Carbon To Carbon Unsaturation Containing Patents (Class 568/417)
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Patent number: 4560791Abstract: Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: ##STR2## (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: ##STR3## wherein R.sub.3 represents C.sub.1 -C.sub.Type: GrantFiled: November 14, 1983Date of Patent: December 24, 1985Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Gilbert Stork, Braja D. Mookherjee, Howard H. Heinsohn, Jr.
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Patent number: 4476147Abstract: A process for augmenting or enhancing the aroma or taste of alliaceous flavors, particularly garlic flavors, by augmenting or enhancing the garlic and green aroma and taste nuances of alliaceous-flavored foodstuffs comprising the step of adding to a alliaceous-flavored foodstuff an aroma or taste augmenting quantity of a mixture of cis and trans isomers of a compound having the structure: ##STR1## wherein the wavy lines indicate both cis and trans juxtaposition of the hydrogen and methallyl moieties about the carbon-carbon double bond.Type: GrantFiled: October 17, 1983Date of Patent: October 9, 1984Assignee: International Flavors & Fragrances Inc.Inventors: John B. Hall, James M. Sanders, James N. Siano
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Patent number: 4465863Abstract: Described are compounds defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 represent hydrogen or methyl with the provisos that:(i) the sum total of carbon atoms in R.sub.3, R.sub.4, R.sub.5, R.sub.6 and R.sub.7 is three;(ii) when R.sub.7 is methyl, then R.sub.5 and R.sub.6 are both methyl, and(iii) when either R.sub.3 or R.sub.4 is methyl, then R.sub.7 is hydrogenand wherein R.sub.8 represents hydrogen, acetyl, alkoxyacyl, hydroxyacyl, or alkali metal carboxylate; and R.sub.9 is hydrogen or allyl with the additional proviso that R.sub.8 and R.sub.9 are not both hydrogen.Also described is the use of the subgenus of such compounds defined according to the structure: ##STR2## in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles including solid or liquid nonionic, cationic, anionic or zwitterionic detergents, fabric softener compositions, fabric softener articles, cosmetic powders, hair preparations and the like.Type: GrantFiled: November 12, 1982Date of Patent: August 14, 1984Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Steven D. Temes, Theodore J. Tyszkiewicz, Marie R. Hanna
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Patent number: 4456558Abstract: This invention relates to novel polyprenyl ketone derivatives having the eral formula: ##STR1## in which n is an integer of 1-5, and R represents a hydroxymethyl, formyl or carboxyl group, and a process for the preparation of the same.Type: GrantFiled: October 16, 1981Date of Patent: June 26, 1984Assignees: Eisai Co., Ltd., General Director of the Agency of Industrial Science and TechnologyInventors: Akio Sato, Kenji Nakajima, Yoshimasa Takahara, Shizumasa Kijima, Isao Yamatsu, Kouichi Suzuki, Takeshi Suzuki, Toshihiko Nakamura
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Patent number: 4451392Abstract: Described is a process for preparing triconjugated dienones defined according to the structure: ##STR1## wherein R.sub.1 represents C.sub.1 -C.sub.8 alkyl, phenyl or phenyl methyl and wherein R.sub.2 represents hydrogen or C.sub.1 -C.sub.5 lower alkyl; and wherein the wavy lines are indicative of a "cis" or a "trans" juxtaposition of the R.sub.2, methyl, acyl or vinyl moieties about one or both of the carbon-carbon double bonds which process involves the reaction of an acyl halide having the structure: ##STR2## (wherein X represents chloro) with a substituted or unsubstituted prenyl ester having the structure: ##STR3## wherein R.sub.3 represents C.sub.1 -C.sub.Type: GrantFiled: September 30, 1982Date of Patent: May 29, 1984Assignee: International Flavors & Fragrances Inc.Inventors: William J. Evers, Gilbert Stork, Barja D. Mookherjee, Howard H. Heinsohn, Jr.
