2,6,6-trialkylcyclohexenyl (e.g., Vitamin A Derivatives, Etc.) Patents (Class 568/447)
  • Patent number: 8779210
    Abstract: Processes for the treatment of an aqueous mixture comprising a dipolar aprotic compound, comprise: a) an adsorption step, in which the aqueous mixture is brought into contact with a porous adsorbent, whereby the porous adsorbent is chosen such that the dipolar aprotic compound adsorbs to it more readily than water; b) a desorption step, in which the porous adsorbent is brought into contact with a desorbing agent, whereby a recovery solution is formed comprising the desorbing agent and the dipolar aprotic compound.
    Type: Grant
    Filed: April 19, 2012
    Date of Patent: July 15, 2014
    Assignee: DSM IP Assets B.V.
    Inventor: Jochen Stangl
  • Publication number: 20130296573
    Abstract: A protected organoboronic acid includes a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. A method of performing a chemical reaction includes contacting a protected organoboronic acid with a reagent, the protected organoboronic acid including a boron having an sp3 hybridization, a conformationally rigid protecting group bonded to the boron, and an organic group bonded to the boron through a boron-carbon bond. The organic group is chemically transformed, and the boron is not chemically transformed.
    Type: Application
    Filed: October 18, 2012
    Publication date: November 7, 2013
    Applicant: The Board of Trustees of the University of Illinois
    Inventors: Martin D. Burke, Eric P. Gillis, Suk Joong Lee, David M. Knapp, Kaitlyn C. Gray
  • Publication number: 20130216492
    Abstract: Provided are a method for searching for a malodor inhibitor by using the response of an olfactory receptor as an indicator; a method for inhibiting malodor based on the antagonism of olfactory receptors; and a malodor inhibitor. Disclosed are a method for searching for a malodor inhibitor, the method including: adding a test substance and a malodor-causing substance to any one olfactory receptor selected from the group consisting of OR51E1, OR2W1, OR10A6, OR51I2, and OR51L1, measuring the response of the olfactory receptor to the malodor-causing substance, identifying the test substance that suppresses the response of the olfactory receptor on the basis of the measured response, and selecting the identified test substance as a malodor inhibitor; an antagonist to any one olfactory receptor selected from the group consisting of OR51E1, OR2W1, OR10A6, OR51I2, and OR51L1; a method for inhibiting malodor using the antagonist.
    Type: Application
    Filed: September 1, 2011
    Publication date: August 22, 2013
    Applicant: KAO CORPORATION
    Inventors: Aya Kato, Naoko Saito, Etsuji Wakisaka
  • Publication number: 20130072559
    Abstract: Compositions of and methods for using synthetic retinal derivatives as retinoid replacements and opsin agonists are provided.
    Type: Application
    Filed: September 14, 2012
    Publication date: March 21, 2013
    Applicant: UNIVERSITY OF WASHINGTON
    Inventors: Krzysztof PALCZEWSKI, Matthew Batten
  • Publication number: 20120209032
    Abstract: Processes for the treatment of an aqueous mixture comprising a dipolar aprotic compound, comprise: a) an adsorption step, in which the aqueous mixture is brought into contact with a porous adsorbent, whereby the porous adsorbent is chosen such that the dipolar aprotic compound adsorbs to it more readily than water; b) a desorption step, in which the porous adsorbent is brought into contact with a desorbing agent, whereby a recovery solution is formed comprising the desorbing agent and the dipolar aprotic compound.
    Type: Application
    Filed: April 19, 2012
    Publication date: August 16, 2012
    Applicant: DSM IP ASSETS B.V.
    Inventor: Jochen STANGL
  • Publication number: 20090287006
    Abstract: The invention relates to a process comprising a condensation step wherein a starting aldehyde or ketone is made to react with an ester of an ?-haloacid to form an epoxy compound, whereby the reaction is carried out in the presence of a dipolar aprotic compound selected from the group consisting of 1-methyl-2-pyrrolidone (NMP), hexamethylphosphorous triamide (HMPT), dimethylsulfoxide (DMSO), and urea derivatives of the following formula: (III) wherein R1, R2, R3 and R4 may each independently be H or a C1-C4 alkyl group and whereby R2 and R3 may together form a heterocyclic group.
