Oxygen Single Bonded Directly To The Ring System Patents (Class 512/19)
  • Patent number: 11725161
    Abstract: The present invention has an object of providing a carboxylate compound that is useful as a raw material for fragrance compositions and has a fruity aroma, a method for producing the same, and a fragrance composition containing the carboxylate compound. The carboxylate compound of the present invention is represented by Formula (1). where, R is an alkyl group having from 2 to 6 carbons.
    Type: Grant
    Filed: November 7, 2019
    Date of Patent: August 15, 2023
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yutaka Matsuura, Tatsuya Utamura, Tomohiko Hakamata
  • Patent number: 10584080
    Abstract: Disclosed is a cyclopropanation process comprising the step of reacting an alkene compound having at least one carbon-carbon double bond with at least one dihaloalkane. The reaction is carried out in the presence of (i) particulate metal Zn, (ii) catalytically effective amount of particulate metal Cu or a salt thereof, (iii) at least one haloalkylsilane, and (iv) at least one solvent.
    Type: Grant
    Filed: February 1, 2019
    Date of Patent: March 10, 2020
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad Gara, Yigal Becker
  • Patent number: 10227269
    Abstract: Disclosed is a cyclopropanation process comprising the step of reacting an alkene compound having at least one carbon-carbon double bond with at least one dihaloalkane. The reaction is carried out in the presence of (i) particulate metal Zn, (ii) catalytically effective amount of particulate metal Cu or a salt thereof, (iii) at least one haloalkylsilane, and (iv) at least one solvent.
    Type: Grant
    Filed: August 4, 2016
    Date of Patent: March 12, 2019
    Assignee: International Flavors & Fragances Inc.
    Inventors: Mohamad Gara, Yigal Becker
  • Publication number: 20150080265
    Abstract: Compositions which are fragrant and contain at least a member set culled from a library of compositions, each being comprised of sub-combinations of selected terpenes. Fragrances that mimic that of various states of organic and synthetic aromatics including products, processes and those from non-combusted plant products, among other things, uniquitous products, processes, medicinals, and related moieties leverage databases of all known terpene groupings are offered for consideration, and have been provided, according to the instant teachings.
    Type: Application
    Filed: August 25, 2014
    Publication date: March 19, 2015
    Inventors: Sytze Elzinga, Jeffrey C. Raber
  • Patent number: 8883468
    Abstract: (3S,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-octahydroazulen-1-ols, their use as flavor or fragrance ingredient, and a process of their production by oxidation in the presence of laccase.
    Type: Grant
    Filed: June 28, 2011
    Date of Patent: November 11, 2014
    Assignee: Givaudan S.A.
    Inventors: Boris Schilling, Thierry Granier, Esther Locher
  • Patent number: 8846651
    Abstract: It is to provide a technique for preventing aggregation or caking of menthol at the time of its keeping. In addition, it is to provide a lipid composition, which can show excellent thermal stability even in the case of high temperature at the time of keeping menthol and at the time of blending in a product, does not cause mutual aggregation of powders, particles, flakes, pellets, sticks and the like of menthol, and can maintain its shape retention property. From 10 to 50% by mass of sterols are added to and mixed with from 50 to 90% by mass of menthol, and the resultant is melted with heating. Paraffins may be further added and mixed in an amount of 20% by mass or less, based on the lipid composition.
    Type: Grant
    Filed: February 27, 2008
    Date of Patent: September 30, 2014
    Assignee: Takasago International Corporation
    Inventors: Kenya Ishida, Chiyomi Birou, Tetsuya Yamamoto
  • Publication number: 20130287707
    Abstract: As a novel compound which is excellent in odor quality and has an odor of a very clear and strong woody note, the invention provides a compound represented by the following formula (1):
    Type: Application
    Filed: April 19, 2013
    Publication date: October 31, 2013
    Applicant: Takasago International Corporation
    Inventors: Kyoko ZAIZEN, Tsuyoshi Kobayashi, Junko Nagano, Yoshihiro Yaguchi
  • Publication number: 20130089904
    Abstract: (3S,5R)-3,8-dimethyl-5-(prop-1-en-2-yl)-octahydroazulen-1-ols, their use as flavour or fragrance ingredient, and a process of their production by oxidation in the presence of laccase.
