US3762423A - Methyl trans-2-isopropyl-5-methyl-3-hexenoate and derivatives thereof as tobacco flavorants - Google Patents
Methyl trans-2-isopropyl-5-methyl-3-hexenoate and derivatives thereof as tobacco flavorants Download PDFInfo
- Publication number
- US3762423A US3762423A US00286915A US3762423DA US3762423A US 3762423 A US3762423 A US 3762423A US 00286915 A US00286915 A US 00286915A US 3762423D A US3762423D A US 3762423DA US 3762423 A US3762423 A US 3762423A
- Authority
- US
- United States
- Prior art keywords
- methyl
- trans
- isopropyl
- tobacco
- hexenoate
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
- A23L27/2024—Aliphatic compounds having oxygen as the only hetero atom
-
- 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
- This invention relates to novel unsaturated acids, esters, alcohols, aldehydes and ketones having utility as flavorants. More particularly, this invention is concerned with compounds containing the trans-2,6- dimethyl-3-hepten-5-yl group which have utility as additives to modify the taste of tobacco.
- radical X may be further represented by the radicals wherein R is hydrogen, lower alkyl, hydroxy or lower alkoxy, or
- the compound wherein X is hydroxymethyl, i.e. trans-2-isopropyl-5-methyl-3-hexenol, (C) can be obtained by reduction of, e.g., methyl trans-2-isopropyl-5- methyl-3-hexenoate.
- the preferred method of reduction is treatment of the ester by an ether solution of lithium aluminum hydride.
- Esters of the alcohol may be obtained via conventional techniques.
- the product in which X is formyl, trans-2-isopropyl- 5-methyl-3-hexenal, is obtained by oxidation of the corresponding alcohol (C), preferably by a solution of chromic acid-pyridine complex in methylene chloride solution.
- This product can be isolated and purified by gas-liquid partition chromatography.
- trans-Z-isopropyl-S-methyl-3-hexenal (D) Treatment of trans-Z-isopropyl-S-methyl-3-hexenal (D) with an ethereal solution of methyl lithium produces trans-3-isopropyl-6-methyl-4-hepten-2-ol, which can be isolated and puri-fied by gas-liquid partition chromatography.
- other a -hydroxyalkyl derivatives can be obtained through the use of other lower alkyl'lithium compounds. All of the alcohols can be converted to their lower acyl esters in known manner.
- the compounds of this invention are usefulto modify the flavor of tobacco products, and are-especially useful as cigarette flavorants. They may be applied to tobacco or reconstituted tobaccosheet by spraying in a suitable solvent such as ethanol, propylene glycol, glycerine, or casing solution, by dipping into a solution containing the appropriate products, or by incorporation into a flavor formulation normally applied to tobacco or reconstituted tobacco sheet.
- a suitable solvent such as ethanol, propylene glycol, glycerine, or casing solution
- concentrations normally will be in the range of from about 0.001 to about 0.01 weight per cent, based upon the weight of the tobacco or reconstituted tobacco sheet, although higher and lower concentrations may be employed if desired.
- EXAMPLE Vl Aliquots of 10 ;/.l. of a solution of 10 mg. of each of the products of Examples l-V dissolved in 1 ml. of percent ethanol were injected uniformly along a path of 55 mm. length in experimental cigarettes manufactured from a commercial blend of tobaccos. The solvent was removed from each cigarette by evaporation at room temperature.
- the smoke and flavor characteristics of each sample were evaluated by an experienced flavor panel.
- the samples were compared to control cigarettes prepared identically to the sample cigarettes but without the flavor additives.
- Cigarettes prepared as described above containing methyl trans-2-isopropyl-5-methyl-3-hexenoate produced smoke which exhibited increased sweetness and fullness and enhanced fragrance and tobacco character.
- Cigarettes treated with trans-2-isopropyl-5-methyl-3- hexen-l-ol produced smoke exhibiting an increase in green character and a slight increase in tobacco character.
- trans-2-isopropyl-5-methyl-3-hexenal (Example [11) treated cigarettes produced a smoke flavor described as weedy green and burnt woody with a slight increase in Turkish character.
- Cigarettes containing trans-3-isopropyl-6methyl-4- hepten-2-one produced a smoke flavor with increased green and bitter'character and an increase in natural sweetness.
