2,6,6-trialkylcyclohexenyl (e.g., Vitamin A Derivatives, Etc.) Patents (Class 568/668)
-
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
-
Publication number: 20100247551Abstract: Methods of identifying compounds that modulate lipocalin 2 activity or expression are described, as are methods of reducing insulin resistance or increasing insulin sensitivity by administering compounds that modulate lipocalin 2 expression. Methods of diagnosing insulin resistance or related conditions, by measuring lipocalin 2 activity, are also described.Type: ApplicationFiled: August 29, 2007Publication date: September 30, 2010Inventor: Evan D. Rosen
-
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
-
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
-
Publication number: 20040236154Abstract: The present invention relates to a method of conveniently and efficiently producing high-quality reduced coenzyme Q10 which is useful as an ingredient in foods, functional nutritive foods, specific health foods, nutritional supplements, nutrients, animal drugs, drinks, feeds, cosmetics, medicines, remedies, preventive drugs, etc. This method is suitable for industrial production thereof.Type: ApplicationFiled: June 1, 2004Publication date: November 25, 2004Inventors: Takahiro Ueda, Shiro Kitamura, Yasuyoshi Ueda
-
Patent number: 6180670Abstract: Skin aging and related conditions can be effectively treated with a conjugate of a retinoid and a bioactive organic acid preferably selected from among alpha-hydroxy acids, beta-hydroxy acids, and keto-acids; preferred conjugates include retinyl glycolyl ether and retinyl glycolate (as either the ester or reverse ester).Type: GrantFiled: January 25, 1999Date of Patent: January 30, 2001Assignee: Avon Products, Inc.Inventors: John A. Duffy, Janice J. Teal, Mark S. Garrison, George P. Serban
-
Patent number: 5908957Abstract: A process is disclosed for the catalyzed isomerization of a Z-isomer of a vitamin A compound or of a mixture of several of such isomers into a mixture of the corresponding all-E- and 13-Z-isomers of this vitamin A compound. The process utilizes nitrogen monoxide or a gas mixture containing nitrogen monoxide as the isomerization catalyst. Vitamin A acetate or vitamin A acid is preferably used as the vitamin A compound. The thus-produced all-E vitamin A and its alkanoyl esters have of all isomers by far the highest biological activity and are accordingly almost exclusively used in human and animal nutrition. The 13-Z-vitamin A compounds in turn play an important role as pharmaceutically active substances.Type: GrantFiled: January 26, 1998Date of Patent: June 1, 1999Assignee: Roche Vitamins Inc.Inventor: Angela Wildermann
-
Patent number: 5663459Abstract: 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: June 7, 1995Date of Patent: September 2, 1997Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Hugues Bienayme, Pierre Meilland
-
Patent number: 5313002Abstract: The invention relates to novel ethers and their use as aroma precursors. The ethers are derived from ionol and related compounds. These aroma precursors do not have a substantial aroma as such under ambient conditions, but will break up into a complex mixture having useful organoleptic properties under heating. The ethers are especially suitable for use in products which are heated, burned or smouldered in some stage of their use. The compounds according to the invention are especially suitable for application to tobacco. Mixtures obtained by degrading (e.g. by heating) the ethers according to the invention may be used in a flavouring or perfuming mixture as well due to their organoleptic properties.Type: GrantFiled: November 3, 1992Date of Patent: May 17, 1994Assignee: Unilever Patent Holdings B.V.Inventors: Johannes T. De Heij, Franciscus P. Van Lier, Harrie Renes
-
Patent number: 5243094Abstract: Derivatives of long-chain fatty alcohols, and methods of obtaining them, are provided, as well as pharmaceutical compositions containing derivatives and their uses, in particular in treating or preventing neuro-degenerative illnesses, conditions linked to skin ageing, the phenomena of thrombosis and atherosclerosis, and immune deficiencies.Type: GrantFiled: July 11, 1991Date of Patent: September 7, 1993Assignee: MedaforInventor: Jacques Borg
-
Patent number: 5066815Abstract: A process for preparing an optically active alcohol is disclosed, which comprises asymmetrically hydrogenating a carbonyl compound in the presence of a ruthenium-optically active phosphine complex as a catalyst. The resulting alcohol has high optical purity.Type: GrantFiled: May 8, 1990Date of Patent: November 19, 1991Assignee: Takasago International CorporationInventors: Noboru Sayo, Hidenori Kumobayashi, Susumo Akutagawa, Ryoji Noyori, Hidemasa Takaya
-
Patent number: 4952716Abstract: A process for the manufacture of compounds of the general formula ##STR1## wherein R.sup.1 signifies hydroxy or an etherified hydroxy group, and of zeaxanthin by converting a compound of the general formula ##STR2## wherein R.sup.1 has the above significance, in an inert organic solvent into the acetylenide and reacting this with methyl vinyl ketone, reducing the alcoholate obtained or the alcohol (obtained after hydrolysis of the alcoholate) of the general formula ##STR3## wherein R.sup.1 has the above significance, and subsequently hydrolyzing to give the compound of formula IV and, if desired, converting the compound of formula IV obtained into zeaxanthin.Type: GrantFiled: March 4, 1988Date of Patent: August 28, 1990Assignee: Hoffmann-La Roche Inc.Inventors: Teodor Lukac, Milan Soukup
-
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
-
Patent number: 4614747Abstract: This invention relates to novel compounds having pharmaceutical activity and having the general structure ##STR1## wherein the Z, R.sub.1, R.sub.2, R.sub.3, R.sub.4, n and m are defined within.Type: GrantFiled: November 29, 1984Date of Patent: September 30, 1986Assignee: USV Pharmaceutical Corp.Inventors: Bernard Loev, Howard Jones, Wan-kit Chan
-
Patent number: 4487944Abstract: New acetylenic and allenic carbinols of formula ##STR1## respectively, wherein symbol R stands for a trialkyl-silyl or a C.sub.1 to C.sub.6 alkyl radical, preferably a methyl, a tert-butyl or an isoamyl radical, or a group of formula ##STR2## wherein, when taken separately, each of symbols R.sup.1 and R.sup.2 represents a lower alkyl radical or, when taken together, R.sup.1 and R.sup.2 represent a tetramethylene group, are useful intermediates for the preparation of .beta.-damascenone.Type: GrantFiled: September 27, 1983Date of Patent: December 11, 1984Assignee: Firmenich, SAInventors: Karl-Heinrich Schulte-Elte, Bernard M/u/ ller
-
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
-
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
-
Patent number: 4296259Abstract: A new process for preparing 1-(3-oxo-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-methyl-1,4-pentadien-3-ol, a intermediate for canthaxanthin, from hydroxy-.beta.-ionone.Type: GrantFiled: June 9, 1980Date of Patent: October 20, 1981Assignee: Hoffmann-La Roche Inc.Inventor: Urs Hengartner
-
Patent number: 4227022Abstract: A total synthesis of canthaxanthin or dinor-canthaxanthin, known food coloring agents, from pentols.Type: GrantFiled: October 10, 1978Date of Patent: October 7, 1980Assignee: Hoffmann-La Roche Inc.Inventor: Michael Rosenberger