US3545452A - Tobacco product including releasable flavorant - Google Patents
Tobacco product including releasable flavorant Download PDFInfo
- Publication number
- US3545452A US3545452A US780239A US3545452DA US3545452A US 3545452 A US3545452 A US 3545452A US 780239 A US780239 A US 780239A US 3545452D A US3545452D A US 3545452DA US 3545452 A US3545452 A US 3545452A
- Authority
- US
- United States
- Prior art keywords
- tobacco
- cis
- hexen
- tobacco product
- added
- 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 description 22
- 239000000796 flavoring agent Substances 0.000 title description 8
- 235000019634 flavors Nutrition 0.000 title description 7
- 241000208125 Nicotiana Species 0.000 description 52
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 52
- 235000019504 cigarettes Nutrition 0.000 description 19
- 239000000779 smoke Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 230000000391 smoking effect Effects 0.000 description 8
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000654 additive Substances 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 3
- 235000019506 cigar Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000203 mixture 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
- 244000025254 Cannabis sativa Species 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000002485 combustion reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000005022 packaging material Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000725 suspension 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
- A24B15/32—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances by acyclic compounds
Definitions
- Another object of the invention is the provision of smoking products, such as cigarettes, cigars, pipe tobacco, or tobacco smoke filters, having added thereto a releasable flavor additive which will impart a desirable fresh natural taste to the smoking product when smoked.
- our invention contemplates providing an organoleptically improved tobacco product having added thereto cis-3-hexen-l-0l, which imparts to the product the enhanced and desirable fresh flavor and aroma of natural tobacco. Cis-3-hexen-l-ol is readily transferred either from the filter section or the tobacco section into the smoke stream when the tobacco product is smoked.
- the flavor compound, cis-3-hexen-l-ol, which we employ to improve the organoleptic qualities of a tobacco product has an odor characteristic of fresh cut green grass. It may be added to a smoking, tobacco, which may consist of domestic tobacco, oriental tobacco, reconstituted tobacco or blends thereof, or it may be added'to the filter or to the paper wrapper.
- Cis-3-hexen- 1 -01 is an alcohol which is commercially available, is relatively nonvolatile at ambient temperatures but readily volatilizes and transfers to the tobacco smoke at temperatures substantially below the combustion temperature of burning tobacco. Also, cis-3-hexen-l-ol is sufflciently volatile when added to a tobacco smoke filter so that as the tobacco smoke passes through the filter it is readily. transferred thereto. Cis-3-hexenl-ol has the following physical properties: boiling point, 156C; d g? 0.846; 1.4803.
- the amount of cis-3-hexen-l-ol added to a tobacco product may vary greatly; however, a sufficient amountshould be used to achieve the desired organoleptic qualities for the smoking tobacco product when smoked.
- the levels of cis-3-hexen-l-ol added to a tobacco product, either to the filter or to the tobacco section may be as low as 0.001 percent based on the weight of the tobacco.
- the amount of cis-3- hexen-l-ol added to the tobacco product may be from about 0.001 percent to 0.1 percentbased on the weight of tobacco, preferably from about 0.005 percent to 0.05 percent, and more preferably from about 0.01 percent to 0.015 percent.
- Cis-3-hexen-l-ol may be incorporated at any step into the treatment of the tobacco but it is preferred that it be added after the tobacco has been cured, aged and shredded and just prior to the manufacture of the desired tobacco product, for example, cigarettes, cigars, pipe tobacco, or other smoking products. Also, it may be added to tobacco smoke filter material prior to forming the filter rod.
- the additive is conveniently dissolved in a solvent, such as ethyl alcohol, and applied to the tobacco by spraying, dipping or other methods of application generally employed for treating tobacco. Also, it may be sprayed onto the filtermaterial. Although solutions of this compound are preferred, suspensions thereof may be utilized.