- a tobacco composition including at least one compound of the formula:
- X l (CllahUllCll CllUllC(011 wherein X is an oxygen-containing radical of the formula wherein R is hydrogen, lower alkyl, hydroxy or lower alkoxy, R is hydrogen or lower acyl, and R" is hydrogen or lower alkyl wherein the amount of said comhydroxymethyl.
- a tobacco smoking article including a tobacco composition according to claim 3.
- l III UNITED STATES, PATENT OFFICE v CERTIFICATE OF CORRECTION Patent No. '3,762 l23 I Dated 10/2/73 lnventofls) Melvyn T. Simpson Albert H- Warfie'ld and Andrew G. Kallianos It is certified that error appears in the above-identified patent and that said Letters Patent are hereby corrected as shown below:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nutrition Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Manufacture Of Tobacco Products (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (8)
- 2. A composition according to claim 1 wherein X is carbomethoxy, carboxy, hydroxymethyl, formyl, Alpha -hydroxyethyl or acetyl.
- 3. A composition according to claim 1 wherein X is carbomethoxy.
- 4. A composition according to claim 1 wherein X is carboxyl.
- 5. A composition according to claim 1 wherein X is hydroxymethyl.
- 6. A composition according to claim 1 wherein X is formyl.
- 7. A composition according to claim 1 wherein X is Alpha -hydroxyethyl.
- 8. A composition according to claim 1 wherein X is acetyl.
- 9. A tobacco smoking article including a tobacco composition according to claim 3.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15390071A | 1971-06-16 | 1971-06-16 | |
US28691572A | 1972-09-07 | 1972-09-07 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3762423A true US3762423A (en) | 1973-10-02 |
Family
ID=26850975
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00286915A Expired - Lifetime US3762423A (en) | 1971-06-16 | 1972-09-07 | Methyl trans-2-isopropyl-5-methyl-3-hexenoate and derivatives thereof as tobacco flavorants |
Country Status (1)
Country | Link |
---|---|
US (1) | US3762423A (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4758548A (en) * | 1986-07-05 | 1988-07-19 | Basf Aktiengesellschaft | Novel aliphatic aldehydes and their preparation |
US5234706A (en) * | 1986-01-31 | 1993-08-10 | Slimak K M | Processes for products from potatoes and other roots, seeds, and fruit |
US5244689A (en) * | 1986-01-31 | 1993-09-14 | Slimak Karen M | Flour, bread, milk, and other products from white sweet potatoes cassava, edible aroids, amaranth, yams, and lotus |
US5789012A (en) * | 1986-01-31 | 1998-08-04 | Slimak; Kara M. | Products from sweet potatoes, cassava, edible aroids, amaranth, yams, lotus, potatoes and other roots, seeds and fruit |
US5904148A (en) * | 1995-06-08 | 1999-05-18 | Givaduan-Roure (International) Sa | Delayed release flavorant compositions |
US20040213864A1 (en) * | 1999-11-12 | 2004-10-28 | Slimak K M | Use of tropical root crops in effective intervention strategies for treating difficult and complex cases and chronic diseases |
Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2995476A (en) * | 1959-10-02 | 1961-08-08 | Philip Morris Inc | Organoleptic materials and method of production thereof |
US3047433A (en) * | 1961-10-19 | 1962-07-31 | Philip Morris Inc | Use of diels-alder adducts as tobacco additives |
US3111127A (en) * | 1961-06-27 | 1963-11-19 | Brown & Williamson Tobacco | Smoking tobacco product and method of making the same |
US3174485A (en) * | 1963-05-23 | 1965-03-23 | Brown & Williamson Tobacco | Organoleptically improved tobacco product |
US3381691A (en) * | 1965-11-08 | 1968-05-07 | Reynolds Tobacco Co R | Tobacco product |
US3449407A (en) * | 1966-01-11 | 1969-06-10 | Int Flavors & Fragrances Inc | Lactic acid esters of polyisoprenoid alcohols |