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Patent number: 4431844Abstract: An improved process for the preparation of unsaturated ketones of the general formula I ##STR1## where R.sup.1 is --CH.sub.3, ##STR2## and R.sup.2 and R.sup.3 are different and each is H or --CH.sub.3, by reacting an aldehyde of the general formula II ##STR3## with a molar excess of acetone or methyl ethyl ketone at an elevated temperature in the presence of an aqueous alkali metal hydroxide solution, wherein (a) all the reactants are mixed thoroughly, (b) the temperature is kept at from 10 to 120.degree. C. above the boiling point of the lowest-boiling component and (c) the pressure is kept at from p to 100 bar, where p is the vapor pressure of the mixture at the reaction temperature.The products methylpseudoionone, dimethylpseudoionone, pseudoirone, methylpseudoirone and dimethylpseudoirone are useful scents and scent intermediates. In addition, pseudoionone is an important intermediate for the industrial preparation of vitamin A, and 6-methyl-hepta-3,5-dien-2-one is a sought-after aromatic.Type: GrantFiled: March 24, 1982Date of Patent: February 14, 1984Assignee: BASF AktiengesellschaftInventors: Lothar Janitschke, Werner Hoffmann, Lothar Arnold, Manfred Stroezel, Hans-Juergen Scheiper
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Patent number: 4426321Abstract: This invention discloses a number of novel odorant alkadienyl ketones, alcohols and oximes having from 9 to 15 carbon atoms, processes for making same and odorant compositions containing same.Type: GrantFiled: July 24, 1981Date of Patent: January 17, 1984Assignee: Givaudan CorporationInventor: Paul A. Ochsner
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Patent number: 4412083Abstract: Described is a process for preparing solanone and norsolanadione using chemical intermediates defined according to the generic structure: ##STR1## wherein X is one of the moieties: ##STR2## wherein R represents hydrogen or methyl; wherein Y represents one of the structures: ##STR3## wherein one of the dashed lines represents a carbon-carbon single bond and the other of the dashed lines represents a carbon-carbon double bond; with the provisos that:(i) when Y is the moiety having the structure: ##STR4## then X is the moiety having the structure: ##STR5## (ii) when X is the moiety having the structure: ##STR6## then Y is the moiety having the structure:--C.tbd.N]In preparing solanone, the compound having the structure: ##STR7## or a mixture of compounds defined according to the structure: ##STR8## is reacted with methyl lithium and the resulting intermediate is hydrolyzed and the resulting compound is dehydrated.Type: GrantFiled: March 11, 1982Date of Patent: October 25, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Kenneth K. Light, William L. Schreiber, Joseph A. McGhie, Ronald P. Schreck, Takao Yoshida, Loren B. Schreiber, Ranya Muralidhara
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Patent number: 4385185Abstract: Compounds of the general formula I: ##STR1## wherein R.sub.1 and R.sub.2 are equal or different alkyl-, alkoxyalkyl-, or aryl groups, or together form a ring; R.sub.3 is an allyl or benzyl radical; and R.sub.4 and R.sub.5 represent hydrogen, alkyl, alkoxyalkyl, alkenyl or further compounds of the formula II: ##STR2## wherein R.sub.1, R.sub.2, R.sub.4 and R.sub.5 have the meaning indicated above and R.sub.6 stands for hydrogen or methyl or to compounds which are modified by the addition of hydrogen to at least one olefinic or carbonylic double bond of compounds of the general formula I or II. The invention also relates to a process for preparing the new compounds. The compounds of the general formula II are obtained by thermal treatment of a selection of compounds of formula I, for which R.sub.3 stands for the allyl or methallyl radical. The compounds according to the invention are used as fragrant and flavoring substances.Type: GrantFiled: March 20, 1981Date of Patent: May 24, 1983Assignee: Consortium fur Elektrochemische Industrie GmbHInventors: Helmut Gebauer, Walter Hafner
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Patent number: 4380674Abstract: Described are branched ketones defined according to the generic structure: ##STR1## wherein R.sub.4 ' represents C.sub.1 -C.sub.4 lower alkyl; wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents carbon-carbon single bonds. Also described are organoleptic uses of these branched ketones in augmenting or enhancing the aroma or taste of consumable materials such as perfume compositions, colognes, perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents; cosmetic powders; hair preparations; fabric softener compositions and dryer-added fabric softener articles), foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, smoking tobaccos and smoking tobacco articles as well as processes for preparing such branched ketones by reacting dimers of isoamylene with acyl halides or acyl anhydrides or mixed acyl anhydrides.Type: GrantFiled: November 5, 1981Date of Patent: April 19, 1983Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4374276Abstract: Described are acylated derivatives of triisobutylene defined according to the generic structures: ##STR1## wherein, in each of the molecules one of the dashed lines represents a carbon-carbon double bond and each of the other of the dashed lines represents a carbon-carbon single bond; and wherein, in each of the molecules R.sub.3 represents methyl or ethyl; uses thereof in augmenting or enhancing the aroma of perfume compositions, colognes and perfumed articles (e.g.Type: GrantFiled: August 27, 1981Date of Patent: February 15, 1983Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Theodore J. Tyszkiewicz