- Other suitable solvents are, for example, acetone, ether, hexane, or the like. After treatment of the tobacco, or the filter, with this substance, substantially all of the solvent is evaporated therefrom prior to its manufacture into tobacco products.
- the following example illustrates the use of cis-3-hexenl-ol applied to filter cigarettes.
- the cigarettes were smoke tested and compared against control cigarettes without the cis-3- hexen-l-ol.
- EXAMPLE 1 Sufficient quantities of a solution of cis-3-hexen-l-ol in ethyl alcohol are sprayed on shredded and blended domestic tobacco to produce a 0.005 percent level by weight on the tobacco. After the ethyl alcohol is evaporated from the treated tobacco, cigarettes are made having a standard cellulose acetate filter.
- a second quantity of shredded and blended domestic tobac co is sprayed with the same relative quantity of ethyl alcohol. After the ethyl alcohol is evaporated from the tobacco, cigarettes are made having a standard cellulose acetate filter. These cigarettes are used as the control for testing purposes.
- Cigarettes were made in accordance with Example 1 in which cis-3-hexen-l-ol was added to the tobacco in the following levels: 0.01 percent and 0.015 percent by weight of tobacco.
- the results of an expert smoke panel test demonstrated a preference for the. treated cigarettes over the control cigarettes.
- the panel indicated that the cigarettes treated with cis-3-hexen-l-ol provided an improved smoking tobacco product exhibiting enhanced. and well balanced tobacco smoke characteristics generally associated with natural tobacco or tobacco blends.
- tobacco products as used herein are products made from tobacco, such as, for example, cigarettes, either filtered or unfiltered, pipe tobacco and cigars.
- the additive, cis-3-hexen-l-ol may be added to reconstituted tobacco or tobacco substitutes. It is also evident that cis-S-hexen-l-ol may be added not only to the tobacco or filter tip section of a tobacco product but also the cigarette paperwrapper or seam paste employed for gluing the cigarette paper, or to the. packaging material for the tobacco product. It is preferred, however, that the additive, cis-3- hexen-l-ol, be added to the blended and shredded tobacco prior'to its formation into a tobacco product.
- a tobacco product having added thereto a sufficient amount of cis-3-hexen-l-ol up to about 0.1 percent by weight of the tobacco so that when the tobacco product is smoked, the tobacco smoke has imparted thereto an enhanced fresh natural of tobacco.
Description
United States Patent [72] Inventors Robert R. Johnson;
Ezra Dempsey Alford, Lousiville, Ky. 780,239
Nov. 29, 1968 Dec. 8, 1970 1 Brown & Williamson Tobacco Corporation Louisville, Ky.
a corporation of Delaware [21 Appl. No. [22] Filed [45] Patented [73] Assignee [52] US. Cl. 131/17,
131/9,131/15,131/l44,131/261 [51] 1nt.Cl. ..A24b 15/04 [50] Field of Search 99/ 140, (Chem Abstracts); 131/144, 10, 17, 9, 261(A) [56] References Cited OTHER REFERENCES Attaway, .1.A., R.W. Wolford, G.E. Alberding, and G. .1. Edwards. Identification of Alcohols and volatile organic acids from natural orange essence. Journal of Agricultural Food Chemistry, 12(2): 118-121 (1964).
Primary ExaminerSamuel Koren Assistant Examiner-G. M. Yahwak Attorney-l(ane, Dalsimer, Kane, Sullivan and Smith ABSTRACT: An organoleptically improved tobacco product having added thereto cis-3-hexen-l-ol.
tobacco.
1 TOBACCO PRODUCT INCLUDING RELEASABLE FLAVORANT BACKGROUND OF THE INVENTION Many substances are known which when added to a tobacco product improve the flavor and aroma of the tobacco smoke, for example, menthol. Many of these substances, such as menthol, are highly volatile and impart to the tobacco smoke a flavor and aroma generally characteristic of the substance added thereto. Much time and effort are devoted by the tobacco industry to develop additives which, when applied to a tobacco product, will enhance the natural flavor of the tobacco as well as improve the organoleptic qualities of the tobacco which will enhance the tobacco aroma, as well as the flavor characteristics of the tobacco product made therefrom. Also, it is an object of the present invention to provide a smoking tobacco product having a material added to the tobacco which will readily transfer to the tobacco smoke and pass through a filter element even of the high filtration type so that the natural flavor qualities of the tobacco smoke are enhanced.
