Unsaturation In The Ring Patents (Class 568/377)
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Publication number: 20020055453Abstract: Lower alkyl- and lower alkylidene-substituted, saturated or unsaturated cyclohexadecanones are grand fragrances with muscone note with which perfumes with new odor notes can be prepared.Type: ApplicationFiled: August 2, 2001Publication date: May 9, 2002Inventors: Marcus Eh, Ingo Wohrle
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Publication number: 20020049317Abstract: The method of this invention prepares acylated cyclic compounds by contacting phenyl esters as acylating agents with cyclic compounds in the presence of a cyanide or fluoride catalyst.Type: ApplicationFiled: April 12, 2001Publication date: April 25, 2002Inventor: Paul Walter Wojtkowski
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Patent number: 6362254Abstract: An activated, substantially water soluble poly(ethylene glycol) is provided having of a linear or branched poly(ethylene glycol) backbone and at least one terminus linked to the backbone through a hydrolytically stable linkage, wherein the terminus is branched and has proximal reactive groups. The free reactive groups are capable of reacting with active moieties in a biologically active agent such as a protein or peptide thus forming conjugates between the activated poly(ethylene glycol) and the biologically active agent.Type: GrantFiled: March 11, 1999Date of Patent: March 26, 2002Assignee: Shearwater CorporationInventors: J. Milton Harris, Antoni Kozlowski
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Patent number: 6346551Abstract: An inhibitory or blocking agent of molecular generating and/or inducing functions according to the formula:Type: GrantFiled: March 7, 1997Date of Patent: February 12, 2002Inventors: Shozo Koyoma, Yoshihiro Yamaguchi
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Patent number: 6342644Abstract: Provided is a method for the production of 1-menthol, which comprises hydrogenation of piperitenone with a transition metal complex of a specified optically active phosphine to produce pulegone, hydrogenation of the obtained pulegone with a ruthenium-phosphine-amine complex in the presence of base to obtain pulegol, and further hydrogenation of the pulegol with a transition metal catalyst.Type: GrantFiled: May 7, 2001Date of Patent: January 29, 2002Assignee: Takasago International CorporationInventors: Noboru Sayo, Takaji Matsumoto
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Patent number: 6297404Abstract: The present invention relates to a process for preparing 3,5,5-trimethylcyclohex-2-ene-1,4-dione (oxoisophorone; OIP) by oxidation of 3,5,5-trimethylcyclohex-3-en-1-one (&bgr;-isophorone, &bgr;-IP) with molecular oxygen in the presence of a solvent, of a base and of a transition metal salen derivative as catalyst and of an additive.Type: GrantFiled: June 21, 2000Date of Patent: October 2, 2001Assignee: BASF AktiengesellschaftInventors: Martin Jochen Klatt, Thomas Müller, Bernhard Bockstiegel
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Publication number: 20010011115Abstract: An activated, substantially water soluble poly(ethylene glycol) is provided having of a linear or branched poly(ethylene glycol) backbone and at least one terminus linked to the backbone through a hydrolytically stable linkage, wherein the terminus is branched and has proximal reactive groups. The free reactive groups are capable of reacting with active moieties in a biologically active agent such as a protein or peptide thus forming conjugates between the activated poly(ethylene glycol) and the biologically active agent.Type: ApplicationFiled: March 11, 1999Publication date: August 2, 2001Inventors: J. MILTON HARRIS, ANTONI KOZLOWSKI
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Patent number: 6228893Abstract: Described is a cyclohexenone long-chain alcohol represented by the formula (1): wherein R1, R2 and R3 each independently represents a hydrogen atom or a methyl group and X represents a C10-18 alkylene or alkenylene group. The cyclohexanone long-chain alcohol according to the present invention has excellent neurite growth stimulating effects and is therefore useful as a preventive and/or therapeutic agent for Alzheimer's disease.Type: GrantFiled: February 14, 2000Date of Patent: May 8, 2001Assignee: Meiji Milk Products Co., Ltd.Inventors: Bang Luu, Gaby Schmitt, Florence Keyling, Celine Junges-Girlanda, Masashi Yamada, Yukie Suma