    Type: Application
    Filed: June 28, 2011
    Publication date: April 11, 2013
    Applicant: GIVAUDAN S.A.
    Inventors: Boris Schilling, Thierry Granier, Esther Locher
  • Publication number: 20130065807
    Abstract: The present invention primarily relates to fragrance substance mixtures, preferably perfume oils, comprising (a) compound (A-1) and compound (A-2) and (b) one or more further musk fragrance substances, which are not isolongifolenyl methyl ethers, wherein the mass ratio of the total quantity of musk fragrance substances of constituent (b) to the total quantity of compounds (A-1) and (A-2) (constituent (a)) is preferably greater than or equal to 1:2. Furthermore, the present invention relates to perfumed products containing fragrance substance mixtures of this type according to the invention, in particular perfume oils, and a method for modifying certain olfactory properties of fragrance substances, fragrance substance mixtures, perfume oils or correspondingly perfumed products.
    Type: Application
    Filed: September 7, 2012
    Publication date: March 14, 2013
    Applicant: SYMRISE AG
    Inventors: Marcus Eh, Pierre Kurzenne, Marc vom Ende, Emilie Coppermann
  • Patent number: 8309511
    Abstract: The present invention is directed to novel fragrance compounds and their unexpected advantageous use in enhancing, improving or modifying a fragrance formulation through the addition of an olfactory acceptable amount of the compounds, wherein the compounds are represented by the following formula: wherein a methyl group is bonded to the 5-membered ring at position 2 or 3, or a mixture thereof.
    Type: Grant
    Filed: May 22, 2012
    Date of Patent: November 13, 2012
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard A. Weiss, Anubhav P. S. Narula, James Anthony Lasome, Richard M. Boden
  • Patent number: 8071529
    Abstract: The present invention relates to novel compounds and their use in fragrance compositions. Novel 3.2.1-bicyclo-octene and -octane compounds of the present invention are represented by formula: wherein R is selected from the group consisting of hydrogen, acetate, carbonate monomethyl ester, and allyloxy; and wherein the broken line represents a single or double bond.
    Type: Grant
    Filed: October 8, 2010
    Date of Patent: December 6, 2011
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Adam P. Closson, Benjamin Amorelli, Nicole O'Keefe
  • Patent number: 7973200
    Abstract: The invention relates to the use as perfuming ingredients of 8a-alkyl-perhydro-naphthalenol derivatives, to impart odor notes of the woody-earthy type.
    Type: Grant
    Filed: October 29, 2008
    Date of Patent: July 5, 2011
    Assignee: Firmenich SA
    Inventors: Robert Moretti, Olivier Etter
  • Publication number: 20110092604
    Abstract: The present invention relates to fragrance substance mixtures, in particular perfume oils, comprising (a) compound (A) and (b) at least one musk fragrance substance wherein the mass ratio of the total quantity of the musk fragrance substance or substances of component (b) to compound (A) is greater than or equal to 1:1. The present invention also relates to perfumed products comprising fragrance substance mixtures of this type according to the invention, in particular perfume oils, and to a process for the production of the fragrance substance mixtures and perfume oils according to the invention.
    Type: Application
    Filed: October 19, 2010
    Publication date: April 21, 2011
    Applicant: SYMRISE AG
    Inventors: Ingo Wöhrle, Marcus Eh, Marinus Cornelius Van Dijk
  • Patent number: 7902142
    Abstract: Provided is a fragrance composition containing 8- drimanol represented by the formula (Ia): and containing none of 7-acetyl-1,2,3,4,5,6,7,8-octahydro- 1,1,6,7-tetramethylnaphthalene, 1,2,3,4,4a,5,6,7-octahydro- 2,5,5-trimethyl-2-naphthalenol, 1,2,3,4,4a,7,8,8a- octahydro-2,4a,5,8a-tetramethyl-l-naphthylformate, 3a-ethyldodecahydro-6, 6,9a-trimethylnaphtho[2,1-b]furan, and racemic and optically-active substance of dodecahydro- 3a,6,6,9a-tetramethylnaphtho[2,1-b]furan; and personal care products, household products and environmental hygiene products containing the composition. The fragrance composition of the present invention contains 8-drimanol (Ia) so that it can produce various novel odors and emit a odor with softness and warmth typical to natural ambergris.
