Unsaturation In The Ring Patents (Class 568/377)
  • Patent number: 4921873
    Abstract: 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: Grant
    Filed: June 14, 1985
    Date of Patent: May 1, 1990
    Assignee: Harbor Branch Oceanographic Institution, Inc.
    Inventors: Tatsuo Higa, Kenneth M. Snader
  • Patent number: 4918240
    Abstract: 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: Grant
    Filed: August 15, 1988
    Date of Patent: April 17, 1990
    Assignee: Kalamazoo Holdings, Inc.
    Inventors: Paul H. Todd, Jr., James A. Guzinski
  • Patent number: 4914229
    Abstract: 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: Grant
    Filed: September 9, 1985
    Date of Patent: April 3, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Janitschke, Werner Hoffmann
  • Patent number: 4902716
    Abstract: 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: Grant
    Filed: December 18, 1984
    Date of Patent: February 20, 1990
    Assignee: Harbor Branch Oceanographic Institutuion, Inc.
    Inventors: Tatsuo Higa, Kenneth M. Snader
  • Patent number: 4871877
    Abstract: 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: Grant
    Filed: May 20, 1988
    Date of Patent: October 3, 1989
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4868339
    Abstract: 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: Grant
    Filed: September 23, 1987
    Date of Patent: September 19, 1989
    Assignee: BASF K & F Corporation
    Inventors: Philip A. Christenson, Brian J. Drake
  • Patent number: 4847392
    Abstract: 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: Grant
    Filed: March 17, 1987
    Date of Patent: July 11, 1989
    Assignee: Regents of the University of Minnesota
    Inventors: Paul G. Gassman, Daniel A. Singleton
  • Patent number: 4838932
    Abstract: 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: Grant
    Filed: August 20, 1987
    Date of Patent: June 13, 1989
    Assignee: Stauffer Chemical Company
    Inventor: Christopher G. Knudsen
  • Patent number: 4820331
    Abstract: 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: Grant
    Filed: December 3, 1987
    Date of Patent: April 11, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Keil, Ulrich Schirmer, Dieter Kolassa, Juergen Kast, Wilhelm Rademacher, Johann Jung
  • Patent number: 4808409
    Abstract: 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: Grant
    Filed: August 16, 1984
    Date of Patent: February 28, 1989
    Assignee: Board of Trustees, University of Illinois
    Inventors: Alan D. Kinghorn, Cesar M. Compadre, John M. Pezzuto
  • Patent number: 4778691
    Abstract: 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: Grant
    Filed: April 3, 1987
    Date of Patent: October 18, 1988
    Assignee: Kalamazoo Holdings, Inc.
    Inventors: Paul H. Todd, Jr., James A. Guzinski
  • Patent number: 4760050
    Abstract: 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: Grant
    Filed: January 9, 1987
    Date of Patent: July 26, 1988
    Assignee: Naarden Intl. N.V.
    Inventors: Antonius J. A. Van Der Weerdt, Nicolaas L. J. Broekhof, Jan G. Witteveen
  • Patent number: 4744820
    Abstract: 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: Grant
    Filed: February 13, 1987
    Date of Patent: May 17, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Keil, Ulrich Schirmer, Dieter Kolassa, Wilhelm Rademacher, Johann Jung
  • Patent number: 4708962
    Abstract: 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: Grant
    Filed: September 4, 1985
    Date of Patent: November 24, 1987
    Assignee: Harbor Branch Oceanographic Institution, Inc.
    Inventors: Tatsuo Higa, Kenneth M. Snader
  • Patent number: 4704477
    Abstract: 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: Grant
    Filed: March 7, 1986
    Date of Patent: November 3, 1987
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Helmut Gebauer, Hans Mehlin, Marlies Regiert
  • Patent number: 4663478
    Abstract: 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: Grant
    Filed: April 18, 1985
    Date of Patent: May 5, 1987
    Assignee: Hidefuni Hirai
    Inventors: Hidefuni Hirai, Makoto Komiyama, Izuru Sugiura
  • Patent number: 4661641
    Abstract: 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: Grant
    Filed: May 29, 1984
    Date of Patent: April 28, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
  • Patent number: 4661640
    Abstract: 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: Grant
    Filed: February 24, 1986
    Date of Patent: April 28, 1987
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Ziemann, Karl-Heinrich Mohrmann
  • Patent number: 4659510
    Abstract: 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: Grant
    Filed: November 14, 1984
    Date of Patent: April 21, 1987
    Assignee: Kuraray Company, Ltd.
    Inventors: Takashi Ohnishi, Shigeaki Suzuki, Yoshiji Fujita, Takashi Nishida
  • Patent number: 4625066
    Abstract: 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: Grant
    Filed: November 29, 1984
    Date of Patent: November 25, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventor: Hans-Ludwig Elbe
  • Patent number: 4615830
    Abstract: 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: Grant
    Filed: August 13, 1985
    Date of Patent: October 7, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
  • Patent number: 4614747
    Abstract: 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: Grant
    Filed: November 29, 1984
    Date of Patent: September 30, 1986
    Assignee: USV Pharmaceutical Corp.
