Organic Compound Patents (Class 131/276)
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Patent number: 5144964Abstract: This invention provides smoking compositions which contain a novel flavorant-release additive.Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as a molecular inclusion complex of a .beta.-cyclodextrin derivative and vanillin releases vanillin as a volatile flavorant component of the cigarette smoke. The released vanillin flavorant improves the taste of the mainstream smoke and imparts a pleasant aroma to the sidestream smoke.Type: GrantFiled: March 14, 1991Date of Patent: September 8, 1992Assignees: Philip Morris Incorporated, Philip Morris Products Inc.Inventor: Barbu A. Demain
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Patent number: 5133368Abstract: The present invention preferably relates to the use of an impact modifying agent and in particular the use of levulinic acid, a carbohydrate ester acetate or a carbohydrate ester levulinate in one or more of the component parts of a smoking article comprising a carbonaceous fuel element and a physically separate non-burning charge of tobacco or tobacco extract which article is capable of producing substantial quantities of aerosol, both initially and over the useful life of the product, without significant thermal degradation of the aerosol former and without the presence of substantial pyrolysis or incomplete combustion products or sidestream aerosol. The use of an impact modifying agent in smoking articles in accordance with the present invention provides the user with the sensations and benefits of cigarette smoking without burning tobacco and without the undesirable impact or off-taste commonly found in previous smoking articles.Type: GrantFiled: December 9, 1987Date of Patent: July 28, 1992Assignee: R. J. Reynolds Tobacco CompanyInventors: Calvin L. Neumann, William J. Casey, III
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Patent number: 5129954Abstract: This invention provides novel .beta.-hydroxyesters which have utility as a flavorant-release additive in smoking compositions.Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as ethyl 3-hydroxy-3-(4'-hydroxy-3'-methoxyphenyl)-2-phenylpropanoate pyrolyzes into vanillin and ethyl phenylacetate flavorants as volatile components of the cigarette smoke.Type: GrantFiled: June 13, 1990Date of Patent: July 14, 1992Assignees: Philip Morris Incorporated, Philip Morris Products Inc.Inventors: W. Geoffrey Chan, Yoram Houminer, John B. Paine, III, Kenneth F. Podraza
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Patent number: 5120368Abstract: This invention provides novel vanillyl 5-hydroxyesters, and smoking compositions which contain a vanillyl 5-hydroxyester as a flavorant-release additive.Under cigarette smoking conditions, a combustible filler and/or paper wrapper additive such as 4'-formyl-2'-methoxyphenyl 5-hydroxy-2-isopropylhexanoate pyrolyzes into vanillin and 2-isopropyl-5-hydroxyhexanoic acid delta lactone flavorants as volatile components of the cigarette smoke.Type: GrantFiled: August 10, 1990Date of Patent: June 9, 1992Assignees: Philip Morris Incorporated, Philip Morris Products, Inc.Inventors: Yoram Houminer, Kenneth F. Podraza, Everett W. Southwick
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Patent number: 5114493Abstract: This invention provides smoking compositions which contains a 6-substituted hexahydrobenzofuranone flavorant additive.Under cigarette smoking conditions the flavorant additive enhances the aroma and flavor of the cigarette smoke.Type: GrantFiled: November 2, 1988Date of Patent: May 19, 1992Assignees: Philip Morris Inc., Philip Morris Products Inc.Inventor: Kenneth F. Podraza
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Patent number: 5089469Abstract: Described are isomeric mixtures of bisabolene prepared by dehydrating nerolidol using citric acid or phosphoric acid and then distilling the resulting product at particular temperature ranges and particular pressure ranges in order to prepare a composition of matter useful for augmenting or enhancing natural, dry, floral, opoponax aromas with floral, freesia, fruity, citrus, bergamot, mango and opoponax topnotes in perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic, or zwitterionic detergents, fabric softener compositions, drier-added fabric softener articles, cosmetic powders and the like; and useful for repelling specific species of insects, namely, house flies Musca domestica L. (Diptera Muscidae)) and the species of mosquitoes, Aedes aegypti.Type: GrantFiled: April 25, 1991Date of Patent: February 18, 1992Assignee: International Flavors & Fragrances Inc.Inventors: Michael J. Zampino, Richard A. Wilson, Braja D. Mookherjee
