2,6,6-trialkylcyclohexenyl (e.g., Vitamin A Derivatives, Etc.) Patents (Class 568/378)
  • Patent number: 10519108
    Abstract: Compounds having inhibitory activity against retinaldehyde dehydrogenases (RALDHs). The compounds can be used, for example, to inhibit synthesis of retinoic acid for the treatment of refractive error disorders such as myopia, and as infertility treatments by inhibiting spermatogenesis.
    Type: Grant
    Filed: September 16, 2016
    Date of Patent: December 31, 2019
    Assignees: The Board of Regents of the University of Oklahoma, Oklahoma Medical Research Foundation
    Inventors: Jody A. Summers, Angelica R. Harper, Tim Mather, Anthony Burgett, Anh Thi Quynh Le
  • Publication number: 20130131183
    Abstract: The invention features compositions and methods for the administration of an oxidatively transformed carotenoid, or a fractionated component thereof, for improving the health of animals, such as increasing joint mobility, increasing activity, and improving coat quality.
    Type: Application
    Filed: April 30, 2010
    Publication date: May 23, 2013
    Applicant: Chemaphor Inc.
    Inventors: Janusz Daroszewski, Clayton Paul Dick, Isabella Verzberger-Epshtein
  • Patent number: 8093432
    Abstract: The present disclosure describes processes for the epimerization of a cyclohexene comprising the steps of providing to a reactor a first isomer of a 1-(2-alkyl-3-cyclohexen-1-yl)-alkanone compound according to Formula I wherein R1 ad R2 are each independently C1-C4 alkyl, and R3, R4, R5, R6, R7, and R8 are each independently selected from the group consisting of H and C1-C4 alkyl; and epimerizing the first isomer of the 1-(2-alkyl-3-cyclohexen-1-yl)-alkanone with a metal alkoxide base to form a second isomer of the 1-(2-alkyl-3-cyclohexen-1-yl)-alkanone.
    Type: Grant
    Filed: December 18, 2009
    Date of Patent: January 10, 2012
    Assignee: The Procter & Gamble Company
    Inventors: Daniel Martin Bourgeois, Gregory Scot Miracle, Phillip John Porter, Eva Boros, Kenneth Richard Seddon, Harambage Quintus Nimal Gunaratne
  • Patent number: 8067644
    Abstract: The present disclosure describes processes for producing cyclohexenes using Lewis acidic ionic liquids comprising the steps of providing to a reactor an ?,?-unsaturated carbonyl dienophile, providing to the reactor a 1,3-diene, providing a Lewis acidic ionic liquid to the reactor; and reacting the ?,?-unsaturated carbonyl dienophile with 1,3-diene to form a substituted cyclohexene product. The ?,?-unsaturated carbonyl dienophile can be mesityl oxide, the 1,3-diene can be piperylene; and the Lewis acidic ionic liquid can be AlCl3:[C2mim]Cl; AlCl3:[C8mim]Cl; or mixtures thereof.
    Type: Grant
    Filed: December 18, 2009
    Date of Patent: November 29, 2011
    Assignee: The Procter & Gamble Company
    Inventors: Daniel Martin Bourgeois, Gregory Scot Miracle, Phillip John Porter, Eva Boros, Kenneth Richard Seddon, Harambage Quintus Nimal Gunaratne
  • Patent number: 7947687
    Abstract: This invention comprises antineoplastic curcumin derivatives and methods of preparation and use thereof. Particular reference is made to the following isomeric compounds wherein R1, R2, and R3 are selected from the group consisting of H, OH, OCH3, and COOH.
