Single Hydroxy Containing (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/825)
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Patent number: 10640477Abstract: This invention relates to a process for the epoxidation of a tetrasubstituted alkene such as terpinolene to the corresponding epoxide such as terpinolene epoxide by reacting the tetrasubstituted alkene with peracetic acid prepared in situ from acetic anhydride and hydrogen peroxide in the presence of at least one buffering agent. Further, the invention relates to the use of an oxidizing agent comprising hydrogen peroxide and acetic anhydride for the in-situ epoxidation of a tetrasubstituted alkene.Type: GrantFiled: June 1, 2017Date of Patent: May 5, 2020Assignee: BASF AGRO B.V.Inventors: Michael Rack, Joachim Gebhardt, Bernd Wolf, Stefan Benson, Roland Goetz, Helmut Kraus
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Patent number: 10538470Abstract: The present invention relates to a process for the preparation of limonene-4-ol by an epoxide ring opening isomerization of terpinolene epoxide.Type: GrantFiled: April 22, 2016Date of Patent: January 21, 2020Assignee: BASF Agro B.V.Inventors: Bernd Wolf, Michael Rack, Stefan Benson, Helmut Kraus, Roland Goetz, Sukunath Narayanan, Chidambaram Rishinaradamangalam
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Patent number: 10344008Abstract: The present invention relates to a process for the preparation of terpinolene epoxide by epoxidation of terpinolene.Type: GrantFiled: April 28, 2016Date of Patent: July 9, 2019Assignee: BASF AGRO B.V.Inventors: Bernd Wolf, Michael Rack, Stefan Benson, Helmut Kraus, Roland Goetz, Sukunath Narayanan, Chidambaram Rishinaradamangalam
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Patent number: 10266468Abstract: The present invention relates to a process for preparing a mixture of terpene alcohols comprising limonene-4-ol and terpinene-4-ol from terpinolene epoxide via an isomerization and/or hydrogenation reaction in the presence of a copper catalyst.Type: GrantFiled: February 16, 2017Date of Patent: April 23, 2019Assignee: BASF Agro B.V.Inventors: Bernd Wolf, Michael Rack, Stefan Benson, Roland Goetz, Helmut Kraus
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Patent number: 10266469Abstract: The present invention relates to a process for preparing terpinene-4-ol from limonene-4-ol via a hydrogenation reaction in the presence of a nickel catalyst.Type: GrantFiled: February 16, 2017Date of Patent: April 23, 2019Assignee: BASF Agro B.V.Inventors: Bernd Wolf, Michael Rack, Stefan Benson, Roland Goetz, Helmut Kraus
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Patent number: 9029613Abstract: Provided is an alicyclic alcohol compound which can be used as a raw material for a compound perfume, and which has excellent floral-green-like aromas which are crisp and fresh; also provided are a manufacturing method for the same, and a perfume composition which contains the alicyclic alcohol compound. An alicyclic alcohol compound having a specified structure represented by chemical formula (1) has excellent floral-green-like aromas which are crisp and fresh; and a method for manufacturing the alicyclic alcohol compound represented by chemical formula (1) by reacting, in the presence of hydrogen fluoride, 4-isopropyl-1-methylcyclohexene and carbon monoxide, isomerizing the resulting 4-isopropyl-1-methylcyclohexane carboxylic acid fluoride, thus making 2-methyl-2-(4-methylcyclohexyl)-propionyl fluoride, reacting with alcohol and acquiring a cyclohexane carbonyl compound, and then reducing the cyclohexane carbonyl compound.Type: GrantFiled: December 27, 2011Date of Patent: May 12, 2015Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Mitsuharu Kitamura, Yoshiharu Ataka, Kazuyuki Fukuda
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Patent number: 9018422Abstract: A method for obtaining silk extract containing lutein according to an embodiment of the invention is described. The lutein extraction method uses a three solvent system for extracting bioactive lutein from silk fibers. The extracted lutein has more than 95% purity in all-E isomer with biological activity being 5 times more effective on lipid peroxidation in retina cells and twice immune stimulation in mice when compared with commercially available lutein.Type: GrantFiled: December 30, 2010Date of Patent: April 28, 2015Inventors: Manote Sutheerawattananonda, Potchanee Kaewkumsan, Nanteetip Limpeanchob, Duangkamol Kanthalert