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Patent number: 5057158Abstract: The ethyl esters of .beta.- and .gamma.-campholenic acids and of .gamma.-campholenic acid in admixture with .alpha.-campholenic acid and the ethyl esters of the corresponding dihydro derivatives have organoleptic properties which make them useful for preparing fragrances and flavors.Type: GrantFiled: September 30, 1986Date of Patent: October 15, 1991Assignee: Givaudan CorporationInventors: Martin Rohr, Cormack Flynn
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Patent number: 5041422Abstract: Described are hydroxy adamantane compounds and derivatives thereof and a process for preparing same.Type: GrantFiled: December 28, 1990Date of Patent: August 20, 1991Assignee: Flavors & Fragrances Inc. InternationalInventors: Anubhav Narula, Carlos Benaim
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Patent number: 5031646Abstract: Cigarettes having high nicotine content tobacco cut filler are rendered smooth smoking and palatable by incorporating an organic acid salt additive therein. For example, a cigarette having a cut filler with a blend nicotine content of greater than 2 percent has a sodium levulinate additive combined with the tobacco cut filler of the cigarette. Smooth smoking cigarettes yielding good tobacco taste and minimal off-taste are provided.Type: GrantFiled: January 16, 1990Date of Patent: July 16, 1991Assignee: R. J. Reynolds Tobacco CompanyInventors: Patrick M. Lippiello, Robert L. Suber, Sr., Jerry W. Redding, Thomas A. Perfetti
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Patent number: 5017235Abstract: In one of its embodiments this invention provides smoking compositions which contain a novel unsymmetrical 2,5-diacylpyrazine flavorant additive as illustrated by 1-[5-(1-propanoyl)-2-pyrazinyl]-2-methyl-1-propanone: ##STR1## Under normal cigarette smoking conditions, the 2,5-diacylpyrazine additive volatilizes and enhances the flavor and aroma of the mainstream and sidestream smoke.In another embodiment this invention provides novel unsymmetrical 2,5-diacylpyrazine compounds corresponding to the formula: ##STR2## where R is hydrogen or an alkyl radical containing between about 1-4 carbon atoms; and R.sup.1 and R.sup.2 are alkyl radicals containing between about 1-10 carbon atoms, and R.sup.1 and R.sup.2 are different alkyl groups.Type: GrantFiled: August 11, 1986Date of Patent: May 21, 1991Assignee: Philip Morris Inc.Inventors: David L. Williams, Everett W. Southwick
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Patent number: 4992106Abstract: Novel Oxo-ionol derivatives are described which have a but-1-en-3-ol carbonate side chain. These derivatives are stable tobacco enhancers which impart a slight hay-like flavor to tobacco smoke.Type: GrantFiled: March 23, 1989Date of Patent: February 12, 1991Assignee: BASF CorporationInventors: Philip A. Christenson, Robert G. Eilerman, Brian J. Drake
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Patent number: 4990496Abstract: Optically active isomers of alpha-damascone of formula ##STR1## wherein the wavy line designates a C--C bond of cis or trans configuration and its 3-buten-1-one derivative are new compounds having utility in the perfume and flavor industry. They can be prepared starting from an enolate of formula ##STR2## where the wavy line has the meaning given above and Me designates an alkali metal, preferably lithium or magnesium, by treating said enolate with a bifunctional nitrogen derivative of formula ##STR3## where the asterisk identifies a center of chirality;index n stands for zero or 1;each of symbols R.sup.0 and R.sup.1 defines a linear or branched alkyl or aralkyl radical, or one of them represents a hydrogen atom and the other an alkyl radical as defined above;each of symbols R.sup.2 and R.sup.Type: GrantFiled: February 3, 1989Date of Patent: February 5, 1991Assignee: Firmenich S.A.Inventors: Charles Fehr, Jose Galindo
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Patent number: 4966172Abstract: Flavor compositions and tobacco products containing 3,5,5,6,8,8-hexamethyl-1,2,3,4,5,6,7,8-octahydro-2-naphthalenone and methods for making same are disclosed.Type: GrantFiled: March 14, 1986Date of Patent: October 30, 1990Assignee: Givaudan CorporationInventors: Jean-Pierre Bachmann, Mario Pesaro
