Carbocyclic Patents (Class 426/538)
  • Patent number: 4131687
    Abstract: 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: Grant
    Filed: January 27, 1978
    Date of Patent: December 26, 1978
    Assignee: 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
  • Patent number: 4130508
    Abstract: 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: Grant
    Filed: December 13, 1977
    Date of Patent: December 19, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Bette M. Spencer, Joaquin F. Vinals, Jacob Kiwala, Manfred H. Vock, Edward J. Shuster
  • Patent number: 4128101
    Abstract: 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: Grant
    Filed: May 10, 1977
    Date of Patent: December 5, 1978
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Kurt Kulka, Frank Mild, Frank Fischetti, Jr.
  • Patent number: 4126570
    Abstract: 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: Grant
    Filed: December 13, 1977
    Date of Patent: November 21, 1978
    Assignee: 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
  • Patent number: 4122120
    Abstract: 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: Grant
    Filed: July 28, 1977
    Date of Patent: October 24, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
  • Patent number: 4119106
    Abstract: 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: Grant
    Filed: October 1, 1976
    Date of Patent: October 10, 1978
    Assignee: Philip Morris, Incorporated
    Inventors: Harvey J. Grubbs, Thomas V. Van Auken, William R. Johnson, Jr.
  • Patent number: 4119574
    Abstract: 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: Grant
    Filed: November 15, 1977
    Date of Patent: October 10, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Bette M. Spencer, Joaquin F. Vinals, Jacob Kiwala, Manfred Hugo Vock, Edward J. Shuster
  • Patent number: 4118343
    Abstract: 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: Grant
    Filed: August 15, 1977
    Date of Patent: October 3, 1978
    Assignee: Firmenich, S.A.
    Inventors: Werner Skorianetz, Gunther Ohloff
  • Patent number: 4114630
    Abstract: 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: Grant
    Filed: October 21, 1976
    Date of Patent: September 19, 1978
    Assignee: Firmenich SA
    Inventors: Walter Renold, Werner Skorianetz, Karl-Heinrich Schulte-Elte, Gunther Ohloff
  • Patent number: 4109022
    Abstract: 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: Grant
    Filed: April 28, 1976
    Date of Patent: August 22, 1978
    Assignee: P.F.W. Beheer B.V.
    Inventors: Douwe Rienk de Haan, Dirk Karel Kettenes
  • Patent number: 4107093
    Abstract: 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: Grant
    Filed: July 28, 1977
    Date of Patent: August 15, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
  • Patent number: 4107094
    Abstract: 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: Grant
    Filed: September 19, 1977
    Date of Patent: August 15, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Manfred Hugo Vock, Edward J. Shuster, Frederick Louis Schmitt
  • Patent number: 4107209
    Abstract: 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, slightly
    Type: Grant
    Filed: March 3, 1977
    Date of Patent: August 15, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard A. Wilson, Braja Dulal Mookherjee, Anne Sanderson Hruza, Manfred Hugo Vock, Louis Schmitt Frederick, Joaquin Francisco Vinals
  • Patent number: 4103036
    Abstract: 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: Grant
    Filed: July 28, 1977
    Date of Patent: July 25, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
  • Patent number: 4097416
    Abstract: 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: Grant
    Filed: August 24, 1977
    Date of Patent: June 27, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals, Robert M. Novak
  • Patent number: 4093565
    Abstract: 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: Grant
    Filed: March 18, 1976
    Date of Patent: June 6, 1978
    Assignee: Colgate-Palmolive Company
    Inventor: Robert John Steltenkamp
  • Patent number: 4089986
    Abstract: 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: Grant
    Filed: September 19, 1977
    Date of Patent: May 16, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Manfred Hugo Vock, Edward J. Shuster, Frederick Louis Schmitt
  • Patent number: 4084009
    Abstract: 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: Grant
    Filed: March 3, 1977