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Patent number: 6201155Abstract: A process for the manufacture of a symmetrical, terminally ring-substituted polyenes by reacting a polyene di(O,O-dialkyl acetal) with a cyclic dienol ether in the presence of a Lewis or Brönsted acid, hydrolyzing the condensation product resulting therefrom and cleaving off alcohol under basic or acidic conditions from the polyene derivative produced at this stage. The novel cyclic dienol ethers, as well as, novel intermediates resulting from the condensation and additional intermediates in this process form further aspects of the invention. The final products are primarily carotenoids, which find corresponding use, e.g., as colorings and pigments for foodstuffs, animal products, etc.Type: GrantFiled: August 3, 1999Date of Patent: March 13, 2001Assignee: Roche Vitamins Inc.Inventors: Bruno Burdet, August Rüttimann
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Patent number: 6198004Abstract: The invention relates to a process for converting alpha acid and isoalpha acids to tetrahydroisoalpha acid. The process comprises isomerizing an alpha acid to produce isoalpha acid and hydrogenating the isoalpha acid in the presence of a noble metal catalyst wherein, the noble metal catalyst is added incrementally or continuously throughout the hydrogenation step. The invention also relates to tetrahydroisoalpha acids made by the above process.Type: GrantFiled: June 10, 1999Date of Patent: March 6, 2001Assignee: Haas Hop Products, Inc.Inventors: John Paul Maye, Jianping Xu, George Gauthier, Scott W. Weis
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Patent number: 6184419Abstract: The present invention relates to new &agr;,&bgr;-unsaturated ketones of formula I. The new compounds exhibit an intense, very long lasting green galbanum-type odor with fruity undertones. Compositions containing these novel compounds are also provided.Type: GrantFiled: May 10, 2000Date of Patent: February 6, 2001Assignee: Givaudan Roure (International) SAInventors: Katja Berg-Schultz, Jerzy A. Bajgrowiecz
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Patent number: 6177400Abstract: The compounds according to the general formula in which formula the dotted lines indicate a single or a double bond, n and m are 0 or 1, R1 is hydrogen or an acyl group —C(O)R3, R3 being a linear or branched alkyl or alkylene group from C1 to C8, the oxygen atom being bound to the adjacent &agr;-carbon atom by a double bond in the case where n is 0 and by a single bond in the case where n is 1, R2 is hydrogen or a linear or branched alkyl, alkenyl or alkoxy group from C1 to C8, or R2 is an alkenoxy group which is linked to the group R1 to form a 1,3-dioxolane cycle having 5 to 7 ring members, are useful perfuming ingredients. The most preferred compounds according to the invention are those which have a damascone- or damascenone-like structure, with the methyl substituent being in 4-position of the ring instead of the 2-position, as is the case in damascones and damascenones.Type: GrantFiled: May 7, 1999Date of Patent: January 23, 2001Assignee: Firmenich SAInventors: Hubert Mimoun, Wolfgang Klaus Giersch
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Patent number: 6177474Abstract: Compounds useful as preventive and therapeutic agents for bone and cartilage diseases; and drug compositions containing the same. The compounds are polyhydroxyphenol derivatives of general formula (I) and quinione analogues derived therefrom (wherein R1 is alkyl, optionally substituted benzyl or optionally substituted aryl; R2 is hydrogen, alkyl, alkenyl or optionally substituted benzyl; R3 is hydrogen, alkyl, alkenyl, optionally substituted benzyl, hydroxyl, alkoxy, alkenyloxy or optionally substituted benzyloxy; R4 is hydrogen, alkyl, alkenyl, optionally substituted benzyl or hydroxyl; and R5 and R6 are each independently hydrogen, alkyl, alkenyl or optionally substituted benzyl). The polyhydroxyphenol derivatives and the quinone analogues exhibit a potent inhibitory activity against bone resorption and are useful as preventive and therapeutic agents for bone and cartilage diseases.Type: GrantFiled: December 10, 1998Date of Patent: January 23, 2001Assignee: Hoechst Marion RousselInventors: Kunikazu Sakai, Yusuke Satoh, Kazuyuki Doi, Kazuyuki Kitamura