    Type: Grant
    Filed: October 29, 2007
    Date of Patent: May 24, 2011
    Inventor: Byron C Robinson
  • Publication number: 20100008871
    Abstract: Two sequences of a nucleic acid isolated from a cDNA library of the flowering plant Adonis aestivalis is disclosed (SEQ ID NO: 5). The first DNA sequence, referred to as AdKC28, encodes for a polypeptide (SEQ ID NO: 6) that acts in conjunction with polypeptides encoded by either one of two other closely-related Adonis aestivalis cDNAs, AdKeto1 (SEQ ID NO: 1) and AdKeto2 (SEQ ID NO: 2), to convert ?-carotene (?,?-carotene) into astaxanthin (3,3?-dihydroxy-4,4?-diketo-?, ?-carotene). A second DNA sequence, referred to as AdKCl 7 is also disclosed (FIG. 9). Together, these Adonis aestivalis cDNAs, when operably linked to promoters appropriate to the transgenic host, enable the production of astaxanthin and other carotenoids with 3-hydroxy-4-keto-?-rings in a variety of host cells and organisms.
    Type: Application
    Filed: April 20, 2007
    Publication date: January 14, 2010
    Inventor: Francis X. Cunningham, JR.
  • Patent number: 7399888
    Abstract: The invention relates to novel isoxylitones and their use as anticonvulsant and in the treatment of a variety of disorders.
    Type: Grant
    Filed: July 1, 2006
    Date of Patent: July 15, 2008
    Assignee: HEJ Research Institute Karachi University
    Inventors: Attaur Rahman, Mohammad Iqbal Choudhary, Farzana Shaheen, Arun Ganesan, Shabana Usman Simjee, A. Mohsin Raza
  • Patent number: 7378558
    Abstract: A process for preparing carotenoids, in which the process includes reacting a dialkoxy dialdehyde in a double Wittig condensation with a phosphonium salt of or in a double Wittig-Horner condensation with a phosphonate. The carotenoids include, for example, ?-carotene, zeaxanthin, canthaxanthin, astaxathin, lycopene and croceptin, which are useful as nutraceuticals, food colorants, and feed additives.
    Type: Grant
    Filed: November 17, 2003
    Date of Patent: May 27, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Hansgeorg Ernst, Klaus Henrich, Andreas Keller
  • Patent number: 7253212
    Abstract: The present invention relates to a novel retinol derivative and a cosmetic composition comprising the same, in particular, to a novel retinol derivative represented by the formula (I) exhibiting the effects from both L-ascorbic acid and retinol as well as being free from the disadvantages of two compounds such as skin irritation and instability in cosmetic formulation, and a cosmetic composition comprising the retinol derivative.
    Type: Grant
    Filed: December 18, 2002
    Date of Patent: August 7, 2007
    Assignee: Coreana Cosmetics Co., Ltd.
    Inventors: Kun-Su Lee, Jee-Hean Jeong, Seung-Ji Lee, Jung-No Lee, Byong-Kee Jo
  • Patent number: 7247752
    Abstract: A method used for synthesizing intermediates for use in the synthesis of carotenoids and carotenoid analogs, and/or carotenoid derivatives. In some embodiments, the invention includes methods for synthesizing optically active intermediates useful for the synthesis of optically active carotenoids. Synthesis of optically active carotenoids, in one embodiment, may be accomplished by forming an optically active dihydroxy intermediate from ketoisopherone. The optically active dihydroxy intermediate may be converted into optically active astaxanthin derivatives.
    Type: Grant
    Filed: October 3, 2005
    Date of Patent: July 24, 2007
    Assignee: Cardax Pharmaceuticals, Inc.
    Inventors: Samuel F. Lockwood, Peng Cho Tang, Geoff Nadolski, Henry L. Jackson, Zhiqiang Fang, Yishu Du, Min Yang, William Geiss, Richard Williams, David Burdick
  • Patent number: 7071228
    Abstract: A method of treating said musculoskeletal and connective tissue inflammations including osteoarthritis and associated articular and periarticular inflammations, and non-articular Rheumatism including capsulitis, tendonitis, fibrositis, and perarticular inflammations is disclosed. The method includes administering to a patient of a therapeutically effective amount of a composition comprising 13-cis-retinoic acid. Preferably, the treatment method includes administering to a patient of an initial dosage of a composition comprising 13-cis-retinoic acid for an initial treatment period, and thereafter administering a maintenance dosage of the composition.