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Patent number: 4963193Abstract: Tobacco products, tobacco flavoring compositions, and methods for improving, modifying or enhancing the organoleptic properties of tobacco products, which comprise adding thereto an effective amount of an oxo-ionyl ester of the formula ##STR1## wherein: RCO represents an acyl group containing from one to eighteen carbon atoms,the dotted line in the side-chain represents an optional bond,one of the dotted lines in the ring represents an additional bond, and,Z represents an oxo group which is in the position .alpha. to the double bond in the ring,said amount being effective to modify the organoleptic properties of said tobacco product or composition.Type: GrantFiled: September 16, 1985Date of Patent: October 16, 1990Assignee: Givaudan CorporationInventor: Roman Kaiser
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Patent number: 4948781Abstract: The invention is concerned with compounds of the formula: ##STR1## wherein: R represents an alkyl group of one to four carbons, an alkenyl group of two to four carbons or a 1-alkoxy-alkyl group of the formula ##STR2## R.sup.1,R.sup.2 and R.sup.3 may be the same or different and represent hydrogen, methyl or ethyl;R.sup.4 represents hydrogen, an alkyl group of from one to five carbon atoms, an alkenyl group of from two to four carbon atoms or an alkylidene group of from one to four carbon atoms;R.sup.5,R.sup.6 and R.sup.7 may be the same or different and represent hydrogen, methyl or ethyl with the proviso that the sum R.sup.5 +R.sup.6 +R.sup.7 does not exceed two carbon atoms; andR.sup.8 represents methyl or ethyl;with the proviso that at least two, but not more than three of the symbols R.sup.1,R.sup.2,R.sup.3 and R.sup.4 represent hydrogen.This invention is also concerned with odorant and flavoring compositions containing these compounds.Type: GrantFiled: January 26, 1983Date of Patent: August 14, 1990Assignee: Givaudan CorporationInventors: Roman Kaiser, Dietmar Lamparsky
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Patent number: 4941486Abstract: Cigarette sidestream smoke can have the aroma thereof altered by placing the cigarette wrapping paper in intimate contact with a flavor precursor such as ethyl vanillin glucoside. The cigarettes exhibit good tobacco taste during use. The flavor precursor provides no substantial aroma to the cigarette prior to use thereof, and a characteristic aroma of the flavoring agent in the sidestream smoke during use thereof. Cigarettes can have a wrapping paper containing magnesium oxide and/or magnesium hydroxide, the paper having a net permeability of greater than 50 CORESTA units and an inherent permeability of less than 45 CORESTA units. The paper containing magnesium oxide and/or magnesium hydroxide is in intimate contact with a flavor precursor, and the filter of the cigarette includes a flavor carrier such as a flavored pellet.Type: GrantFiled: January 15, 1988Date of Patent: July 17, 1990Inventors: Michael F. Dube, Barry L. Saintsing
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Patent number: 4909854Abstract: Described for use in augmenting or enhancing the aroma or taste of smoking tobaccos and smoking tobacco articles, e.g., the body of smoking tobacco, the wrapper or the filter therefor in a cigarette or cigar, or the whole cigarette or cigar itself are compounds defined according to the generic structure: ##STR1## wherein R.sub.1 represents hydrogen, methyl or acetyl and wherein R.sub.2, R.sub.3, R.sub.4 and R.sub.5 represent the same or different hydrogen, methyl or ethyl.Type: GrantFiled: October 13, 1981Date of Patent: March 20, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Joseph A. McGhie, Futoshi Fujioka, Takao Yoshida
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Patent number: 4892966Abstract: The invention is concerned with a novel process for the manufacture of compounds of the formula ##STR1## wherein R.sup.1 signifies C.sub.1-5 -alkyl, especially methyl, ethyl, propyl or isopropyl, and the radicals R.sup.2 each independently represent hydrogen or C.sub.1-5 -alkyl, especially hydrogen or methyl, ethyl, propyl or isopropyl.The process is characterized in that a compound of the formula ##STR2## wherein R stands for C.sub.1-4 -alkoxy, chlorine, bromine or C.sub.1-4 -alkanoyloxy, R.sup.1 and R.sup.2 have the above significance and R.sup.3 represents C.sub.1-4 -alkyl.is hydrolyzed and subjected to an aldol condensation and, where R=C.sub.1-4 -alkoxy, the reaction product is subsequently subjected to an acid treatment.The compounds I are for the most part known flavoring substances.Type: GrantFiled: July 16, 1987Date of Patent: January 9, 1990Assignee: Givaudan CorporationInventor: Hans J. Wild
