421 A US 825421A US 3563248D A US3563248D A US 3563248DA US 3563248 A US3563248 A US 3563248A
- Authority
- US
- United States
- Prior art keywords
- tobacco
- lactone
- tobacco product
- flavor
- product
- 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 - Lifetime
Links
- 235000019505 tobacco product Nutrition 0.000 title claims abstract description 16
- 241000208125 Nicotiana Species 0.000 claims description 32
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 32
- 150000002596 lactones Chemical class 0.000 claims description 13
- 125000000422 delta-lactone group Chemical group 0.000 abstract description 6
- NPKVOIPMYUHWLQ-UHFFFAOYSA-N 3-(2-hydroxycyclohexyl)propanoic acid Chemical compound OC1CCCCC1CCC(O)=O NPKVOIPMYUHWLQ-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000796 flavoring agent Substances 0.000 description 11
- 235000019634 flavors Nutrition 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 235000019504 cigarettes Nutrition 0.000 description 8
- 239000000779 smoke Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229930194542 Keto Natural products 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 150000004715 keto acids Chemical class 0.000 description 2
- -1 keto ester Chemical class 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 1
- 235000011130 ammonium sulphate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 235000019506 cigar Nutrition 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 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 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 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
- A24B15/40—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms
- A24B15/403—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a heterocyclic ring having only oxygen or sulfur as hetero atoms having only oxygen as hetero atoms
Definitions
- a tobacco product is described which includes a 3-(2-hydroxycyc1ohexyl) propionic acid, delta lactone having the structure Small amounts of this lactone enhance the flavor and aroma of the tobacco and improve the organoleptic qualities of the tobacco smoke.
- An object of this invention therefore is to provide a flavorant for tobacco which will improve the tobaccos flavor and aroma, and the tobacco smoke s organo leptic qualities.
- tobacco flavor is enhanced by the addition of a saturated lactone 3-(2-hydroxycyclohexyl) propionic acid, delta lactone having the chemical structure tion, the following example is given:
- a keto ester having the chemical structure is formed by reaction of cyclohexanone with methyl acrylate in a Michael condensation.
- a keto acid having the structure 0 ll -CH2CH2C 02H is formed from the aforesaid keto ester by saponification.
- a solution of 0.11 mole of the keto acid, 0.115 mole of sodium hydroxide and 0.05 mole of sodium borohydride in milliliters of methanol is stirred under a nitrogen atmosphere for 4 hoursat 0 C. This solution is then acidified, saturated with ammonium sulfate and thereafter extracted with ether.
- the resulting 3-(2-hydroxycyclohexyl) propionic acid, delta lactone is dissolved in ethyl alcohol and sprayed on shredded and blended domestic tobacco in amounts of 0.005 percent of the lactone by weight of the tobacco.
- cigarettes are made having a standard cellulose acetate filter.
- a second quantity of shredded and blended tobacco is sprayed with the same relative quantity of ethyl alcohol.
- cigarettes are made having a standard cellulose acetate filter. These cigarettes are used as the control for testing purposes.
- the 3-(2-hydroxycyclohexyl) propionic acid, delta lactone-treated cigarettes show a distinct improvement in the tobaccos flavor and aroma and the tobacco smoke s organoleptic properties.
- Procedures for making the above noted lactone contemplated by this invention are described in Vol. 62, pages 283287 of the Journal of the American Chemical Society, and Vol. 27, pages 4141 to 4146 of the Journal of Organic Chemistry.
- tobacco product as used herein are products made from tobacco such, for example, as cigarettes (either filtered or unfiltered), pipe tobacco and cigars.
- the lactone flavor additive may also be added to reconstituted tobacco or tobacco substitutes. It is also evident that the lactone contemplated by this invention may be added not only to the tobacco or filter tip section of a tobacco product but also to the cigarette paper wrapper or seam paste employed on the cigarette paper, or to the packaging material for the tobacco product. It is advantageous, however, that the lactone additive be included in the blended and shredded tobacco prior to its formation into a tobacco product.
- lIA tobacco product having added thereto a small amount of a lactone having the chemical structure such amount being sufficient to enhance the flavor or aroma of the tobacco product.
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US82542169A | 1969-05-16 | 1969-05-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3563248A true US3563248A (en) | 1971-02-16 |
Family
ID=25243976
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US825421A Expired - Lifetime US3563248A (en) | 1969-05-16 | 1969-05-16 | Tobacco product |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3563248A (enrdf_load_stackoverflow) |
| DE (1) | DE2023914A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1242368A (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996941A (en) * | 1975-05-08 | 1976-12-14 | R. J. Reynolds Tobacco Company | Tobacco product |
| US6557561B1 (en) * | 1997-10-24 | 2003-05-06 | Japan Tobacco Inc. | Cigarette paper having a flavorant which improves sidestream smoke smell, and a cigarette |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2766147A (en) * | 1954-07-26 | 1956-10-09 | Reynolds Tobacco Co R | Tobacco |
| US3217716A (en) * | 1963-11-14 | 1965-11-16 | Reynolds Tobacco Co R | Tobacco composition |
| US3342186A (en) * | 1964-08-07 | 1967-09-19 | Allied Chem | Aromatized tobaccos |
-
1969
- 1969-05-16 US US825421A patent/US3563248A/en not_active Expired - Lifetime
-
1970
- 1970-05-15 GB GB23777/70A patent/GB1242368A/en not_active Expired
- 1970-05-15 DE DE19702023914 patent/DE2023914A1/de active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2766147A (en) * | 1954-07-26 | 1956-10-09 | Reynolds Tobacco Co R | Tobacco |
| US3217716A (en) * | 1963-11-14 | 1965-11-16 | Reynolds Tobacco Co R | Tobacco composition |
| US3342186A (en) * | 1964-08-07 | 1967-09-19 | Allied Chem | Aromatized tobaccos |
Non-Patent Citations (1)
| Title |
|---|
| SHMUK, A.A, THE CHEMISTRY AND TECHNOLOGY OF TOBACCO, PISHCHEPROMIZDAT, MOSCOW VOL. III * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3996941A (en) * | 1975-05-08 | 1976-12-14 | R. J. Reynolds Tobacco Company | Tobacco product |
| US6557561B1 (en) * | 1997-10-24 | 2003-05-06 | Japan Tobacco Inc. | Cigarette paper having a flavorant which improves sidestream smoke smell, and a cigarette |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1242368A (en) | 1971-08-11 |
| DE2023914A1 (enrdf_load_stackoverflow) | 1970-11-19 |
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