    Type: Grant
    Filed: October 23, 2002
    Date of Patent: July 4, 2006
    Inventor: L. Dean Parks
  • Patent number: 6388141
    Abstract: The present invention relates to processes for the preparation of oxo products by the hydroformylation of substrates having C═C double bonds using unmodified rhodium catalysts in a reaction mixture essentially consisting of the substrates, the catalyst and carbon dioxide in a supercritical state (scCO2). In particular, the invention relates to such processes for the preparation of products which contain substantial proportions of branched i-oxo products. Further, the invention relates to such processes for the hydroformylation of substrates which do not correspond to the general formula CnH2n. The invention further relates to such processes in which the separation of product and catalyst is effected using the special solvent properties of scCO2.
    Type: Grant
    Filed: January 13, 2000
    Date of Patent: May 14, 2002
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Walter Leitner, Daniel Koch
  • Patent number: 6344214
    Abstract: Astaxanthin is a potent antioxidant, over 500 times more powerful than Vitamin E and 10 times stronger than other carotenoids such as zeaxanthin, lutein, canthaxanthin and beta-carotene. Astaxanthin has also been shown to enhance and modulate the immune system and diminish the damaging effects of UVA sunlight. Disclosed is a method for retarding and ameliorating fever blisters (cold sores) and canker sores. The method comprises administering a source of astaxanthin in a therapeutically effective amount to prevent, retard and ameliorate fever blisters and canker sores. The astaxanthin may be administered orally, topically, or in a combination of oral and topical dosage.
    Type: Grant
    Filed: December 13, 1999
    Date of Patent: February 5, 2002
    Assignee: Cyanotech Corporation
    Inventor: R. Todd Lorenz
  • Patent number: 6297404
    Abstract: The present invention relates to a process for preparing 3,5,5-trimethylcyclohex-2-ene-1,4-dione (oxoisophorone; OIP) by oxidation of 3,5,5-trimethylcyclohex-3-en-1-one (&bgr;-isophorone, &bgr;-IP) with molecular oxygen in the presence of a solvent, of a base and of a transition metal salen derivative as catalyst and of an additive.
    Type: Grant
    Filed: June 21, 2000
    Date of Patent: October 2, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Jochen Klatt, Thomas Müller, Bernhard Bockstiegel
  • Patent number: 6288283
    Abstract: There are disclosed: a hydroxyaldehyde derivative of formula (1): wherein the wavy line depicted by indicates a single bond and the compound having a double bond to which said single bond is attached represents E or Z isomer or a mixture thereof, a methoxy alcohol derivative of formula (2): wherein the wavy line depicted by indicates a single bond and the compound having a double bond to which said single bond is attached represents E or Z isomer or a mixture thereof, processes for producing the same, and a process for producing a retinal using the same.
    Type: Grant
    Filed: June 1, 2000
    Date of Patent: September 11, 2001
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Shinzo Seko, Naoto Konya, Toshiya Takahashi
  • Publication number: 20010018544
    Abstract: A process for the manufacture of a symmetrical, terminally ring-substituted polyenes by reacting a polyene di(O,O-dialkyl acetal) with a cyclic dienol ether in the presence of a Lewis or Brönsted acid, hydrolyzing the condensation product resulting therefrom and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel cyclic dienol ethers, as well as, novel intermediates resulting from the condensation and additional intermediates in this process form further aspects of the invention. The final products are primarily carotenoids, which find corresponding use, e.g., as colorings and pigments for foodstuffs, animal products, etc.
    Type: Application
    Filed: January 17, 2001
    Publication date: August 30, 2001
    Applicant: ROCHE VITAMINS, INC.
    Inventors: Bruno Burdet, August Ruttimann
  • Patent number: 6265450
    Abstract: An anti-stress composition having for its active ingredient astaxanthin and/or its ester. This composition can be in the form of a pharmaceutical, functional food, food or beverage and so forth.