    Inventors: Bernard Loev, Howard Jones, Wan-kit Chan
  • Patent number: 4590296
    Abstract: 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: Grant
    Filed: January 25, 1984
    Date of Patent: May 20, 1986
    Assignee: Miller Brewing Company
    Inventors: John M. Cowles, Henry Goldstein, Etzer Chicoye, Patrick L. Ting
  • Patent number: 4576741
    Abstract: 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: Grant
    Filed: November 14, 1984
    Date of Patent: March 18, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
  • Patent number: 4546110
    Abstract: 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: Grant
    Filed: January 20, 1983
    Date of Patent: October 8, 1985
    Assignee: National Research Development Corporation
    Inventors: Glenn W. Dawson, David C. Griffiths, John A. Pickett
  • Patent number: 4524020
    Abstract: 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: Grant
    Filed: August 24, 1984
    Date of Patent: June 18, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, Augustinus G. Van Loveren, Marie R. Hanna
  • Patent number: 4524032
    Abstract: 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: Grant
    Filed: January 14, 1983
    Date of Patent: June 18, 1985
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Susumu Misaki, Sadamu Ishii, Masahiro Suefuji
  • Patent number: 4523031
    Abstract: 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: Grant
    Filed: September 7, 1983
    Date of Patent: June 11, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hidefumi Hirai, Makoto Komiyama
  • Patent number: 4523037
    Abstract: 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: Grant
    Filed: September 7, 1983
    Date of Patent: June 11, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hidefumi Hirai, Makoto Komiyama
  • Patent number: 4503258
    Abstract: 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: Grant
    Filed: November 14, 1983
    Date of Patent: March 5, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Mark A. Sprecker
  • Patent number: 4481372
    Abstract: 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: Grant
    Filed: September 30, 1982
    Date of Patent: November 6, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz
  • Patent number: 4463184
    Abstract: 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: Grant
    Filed: September 30, 1982
    Date of Patent: July 31, 1984
    Assignee: Union Carbide Corporation
    Inventor: David A. Hunt
  • Patent number: 4457862
    Abstract: 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: Grant
    Filed: November 9, 1982
    Date of Patent: July 3, 1984
    Assignee: Givaudan Corporation
    Inventors: Josiane Baudin, Hans U. Gonzenbach
  • Patent number: 4449008
    Abstract: 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: Grant
    Filed: May 5, 1983
    Date of Patent: May 15, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Philip T. Klemarczyk, Lambert Dekker, Jacob Kiwala
  • Patent number: 4449009
    Abstract: 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: Grant
    Filed: April 7, 1983
    Date of Patent: May 15, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard J. Tokarzewski, William L. Schreiber
  • Patent number: 4429164
    Abstract: 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: Grant
    Filed: June 22, 1982
    Date of Patent: January 31, 1984
    Assignee: Otsuka Kagaku Yakuhin Kabushini Kaisha
    Inventors: Shigeru Torii, Hideo Tanaka, Mitsuo Akada, Tsunehiko Masatomi, Yasuo Shimizu
  • Patent number: 4414418
    Abstract: 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: Grant
    Filed: May 19, 1982
    Date of Patent: November 8, 1983
    Assignee: Lonza Ltd.
    Inventor: Pavel Lehky
  • Patent number: 4400311
    Abstract: 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: Grant
    Filed: January 28, 1982
    Date of Patent: August 23, 1983
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Philip T. Klemarczyk, Lambert Dekker, Jacob Kiwala
  • Patent number: 4400545
    Abstract: 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: Grant
    Filed: November 30, 1981
    Date of Patent: August 23, 1983
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Robert G. Eilerman, John M. Yurecko, Jr.
  • Patent number: 4392993
    Abstract: 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: Grant
    Filed: July 23, 1981
    Date of Patent: July 12, 1983
    Assignee: Firmenich, SA
    Inventors: Alan F. Thomas, Ferdinand Naf
  • Patent number: 4369328
    Abstract: 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: Grant
    Filed: July 24, 1981
    Date of Patent: January 18, 1983
    Assignee: Firmenich SA
    Inventors: Karl-Heinrich Schulte-Elte, Bernard Egger, Bernard Muller
  • Patent number: 4341908
    Abstract: 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: Grant
    Filed: June 20, 1980
    Date of Patent: July 27, 1982
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Philip A. Christenson, Robert A. Mack
  • Patent number: 4340753
    Abstract: 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: Grant
    Filed: September 2, 1980
    Date of Patent: July 20, 1982
    Assignee: General Electric Company
    Inventor: James A. Cella
  • Patent number: 4339388
    Abstract: 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: Grant
    Filed: April 22, 1980
    Date of Patent: July 13, 1982
    Inventor: W. Clark Still
  • Patent number: 4335138
    Abstract: 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: Grant
    Filed: September 15, 1980
    Date of Patent: June 15, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Walter-Wielant Wiersdorff, Karl-Heinz Geiss, Harald Weifenbach, Wolfgang Worstmann, Dieter Lenke, Rolf Kretzschmar
  • Patent number: 4326996
    Abstract: 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: Grant
    Filed: January 30, 1980
    Date of Patent: April 27, 1982
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Robert G. Eilerman
  • Patent number: 4326997
    Abstract: 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: Grant
    Filed: October 8, 1980
    Date of Patent: April 27, 1982
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Brian J. Willis, Robert G. Eilerman, John M. Yurecko, Jr.
  • Patent number: 4324810
    Abstract: 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: Grant
    Filed: May 29, 1980
    Date of Patent: April 13, 1982
    Assignee: Miller Brewing Company
    Inventors: Henry Goldstein, Walter Fly, Patrick Ting, Etzer Chicoye
  • Patent number: 4313856
    Abstract: 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: Grant
    Filed: October 6, 1980
    Date of Patent: February 2, 1982
    Assignee: Givaudan Corporation
    Inventors: Roman Kaiser, Dietmar Lamparsky
  • Patent number: 4306097
    Abstract: 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: Grant
    Filed: September 8, 1980
    Date of Patent: December 15, 1981
    Assignee: Pfizer Inc.
    Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.