    Type: Grant
    Filed: July 24, 2006
    Date of Patent: March 8, 2011
    Assignee: Kao Corporation
    Inventors: Kazuyuki Fukuda, Naotoshi Toki
  • Publication number: 20100209372
    Abstract: The invention relates to the use as perfuming ingredients of 8a-alkyl-perhydro-naphthalenol derivatives, to impart odor notes of the woody-earthy type.
    Type: Application
    Filed: October 29, 2008
    Publication date: August 19, 2010
    Inventors: Robert Moretti, Olivier Etter
  • Patent number: 7763238
    Abstract: Deodorant compositions are disclosed comprising a cross-adapting agent, alone or in combination with other such agents, in an amount effective to reduce perception of malodor. Deodorant compositions are also disclosed comprising a cross-adapting agent, alone or in combination with other such agents, in an amount effective to reduce perception of gender-specific malodor. The methods feature reducing perceived body odor comprising administering a deodorant composition wherein the composition comprises an amount of cross-adapting agent effective to reduce perception of such odor. Other methods feature blocking perceived body odor comprising administering a deodorant composition wherein the composition comprises an amount of cross-adapting agent effective to occupy an odorant receptor site, thereby blocking interaction of the site with other odorants.
    Type: Grant
    Filed: January 15, 2003
    Date of Patent: July 27, 2010
    Assignees: Monell Chemical Senses Center, Symrise Inc.
    Inventors: George Preti, Charles J. Wysocki, Leslie C. Smith, Keith J. McDermott
  • Patent number: 7704942
    Abstract: The invention relates to phenyl-cycloalkanes of formula (I) wherein the groups R1 to R6 are defined in the specification.
    Type: Grant
    Filed: June 28, 2002
    Date of Patent: April 27, 2010
    Assignee: Givaudan SA
    Inventor: Andreas Goeke
  • Publication number: 20100093682
    Abstract: It is to provide a technique for preventing aggregation or caking of menthol at the time of its keeping. In addition, it is to provide a lipid composition, which can show excellent thermal stability even in the case of high temperature at the time of keeping menthol and at the time of blending in a product, does not cause mutual aggregation of powders, particles, flakes, pellets, sticks and the like of menthol, and can maintain its shape retention property. From 10 to 50% by mass of sterols are added to and mixed with from 50 to 90% by mass of menthol, and the resultant is melted with heating. Paraffins may be further added and mixed in an amount of 20% by mass or less, based on the lipid composition.
    Type: Application
    Filed: February 27, 2008
    Publication date: April 15, 2010
    Applicant: TAKASAGO INTERNATIONAL CORPORATION
    Inventors: Kenya Ishida, Chiyomi Birou, Tetsuya Yamamoto
  • Patent number: 7592492
    Abstract: The present invention relates to the use as perfuming ingredients of certain derivatives of perhydro-1-naphthalenol of formula: wherein, in particular, each R represents a hydrogen atom or a methyl group, R1 and R3 represent a methyl or ethyl group, and R2 represents a hydrogen atom or a lower acyl group.
    Type: Grant
    Filed: May 3, 2007
    Date of Patent: September 22, 2009
    Assignee: Firmenich SA
    Inventors: Robert Moretti, Olivier Etter
  • Patent number: 7538081
    Abstract: A fragrance composition having an excellent diffusivity and long-lasting property of fragrance and a cosmetic, toiletry, bath composition, food and drink and pharmaceutical having an excellent diffusivity and long-lasting property of fragrance by using a novel fixative. A compound represented by the following general formula (1) is incorporated in a fragrance composition or the foregoing products. The amount of the compound of the general formula (1) to be incorporated in the fragrance composition is preferably from 0.01 to 90% by weight. The amount of the compound of the general formula (1) to be incorporated directly in the foregoing products is preferably from 0.0001 to 2.0 times (by weight) the weight of the aroma composition and/or composition to be incorporated therein. In this arrangement, a fragrance composition or products having an enhanced diffusivity and long-lasting property of fragrance can be obtained without causing any safety problem on human being.
