Vitamin A Alcohol Moiety Patents (Class 560/260)
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Patent number: 9187394Abstract: Provided in the present invention is a method for synthesizing 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde.Type: GrantFiled: December 10, 2012Date of Patent: November 17, 2015Assignees: Nanjing University of Technology, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical FactoryInventors: Chunlei Lv, Shiqing Pi, Jianhui Chen, Dingqiang Lu, Pingkai Ouyang
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Patent number: 9040742Abstract: The present invention relates to a process of production of a compound, which is useful as an intermediate (building block) in organic synthesis, especially in the synthesis of vitamin A or ?-carotene and derivatives thereof, e.g. canthaxanthin, astaxanthin or zeaxanthin.Type: GrantFiled: December 14, 2012Date of Patent: May 26, 2015Assignee: DSM IP ASSETS B.V.Inventors: Werner Bonrath, Bettina Wuestenberg, Thomas Netscher, Jan Schuetz
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Patent number: 8791290Abstract: The invention provides an acetal compound containing an adamantane ring having an alcoholic hydroxyl group which is protected with an acetal group having a carbonyl moiety of branched structure. A photoresist film comprising a polymer comprising recurring units derived from the acetal compound and an acid generator is characterized by a high dissolution contrast when it is subjected to exposure and organic solvent development to form an image via positive/negative reversal.Type: GrantFiled: March 23, 2011Date of Patent: July 29, 2014Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Koji Hasegawa, Jun Hatakeyama, Takeshi Nagata, Seiichiro Tachibana, Takeshi Kinsho
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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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Patent number: 8263802Abstract: A process for redissociating Michael adducts which are present in a liquid F with a proportion by weight of ?10% by weight and have been formed in the preparation of acrylic acid or esters thereof in a redissociating apparatus which comprises a pump P, a separating column K with separating internals and a circulation heat exchanger UW, wherein, for the purpose of supplying the cleavage energy, the pump P sucks in bottoms liquid from the bottom space of the separating column K and, via the circulation heat exchanger UW, continually recycles it into the bottom space above the level of the bottoms liquid, and wherein the pump P is a radial circulation pump with an open impeller.Type: GrantFiled: December 9, 2009Date of Patent: September 11, 2012Assignee: BASF SEInventors: Volker Schliephake, Thorsten Friese, Klaus Bott, Michael Blechschmitt, Till Blum, Klaus Joachim Mueller-Engel
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Patent number: 7279180Abstract: The present invention relates to stable emulsions and dry powders of mixtures of fat-soluble vitamins, and to processes for their preparation and to their use.Type: GrantFiled: November 18, 2002Date of Patent: October 9, 2007Assignee: BASF AktiengesellschaftInventors: Wolfgang Hähnlein, Morten Mohr Hansen, Jes Elenius Olesen, Anne Grethe Tobiasen
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Patent number: 6870066Abstract: A method for the decomposition of a Michael type adduct of an acrylic acid and/or an acrylic ester represented by the following formula [I] or [II] is disclosed, wherein decomposing the Michael type adduct in the presence of at least one copper salt and at least one metal salt selected from the group consisting of an alkali metal salt and an alkaline earth metal salt into an acrylic acid and/or an acrylic ester and/or an alcohol. CH2?CHCOO(—X—COO)n—R1??[I] R2—O(—X—COO)m—R3??[II] (wherein n and m denote an integer in the range of 1-5, R1, R2, and R3 independently denote a hydrogen atom or an alkyl group, and —X— denotes —CH2CH2— or —CH(CH3)—, and —X— may be identical or different when n is 2 or more).Type: GrantFiled: March 10, 2003Date of Patent: March 22, 2005Assignee: Nippon Shokubai Co., LTDInventors: Fumio Shibusawa, Naoki Serata, Kazuhiko Sakamoto
