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
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
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.
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.
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
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
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.
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
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.
Abstract: A novel procedure for the preparation of carotenoids, particularly vitamin A, employing .pi.-allyl transition metal complexes. Novel carotenoid intermediates are also disclosed.
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
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
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.
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
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.