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Patent number: 4346237Abstract: Described are branched ketones defined according to the generic structure: ##STR1## wherein R.sub.4 ' represents C.sub.1 -C.sub.4 lower alkyl; wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents carbon-carbon single bonds. Also described are organoleptic uses of these branched ketones in augmenting or enhancing the aroma or taste of consumable materials such as perfume compositions, colognes, perfumed articles (e.g., solid or liquid anionic, cationic, nonionic or zwitterionic detergents; cosmetic powders; hair preparations; fabric softener compositions and dryer-added fabric softener articles), foodstuffs, chewing gums, toothpastes, medicinal products, chewing tobaccos, smoking tobaccos and smoking tobacco articles as well as processes for preparing such branched ketones by reacting dimers of isoamylene with acyl halides or acyl anhydrides or mixed acyl anhydrides.Type: GrantFiled: May 8, 1981Date of Patent: August 24, 1982Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4321255Abstract: Described is the use in augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes or chewing tobaccos comprising the step of adding to a foodstuff, toothpaste, chewing gum or chewing tobacco an aroma or taste augmenting or enhancing quantity of at least one acylated diisoamylene derivative defined according to the structure: ##STR1## wherein R.sub.4 ' represents C.sub.1 -C.sub.3 lower alkyl; wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represent carbon-carbon single bonds.Type: GrantFiled: September 4, 1980Date of Patent: March 23, 1982Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4315911Abstract: Described for augmenting or enhancing the aroma or taste of foodstuffs, chewing gums, toothpastes and medicinal products are certain branched ketones having the generic structure: ##STR1## wherein one of the dashed lines is a carbon-carbon double bond and the other of the dashed lines represents a carbon-carbon single bond.Type: GrantFiled: October 9, 1980Date of Patent: February 16, 1982Assignee: International Flavors & Fragrances Inc.Inventor: Richard M. Boden
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Patent number: 4294972Abstract: Compounds of the formula (I): ##STR1## wherein n is 3 to 5;Y is --CH.sub.2 --CH.sub.2, --CH.dbd.CH-- or C.tbd.C--;L is O or S;R.sub.1 is C.sub.1-4 alkyl;R.sub.2 is hydrogen, C.sub.1-4 alkyl or phenyl;R.sub.3 is hydroxy or protected hydroxy;R.sub.4 is hydrogen, C.sub.1-9 alkyl, C.sub.3-8 cycloalkyl, phenyl, naphthyl, any of which phenyl moieties or naphthyl moieties may be substituted by one or more halogen, trifluoromethyl, C.sub.1-6 alkyl, hydroxy, C.sub.1-6 alkoxy, phenyl C.sub.1-6 alkoxy or nitro groups; orR.sub.2 and R.sub.4 taken with the carbon atom to which they are joined represent a C.sub.5-8 cycloalkyl group; and R.sub.5 is C.sub.1-6 alkyl, having similar activity to natural prostaglandins, a process for their preparation, intermediates useful in that process and pharmaceutical compositions containing them.Type: GrantFiled: June 14, 1979Date of Patent: October 13, 1981Assignee: Beecham Group LimitedInventors: Frederick Cassidy, Alexander C. Goudie
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Patent number: 4292454Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.Type: GrantFiled: March 18, 1980Date of Patent: September 29, 1981Assignee: SCM CorporationInventors: Carlos G. Cardenas, Zia Ud Din
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Patent number: 4233453Abstract: This invention disclosed herein relates to pharmacologically active 15-deoxy-16-hydroxy prostaglandin derivatives of the E and F series wherein C.sub.16 is substituted with allenyl.These compounds are active as hypotensives, antisecretory, bronchodilating and fertility control agents.Type: GrantFiled: June 7, 1979Date of Patent: November 11, 1980Assignee: American Cyanamid CompanyInventor: Middleton B. Floyd, Jr.
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Patent number: 4228313Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.Type: GrantFiled: December 29, 1977Date of Patent: October 14, 1980Assignee: SCM CorporationInventors: Carlos G. Cardenas, Zia U. Din
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Patent number: 4226810Abstract: A chemical method for splitting the pyran ring of compounds such as 2,6,6-trimethyl-5,6-dihydro-4H-pyran is disclosed which consists in reacting the 4H-pyran derivatives concerned with water and a halogen-containing or halogen-donating catalyst at a comparatively low temperature, i.e. from 50.degree. C. to 130.degree. C. Interesting results are obtained and a selection field is afforded as regards the products of the pyran-ring cleavage.Type: GrantFiled: November 28, 1978Date of Patent: October 7, 1980Assignee: Anic, S.p.A.Inventors: Vincenzo Redaelli, Renato De Simone, Edoardo Platone
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Patent number: 4222963Abstract: Novel substituted propargyl alcohols of the formula: ##STR1## novel allylic alcohols of the formula: ##STR2## and; .delta.,.epsilon.-unsaturated ketones of the formula: ##STR3## are provided. In the above formulas, R represents a group of the formula: ##STR4## wherein X.sub.1 and X.sub.2 are both hydrogen atoms or wherein one of X.sub.1 and X.sub.2 is a hydrogen atom, the other jointly with Z represents a bond; Z jointly with X.sub.1 or X.sub.2 represents a bond or separately represent a hydrogen atom, a hydroxyl group or a lower alkoxy group; R.sub.1 and R.sub.2 are the same or different and represents hydrogen atoms or lower alkyl groups; n is 1 or 2; and when n is 2, X.sub.1, X.sub.2, X, R.sub.1 and R.sub.2 may be the same or different. These novel compounds are easily produced and are useful as perfumes and as interrelated intermediates for the production of terpenoid compounds.Type: GrantFiled: February 28, 1979Date of Patent: September 16, 1980Assignee: Kuraray Co., Ltd.Inventors: Yoshiji Fujita, Fumio Wada, Takashi Ohnishi, Takashi Nishida, Yoshiaki Omura, Fumio Mori, Takeo Hosogai, Sukeji Aihara
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Patent number: 4202822Abstract: Derivatives, analogs, and congeners of prostane having a 1-(hydroxymethyl)-1-oxo-prostane structure in the F.sub.1 series.Type: GrantFiled: December 8, 1977Date of Patent: May 13, 1980Assignee: American Cyanamid CompanyInventor: Allan Wissner