US3389706A - Tobacco product - Google Patents

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Publication number
US3389706A
US3389706A US506863A US50686365A US3389706A US 3389706 A US3389706 A US 3389706A US 506863 A US506863 A US 506863A US 50686365 A US50686365 A US 50686365A US 3389706 A US3389706 A US 3389706A
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United States
Prior art keywords
tobacco
flavor
product
aroma
oxo
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Expired - Lifetime
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US506863A
Inventor
Joseph N Schumacher
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RJ Reynolds Tobacco Co
Original Assignee
RJ Reynolds Tobacco Co
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by RJ Reynolds Tobacco Co filed Critical RJ Reynolds Tobacco Co
Priority to US506863A priority Critical patent/US3389706A/en
Priority to GB3875468A priority patent/GB1155800A/en
Priority to GB3875668A priority patent/GB1156120A/en
Priority to GB3875568A priority patent/GB1156119A/en
Priority to GB3945266A priority patent/GB1154089A/en
Priority to BE687082D priority patent/BE687082A/xx
Priority to FR77037A priority patent/FR1493996A/en
Priority to DE19661792730 priority patent/DE1792730A1/en
Priority to DE19661792731 priority patent/DE1792731A1/en
Priority to NL6613408A priority patent/NL6613408A/xx
Priority to DE19661692941 priority patent/DE1692941A1/en
Priority to CH1382066A priority patent/CH482416A/en
Application granted granted Critical
Publication of US3389706A publication Critical patent/US3389706A/en
Priority to NL7214770A priority patent/NL7214770A/xx
Priority to NL7214769A priority patent/NL7214769A/xx
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/06—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms
    • C07C403/08—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by singly-bound oxygen atoms by hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C403/00—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone
    • C07C403/14—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms
    • C07C403/16—Derivatives of cyclohexane or of a cyclohexene or of cyclohexadiene, having a side-chain containing an acyclic unsaturated part of at least four carbon atoms, this part being directly attached to the cyclohexane or cyclohexene or cyclohexadiene rings, e.g. vitamin A, beta-carotene, beta-ionone having side-chains substituted by doubly-bound oxygen atoms not being part of —CHO groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/56—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds
    • C07C45/57—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom
    • C07C45/59—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds from heterocyclic compounds with oxygen as the only heteroatom in five-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/04—Saturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/12—Ketones containing more than one keto group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/20—Unsaturated compounds containing keto groups bound to acyclic carbon atoms
    • C07C49/203—Unsaturated compounds containing keto groups bound to acyclic carbon atoms with only carbon-to-carbon double bonds as unsaturation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/40—Radicals substituted by oxygen atoms
    • C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/74—Benzo[b]pyrans, hydrogenated in the carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • This invention relates to a tobacco product and has for an object the provision of a composition and process for improving the flavor and aroma of tobacco and tobacco smoke.
  • a further object of this invention is the provision of a process for enhancing or otherwise improving the flavor, aroma and other qualities of certain domestic, oriental, reconstituted or synthetic tobaccos which may be deficient in said flavor or aroma or other qualities.
  • An additional object of this invention is to provide a process of preparing a smoking tobacco or product which when smoked has an enhanced flavor or aroma.
  • a still further object of this invention is the provision of smoking products, such as cigarettes, cigars or pipe tobacco, and a process for forming same whereby the flavor and aroma before and during smoking are improved or enhanced.
  • a tobacco product is provided to which has been added or which has been treated with a small amount of 2,3,6,7,- 8,8a hexahydro 7 oxo 2,5,5,8a tetramethyl 5H 1- benzopyran (hereinafter called Compound I).
  • Compound I can be illustrated by the formula:
  • the material obtained was chromatographed, and 40 grams of a-ionone, 1.5 grams of 4-oxo-fi-ionone or also known as 4 (3 oxo 2,6,6 trimethyl 1 cyclohexen 1 yl)- 3 buten- 2 one, and 12 grams of 5-oxo-a-ionone were obtained as pure compounds.
  • the 5-oxo-a-ionone was recrystallized from pentane-ether solutions and melted at 7173 C. (lit. M.P. 6667).
  • keto-alcohol (III) was dissolved in 25 milliliters of benzene containing 0.2 gram of p-toluenesulphonic acid, and the resulting solution was refluxd one hour. The cooled solution was washed with water and with 5 percent sodium carbonate solution.
  • the tobacco additive of the invention when incorporated into tobacco products imparts an ionone flavor and aroma during smoking which many smokers consider to be desirable in smoking products.
  • the methods for defining or characterizing the quality of a flavor or aroma in the tobacco art are almost purely subjective and different smokers may define the same flavor quite differently.
  • the above indicated compound is added to tobacco or applied to a smoking article or its component parts in amounts of about 0.0001 to 1.0 percent by weight of the product.
  • the amount of additive is between about 0.01 and 0.5 percent by weight in order to provide a tobacco product having a desired flavor and aroma.
  • the additive may be incorporated at any step in the treatment of the tobacco but is preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes. Likewise, it will be apparent that only a portion of the tobacco need be treated and the thus treated tobacco may be blended with other tobaccos before the cigarettes or other smoking articles are formed. In such case the tobacco treated may have the additive in excess of the amounts above indicated so that when blended with other tobaccos the final product will have the percentage within the indicated range.
  • an aged flue-cured and shredded tobacco is sprayed with a 1% ethyl alcohol solution of 2,3,6,7,8,8ahexahydro-7-oxo-2,5,5,8a-tetramethyl-5H-1 benzopyran in an amount to provide a tobacco containing 0.1 percent by weight of the additive on a dry basis. Thereafter the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques. It has been found that the cigarette when prepared as indicated has a desired and pleasing flavor.
  • the additive falling within the scope of this invention may be applied to the tobacco by spraying, dipping or otherwise, utilizing suitable suspensions or solutions of the additive.
  • water or volatile organic solvents such as alcohol, ether, acetone, volatile hydrocarbons and the like, may be used as the carrying medium for the additive while it is being applied to the tobacco.
  • other fiavor and aroma-producing additives such as those disclosed in U.S. Patents Nos. 2,766,145, 2,905,575, 2,905,- 576, 2,978,365 and 3,034,211 may be incorporated into the tobacco with the additive of this invention.
  • While this invention is principally useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco, cigars or other tobacco products.
  • the compound may be added to certain tobacco substitutes of natural or synthetic origin and by the term tobacco as used throughout this specification is meant any composition intended for human consumption by smoking or otherwise, whether composed of tobacco plant parts or substitute materials or both.
  • the invention has been particularly described with reference to the addition of the compound directly to tobacco.
  • the compound may be applied to the paper of the cigarette or to the wrapper of a cigar. Also it may be incorporated into the filter tip, the packaging material or the seam paste em ployed for gluing the cigarette paper.
  • a tobacco product is provided which includes the specified additive and tobacco although in every instance the compound need not be admixed with the tobacco as above specifically described.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Manufacture Of Tobacco Products (AREA)