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Publication number: 20150087855Abstract: Killing of bed bugs is accomplished by bringing the bed bugs into contact with a toxic amount of at least one of the compounds of the structure (I) wherein X is —OH, ?0, or —O(O)CR, wherein R is selected from H and a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 11 carbon atoms; R1 is H or CH3; R2 is H or CH3; R3 is H or a branched or straight chain, saturated or unsaturated hydrocarbyl group with zero to three double bonds and from 1 to 11 carbon atoms; and wherein the compounds of structure (I) contain from 6 to 20 total carbon atoms in the compounds.Type: ApplicationFiled: April 30, 2013Publication date: March 26, 2015Applicant: BEDOUKIAN RESEARCH,INC.Inventor: Robert H. Bedoukian
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Patent number: 8834855Abstract: The invention concerns methods of treating or preventing the effects of irradiation in a human or non-human animal using carotenoid compounds, preferably diadinoxanthin, diatoxanthin and/or fucoxanthin as well as photoprotective compositions and their use to prepare photoprotective or photoprotected products.Type: GrantFiled: January 23, 2006Date of Patent: September 16, 2014Assignee: Promar ASInventors: Geir Johnsen, Per Age Lysaa, Kristin Aamodt
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Publication number: 20140161764Abstract: A composition (useful for attracting Halyomorpha halys) containing (3R,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, and optionally a carrier material or carrier. The composition may also contain (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3R,6S,7R,10R)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10S)-10,11-epoxy-1-bisabolen-3-ol, (3S,6R,7R,10R)-10,11-epoxy-1-bisabolen-3-ol where the composition contains a 3:1 ratio of cis-epoxybisabolenols:trans-epoxybisabolenols produced from (R)-citronellal. These compositions were based on the newly discovered aggregation pheromone components: (3S,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol and (3R,6S,7R,10S)-10,11-epoxy-1-bisabolen-3-ol. The composition may also contain methyl(2E,4E,6Z)-decatrieonate.Type: ApplicationFiled: December 12, 2012Publication date: June 12, 2014Applicant: United States of America as Represented by the Secretary of AgricultureInventor: United States of America as Represented by the Secretary of Agriculture
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Publication number: 20140017178Abstract: The present disclosure embrace Blue Curls (Trichostema lanatum) var. Pirzada and compositions and methods there from. Specifically, the applications provides methods and compositions relating to Blue Curls Pirzada essential oil and floral water.Type: ApplicationFiled: December 21, 2011Publication date: January 16, 2014Inventor: Syed Zebe Pirzada
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Publication number: 20130331615Abstract: A method for obtaining silk extract containing lutein according to an embodiment of the invention is described. The lutein extraction method uses a three solvent system for extracting bioactive lutein from silk fibers. The extracted lutein has more than 95% purity in all-E isomer with biological activity being 5 times more effective on lipid peroxidation in retina cells and twice immune stimulation in mice when compared with commercially available lutein.Type: ApplicationFiled: December 30, 2010Publication date: December 12, 2013Inventors: Manote Sutheerawattananonda, Potchanee Kaewkumsan, Nanteetip Limpeanchob, Duangkamol Kanthalert
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Publication number: 20130158127Abstract: Some embodiments comprise tea tree oil derivatives, and compositions and uses of same, which have decreased cytotoxic and irritating characteristics.Type: ApplicationFiled: December 14, 2012Publication date: June 20, 2013Inventor: Jean-Christophe Sergere
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Publication number: 20130035278Abstract: The present invention relates to a process for the production of formyl cyclohexene derivatives which are suitable as odorants as such or as intermediates for the preparation of further odorants.Type: ApplicationFiled: October 8, 2012Publication date: February 7, 2013Applicant: GIVAUDAN SAInventor: Givaudan SA
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Patent number: 8097762Abstract: The present invention relates to a process for converting lutein and/or lutein esters to (3R)-?-cryptoxanthin and (3R,6?R)-?-cryptoxanthin, suitable for human consumption as dietary supplements, by employing safe and environmentally friendly reagents. (3R)-?-Cryptoxanthin and (3R,6?R)-?-cryptoxanthin are two rare food carotenoids that are not commercially available and the former exhibits vitamin A activity. In the first synthetic step, commercially available lutein and/or lutein esters are transformed into a mixture of dehydration products of lutein (anhydroluteins) in the presence of a catalytic amount of an acid. The resulting anhydroluteins are then converted to (3R)-?-cryptoxanthin (major product) and (3R,6?R)-?-cryptoxanthin (minor product) by heterogeneous catalytic hydrogenation employing transition elements of group VIII (Pt, Pd, Rh supported on alumina or carbon) in a variety of organic solvents under atmospheric pressure of hydrogen and at temperatures ranging from ?15° C. to 40° C.Type: GrantFiled: July 12, 2010Date of Patent: January 17, 2012Assignee: University of Maryland, College ParkInventors: Frederick Khachik, Yufa Liu, Holly Showalter
