Vitamin A Alcohol Moiety Patents (Class 560/260)
  • Patent number: 9187394
    Abstract: Provided in the present invention is a method for synthesizing 2,7-dimethyl-2,4,6-octatriene-1,8-dialdehyde.
    Type: Grant
    Filed: December 10, 2012
    Date of Patent: November 17, 2015
    Assignees: Nanjing University of Technology, Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory
    Inventors: Chunlei Lv, Shiqing Pi, Jianhui Chen, Dingqiang Lu, Pingkai Ouyang
  • Patent number: 9040742
    Abstract: 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: Grant
    Filed: December 14, 2012
    Date of Patent: May 26, 2015
    Assignee: DSM IP ASSETS B.V.
    Inventors: Werner Bonrath, Bettina Wuestenberg, Thomas Netscher, Jan Schuetz
  • Patent number: 8791290
    Abstract: 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: Grant
    Filed: March 23, 2011
    Date of Patent: July 29, 2014
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Koji Hasegawa, Jun Hatakeyama, Takeshi Nagata, Seiichiro Tachibana, Takeshi Kinsho
  • Publication number: 20130072559
    Abstract: Compositions of and methods for using synthetic retinal derivatives as retinoid replacements and opsin agonists are provided.
    Type: Application
    Filed: September 14, 2012
    Publication date: March 21, 2013
    Applicant: UNIVERSITY OF WASHINGTON
    Inventors: Krzysztof PALCZEWSKI, Matthew Batten
  • Patent number: 8263802
    Abstract: 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: Grant
    Filed: December 9, 2009
    Date of Patent: September 11, 2012
    Assignee: BASF SE
    Inventors: Volker Schliephake, Thorsten Friese, Klaus Bott, Michael Blechschmitt, Till Blum, Klaus Joachim Mueller-Engel
  • Patent number: 7279180
    Abstract: 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: Grant
    Filed: November 18, 2002
    Date of Patent: October 9, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hähnlein, Morten Mohr Hansen, Jes Elenius Olesen, Anne Grethe Tobiasen
  • Patent number: 6870066
    Abstract: 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: Grant
    Filed: March 10, 2003
    Date of Patent: March 22, 2005
    Assignee: Nippon Shokubai Co., LTD
    Inventors: Fumio Shibusawa, Naoki Serata, Kazuhiko Sakamoto
  • Patent number: 6727381
    Abstract: 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: Grant
    Filed: January 3, 2002
    Date of Patent: April 27, 2004
    Assignee: Zhejiang Medicine Co., Ltd., Xinchang Pharmaceutical Factory
    Inventors: Runpu Shen, Shiqing Pi, Bin Xie, Hongjun Huang
  • Publication number: 20030229239
    Abstract: 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: Application
    Filed: March 26, 2003
    Publication date: December 11, 2003
    Inventors: Mario D.T. Cordona, Gustavo Rodriguez
  • Patent number: 6552219
    Abstract: 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: Grant
    Filed: December 5, 2000
    Date of Patent: April 22, 2003
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Toshiya Takahashi, Atsushi Furutani, Shinzo Seko
  • Patent number: 6531157
    Abstract: 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: Grant
    Filed: March 21, 2000
    Date of Patent: March 11, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hähnlein, Morten Mohr Hansen, Jes Elenius Olesen, Anne Grethe Tobiasen
  • Publication number: 20020151742
    Abstract: 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: Application
    Filed: January 3, 2002
    Publication date: October 17, 2002
    Inventors: Runpu Shen, Shiqing Pi, Bin Xie, Hongjun Huang
  • Patent number: 6348622
    Abstract: 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: Grant
    Filed: February 9, 2000
    Date of Patent: February 19, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiya Takahashi, Shinzo Seko, Takashi Miki
  • Patent number: 6264986
    Abstract: 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: Grant
    Filed: October 9, 1997
    Date of Patent: July 24, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Hähnlein, Morten Mohr Hansen, Jes Elenius Olesen, Anne Grethe Tobiasen
  • Patent number: 6180670
    Abstract: 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: Grant
    Filed: January 25, 1999
    Date of Patent: January 30, 2001
    Assignee: Avon Products, Inc.
    Inventors: John A. Duffy, Janice J. Teal, Mark S. Garrison, George P. Serban
  • Patent number: 5902738
    Abstract: 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: Grant
    Filed: March 31, 1997
    Date of Patent: May 11, 1999
    Assignee: Roche Vitamins Inc.
    Inventors: Bernard Orsat, Paul Spurr, Beat Wirz
  • Patent number: 5726328
    Abstract: 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: Grant
    Filed: July 9, 1996
    Date of Patent: March 10, 1998
    Assignee: V. Mane Fils S.A.
    Inventors: Maurice Mane, Jean-Louis Ponge
  • Patent number: 5424478
    Abstract: 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: Grant
    Filed: March 22, 1994
    Date of Patent: June 13, 1995
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Mitsutaka Tanaka, Tadashi Hanaoka, Kunio Takanohashi
  • Patent number: 5321007
    Abstract: 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: Grant
    Filed: October 27, 1993
    Date of Patent: June 14, 1994
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, Matthew J. McGinnis, Leroy P. John, Franc T. Schiet, Charles E. J. Beck
  • Patent number: 5276209
    Abstract: 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: Grant
    Filed: July 17, 1992
    Date of Patent: January 4, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Hagen Jaedicke, Klaus Kaiser, Manfred Hamm
  • Patent number: 5191110
    Abstract: 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: Grant
    Filed: April 21, 1992
    Date of Patent: March 2, 1993
    Assignee: L'Oreal
    Inventors: Guy Solladie, Serge Forestier, Gerard Lang
  • Patent number: 5155255
    Abstract: 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: Grant
    Filed: March 25, 1991
    Date of Patent: October 13, 1992
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Mario Mazzuchelli, Milan Soukup, Paul Spurr, Claude Stritt
  • Patent number: 4825006
    Abstract: 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: Grant
    Filed: December 3, 1985
    Date of Patent: April 25, 1989
    Assignee: Kuraray Co., Ltd.