US3704714A (en) * | 1971-06-16 | 1972-12-05 | Liggett & Myers Inc | 2-isopropyl-5-methyl-2-hexenal, 2-isop-ropyl-5-methylhexanal,3-hydroxy-2-isopropyl-5-methylhexanal, and derivatives thereof as tobacco flavorants |
-
1972
- 1972-09-07 US US00286915A patent/US3762423A/en not_active Expired - Lifetime
Patent Citations (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2995476A (en) * | 1959-10-02 | 1961-08-08 | Philip Morris Inc | Organoleptic materials and method of production thereof |
US3111127A (en) * | 1961-06-27 | 1963-11-19 | Brown & Williamson Tobacco | Smoking tobacco product and method of making the same |
US3047433A (en) * | 1961-10-19 | 1962-07-31 | Philip Morris Inc | Use of diels-alder adducts as tobacco additives |
US3174485A (en) * | 1963-05-23 | 1965-03-23 | Brown & Williamson Tobacco | Organoleptically improved tobacco product |
US3381691A (en) * | 1965-11-08 | 1968-05-07 | Reynolds Tobacco Co R | Tobacco product |
US3449407A (en) * | 1966-01-11 | 1969-06-10 | Int Flavors & Fragrances Inc | Lactic acid esters of polyisoprenoid alcohols |
US3704714A (en) * | 1971-06-16 | 1972-12-05 | Liggett & Myers Inc | 2-isopropyl-5-methyl-2-hexenal, 2-isop-ropyl-5-methylhexanal,3-hydroxy-2-isopropyl-5-methylhexanal, and derivatives thereof as tobacco flavorants |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5234706A (en) * | 1986-01-31 | 1993-08-10 | Slimak K M | Processes for products from potatoes and other roots, seeds, and fruit |
US5244689A (en) * | 1986-01-31 | 1993-09-14 | Slimak Karen M | Flour, bread, milk, and other products from white sweet potatoes cassava, edible aroids, amaranth, yams, and lotus |
US5789012A (en) * | 1986-01-31 | 1998-08-04 | Slimak; Kara M. | Products from sweet potatoes, cassava, edible aroids, amaranth, yams, lotus, potatoes and other roots, seeds and fruit |
US4758548A (en) * | 1986-07-05 | 1988-07-19 | Basf Aktiengesellschaft | Novel aliphatic aldehydes and their preparation |
US5904148A (en) * | 1995-06-08 | 1999-05-18 | Givaduan-Roure (International) Sa | Delayed release flavorant compositions |
US5921247A (en) * | 1995-06-08 | 1999-07-13 | Givaudan-Roure (International) Sa | Delayed release flavorant compositions |
US6194019B1 (en) | 1995-06-08 | 2001-02-27 | Givaudan S.A. | Delayed release flavorant compositions |
US20040213864A1 (en) * | 1999-11-12 | 2004-10-28 | Slimak K M | Use of tropical root crops in effective intervention strategies for treating difficult and complex cases and chronic diseases |
US7854948B2 (en) | 1999-11-12 | 2010-12-21 | Slimak K M | Use of tropical root crops in dietary intervention strategies |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
AS | Assignment |
Owner name: UNITED STATES TRUST COMPANY OF NEW YORK, AS COLLAT Free format text: SECURITY INTEREST;ASSIGNOR:LEGGETT GROUP, INC.;REEL/FRAME:004688/0579 Effective date: 19870325 Owner name: UNITED STATES TRUST COMPANY OF NEW YORK, AS COLLAT Free format text: SECURITY INTEREST;ASSIGNOR:LEGGETT GROUP, INC., A CORP. OF DE.;REEL/FRAME:004688/0579 Effective date: 19870325 |
|
AS | Assignment |
Owner name: UNITED STATES TRUST COMPANY OF NEW YORK, NEW YORK Free format text: SECURITY INTEREST;ASSIGNOR:LIGGETT GROUP INC., A DE CORP.;REEL/FRAME:005208/0941 Effective date: 19891027 |
|
AS | Assignment |
Owner name: LIGGETT & MYERS TOBACCO COMPANY, A DE CORP., DELAW Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:LIGGETT GROUP INC., A CORP. OF DE;REEL/FRAME:005371/0796 Effective date: 19900629 Owner name: UNITED STATES TRUST COMPANY OF NEW YORK, NEW YORK Free format text: SECURITY INTEREST;ASSIGNOR:LIGGETT & MYERS TOBACCO COMPANY, A CORP. OF DE;REEL/FRAME:005371/0782 Effective date: 19900629 |