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Patent number: 4872917Abstract: This invention provides novel sclaral alkyl ether compounds, and smoking compositions which contain a sclaral alkyl ether compound as a flavorant additive. ##STR1## Under cigarette smoking conditions the sclaral ether is a volatile component which enhances the flavor of the mainstream smoke and the aroma of sidestream smoke.Type: GrantFiled: January 13, 1986Date of Patent: October 10, 1989Assignee: Philip Morris IncorporatedInventors: Charles R. Howe, Everett W. Southwick, Richard H. Cox
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Patent number: 4851050Abstract: .alpha.-Campholenic alcohol, dihydro-.alpha.-campholenic alcohol and the lower acyl esters thereof have organoleptic properties which make them useful as tobacco flavorants.Type: GrantFiled: January 30, 1986Date of Patent: July 25, 1989Assignee: Givaudan CorporationInventors: Martin Rohr, Richard H. Potter, Richard E. Naipawer
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Patent number: 4832059Abstract: Tobacco articles, including cigarettes, cigars, pipe tobacco and chewing tobacco, and the like, containing citral acetal which have a fresh, clean, true and long-lived citrus aroma and flavor.Type: GrantFiled: December 8, 1987Date of Patent: May 23, 1989Assignee: Lorillard, Inc.Inventors: Victor G. Garrard, Albert B. Hudson
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Patent number: 4825884Abstract: A tobacco treating process for forming favorable flavor compounds in a moisturized tobacco including the steps of contacting the tobacco with citrus pectin, invert sugar, or diammonium phosphate, or a combination resulting in a tobacco having a pectin level and diammonium phosphate level of predetermined percentages, thereof, introducing the moistened tobacco into a containing zone; introducing an ammonia source into the containing zone; heating the contained zone when substantially closed to bring the tobacco to a preselected temperature to improve flavor compounds through reaction of the ammonia source, citrus pectin, and reducing sugars, and/or other tobacco components; and cooling and removing the tobacco from the closed zone.Type: GrantFiled: October 5, 1987Date of Patent: May 2, 1989Assignee: Brown & Williamson Tobacco CorporationInventors: Robert F. Denier, Elmer F. Litzinger, Ezra D. Alford
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Patent number: 4804002Abstract: A tobacco product wrapper containing a glycoside comprising an acetyl of a carbohydrate and an aromatic agent or a derivative thereof. The glycoside flavors or masks the side stream smoke while substantially not altering the taste or flavor characteristics of the tobacco or mainstream smoke.Type: GrantFiled: May 29, 1987Date of Patent: February 14, 1989Assignee: P. H. Glatfelter CompanyInventor: Herron
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Patent number: 4794193Abstract: Described is a process for preparing 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone having the structure: ##STR1## and intermediates useful in such process defined according to the structure: ##STR2## wherein one of R.sub.3 or R.sub.4 is hydrogen and the other of R.sub.3 or R.sub.4 is acetyl; and one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is acetoxy, said compound defined according to the structure: ##STR3## being useful in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, chewing tobaccos, toothpastes, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles and perfumed polymers.Type: GrantFiled: April 15, 1982Date of Patent: December 27, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
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Patent number: 4786332Abstract: The present invention discloses fragrance and flavor compositions comprising 4-alkyl substituted cyclohexyl and cyclohex-3-enyl carboxylic acids wherein the 4-alkyl substituent is an ethyl, propyl or butyl group, and methods for preparing same.Type: GrantFiled: January 24, 1986Date of Patent: November 22, 1988Assignee: Givaudan CorporationInventors: Martin Rohr, N. Peter Vallone, Cormack Flynn
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Patent number: 4781762Abstract: Flavoring method and composition which include a carboxylate having the general formula: ##STR1## where R.sub.1 is an alkyl having from 1 to 14 carbons, alkenyl having from 2 to 14 carbons, cycloalkyl, cycloalkenyl, aryl, or furyl having from 4 to 14 carbons; R.sub.2 is alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or cycloalkynyl of from 1 to 7 carbons, aryl or oxyaryl of from 5 to 18 carbons, or a cycloaliphatic ether of from 5 to 6 carbons; and R.sub.3 is hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or cycloalkynyl of from 1 to 7 carbons, aryl, or oxyaryl of from 5 to 18 carbons, or a cycloaliphatic ether of from 5 to 6 carbons, or a radical of the general formula: ##STR2## where R.sub.4 and R.sub.5 independently are hydrogen or alkyl of from 1 to 6 carbons; and R.sub.6 is aryl, alkylaryl, aryloxy, alkoxy, cyclic acetal of from 3 to 7 carbons, dioxyalkyenyl ether of from 4 to 8 carbons; and M is cation other than hydrogen ion.Type: GrantFiled: May 20, 1987Date of Patent: November 1, 1988Assignee: Hercules IncorporatedInventor: Brian Byrne