    Type: Grant
    Filed: September 12, 2001
    Date of Patent: May 26, 2009
    Assignee: Takasago International Corporation
    Inventors: Kenya Ishida, Takashi Nishida, Hiroyuki Matsuda, Hisao Iwai, Toshimitsu Hagiwara
  • Publication number: 20090130043
    Abstract: The present invention relates to the use as perfuming ingredients of certain derivatives of perhydro-1-naphthalenol of formula: wherein, in particular, each R represents a hydrogen atom or a methyl group, R1 and R3 represent a methyl or ethyl group, and R2 represents a hydrogen atom or a lower acyl group.
    Type: Application
    Filed: May 3, 2007
    Publication date: May 21, 2009
    Inventors: Robert Moretti, Olivier Etter
  • Publication number: 20090123404
    Abstract: Provided is a fragrance composition containing 8-drimanol represented by the formula (1a): and containing none of 7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethylnaphthalene, 1,2,3,4,4a,5,6,7-octahydro-2,5,5-trimethyl-2-naphthalenol, 1,2,3,4,4a,7,8,8a-octahydro-2,4a,5,8a-tetramethyl-1-naphthylformate, 3a-ethyldodecahydro-6,6,9a-trimethylnaphtho[2,1-b]furan, and racemic and optically-active substance of dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan; and personal care products, household products and environmental hygiene products containing the composition. The fragrance composition of the present invention contains 8-drimanol (1a) so that it can produce various novel odors and emit a odor with softness and warmth typical to natural ambergris.
    Type: Application
    Filed: July 24, 2006
    Publication date: May 14, 2009
    Applicant: KAO CORPORATION
    Inventors: Kazuyuki Fukuda, Naotoshi Toki
  • Publication number: 20090075859
    Abstract: A fragrance composition containing 0.0005 to 10% by mass of a decalin alcohol as component (a) represented by formula (1a) and 90 to 99.9995% by mass of one or more polycyclic woody-amber fragrances as component (b) selected from the group consisting of 7-acetyl-1,2,3,4,5,6,7,8-octahydro-1,1,6,7-tetramethylnaphthalene, 1,2,3,4,4a,5,6,7-octahydro-2,5,5-trimethyl-2-naphthalenol, 1,2,3,4,4a,7,8,8a-octahydro-2,4a,5,8a-tetramethyl-1-naphthyl formate, 3a-ethyldodecahydro-6,6,9a-trimethylnaphtho[2,1-b]furan, and racemic or optically active dodecahydro-3a,6,6,9a-tetramethylnaphtho[2,1-b]furan; and a cosmetic product, a household product and an environmental/sanitary product containing the fragrance composition. The fragrance composition of the present invention is a highly versatile fragrance composition that brings about an odor of natural ambergris and can attain effects to enhance warmth and an odor quality even in a small amount.
    Type: Application
    Filed: June 29, 2006
    Publication date: March 19, 2009
    Applicant: KAO CORPORATION
    Inventors: Naotoshi Toki, Kosaku Ishida, Kazuyuki Fukuda
  • Publication number: 20080274927
    Abstract: The present invention relates to substituted bicyclo[3.3.1]nonanes and bicyclo[3.3.1]nonenes of formula (I) wherein R, and R1 to R5 have the same meaning as described in the specification.
    Type: Application
    Filed: January 14, 2005
    Publication date: November 6, 2008
    Applicant: GIVAUDAN SA
    Inventors: Thierry Granier, Andreas Hanhart, Jerzy A. Bajgrowicz
  • Patent number: 7378383
    Abstract: The present invention relates to the use as perfuming ingredient of a decaline derivative of formula wherein R1 is a lower alkyl, the R2 to R5 are hydrogen atoms or lower alkyls and at least one dotted line is a double bond, which is a useful perfuming ingredient of the woody or woody-citrus type.
