Unsaturation In The Ring Patents (Class 568/377)
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Patent number: 4921873Abstract: This invention relates to antiviral and antitumor compositions, a process for producing the compositions and a method for inhibiting viruses and tumors utilizing the compositions. More particularly, the compositions are cyclohexadienone derivatives which are derived from red alga Desmia hornemanni.Type: GrantFiled: June 14, 1985Date of Patent: May 1, 1990Assignee: Harbor Branch Oceanographic Institution, Inc.Inventors: Tatsuo Higa, Kenneth M. Snader
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Patent number: 4918240Abstract: Beta acids, separated from hop extracts, are purified prior to hydrogenolysis by mixing with an aqueous solution of polyvalent metal ions, preferably edible ions such as magnesium or calcium ions, separating the aqueous beta acids from insoluble materials containing catalyst poisons, and recovering the thus-purified beta acids which are catalyst-poison free and in a form suitable for hydrogenolysis to 4-desoxy alpha acids.Type: GrantFiled: August 15, 1988Date of Patent: April 17, 1990Assignee: Kalamazoo Holdings, Inc.Inventors: Paul H. Todd, Jr., James A. Guzinski
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Patent number: 4914229Abstract: Process for the preparation of the compounds of the formulae Ia and Ib ##STR1## wherein A. 2,4,4-trimethylcyclohex-2-en-1-one oxime of the formula IIb ##STR2## is treated with a strong aqueous acid at from 30.degree. to 80.degree. C., preferably from 40.degree. to 70.degree. C.,B. the resulting ketone of the formula IIIb ##STR3## is oxidized in a conventional manner, and C. if desired, the resulting compound Ib is isomerized in a conventional manner.Compounds of the formula A ##STR4## where R is one of the following radicals: --CH(OH)--CH.sub.2 --CH.dbd.CH.sub.2 (IIIb), --CH(OH)--CH.sub.3 (IIIc), --CH.sub.2 OH (IIId), --CH(OH)--CH.dbd.CH.sub.2 (IIIe), --CH(OCOCH.sub.3)--CH.sub.3 (IIIf), --CH.sub.2 --OCOCH.sub.3 (IIIg), --CO--CH.sub.2 --CH.dbd.CH.sub.2 (Ib), --CO--CH.sub.3 (Ic), and --CO--CH.dbd.CH.sub.2 (Ie).The compounds IIIb to IIIg, Ib, Ic and Ie are useful scents and aromas, and furthermore may become important intermediates for novel carotenoids.Type: GrantFiled: September 9, 1985Date of Patent: April 3, 1990Assignee: BASF AktiengesellschaftInventors: Lothar Janitschke, Werner Hoffmann
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Patent number: 4902716Abstract: This invention relates to antiviral compositions, a process for producing the compositions and a method for inhibiting viruses utilizing the compositions. More particularly, the compositions are halogenated chamigrenes extracted from sea hares which diet upon red algae.Type: GrantFiled: December 18, 1984Date of Patent: February 20, 1990Assignee: Harbor Branch Oceanographic Institutuion, Inc.Inventors: Tatsuo Higa, Kenneth M. Snader
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Patent number: 4871877Abstract: Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts and a proton source. The reaction--which is conducted, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substitutes are a perfluoroalkyl group and a hydroxyl group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.Type: GrantFiled: May 20, 1988Date of Patent: October 3, 1989Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4868339Abstract: Multimethyl cyclohexene or cyclohexane derivatives having woody, spicy, amber or violet odors are disclosed. The derivatives can be formulated into perfurmes, talcs, lotions, cremes and air fresheners.Type: GrantFiled: September 23, 1987Date of Patent: September 19, 1989Assignee: BASF K & F CorporationInventors: Philip A. Christenson, Brian J. Drake
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Patent number: 4847392Abstract: A method of conducting a Diels-Alder reaction is provided comprising reacting a Diels-Alder diene comprising a 1,3-conjugated diene with a dienophile comprising an alpha,beta-unsaturated acetal or ketal in the presence of a protonating acid to yield a [4+2] cycloadduct.Type: GrantFiled: March 17, 1987Date of Patent: July 11, 1989Assignee: Regents of the University of MinnesotaInventors: Paul G. Gassman, Daniel A. Singleton
