Abstract: Described is 2-methoxy-4-formyl phenyl ester of propionic acid defined according to the structure: ##STR1## and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.
Type:
Grant
Filed:
December 15, 1994
Date of Patent:
January 23, 1996
Assignee:
International Flavors & Fragrances Inc.
Inventors:
Mark A. Sprecker, Richard A. Weiss, Marie R. Hanna
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
Abstract: Described is a two-step process for producing phenyl- and cyclohexyl-substituted oxybutane derivative-containing mixtures of our invention by means of first reacting methyl ethyl ketone with benzaldehyde in the presence of a sulfonic acid catalyst to produce a mixture of phenyl pentenone derivatives; and then hydrogenating the resulting mixture of phenyl pentenone derivatives in the presence of a hydrogenation catalyst, as well as the product produced thereby; and perfumery uses thereof for augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles.
Type:
Grant
Filed:
April 15, 1994
Date of Patent:
December 13, 1994
Assignee:
International Flavors & Fragrances Inc.
Inventors:
Mark A. Sprecker, Richard A. Weiss, Marie R. Hanna
Abstract: Described is 2-ethoxy-4-formyl phenyl ester of propionic acid of our invention defined according to the structure: ##STR1## and uses thereof in augmenting or enhancing the aroma of perfume compositions, perfumed articles and colognes.
Type:
Grant
Filed:
December 17, 1993
Date of Patent:
October 25, 1994
Assignee:
International Flavors & Fragrances Inc.
Inventors:
Mark A. Sprecker, Richard A. Weiss, Richard M. Boden, Olivier J. Gillotin
Abstract: The reaction product of methyl anthranilate with 3-phenylbutanal is useful as a perfuming ingredient for the preparation of perfuming compositions and perfumed articles, to which it imparts a floral-green odor note of the yellow flower type.
Abstract: Aromatic aldehydes of formula ##STR1## possessing a single or a double bond in the position indicated by the dotted line and wherein symbol X represents a monovalent radical or formula ##STR2## or, when the dotted line represents a single bond, of formula ##STR3## and wherein symbol Z stands for an oxygen atom or for two R.sup.2 O radicals, each of R.sup.1 and R.sup.2 representing an alkyl radical having from 1 to 3 carbon atoms.Aromatic aldehydes (I) possess useful odorous properties and can be used as perfuming ingredients for the preparation of perfume bases and perfumed articles. They can also be used as starting materials for the preparation of useful end-products having herbicide and fungicide properties.Process for the preparation of aromatic aldehydes (I) starting from 8-methoxycuminic aldehyde.
Type:
Grant
Filed:
March 18, 1991
Date of Patent:
February 4, 1992
Assignee:
Firmenich SA
Inventors:
Ferdinand Naef, Francois Delay, Arnoldus Uijttewaal
Abstract: Aromatic aldehydes of formula ##STR1## possessing a single or a double bond in the position indicated by the dotted line and wherein symbol X represents a monovalent radical or formula ##STR2## or, when the dotted line represents a single bond, of formula ##STR3## and wherein symbol Z stands for an oxygen atom or for two R.sup.2 O radicals, each of R.sup.1 and R.sup.2 representing an alkyl radical having from 1 to 3 carbon atoms.Aromatic aldehydes (I) posses useful odorous properties and can be used as perfuming ingredients for the preparation of perfume bases and perfumed articles. They can also be used as starting materials for the preparation of useful end-products having herbicide and fungicide properties.Process for the preparation of aromatic aldehydes (I) starting from 8-methoxycuminic aldehyde.
Type:
Grant
Filed:
April 2, 1990
Date of Patent:
November 26, 1991
Assignee:
Firmenich SA
Inventors:
Ferdinand Naef, Francois Delay, Arnoldus Uijttewaal
Abstract: The invention relates to phenylethyl o-methylcinnamate and a process for its preparation. Phenylethyl o-methylcinnamate is prepared by, first, alkylating ethyl acetoacetate with o-methylbenzyl chloride in the presence of a phase transfer catalyst to yield 2-(o-methylbenzyl)-acetoacetate. Thereafter the 2-(o-methylbenzyl)-acetoacetate yielded in the alkylating step is halogenated to yield ethyl 2-halo-2-(o-methylbenzyl)-acetoacetate. This is followed by degarding the ethyl 2-halo-2-(o-methylbenzyl)-acetoacetate acid. Finally the o-methylcinnamic acid obtained in the degarding step is esterified with 2-phenylethanol into phenylethyl o-methylcinnamate. A fragrance composition utilizing phenylethyl o-methylcinnamate is also disclosed.
Abstract: 2-Cyclohexylpropanal derivatives are disclosed. The derivatives are represented by the following formula (I): ##STR1## wherein P is a hydrogen atom and Q represents a group --CH.dbd.N--OH or a group --CH(OR).sub.2, wherein each R represents a lower alkyl group or two R's together form a lower alkylene group which may have a lower alkyl substituent, or P and Q together form a group ##STR2## wherein R' is a lower alkyl group. The compounds possess floral, fruity, or green odors and are useful for preparing perfume compositions.