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Patent number: 6727381Abstract: The invention relates to a process for producing all trans-vitamin A ester (I). According to the present invention, vitamin A ester (I) can simply be synthesized in good yields and high purity by the reaction of phosphonate compound (IV) with aldehyde (II) in an organic solvent in the presence of a base.Type: GrantFiled: January 3, 2002Date of Patent: April 27, 2004Assignee: Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutical FactoryInventors: Runpu Shen, Shiqing Pi, Bin Xie, Hongjun Huang
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Publication number: 20030229239Abstract: Lutein and zeaxanthin, the main carotenoids in marigold flowers, and capsanthin and capsorubin, the main carotenoids in red peppers are esterified mainly with C-18 fatty acids. The pigments were re-esterified without isolating them from the natural saponified extract using carboxylic acids in the range of C-1 to C-12 and their corresponding metallic salts in the presence of a catalyzing agent. Both the diester and monoester forms were obtained. It is expected that the pigment esters with a fatty acid of 12 or less carbons will have a better digestibility than the esters of xanthophylls in their natural state and better stability than the hydrolyzed xanthophylls. This will result in a better pigmentation capacity of the carotenoids for poultry or aquaculture.Type: ApplicationFiled: March 26, 2003Publication date: December 11, 2003Inventors: Mario D.T. Cordona, Gustavo Rodriguez
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Patent number: 6552219Abstract: There are provided a dihalogen derivative represented by formula (2): wherein X represents a halogen atom and R2 represents a protective group for a hydroxyl group; a process for producing the same; and a process for producing vitamin A by use of said dihalogen derivative.Type: GrantFiled: December 5, 2000Date of Patent: April 22, 2003Assignee: Sumitomo Chemical Company, Ltd.Inventors: Toshiya Takahashi, Atsushi Furutani, Shinzo Seko
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Patent number: 6531157Abstract: The present invention relates to stable emulsions and dry powders of mixtures of fat-soluble vitamins, and to processes for their preparation and to their use.Type: GrantFiled: March 21, 2000Date of Patent: March 11, 2003Assignee: BASF AktiengesellschaftInventors: Wolfgang Hähnlein, Morten Mohr Hansen, Jes Elenius Olesen, Anne Grethe Tobiasen
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Publication number: 20020151742Abstract: The invention relates to a process for producing all trans-vitamin A ester (I). According to the present invention, vitamin A ester (I) can simply be synthesized in good yields and high purity by the reaction of phosphonate compound (IV) with aldehyde (II) in an organic solvent in the presence of a base.Type: ApplicationFiled: January 3, 2002Publication date: October 17, 2002Inventors: Runpu Shen, Shiqing Pi, Bin Xie, Hongjun Huang
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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: 6264986Abstract: The present invention relates to stable emulsions and dry powders of mixtures of fat-soluble vitamins, and to processes for their preparation and to their use.Type: GrantFiled: October 9, 1997Date of Patent: July 24, 2001Assignee: BASF AktiengesellschaftInventors: Wolfgang Hähnlein, Morten Mohr Hansen, Jes Elenius Olesen, Anne Grethe Tobiasen
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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
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Patent number: 5902738Abstract: A process for making a compound of formula ##STR1## wherein R signifies a C.sub.1-23 -alkyl group or a C.sub.2-23 -alkenyl group containing 1 to 3 double bonds, comprising the steps of (a) reacting a compound of formula ##STR2## with an acylating agent which is in a mixture comprising (i) an organic solvent and (ii) a lipase which is present in suspension, so as to form the compound of formula I; and (b) recovering the compound of formula I is provided for. The process can be used to make (11Z,13Z)-7,10-dihydro-10-hydroxy-retinyl acetate, an starting material for the production of vitamin A acetate.Type: GrantFiled: March 31, 1997Date of Patent: May 11, 1999Assignee: Roche Vitamins Inc.Inventors: Bernard Orsat, Paul Spurr, Beat Wirz