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Patent number: 4838932Abstract: A method of controlling undesirable vegetation utilizing an herbicidal compounds of the formula ##STR1## wherein X NR.sup.9 wherein R.sup.9 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy;R is halogen; C.sub.1 -C.sub.2 alkyl; C.sub.1 -C.sub.2 alkoxy; trifluoromethoxy; difluoromethoxy; nitro; cyano; C.sub.1 -C.sub.2 haloalkyl; R.sup.a SO.sub.n -- wherein n is 0 or 2 and R.sup.a is C.sub.1 -C.sub.2 alkyl, trifluoromethyl or difluoromethyl;R.sup.1 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl;R.sup.2 is hydrogen or C.sub.1 -C.sub.4 alkyl; orR.sup.1 and R.sup.2 together are C.sub.2 -C.sub.5 alkylene;R.sup.3 is hydrogen, C.sub.1 -C.sub.4 alkyl, phenyl or substituted phenyl, with the proviso that R.sup.1 and R.sup.3 are not both phenyl or substituted phenyl;R.sup.4 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.5 is hydrogen or C.sub.1 -C.sub.4 alkyl;R.sup.6 is hydrogen, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 haloalkyl;R.sup.7 and R.sup.Type: GrantFiled: August 20, 1987Date of Patent: June 13, 1989Assignee: Stauffer Chemical CompanyInventor: Christopher G. Knudsen
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Patent number: 4820331Abstract: Cyclohexenone derivatives of the general formula ##STR1## where R is C.sub.1 -C.sub.6 -alkyl, cyclopropyl, phenyl or C.sub.2 -C.sub.6 -alkoxyalkyl, R.sup.1 is hydrogen, tetrahydropyran-2-yl, benzoyl or unsubstituted or halo-substituted C.sub.1 -C.sub.6 -alkanoyl, and R.sup.2 is hydrogen or C.sub.1 -C.sub.6 -alkyl, and phytophysiologically tolerable salts thereof, and their use for regulating plant growth.Type: GrantFiled: December 3, 1987Date of Patent: April 11, 1989Assignee: BASF AktiengesellschaftInventors: Michael Keil, Ulrich Schirmer, Dieter Kolassa, Juergen Kast, Wilhelm Rademacher, Johann Jung
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Patent number: 4808409Abstract: Racemic hernandulcin, a sesquiterpene, possesses a sweetness intensity about three orders of magnitude greater than that of sucrose. It is non-mutagenic and non-toxic under conventional assay procedures. In addition to attractive utility in foods, beverages and pharmaceutical compositions, it affords a low-cariogenic, essentially non-nutritive sweetening agent for inclusion in oral hygiene products.Type: GrantFiled: August 16, 1984Date of Patent: February 28, 1989Assignee: Board of Trustees, University of IllinoisInventors: Alan D. Kinghorn, Cesar M. Compadre, John M. Pezzuto
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Patent number: 4778691Abstract: A novel method for the removal of hitherto unrecognized undesirable odor-forming impurities from hop flavors, including unreduced alpha and isoalpha acids and reduced alpha and isoalpha acids, by extracting the impurities from these flavors into water at a pH above 4, preferably above 6 or 7, with or without the presence of salt or solvent, and separating the aqueous phase containing the impurities from the purified hop flavor, as well as the important two-phase and salt-containing intermediate products and the final purified hop flavor which is essentially free of such impurities and which purified isoalpha acid or isohumulone will therefore not produce fruity, estery, sour aromas when used to flavor beverages, e.g., beer or ale, are disclosed.Type: GrantFiled: April 3, 1987Date of Patent: October 18, 1988Assignee: Kalamazoo Holdings, Inc.Inventors: Paul H. Todd, Jr., James A. Guzinski
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Patent number: 4760050Abstract: 1-Isopropyl-3-methyl-2-(but-2'-enoyl)cyclohexane derivatives having the general formula ##STR1## in which the dotted lines represent no double bond, one double bond at position 4 or two double bonds at positions 1 and 5, 2 and 4 or 4 and 6 are valuable fragrances with fruity flowery and green odors, in some cases accompanied by woody and/or herbal notes. Above defined compounds can be used as a perfume component in perfume compositions or in products to be perfumed.Type: GrantFiled: January 9, 1987Date of Patent: July 26, 1988Assignee: Naarden Intl. N.V.Inventors: Antonius J. A. Van Der Weerdt, Nicolaas L. J. Broekhof, Jan G. Witteveen