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Publication number: 20110281949Abstract: Use of alkyl phenol and monocyclic monoterpene-derived compounds in the treatment of neuronal damage and in inhibiting activity of TRPC and non-thermo-TRPM channels, and use of bicyclic monoterpene-derived compounds in activating TRPC and non-thermo-TRPM channels.Type: ApplicationFiled: February 3, 2011Publication date: November 17, 2011Inventors: Baruch Minke, Moshe Parnas
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Publication number: 20110065929Abstract: Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.Type: ApplicationFiled: November 18, 2010Publication date: March 17, 2011Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Hideo SHIMIZU, Daisuke IGARASHI, Wataru KURIYAMA, Yukinori YUSA
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Publication number: 20100168440Abstract: Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.Type: ApplicationFiled: February 9, 2010Publication date: July 1, 2010Applicant: Takasago International CorporationInventors: Hideo SHIMIZU, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
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Publication number: 20100137615Abstract: Provide that a useful catalyst for homogeneous hydrogenation, particularly a catalyst for homogeneous asymmetric hydrogenation for hydrogenation, particularly asymmetric hydrogenation, which is obtainable with comparative ease and is excellent in economically and workability, and a process for producing a hydrogenated compound of an unsaturated compound, particularly an optically active compound using said catalyst with a high yield and optical purity.Type: ApplicationFiled: February 9, 2010Publication date: June 3, 2010Applicant: Takasago International CorporationInventors: Hideo SHIMIZU, Daisuke Igarashi, Wataru Kuriyama, Yukinori Yusa
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Patent number: 7642385Abstract: The present invention relates to alcohol compounds having a scent of natural lily of the valley substantially without any woody scent limiting their applications to raw materials of perfume preparations, and a process for producing the alcohol compounds. The alcohol compounds are represented by the following general formula (I): wherein R1 is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; and any one of dotted lines represents a double bond, and the remaining three dotted lines each represent a single bond.Type: GrantFiled: June 21, 2007Date of Patent: January 5, 2010Assignee: Kao CorporationInventors: Shinji Kotachi, Shigeyoshi Tanaka, Satoshi Ohno
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Publication number: 20090182177Abstract: The present invention relates to alcohol compounds having a scent of natural lily of the valley substantially without any woody scent limiting their applications to raw materials of perfume preparations, and a process for producing the alcohol compounds. The alcohol compounds are represented by the following general formula (I): wherein R1 is a hydrogen atom or a hydrocarbon group having 1 to 4 carbon atoms; and any one of dotted lines represents a double bond, and the remaining three dotted lines each represent a single bond.Type: ApplicationFiled: June 21, 2007Publication date: July 16, 2009Inventors: Shinji Kotachi, Shigeyoshi Tanaka, Satoshi Ohno
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Publication number: 20090081140Abstract: The invention relates to a compound of the formula (VII) to an odoriferous substance or aroma composition comprising such a compound, and to a perfumed or aromatized product comprising such a compound. The invention furthermore relates to the use of a compound of the formula (VII) as an odoriferous substance and/or for improving fixation of an odoriferous substance or aroma composition. The invention moreover relates to a method for producing a compound of the formula (VII), to a method for producing a precursor of the compound of the formula (VII) and to the precursor itself. It moreover relates to a method for producing, enhancing or modifying a sandalwood odor in a mixture.Type: ApplicationFiled: September 12, 2008Publication date: March 26, 2009Applicant: SYMRISE GmbH & Co. KGInventors: Constanze Brocke, Marcus Eh, Egon Oelkers