    Type: Grant
    Filed: October 28, 1996
    Date of Patent: July 24, 2001
    Assignees: Suntory Limited, Itano Refrigerated Food Co., Ltd.
    Inventors: Sumio Asami, Zhi-bo Yang, Eiji Yamashita, Hayao Otoze
  • Patent number: 6228893
    Abstract: Described is a cyclohexenone long-chain alcohol represented by the formula (1): wherein R1, R2 and R3 each independently represents a hydrogen atom or a methyl group and X represents a C10-18 alkylene or alkenylene group. The cyclohexanone long-chain alcohol according to the present invention has excellent neurite growth stimulating effects and is therefore useful as a preventive and/or therapeutic agent for Alzheimer's disease.
    Type: Grant
    Filed: February 14, 2000
    Date of Patent: May 8, 2001
    Assignee: Meiji Milk Products Co., Ltd.
    Inventors: Bang Luu, Gaby Schmitt, Florence Keyling, Celine Junges-Girlanda, Masashi Yamada, Yukie Suma
  • Patent number: 6177400
    Abstract: The compounds according to the general formula in which formula the dotted lines indicate a single or a double bond, n and m are 0 or 1, R1 is hydrogen or an acyl group —C(O)R3, R3 being a linear or branched alkyl or alkylene group from C1 to C8, the oxygen atom being bound to the adjacent &agr;-carbon atom by a double bond in the case where n is 0 and by a single bond in the case where n is 1, R2 is hydrogen or a linear or branched alkyl, alkenyl or alkoxy group from C1 to C8, or R2 is an alkenoxy group which is linked to the group R1 to form a 1,3-dioxolane cycle having 5 to 7 ring members, are useful perfuming ingredients. The most preferred compounds according to the invention are those which have a damascone- or damascenone-like structure, with the methyl substituent being in 4-position of the ring instead of the 2-position, as is the case in damascones and damascenones.
    Type: Grant
    Filed: May 7, 1999
    Date of Patent: January 23, 2001
    Assignee: Firmenich SA
    Inventors: Hubert Mimoun, Wolfgang Klaus Giersch
  • Patent number: 6004905
    Abstract: The invention disclosed relates to a new class of abscisic acid (ABA) analogs of formula I ##STR1## wherein one of R.sub.1 is alkenyl, alkynyl, aryl, cycloalkenyl, other farther substituted carbon chain including deuterium containing residues, and carbon containing substituents with heteroatoms and halogens and the other is methyl, and wherein the five member carbon side chain includes a methyl group at C3, with C5 attached to the ring as shown, including a trans double bond at the C4-C5 position, or a triple bond at this position, and either a cis or a trans double bond at the C2-C3 position, and R.sub.2 is CH.sub.2 OH, CHO, COOH, COO alkyl, or derivatives thereof, and wherein the cyclohexanone ring double bond may also be reduced and to a novel process for synthesizing such ABA analogs.
    Type: Grant
    Filed: September 22, 1998
    Date of Patent: December 21, 1999
    Assignee: National Research Council of Canada
    Inventors: Suzanne R. Abrams, John J. Balsevich, Adrian J. Cutler, Bo Lei, Patricia A. Rose
  • Patent number: 5567852
    Abstract: The present invention relates to novel intermediates for the preparation of vitamin A and carotenoids corresponding to the formula (II): ##STR1## in which A represents a hydrogen or an alkyl, alkenyl or alkoxy group containing 1 to 4 carbon atoms, and X represents a carbon atom, and to a process for their preparation and their use, and further relates to compounds for preparing intermediates of formula (II) corresponding to the formula (III): ##STR2## in which R represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkylcarbonyl, alkenylcarbonyl, alkoxyalkyl or alkoxyalkenyl group in which the alkyl groups have 1 to 10 carbon atoms and the alkenyl groups have 2 to 10 carbon atoms, each of said groups being linear or branched and each being substituted or unsubstituted.