Description

United States Patent 3,389,706 TOBACCO PRODUCT Joseph N. Schumacher, Winston-Saiem, N.C., assignor to R. J. Reynolds Tobacco Company, Winston-Salem, N.C., a corporation of New Jersey No Drawing. Filed Nov. 8, 1965, Ser. No. 506,863 3 Claims. (Cl. 13117) This invention relates to a tobacco product and has for an object the provision of a composition and process for improving the flavor and aroma of tobacco and tobacco smoke.
It is well known in the tobacco art that the flavor and aroma of the tabacco product and the smoke from the tobacco are very important considerations in so far as the ultimate consumer is concerned. Considerable efforts are exertedby the manufacturers of tobacco products to provide a product that will be acceptable to the consumer, particularly as regards flavor and aroma characteristics. It has been the common practice in the tobacco industry to prepare blends of domestic and oriental tobaccos in order to provide smoking tobacco which has a pleasing flavor and aroma before and during smoking. However, such a procedure is costly and may at times become prohibitive in the event that certain types of tobacco may be in short supply. Accordingly, it is a further object of this invention to provide a new class of additive materials which when applied to the tobacco products improve and enhance the flavor and aroma of these products and the smoke emitted therefrom thereby increasing or enhancing the pleasure and other values that may be derived by the consumer from the use of these products.
A further object of this invention is the provision of a process for enhancing or otherwise improving the flavor, aroma and other qualities of certain domestic, oriental, reconstituted or synthetic tobaccos which may be deficient in said flavor or aroma or other qualities.
An additional object of this invention is to provide a process of preparing a smoking tobacco or product which when smoked has an enhanced flavor or aroma.
A still further object of this invention is the provision of smoking products, such as cigarettes, cigars or pipe tobacco, and a process for forming same whereby the flavor and aroma before and during smoking are improved or enhanced.
Further and additional objects will appear from the following description and the appended claims.
In accordance with one embodiment of this invention, a tobacco product is provided to which has been added or which has been treated with a small amount of 2,3,6,7,- 8,8a hexahydro 7 oxo 2,5,5,8a tetramethyl 5H 1- benzopyran (hereinafter called Compound I). Compound I can be illustrated by the formula:
A. SYNTHESIS AND PROPERTIES OF 2,3,6,7,8,8a- HEXAHYDRO 7 OX0 2,5,5,8a TETRAMETH- LY-SH-l-BENZOPYRAN (1) 5-OXO-zx-i0n0nfi or also known as 4-(4-oxo-2,6,6-trimethyl-2-cyclohexen-1-yl)-3-buten-2-one The method of V. Prelog and M. Osgan, Helv. Chim. Acta, 35, 986-92 (1952), or modifications of it, was used for the preparation of 5OXO-OL-lOnOl'l6. a-Ionone grams) was treated with t-butyl chromate in carbon tetrachloride (325 grams t-butyl alcohol, 220 grams chromic anhydride, 200 milliliters acetic acid, 30 milliliters acetic anhydride, and 2 liters carbon tetrachloride). The mixture was kept at 0 C. for 16 days in the dark, after which time it was worked up in the prescribed manner. The material obtained was chromatographed, and 40 grams of a-ionone, 1.5 grams of 4-oxo-fi-ionone or also known as 4 (3 oxo 2,6,6 trimethyl 1 cyclohexen 1 yl)- 3 buten- 2 one, and 12 grams of 5-oxo-a-ionone were obtained as pure compounds. The 5-oxo-a-ionone was recrystallized from pentane-ether solutions and melted at 7173 C. (lit. M.P. 6667).
(2) Rearrangement and cyclization of 5 oxo a ionone.Crude 5-oxo-a-ionone (25 grams) was dissolved in 100 milliliters of 1:1 methyl alcohol/water containing 8 grams of potassium hydroxide and allowed to stand overnight at room temperature. The solution was neutralized, diluted with water, extracted with ether, and the ether was removed in vacuo. The crude dione (II) was dissolved in 25 milliliters of ethanol and two grams of sodium borohydride were added. After standing two hours, the mixture was acidified, diluted with water, and extracted with ether. Removal of the ether in vacuo gave crude keto-alcohol (III).
The keto-alcohol (III) was dissolved in 25 milliliters of benzene containing 0.2 gram of p-toluenesulphonic acid, and the resulting solution was refluxd one hour. The cooled solution was washed with water and with 5 percent sodium carbonate solution. After removing the benzene in vacuo, the residue was distilled, yielding 1.2 grams of 2,3,6,7,8,8a-hexahydro-7-oxo-2,5,5,8a-tetramethyl-5H- l-benzopyran, boiling point 87-89/ 2 millimeters; nuclear magnetic resonance spectrum: u=8.87(3); 817(3); doulet 8.76(3); 851(3); 7.64(2); 7.42(2); 6.15(1); and 427(1).