    Type: Grant
    Filed: May 6, 2005
    Date of Patent: May 27, 2008
    Assignee: Firmenich SA
    Inventors: Robert Moretti, Olivier Etter
  • Patent number: 7312187
    Abstract: Described are polyalkylbicylic chemical derivatives for use a fragrance ingredients having the generic structure: wherein m=0 or 1; wherein X is methyl or hydrogen; wherein R1, R2, R3 and R4 each represents methyl or ethyl with the proviso that when X is methyl, each of R1, R2, R3 and R4 is methyl and when X is hydrogen, one of R1, R2, R3 and R4 is ethyl; and wherein R6 represents hydrogen or methyl. Methods for using and making these compounds are also disclosed.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: December 25, 2007
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, Edward Mark Arruda
  • Patent number: 7250528
    Abstract: The present invention relates to a process for making indenol esters or ethers from an ?-substituted cinnamic aldehyde derivative such as an acetal or an acylal. Said reaction is promoted by the use of strong mineral acids, sulphonic acids, acidic zeolites or Lewis acids.
    Type: Grant
    Filed: October 12, 2006
    Date of Patent: July 31, 2007
    Assignee: Firmenich SA
    Inventors: Gary Bernard Womack, Roger Leslie Snowden, Hervé Mosimann, Anthony Alexander Birkbeck
  • Patent number: 7232795
    Abstract: The present invention is directed to novel substituted cyclopropane ethers compounds of the general formulae selected from the group consisting of R and R1 independently represent a hydrogen or a straight, branched, or cyclic hydrocarbon moiety consisting of less then 15 carbon atoms and containing single and/or double bonds.
    Type: Grant
    Filed: November 23, 2005
    Date of Patent: June 19, 2007
    Inventors: Anubhav P. S. Narula, Edward Mark Arruda, Franc T. Schiet
  • Patent number: 6734159
    Abstract: Cyclic isolongifolenyl ethers of the general formula A, where wavy lines mean &agr;- and &bgr;-configuration, and R is the following radicals. R=Me, Et, Pr, iso-Pr, Bu, sec-Bu, iso-Bu, tert-Bu. These isolongifolenyl ethers are excellent fragrances and can, in particular, be used as a constituent of fragrance mixtures or perfume oil for the perfuming of cosmetic or technical consumer goods. Also described are processes for the preparation of said cyclic isolongifolenyl ethers.
    Type: Grant
    Filed: March 25, 2003
    Date of Patent: May 11, 2004
    Assignee: Symrise GmbH & Co. KG
    Inventors: Wilhelm Pickenhagen, Dietmar Schatkowski
  • Patent number: 6653276
    Abstract: A composition comprising at least 60% by weight, based on the weight of the composition, of a cyclopentanone or cyclopentanol compound having 2,5-dicyclopentylidene substituents, 2,5-dicyclopentyl substituents or 2-cyclopentylidene-5-cyclopentyl substituents. This composition is useful as perfume emitting floral fragrance. 2,5-Dicyclopentylidenecyclopentane (compound 4) is prepared by reaction of 2-cyclopentylidenecyclopentanone with cyclopentanone. 2,5-Dicyclopentylcyclopentanone (compound 5) and 2,5-dicyclopentylidenecyclopentanol (compound 6) are prepared by reduction of compound 4. 2,5-Dicyclopentylcyclopentanol (compound 7) is prepared by reduction of compound 5 or compound 6.
    Type: Grant
    Filed: May 23, 2001
    Date of Patent: November 25, 2003
    Assignee: Zeon Corporation
    Inventors: Masafumi Yamada, Hiroshi Fujisawa
  • Patent number: 6566562
    Abstract: The invention relates to the preparation of the compounds isolongifolanol (IUPAC name: 2,2,7,7-tetramethyltricyclo[6.2.1.01,6]undecan-6-ol) and isolongifolenol (IUPAC name: 2,2,7,7-tetramethyltricyclo[6.2.1.01,6]undec4-en-6-ol) and to the use thereof as fragrance or aroma substance.
    Type: Grant
    Filed: December 11, 2001
    Date of Patent: May 20, 2003
    Assignee: Haarmann & Reimer GmbH
    Inventors: Ingo Wöhrle, Jürgen Nienhaus
  • Patent number: 6362378
    Abstract: The present invention relates to a process for etherification of a benzyl type alcohol, to the products obtained and to their applications, in particular in the perfumery field. The etherification process of the invention consists of reacting a benzyl type alcohol with another alcohol in the presence of a catalyst, characterized in that the etherification reaction is carried out in the presence of an effective quantity of a zeolite.