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Patent number: 4756764Abstract: 3,10-Diacetyl-11-isopropylidene-7,7-dimethyl-tricyclo[6.2.1.0.sup.2,6 ]undeca-2,5,9-triene is a flavoring ingredient useful for the aromatization of smoking articles. It develops upon smoking green, slightly floral, metallic, astringent, fatty, slightly bitter and earthy notes.It is prepared by a two-step process from 1-(4-isopropylidene-1-cyclopent-1-enyl)-1-ethanone.Type: GrantFiled: February 26, 1987Date of Patent: July 12, 1988Assignee: Firmenich SAInventors: Alan F. Thomas, Alistair Y. Smith
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Patent number: 4753924Abstract: 4,4,7-trimethyl-3,4,7,8-tetrahydro-2(6H)-naphthalen-one is obtained by an elimination reaction from 3-oxo-.alpha.-ionol by way of direct addition thereof to a solution of a protonic acid in an inert solvent at an elevated temperature, or following its conversion into a low-carbon alkyl ester, particularly acetate, by way of the treatment of the latter, preferably with sodium acetate, in a polar non-protonic solvent at 150.degree.14 300.degree. C., wherein the output can be increased by raising the temperature of reaction. The product of the process is suitable, in pure form or as mixed with simultaneously produced 3,5,5-trimethyl-4-butenylidene-cyclo-hex-2-en-1-one, as an odiferous substance or as a fragrant substance for foods and tobacco.Type: GrantFiled: May 8, 1986Date of Patent: June 28, 1988Assignee: Dragoco Gerberding & Co. GmbHInventors: Ernst-Joachim Brunke, Ludwig Tumbrink
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Patent number: 4751933Abstract: Described are the uses of mixtures of hydroxybornyloxybutanes defined according to the generic structure: ##STR1## wherein in the mixture in each of the compounds one or R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is hydrogen in augmenting or enhancing the aroma or taste of smoking tobacco articles and smoking tobacco compositions.Type: GrantFiled: January 9, 1987Date of Patent: June 21, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Futoshi Fujioka, Richard M. Boden, William L. Schreiber
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Patent number: 4744375Abstract: A tobacco treating process for forming favorable flavor compounds in a moisturized tobacco including the steps of introducing the moistened tobacco into a containing zone; introducing an ammonia source into the containing zone; heating the contained zone when substantially closed to bring the tobacco to a preselected temperature to improve flavor compounds through reaction of the ammonia source and reducing sugars, and/or other tobacco components; and cooling and removing the tobacco from the closed zone.Type: GrantFiled: February 24, 1986Date of Patent: May 17, 1988Assignee: Brown & Williamson Tobacco CorporationInventors: Robert F. Denier, Elmer F. Litzinger, Ezra D. Allford
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Patent number: 4726384Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities therefor, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnamaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in the absence of any other reagents except inert solvent.Type: GrantFiled: June 11, 1986Date of Patent: February 23, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Charles Wiener, Alan O. Pittet
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Patent number: 4709707Abstract: Described is a process for augmenting or enhancing the aroma or taste of a smoking tobacco composition comprising the step of adding to said smoking tobacco composition, an aroma or taste augmenting or enhancing quantity of 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone having the structure: ##STR1## Smoking tobacco compositions and smoking tobacco articles containing said 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone are also described.Type: GrantFiled: October 17, 1986Date of Patent: December 1, 1987Assignee: International Flavors & Fragrances Inc.Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
