2,6,6-trialkylcyclohexenyls (e.g., Vitamin A, Etc.) Patents (Class 568/824)
  • Patent number: 4250049
    Abstract: Described is a process for augmenting or enhancing the aroma of a solid or liquid anionic, cationic or nonionic detergent comprising the step of adding to a solid or liquid anionic, cationic or nonionic detergent base from 0.005% up to 5% by weight of at least one compound defined according to the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 is hydrogen; wherein the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond with the proviso that when R.sub.1 is hydrogen, the dashed line represents a carbon-carbon double bond.
    Type: Grant
    Filed: February 8, 1980
    Date of Patent: February 10, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard A. Wilson, William L. Schreiber, Braja D. Mookherjee, Jacob Kiwala, Joaquin F. Vinals, Manfred H. Vock, Gilbert Stork, Frederick L. Schmitt
  • Patent number: 4243823
    Abstract: Processes and compositions are described for use in foodstuff, chewing gum, toothpaste and medicinal product flavor and aroma, smoking tobacco flavor and aroma and perfume and perfumed article aroma augmenting, enhancing and imparting compositions; and as foodstuff, chewing gum, toothpaste, medicinal product, smoking tobacco, perfume and perfumed article aroma and/or flavor imparting materials of 2,6,6-trimethyl-.alpha.-(iso)propenyl-1-cyclohexene-1-methanol and -1,3-cyclohexadiene-1-methanol derivatives or one or more of their geometric or stereoisomers as defined by the generic structure: ##STR1## wherein one of R.sub.1, R.sub.2 or R.sub.3 is methyl and the other two of R.sub.1, R.sub.2 and R.sub.3 represents hydrogen; the dashed line is a carbon-carbon double bond or a carbon-carbon single bond; with the proviso that when R.sub.1 is hydrogen, the dashed line is a carbon-carbon double bond.Addition of one or more of the 2,6,6-trimethyl-.alpha.
    Type: Grant
    Filed: May 15, 1979
    Date of Patent: January 6, 1981
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard A. Wilson, William L. Schreiber, Braja D. Mookherjee, Jacob Kiwala, Joaquin F. Vinals, Manfred H. Vock, Gilbert Stork, Frederick L. Schmitt
  • Patent number: 4233464
    Abstract: 1-[3-Methyl-3,5,5-trialkoxy-pent-1-yn-1-yl]-2,6-dimethyl-cyclohex-1-enes, which may or may not be methyl-substituted in the 2- and/or 6-position, are obtained by reacting the corresponding 1-[3-methyl-but-1-yn-3-en-1-yl]-2,6-dimethyl-cyclohex-1-enes with orthoformic acid esters in the presence of acid condensing agents. The new compounds provide a new method of access to the compounds of carotinoid chemistry, especially to vitamin A, which avoids the conventional expensive synthesis via phosphorus ylide compounds.
    Type: Grant
    Filed: April 12, 1978
    Date of Patent: November 11, 1980
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Baumann, Werner Hoffmann
  • Patent number: 4227022
    Abstract: A total synthesis of canthaxanthin or dinor-canthaxanthin, known food coloring agents, from pentols.
    Type: Grant
    Filed: October 10, 1978
    Date of Patent: October 7, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Michael Rosenberger
  • Patent number: 4215230
    Abstract: Ionones and irones are produced by thermal rearrangement of novel propargylic alcohols, as follows: ##STR1## wherein R.sup.1 is a lower alkyl group, R.sup.2 is hydrogen or methyl and the dotted lines in the product formula reflect the existence of a double bond at either one or the other of the positions indicated.
    Type: Grant
    Filed: May 23, 1978
    Date of Patent: July 29, 1980
    Assignee: Kuraray Co., Ltd.
    Inventors: Takashi Ohnishi, Yoshiji Fujita, Michihiro Ishiguro, Takashi Nishida
  • Patent number: 4202994
    Abstract: Described are substituted 1-oxyalkyl-2,6,6-trimethylcyclohexene derivatives having the generic structure: ##STR1## wherein R.sub.1 is one of OH, ##STR2## OMgX or H; R.sub.2 is ##STR3## OH, OMgX, CH.sub.3, H; R.sub.3 is one of methyl, ethyl, 1-propyl or 2-propyl; X is chloro, bromo or iodo; R.sub.6 is hydrogen or no moiety; one of the wavy lines is a carbon-carbon double and the other of the wavy lines is a carbon-carbon single bond; with the first proviso that when the .DELTA..sup.2,3 bond is a carbon-carbon double bond, then R.sub.6 is hydrogen and the moieties R.sub.6 and ##STR4## are so juxtaposed as to give rise to two different groups of stereoisomers of the molecular genus: ##STR5## and with the second proviso that when R.sub.1 is one of ##STR6## OH or OMgX then R.sub.2 is hydrogen or methyl; and when R.sub.2 is one of ##STR7## OH or OMgX then R.sub.1 is hydrogen.