    Date of Patent: April 11, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Bette M. Spencer, Joaquin F. Vinals, Jacob Kiwala, Manfred Hugo Vock, Edward J. Shuster
  • Patent number: 4081479
    Abstract: 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: Grant
    Filed: December 22, 1976
    Date of Patent: March 28, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker, Frederick Louis Schmitt, Manfred Hugo Vock
  • Patent number: 4076854
    Abstract: 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: Grant
    Filed: March 3, 1977
    Date of Patent: February 28, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Bette M. Spencer, Joaquin F. Vinals, Jacob Kiwala, Manfred Hugo Vock, Edward J. Shuster
  • Patent number: 4076853
    Abstract: 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: Grant
    Filed: February 4, 1977
    Date of Patent: February 28, 1978
    Assignee: 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
  • Patent number: 4073751
    Abstract: 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: Grant
    Filed: February 4, 1977
    Date of Patent: February 14, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker, Frederick L. Schmitt, Manfred H. Vock
  • Patent number: 4068012
    Abstract: 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: Grant
    Filed: November 11, 1976
    Date of Patent: January 10, 1978
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals, Robert M. Novak
  • Patent number: 4064281
    Abstract: 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: Grant
    Filed: February 4, 1977
    Date of Patent: December 20, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker, Frederick Louis Schmitt, Manfred Hugo Vock
  • Patent number: 4064184
    Abstract: 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: Grant
    Filed: November 11, 1976
    Date of Patent: December 20, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Manfred Hugo Vock, Edward J. Shuster, Frederick Louis Schmitt
  • Patent number: 4062894
    Abstract: 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: Grant
    Filed: August 11, 1976
    Date of Patent: December 13, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Manfred Hugo Vock, Frederick Louis Schmitt, John B. Hall, James Milton Sanders
  • Patent number: 4053657
    Abstract: 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: Grant
    Filed: December 3, 1976
    Date of Patent: October 11, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William L. Schreiber, James N. Siano, Manfred Hugo Vock, Edward J. Shuster
  • Patent number: 4048120
    Abstract: 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: Grant
    Filed: May 26, 1976
    Date of Patent: September 13, 1977
    Assignee: Firmenich S.A.
    Inventor: Valentin Rautenstrauch
  • Patent number: 4044164
    Abstract: 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: Grant
    Filed: October 7, 1976
    Date of Patent: August 23, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William J. Evers, Howard H. Heinsohn, Jr., Manfred Hugo Vock
  • Patent number: 4036886
    Abstract: 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: Grant
    Filed: April 12, 1976
    Date of Patent: July 19, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: William Lewis Schreiber, Gerard Joseph Mosciano, Alan O. Pittet, Manfred Vock, Edward Joseph Shuster
  • Patent number: 4033994
    Abstract: 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: Grant
    Filed: July 8, 1974
    Date of Patent: July 5, 1977
    Assignee: Wilkinson Sword Limited
    Inventors: Hugh R. Watson, David G. Rowsell, John H. D. Browning
  • Patent number: 4029106
    Abstract: 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: Grant
    Filed: June 12, 1975
    Date of Patent: June 14, 1977
    Assignee: Firmenich S.A.
    Inventor: Edouard Demole
  • Patent number: 4021494
    Abstract: 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: Grant
    Filed: August 11, 1976
    Date of Patent: May 3, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Kenneth K. Light, Edward J. Shuster, Joaquin F. Vinals, Manfred Hugo Vock
  • Patent number: 4021488
    Abstract: 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: Grant
    Filed: August 11, 1976
    Date of Patent: May 3, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker, Frederick Louis Schmitt, Manfred Hugo Vock
  • Patent number: 4011270
    Abstract: 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: Grant
    Filed: May 28, 1974
    Date of Patent: March 8, 1977
    Assignee: I. P. Callison & Sons, Inc.