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Patent number: 4744820Abstract: Cyclohexenone derivatives of the formula ##STR1## where R.sup.1 is --CHO or --CH(OR.sup.3).sub.2, R.sup.2 is alkyl or alkoxyalkyl, each of 1 to 4 carbon atoms, or cyclopropyl, and R.sup.3 is alkyl of 1 to 8 carbon atoms, and salts thereof, processes for their manufacture, and their use as agents for regulating plant growth.Type: GrantFiled: February 13, 1987Date of Patent: May 17, 1988Assignee: BASF AktiengesellschaftInventors: Michael Keil, Ulrich Schirmer, Dieter Kolassa, Wilhelm Rademacher, Johann Jung
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Patent number: 4708962Abstract: This invention relates to antitumor compositions, and a method for inhibiting, remitting or controlling the growth of tumors or tumor cells utilizing antitumor compositions. More particularly, the antitumor compositions comprise, as active ingredient, an antitumor effective amount of halogenated chamigrenes extracted and derived from red alga and sea hares which diet upon red alga.Type: GrantFiled: September 4, 1985Date of Patent: November 24, 1987Assignee: Harbor Branch Oceanographic Institution, Inc.Inventors: Tatsuo Higa, Kenneth M. Snader
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Patent number: 4704477Abstract: Compounds of the general formula ##STR1## wherein A is the ##STR2## group and in which R.sup.1 stands for hydrogen, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy and isopropoxy and R.sup.2 and R.sup.3 are hydrogen, methyl and ethyl. The compounds are used as perfume substances.Type: GrantFiled: March 7, 1986Date of Patent: November 3, 1987Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Helmut Gebauer, Hans Mehlin, Marlies Regiert
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Patent number: 4663478Abstract: By reacting a phenol compound with an organic halide selected from the group consisting of a haloform, a carbon tetrahalide and a substituted or unsubstituted allyl halide in the presence of an alkali metal hydroxide, using as a catalyst a fixed cyclodextrin having hydroxyl groups crosslinked with a bivalent hydrocarbon group having free valences at its both ends, said hydrocarbon group having at least one hydrogen atom substituted or unsubstituted with a member selected from the group consisting of an alkyl group, a halogen atom and a hydroxyl group and containing or not containing at least one combination of two neighboring carbon atoms having therebetween at least one member selected from the group consisting of an oxygen atom, a sulfur atom and a phenylene, various useful para-substituted phenol derivatives can be advantageously obtained.Type: GrantFiled: April 18, 1985Date of Patent: May 5, 1987Assignee: Hidefuni HiraiInventors: Hidefuni Hirai, Makoto Komiyama, Izuru Sugiura
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Patent number: 4661641Abstract: Compounds of the formula ##STR1## wherein n is either 0 or 1; R.sup.1 and R.sup.2 is hydrogen and the other is hydrogen, hydroxy, oxo group, a protected hydroxy or protected oxo group; R.sup.3 is hydroxy oxo group, .dbd.CH--CH.sub.2 --OH, .dbd.CH--CHO or one of the foregoing groups where the hydroxy or oxo functions are protected; R.sup.4 is --CO--OR.sup.6, --CO--R.sup.6, --CO--NR.sup.6 R.sup.7, --CO--Cl or --SO.sub.2 --R.sup.6 ; R.sup.6 is saturated or aromatic hydrocarbon; and R.sup.7 is saturated or aromatic hydrocarbon or hydrogen,are converted by cleavage of R.sup.4 OH into corresponding cycloalkenes and protecting groups, if present, are hydrolyzed.The compounds obtained are valuable intermediates in carotenoid syntheses.Type: GrantFiled: May 29, 1984Date of Patent: April 28, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
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Patent number: 4661640Abstract: Novel substituted 5-cycloalkyl-2,2-dimethyl-pentan-3-ones of the formula ##STR1## in which R is optionally substituted cycloalkyl,X is halogen andY is hydrogen or halogen,The new compounds are valuable intermediates for the synthesis of substances having plant growth-regulating and fungicidal properties.Type: GrantFiled: February 24, 1986Date of Patent: April 28, 1987Assignee: Bayer AktiengesellschaftInventors: Heinz Ziemann, Karl-Heinrich Mohrmann