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Publication number: 20080260662Abstract: The invention concerns methods of treating or preventing the effects of irradiation in a human or non-human animal using carotenoid compounds, preferably diadinoxanthin, diatoxanthin and/or fucoxanthin as well as photoprotective compositions and their use to prepare photoprotective or photoprotected products.Type: ApplicationFiled: January 23, 2006Publication date: October 23, 2008Inventors: Geir Johnsen, Per Age Lysaa, Kristin Aamodt
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Patent number: 7425657Abstract: The invention provides palladium-catalyzed hydrogenations of bio-oils and certain organic compounds. Experimental results have shown unexpected and superior results for palladium-catalyzed hydrogenations of organic compounds typically found in bio-oils.Type: GrantFiled: June 6, 2007Date of Patent: September 16, 2008Assignee: Battelle Memorial InstituteInventors: Douglas C. Elliott, Jianli Hu, Todd R. Hart, Gary G. Neuenschwander
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Patent number: 7323607Abstract: A process for preparing (+)-p-mentha-2,8-diene-1-ol comprising reacting (+)-limonene oxide with at least one amine in the presence of at least one Lewis acid to form amine adduct intermediates. The amine adduct is then oxidized to form an N-oxide that is pyrolized to form (+)-p-mentha-2,8-diene-1-ol.Type: GrantFiled: April 14, 2004Date of Patent: January 29, 2008Assignee: Mallinckrodt Inc.Inventors: Hong Gu, J. Kendall Killgore, John R. Duchek
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Patent number: 7115786Abstract: The present invention relates to a method of reacting (3R,3?R,6?R)-lutein with a catalytic amount of an acid to obtain a mixture of anhydroluteins, rich in anhydrolutein III, with substantially no Z-isomers being formed. The mixture is converted to (3R)-?-cryptoxanthin (major product) and (3R,6?R)-?-cryptoxanthin (minor product) by reacting the anhydroluteins with borane-amine complexes (e.g. Me3N.BH3) or other hydride donors and an acid in a chlorinated solvent, preferably dichloromethane, at ambient temperature to produce (3R)-?-cryptoxanthin and (3R,6?R)-?-cryptoxanthin.Type: GrantFiled: February 6, 2003Date of Patent: October 3, 2006Assignee: University of Maryland, College ParkInventor: Frederick Khachik
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Patent number: 6894198Abstract: An alkali metal alkoxide or alkaline earth metal alkoxide in granular form.Type: GrantFiled: October 15, 2002Date of Patent: May 17, 2005Assignee: Degussa AGInventors: Andreas Harthun, Christoph Theis, André Noppe, Josef Metz
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Patent number: 6867335Abstract: The present invention relates to process wherein (+)-2-carene epoxide is coupled with a compound X—Y that contains nucleophilic and electrophilic moieties, to produce a compound of formula (5). The reaction mixture consists essentially of a source of (+)-2-carene epoxide, compound X—Y, optionally an inert solvent and optionally a pH buffer. No acid catalyst is used in the process.Type: GrantFiled: May 9, 2002Date of Patent: March 15, 2005Assignee: Johnson Matthey Public Limited CompanyInventors: Michael Casner, Theodore Maurice Resnick, Lee Jonathan Silverberg
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Patent number: 6559118Abstract: Novel compounds having the structure (I) where R1 is a lower alkyl group, R2, R3, R4 and R5 is each independently hydrogen or a lower alkyl group, R6 is hydrogen, a lower alkyl group, an alkylidene group or a lower alkenyl group and R7 is hydrogen or a lower alkyl group, have desirable odor properties, possibly of a blackcurrant, green, buchu, cassis nature, and find use in perfumes and perfumed products.Type: GrantFiled: December 7, 2001Date of Patent: May 6, 2003Assignee: Quest International B.V.Inventor: Kenneth Palmer
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Publication number: 20020173680Abstract: Disclosed are spirocyclic olefin polymers, methods of preparing spirocyclic olefin polymers, photoresist compositions including spirocyclic olefin resin binders and methods of forming relief images using such photoresist compositions.Type: ApplicationFiled: April 20, 2002Publication date: November 21, 2002Applicant: Shipley Company, L.L.C.Inventors: Charles R. Szmanda, George G. Barclay, Peter Trefonas, Wang Yueh