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Patent number: 5726328Abstract: A method for the production of .omega.-haloalkyl esters which are useful as intermediates in the synthesis of cis-oxacycloheptadec-11-en-2-one (Product I) and cis-oxacycloheptadec-12-en-2-one (Product II). Also disclosed is a process for the synthesis of Products I-II and a method for using Products I-II to impart an ambery or musky smell to a fragrance composition. Finally, fragrance compositions including Products I-II are disclosed as well as end products such as perfume extracts, toilet waters, cosmetic preparations, soaps, detergents and functional products, each of which also contains at least one of Products I-II.Type: GrantFiled: July 9, 1996Date of Patent: March 10, 1998Assignee: V. Mane Fils S.A.Inventors: Maurice Mane, Jean-Louis Ponge
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Patent number: 5424478Abstract: The present specification relates to an industrially advantageous process for producing vitamin A derivatives which are useful as medicaments, feed additives, food additives and the like. The process provides vitamin A derivatives, particularly all-trans vitamin A derivatives in high yield and purity.Type: GrantFiled: March 22, 1994Date of Patent: June 13, 1995Assignee: Takeda Chemical Industries, Ltd.Inventors: Mitsutaka Tanaka, Tadashi Hanaoka, Kunio Takanohashi
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Patent number: 5321007Abstract: Described are 2,6-dimethylbicyclo[3.3.1]non-6-ene-3-methanol and substituted derivatives thereof defined according to the generic structure: ##STR1## wherein each of the dashed lines represents a carbon-oxygen covalent bond or no bond; N is 0 or 1; R.sub.1 represents hydrogen, C.sub.1 -C.sub.2 lower alkyl, lower alkenyl, lower alkylenyl, C.sub.1 -C.sub.2 acyl, alkoxycarbonyl, magnesium halo or lithium; and R.sub.2 represents methyl or hydrogen as well as uses thereof (wherein R.sub.1 is not magnesium halo or lithium) for augmenting or enhancing the aroma of consumable materials selected from the group consisting of perfume compositions, perfumed articles, colognes, deodorizing articles, deodorizing compositions and malodor maskants.Type: GrantFiled: October 27, 1993Date of Patent: June 14, 1994Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, Matthew J. McGinnis, Leroy P. John, Franc T. Schiet, Charles E. J. Beck
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Patent number: 5276209Abstract: An improved process for the preparation of polyenes by the Julia reaction comprises carrying out the allylation of the anion of an allyl aryl sulfone generated a strong base, and the elimination of arylsulfinic acid to form a double bond in the same inert polar solvent which is immiscible with water, preferably in a ketone of the formula IR.sup.1 --CO--R.sup.2 (I)where R.sup.1 and R.sup.2 are each straight-chain or branched alkyl of 2 to 4 carbons, or R.sup.1 and R.sup.2 together are tetramethylene or pentamethylene. The process is particularly important for the preparation of vitamin A derivatives. In the preparation of vitamin A aldehyde, for example, it is advantageous to use the same alkali metal alcoholate as strong base in both stages so that the conversion can be carried out as one-pot reaction.Type: GrantFiled: July 17, 1992Date of Patent: January 4, 1994Assignee: BASF AktiengesellschaftInventors: Hagen Jaedicke, Klaus Kaiser, Manfred Hamm
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Patent number: 5191110Abstract: According to this process, one effects a stereospecific reduction of the two hydroxyl groups of an ether-diol by a mixture (titanium trichloride, lithium aluminum hydride) at a temperature between 5.degree. C. and about 40.degree. C. and that optionally, one converts the resulting ether into vitamin A, retinol or retinoic acid.Application to the synthesis of all-trans compounds selected from the group consisting of vitamin A and its ethers, retinol and retinoic acid, and their 13-cis isomers.Type: GrantFiled: April 21, 1992Date of Patent: March 2, 1993Assignee: L'OrealInventors: Guy Solladie, Serge Forestier, Gerard Lang