Type:
Grant
Filed:
August 29, 1989
Date of Patent:
December 18, 1990
Assignee:
Kao Corporation
Inventors:
Junji Koshino, Yoshiaki Fujikura, Manabu Fujita, Nao Toi
Abstract: Novel odorant and/or flavoring substances are described. These are the compounds of the formula ##STR1## wherein: R.sup.1 represents methyl or ethyl,R.sup.2 represents hydrogen or methyl,the dotted line represents an optional carbon-carbon bond,n is 0 or 1, and,when n is O, R.sup.3 is hydrogen and R.sup.4 represents acetyl or propronyl, and,when n is 1, R.sup.3 represents methyl or ethyl and R.sup.4 represents hydrogen or methyl,with the exception of 1,4,4,7a-tetramethyl-3a,4,5,7a-tetrahydro-7(6H)-ind-1-enone.The compounds of formula I possess organoleptic properties which make them particularly suitable for use as odorant and/or flavoring substances.
Abstract: Described are schiff base reaction products of alkyl anthranilates having the structure: ##STR1## wherein R.sub.3 represents methyl or ethyl and aldehydes of the generic structure: ##STR2## wherein R represents unsaturated hydrocarbyl and alkoxy hydrocarbyl moieties or mixtures of aldehydes having the structures: ##STR3## wherein R.sub.1 and R.sub.2 are different alkoxy hydrocarbyl moieties and hydrocarbyl moieties including the aldehydes:(a) bergamal having the structure: ##STR4## (b) floralozone having the structure: ##STR5## (c) pino acetaldehyde having the structure: ##STR6## (d) pino isobutyraldehyde having the structure: ##STR7## (e) melonal having the structure: ##STR8## and (f) canthoxal having the structure: ##STR9## and organoleptic uses thereof in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, colognes, perfumed articles, foodstuffs, chewing gums and beverages.
Type:
Grant
Filed:
June 3, 1988
Date of Patent:
April 25, 1989
Assignee:
International Flavors & Fragrances Inc.
Inventors:
Braja D. Mookherjee, Robert W. Trenkle, Nicholas Calderone, Keith P. Sands, Myrna L. Hagedorn
Abstract: Described are the schiff base reaction products of alkyl anthranilates having the structure: ##STR1## wherein R" represents ethyl or methyl with ketones and aldehydes defined according to the structure: ##STR2## wherein R' represents methyl or hydrogen and R represents one of the moieties: ##STR3## including compounds defined according to the generic structure: ##STR4## wherein R, R' and R" are defined, supra. Also described are uses of such schiff base reaction products in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, perfumed articles (including perfumed polymers, detergents and fabric softeners), colognes, foodstuffs, chewing gums, toothpastes, medicinal products and chewing tobaccos. The schiff base reaction products of our invention also have unexpected, unobvious and advantageous utilities for their deodorancy properties in addition to having valuable properties as fragrance materials and as flavor materials.
Type:
Grant
Filed:
March 22, 1988
Date of Patent:
February 21, 1989
Assignee:
International Flavors & Fragrances Inc.
Inventors:
Braja D. Mookherjee, Robert W. Trenkle, Nicholas Calderone, Keith P. Sands
Abstract: Described is the novel compound genus the beta-alkylidene phenethyl alcohol esters and ethers of our invention defined according to the generic structure: ##STR1## wherein R.sub.5 represents hydrogen or methyl; wherein R.sub.6 represents one of the moieties: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represents the same or different hydrogen or methyl; wherein R.sub.7 represents methyl or ethyl; and wherein R.sub.8 represents hydrogen or methyl; useful in augmenting or enhancing the aroma of consumable materials including perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener articles, fabric softener compositions, cosmetic powders and hair preparations.
Type:
Grant
Filed:
December 18, 1987
Date of Patent:
September 20, 1988
Assignee:
International Flavors & Fragrances Inc.
Inventors:
Mark A. Sprecker, Robert P. Belko, Richard M. Boden, Marie R. Hanna
Abstract: Described is a process for preparing natural benzaldehyde and acetaldehyde and compositions of matter containing natural benzaldehyde and acetaldehyde as well as products produced thereby and organoleptic utilities thereof, which process comprises the step of contacting with base naturally occurring cinnamaldehyde or a natural product rich in cinnamaldehyde such as Ceylon oil of cinnamon, Ceylon cinnamon bark, Saigon cinnamon bark, cassia oil, Ceylon cinnamon quills, cinnamon leaf oil, oil of cinnamon Madagascar or the like according to the reaction: ##STR1## the reaction taking place in aqueous media and in the presence of a food grade or natural nonionic emulsifier, preferably a nonionic sorbitan derivative emulsifying agent and in the absence of any other reagents.
Type:
Grant
Filed:
June 29, 1987
Date of Patent:
February 23, 1988
Assignee:
International Flavors & Fragrances Inc.
Inventors:
Alan O. Pittet, Ranya Muralidhara, Arthur L. Liberman
Abstract: This invention relates to compounds of the general structure ##STR1## wherein R and R.sup.1 are lower alkyl having from 1 to 2 carbon atoms useful as fragrance additives and to the fragrance compositions containing the same.
Type:
Grant
Filed:
December 19, 1986
Date of Patent:
December 29, 1987
Assignee:
National Distillers and Chemical Corporation
Abstract: Compounds of the general formula (I) ##STR1## and compounds of the general formula (II) ##STR2## in which R.sup.1 represents --OH, --CH.sub.2 OH, --CH.sub.2 --OCH.sub.3, --CHOH--CH.sub.3, --CHO or --CH(OCH.sub.3).sub.2,R.sup.2 represents methyl or ethyl,R.sup.3 represents hydrogen or methyl, andX represents hydrogen or methyl, are disclosed.Processes for the manufacture of certain compounds of formula (I) and for those of formula (II) are also provided. The compounds are useful as perfume materials.