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Patent number: 6348622Abstract: There is provided a compound of the formula[I]: wherein R represents a hydrogen atom or a protective group for a hydroxyl group; and A represents a hydrogen atom, a halogen atom or a group of the formula A1: Q represents Q3: when A represents a halogen atom or a protective group for a hydroyl group, A represents Q4: wherein R1 and R2 represent a hydrogen atom or a protective group for a hydroxyl group; and when A represents a hydrogen atom, Q is Q2:Type: GrantFiled: February 9, 2000Date of Patent: February 19, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Toshiya Takahashi, Shinzo Seko, Takashi Miki
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Patent number: 6310262Abstract: A new process prepares retiferol derivatives of formula I: wherein A is —C ≡C— or —CH═CH—, and R1 and R2 are independently of each other lower alkyl or lower perfluoroalkyl, one version couples ketones of formula 1I with compounds of formula III A second version couples phosphinoxides of formula IV with aldehydes of formula V. Compounds of formula I are useful in the treatment or prevention of hyperproliferative skin diseases and for reversing the conditions associated with photodamage.Type: GrantFiled: October 3, 2000Date of Patent: October 30, 2001Assignee: Basilea Pharmaceutica AGInventor: Hans Hilpert
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Patent number: 6303837Abstract: Using the process according to the invention, it is possible to provide, with few reaction steps, a novel route to &agr;-substituted ring systems, which optionally have further substituents.Type: GrantFiled: August 31, 1999Date of Patent: October 16, 2001Assignee: Bayer AktiengesellschaftInventors: Christoph Gürtler, Manfred Jautelat
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Patent number: 6278031Abstract: The fixed-bed catalyst comprises palladium and selenium or tellurium or a mixture of selenium and tellurium on a silicon dioxide support and has a BET surface area of from 80 to 380 m2/g and a pore volume of from 0.6 to 0.95 cm3/g in the pore diameter range from 3 nm to 300 &mgr;m, with from 80 to 95% of the pore volume being in the pore diameter range from 10 to 100 nm. It is prepared by impregnating a silicon dioxide support with a solution of a palladium compound and a selenium compound or tellurium compound or a mixture of a selenium compound and a tellurium compound, drying it and reducing it in the presence of hydrogen. The catalyst is used, in particular, for isomerizing 3-buten-1-ol compounds.Type: GrantFiled: January 16, 2001Date of Patent: August 21, 2001Assignee: BASF AktiengesellschaftInventors: Franz Josef Bröcker, Werner Aquila, Klemens Flick, Gerd Kaibel, Ernst Langguth
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Patent number: 6245952Abstract: The present invention relates to a process for the preparation of alcohols by reduction of the carbonyl function in substrates belonging to the class of aldehydes, ketones, esters or lactones, which substrates may contain unsaturated functions other than carbonyl. This process includes the steps of reacting the carbonyl substrate with stoichiometric amounts of a silane in the presence of catalytic amounts of an active zinc compound which is monomeric and not a hydride, hydrolyzing the thus-obtained siloxane with a basic agent, and separating and purifying, if necessary, the thus-obtained alcohol. The catalytically active compound is generally obtained by the reaction of an oligomeric or polymeric precursor compound of zinc with a complexing agent.Type: GrantFiled: March 1, 1999Date of Patent: June 12, 2001Assignee: Firmenich SAInventor: Hubert Mimoun
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Patent number: 6184422Abstract: Compounds of formula I wherein X is C═CH2 or CH2; Y and Z are independently of each other hydrogen, fluorine or hydroxy; A is —C≡C—, —CH═CH— or —CH2—CH2—, R1 and R2 are independently of each other alkyl or perfluoroalkyl; and R3 is lower alkyl are useful in the treatment or prevention of hyperproliferative skin diseases, particularly psoriasis, basal cell carcinomas, disorders of keratinization and keratosis; or for reversing the conditions associated with photodamage.Type: GrantFiled: February 18, 1999Date of Patent: February 6, 2001Assignee: Hoffman-La Roche Inc.Inventors: Pierre Barbier, Franz Bauer, Peter Mohr, Marc Muller, Wolfgang Pirson