    Type: Application
    Filed: September 13, 2006
    Publication date: November 19, 2009
    Inventors: Jochen Stangl, Claude Stritt
  • 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: 7067703
    Abstract: A process for the manufacture of retinal (I) comprises reacting a 5-(2,6,6-trimethyl-cyclohex-1-enyl)-1,4-pentadiene derivative (IIa) or a 5-(2,6,6-trimethyl-cyclohex-2-enyl)-1,4-pentadiene derivative (IIb) or a 5-(2,6,6-trimethyl-2-cyclohexen-1-ylidene)-1-pentene derivative (IIc) or a 5-(2,6,6-trimethyl-cyclohex-1-enyl)-penta-1-en-4-yne derivative (IId) or a 5-(2,6,6-trimethyl-cyclohex-2-enyl)-penta-1-en-4-yne derivative (IIe) with a 1,3-butadiene derivative H2C?C(CH3)CCH?CHOR4 (III) in the presence of a Lewis or Brönsted acid and subjecting the compound obtained in each case [(IVa), (IVb), (IVc), (IVd) or (IVe), respectively] to basic or acidic conditions to eliminate therefrom the moiety R2H and thus produce, according to the immediate precursor, retinal itself or a particular derivative thereof [(I?), (I?), (Va) or (Vb), respectively] and, where in two cases such derivative is produced featuring a triple bond [derivative (Va) or (Vb)], hydrogenating this to produce retinal (I) or the derivative (I?), resp
    Type: Grant
    Filed: October 24, 2002
    Date of Patent: June 27, 2006
    Assignee: DSM IP Assets B.V.
    Inventors: Alexander Radspieler, August Rüttimann
  • Patent number: 6995291
    Abstract: The present invention relates to the field of organic synthesis and more precisely to a process for the synthesis of an unsaturated aldehyde or ketone by oxidation of the corresponding alcohol. The oxidation is performed by a hypochlorite salt and a catalytic amount of a N-(2,2,6,6-tetraalkyl-4-piperidinyl-N-oxyl)-2-amino-1,3,5-triazine compound, preferably a N-oxyl derivative of one of the polymers known under the trademark Chimassorb® 944 or 2020.
    Type: Grant
    Filed: September 22, 2003
    Date of Patent: February 7, 2006
    Assignee: Firmenich SA
    Inventor: Eric Walther
  • Patent number: 6444857
    Abstract: There are disclosed an alcohol derivative of formula (1): wherein Ar is an optionally substituted aryl group and R is a straight or branched C1-C3 lower alkyl group, and the wavy line depicted by indicates a single bond and stereochemistry relating to a double bond bound therewith is E or Z or a mixture thereof, and a process for producing the same and a process for producing Vitamin A aldehyde using the same.
    Type: Grant
    Filed: October 10, 2000
    Date of Patent: September 3, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Shinzo Seko, Naoto Konya, Toshiya Takahashi
  • 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: 6384270
    Abstract: The invention relates to a process for making vitamin A from ethynyl-retro-&agr;-ionol using an allene acetate as intermediate.
    Type: Grant
    Filed: April 20, 2001
    Date of Patent: May 7, 2002
    Assignee: Aventis Animal Nutrition, S.A.
    Inventors: Jean-Erick Ancel, Pierre Meilland
  • 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
  • Patent number: 6211411
    Abstract: There are disclosed sulfone aldehyde derivatives of the Formula (1): wherein Ar is an optionally substituted aryl group, a process for producing retinal by using the same, and an intermediate for producing the sulfone aldehyde derivative.
    Type: Grant
    Filed: June 9, 1999
    Date of Patent: April 3, 2001
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiya Takahashi, Naoto Konya, Shinzo Seko
  • Patent number: 6153769
    Abstract: A process for the manufacture of polyene aldehydes comprises reacting a polyene O,O-ethylene acetal with a 1-alkoxy-1,3-diene in the presence of a Lewis acid or Bronsted acid, hydrolyzing the resulting condensation product and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel polyene O,O-ethylene acetals as well as the likewise novel condensation products in this process form further aspects of the invention. The final products are primarily carotenoids which find corresponding use, e.g. as colorants and pigments for foodstuffs, animal products etc.
    Type: Grant
    Filed: November 17, 1998
    Date of Patent: November 28, 2000
    Assignee: Roche Vitamins Inc.