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Patent number: 4701282Abstract: This invention provides smoking compositions which contain a .beta.-hydroxy-.gamma.-ketoester compound as a flavorant-release additive.In one of its embodiments, this invention provides tobacco compositions which contain a flavorant-release additive such as dodecyl 3-hydroxy-2,2,3-trimethyl-4-oxopentanoate: ##STR1## Under cigarette smoking conditions the above illustrated .beta.-hydroxy-.gamma.-keto ester pyrolyzes into 2,3-butanedione and other products which enhance the flavor of the mainstream smoke and the aroma of sidestream smoke.Type: GrantFiled: August 30, 1985Date of Patent: October 20, 1987Assignee: Philip Morris IncorporatedInventors: W. Geoffrey Chan, Yoram Houminer
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Patent number: 4690157Abstract: This invention provides smoking compositions which contain a novel hydroxylactone flavorant-release additive.Under cigarette smoking conditions, an additive such as 2-(1-hydroxy-1-phenylmethyl)-.gamma.-butyrolactone pyrolyzes into volatile benzaldehyde and .gamma.-butyrolactone constituents which enhance the flavor and aroma of the cigarette smoke.Type: GrantFiled: March 21, 1986Date of Patent: September 1, 1987Assignee: Philip Morris IncorporatedInventor: Kenneth F. Podraza
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Patent number: 4681976Abstract: Described are para-carboalkoxy cyclohexanones defined according to the structure: ##STR1## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.7 alkyl and R.sub.2 represents methyl or ethyl and uses thereof in augmenting or enhancing the aroma of consumable materials including foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, cosmetic compositions, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers. The compounds defined according to the structure: ##STR2## wherein R.sub.1 ' represents C.sub.4 -C.sub.7 alkyl and R.sub.2 represents methyl or ethyl are novel compounds.Type: GrantFiled: March 21, 1986Date of Patent: July 21, 1987Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Wilhelmus J. Wiegers, Robert P. Belko, Richard M. Boden
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Patent number: 4673582Abstract: Sweetening agents of general formula: ##STR1## wherein: X is a CN, COOC.sub.1 -C.sub.3 alkyl, COC.sub.1 -C.sub.3 alkyl, CONHC.sub.1 -C.sub.3 alkyl, SO.sub.2 C.sub.1 -C.sub.3 alkyl, SOC.sub.1 -C.sub.3 alkyl, SO.sub.2 NHC.sub.1 -C.sub.3 alkyl, NO.sub.2, F, Cl substituent;n is a number equal to 0 or 1;M is a hydrogen atom, or an organic or inorganic physiologically acceptable cation;Y is a COOC.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.3 alkyl, CH.sub.2 OH, CHOHCH.sub.3, CF.sub.3 substituent;Z is a C.sub.1 -C.sub.5 n-alkyl, isobutyl, isopentyl, phenyl, cyclohexyl, benzyl, cyclohexylmethyl, CH.sub.2 C.sub.6 H.sub.4 OH(p), CH.sub.2 OC.sub.1 -C.sub.4 alkyl, CH.sub.2 COOC.sub.1 -C.sub.4 alkyl, CH.sub.2 SC.sub.1 -C.sub.4 alkyl, CH.sub.2 CH.sub.2 SCH.sub.3, CH.sub.2 CH.sub.2 SO.sub.2 CH.sub.3, COOC.sub.1 -C.sub.4 alkyl, COOC.sub.3 -C.sub.7 cycloalkyl, CONHC.sub.2 -C.sub.4 alkyl, CONHC.sub.3 -C.sub.7 cycloalkyl, CONHC.sub.3 -C.sub.7 thiacycloalkyl, or CONHCH.sub.2 COOCH.sub.3 group;characterized in that A is an N--CN group.Type: GrantFiled: March 5, 1986Date of Patent: June 16, 1987Assignee: Universite Claude Bernard/Lyon 1Inventors: Claude Nofre, Jean M. Tinti
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Patent number: 4669490Abstract: This invention concerns the use of cis-3,7-dimethylocta-3,6-dienoic acid as a flavorant and flavor compositions and tobacco products containing same. This invention also concerns such flavor compositions and tobacco products wherein the cis-3,7-dimethylocta-3,6-dienoic acid is used in combination with 2,2,4-trimethylcyclohex-3(or)4-ene-carboxylic acid.Type: GrantFiled: June 20, 1984Date of Patent: June 2, 1987Assignee: Givaudan CorporationInventors: Peter Naegeli, Martin Rohr
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Patent number: 4643205Abstract: A smoking product having an improved flavor is prepared by applying a naturally occurring terpenoid glycoside sweetener to the portion of the product that is intended to be contacted by the smoker's lips.Type: GrantFiled: February 2, 1984Date of Patent: February 17, 1987Assignee: R. J. Reynolds Tobacco CompanyInventors: Jerry W. Redding, Donald L. Roberts, Donna K. Woods
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Patent number: 4638816Abstract: This invention provides smoking compositions which contain a glycosylamine compound as a flavorant-release additive. Under cigarette smoking conditions, an additive such as 1-amino-1-deoxyglucose pyrolyzes into volatile constituents which enhance the flavor of the mainstream smoke and the aroma of sidestream smoke.Type: GrantFiled: March 22, 1985Date of Patent: January 27, 1987Assignee: Philip Morris IncorporatedInventors: Richard H. Cox, Harvey J. Grubbs, Stephen A. Haut