It has been found that the tobacco additive of the invention when incorporated into tobacco products imparts an ionone flavor and aroma during smoking which many smokers consider to be desirable in smoking products. However, it is pointed out that the methods for defining or characterizing the quality of a flavor or aroma in the tobacco art are almost purely subjective and different smokers may define the same flavor quite differently.
In accordance with this invention, the above indicated compound is added to tobacco or applied to a smoking article or its component parts in amounts of about 0.0001 to 1.0 percent by weight of the product. Preferably the amount of additive is between about 0.01 and 0.5 percent by weight in order to provide a tobacco product having a desired flavor and aroma. However, the amount used will depend upon the amount of flavor and aroma desired and the particular compound or mixture thereof that is used. The additive may be incorporated at any step in the treatment of the tobacco but is preferably added after aging, curing and shredding and before the tobacco is formed into cigarettes. Likewise, it will be apparent that only a portion of the tobacco need be treated and the thus treated tobacco may be blended with other tobaccos before the cigarettes or other smoking articles are formed. In such case the tobacco treated may have the additive in excess of the amounts above indicated so that when blended with other tobaccos the final product will have the percentage within the indicated range.
In accordance with one specific embodiment of this invention, an aged flue-cured and shredded tobacco is sprayed with a 1% ethyl alcohol solution of 2,3,6,7,8,8ahexahydro-7-oxo-2,5,5,8a-tetramethyl-5H-1 benzopyran in an amount to provide a tobacco containing 0.1 percent by weight of the additive on a dry basis. Thereafter the alcohol is removed by evaporation and the tobacco is manufactured into cigarettes by the usual techniques. It has been found that the cigarette when prepared as indicated has a desired and pleasing flavor.
The additive falling within the scope of this invention may be applied to the tobacco by spraying, dipping or otherwise, utilizing suitable suspensions or solutions of the additive. Thus water or volatile organic solvents, such as alcohol, ether, acetone, volatile hydrocarbons and the like, may be used as the carrying medium for the additive while it is being applied to the tobacco. Also, other fiavor and aroma-producing additives, such as those disclosed in U.S. Patents Nos. 2,766,145, 2,905,575, 2,905,- 576, 2,978,365 and 3,034,211 may be incorporated into the tobacco with the additive of this invention.
While this invention is principally useful in the manufacture of cigarette tobacco, it is also suitable for use in connection with the manufacture of pipe tobacco, cigars or other tobacco products. Furthermore, the compound may be added to certain tobacco substitutes of natural or synthetic origin and by the term tobacco as used throughout this specification is meant any composition intended for human consumption by smoking or otherwise, whether composed of tobacco plant parts or substitute materials or both.
Also, the invention has been particularly described with reference to the addition of the compound directly to tobacco. However, it will be apparent that the compound may be applied to the paper of the cigarette or to the wrapper of a cigar. Also it may be incorporated into the filter tip, the packaging material or the seam paste em ployed for gluing the cigarette paper. Thus, a tobacco product is provided which includes the specified additive and tobacco although in every instance the compound need not be admixed with the tobacco as above specifically described.
While several particular embodiments of this invention are shown above, it will be understood, of course, that the invention is not to be limited thereto, since many modifications may be made, and it is contemplated, therefore, by the appended claims, to cover any such modifications ,as fall within the true spirit and scope of this invention.
I claim:
1. A tobacco product having added thereto 2,3,6,7,8, 8a hexahydro 7 OX0 2,5,5,8a tetramethyl 5H 1- benzopyran in an amount sufiicient to alter the flavor or aroma of the tobacco product.
2. The product recited in claim 1 where in the amount of the compound added to the product is between about 0.0001 and 1.0 percent by weight of the product.
3. The product recited in claim 1 wherein the amount of the compound added to the tobacco product is betweeen about 0.01 and 0.5 percent by weight of the product.
References Cited UNITED STATES PATENTS 3,185,708 5/1965 Mims. 3,217,716 11/1965 Roberts 13117 SAMUEL KOREN, Primary Examiner.
D. J. DONOHUE, Assistant Examiner.