    Inventor: August Ruttimann
  • Patent number: 6090986
    Abstract: Esters of branched C.sub.9 alcohols suitable as plasticizers are formed by esterification of a C.sub.9 alcohol produced by the aldol condensation from propanal and a C.sub.6 aldehyde and hydrogenation, the propanal optionally having been made from natural gas streams.
    Type: Grant
    Filed: October 27, 1997
    Date of Patent: July 18, 2000
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Allen David Godwin, Richard Henry Schlosberg, Frank Hershkowitz, Michael G. Matturro, Gabor Kiss, Kirk Christian Nadler, Philippe Louis Buess, Richard C. Miller, Paul William Allen, Harry William Deckman, Raf Caers, Edmund John Mozeleski, Robert P Reynolds, Francis Joseph Healy
  • 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: 5929288
    Abstract: To manufacture polyene aldehydes and polyene dialdehydes a polyene O,O-dialkyl acetal or polyene di(O,O-dialkyl acetal) is reacted with a 1-alkoxy-1,3-diene in the presence of a Lewis acid or a Bronsted acid. The reaction mixture is then hydrolyzed and the alcohol is cleaved under basic conditions from the polyene derivative produced by the reacting. Those intermediates in this process from which the alcohol is to be cleaved are novel. The final products are primarily carotenoids which can be used as colorants and pigments for foodstuffs, animal products, and the like.
    Type: Grant
    Filed: May 29, 1997
    Date of Patent: July 27, 1999
    Assignee: Roche Vitamins Inc.
    Inventor: August Ruttimann
  • Patent number: 5925797
    Abstract: The invention relates to the .beta.-methylene aldehydes of formula: ##STR1## in which: R.sub.1 and R.sub.2, which may be identical or different, are chosen from a hydrogen atom and optionally substituted carboacyclic, radicals,R.sub.3 and R.sub.4, which may be identical or different, are chosen from a hydrogen atom and optionally substituted carbocyclic, radicals, it not being possible for R.sub.3 and R.sub.4 simultaneously to be a hydrogen atom.The invention also relates to the use of these compounds for the preparation of compounds of interest, in particular from the retinoid or carotenoid family, and the respective structural analogs thereof.
    Type: Grant
    Filed: May 9, 1996
    Date of Patent: July 20, 1999
    Assignee: Centre National de la Recherche Scientifique (CNRS)
    Inventors: Michel Giraud, Pierre Potier, Zo Andriamialisoa, Alain Valla
  • Patent number: 5639919
    Abstract: The present invention relates to novel intermediates for the preparation of vitamin A and carotenoids, corresponding to the following formula (I): ##STR1## in which X is a carbon atom; n is equal to 1 or 2; R.sub.1, R.sub.2 and R.sub.3, which may be identical or different, each independently represent hydrogen, alkyl containing 1 to 4 carbon atoms, alkenyl containing 2 to 11 carbon atoms or aryl, each alkyl and alkenyl may be linear, branched or cyclic, or R.sub.1 and R.sub.2 can together with the carbon atom to which they are attached form a cycloaliphatic compound which is optionally substituted; and R.sub.4, R.sub.5, R.sub.6, R.sub.7 and R.sub.8, which may be identical or different, each independently represent hydrogen, alkyl containing 1 to 4 carbon atoms or alkenyl containing 2 to 10 carbon atoms, each alkyl or alkenyl being linear, or if containing sufficient numbers of carbon atoms, may also be branched or cyclic, or an aryl containing 6 to 10 carbon atoms, or any two of R.sub.4, R.sub.5, R.sub.6, R.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: June 17, 1997
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventor: Hugues Bienayme
  • Patent number: 5637779
    Abstract: A process for the preparation of vitamin A which comprises condensing ethynyl-.beta.-ionol with the acetal of a C.sub.5 allylic halide in the presence of a catalytic amount of a copper-based catalyst and a base; hydrogenating the condensed compound; eliminating the hydroxyl functional group to obtain retinal; and correcting the retinal obtained.