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Patent number: 4659510Abstract: Novel trimethylcyclohexenyl compounds of the 1,3,3-trimethyl-1-cyclohexene type having a 3-hydroxy-3-lower alkylpropionyl group at the 6-position of the cyclohexene are provided. These trimethylcyclohexenyl compounds have a floral note reminiscent of a variety of odors. There are also provided aroma compositions containing these compounds.Type: GrantFiled: November 14, 1984Date of Patent: April 21, 1987Assignee: Kuraray Company, Ltd.Inventors: Takashi Ohnishi, Shigeaki Suzuki, Yoshiji Fujita, Takashi Nishida
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Patent number: 4625066Abstract: Novel substituted acetylene-ketones of the formulaR.sup.2 --C.tbd.C--CO--R.sup.1 (I)in whichR.sup.1 represents optionally substituted cycloalkyl with 4 to 7 carbon atoms or the groupings ##STR1## or represents optionally substituted aryl, if R.sup.2 represents optionally substituted cycloalkenyl or optionally substituted cycloalkylalkyl;R.sup.2 represents alkyl, optionally substituted cycloalkyl, optionally substituted cycloalkenyl, optionally substituted cycloalkylalkyl, optionally substituted aryl or optionally substituted aralkyl;R.sup.3 represents halogen;R.sup.4 represents hydrogen or halogen;R.sup.5 represents alkyl with more than 1 carbon atom, alkenyl, alkinyl or the CHO group or a derivative thereof, or represents methyl, if R.sup.2 represents optionally substituted cycloalkenyl or optionally substituted cycloalkylalkyl;R.sup.6 represents cyano, optionally substituted aryl or the groupings --XR.sup.7 or --CONR.sup.8 R.sup.9 ;R.sup.Type: GrantFiled: November 29, 1984Date of Patent: November 25, 1986Assignee: Bayer AktiengesellschaftInventor: Hans-Ludwig Elbe
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Patent number: 4615830Abstract: Described is an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: August 13, 1985Date of Patent: October 7, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4614747Abstract: This invention relates to novel compounds having pharmaceutical activity and having the general structure ##STR1## wherein the Z, R.sub.1, R.sub.2, R.sub.3, R.sub.4, n and m are defined within.Type: GrantFiled: November 29, 1984Date of Patent: September 30, 1986Assignee: USV Pharmaceutical Corp.Inventors: Bernard Loev, Howard Jones, Wan-kit Chan
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Patent number: 4590296Abstract: Beta-acids are separated from alpha-acids in a hop extract without using organic solvents by bubbling CO.sub.2 through an aqueous hop extract having a pH of about 9.6 to about 13 to lower the pH to about 8.5 to about 9.5 to precipitate the beta-acids and leave the alpha-acids in the extract.Type: GrantFiled: January 25, 1984Date of Patent: May 20, 1986Assignee: Miller Brewing CompanyInventors: John M. Cowles, Henry Goldstein, Etzer Chicoye, Patrick L. Ting
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Patent number: 4576741Abstract: Described in an isomer-directed process for producing asymmetric ketones defined according to the generic structure: ##STR1## wherein one of Z.sub.1 or Z.sub.2 is the moiety: ##STR2## and the other of Z.sub.1 or Z.sub.2 is hydrogen; wherein R.sub.11 and R.sub.21 represent hydrogen or the same or different alkyl or alkenyl with the proviso that R.sub.11 and R.sub.21 are not both hydrogen or wherein R.sub.11 and R.sub.21 taken together:(i) complete a cycloalkyl, cycloalkenyl, bicycloalkyl, mono or polyalkyl cycloalkyl or mono or polyalkyl cycloalkenyl ring, or(ii) represent alkylidene, cycloalkenyl alkylidene, aralkylidene, mono or polyalkyl cycloalkenyl alkylidene or mono or polyalkyl aralkylidene;and wherein R.sub.6, R.sub.7 and R.sub.Type: GrantFiled: November 14, 1984Date of Patent: March 18, 1986Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
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Patent number: 4546110Abstract: Compounds which are .beta.-farnesene derivatives obtainable as a Diels-Adler adduct of .beta.-farnesene and a dienophile or by a modification of such an adduct in a manner as defined herein are of value in pest control, particularly in the control of aphids.Type: GrantFiled: January 20, 1983Date of Patent: October 8, 1985Assignee: National Research Development CorporationInventors: Glenn W. Dawson, David C. Griffiths, John A. Pickett