    Inventors: Junzo Otera, Tadakatsu Mandai, Mikio Kawada
  • Patent number: 4751307
    Abstract: Disclosed are improved Wittig reaction processes wherein the Wittig reaction is conducted in an anisole containing solvent.
    Type: Grant
    Filed: February 27, 1987
    Date of Patent: June 14, 1988
    Assignee: Mallinckrodt, Inc.
    Inventor: Carl R. White
  • Patent number: 4587366
    Abstract: 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: Grant
    Filed: October 19, 1984
    Date of Patent: May 6, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Konrad von Werner
  • Patent number: 4474983
    Abstract: 1,5-Dimethyl-hexa-1,5-dienylene compounds, and especially Vitamin A and derivatives thereof, are made by desuphonylating with a basic reagent a sulphone of the formula: ##STR1## in which the sulphonyl group --SO.sub.2 R replaces a hydrogen atom on carbon atom (a) or (b), R represents a phenyl or napthyl group, A is 2-(2,6,6-trimethylcyclohex-1-enyl)ethenyl, and Q is --CH.sub.2 OH or an ether or ester thereof, CHO, or an acetal group.
    Type: Grant
    Filed: February 4, 1982
    Date of Patent: October 2, 1984
    Assignee: Rhone-Poulenc S.A.
    Inventors: Pierre Chabardes, Marc Julia, Albert Menet
  • Patent number: 4336401
    Abstract: 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: Grant
    Filed: July 17, 1980
    Date of Patent: June 22, 1982
    Assignee: Hercules Incorporated
    Inventor: Lumbertus A. Hulshof
  • Patent number: 4331814
    Abstract: Sulphones useful for preparing polyenes have the formula: ##STR1## where the sulphonyl group replaces a hydrogen atom on carbon atom (a) or (b), R represents alkyl, aralkyl or aryl, optionally substituted, A and Q represent an optionally substituted hydrocarbon of 5n+1 carbon atoms (n is 1-5), methyl, optionally substituted by halogen, sulphide or sulphone, CH.sub.2 OH (or an ether or ester thereof), CHO (optionally protected), COOH (or an acid chloride, ester or nitrile thereof), with the proviso that when A represents a 2-(2,6,6-trimethylcyclohex-1-enyl) ethenyl radical, Q cannot represent --COOH or an ester thereof.
    Type: Grant
    Filed: February 1, 1973
    Date of Patent: May 25, 1982
    Assignee: Rhone Poulenc S.A.
    Inventors: Pierre Chabardes, Marc Julia, Albert Menet
  • Patent number: 4254281
    Abstract: 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: Grant
    Filed: July 25, 1979
    Date of Patent: March 3, 1981
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Kuno Schleich, Hansjorg Stoller
  • Patent number: 4175205
    Abstract: 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: Grant
    Filed: July 25, 1977
    Date of Patent: November 20, 1979
    Assignee: Rhone-Poulenc Industries
    Inventor: Jean-Pierre Decor
  • Patent number: 4147708
    Abstract: A novel procedure for the preparation of carotenoids, particularly vitamin A, employing .pi.-allyl transition metal complexes. Novel carotenoid intermediates are also disclosed.
    Type: Grant
    Filed: May 2, 1977
    Date of Patent: April 3, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Percy S. Manchand
  • Patent number: 4127608
    Abstract: 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: Grant
    Filed: May 17, 1977
    Date of Patent: November 28, 1978
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Gary L. Olson, Galbriel Saucy
  • Patent number: 4115415
    Abstract: 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: Grant
    Filed: October 22, 1976
    Date of Patent: September 19, 1978
    Assignee: Nisso Petrochemical Industries Co., Ltd.
    Inventors: Hiroshi Yoshihara, Takashi Tobita, Ryoichi Tomizawa, Kunio Ishikawa
  • Patent number: 4082791
    Abstract: 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: Grant
    Filed: February 17, 1976
    Date of Patent: April 4, 1978
    Assignee: SCM Corporation
    Inventor: William Oroshnik
  • Patent number: 4072719
    Abstract: Theaspiran is a novel fragrance and flavor substance. Its uses and novel process for making it are disclosed.
    Type: Grant
    Filed: October 19, 1976
    Date of Patent: February 7, 1978
    Assignee: Givaudan Corporation
    Inventor: Peter Naegeli
  • Patent number: 4066685
    Abstract: 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: Grant
    Filed: April 10, 1975
    Date of Patent: January 3, 1978
    Assignee: SCM Corporation
    Inventor: William Oroshnik
  • Patent number: 4064162
    Abstract: 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: Grant
    Filed: February 17, 1976
    Date of Patent: December 20, 1977
    Assignee: SCM Corporation
    Inventor: William Oroshnik
  • Patent number: 4064183
    Abstract: 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: Grant
    Filed: March 1, 1976
    Date of Patent: December 20, 1977
    Assignee: SCM Corporation
    Inventor: William Oroshnik
  • Patent number: 4049682
    Abstract: 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: Grant
    Filed: September 15, 1976
    Date of Patent: September 20, 1977
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan Owen Pittet, Erich Manfred Klaiber, Manfred Hugo Vock, Edward J. Shuster, Joaquin Vinals