    Type: Grant
    Filed: March 14, 2000
    Date of Patent: March 26, 2002
    Assignee: Rhodia Chimie
    Inventors: Roland Jacquot, Michel Spagnol
  • Patent number: 6271193
    Abstract: Described are carbon-containing functional groups substituted 4,5,6,7-tetrahydro-polyalkylated-4-indanes, isomers thereof, process for processes for preparing same, and uses thereof. The 4,5,6,7-tetrahydro-polyalkylated-4-indanes have the generic structure: Wherein G and R1-5 are as defined in the specification. The aforementioned materials have fragrance properties or are intermediates for materials which have fragrance properties. Also described are processes for producing the aforementioned substances.
    Type: Grant
    Filed: October 11, 2000
    Date of Patent: August 7, 2001
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Richard A. Weiss, Anthony T. Levorse, Jr., Howard H. Heinsohn, Jr., Charles E. J. Beck, Marie R. Hanna
  • Patent number: 6214788
    Abstract: The use of (−)-cubebol, or (−)-(1R,4S,5R,6R,7S,10R)-7-isopropyl-4, 10-dimethyl-tricyclo[4.4.0.0(1,5)]decan-4-ol of the formula as a flavoring, and the foods and various other products flavored with cubebol.
    Type: Grant
    Filed: March 28, 2000
    Date of Patent: April 10, 2001
    Assignee: Firmenich SA
    Inventors: Maria Inés Velazco, Laurent Wuensche, Patrice Deladoey
  • Patent number: 6162954
    Abstract: The invention relates to compounds of the general formula ##STR1## in which R.sup.1 to R.sup.7 are, independently, H, methyl or ethyl, R.sup.8 +R.sup.9 together form methylene (--CH.sub.2 --) or a single bond, or R.sup.1 +R.sup.2 together form --(CH.sub.2).sub.n --, with n being 3 or 4, or R.sup.3 +R.sup.5 or R.sup.5 +R.sup.7 represent methylene or a single bond; and the presence of at least one cyclopropane ring in the molecule is compulsory and the side chain can be saturated or contains one double bond in position .alpha.,.beta. or .beta.,.gamma., a process for the manufacture of these compounds, compounds used to perform the process and the use of these compounds as an odorant or as an ingredient of an odorant composition.
    Type: Grant
    Filed: April 21, 1999
    Date of Patent: December 19, 2000
    Assignee: Givaudan Roure (International) SA
    Inventors: Jerzy A. Bajgrowicz, Georg Frater
  • Patent number: 5929291
    Abstract: The invention relates to compounds of the general formula ##STR1## in which R.sup.1 to R.sup.7 are, independently, H, methyl or ethyl, R.sup.8 +R.sup.9 together form methylene (--CH.sub.2 --) or a single bond, or R.sup.1 +R.sup.2 together form --(CH.sub.2).sub.n --, with n being 3 or 4, or R.sup.3 +R.sup.5 or R.sup.5 +R.sup.7 represent methylene or a single bond; and the presence of at least one cyclopropane ring in the molecule is compulsory and the side chain can be saturated or contains one double bond in position .alpha.,.beta. or .beta., .gamma. a process for the manufacture of these compounds, compounds used to perform the process and the use of these compounds as an odorant or as an ingredient of an odorant composition.
    Type: Grant
    Filed: April 9, 1997
    Date of Patent: July 27, 1999
    Assignee: Givaudan Roure (International) SA
    Inventors: Jerzy A. Bajgrowicz, Georg Frater
  • Patent number: 5733866
    Abstract: Described are methyl substituted hexahydroindanols and alkyl ethers thereof defined according to the generic structure: ##STR1## wherein R.sub.7 represents hydrogen or C.sub.1 -C.sub.3 alkyl; wherein R.sub.1 represents methyl or ethyl; wherein R.sub.4 represents methyl or hydrogen; and wherein R.sub.2, R.sub.3, R.sub.5 and R.sub.6 each represents methyl or ethyl with the provisos that:(1) at least three of R.sub.2, R.sub.3, R.sub.5 and R.sub.6 represent methyl; and(2) when each of R.sub.2, R.sub.3, R.sub.5 and R.sub.6 is methyl, then R.sub.4 is methyland uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations.