    Type: Grant
    Filed: October 7, 1994
    Date of Patent: October 22, 1996
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Hugues Bienayme, Pierre Meilland
  • Patent number: 5518995
    Abstract: The present invention relates to a composition for enhancing synchrony of germination and emergence in plants and comprises an effective amount of a compound having the following general formula (I); ##STR1##
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: May 21, 1996
    Assignee: National Research Council of Canada
    Inventors: Suzanne R. Abrams, Lawrence V. Gusta, Martin J. T. Reaney, Bruce E. Ewan
  • Patent number: 5449844
    Abstract: The present invention relates to a new method of condensing polyenic compounds wherein a compound having the formula III ##STR1## is condensed with a compound having the formula IV ##STR2## under the influence of a Lewis acid or a protic acid. R.sub.1 through R.sub.7 represent alkyl or alkenyl groups, A' is preferably chlorine, B is preferably a hydroxyl group, and n' is 0 to 10. The invention also relates to novel intermediates for use in the preparation of Vitamins A and E produced by means of the new method.
    Type: Grant
    Filed: November 27, 1992
    Date of Patent: September 12, 1995
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Jean-Erick Ancel, Bienayme, Hugues, Lucette Duhamel, Pierre Duhamel
  • Patent number: 5210314
    Abstract: A process for preparing canthaxanthin (Ia) and astaxanthin (Ib) of the formula I ##STR1##where R is H (a) or OH (b), comprises reacting a tertiary alcohol of the formula II ##STR2##where R is H (a) or OH (b), with trifluoroacetic acid, reacting the resulting novel trifluoroacetate of the formula III ##STR3##with triphenylphosphine, and reacting the resulting novel triphenylphosphonium trifluoroacetate of the formula IV ##STR4##with 2,7-dimethyl-2,4,6-octatriene-1,8-dial under the conditions of a Wittig synthesis. The present invention also relates to the novel trifluoroacetates of the formula III and the corresponding triphenylphosphonium trifluoroacetates of the formula IV.
    Type: Grant
    Filed: April 29, 1991
    Date of Patent: May 11, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Hansgeorg Ernst, Joachim Paust, Werner Hoffmann
  • Patent number: 5118856
    Abstract: A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.
    Type: Grant
    Filed: August 2, 1990
    Date of Patent: June 2, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • Patent number: 5072019
    Abstract: A method for the manufacture of the four geometric isomers of 4-(2-butenyl)idene)-3,5,5-trimethy-2-cyclohexen-1-one is provided. The process comprises pyrolyzing a compound of the formula ##STR1## wherein R represents lower-alkyl-oxycarbonyl, aryl-oxycarbonyl, or, preferably, lower-alkanoyl, benzoyl or substituted benzoyl.
    Type: Grant
    Filed: February 1, 1991
    Date of Patent: December 10, 1991
    Assignee: Givaudan Corporation
    Inventors: Daniel Helmlinger, Frank Kienzle, Erich Widmer
  • Patent number: 5041678
    Abstract: Optically active isomers of alpha-damascone of formula ##STR1## wherein the wavy line designates a C--C bound of cis or trans configuration and its 3-buten-1-one derivative are new compounds having utility in the perfume and flavor industry. They can be prepared starting from an enolate of formula ##STR2## where the wavy line has the meaning given above and Me designates an alkali metal, preferably lithium or magnesium, by treating said enolate with a bifunctional nitrogen derivative of formula ##STR3## where the asterisk identifies a center of chirality;index n stands for zero or 1;each of symbols R.sup.0 and R.sup.1 defines a linear or branched alkyl or aralkyl radical, or one of them represents a hydrogen atom and the other an alkyl radical as defined above;each of symbols R.sup.2 and R.sup.
    Type: Grant
    Filed: September 28, 1990
    Date of Patent: August 20, 1991
    Assignee: Firmenich S.A.
