Carbocyclic Patents (Class 426/538)
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Patent number: 4136208Abstract: Norbornane Derivatives are used in foodstuffs and flavorings. Specifically, 3,3-dimethyl-2-pentanoylnorbornane and 2-butyrl-3,3-dimethylnorbornane are used.Type: GrantFiled: December 13, 1977Date of Patent: January 23, 1979Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, James M. Sanders, Manfred H. Vock, Edward J. Shuster, Joaquin Vinals, William L. Schreiber, John B. Hall, Denis E. Hruza, Sr., Venkatesh Kamath, Braja D. Mookherjee, Ching Y. Tseng, Mark A. Sprecker
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Patent number: 4136066Abstract: 1-Crotonoyl-2,2,6-trimethylcyclohexane occurs in four stereoisomeric forms. In particular the trans, E and cis, E isomers having interesting organoleptic properties and are useful in the preparation of perfume compositions. Processes for preparing the stereoisomers, in a pure form or as mixtures, are described.Type: GrantFiled: April 13, 1978Date of Patent: January 23, 1979Assignee: P.F.W. Beheer B.V.Inventors: Douwe R. De Haan, Dirk K. Kettenes
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Patent number: 4131687Abstract: Described are processes and compositions for augmenting or enhancing the flavor and/or aroma of consumable materials including foodstuffs, chewing gums, medicinal products, toothpastes, perfumes, colognes, and perfumed articles using as the essential ingredient at least one C.sub.10 -terpene alkyl, alkenyl, haloalkenyl, and alkynyl ether and diether having the formula:(C.sub.10 -TERPENYL) (O-R.sub.1).sub.nwherein n is 1 or 2; the terpene group is a moiety having one of the structures: ##STR1## AND R.sub.1 is one of C.sub.1 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, C.sub.3 alkynyl, or C.sub.3 haloalkenyl. The compounds wherein R.sub.1 is C.sub.2 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, C.sub.3 alkynyl or C.sub.3 haloalkenyl are novel compounds.Type: GrantFiled: January 27, 1978Date of Patent: December 26, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Cynthia J. Mussinan, Braja D. Mookherjee, Manfred H. Vock, Frederick L. Schmitt, Edward J. Shuster, James M. Sanders, Bette M. Light, Edward J. Granda
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Patent number: 4130508Abstract: Processes and compositions are described for use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma; tobacco flavor and aroma; perfume and perfumed article aroma augmenting, enhancing and imparting compositions; and as foodstuff, chewing gum, toothpaste, medicinal product, tobacco, perfume and perfumed article aroma imparting materials of one or more cyclohexadiene derivatives having the generic formula: ##STR1## wherein R is one of C.sub.1 -C.sub.5 alkyl, R.sub.1 is methyl when R.sub.2 is hydrogen, and R.sub.1 is hydrogen when R.sub.2 is methyl.Type: GrantFiled: December 13, 1977Date of Patent: December 19, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Bette M. Spencer, Joaquin F. Vinals, Jacob Kiwala, Manfred H. Vock, Edward J. Shuster
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Patent number: 4128101Abstract: 3-Ethoxy-4-hydroxybenzaldehyde 2,2-dimethyl-propanediol acetal has a unique flavor and aroma which markedly enhance the flavor and aroma of tobacco products and comestibles. Unlike ethyl vanillin from which it is derived, the acetal has a less pronounced vanilla or ethyl vanillin odor and taste and a more intense chocolate by-note.Type: GrantFiled: May 10, 1977Date of Patent: December 5, 1978Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Kurt Kulka, Frank Mild, Frank Fischetti, Jr.