    Type: Grant
    Filed: August 22, 1996
    Date of Patent: March 31, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, James Joseph Koestler, Marie R. Hanna, Honorine Hattab, Francis Charles Antoine Thibaudeau, Charles E. J. Beck
  • Patent number: 5693606
    Abstract: The described compounds of the general formula A, in which the wavy lines mean .alpha. and .beta. configuration and R.sub.1 and R.sub.2 mean hydrogen, methyl or ethyl groups ##STR1## are new and useful as odorants or components or mixtures of odorants or perfume oils. Their production in a method known per se, involves oxidation of isolongifolene obtained from longifolene to isolongifolane, which is then equilibrated with base extraction and/or reduced to isolongifolan-3-ol and this is then reacted with a symmetric acetal of the formula R.sub.2 --OCHR.sub.1 --O--R.sub.2, in which R.sub.1 is hydrogen or methyl and R.sub.2 is methyl, ethyl or propyl.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: December 2, 1997
    Assignee: DRAGOCO Gerberding & Co. AG
    Inventors: Ernst Joachim Brunke, Dietmar Schatkowski
  • Patent number: 5665698
    Abstract: Described are methyl substituted tetrahydroindane alkyl enol ethers defined according to the structure: ##STR1## wherein R.sub.1 represents methyl or ethyl; wherein R.sub.4 represents methyl or hydrogen; wherein R.sub.2, R.sub.3, R.sub.5 and R.sub.6 each represents methyl or ethyl with the provisos that:(1) at least three of R.sub.2, R.sub.3, R.sub.5 and R.sub.6 represent methyl; and(2) when each of R.sub.2, R.sub.3, R.sub.5 and R.sub.6 is methyl, then R.sub.4 is methyland uses thereof in augmenting, enhancing or imparting an aroma in or to perfume compositions, colognes and perfumed articles including but not limited to perfumed polymers, solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders and hair preparations. Also described are processes for preparing same as well as the process intermediates defined according to the structure: ##STR2## wherein R.sub.7 and R.sub.
    Type: Grant
    Filed: September 6, 1996
    Date of Patent: September 9, 1997
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, James Joseph Koestler, Peter J. Hartong, Marie R. Hanna, Charles E. J. Beck
  • Patent number: 5462923
    Abstract: Described are 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes and mixtures thereof with bicyclopentadiene derivatives, wherein the 1-oxo-substituted and unsubstituted isobutyl-4-ethoxy-benzenes are defined according to the structure: ##STR1## wherein Y.sub.1 represents one of the moieties: ##STR2## and wherein the bicyclopentadiene derivatives are defined according to the structure: ##STR3## wherein Z.sub.1 and Z.sub.2 represent hydrogen, C.sub.1 -C.sub.3 lower alkyl or C.sub.2 -C.sub.3 acyl and Z.sub.3 represents methyl or hydrogen with the proviso that Z.sub.1 and Z.sub.2 are not both hydrogen, and uses thereof in augmenting, enhancing or imparting aromas in and to perfume compositions, colognes, perfumed polymers and perfumed articles.
    Type: Grant
    Filed: September 2, 1994
    Date of Patent: October 31, 1995
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael G. Monteleone, Richard A. Weiss, Mark D. Evans, Marie R. Hanna
  • Patent number: 5366959
    Abstract: Described are mixtures of 2-(2-bornyloxy)-ethyl-1-ethanols defined according to the structure: ##STR1## which represents a mixture wherein in the mixture one of R.sub.1 or R.sub.2 is ethyl and the other of R.sub.1 or R.sub.2 is hydrogen, and organoleptic uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, perfumed polymers, cosmetic powders and hair preparations.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: November 22, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, William L. Schreiber, Joseph A. McGhie, Karen A. Geiger
  • Patent number: 5346885
    Abstract: The compounds of formula ##STR1## wherein symbol X designates a C.dbd.O (Ia) or C(CH.sub.3)--OC(O)CH.sub.3 (Ib) group and the dotted line indicates the location of a single or double bond in formula (Ia) and of a double bond in formula (Ib), are characterised by useful odor notes of the aromatic, fruity, even amber type and can as a result be advantageously used as active perfuming ingredients.