    Inventors: Charles Fehr, Jose Galindo
  • 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: 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: 4731356
    Abstract: 2,3-Epoxy-1-(2,6,6-trimethyl-2-cyclohexen-1-yl)-1-butanone, an epoxy ketone of formula ##STR1## possess useful fragrance characters and, consequently, it can be used advantageously in the manufacture of perfume, perfume bases and perfumed products. It develops a flowery and fruity odor.
    Type: Grant
    Filed: June 4, 1987
    Date of Patent: March 15, 1988
    Assignee: Firmenich SA
    Inventors: Karl-Heinrich Schulte-Elte, Dietrich Kastner
  • 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: 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: 4613706
    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: September 23, 1986
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mark A. Sprecker, Robert P. Belko, William L. Schreiber, Michael Licciardello
  • Patent number: 4594456
    Abstract: 3-Hydroxy-.alpha.-cyclocitral derivatives of the general formula I ##STR1## where R.sup.1 is ##STR2## wherein R.sup.2 and R.sup.3 can be identical or different and are each straight-chain or branched alkyl of 1 to 6 carbon atoms, or R.sup.2 and R.sup.3 together form an ethylene or propylene group which can be substituted by methyl or ethyl, processes for their preparation and their use for the preparation of safranal and 3-hydroxy-.beta.-cyclocitral, as well as optically active - cyclocitral derivatives of the general formulae A and B ##STR3## where R.sup.1 is ##STR4## if X is hydrogen and Y is OH, but is otherwise ##STR5## where R.sup.2 and R.sup.3 have the above meanings, and X and Y together are oxygen, or X is hydrogen if Y is OH, and a process for the preparation of optically active 3-oxo-.alpha.-cyclocitral acetals, wherein a mixture of the corresponding racemic 3-oxo-.alpha.-cyclocitral acetals is separated into the optically active compounds by chromatography over a suitable chiral adsorbent.
    Type: Grant
    Filed: January 20, 1984
    Date of Patent: June 10, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Schaefer-Luederssen, Hagen Jaedicke, Joachim Paust, Manfred Eggersdorfer
  • 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: 4550211
    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 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: March 12, 1984
    Date of Patent: October 29, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Janitschke, Werner Hoffmann
  • Patent number: 4543431
    Abstract: Polyunsaturated ketones of formula ##STR1## having a double bond in position 2' or 3' of the side chain and possessing either an isolated double bond in position 1 or 2, or two conjugated double bonds in positions 1 and 3 of the ring, as indicated by the dotted lines, andwhereinindex n stands for integer 1 or 2, andeach of the symbols R.sup.1 to R.sup.7, identical or different, designates a hydrogen atom or a lower radical,are prepared by a process which makes use of tertiary diallyl carbinols as starting materials.
    Type: Grant
    Filed: February 14, 1984
    Date of Patent: September 24, 1985
    Assignee: Firmenich SA
    Inventors: Karl H. Schulte-elte, Roger L. Snowden, Bernard L. Muller
  • Patent number: 4487944
    Abstract: New acetylenic and allenic carbinols of formula ##STR1## respectively, wherein symbol R stands for a trialkyl-silyl or a C.sub.1 to C.sub.6 alkyl radical, preferably a methyl, a tert-butyl or an isoamyl radical, or a group of formula ##STR2## wherein, when taken separately, each of symbols R.sup.1 and R.sup.2 represents a lower alkyl radical or, when taken together, R.sup.1 and R.sup.2 represent a tetramethylene group, are useful intermediates for the preparation of .beta.-damascenone.
    Type: Grant
    Filed: September 27, 1983
    Date of Patent: December 11, 1984
    Assignee: Firmenich, SA
    Inventors: Karl-Heinrich Schulte-Elte, Bernard M/u/ ller
  • 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: 4479011
    Abstract: Polyunsaturated ketones of formula ##STR1## having a double bond in position 2' or 3' of the side chain and possessing either an isolated double bond in position 1 or 2, or two conjugated double bonds in positions 1 and 3 of the ring, as indicated by the dotted lines, and whereinindex n stands for integer 1 or 2, andeach of the symbols R.sup.1 to R.sup.7, identical or different, designates a hydrogen atom or a lower alkyl radical,are prepared by a process which makes use of tertiary diallyl carbinols as starting materials.