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Patent number: 4126570Abstract: Norbornane derivatives are used in detergents. Specifically, ##STR1## and mixtures of same or a mixture of 2-(2-butenoyl)-3,3-dimethylnorbornane; 2-(3-butenoyl)-3,3-dimethylnorborna ne; 2-(2-butenoyl)-3,3-dimethylnorbornane and alpha-allyl-3,3-dimethyl-2-norbornanemethanol are used.Type: GrantFiled: December 13, 1977Date of Patent: November 21, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, James M. Sanders, Manfred H. Vock, Edward J. Shuster, Joaquin Vinals, William L. Schreiber, John B. Hall, Denis E. Hruza, Sr., Venkatesh Kamath, Braja D. Mookherjee, Ching Y. Tseng, Mark A. Sprecker
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Patent number: 4122120Abstract: Described is a mixture of 1-(3,3-dimethylcyclohexyl)-4-methyl-cis-2-pentene-1-one, 1-(3,3-dimethylcyclohexyl)-4-methyl-trans-2-pentene-1-one, and 1-(3,3-dimethylcyclohexyl)-4-methyl-3-pentene-1-one and a mixture of 1-(3,3-dimethylcyclohexyl)-cis-2-pentene-1-one, 1-(3,3-dimethylcyclohexyl) -trans-2-pentene-1-one and 1-(3,3-dimethylcyclohexyl)-3-pentene-1-one, useful in augmenting or enhancing flavors and perfume and perfumed article aromas.Type: GrantFiled: July 28, 1977Date of Patent: October 24, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
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Patent number: 4119106Abstract: This invention provides alcohol flavorant-release oligomeric and polymeric derivatives corresponding to the structural formula: ##STR1## wherein R is selected from aliphatic, alicyclic, heterocyclic and aromatic hydrocarbon radicals; R.sup.1 and R.sup.2 are selected from hydrogen and aliphatic, alicyclic, heterocyclic and aromatic hydrocarbon radicals; and n is an integer.Type: GrantFiled: October 1, 1976Date of Patent: October 10, 1978Assignee: Philip Morris, IncorporatedInventors: Harvey J. Grubbs, Thomas V. Van Auken, William R. Johnson, Jr.
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Patent number: 4119574Abstract: Processes and compositions are described for the use in perfume and perfumed article aroma augmenting, enhancing and imparting compositions and as perfume and perfumed article aroma imparting materials of hydroxy cyclohexenone derivatives having the generic formula: ##STR1## wherein one of X and Y is a keto moiety having the structure: ##STR2## and the other of X and Y is a carbinol moiety having the structure: ##STR3## wherein R is C.sub.1 -C.sub.5 alkyl. Addition of one or more hydroxy cyclohexenone derivatives having the formula: ##STR4## to consumable materials is indicated to produce: In perfumes, colognes and perfumed articles, green, minty, herbaceous, strong fruity aromas with earthy, mossy notes.Type: GrantFiled: November 15, 1977Date of Patent: October 10, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Bette M. Spencer, Joaquin F. Vinals, Jacob Kiwala, Manfred Hugo Vock, Edward J. Shuster
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Patent number: 4118343Abstract: Method for improving, enhancing or modifying the organoleptic properties of perfumes or perfume products as well as of foodstuffs in general, beverages and tobacco, by incorporating therein an oxygenated tricyclic derivative of norbornene.Type: GrantFiled: August 15, 1977Date of Patent: October 3, 1978Assignee: Firmenich, S.A.Inventors: Werner Skorianetz, Gunther Ohloff
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Patent number: 4114630Abstract: Spirane derivatives, most of them are new, useful as odor-modifying ingredients for manufacturing perfumes and perfumed products, and as flavor-modifying ingredients for the manufacture of artificial flavors of for flavoring foodstuffs, animal feeds, beverages, pharmaceutical preparations and tobacco products.Process for preparing said spirane derivatives.Type: GrantFiled: October 21, 1976Date of Patent: September 19, 1978Assignee: Firmenich SAInventors: Walter Renold, Werner Skorianetz, Karl-Heinrich Schulte-Elte, Gunther Ohloff
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Patent number: 4109022Abstract: 1-Crotonoyl-2,2,6-trimethylcyclohexane occurs in four stereoisomeric forms. In particular the trans, E isomer has interesting organoleptic properties and is useful in the preparation of perfume and flavoring compositions. Processes for preparing the stereoisomers, in a pure form or as mixtures, are described.Type: GrantFiled: April 28, 1976Date of Patent: August 22, 1978Assignee: P.F.W. Beheer B.V.Inventors: Douwe Rienk de Haan, Dirk Karel Kettenes
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Patent number: 4107094Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma and perfume aroma augmenting, enhancing, modifying and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, perfume and perfumed article aroma imparting materials of 3,3-dimethyl-2(3-butenyl) norbornanol-2 (hereinafter referred to as the "norbornanol derivative" having the structure: ##STR1## (which structure is intended to cover both the "endo" and the "exo" isomers thereof) produced by a process which comprises reacting an allylic Grignard reagent having the structure: ##STR2## wherein X is chloro, bromo or iodo with camphene oxide having the structure: ##STR3## by either "exo" camphene oxide or "endo" camphene oxide or a mixture of "exo" and "endo" camphene oxide.Type: GrantFiled: September 19, 1977Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Manfred Hugo Vock, Edward J. Shuster, Frederick Louis Schmitt
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Patent number: 4107209Abstract: The compounds 1-[3-(methylthio)butyryl]-2,6,6-trimethyl-cyclohexene and/or the corresponding 1,3-cyclohexadiene analog having the generic structure: ##STR1## wherein the dashed line could be a single or a double carbon-carbon bond and processes and compositions containing same are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, tobacco flavor and aroma and perfume and perfumed article aroma augmenting and enhancing compositions and for use in foodstuffs, tobacco, perfume and perfumed article aroma imparting compositions; produced by a process illustrated by the reaction: ##STR2## The above-mentioned compounds produce: (A) In food flavorings, sweet, black tea-like, cocoa-like, damascenone-like, chocolate-like, dried fruit-like, rose petal-like aroma characteristics and sweet, black-tea-like, cocoa-like, damascenone-like, chocolate-like, tobacco-like, dried fruit-like and rose petal-like flavor characteristics;(b) In tobacco, a sweet honey-like, rich, slightlyType: GrantFiled: March 3, 1977Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Richard A. Wilson, Braja Dulal Mookherjee, Anne Sanderson Hruza, Manfred Hugo Vock, Louis Schmitt Frederick, Joaquin Francisco Vinals
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Patent number: 4107093Abstract: Compositions are described for the use in perfume and cologne of the compound ##STR1## or of mixtures of the compounds ##STR2## to produce fruity, woody, piney aromas with armoise and floral nuances and slight chocolate undertones.Type: GrantFiled: July 28, 1977Date of Patent: August 15, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
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Patent number: 4103036Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, tobacco flavor and aroma, perfume and perfumed article aroma augmenting, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, tobacco, perfume and perfumed article aroma imparting materials of one or more derivatives of 1-acetyl-3,3-dimethylcyclohexane having the generic formula: ##STR1## wherein one of the dashed lines may be a carbon-carbon single bond or a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond and R is hydrogen or methyl.Type: GrantFiled: July 28, 1977Date of Patent: July 25, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
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Patent number: 4097416Abstract: Described are the compounds 1-(2-propenyl)-3-(4-methyl-3-pentenyl)-.DELTA..sup.3 -cyclohexene-1-carboxaldehyde and 1-(2-propenyl)-4-(4-methyl-3-pentenyl)-.DELTA..sup.3 -cyclohexene-1-carboxaldehyde; and a process for preparing same by means of reacting an -cyclohexene-1-carboxaldehyde using a phase transfer agent in a two phase system according to the reaction: ##STR1## wherein the carboxaldehyde moiety is bonded to the alpha-carbon atom or the beta-carbon atom, X is chloro or bromo and M is alkali metal, processes for adding such 1-(2-propenyl)-(4-methyl-3-pentenyl)-.DELTA..sup.3 -cyclohexene-1-carboxaldehydes to consumable materials whereby:In perfumes sweet, fruity, lavender notes with citrus, floral and balsam nuances are imparted, augmented and/or enhanced.Type: GrantFiled: August 24, 1977Date of Patent: June 27, 1978Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals, Robert M. Novak
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Patent number: 4093565Abstract: A method of making a synthetic lime mix having the fragrance of steam distilled lime oil comprising the steps of refluxing a mixture of citral or a citral containing oil and water in the presence of an acid catalyst, distilling the refluxed mixture and recovering a reaction product containing 1-methyl-1,3-cyclohexadiene.Type: GrantFiled: March 18, 1976Date of Patent: June 6, 1978Assignee: Colgate-Palmolive CompanyInventor: Robert John Steltenkamp
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Patent number: 4089986Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma and perfume aroma augmenting, enhancing, modifying and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, perfume and perfumed article aroma imparting materials of 3,3-dimethyl-2(3-butenyl) norbornanol-2 (hereinafter referred to as the "norbornanol derivative" having the structure: ##STR1## (which structure is intended to cover both the "endo" and the "exo" isomers thereof) produced by a process which comprises reacting an allylic Grignard reagent having the structure: wherein X is chloro, bromo or iodo with camphene oxide having the structure: ##STR2## by either "exo" camphene oxide or "endo" camphene oxide or a mixture of "exo" and "endo" camphene oxide.Type: GrantFiled: September 19, 1977Date of Patent: May 16, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Manfred Hugo Vock, Edward J. Shuster, Frederick Louis Schmitt
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Patent number: 4084009Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, tobacco flavor and aroma, perfume and perfumed article aroma augmenting, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, tobacco, perfume and perfumed article aroma imparting materials of hydroxy cyclohexenone derivatives having the generic formula: ##STR1## wherein one of X and Y is a keto moiety having the structure: ##STR2## and the other of X and Y is a carbinol moiety having the structure: ##STR3## and wherein R is C.sub.1 -C.sub.5 alkyl.Type: GrantFiled: March 3, 1977Date of Patent: April 11, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Bette M. Spencer, Joaquin F. Vinals, Jacob Kiwala, Manfred Hugo Vock, Edward J. Shuster
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Patent number: 4081479Abstract: Described in a genus of substituted 1-acetyl-3,3-dimethylcyclohexanes having the structure: ##STR1## wherein R.sub.1 or one or both of R.sub.2 and/or R.sub.3 is methallyl and the other of R.sub.1 or R.sub.2 and/or R.sub.Type: GrantFiled: December 22, 1976Date of Patent: March 28, 1978Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker, Frederick Louis Schmitt, Manfred Hugo Vock
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Patent number: 4076853Abstract: Norbornane derivatives are used in foodstuffs and flavorings. Specifically, alpha-allyl-3, 3-dimethyl-2-norbornanemethanol, alpha-methallyl-3,3-dimethyl-2-norbornanemethanol, and alpha-allyl-alpha-3,3-trimethyl-2-norbornanemethanol are used.Type: GrantFiled: February 4, 1977Date of Patent: February 28, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, James Milton Sanders, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals, William L. Schreiber, John B. Hall, Denis E. Hruza, Sr., Venkatesh Kamath, Braja Dulal Mookherjee, Ching Y. Tseng, Mark A. Sprecker
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Patent number: 4076854Abstract: Processes and compositions are described for use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma; tobacco flavor and aroma; perfume and perfumed article aroma augmenting, enhancing and imparting compositions; and as foodstuff, chewing gum, toothpaste, medicinal product, tobacco, perfume and perfumed article aroma imparting materials of one or more cyclohexadiene derivatives having the generic formula: ##STR1## wherein R is one of C.sub.1 -C.sub.5 alkyl, R.sub.1 is methyl when R.sub.2 is hydrogen, and R.sub.1 is hydrogen when R.sub.2 is methyl.Type: GrantFiled: March 3, 1977Date of Patent: February 28, 1978Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Bette M. Spencer, Joaquin F. Vinals, Jacob Kiwala, Manfred Hugo Vock, Edward J. Shuster
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Patent number: 4073751Abstract: Described is the compound 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane, a process for preparing same by means of reacting an allylic halide with acetyl-3,3-dimethylcyclohexane using a phase transfer agent and in a two phase system according to the reaction: ##STR1## wherein X is chloro or bromo, processes for adding 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane to consumable materials whereby:I. In foodstuffs and medicinal products, fruity, pineapple, allyl-caproate-like, galbanum and woody aroma characteristics are augmented or enhanced and rosey, ionone, oriental-like and woody flavor characteristics are augmented or enhanced; andIi. In perfumes and perfumed articles, sweet, earthy, animal aromas with pineapple and ambery nuances and tobacco/animal notes are imparted, augmented and/or enhancedAnd flavor compositions and perfume compositions containing 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane.Type: GrantFiled: February 4, 1977Date of Patent: February 14, 1978Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock
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Patent number: 4068012Abstract: Described are the compounds 1-(2-propenyl)-3-(4-methyl-3-pentenyl)-.DELTA..sup.3 -cyclohexene-1-carboxaldehyde and 1-(2-propenyl)-4-(4-methyl-3-pentenyl)-.DELTA..sup.3 -cyclohexene-1-carboxaldehyde; and a process for preparing same and, processes for adding such aldehydes to consumable materials whereby:I. In foodstuffs and medicinal products, sweet, fatty, cocoa butter-like, green/grassy, dairy, diacetyl-like, apricot-like and carrot-like aroma characteristics and fatty, cocoa butter-like, green/grassy, dairy-like, diacetyl-like, peach and coconut flavor characteristics are augmented or enhanced;Ii. In perfumes and perfumed articles, sweet, fruity, lavender notes with citrus, floral and balsam nuances are imparted, augmented and/or enhanced; andIii.Type: GrantFiled: November 11, 1976Date of Patent: January 10, 1978Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals, Robert M. Novak
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Patent number: 4064184Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma and perfume aroma augmenting, enhancing, modifying and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, perfume and perfumed article aroma imparting materials of 3,3-dimethyl-2(3-butenyl) norbornanol-2 (hereinafter referred to as the "norbornanol derivative" having the structure: ##STR1## (which structure is intended to cover both the "endo" and the "exo" isomers thereof) produced by a process which comprises reacting an allylic Grignard reagent having the structure: ##STR2## wherein X is chloro, bromo or iodo with camphene oxide having the structure: ##STR3## by either "exo" camphene oxide or "endo" camphene oxide or a mixture of "exo" and "endo" camphene oxide. Addition of the said norbornanol derivative to consumable materials is indicated to produce:A.Type: GrantFiled: November 11, 1976Date of Patent: December 20, 1977Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Manfred Hugo Vock, Edward J. Shuster, Frederick Louis Schmitt
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Patent number: 4064281Abstract: Described is the compound 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane, a process for preparing same by means of reacting an allylic halide with acetyl-3,3-dimethylcyclohexane using a phase transfer agent and in a two phase system according to the reaction: ##STR1## wherein X is chloro or bromo, processes for adding 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane to consumable materials whereby:I. In foodstuffs and medicinal products, fruity, pineapple, allyl-caproate-like, galbanum and woody aroma characteristcs are augmented or enhanced and rosey, ionone, oriental-like and woody flavor characteristics are augmented or enhanced; andIi. In perfumes and perfumed articles, sweet, earthy, animal aromas with pineapple and ambery nuances and tobacco/animal notes are imparted, augmented and/or enhancedAnd flavor compositions and perfume compositions containing 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane.Type: GrantFiled: February 4, 1977Date of Patent: December 20, 1977Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker, Frederick Louis Schmitt, Manfred Hugo Vock
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Patent number: 4062894Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, tobacco flavor and aroma, perfume and perfumed article aroma augmenting, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, tobacco, perfume and perfumed article aroma imparting materials of one or more derivatives of 1-acetyl-3,3-dimethylcyclohexane having the generic formula: ##STR1## wherein one of the dashed lines may be a carbon-carbon single bond or a carbon-carbon double bond and the other of the dashed lines is a carbon-carbon single bond and R is hydrogen or methyl.Type: GrantFiled: August 11, 1976Date of Patent: December 13, 1977Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
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Patent number: 4053657Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma and perfume aroma augmenting, enhancing, modifying and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, perfume and perfumed article aroma imparting materials of 1-(3,3-dimethyl-2-norbornyl)-2-propanone (hereinafter referred to as the "norbornylpropanone derivative") having the structure: ##STR1## (which structure is intended to cover both the "endo" and the "exo" isomers thereof). Addition of the said "norbornyl-propanone derivative" to consumable materials is indicated to produce:A. In foodstuffs, foodstuff flavorings, chewing gums, toothpastes and medicinal products, fruity/berry, pine needle-like aromas and sweet, fruity/berry, blueberry-like, pine needle-like, pine balsam flavor characteristics; andB.Type: GrantFiled: December 3, 1976Date of Patent: October 11, 1977Assignee: International Flavors & Fragrances Inc.Inventors: William L. Schreiber, James N. Siano, Manfred Hugo Vock, Edward J. Shuster