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Patent number: 5155255Abstract: A process for the manufacture of certain cycloalkenylalkenes, e.g. vitamin A acetate, comprises dehydrating 1-(5-acetoxy-3-methyl-penta-1,3-dienyl)-2,6,6-trimethyl-cyclo hexanol or 4 aetoxy-1-(5-acetoxy-3-methyl-penta-1,3-dienyl)-2,6,6-trimethyl-cyclohexano l or 1-(9-acetoxy-3,7-dimethyl-4-hydroxy-nona-2,5,7-trienyl)-2,6,6-trimethyl- cyclohexene in the presence of an alkali metal bromide or of manganese bromide or of a hydrate of such a bromide as the catalyst and in an organic solvent.The products are especially suitable as intermediates in carotinoid syntheses.Type: GrantFiled: March 25, 1991Date of Patent: October 13, 1992Assignee: Hoffmann-La Roche Inc.Inventors: Mario Mazzuchelli, Milan Soukup, Paul Spurr, Claude Stritt
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Patent number: 4825006Abstract: A process for producing vitamin A represented by the formula ##STR1## which comprises treating a compound represented by the formula ##STR2## wherein R.sup.1 represents an aryl group which may be substituted, R.sup.21 and R.sup.22 each represents a hydrogen atom or a lower alkanoyl group, R.sup.3 represents an acetal-type protective group for a hydroxyl group, and X represents a halogen atom, with a base; and novel intermediate compounds useful for the above process.Type: GrantFiled: December 3, 1985Date of Patent: April 25, 1989Assignee: Kuraray Co., Ltd.Inventors: Junzo Otera, Tadakatsu Mandai, Mikio Kawada
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Patent number: 4751307Abstract: Disclosed are improved Wittig reaction processes wherein the Wittig reaction is conducted in an anisole containing solvent.Type: GrantFiled: February 27, 1987Date of Patent: June 14, 1988Assignee: Mallinckrodt, Inc.Inventor: Carl R. White
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Patent number: 4587366Abstract: A process is described for preparing fluoroalkyl-substituted iodoalkanes by reacting a fluorinated alkyl iodide with a substituted or unsubstituted alkene under heat in the presence of a catalyst. The catalyst is at least one metal which, in the periodic table of the elements, has one of the atomic numbers 24 to 30, 42 to 48 or 74 to 79 and is in finely divided form. The products of the process according to the invention are addition compounds of the fluorinated alkyl iodide with the substituted or unsubstituted alkene and, in known processes, can be used as useful intermediates for preparing fluorine-containing polymers, textile finishes, fire-extinguishing agents or surfactants.Type: GrantFiled: October 19, 1984Date of Patent: May 6, 1986Assignee: Hoechst AktiengesellschaftInventor: Konrad von Werner
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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: 4336401Abstract: A novel method of preparing 1-crotonoyl-2,6,6-trimethylcyclohexa-1,3-diene comprises treating an ester of the formula ##STR1## with a proton acid under essentially anhydrous conditions.Type: GrantFiled: July 17, 1980Date of Patent: June 22, 1982Assignee: Hercules IncorporatedInventor: Lumbertus A. Hulshof
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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: 4254281Abstract: There is disclosed a novel process for the preparation of vitamin A acetate whereby .gamma.-acetoxy-tiglic aldehyde is reacted with the salt formed by the reaction of vinyl-.beta.-ionol, triphenylphosphine and an acid.Type: GrantFiled: July 25, 1979Date of Patent: March 3, 1981Assignee: Hoffmann-La Roche Inc.Inventors: Kuno Schleich, Hansjorg Stoller
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Patent number: 4175205Abstract: Vitamin A alcohol and its lower alkanoic esters are prepared by desulphonation of corresponding sulphones with a solid potassium alcoholate of a primary or secondary lower alcohol at 10.degree. to 50.degree. C. in an anhydrous liquid hydrocarbon.Type: GrantFiled: July 25, 1977Date of Patent: November 20, 1979Assignee: Rhone-Poulenc IndustriesInventor: Jean-Pierre Decor
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Patent number: 4147708Abstract: A novel procedure for the preparation of carotenoids, particularly vitamin A, employing .pi.-allyl transition metal complexes. Novel carotenoid intermediates are also disclosed.Type: GrantFiled: May 2, 1977Date of Patent: April 3, 1979Assignee: Hoffmann-La Roche Inc.Inventor: Percy S. Manchand
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Patent number: 4127608Abstract: A synthesis of Vitamin E has the condensation of 2,4-pentanediene and 1,2-epoxy-2,6,10,14-tetramethylpentadecane including intermediates in this synthesis which uses base catalyzed condensations of aliphatic compounds to construct the Vitamin E molecule from aliphatic precursors.Type: GrantFiled: May 17, 1977Date of Patent: November 28, 1978Assignee: Hoffmann-La Roche Inc.Inventors: Gary L. Olson, Galbriel Saucy