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Patent number: 6184381Abstract: This document describes a novel and practically excellent process for the preparation of optically active compounds, such as optically active alcohols or amines which are useful for various applications, for example, as synthetic intermediates of pharmaceuticals, liquid crystal materials, and reagents for optical resolution, wherein a hydrogen transfer type asymmetric reduction is carried out in the presence of both a transition metal complex and an optically active nitrogen compound or a transition metal complex having an optically active nitrogen compounds as an asymmetric ligand, and a hydrogen-donating organic or inorganic compound.Type: GrantFiled: September 29, 1998Date of Patent: February 6, 2001Assignees: Japan Science & Technology Corp., NKK Corp., Takeda Chemical Industries, Asahi Kasei Kogyo Kabushiki Kaisha, Takasago Intl. Corp.Inventors: Takao Ikariya, Shohei Hashiguchi, Jun Takehara, Nobuyuki Uematsu, Kazuhiko Matsumura, Ryoji Noyori, Akio Fujii
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Patent number: 6111125Abstract: A process for preparing 4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketones of the general formula I, in particular of the (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone of the formula Ia ##STR1## which is required for preparing the red dye capsorubin which is in demand, starts from 2,2,6-trimethylcyclohexanones of the general formula II ##STR2## where R is hydrogen or a protective group, via the novel intermediates of the general formulae V and VI ##STR3## by diastereoselective epoxidation and reaction of the resulting 7-oxabicyclo[4.1.0]heptanes of the general formula VIII ##STR4## with Lewis acids and, where appropriate, removal of the protective group. Also claimed are the novel intermediates of the formula V and their (1S) and (1R) isomers and those of the formula VIII as well as their (1R,3S,6S), (1S,3S,6R) and (1R,3R,6S) isomers.Type: GrantFiled: March 3, 1995Date of Patent: August 29, 2000Assignee: BASF AktiengesellschaftInventors: Michael John, Udo Rheude, Joachim Paust, Joachim Meyer
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Patent number: 5973211Abstract: A method of isomerizing lutein to yield a mixture of epimers of zeaxanthin includes the following steps: mixing a lutein-containing extract in a glycol solution to obtain a mixture, treating the mixture with alkali to obtain an alkali-containing mixture, reacting the alkali-containing mixture in the presence of heat for a duration consistent with achieving a desired level of isomerization of lutein to zeaxanthin.Type: GrantFiled: July 18, 1997Date of Patent: October 26, 1999Assignee: Prodemex, S.A. DE C.V.Inventor: Gustavo Rodriguez
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Patent number: 5900513Abstract: The present invention provide a method for producing 2-cyclohexene-1-ol which comprises using a catalyst containing an inetermetallic compound of palladium and lead and/or bismuth when cyclohexenyl hydroperoxide is subjected to hydrogenolysis to produce 2-cyclohexene-1-ol.If the catalyst of the present invention is employed, it is possible to obtain the desired 2-cyclohexene-1-ol at a high selectivity with a much simpler reaction system than the prior art and, in addition, to inhibit the hydrogenation of coexisting cyclohexene sufficiently.Type: GrantFiled: February 6, 1998Date of Patent: May 4, 1999Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hiroshi Ishida, Mitsuji Ono, Masazumi Chono
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Patent number: 5814612Abstract: The present invention provides a purified retinoid compound characterized by a molecular mass of about 320 daltons and an atomic composition of C.sub.20 H.sub.32 O.sub.3. The present invention also provides a purified retinoid compound having the structure: ##STR1## wherein the configuration of the C7, C9, and C11 double bond independently is Z or E and the absolute configuration at C13 and C14 is independently R or S; wherein R1 is alkyl, alkyl halide, alcohol, ester, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, acyl halide, amide, nitrile, or amine; R2 and R3 are independently hydroxyl, halide, alkoxy, ester, alkyl, alcohol, ether, aldehyde, ketone, carboxylic acid, carboxylic ester, nitrile, amine, azide, alkyl halide, acid halide, acid azide, or amide; or wherein R2 and R3, or R1 and R2 are replaced by a 13,14-oxirane or a 14,15-oxirane group, respectively.Type: GrantFiled: May 6, 1992Date of Patent: September 29, 1998Assignees: Sloan-Kettering Institute for Cancer Research, The Trustees of Columbia in the City of New YorkInventors: Jochen Buck, Ulrich Hammerling, Fadila Derguini, Koji Nakanishi
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Process for the formation, isolation and purification of comestible xanthophyll crystals from plants