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Patent number: 4048120Abstract: Cyclobutane derivatives useful as odor-modifying ingredients for manufacturing perfumes and perfumed products, and as flavor-modifying ingredients for the manufacture of artificial flavors or for flavoring foodstuffs, feedstuffs, beverages, pharmaceutical preparations or tobacco products.Type: GrantFiled: May 26, 1976Date of Patent: September 13, 1977Assignee: Firmenich S.A.Inventor: Valentin Rautenstrauch
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Patent number: 4044164Abstract: Processes and compositions are described for use in foodstuff flavors and as foodstuff article aroma and taste augmenting and enhancing materials of at least one .alpha.-oxy(oxo) sulfide and ether having the structure: ##STR1## wherein X is one of: ##STR2## Z is one of sulfur or oxygen; when R.sub.1 and R.sub.2 are taken separately, R.sub.1 is hydrogen or methyl, and R.sub.2 is methyl; and when R.sub.1 and R.sub.2 are taken together, R.sub.1 and R.sub.2 form phenyl moieties; and Y is one of C.sub.1 -C.sub.4 alkyl, C.sub.3 or C.sub.4 alkenyl, acetyl, methoxycarbonylmethyl, or 1,3-diethylacetonyl. The compounds of our invention are useful in augmenting or enhancing the flavor and aroma nuances of berry flavors, cereal-like flavors, nut flavors, broccoli flavors, onion flavors, citrus flavors (including neroli, bergamot, lime), jasmin flavors, grapefruit flavors, concord grape flavors, blackcurrant flavors, milk caramel flavors (e.g.Type: GrantFiled: October 7, 1976Date of Patent: August 23, 1977Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Howard H. Heinsohn, Jr., Manfred Hugo Vock
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Patent number: 4036886Abstract: Described are processes for preparing novel 4- and 5-phenyl-pentenals, lower alkyl and lower alkylene acetals thereof having the structure: ##STR1## wherein one of X and Y is phenyl and the other of X and Y is hydrogen and A is a moiety selected from the group consisting of: ##STR2## WHEREIN R.sub.b and R.sub.b ' separately are the same or different lower alkyl or R.sub.b and R.sub.b ' taken together form a lower alkylene group either (i) comprising the step of intimately admixing the lithium salt of a Schiff base of acetaldehyde and an amine with a phenyl-substituted compound selected from the group consisting of phenyl alkanals and phenyl alkenyl bromides in order to produce a phenyl-substituted Schiff base and treating said phenyl-substituted Schiff base with an acid, or (ii) comprising the steps of first admixing phenyl propionaldehyde with a tri-substituted formyl methylene phosphorane in a non-reactive solvent and then heating the resulting mixture.Type: GrantFiled: April 12, 1976Date of Patent: July 19, 1977Assignee: International Flavors & Fragrances Inc.Inventors: William Lewis Schreiber, Gerard Joseph Mosciano, Alan O. Pittet, Manfred Vock, Edward Joseph Shuster
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Patent number: 4033994Abstract: Compounds are disclosed having a physiological cooling action on the skin. The compositions contain, as the effective ingredient, certain esters of p-menthane 3-carboxylic acid.Type: GrantFiled: July 8, 1974Date of Patent: July 5, 1977Assignee: Wilkinson Sword LimitedInventors: Hugh R. Watson, David G. Rowsell, John H. D. Browning
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Patent number: 4029106Abstract: Process for improving, enhancing or modifying the organoleptic properties of a tobacco product, which comprises adding thereto about 1 to about 1000 parts per million based on the weight of tobacco of 3-isopropyl-cyclopent-2-en-1-one.Type: GrantFiled: June 12, 1975Date of Patent: June 14, 1977Assignee: Firmenich S.A.Inventor: Edouard Demole
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Patent number: 4021494Abstract: Described is a process for producing an organic tricyclic alcohol having the formula: ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is selected from the group consisting of hydrogen and methyl; wherein the dashed line is a carbon-carbon single bond or a carbon-carbon double bond; and wherein when the dashed line is a carbon-carbon single bond, one of R.sub.2 or R.sub.3 is hydrogen.Type: GrantFiled: August 11, 1976Date of Patent: May 3, 1977Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, Edward J. Shuster, Joaquin F. Vinals, Manfred Hugo Vock