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Patent number: 4115415Abstract: A process for the production of an alkylene glycol ether ester of an organic carboxylic acid which comprises the step of reacting an alkylene oxide with an ester of organic carboxylic acid in accordance with the following reaction equation: ##STR1## wherein R" is a substituted or non-substituted hydrocarbon having 1 to 20 carbon atoms or a hydrogen atom;R'" is a substituted or non-substituted hydrocarbon having 1 to 20 carbon atoms;R.sup.3 are each the same or different substituted or non-substituted hydrocarbon having 1 to 10 carbon atoms or a hydrogen atom;Q is simultaneously the same or different groups X, R, OR, SR, NR.sub.2 or PR.sub.2 (wherein X is a halogen atom selected from the group consisting of Cl, Br, and I, and R is the same or different substituted or non-substituted hydrocarbon having 1 to 20 carbon atoms or a hydrogen atom, and a combination of all Q=R does not occur).Type: GrantFiled: October 22, 1976Date of Patent: September 19, 1978Assignee: Nisso Petrochemical Industries Co., Ltd.Inventors: Hiroshi Yoshihara, Takashi Tobita, Ryoichi Tomizawa, Kunio Ishikawa
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Patent number: 4082791Abstract: A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.Type: GrantFiled: February 17, 1976Date of Patent: April 4, 1978Assignee: SCM CorporationInventor: William Oroshnik
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Patent number: 4072719Abstract: Theaspiran is a novel fragrance and flavor substance. Its uses and novel process for making it are disclosed.Type: GrantFiled: October 19, 1976Date of Patent: February 7, 1978Assignee: Givaudan CorporationInventor: Peter Naegeli
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Patent number: 4066685Abstract: A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.Type: GrantFiled: April 10, 1975Date of Patent: January 3, 1978Assignee: SCM CorporationInventor: William Oroshnik
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Patent number: 4064162Abstract: A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.Type: GrantFiled: February 17, 1976Date of Patent: December 20, 1977Assignee: SCM CorporationInventor: William Oroshnik
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Patent number: 4064183Abstract: A synthesis of novel Vitamin A intermediates from beta-ionone is described as well as a conversion of the intermediates to Vitamin A. The length of the conjugated aliphatic side chain of beta-ionone is increased while still ultimately obtaining the desired trans form of Vitamin A. In general, beta-ionone is ethynylated to ethynyl-beta-ionol, the hydroxyl of which is etherified to form an ethynyl-terminated, alkoxy-substituted, beta-ionol intermediate. The intermediate is coupled through its copper derivative with a compound like chloro-isopentenyl acetate to produce a C.sub.20 skeleton. By semi-hydrogenation, the acetylenic bond on the C.sub.20 skeleton is converted to an ethylenic bond, and by hydrolysis the terminal ester moiety is converted to a hydroxyl group. Treatment with a strong base removes the alkoxy group to produce Vitamin A.Type: GrantFiled: March 1, 1976Date of Patent: December 20, 1977Assignee: SCM CorporationInventor: William Oroshnik
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Patent number: 4049682Abstract: Described are processes for preparing enol esters having the generic structure: ##STR1## (which structure is intended to cover both the "cis" and the "trans" isomers thereof) wherein R.sub.1 is C.sub.1 -C.sub.11 alkyl, and R.sub.4 is hydrogen or methyl, produced by one of the following processes:I. Reacting beta-ionone or a homologue thereof with a peracid;Ii. Reacting an enol acetate formed by process (i) (when R.sub.1 is methyl and R.sub.4 is hydrogen) with an alkanoic acid anhydride or an acyl halide, to form another enol ester;Iii. Reacting beta-cyclohomocitral having the formula: ##STR2## with a lower alkanoic acid anhydride or an acyl halide.Type: GrantFiled: September 15, 1976Date of Patent: September 20, 1977Assignee: International Flavors & Fragrances Inc.Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals