2,6,6-trialkylcyclohexenyl (e.g., Vitamin A Derivatives, Etc.) Patents (Class 568/447)
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Patent number: 8779210Abstract: 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: GrantFiled: April 19, 2012Date of Patent: July 15, 2014Assignee: DSM IP Assets B.V.Inventor: Jochen Stangl
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Publication number: 20130296573Abstract: 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: ApplicationFiled: October 18, 2012Publication date: November 7, 2013Applicant: The Board of Trustees of the University of IllinoisInventors: Martin D. Burke, Eric P. Gillis, Suk Joong Lee, David M. Knapp, Kaitlyn C. Gray
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Publication number: 20130216492Abstract: 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: ApplicationFiled: September 1, 2011Publication date: August 22, 2013Applicant: KAO CORPORATIONInventors: Aya Kato, Naoko Saito, Etsuji Wakisaka
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Publication number: 20130072559Abstract: Compositions of and methods for using synthetic retinal derivatives as retinoid replacements and opsin agonists are provided.Type: ApplicationFiled: September 14, 2012Publication date: March 21, 2013Applicant: UNIVERSITY OF WASHINGTONInventors: Krzysztof PALCZEWSKI, Matthew Batten
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Publication number: 20120209032Abstract: 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: ApplicationFiled: April 19, 2012Publication date: August 16, 2012Applicant: DSM IP ASSETS B.V.Inventor: Jochen STANGL
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Publication number: 20090287006Abstract: 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: ApplicationFiled: September 13, 2006Publication date: November 19, 2009Inventors: Jochen Stangl, Claude Stritt
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Patent number: 7071228Abstract: 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: GrantFiled: October 23, 2002Date of Patent: July 4, 2006Inventor: L. Dean Parks
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Patent number: 7067703Abstract: 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?), respType: GrantFiled: October 24, 2002Date of Patent: June 27, 2006Assignee: DSM IP Assets B.V.Inventors: Alexander Radspieler, August Rüttimann
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Patent number: 6995291Abstract: 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: GrantFiled: September 22, 2003Date of Patent: February 7, 2006Assignee: Firmenich SAInventor: Eric Walther
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Patent number: 6444857Abstract: 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: GrantFiled: October 10, 2000Date of Patent: September 3, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Shinzo Seko, Naoto Konya, Toshiya Takahashi
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Patent number: 6388141Abstract: 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: GrantFiled: January 13, 2000Date of Patent: May 14, 2002Assignee: Studiengesellschaft Kohle mbHInventors: Walter Leitner, Daniel Koch
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Patent number: 6384270Abstract: The invention relates to a process for making vitamin A from ethynyl-retro-&agr;-ionol using an allene acetate as intermediate.Type: GrantFiled: April 20, 2001Date of Patent: May 7, 2002Assignee: Aventis Animal Nutrition, S.A.Inventors: Jean-Erick Ancel, Pierre Meilland
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Patent number: 6288283Abstract: 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: GrantFiled: June 1, 2000Date of Patent: September 11, 2001Assignee: Sumitomo Chemical Company, Ltd.Inventors: Shinzo Seko, Naoto Konya, Toshiya Takahashi
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Patent number: 6211411Abstract: 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: GrantFiled: June 9, 1999Date of Patent: April 3, 2001Assignee: Sumitomo Chemical Company, LimitedInventors: Toshiya Takahashi, Naoto Konya, Shinzo Seko
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Patent number: 6153769Abstract: 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: GrantFiled: November 17, 1998Date of Patent: November 28, 2000Assignee: Roche Vitamins Inc.Inventor: August Ruttimann
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Patent number: 6090986Abstract: 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: GrantFiled: October 27, 1997Date of Patent: July 18, 2000Assignee: 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
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Patent number: 6004905Abstract: 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: GrantFiled: September 22, 1998Date of Patent: December 21, 1999Assignee: National Research Council of CanadaInventors: Suzanne R. Abrams, John J. Balsevich, Adrian J. Cutler, Bo Lei, Patricia A. Rose
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Patent number: 5929288Abstract: 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: GrantFiled: May 29, 1997Date of Patent: July 27, 1999Assignee: Roche Vitamins Inc.Inventor: August Ruttimann
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Patent number: 5925797Abstract: 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: GrantFiled: May 9, 1996Date of Patent: July 20, 1999Assignee: Centre National de la Recherche Scientifique (CNRS)Inventors: Michel Giraud, Pierre Potier, Zo Andriamialisoa, Alain Valla
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Patent number: 5639919Abstract: 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: GrantFiled: June 7, 1995Date of Patent: June 17, 1997Assignee: Rhone-Poulenc Nutrition AnimaleInventor: Hugues Bienayme
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Patent number: 5637779Abstract: 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: GrantFiled: February 3, 1995Date of Patent: June 10, 1997Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Jean-Erick Ancel, Hugues Bienayme
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Patent number: 5567852Abstract: 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: GrantFiled: October 7, 1994Date of Patent: October 22, 1996Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Hugues Bienayme, Pierre Meilland
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Patent number: 5518995Abstract: 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: GrantFiled: March 31, 1993Date of Patent: May 21, 1996Assignee: National Research Council of CanadaInventors: Suzanne R. Abrams, Lawrence V. Gusta, Martin J. T. Reaney, Bruce E. Ewan
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Patent number: 5250710Abstract: 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: GrantFiled: May 7, 1992Date of Patent: October 5, 1993Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre F. Chabardes, Lucette Duhamel, Pierre Duhamel, Jerome Guillemont, Jean-Marie Poirier