    Inventor: Richard Gardner Carrington
  • Patent number: 4001453
    Abstract: 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: Grant
    Filed: September 19, 1974
    Date of Patent: January 4, 1977
    Assignee: Givaudan Corporation
    Inventors: Ulrich Huber, Nicolas Kosslakoff, Bruno Vaterlaus
  • Patent number: 4000329
    Abstract: 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: Grant
    Filed: March 1, 1976
    Date of Patent: December 28, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals
  • Patent number: 3998974
    Abstract: 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: Grant
    Filed: June 6, 1975
    Date of Patent: December 21, 1976
    Assignee: Dynapol Corporation
    Inventor: Alejandro Zaffaroni
  • Patent number: 3996296
    Abstract: 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: Grant
    Filed: March 24, 1975
    Date of Patent: December 7, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Braja Dulal Mookherjee, Manfred Hugo Vock, Carlos Benaim, Edward J. Shuster
  • Patent number: 3993604
    Abstract: 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: Grant
    Filed: May 21, 1974
    Date of Patent: November 23, 1976
    Assignee: Firmenich S.A.
    Inventors: Alan Francis Thomas, Gunther Ohloff
  • Patent number: 3989857
    Abstract: 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: Grant
    Filed: June 24, 1974
    Date of Patent: November 2, 1976
    Assignee: Firmenich S.A.
    Inventor: Edouard Demole
  • Patent number: 3988482
    Abstract: 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: Grant
    Filed: September 20, 1974
    Date of Patent: October 26, 1976
    Assignee: Toyo Hakka Kogyo Kabushiki Kaisha
    Inventors: Tatsuo Higashiyama, Isao Sakata
  • Patent number: 3988432
    Abstract: 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: Grant
    Filed: November 9, 1973
    Date of Patent: October 26, 1976
    Assignee: Colgate-Palmolive Company
    Inventor: Robert John Steltenkamp
  • Patent number: 3984579
    Abstract: 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: Grant
    Filed: May 9, 1975
    Date of Patent: October 5, 1976
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Manfred Hugo Vock, Joaquin Vinals, Edward J. Shuster
  • Patent number: 3978242
    Abstract: 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: Grant
    Filed: March 26, 1975
    Date of Patent: August 31, 1976
    Assignee: Lever Brothers Company
    Inventors: Wolfram Gustav Freytag, Karl Heinz Ney, I. Poetoe Gde Wirotama
  • Patent number: 3978009
    Abstract: 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: Grant
    Filed: May 30, 1975
    Date of Patent: August 31, 1976
    Assignee: Firmenich S.A.
    Inventor: Karl-Heinrich Schulte-Elte
  • Patent number: 3976790
    Abstract: 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: Grant
    Filed: June 10, 1974
    Date of Patent: August 24, 1976
    Assignee: Dynapol
    Inventors: Guy A. Crosby, Grant E. DuBois
  • Patent number: 3968264
    Abstract: 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: Grant
    Filed: June 24, 1974
    Date of Patent: July 6, 1976
    Assignee: Firmenich & Cie
    Inventors: Max Winter, Fritz Gautschi, Ivon Flament, Max Stoll, Irving M. Goldman
  • Patent number: 3968070
    Abstract: Process for the preparation of 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.Composition of matter relating to some of said cycloaliphatic compounds which are new and perfume- and flavoring compositions containing same.
    Type: Grant
    Filed: December 2, 1974
    Date of Patent: July 6, 1976
    Assignee: Firmenich S.A.
    Inventor: Erling Sundt
  • Patent number: 3966986
    Abstract: A method for enhancing the flavor and aroma of a final tea beverage prepared from a soluble tea, e.g., a concentrated tea extract or a dried soluble tea, by adding a flavoring agent to the soluble tea to produce a final tea beverage containing about 0.01-25 ppm of the added flavoring agent. The flavoring agent, having different preferred compositions for cold and hot-water soluble products, includes up to 39 selected flavoring constituents in specified amounts.
    Type: Grant
    Filed: October 29, 1974
    Date of Patent: June 29, 1976
    Assignee: Tenco Brooke Bond Limited
    Inventors: George L. K. Hunter, Victor Krampl, Charles Thomas Malone, Gerald Edward Usher