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Patent number: 6166261Abstract: In the presence of a catalytic system comprising a cyclic base and a complex of a transition metal with an N,N'-disalicylidenediamine, ketoisophorone or a derivative thereof is produced by oxidizing .beta.-isophorone or a derivative thereof with molecular oxygen with controlling the water content of a reaction system to 1% by weight or less at the initial stage of the reaction. Moreover, the above catalytic system further comprises a basic nitrogen-containing compound. The complex may be an N,N'-disalicylidene C.sub.2-5 alkylenediamine complex with manganese, iron, cobalt, copper, or vanadium. The cyclic base may be an alicyclic or aromtaic compound having at least two nitrogen atoms. As the basic nitrogen-containing compound, a Schiff base such as an imino compound and an anil compound can be used. The proportion of the nitrogen-containing compound to the complex is about 0.1/1 to 20/1 (molar ratio).Type: GrantFiled: May 21, 1999Date of Patent: December 26, 2000Assignee: Daicel Chemical Industries, Ltd.Inventor: Ikuo Takahashi
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Patent number: 6150374Abstract: The invention relates to novel substituted cycloalkenes of the formula (I), ##STR1## to a plurality of processes for their preparation, and to novel intermediates and a plurality of processes for their preparation.Type: GrantFiled: September 29, 1997Date of Patent: November 21, 2000Assignee: Bayer AktiengesellschaftInventors: Herbert Gayer, Peter Gerdes, Ralf Tiemann, Stefan Dutzmann, Klaus Stenzel
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Patent number: 6111125Abstract: A process for preparing 4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketones of the general formula I, in particular of the (1R,4S)-4-hydroxy-1,2,2-trimethylcyclopentyl methyl ketone of the formula Ia ##STR1## which is required for preparing the red dye capsorubin which is in demand, starts from 2,2,6-trimethylcyclohexanones of the general formula II ##STR2## where R is hydrogen or a protective group, via the novel intermediates of the general formulae V and VI ##STR3## by diastereoselective epoxidation and reaction of the resulting 7-oxabicyclo[4.1.0]heptanes of the general formula VIII ##STR4## with Lewis acids and, where appropriate, removal of the protective group. Also claimed are the novel intermediates of the formula V and their (1S) and (1R) isomers and those of the formula VIII as well as their (1R,3S,6S), (1S,3S,6R) and (1R,3R,6S) isomers.Type: GrantFiled: March 3, 1995Date of Patent: August 29, 2000Assignee: BASF AktiengesellschaftInventors: Michael John, Udo Rheude, Joachim Paust, Joachim Meyer
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Patent number: 6025527Abstract: Described are trimethylcyclohexenylcyclopropyl ketones having the structure: ##STR1## wherein one of the dashed lines is a carbon--carbon double bond and the other of the dashed lines is a carbon--carbon single bond, uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles, and mixtures of same with 3-methyl-1-phenylpentanol-5 and/or butanoylcyclohexane derivatives and/or acetic or propionic acid esters of o-methylphenyl isopropanol.Type: GrantFiled: June 18, 1999Date of Patent: February 15, 2000Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Marie R. Hanna
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Patent number: 5969196Abstract: For the preparation of 3,5-dimethylphenol by catalytic demethylation of isophorone in the gas phase in the presence of a metal or a metal alloy as catalyst, an isophorone-containing process stream is guided through reaction zones that contain said catalyst, whereby the reactivity of the catalyst varies in the reaction zones and the process stream between these reaction zones is thermostated in zones that do nor contain any catalyst, whereby the residual isophorone is greatly reduced, and the yield of 3,5-dimethylphenol is increased.Type: GrantFiled: April 27, 1998Date of Patent: October 19, 1999Assignee: Rutgers VFT AGInventors: Wolfgang Bergins, Jorg Talbiersky
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Patent number: 5965777Abstract: A process for the removal of catalyst poisons from hops and hop extracts is disclosed. After processing the hops to extract the alpha or beta acids therein, the alpha or beta acids are treated with activated nickel catalyst. The activated nickel catalyst binds the catalyst poisons which are believed to be sulfur containing compounds. The activated nickel and catalyst poisons are separated from the alpha or beta acids, and the alpha or beta acids are then hydrogenated and isomerized into tetrahydroisoalpha acids.Type: GrantFiled: October 29, 1996Date of Patent: October 12, 1999Assignee: Cultor Food Service, Inc.Inventor: George Gauthier