Patent number: 5648564Abstract: A process for forming, isolating and purifying xanthophyll crystals, preferably lutein from marigold flower petals, zeaxanthin from wolfberries or capsanthin and capsorubin from red pepper, is disclosed. A xanthophyll diester-containing plant extract is saponified in a composition of propylene glycol and aqueous alkali to form xanthophyll crystals. Crystallization is achieved without the use of added organic solvents. The crystals are isolated and purified. The substantially pure xanthophyll crystals so obtained are suitable for human consumption and can be used as a nutritional supplement and as an additive in food.Type: GrantFiled: December 21, 1995Date of Patent: July 15, 1997Assignee: Kemin Industries, Inc.Inventors: Rodney L. Ausich, David J. Sanders -
Patent number: 5498805Abstract: The present invention relates to an aqueous based micellar solution in the form of a microemulsion which is an effective all-purpose cleaner and which has a flashpoint in excess of its boiling point which is typically greater than 212 degrees Fahrenheit.Type: GrantFiled: February 27, 1995Date of Patent: March 12, 1996Inventor: A. Richard Koetzle
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Patent number: 5329053Abstract: A novel process is described for the manufacture of a mixture of 6-(2',6',6'-trimethyl-cyclohex-1'-en-1'-yl)-4-methyl-hex-3-en-1-ol and -4-en-1-ol (I) and, respectively, of a mixture of [3a.alpha.,5a.beta.,9a.alpha.,9b.beta.]-dodecahydro-3a,6,6,9a-tetramethyln aphtho[2,1-b]furan and [3a.alpha.,5a.beta.,9a.alpha.,9b.alpha.Type: GrantFiled: August 25, 1993Date of Patent: July 12, 1994Assignee: Givaudan-Roure CorporationInventor: Daniel Helmlinger
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Patent number: 5268356Abstract: The cyclic tertiary alcohols of formula ##STR1## wherein the dotted line indicates the location of a single or double bond, symbols R.sup.1 and R.sup.3 represent each a hydrogen atom or a methyl radical and symbol R.sup.2 stands for a lower alkyl radical, are useful perfuming ingredients for the preparation of perfuming compositions and perfumed articles, to which they impart odor notes of the patchouli type.Type: GrantFiled: November 2, 1992Date of Patent: December 7, 1993Assignee: Firmenich SAInventors: Rene Decorzant, Ferdinand Naef
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Patent number: 5250739Abstract: This invention is a process for catalytically oxidizing cycloolefins, particularly cyclohexenes, to form a variety of oxygenates. The catalyst used in the process is a covalently bonded iridium-heteropolyanion species. The process uses the catalyst in conjunction with a gaseous oxygen containing gas to form 2-cyclohexen-1-ol and also 2-cyclohexen-1-one.Type: GrantFiled: March 20, 1992Date of Patent: October 5, 1993Assignee: Catalytica, Inc.Inventors: Noritaka Mizuno, David K. Lyon, Richard G. Finke
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Patent number: 5234902Abstract: Described are alpha,3,3-trimethyl-1-cyclohexen-1-methanol derivative-containing composition having from about 85 up to about 90% by weight of a compound having the structure: ##STR1## and from about 10 up to about 15% by weight of a compound having the structure: ##STR2## wherein R.sub.1 is hydrogen or methyl and R.sub.2 is hydrogen or acetyl with the proviso that when R.sub.1 is methyl, R.sub.2 is hydrogen; and uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including but not limited to solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softener compositions, fabric softener articles and hair preparations; as well as processes for preparing said alpha,3,3-trimethyl-1-cyclohexen-1-methanol derivative-containing composition.Type: GrantFiled: July 28, 1992Date of Patent: August 10, 1993Assignee: International Flavors & Fragrances Inc.Inventor: Anthony T. Levorse, Jr.
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Patent number: 5229425Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing substantially all of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml. of said broth, containing not more than 0.06 ml of said oxidized limonene per ml. of said broth and incubated at 37.degree. C. in air for 60 minutes.Type: GrantFiled: May 29, 1992Date of Patent: July 20, 1993Assignee: Doyle E. ChastainInventors: Doyle E. Chastain, W. E. Sanders, Jr., Christine C. Sanders
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Patent number: 5202502Abstract: A chemically and optically pure B-halodiiso-2-ethylapopinocampheylborane of essentially 100% ee represented by the formula: ##STR1## wherein B is borane and X is halo, and a process of using such for the production of optically active alcohols.Type: GrantFiled: March 23, 1992Date of Patent: April 13, 1993Assignee: Aldrich Chemical Company, Inc.Inventor: Herbert C. Brown
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Patent number: 5187286Type: GrantFiled: March 25, 1991Date of Patent: February 16, 1993Assignee: Schering AktiengesellschaftInventors: Werner Skuballa, Bernd Buchmann, Josef Heindl, Wolfgang Frohlich, Roland Ekerdt