    Type: Grant
    Filed: February 3, 1995
    Date of Patent: June 10, 1997
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Jean-Erick Ancel, Hugues Bienayme
  • 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: 5250710
    Abstract: The present invention relates to dihydropyran derivatives, processes for preparing, and processes of using the derivatives. The derivatives are prepared by condensation of lithium dienolate of prenal with an aldehyde or a ketone.The pyran derivative prepared from .beta.-ionylideneacetaldehyde when treated in the presence of a catalyst directly forms retinal.
    Type: Grant
    Filed: May 7, 1992
    Date of Patent: October 5, 1993
    Assignee: Rhone-Poulenc Nutrition Animale
    Inventors: Pierre F. Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
  • Patent number: 5206442
    Abstract: The preparation of .alpha.,.beta.-unsaturated aldehydes and ketones IO.dbd.C(R.sup.1)--CR.sup.2 .dbd.CR.sup.3 R.sup.4 Iis carried out by acid hydrolysis of cyclic .alpha.,.beta.-unsaturated acetals II ##STR1## in the presence of saturated aldehydes.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: April 27, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Christiane Mackenroth, Ernst Buschmann
  • Patent number: 5118866
    Abstract: Polyene aldehydes of the general formula I ##STR1## where R is ##STR2## where R' is alkyl, aryl, aralkyl or cycloalkyl and, if desired, may be further substituted, and the radicals R" are each C.sub.1 -C.sub.4 -alkyl or together form --CH.sub.2 --CH.sub.2 -- or --CH.sub.2 --CH.sub.2 --CH.sub.2 -- bridges which, if desired, may be further substituted by C.sub.1 -C.sub.4 -alkyl, are prepared by catalytic oxidation of the corresponding polyene alcohol with oxygen or an oxygen-containing gas by a process wherein the oxidation is carried out in the presence of the catalyst system comprising 2,2,6,6-tetramethylpiperidine 1-oxide or 4-oxo-2,2,6,6-tetramethylpiperidine 1-oxide and copper(I) chloride.
    Type: Grant
    Filed: February 5, 1988
    Date of Patent: June 2, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenter H. Knaus, Joachim Paust
  • Patent number: 5087762
    Abstract: The invention provide a process for producing vitamin A aldehyde in high yield by oxidizing vitamin A with a aldehyde of the general formula (1) ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 are the same or different and respectively represents a lower alkyl group or a lower alkenyl group in the presence of aluminum alkoxide in a catalytic amount.
    Type: Grant
    Filed: November 28, 1990
    Date of Patent: February 11, 1992
    Assignee: Kuraray Company Ltd.
    Inventors: Toshiki Mori, Takashi Onishi, Kazuo Yamamoto
  • Patent number: 5081312
    Abstract: New 4,4,5,8-tetramethyl-1-oxaspiro[2,5]octane. A process for its preparation starting from 2,2,3,6-tetramethyl-1-cyclohexanone is described.4,4,5,8-Tetramethyl-1-oxaspiro[2,5]octane is a useful raw material for the preparation of 2,2,3,6-tetramethyl-cyclohexane-carbaldehyde, a key intermediate for the synthesis of valuable fragrance ingredients.
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: January 14, 1992
    Assignee: Firmenich SA
    Inventors: Christian Chapuis, Christian Margot, Karl-Heinrich Schulte-Elte, Herve Pamingle
  • Patent number: 4983775
    Abstract: Novel physiologically active substances Ks-504a, KS-504b and KS-504d having a vasodilative activity and a novel physiologically active substance KS-504e having an activity to inhibit histamine secretion are produced by culturing a microorganism of the genus Mollisia.
    Type: Grant
    Filed: January 16, 1990
    Date of Patent: January 8, 1991
    Assignee: Kyowa Hakko Kogyo Co., Ltd.
    Inventors: Satoshi Nakanishi, Koji Yamada, Katsuhiko Ando, Isao Kawamoto, Toru Yasuzawa, Hiroshi Sano, Noriaki Hirayama, Hiroshi Kase, Joji Goto, Etsuyo Shimizu
  • Patent number: 4910347
    Abstract: Racemic and optically active cycloaliphatic 2,2,6-trimethylcyclohexanecarboxyaldehyde, also known as dihydrocyclocitral, are prepared by a novel process consisting in the cyclization of enol esters of formula ##STR1## wherein the wavy line defines a C--O bond of cis or trans configuration, X represents an acyl group or P(O)(OR).sub.2, wherein R stands for a lower alkyl monovalent radical or an aryl, and Z represents a monovalent radical of formula ##STR2## by means of an acid cyclization agent.