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Patent number: 4629805Abstract: Described are para-carboalkoxy cyclohexanones defined according to the structure: ##STR1## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.7 alkyl and R.sub.2 represents methyl or ethyl and uses thereof in augmenting or enhancing the aroma of consumable materials including foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, cosmetic compositions, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers. The compounds defined according to the structure: ##STR2## wherein R.sub.1 ' represents C.sub.4 -C.sub.7 alkyl and R.sub.2 represents methyl or ethyl are novel compounds.Type: GrantFiled: April 23, 1985Date of Patent: December 16, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Wilhelmus J. Wiegers, Robert P. Belko, Richard M. Boden
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Patent number: 4627449Abstract: Described is a method for augmenting or enhancing the aroma or taste of smoking tobacco or smoking tobacco articles by adding to smoking tobacco or to at least one section of the smoking tobacco article, e.g., the paper, the filter or the body of tobacco, a mixture consisting essentially of:(a) from about 0.5 up to about 7% by weight of said composition of n-hexanal;(b) from about 5 up to about 21% by weight of said composition of n-octanal;(c) from about 30 up to about 80% by weight of said composition of n-nonanal;(d) from 0 up to about 40% by weight of said composition of n-decanal;(e) from 0 up to about 7% by weight of said composition of n-tetradecanal;(f) from about 7 up to about 12% by weight of said composition of n-heptanal;(g) from 0 up to about 12% by weight of said composition of n-undecanal; and(h) from 0 up to about 12% by weight of said composition of n-dodecanal.Particularly, on smoking the side stream is modified and masked.Type: GrantFiled: July 12, 1985Date of Patent: December 9, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Jacob Kiwala, Braja D. Mookherjee, Robert W. Trenkle
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Patent number: 4614831Abstract: Described are para-carboalkoxy cyclohexanones defined according to the structure: ##STR1## wherein R.sub.1 represents hydrogen or C.sub.1 -C.sub.7 alkyl and R.sub.2 represents methyl or ethyl and uses thereof in augmenting or enhancing the aroma of consumable materials including foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, perfume compositions, colognes and perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents, cosmetic compositions, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers. The compounds defined according to the structure: ##STR2## wherein R.sub.1 ' represents C.sub.4 -C.sub.7 alkyl and R.sub.2 represents methyl or ethyl are novel compounds.Type: GrantFiled: September 3, 1985Date of Patent: September 30, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Wilhelmus J. Wiegers, Robert P. Belko, Richard M. Boden
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Patent number: 4614610Abstract: Described is the novel compound genus defined according to the structure: ##STR1## wherein R.sub.1 is C.sub.1 -C.sub.3 lower alkyl useful in augmenting or enhancing the aroma or taste of consumable materials including perfumes, colognes, perfumed articles (including solid or liquid anionic, cationic, nonionic or zwitterionic detergents and perfumed polymers) smoking tobacco or smoking tobacco articles.Type: GrantFiled: March 14, 1984Date of Patent: September 30, 1986Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4612942Abstract: Diterpene glycosides have been found to enhance and modify the flavor of orally consumable compositions, such as foodstuffs, smoking compositions, chewing compositions, oral hygiene compositions and medicinal compositions to improve or vary the sensory perceptions thereof. An orally consumable composition having an enhanced or modified flavor comprises an effective amount of a diterpene glycoside. A diterpene glycoside can be added to an orally consumable composition as a constituent of the leaf material of Stevia rebaudiana. One or more compounds which are not diterpene glycosides, which contribute an unpleasant or unsweet taste to the leaf material of Stevia rebaudiana, can be removed from the leaf material by heating the leaf material at a temperature in the range of about 60.degree. C. to about 200.degree. C. or by extraction with an organic solvent having a polarity greater than hexane but less than water.Type: GrantFiled: March 8, 1984Date of Patent: September 23, 1986Assignee: Stevia Company, Inc.Inventors: Robert H. Dobberstein, Fred K. Suzuki