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Patent number: 5206442Abstract: 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: GrantFiled: February 14, 1992Date of Patent: April 27, 1993Assignee: BASF AktiengesellschaftInventors: Christiane Mackenroth, Ernst Buschmann
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Patent number: 5118866Abstract: 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: GrantFiled: February 5, 1988Date of Patent: June 2, 1992Assignee: BASF AktiengesellschaftInventors: Guenter H. Knaus, Joachim Paust
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Patent number: 5087762Abstract: 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: GrantFiled: November 28, 1990Date of Patent: February 11, 1992Assignee: Kuraray Company Ltd.Inventors: Toshiki Mori, Takashi Onishi, Kazuo Yamamoto
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Patent number: 5081312Abstract: 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: GrantFiled: February 20, 1991Date of Patent: January 14, 1992Assignee: Firmenich SAInventors: Christian Chapuis, Christian Margot, Karl-Heinrich Schulte-Elte, Herve Pamingle
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Patent number: 4983775Abstract: 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: GrantFiled: January 16, 1990Date of Patent: January 8, 1991Assignee: 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
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Patent number: 4910347Abstract: 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: GrantFiled: October 30, 1988Date of Patent: March 20, 1990Assignee: Firmenich SAInventor: Dana P. Simmons
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Patent number: 4868340Abstract: 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: GrantFiled: September 1, 1987Date of Patent: September 19, 1989Assignee: Firmenich S.A.Inventors: Charles Fehr, Jose Galindo
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Patent number: 4868339Abstract: Multimethyl cyclohexene or cyclohexane derivatives having woody, spicy, amber or violet odors are disclosed. The derivatives can be formulated into perfurmes, talcs, lotions, cremes and air fresheners.Type: GrantFiled: September 23, 1987Date of Patent: September 19, 1989Assignee: BASF K & F CorporationInventors: Philip A. Christenson, Brian J. Drake
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Patent number: 4800233Abstract: 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: GrantFiled: August 3, 1987Date of Patent: January 24, 1989Assignee: Firmenich S.A.Inventor: Dana P. Simmons
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Patent number: 4764641Abstract: 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: GrantFiled: October 6, 1986Date of Patent: August 16, 1988Assignee: Zambon SpAInventors: Graziano Castaldi, Silvia Cavicchioli, Claudio Giordano, Carlo Restelli
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Patent number: 4701540Abstract: A process for producing cycloketones of a 5 or 6 carbon chain length through which said ketones are known intermediates for producing carotenoids.Type: GrantFiled: March 12, 1984Date of Patent: October 20, 1987Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Milan Soukup, Erich Widmer
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Patent number: 4594456Abstract: 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: GrantFiled: January 20, 1984Date of Patent: June 10, 1986Assignee: BASF AktiengesellschaftInventors: Ulrich Schaefer-Luederssen, Hagen Jaedicke, Joachim Paust, Manfred Eggersdorfer
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Patent number: 4506096Abstract: 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: GrantFiled: March 10, 1983Date of Patent: March 19, 1985Assignee: BASF AktiengesellschaftInventors: Hans-Martin Weitz, Rolf Fischer, Joachim Paust
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Patent number: 4474983Abstract: 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: GrantFiled: February 4, 1982Date of Patent: October 2, 1984Assignee: Rhone-Poulenc S.A.Inventors: Pierre Chabardes, Marc Julia, Albert Menet
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Patent number: 4390557Abstract: Novel odorant and/or flavorant mixtures are provided by fermentation of ionone type compounds with microorganisms of the genera Botryodiplodia, Botryosphaeria, or Lasiodiplodia.Type: GrantFiled: August 28, 1981Date of Patent: June 28, 1983Assignee: Givaudan CorporationInventor: Victor Krasnobajew
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Patent number: 4390556Abstract: Novel odorant and/or flavorant mixtures are provided by fermentation of ionone type compounds with microorganisms of the genera Botyrodiplodia, Botryosphaeria, or Lasiodiplodia.Type: GrantFiled: August 28, 1981Date of Patent: June 28, 1983Assignee: Givaudan CorporationInventor: Victor Krasnobajew
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Patent number: 4358614Abstract: 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: GrantFiled: July 2, 1981Date of Patent: November 9, 1982Assignee: BASF AktiengesellschaftInventors: Lothar Janitschke, Werner Hoffmann
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Patent number: 4331814Abstract: 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: GrantFiled: February 1, 1973Date of Patent: May 25, 1982Assignee: Rhone Poulenc S.A.Inventors: Pierre Chabardes, Marc Julia, Albert Menet
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Patent number: 4315764Abstract: 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: GrantFiled: February 4, 1980Date of Patent: February 16, 1982Assignee: Bayer AktiengesellschaftInventors: Wolf Reiser, Wilfried Draber, Karl H. Buchel, Klaus Lurssen, Paul-Ernst Frohberger, Volker Paul
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Patent number: 4311860Abstract: Novel odorant and/or flavorant mixtures are provided by fermentation of ionone type compounds with microorganisms of the genera Botryodiplodia, Botryosphaeria, or Lasiodiplodia.Type: GrantFiled: November 20, 1979Date of Patent: January 19, 1982Assignee: Givaudan CorporationInventor: Victor Krasnobajew
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Patent number: 4268444Abstract: 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: GrantFiled: November 16, 1979Date of Patent: May 19, 1981Assignee: BASF AktiengesellschaftInventor: Hagen Jaedicke
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Patent number: 4225514Abstract: 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: GrantFiled: June 21, 1978Date of Patent: September 30, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Gary L. Olson
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Patent number: 4209644Abstract: 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: GrantFiled: November 30, 1977Date of Patent: June 24, 1980Assignee: Teijin LimitedInventors: Yataro Ichikawa, Teizo Yamaji, Mamoru Yamamoto