Another object of the invention is the provision of smoking products, such as cigarettes, cigars, pipe tobacco, or tobacco smoke filters, having added thereto a releasable flavor additive which will impart a desirable fresh natural taste to the smoking product when smoked.
SUMMARY OF THE INVENTION In general, our invention contemplates providing an organoleptically improved tobacco product having added thereto cis-3-hexen-l-0l, which imparts to the product the enhanced and desirable fresh flavor and aroma of natural tobacco. Cis-3-hexen-l-ol is readily transferred either from the filter section or the tobacco section into the smoke stream when the tobacco product is smoked. The organoleptic qualities of cis-3-hexen-l-ol, particularly when transferred to the tobacco smoke, impart a desirable fresh flavor and aroma of DETAILED DESCRIPTION OF THE INVENTION The flavor compound, cis-3-hexen-l-ol, which we employ to improve the organoleptic qualities of a tobacco product has an odor characteristic of fresh cut green grass. It may be added to a smoking, tobacco, which may consist of domestic tobacco, oriental tobacco, reconstituted tobacco or blends thereof, or it may be added'to the filter or to the paper wrapper.
Cis-3-hexen- 1 -01 is an alcohol which is commercially available, is relatively nonvolatile at ambient temperatures but readily volatilizes and transfers to the tobacco smoke at temperatures substantially below the combustion temperature of burning tobacco. Also, cis-3-hexen-l-ol is sufflciently volatile when added to a tobacco smoke filter so that as the tobacco smoke passes through the filter it is readily. transferred thereto. Cis-3-hexenl-ol has the following physical properties: boiling point, 156C; d g? 0.846; 1.4803.
The amount of cis-3-hexen-l-ol added to a tobacco product may vary greatly; however, a sufficient amountshould be used to achieve the desired organoleptic qualities for the smoking tobacco product when smoked. We have found that the levels of cis-3-hexen-l-ol added to a tobacco product, either to the filter or to the tobacco section, may be as low as 0.001 percent based on the weight of the tobacco. The amount of cis-3- hexen-l-ol added to the tobacco product may be from about 0.001 percent to 0.1 percentbased on the weight of tobacco, preferably from about 0.005 percent to 0.05 percent, and more preferably from about 0.01 percent to 0.015 percent.
Cis-3-hexen-l-ol may be incorporated at any step into the treatment of the tobacco but it is preferred that it be added after the tobacco has been cured, aged and shredded and just prior to the manufacture of the desired tobacco product, for example, cigarettes, cigars, pipe tobacco, or other smoking products. Also, it may be added to tobacco smoke filter material prior to forming the filter rod. The additive is conveniently dissolved in a solvent, such as ethyl alcohol, and applied to the tobacco by spraying, dipping or other methods of application generally employed for treating tobacco. Also, it may be sprayed onto the filtermaterial. Although solutions of this compound are preferred, suspensions thereof may be utilized. Other suitable solvents are, for example, acetone, ether, hexane, or the like. After treatment of the tobacco, or the filter, with this substance, substantially all of the solvent is evaporated therefrom prior to its manufacture into tobacco products.
The following example illustrates the use of cis-3-hexenl-ol applied to filter cigarettes. The cigarettes were smoke tested and compared against control cigarettes without the cis-3- hexen-l-ol.
EXAMPLE 1 Sufficient quantities of a solution of cis-3-hexen-l-ol in ethyl alcohol are sprayed on shredded and blended domestic tobacco to produce a 0.005 percent level by weight on the tobacco. After the ethyl alcohol is evaporated from the treated tobacco, cigarettes are made having a standard cellulose acetate filter.