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Patent number: 4608445Abstract: The compounds of formulaX--CH.sub.2 --CH(OH)--CH.sub.2 --R (I)wherein symbol R represents a C.sub.1 -C.sub.3 alkyl radical and X a substituted cyclohexyloxy group of formula ##STR1## wherein index n stands for zero or one, the dashed lines indicate a single bond (n=1) or a double bond in position 2 (n=0) or 3 (n=1) and each of symbols R.sup.1 to R.sup.6 designates a hydrogen atom or a methyl radical, are new and can be conveniently utilized as perfuming and flavoring ingredients. They develop in particular woody-ambery notes.Type: GrantFiled: November 23, 1982Date of Patent: August 26, 1986Assignee: Firmenich SAInventors: Wolfgang K. Giersch, Karl H. Schulte-Elte, Gunther Ohloff
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Patent number: 4592373Abstract: This invention provides tobacco and non-tobacco smoking compositions which contain a heterocyclic-hydroxy-substituted carboxylate compound as a flavorant additive.In one of its embodiments, this invention provides tobacco compositions which contain a heterocylic-hydroxy-substituted carboxylic acid flavorant additive such as 2-(2-butyl)-3-hydroxy-3-methyl-3-(3-pyridyl)propionic acid: ##STR1## Under smoking conditions the above illustrated heterocyclic-hydroxy-substituted carboxylate additive and its pyrolysis products flavor the mainstream and sidestream smoke. The invention also provides for the method of preparing smoking compositions and the method of comprising the aroma imparted by the burning of a combustible article employing a heterocyclic-hydroxy-substituted carboxylate.Type: GrantFiled: October 27, 1983Date of Patent: June 3, 1986Assignee: Philip Morris Inc.Inventors: Yoram Houminer, Harvey J. Grubbs
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Patent number: 4590953Abstract: The lower alkyl esters of .alpha.-campholenic acid and .alpha.-campholanic acid have organoleptic properties which make them useful as tobacco flavorants.Type: GrantFiled: April 12, 1985Date of Patent: May 27, 1986Assignee: Givaudan CorporationInventors: Martin Rohr, Cormack Flynn
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Patent number: 4587981Abstract: Described is the use in (a) a process for augmenting or enhancing the aroma of tobacco; and (b) a flavored tobacco composition of norbornyl pyridine derivatives defined according to the generic structure: ##STR1## wherein R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 "' and R.sub.5 "" each represents hydrogen or methyl with the proviso that at least four of R.sub.5, R.sub.5 ', R.sub.5 ", R.sub.5 "' and R.sub.5 "" represent hydrogen; wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond and wherein the pyridinyl moiety is bonded to the norbornyl moiety at the 2' position of the norbornyl moiety and at either the 2 or the 4 position of the pyridinyl moiety.Type: GrantFiled: June 7, 1985Date of Patent: May 13, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Claude Grim
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Patent number: 4585662Abstract: The invention is concerned with compounds of the formula: ##STR1## wherein one of the symbols R.sup.1,R.sup.2 and R.sup.3 stands for methyl or ethyl and the others stand for hydrogen and R.sup.4 signifies hydrogen or methyl, with the proviso that R.sup.4 represents hydrogen when R.sup.1 and R.sup.2 both represent hydrogen and R.sup.3 represents methyl and their use as odorants and flavorants.Type: GrantFiled: June 25, 1984Date of Patent: April 29, 1986Assignee: Givaudan CorporationInventors: Roman Kaiser, Dietmar Lamparsky
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Patent number: RE32721Abstract: Described are compounds covered by the generic structure. ##STR1## where one, two or all of R.sub.1, R.sub.2 and R.sub.3 are the same or different and each represents hydrogen or lower alkyl of from 1 up to 3 carbon atoms; a process for preparing same using compounds having the generic structure; ##STR2## where one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents carbon-carbon single bonds and organoleptic uses thereof in perfumes, colognes, perfumed articles such as anionic, cationic and non-ionic detergents, cosmetic powders and dryer-added fabric softener articles, as well as in smoking tobaccos and smoking tobacco articles, e.g., the body of smoking tobacco, the wrapper or the filter therefor.Type: GrantFiled: December 21, 1984Date of Patent: July 26, 1988Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, James M. Sanders, William L. Schreiber, Hugh Watkins, Joaquin F. Vinals, Edward J. Shuster, Thomas J. O'Rourke, Myrna L. Hagedorn, Philip Klemarczyk