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Patent number: 4524020Abstract: Described are isopropyl substituted cyclohexenyl methyl ketones defined according to the structure: ##STR1## wherein R.sub.1, R.sub.2, R.sub.11 and R.sub.21 each represents hydrogen or methyl with the provisos that:(a) at least two of R.sub.1, R.sub.21, R.sub.2 and R.sub.11 represent hydrogen;(b) either R.sub.2 is methyl and R.sub.21 is hydrogen or R.sub.21 is methyl and R.sub.2 is hydrogen; and(c) R.sub.1 is methyl only when R.sub.2 is methyl and R.sub.11 is methyl only when R.sub.21 is methyl,as well as uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, hair preparations and perfumed polymers.Type: GrantFiled: August 24, 1984Date of Patent: June 18, 1985Assignee: International Flavors & Fragrances Inc.Inventors: Mark A. Sprecker, Robert P. Belko, Augustinus G. Van Loveren, Marie R. Hanna
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Patent number: 4524032Abstract: A process for direct fluorination of etherified or unetherified hydroxy group-bearing aromatic compounds, which comprises reacting an etherified or unetherified hydroxy group-bearing aromatic compound with fluorine gas to give the corresponding etherified or unetherified hydroxy group and at least one fluorine atom-bearing aromatic compound.Type: GrantFiled: January 14, 1983Date of Patent: June 18, 1985Assignee: Daikin Kogyo Co., Ltd.Inventors: Susumu Misaki, Sadamu Ishii, Masahiro Suefuji
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Patent number: 4523031Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with an organic halide selected from the group consisting of a carbon tetrahalide and a substituted or unsubstituted allyl halide in the presence of an alkali metal hydroxide, a substituent group derived from said organic halide can be introduced to the para-position of the phenol compound with high selectivity, whereby various useful para-substituted phenol derivatives can be advantageously obtained.Type: GrantFiled: September 7, 1983Date of Patent: June 11, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hidefumi Hirai, Makoto Komiyama
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Patent number: 4523037Abstract: By reacting, using as a catalyst a modified or unmodified cyclodextrin, a phenol compound with a haloform in the presence of an alkali metal hydroxide, while maintaining the molar ratio of the cyclodextrin to the haloform at 0.5 to 10, a substituent group derived from the haloform can be introduced to the para-position of the phenol compound with high selectivity, whereby useful para-substituted phenol derivatives can be advantageously obtained.Type: GrantFiled: September 7, 1983Date of Patent: June 11, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hidefumi Hirai, Makoto Komiyama
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Patent number: 4503258Abstract: Compounds of the following structure ##STR1## wherein R.sub.1 is selected from the group consisting of hydrogen and 2-propenyl are disclosed useful as intermediates in organic synthesis.Type: GrantFiled: November 14, 1983Date of Patent: March 5, 1985Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, Mark A. Sprecker
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Patent number: 4481372Abstract: Described is a novel process for preparing allyl alpha and beta ionones defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; and wherein the wavy lines represent the cis or trans juxtaposition of the acyl and cyclohexenyl rings about the carbon-carbon double bond which is alpha to the acyl moiety, and intermediates used in said process defined according to the structure: ##STR2## wherein the wavy lines and dashed lines are defined supra and wherein R.sub.1 represents hydrogen or allyl and Z represents methyl or OR.sub.2 and wherein R.sub.2 represents methyl or ethyl.Type: GrantFiled: September 30, 1982Date of Patent: November 6, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz
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Patent number: 4463184Abstract: A novel process is provided for the preparation of carbofuran and certain intermediate products. 1,2-Cyclohexanedione is alkylated with a beta-methallyl compound and the resulting product subjected to a Claisen rearrangement/aromatization to provide the carbofuran phenol. Reaction of the phenol with methyl isocyanate converts the phenol to the desired carbofuran.Type: GrantFiled: September 30, 1982Date of Patent: July 31, 1984Assignee: Union Carbide CorporationInventor: David A. Hunt
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Patent number: 4457862Abstract: New odoriferous compounds, particularly the compounds having the following formula: ##STR1## wherein R is an aliphatic residue having the formula ##STR2## wherein R.sup.1 is a C.sub.1-4 alkyl, C.sub.1-4 alkylidene or C.sub.2-4 alkenyl, the sum of the carbon atoms being in those residues from 2 to 5, m and n being equal to zero or 1, p being 1, 2 or 3 and the dotted lines representing one or two optional double bonds. The invention also relates to a method for the preparation of new di-ketones I: as well as the use of I as odoriferous compounds in odoriferous compositions, which are characterized by a certain proportion of compounds having the formula I.Type: GrantFiled: November 9, 1982Date of Patent: July 3, 1984Assignee: Givaudan CorporationInventors: Josiane Baudin, Hans U. Gonzenbach
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Patent number: 4449008Abstract: Described is the genus of compounds defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; wherein R.sub.4 represents methyl or ethyl; wherein one of R.sub.1, R.sub.2 and R.sub.3 represents 2-methyl-1-propenyl or 2-methyl-1-propylidenyl; and the other of R.sub.1, R.sub.2 and R.sub.3 represent hydrogen; with the provisos that:(i) when the dashed line at the 3-4 position is a double bond, then R.sub.3 is hydrogen or 2-methyl-1-propenyl;(ii) when the dashed line at the 2-3 position is a double bond, then R.sub.2 is hydrogen or 2-methyl-1-propenyl;(iii) when R.sub.4 is ethyl, then R.sub.2 is methyl and the double bond is at the 2-3 position; and(iv) when R.sub.4 is methyl, then R.sub.2 is hydrogen; 2-methyl-1-propenyl or 2-methyl-1-propylidenyl;with the members of said genus being novel compounds when R.sub.4 is ethyl or when R.sub.Type: GrantFiled: May 5, 1983Date of Patent: May 15, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Philip T. Klemarczyk, Lambert Dekker, Jacob Kiwala
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Patent number: 4449009Abstract: Described is the compound defined according to the structure: ##STR1## and the use thereof in augmenting or enhancing the aroma or taste of perfume compositions, perfumed articles, colognes, smoking tobacco or smoking tobacco articles.Type: GrantFiled: April 7, 1983Date of Patent: May 15, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard J. Tokarzewski, William L. Schreiber
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Patent number: 4429164Abstract: Cyclohexadiene derivatives represented by the formula (I) ##STR1## (wherein --X-- represents ##STR2## --Y-- represents ##STR3## and R.sup.1 and R.sup.2 represent a lower alkyl group) and a process for preparing the same.Type: GrantFiled: June 22, 1982Date of Patent: January 31, 1984Assignee: Otsuka Kagaku Yakuhin Kabushini KaishaInventors: Shigeru Torii, Hideo Tanaka, Mitsuo Akada, Tsunehiko Masatomi, Yasuo Shimizu
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Patent number: 4414418Abstract: Process for the production of dimedone from isophorone. The isophorone is converted in the presence of a solvent with ozone into an ozone-addition product. An alcohol corresponding to the ester radical is added at the latest after the formation of the ozone-addition product for the formation of the intermediate product, 3,3-dimethyl-5-oxo-hexanoic acid ester. The ozone addition product is heated in the presence of acids to a temperature of 20.degree. to 150.degree. C. The 3,3-dimethyl-5-oxo-hexanoic acid ester is isolated thereby. The ester is then converted in a further step into dimedone by treatment of the ester with an alkali alcoholate in an anhydrous milieu.Type: GrantFiled: May 19, 1982Date of Patent: November 8, 1983Assignee: Lonza Ltd.Inventor: Pavel Lehky