    Type: Grant
    Filed: July 20, 1993
    Date of Patent: September 13, 1994
    Assignee: Firmenich S.A.
    Inventors: Hubert Mimoun, Francois Delay, Philippe Schneider
  • Patent number: 5321007
    Abstract: Described are 2,6-dimethylbicyclo[3.3.1]non-6-ene-3-methanol and substituted derivatives thereof defined according to the generic structure: ##STR1## wherein each of the dashed lines represents a carbon-oxygen covalent bond or no bond; N is 0 or 1; R.sub.1 represents hydrogen, C.sub.1 -C.sub.2 lower alkyl, lower alkenyl, lower alkylenyl, C.sub.1 -C.sub.2 acyl, alkoxycarbonyl, magnesium halo or lithium; and R.sub.2 represents methyl or hydrogen as well as uses thereof (wherein R.sub.1 is not magnesium halo or lithium) for augmenting or enhancing the aroma of consumable materials selected from the group consisting of perfume compositions, perfumed articles, colognes, deodorizing articles, deodorizing compositions and malodor maskants.
    Type: Grant
    Filed: October 27, 1993
    Date of Patent: June 14, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, Matthew J. McGinnis, Leroy P. John, Franc T. Schiet, Charles E. J. Beck
  • Patent number: 5292720
    Abstract: The present invention relates to novel formate ester indane compounds having fragrant musk-like aroma.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: March 8, 1994
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 5292719
    Abstract: The present invention relates to novel formate ester tetralin compounds having fragrant musk-like aroma.
    Type: Grant
    Filed: June 18, 1993
    Date of Patent: March 8, 1994
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 5278141
    Abstract: The invention concerns novel, non-therapeutic fragrance compositions containing an odorant and a naturally occurring human pheromone. The invention also concerns fragrance compositions containing mixtures of naturally occurring human pheromones. The human pheromones disclosed are steroids which belong to two distinct chemical classes: 16-Androstenes and Estrenes.
    Type: Grant
    Filed: March 8, 1993
    Date of Patent: January 11, 1994
    Assignee: Erox Corporation
    Inventor: David L. Berliner
  • Patent number: 5272134
    Abstract: The invention concerns novel, non-therapeutic fragrance compositions and other compositions containing an odorant and a naturally occurring human pheromone. The invention also concerns fragrance compositions containing mixtures of naturally occurring human pheromones. The human pheromones disclosed are steroids which desirably belong to two distinct chemical classes: 16-Androstenes and Estrenes.
    Type: Grant
    Filed: June 24, 1992
    Date of Patent: December 21, 1993
    Assignee: Erox Corporation
    Inventor: David L. Berliner
  • Patent number: 5206217
    Abstract: The present invention relates to novel indane compounds, such as, for example, 5-formyl-1,1,2,3,3,4,6-heptamethylindane, a compound of the formula ##STR1## and to compositions including the same, as well as to methods for their preparation. Compounds and compositions of the invention possess a fragrant musk-like aroma and have utility in the perfumery and/or other industries.
    Type: Grant
    Filed: December 20, 1991
    Date of Patent: April 27, 1993
    Assignee: Union Camp Corporation
    Inventor: Walter C. Frank
  • Patent number: 5177057
    Abstract: Described is the reaction product of linalool with citric acid wherein the reaction is carried out at 100.degree. C. for a period of about two hours in aqueous media. The resulting reaction product contains alpha terpineol having the structure: ##STR1## The reaction product of our invention may be used to augment, enhance or impart aromas and tastes to consumable materials including perfume compositions, colognes, perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, hair preparations and the like as well as foodstuffs and chewing gums.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: January 5, 1993
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Michael J. Zampino, Braja D. Mookherjee
  • Patent number: 5041422
    Abstract: Described are hydroxy adamantane compounds and derivatives thereof and a process for preparing same.
    Type: Grant
    Filed: December 28, 1990
    Date of Patent: August 20, 1991
    Assignee: Flavors & Fragrances Inc. International
    Inventors: Anubhav Narula, Carlos Benaim