A second quantity of shredded and blended domestic tobac co is sprayed with the same relative quantity of ethyl alcohol. After the ethyl alcohol is evaporated from the tobacco, cigarettes are made having a standard cellulose acetate filter. These cigarettes are used as the control for testing purposes.
Both the cis-3-hexen-l-ol treated cigarettes and the control cigarettes were smoked by an expert smoke panel. The results of the smoke panel test demonstrated a preference for the cis- 3-hexen- 1 -ol treated cigarettes over the control cigarettes.
Cigarettes were made in accordance with Example 1 in which cis-3-hexen-l-ol was added to the tobacco in the following levels: 0.01 percent and 0.015 percent by weight of tobacco. The results of an expert smoke panel test demonstrated a preference for the. treated cigarettes over the control cigarettes. The panel indicated that the cigarettes treated with cis-3-hexen-l-ol provided an improved smoking tobacco product exhibiting enhanced. and well balanced tobacco smoke characteristics generally associated with natural tobacco or tobacco blends.
It should be understood that the term tobacco products as used herein are products made from tobacco, such as, for example, cigarettes, either filtered or unfiltered, pipe tobacco and cigars. Also, the additive, cis-3-hexen-l-ol, may be added to reconstituted tobacco or tobacco substitutes. It is also evident that cis-S-hexen-l-ol may be added not only to the tobacco or filter tip section of a tobacco product but also the cigarette paperwrapper or seam paste employed for gluing the cigarette paper, or to the. packaging material for the tobacco product. It is preferred, however, that the additive, cis-3- hexen-l-ol, be added to the blended and shredded tobacco prior'to its formation into a tobacco product.
It is apparent that a wide variation in the amount of cis-3- hexen-l-ol. employedto treat a smoking tobacco may be made without departing from the invention herein as defined in the appended claims.
We claim:
1. A tobacco product having added thereto a sufficient amount of cis-3-hexen-l-ol up to about 0.1 percent by weight of the tobacco so that when the tobacco product is smoked, the tobacco smoke has imparted thereto an enhanced fresh natural of tobacco.
2. A tobacco product as set forth in claim 1 wherein the amount of cis-3-hexen-l-ol is between about 0.001 percent to 0.1 percent by weight of the tobacco.
4. A tobacco product as set forth in claim 1 wherein the amount of cis-3-hexen-l-ol is between about 0.01 percent to 0.015 percent by weight of the tobacco.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US78023968A | 1968-11-29 | 1968-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3545452A true US3545452A (en) | 1970-12-08 |
Family
ID=25119028
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US780239A Expired - Lifetime US3545452A (en) | 1968-11-29 | 1968-11-29 | Tobacco product including releasable flavorant |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3545452A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4827012A (en) * | 1988-02-23 | 1989-05-02 | Basf Corporation | Oxo-ionol carbonates |
| US4992106A (en) * | 1988-02-23 | 1991-02-12 | Basf Corporation | Novel oxo-ionol carbonates useful as tobacco flavorants |
| US20130336901A1 (en) * | 2007-07-25 | 2013-12-19 | Philip Morris Usa Inc. | Flavorant ester salts of polycarboxylic acids and methods for immobilizing and delivering flavorants containing hydroxyl groups |
-
1968
- 1968-11-29 US US780239A patent/US3545452A/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4827012A (en) * | 1988-02-23 | 1989-05-02 | Basf Corporation | Oxo-ionol carbonates |
| US4992106A (en) * | 1988-02-23 | 1991-02-12 | Basf Corporation | Novel oxo-ionol carbonates useful as tobacco flavorants |
| US20130336901A1 (en) * | 2007-07-25 | 2013-12-19 | Philip Morris Usa Inc. | Flavorant ester salts of polycarboxylic acids and methods for immobilizing and delivering flavorants containing hydroxyl groups |
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