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Patent number: 4400311Abstract: Described is the genus of compounds defined according to the structure: ##STR1## wherein one of the dashed lines represents a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond; wherein R.sub.4 represents methyl or ethyl; wherein one of the R.sub.1, R.sub.2 and R.sub.3 represents 2-methyl-1-propenyl or 2-methyl-1-propylidenyl; and the other of R.sub.1, R.sub.2 and R.sub.3 represent hydrogen; with the provisos that:(i) when the dashed line at the 3-4 position is a double bond, then R.sub.3 is hydrogen or 2-methyl-1-propenyl;(ii) when the dashed line at the 2-3 position is a double bond, then R.sub.2 is hydrogen or 2-methyl-1-propenyl;(iii) when R.sub.4 is ethyl, then R.sub.2 is methyl and the double bond is at the 2-3 position; and(iv) when R.sub.4 is methyl, then R.sub.2 is hydrogen; 2-methyl-1-propenyl or 2-methyl-1-propylidenyl;with the members of said genus being novel compounds when R.sub.4 is ethyl or when R.sub.Type: GrantFiled: January 28, 1982Date of Patent: August 23, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Philip T. Klemarczyk, Lambert Dekker, Jacob Kiwala
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Patent number: 4400545Abstract: Alicyclic ketone and alcohol derivatives having the structure: ##STR1## wherein the dotted line represents a carbon-carbon double bond or a carbon-carbon single bond; wherein Z is ##STR2## and wherein each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 is hydrogen or lower alkyl are useful as odor-modifying ingredients in perfumes and perfumed products and as flavor-modifying ingredients in foodstuffs and tobacco products.Type: GrantFiled: November 30, 1981Date of Patent: August 23, 1983Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman, John M. Yurecko, Jr.
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Patent number: 4392993Abstract: New alicyclic unsaturated compounds useful as perfume ingredients and perfume compositions containing same. The new compounds have formula ##STR1## possessing a methyl group attached to the carbon atom at position 3 or 4 of the ring and one double bond in one of the positions of the carbonyl side chain as indicated by the dotted line.Type: GrantFiled: July 23, 1981Date of Patent: July 12, 1983Assignee: Firmenich, SAInventors: Alan F. Thomas, Ferdinand Naf
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Patent number: 4369328Abstract: New oxygenated alicyclic compounds of formula ##STR1## (X=OH, alkyl, O-alkyl) are useful as starting materials for the preparation of cyclohexadienic derivatives of formula ##STR2## (X=OH, alkyl, O-alkyl). They are converted into compounds (III) by treating them with an acidic dehydrating agent in the presence of an inert organic solvent.Compounds (I) are manufactured by reacting compounds (II) ##STR3## (X=OH, alkyl, O-alkyl) with an organic peracid.Type: GrantFiled: July 24, 1981Date of Patent: January 18, 1983Assignee: Firmenich SAInventors: Karl-Heinrich Schulte-Elte, Bernard Egger, Bernard Muller
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Patent number: 4341908Abstract: Compounds useful as fragrance materials having the structure ##STR1## wherein each of R.sub.1, R.sub.2, and R.sub.3 are hydrogen or methyl can be prepared by reacting a halogen-containing cyclohexane, having the structure ##STR2## wherein each of R.sub.1, R.sub.2, and R.sub.3 are hydrogen or methyl and X is a halogen, with a reagent capable of effecting intramolecular cyclization.Type: GrantFiled: June 20, 1980Date of Patent: July 27, 1982Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Philip A. Christenson, Robert A. Mack
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Patent number: 4340753Abstract: A method is provided for oxidatively cleaving .alpha.,.beta.-unsaturated cyclic ketones, such as isophorone, with an oxidizing agent, for example, ozone, and thereafter recovering the resulting keto acid. In instances where ozone is used, an aqueous hydroperoxide and phase transfer catalyst can be used to recover the keto acid. Dione cyclics, for example, dimedone, can be obtained by direct dehydration of the keto acid.Type: GrantFiled: September 2, 1980Date of Patent: July 20, 1982Assignee: General Electric CompanyInventor: James A. Cella