    Type: Grant
    Filed: June 25, 1982
    Date of Patent: October 23, 1984
    Assignee: Firmenich SA
    Inventors: Karl H. Schulte-Elte, Roger L. Snowden, Bernard L. Muller
  • 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: 4458093
    Abstract: Described is the hexadienoyl cyclohexene derivative defined according to the structure: ##STR1## which may either be in the form of a mixture of Z, Z; E, E; Z, E or E, Z isomers or the individual isomers themselves having the structures: ##STR2## a process for preparing same, intermediates useful in said process defined according to the structure: ##STR3## wherein R represents ethyl or methyl and organoleptic uses of the hexadienoyl cyclohexene derivatives in augmenting or enhancing the aroma or taste of consumable materials including perfume compositions, colognes and perfumed articles (e.g. solid or liquid anionic, cationic, nonionic or zwitterionic detergents, hair preparations, fabric softeners, fabric softener articles, cosmetic powders and perfumed polymers); foodstuffs, chewing gums, medicinal products, toothpastes and chewing tobaccos; smoking tobaccos and smoking tobacco articles.
    Type: Grant
    Filed: May 20, 1983
    Date of Patent: July 3, 1984
    Assignee: International Flavors & Fragrances Inc.
    Inventors: John B. Hall, Joseph A. McGhie, Manfred H. Vock
  • Patent number: 4454351
    Abstract: Novel lactonic derivatives and their use as starting materials for preparing macrocyclic hydroxyketones useful as intermediates in the preparation of fragrant compounds.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: June 12, 1984
    Assignee: Firmenich SA
    Inventor: Charles Fehr
  • Patent number: 4405417
    Abstract: A process for the manufacture of the novel compound of the formula ##STR1## from the compound of the formula ##STR2## is described. This process comprises cathodically reducing the compound of formula I in a basic, aqueous-organic solvent mixture.The compound of formula II is an intermediate in the manufacture of rhodoxanthin or zeaxanthin.
    Type: Grant
    Filed: January 17, 1983
    Date of Patent: September 20, 1983
    Assignee: Hoffmann- La Roche Inc.
    Inventors: Hansjorg Grass, Reinhard Zell
  • Patent number: 4390557
    Abstract: Novel odorant and/or flavorant mixtures are provided by fermentation of ionone type compounds with microorganisms of the genera Botryodiplodia, Botryosphaeria, or Lasiodiplodia.
    Type: Grant
    Filed: August 28, 1981
    Date of Patent: June 28, 1983
    Assignee: Givaudan Corporation
    Inventor: Victor Krasnobajew
  • Patent number: 4390556
    Abstract: Novel odorant and/or flavorant mixtures are provided by fermentation of ionone type compounds with microorganisms of the genera Botyrodiplodia, Botryosphaeria, or Lasiodiplodia.
    Type: Grant
    Filed: August 28, 1981
    Date of Patent: June 28, 1983
    Assignee: Givaudan Corporation
    Inventor: Victor Krasnobajew
  • 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: 4352943
    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: March 22, 1978
    Date of Patent: October 5, 1982
    Assignee: Givaudan Corporation
    Inventors: Roman Kaiser, Dietmar Lamparsky
  • 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: 4336401
    Abstract: A novel method of preparing 1-crotonoyl-2,6,6-trimethylcyclohexa-1,3-diene comprises treating an ester of the formula ##STR1## with a proton acid under essentially anhydrous conditions.
    Type: Grant
    Filed: July 17, 1980
    Date of Patent: June 22, 1982
    Assignee: Hercules Incorporated
    Inventor: Lumbertus A. Hulshof