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Patent number: 4021488Abstract: Described is the compound 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane, a process for preparing same by means of reacting an allylic halide with acetyl-3,3-dimethylcyclohexane using a phase transfer agent and in a two phase system according to the reaction: ##STR1## wherein X is chloro or bromo, processes for adding 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane to consumable materials whereby:I. In foodstuffs and medicinal products, fruity, pineapple, allyl-caproate-like, galbanum and woody aroma characteristics are augmented or enhanced and rosey, ionone, oriental-like and woody flavor characteristics are augmented or enhanced; andIi. In perfumes and perfumed articles, sweet, earthy, animal aromas with pineapple and ambery nuances and tobacco/animal notes are imparted, augmented and/or enhancedAnd flavor compositions and perfume compositions containing 1-acetyl-3,3-dimethyl-(2-propenyl)cyclohexane.Type: GrantFiled: August 11, 1976Date of Patent: May 3, 1977Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker, Frederick Louis Schmitt, Manfred Hugo Vock
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Patent number: 4011270Abstract: A recrystallized menthol product derived from crude natural menthol is described for incorporation into foods, beverages and tobacco in amounts sufficient to create a lingering cool sensation in the mouth of the user of the food, beverage or tobacco with little or no taste of menthol. The recrystallized menthol product is recrystallized from an ethanol-water solution of crude natural menthol under specific conditions.Type: GrantFiled: May 28, 1974Date of Patent: March 8, 1977Assignee: I. P. Callison & Sons, Inc.Inventor: Richard Gardner Carrington
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Patent number: 4001453Abstract: Sweetening compositions with substantially instantaneous effect are made with a mixture of certain dihydrochalcones and agents such as gluconodelta-lactone, or gluconic acid or physiologically acceptable salts of such agents.Type: GrantFiled: September 19, 1974Date of Patent: January 4, 1977Assignee: Givaudan CorporationInventors: Ulrich Huber, Nicolas Kosslakoff, Bruno Vaterlaus
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Patent number: 4000329Abstract: Processes and compositions are described for the use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, tobacco flavor and aroma and perfume aroma augmenting, modifying, enhancing and imparting compositions and as foodstuff, chewing gum, toothpaste, medicinal product, tobacco, perfume and perfumed article aroma imparting materials of one or more alkyl side chain methyl substituted or unsubstituted 2,2,6-trimethyl-1-cyclohexen-1-vinyl alkanoates (hereinafter referred to as "enol esters") having the generic structure: ##STR1## (which structure is intended to cover both the "cis" and the "trans" isomers thereof) wherein R.sub.1 is C.sub.1 -C.sub.11 alkyl and R.sub.4 is hydrogen or methyl.Type: GrantFiled: March 1, 1976Date of Patent: December 28, 1976Assignee: International Flavors & Fragrances Inc.Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
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Patent number: 3998974Abstract: Nonnutritive flavor imparting compounds of the general formula (F--Z).sub.n C wherein F is an active flavor imparting agent, C is a controlling agent for transporting and essentially restricting absorption of the compound (F--Z).sub.n C in a biological environment, Z is a covalent bond for bonding F to C and n is at least one. The nonnutritive flavor imparting compounds are useful for imparting flavor and taste to foods, beverages, confections and medicinals without any substantial absorption of the flavor imparting compounds in the environment of use.Type: GrantFiled: June 6, 1975Date of Patent: December 21, 1976Assignee: Dynapol CorporationInventor: Alejandro Zaffaroni
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Patent number: 3996296Abstract: Described are the novel compounds, 4-(2,6,6-trimethyl-1,3-cyclohexadien-1-yl)-2-butanol and 4-(6,6-dimethyl-2-methylene-3-cyclohexen-1-yl)-2-butanol, and processes for preparing the aforementioned alcohols and acetate esters thereof.Type: GrantFiled: March 24, 1975Date of Patent: December 7, 1976Assignee: International Flavors & Fragrances Inc.Inventors: Braja Dulal Mookherjee, Manfred Hugo Vock, Carlos Benaim, Edward J. Shuster
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Patent number: 3993604Abstract: Use of alicyclic compounds, some of which are new, as odor-modifying ingredients for manufacturing perfumes, perfumed products or synthetic essential oils, and as flavor-modifying ingredients for the manufacture of artificial flavors or for the aromatization of foodstuffs, animal feeds, pharmaceutical preparations or tobacco products.Process for preparing said alicyclic compounds.Type: GrantFiled: May 21, 1974Date of Patent: November 23, 1976Assignee: Firmenich S.A.Inventors: Alan Francis Thomas, Gunther Ohloff