    Type: Grant
    Filed: January 16, 1979
    Date of Patent: May 13, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Robert W. Trenkle, Braja D. Mookherjee, Robin L. Kasper, Manfred H. Vock
  • Patent number: 4196306
    Abstract: Process intermediates are described herein having the generic structure: ##STR1## wherein X is selected from the group consisting of chloro, bromo and iodo; R.sub.3 is hydrogen or does not represent any group; wherein one of the wavy lines is a carbon-carbon double bond and the other of the wavy lines is a carbon-carbon single bond; with the proviso that when the .DELTA..sup.2,3 bond is a carbon-carbon double bond, then R.sub.3 is hydrogen and R.sub.3 and the moiety: ##STR2## are so juxtaposed that the molecule having the structure: ##STR3## exists in two different isomeric forms; a "+" form and "-" form.
    Type: Grant
    Filed: May 15, 1979
    Date of Patent: April 1, 1980
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Robert W. Trenkle, Braja D. Mookherjee, Robin Kasper, Manfred H. Vock, Joaquin Vinals, Jacob Kiwala, Frederick L. Schmitt
  • 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: 4156100
    Abstract: A process for fermentatively hydrogenating and reducing ketoisophorone to produce optically active [4R,6R]-4-hydroxy-2,6,6-trimethyl-cyclohexanone useful as an intermediate in the production of optically active carotenoids and intermediates in the production of these carotenoids.
    Type: Grant
    Filed: November 7, 1977
    Date of Patent: May 22, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Walter Boguth, Hans G. W. Leuenberger, Hans J. Mayer, Erich Widmer, Reinhard Zell
  • Patent number: 4147886
    Abstract: A process for the preparation of ethynyl-.beta.-ionol involving the reaction of acetylene and .beta.-ionone in the presence of an alkali metal hydroxide in liquid ammonia is disclosed.
    Type: Grant
    Filed: June 21, 1977
    Date of Patent: April 3, 1979
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Hermann Wiederkehr
  • 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: 4120830
    Abstract: Spirane derivatives, most of them are new, useful as odor-modifying ingredients for manufacturing perfumes and perfumed products, and as flavor-modifying ingredients for the manufacture of artificial flavors of for flavoring foodstuffs, animal feeds, beverages, pharmaceutical preparations and tobacco products.Process for preparing said spirane derivatives.
    Type: Grant
    Filed: October 1, 1976
    Date of Patent: October 17, 1978
    Assignee: Firmenich SA
    Inventors: Walter Renold, Werner Skorianetz, Karl-Heinrich Schulte-Elte, Gunther Ohloff
  • Patent number: 4105855
    Abstract: Symmetrical carotenoids are prepared from the half-molecules by dimerizing the phosphonium salts of the half-molecules with peroxides, peroxo compounds or peroxy compounds in an alkaline medium.
    Type: Grant
    Filed: January 26, 1976
    Date of Patent: August 8, 1978
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernhard Schulz, Joachim Paust, Joachim Schneider
  • Patent number: 4100180
    Abstract: A solid catalyst for preparation of unsaturated alcohols by selective hydrogenation of the aldehyde group of unsaturated aldehydes, said catalyst comprising platinum oxide and deposited on its surface in an atmosphere of hydrogen, an iron compound and a zinc compound, and an improved process for preparing unsaturated alcohols by catalytic hydrogenation of unsaturated aldehydes with hydrogen in the presence of the aforesaid catalyst.
    Type: Grant
    Filed: December 23, 1975
    Date of Patent: July 11, 1978
    Assignee: Teijin, Limited
    Inventors: Yataro Ichikawa, Nobuo Suzuki, Toru Sawaki
  • Patent number: 4098827
    Abstract: A total synthesis of canthaxanthin, a known food coloring agent from alpha or retro ionone.
    Type: Grant
    Filed: January 17, 1977
    Date of Patent: July 4, 1978
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Michael Rosenberger
  • Patent number: 4095038
    Abstract: A process for fermentatively hydrogenating and reducing ketoisophorone to produce optically active [4R,6R]-4-hydroxy-2,6,6-trimethyl-cyclohexanone useful as an intermediate in the production of optically active carotenoids and intermediates in the production of these carotenoids.
    Type: Grant
    Filed: July 20, 1976
    Date of Patent: June 13, 1978
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Walter Boguth, Hans Georg Wilhelm Leuenberger, Hans Johann Mayer, Erich Widmer, Reinhard Zell
  • Patent number: 4092366
    Abstract: A synthesis of novel Vitamin A intermediates from betaionone 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: May 30, 1978
    Assignee: SCM Corporation
    Inventor: William Oroshnik
  • Patent number: RE30260
    Abstract: A total synthesis of canthaxanthin, a known food coloring agent from alpha or retro ionone.
    Type: Grant
    Filed: March 2, 1979
    Date of Patent: April 22, 1980
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Michael Rosenberger