    Type: Grant
    Filed: October 30, 1988
    Date of Patent: March 20, 1990
    Assignee: Firmenich SA
    Inventor: Dana P. Simmons
  • 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: 4868340
    Abstract: Process for the preparation of cycloaliphatic aldehydes of formula ##STR1## having either an isolated double bond in position 1 or 2 (endocyclic or exocyclic), or two conjugated double bonds in position 1 and 3 or 2(exocyclic) and 3 of the ring as indicated by the dotted lines, which process consists in subjecting to a deprotonation an ester of formula ##STR2## wherein the dotted lines have the above given meaning and Y designates an oxygen atom or a sulphur atom and R' stands for a linear or branched alkyl radical or a substituted or unsubstituted phenyl group, followed by H.sup..crclbar. addition and hydrolysis.
    Type: Grant
    Filed: September 1, 1987
    Date of Patent: September 19, 1989
    Assignee: Firmenich S.A.
    Inventors: Charles Fehr, Jose Galindo
  • Patent number: 4800233
    Abstract: Racemic and optically active cycloaliphatic 2,2,6-trimethyl-cyclohexanecarboxaldehydes, also known as dihydrocyclocitral, are prepared by a novel process consisting in the cyclization of enol esters of formula ##STR1## wherein the wavy line defines a C--O bond of cis or trans configuration, X represents an acyl group or P(O)(OR).sub.2, wherein R stands for a lower alkyl monovalent radical or an aryl, and Z represents a monovalent radical of formula ##STR2## by means of an acid cyclization agent.
    Type: Grant
    Filed: August 3, 1987
    Date of Patent: January 24, 1989
    Assignee: Firmenich S.A.
    Inventor: Dana P. Simmons
  • Patent number: 4764641
    Abstract: A process is described for preparing optically active alpha-halogenated carbonyl compounds.This process consists of transforming the carbonyl compound into the corresponding acetal with tartaric acid or a derivative thereof, halogenating this acetal and releasing the carbonyl compound.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: August 16, 1988
    Assignee: Zambon SpA
    Inventors: Graziano Castaldi, Silvia Cavicchioli, Claudio Giordano, Carlo Restelli
  • Patent number: 4701540
    Abstract: A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.
    Type: Grant
    Filed: March 12, 1984
    Date of Patent: October 20, 1987
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
  • 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: 4506096
    Abstract: 2-Alkyl-2,4-diacyloxy-but-3-enals of the formula ##STR1## where R.sup.1 is alkyl and R.sup.2 is hydrogen, alkyl, a cycloaliphatic radical or an aromatic radical, are prepared by reacting a buta-1,3-diene of the formula ##STR2## with an oxygen donor. The new compounds are valuable intermediates in the preparation of terpenes, e.g. retinal, .beta.-carotin and apocarotinoids.
    Type: Grant
    Filed: March 10, 1983
    Date of Patent: March 19, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Martin Weitz, Rolf Fischer, Joachim Paust
  • Patent number: 4474983
    Abstract: 1,5-Dimethyl-hexa-1,5-dienylene compounds, and especially Vitamin A and derivatives thereof, are made by desuphonylating with a basic reagent a sulphone of the formula: ##STR1## in which the sulphonyl group --SO.sub.2 R replaces a hydrogen atom on carbon atom (a) or (b), R represents a phenyl or napthyl group, A is 2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl, and Q is --CH.sub.2 OH or an ether or ester thereof, CHO, or an acetal group.
    Type: Grant
    Filed: February 4, 1982
    Date of Patent: October 2, 1984
    Assignee: Rhone-Poulenc S.A.
    Inventors: Pierre Chabardes, Marc Julia, Albert Menet
  • 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: 4358614
    Abstract: An improved process for the preparation of cyclocitrals of the general formula I ##STR1## via the novel N-methylaldimines of the general formula II ##STR2## and the novel N-methylaldimines of the formula II. The cyclocitrals of the formula I are obtained in yields of 80-90%, based on citral employed. The compounds I and II are important intermediates for the preparation of fragrances and carotinoids, such as vitamin A, and products related thereto.
    Type: Grant
    Filed: July 2, 1981
    Date of Patent: November 9, 1982
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Janitschke, Werner Hoffmann
  • Patent number: 4331814
    Abstract: Sulphones useful for preparing polyenes have the formula: ##STR1## where the sulphonyl group replaces a hydrogen atom on carbon atom (a) or (b), R represents alkyl, aralkyl or aryl, optionally substituted, A and Q represent an optionally substituted hydrocarbon of 5n+1 carbon atoms (n is 1-5), methyl, optionally substituted by halogen, sulphide or sulphone, CH.sub.2 OH (or an ether or ester thereof), CHO (optionally protected), COOH (or an acid chloride, ester or nitrile thereof), with the proviso that when A represents a 2-(2,6,6-trimethylcyclohex-1-enyl) ethenyl radical, Q cannot represent --COOH or an ester thereof.
    Type: Grant
    Filed: February 1, 1973
    Date of Patent: May 25, 1982
    Assignee: Rhone Poulenc S.A.
    Inventors: Pierre Chabardes, Marc Julia, Albert Menet
  • Patent number: 4315764
    Abstract: 1-Allyl-triazole derivatives of the formula ##STR1## in which R represents hydrogen, alkyl or optionally substituted aralkyl,R.sup.1 represents optionally substituted alkyl, cycloalkyl or optionally substituted aryl,R.sup.2 represents alkyl andR.sup.3 represents alkyl, cycloalkyl, optionally substituted cycloalkenyl, alkenyl or optionally substituted aryl, orR.sup.2 and R.sup.3, together with the carbon atom to which they are bonded, represent optionally substituted cycloalkenyl or cycloalkylX represent the group ##STR2## or the keto group, R.sup.4 represents hydrogen, alkyl, optionally substituted aralkyl, acyl or optionally substituted carbamoyl andR.sup.5 represents hydrogen, alkyl or optionally substituted aralkyl,or acid addition salts or metal salt complexes thereof are characterized by fungicidal and plant growth regulatory activity.
    Type: Grant
    Filed: February 4, 1980
    Date of Patent: February 16, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolf Reiser, Wilfried Draber, Karl H. Buchel, Klaus Lurssen, Paul-Ernst Frohberger, Volker Paul
  • Patent number: 4311860
    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: November 20, 1979
    Date of Patent: January 19, 1982
    Assignee: Givaudan Corporation
    Inventor: Victor Krasnobajew
  • Patent number: 4268444
    Abstract: A process for the preparation of polyene-aldehydes, derived from 2,6-dimethyl-2,4,6,8-nonatetraen-1-al by substitution in the 9-position, by means of the Wittig ylide synthesis. The process is based on the observation, contrary to all expectation, that on reacting 2,6-dimethyl-octa-2,4,6-triene-1,8-dial with an equimolar amount of an ylide, it is exclusively the 8-al group of the dialdehyde which reacts. This specificity of the reaction is of particular importance for the preparation of the food dye .beta.-apo-8'-carotinal.
    Type: Grant
    Filed: November 16, 1979
    Date of Patent: May 19, 1981
    Assignee: BASF Aktiengesellschaft
    Inventor: Hagen Jaedicke
  • Patent number: 4225514
    Abstract: A novel process for the preparation of polyene aldehydes which employs as starting materials, substituted 2H pyrans. Novel substituted 2H pyrans and polyene intermediates are also disclosed.
    Type: Grant
    Filed: June 21, 1978
    Date of Patent: September 30, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Gary L. Olson
  • Patent number: 4209644
    Abstract: An unsaturated carbonyl compound, for example, one expressed by the following formula, ##STR1## is prepared by maintaining at an elevated temperature a novel allyl acetal of a .beta.,.gamma.-unsaturated aldehyde, for example, one expressed by the following formula ##STR2## The allyl acetal can be derived, for example, for 3-methyl-3-butenal-1 having 5 carbon atoms and prenyl alcohol having 5 carbon atoms. Thus, the unsaturated aldehyde having the increased number of carbon atoms can be formed in a high yield by a relatively simple reaction.
    Type: Grant
    Filed: November 30, 1977
    Date of Patent: June 24, 1980
    Assignee: Teijin Limited
    Inventors: Yataro Ichikawa, Teizo Yamaji, Mamoru Yamamoto