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Patent number: 3989857Abstract: Various compounds are disclosed to be useful in the flavoring of tobacco products. Many of said compounds are also useful as odoriferous ingredients and/or as flavoring agents in general for foodstuffs, beverages and pharmaceutical preparations. The flavorants are cycloaliphatic ketones of which 4,4,6-trimethyl cyclohexa-2,5-dien-2-ol-1-one is an example. They are added in amounts of between 1 to 1000 parts per million parts of flavored product.Type: GrantFiled: June 24, 1974Date of Patent: November 2, 1976Assignee: Firmenich S.A.Inventor: Edouard Demole
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Patent number: 3988432Abstract: Flavor and fragrant compositions comprising a synthetic substitute for steam-distilled lime oil are disclosed along with a method of preparing the synthetic substitute.Type: GrantFiled: November 9, 1973Date of Patent: October 26, 1976Assignee: Colgate-Palmolive CompanyInventor: Robert John Steltenkamp
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Patent number: 3988482Abstract: Water-soluble menthol glycosides are prepared by condensing menthol with a mono- or oligosaccharide, preferably a mono- or disaccharide, i.e., a sugar, or acyl derivative thereof, using a condensing agent or catalyst as needed. These glycosides are hydrolyzed by carbohydrase enzymes, as occur in the human mouth, or common acids, releasing menthol, and provide a more persistent flavor than menthol alone.Type: GrantFiled: September 20, 1974Date of Patent: October 26, 1976Assignee: Toyo Hakka Kogyo Kabushiki KaishaInventors: Tatsuo Higashiyama, Isao Sakata
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Patent number: 3984579Abstract: Methods are described for producing mixtures containing greater than 50% 2-methyl-cis-3-pentenoic acid as well as substantially pure 2-methyl-cis-3-pentenoic acid for preparing foodstuffs, flavoring compositions for foodstuffs, chewing gum compositions, flavoring compositions for chewing gum, medicinal product compositions and ingredients for medicinal product compositions by including therein the isomeric mixtures containing greater than 50% cis-2-methyl-3-pentenoic acid produced by the above-stated processes in order to produce in foodstuff flavorings, medicinal product flavorings and chewing gum flavorings, a sweet, fruity, strawberry, winey-cognac, butter-like, rum-like and butterscotch aroma and a sweet, strawberry, nutty-coconut, fatty, butter-like, rum-like and butterscotch-like taste with fruity, coconut-like isovaleric undertones.Type: GrantFiled: May 9, 1975Date of Patent: October 5, 1976Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Manfred Hugo Vock, Joaquin Vinals, Edward J. Shuster
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Patent number: 3978242Abstract: An Italico-cheese flavor is given to a foodstuff by the addition of a flavor composition comprising 2-phenyl ethanol and methyl-1-butanols. Addition of the flavor composition is particularly useful when the foodstuff is young Cheddar cheese.Type: GrantFiled: March 26, 1975Date of Patent: August 31, 1976Assignee: Lever Brothers CompanyInventors: Wolfram Gustav Freytag, Karl Heinz Ney, I. Poetoe Gde Wirotama
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Patent number: 3978009Abstract: New cycloaliphatic compounds useful as perfuming and odor-modifying agents in the manufacture of perfumes and perfumed products, and as flavoring and taste-modifying agents in the aromatization of foodstuffs in general and imitation flavors for foodstuffs, beverages, animal feeds, pharmaceutical preparations and tobacco products.Novel process for the preparation of said cyclo-aliphatic compounds and compositions of matter relating to mixtures containing same.Type: GrantFiled: May 30, 1975Date of Patent: August 31, 1976Assignee: Firmenich S.A.Inventor: Karl-Heinrich Schulte-Elte
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Patent number: 3976790Abstract: A group of novel dihydrochalcone compounds represented by the formula ##SPC1##Wherein M is hydrogen or a pharmacologically acceptable cation and R is a lower saturated alkyl of from 1 to 4 carbon atoms, and their use as sweetening agents in food products are disclosed.Type: GrantFiled: June 10, 1974Date of Patent: August 24, 1976Assignee: DynapolInventors: Guy A. Crosby, Grant E. DuBois
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Patent number: 3968264Abstract: Enhancement of the flavor of foodstuffs is achieved by the addition of an effective flavor-modifying amount of an aromatic sulfur compound of the formula: ##SPC1##Wherein R.sub.1 is hydrogen, hydroxy, alkoxy or alkyl and R.sub.2 is hydrogen or alkyl; ##SPC2##Wherein R.sub.1 is hydrogen, hydroxy, alkyl or alkoxy, R.sub.2 is hydrogen or alkyl, R.sub.3 is alkyl or benzyl and n is 0, 1, Or 2; and ##SPC3##Wherein R is alkyl or phenyl.Type: GrantFiled: June 24, 1974Date of Patent: July 6, 1976Assignee: Firmenich & CieInventors: Max Winter, Fritz Gautschi, Ivon Flament, Max Stoll, Irving M. Goldman