Claims (1)

1. A TOBACCO PRODUCT HAVING ADDED THERETO 2,3,6,7,8, 8A - HEXAHYDRO - 7 - OXO - 2,5,5,8A - TETRAMETHYL - 5H - 1BENZOPYRAN IN AN AMOUNT SUFFICIENT TO ALTER THE FLAVOR OR AROMA OF THE TOBACCO PRODUCT.
US506863A 1965-11-08 1965-11-08 Tobacco product Expired - Lifetime US3389706A (en)

Priority Applications (14)

Application Number Priority Date Filing Date Title
US506863A US3389706A (en) 1965-11-08 1965-11-08 Tobacco product
GB3875468A GB1155800A (en) 1965-11-08 1966-09-02 Tobacco Products and Process for Preparing the same
GB3875668A GB1156120A (en) 1965-11-08 1966-09-02 Tobacco Products and Process for Preparing the same
GB3875568A GB1156119A (en) 1965-11-08 1966-09-02 Tobacco Products and process for preparing the same
GB3945266A GB1154089A (en) 1965-11-08 1966-09-02 Tobacco Products and Process for Preparing The Same.
BE687082D BE687082A (en) 1965-11-08 1966-09-19
FR77037A FR1493996A (en) 1965-11-08 1966-09-20 New tobacco products and process for their preparation
DE19661792730 DE1792730A1 (en) 1965-11-08 1966-09-22 USE OF ADDITIVES TO CHANGE THE FLAVOR OR FLAVOR OF A TOBACCO PRODUCT
DE19661792731 DE1792731A1 (en) 1965-11-08 1966-09-22 USE OF ADDITIVES TO CHANGE THE FLAVOR OR FLAVOR OF A TOBACCO PRODUCT
NL6613408A NL6613408A (en) 1965-11-08 1966-09-22
DE19661692941 DE1692941A1 (en) 1965-11-08 1966-09-22 Use of additives to change the taste or aroma of tobacco products
CH1382066A CH482416A (en) 1965-11-08 1966-09-26 Tobacco product of improved taste or aroma and process for making same
NL7214770A NL7214770A (en) 1965-11-08 1972-11-01
NL7214769A NL7214769A (en) 1965-11-08 1972-11-01

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US4071034A (en) * 1976-04-12 1978-01-31 International Flavors & Fragrances Inc. 2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the organoleptic properties of tobacco using one or more of said pyrans

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US3185708A (en) * 1962-03-07 1965-05-25 Reynolds Tobacco Co R Fused tricyclic lactones and their preparation
US3217716A (en) * 1963-11-14 1965-11-16 Reynolds Tobacco Co R Tobacco composition

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US3185708A (en) * 1962-03-07 1965-05-25 Reynolds Tobacco Co R Fused tricyclic lactones and their preparation
US3217716A (en) * 1963-11-14 1965-11-16 Reynolds Tobacco Co R Tobacco composition

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3746010A (en) * 1972-08-11 1973-07-17 Reynolds Tobacco Co R Tobacco product
US4071034A (en) * 1976-04-12 1978-01-31 International Flavors & Fragrances Inc. 2-Alkyl-4-phenyl-dihydropyrans and processes for augmenting the organoleptic properties of tobacco using one or more of said pyrans

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