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Patent number: 4339388Abstract: A synthesis of periplanone-B, a female sex pheromone of the American cockroach, P. americana, is described. Novel compounds which are useful as intermediates in the synthesis of periplanone-B are described including the precursor alcohol, periplanol-B.Type: GrantFiled: April 22, 1980Date of Patent: July 13, 1982Inventor: W. Clark Still
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Patent number: 4335138Abstract: Novel carbamates derived from substituted cyclic .beta.-keto-alcohols, their preparation, and pharmaceutical formulations which contain these compounds and which may be used as hypnotics in the treatment of sleep disturbance and as sedatives.Type: GrantFiled: September 15, 1980Date of Patent: June 15, 1982Assignee: BASF AktiengesellschaftInventors: Walter-Wielant Wiersdorff, Karl-Heinz Geiss, Harald Weifenbach, Wolfgang Worstmann, Dieter Lenke, Rolf Kretzschmar
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Patent number: 4326996Abstract: The present invention relates to substituted cyclohexane derivatives having the structure: ##STR1## wherein the dotted line may be a carbon-carbon double bond or a carbon-carbon single bond; wherein R.sub.1,R.sub.2,R.sub.3, R.sub.4,R.sub.5,R.sub.6,R.sub.7 and R.sub.8 may be hydrogen or lower alkyl; wherein Z may be any of the following: ##STR2## wherein R.sub.9 may be hydrogen or lower alkyl; and wherein R.sub.10 and R.sub.11 are lower alkyl. This invention also provides methods of preparing and using the compounds as odor-modifying ingredients in perfumes and perfumed products, and as flavor-modifying ingredients in foodstuffs and tobacco products.Type: GrantFiled: January 30, 1980Date of Patent: April 27, 1982Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman
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Patent number: 4326997Abstract: Alicyclic ketone and alcohol derivatives having the structure: ##STR1## wherein the dotted line represents a carbon-carbon double bond or a carbon-carbon single bond; wherein Z is ##STR2## and wherein each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 is hydrogen or lower alkyl are useful as odor-modifying ingredients in perfumes and perfumed products and as flavor-modifying ingredients in foodstuffs and tobacco products.Type: GrantFiled: October 8, 1980Date of Patent: April 27, 1982Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Brian J. Willis, Robert G. Eilerman, John M. Yurecko, Jr.
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Patent number: 4324810Abstract: Hop extracts useful in the preparation of anactinic or light stable malt beverages are obtained by a method which does not use organic solvents. The extracts are obtained by first treating a crude hop extract containing humulone with an aqueous reducing solution, heating the resulting mixture to form reduced isohumulone, acidifying the reaction mixture to form an aqueous phase and an organic phase, and then adjusting the temperature to facilitate the separation of the two phases. The organic phase which is obtained contains the desired isomerized and reduced humulone and it can be used per se as an anactinic brew kettle flavoring additive for beer or ale. In a preferred embodiment, the organic phase is further treated with an amount of an aqueous KOH solution sufficient to neutralize the reduced isohumulone and to form both an aqueous phase and a solid phase.Type: GrantFiled: May 29, 1980Date of Patent: April 13, 1982Assignee: Miller Brewing CompanyInventors: Henry Goldstein, Walter Fly, Patrick Ting, Etzer Chicoye
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Patent number: 4313856Abstract: The preparation and use as odorant and/or flavorant of compounds having the formula: ##STR1## wherein R represents a butyl, but-2-en-yl or 1,3-butadienyl group.Type: GrantFiled: October 6, 1980Date of Patent: February 2, 1982Assignee: Givaudan CorporationInventors: Roman Kaiser, Dietmar Lamparsky
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Patent number: 4306097Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.Type: GrantFiled: September 8, 1980Date of Patent: December 15, 1981Assignee: Pfizer Inc.Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.