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Patent number: 5919986Abstract: Compounds of formula I: ##STR1## wherein the dotted carbon-carbon bond in the D-ring is C--C or C.dbd.C; C(R,R) is CH.sub.2 or C.dbd.CH.sub.2,R.sup.1 is H, F or OH,R.sup.2 and R.sup.3 are each independently C.sub.1-4 -alkyl or CF.sub.3, or together with the carbon to which they are bound form C.sub.3-6 -cycloalkyl.are useful in the treatment of vitamin D dependent disorders, such as psoriasis, leukemia; acne and seborrhoic dermatitis; osteoporosis hyperparathyroidism accompanying renal failure; and multiple sclerosis.Type: GrantFiled: October 13, 1998Date of Patent: July 6, 1999Assignee: Hoffmann-la Roche Inc.Inventors: Pierre Barbier, Franz Bauer, Peter Mohr, Marc Muller, Wolfgang Pirson
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Patent number: 5917093Abstract: Unsaturated organic compounds, in particular .alpha.-acids and .beta.-acids, are purified prior to hydrogenation by mixing them with an adsorbent capable of adsorbing catalyst poisons, preferably activated carbon, and separating the adsorbent containing the catalyst poisons to recover the thus purified unsaturated organic compounds. A significant reduction in the use of hydrogenation catalyst is realized.Type: GrantFiled: November 13, 1997Date of Patent: June 29, 1999Assignee: Miller Brewing CompanyInventors: Patrick L. Ting, Jay R. Refling, Michael A. VanSanford, Henry Goldstein
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Patent number: 5892124Abstract: Improved process for implementing the Diels-Alder reaction that consists in using reagents in the presence of at least one liquid salt of general formula Q.sup.+ A.sup.-, in which Q.sup.+ represents a quaternary ammonium and/or phosphonium and A.sup.- represents an anion and optionally at least one Lewis acid. The anion is preferably selected from the group that is formed by tetrafluoroborate, hexafluorophosphate, hexafluoroantimonate, hexafluoroarsenate, perfluoroalkylsulfonate, fluorosulfonate or else dichlorocuprate, tetrachloroborate, tetrachloroaluminate, and trichlorozincate. At the end of the reaction, the organic phase is separated, and the polar phase is reused.Type: GrantFiled: December 29, 1997Date of Patent: April 6, 1999Assignee: Institut Fran.cedilla.ais du PetroleInventors: Helene Olivier, Andre Hirschauer
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Patent number: 5877354Abstract: The present invention is a process for the production of isophorone having improved color and color stability. Crude isophorone is selectively hydrogenated to remove color forming impurities. The product isophorone will have an APHA color of about 10 or less.Type: GrantFiled: December 3, 1997Date of Patent: March 2, 1999Assignee: Aristech Chemical CorporationInventors: Chandrashekhar P. Kelkar, Alain A. Schutz
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Patent number: 5874633Abstract: A concentrated single phase aqueous alkaline solution of tetrahydroiso-.alpha.-acids having greater than 10% to about 45% w/w tetrahydroiso-.alpha.-acids is disclosed. A method of hydrogenating and formulating a starting solution of iso-.alpha.-acids to obtain such concentrated solutions of tetrahydroiso-.alpha.-acids is also disclosed.Type: GrantFiled: October 30, 1996Date of Patent: February 23, 1999Assignee: Miller Brewing CompanyInventors: Patrick L. Ting, Henry Goldstein
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Patent number: 5750765Abstract: Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-substituted quinone methide compound.Type: GrantFiled: August 27, 1996Date of Patent: May 12, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Peter Nesvadba, Samuel Evans, Matthew E. Gande, Volker H. von Ahn, Roland A. E. Winter
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Patent number: 5731283Abstract: Described are 1(4'-methylpentyl)-4-substituted ethylcyclohexane derivatives defined according to the structure: ##STR1## wherein R.sub.3, R.sub.4, R.sub.5 and R.sub.6 are the same or different hydrogen or methyl; wherein the dashed line represents a carbon carbon single bond or a carbon carbon double bond; wherein the wavy line represents a carbon carbon single bond or a carbon carbon double bond; with the proviso that when the wavy line is a carbon carbon single bond then the dashed line is a carbon carbon single bond; wherein Y represents a moiety selected from the group consisting of: ##STR2## wherein H represents hydrogen, C.sub.1 -C.sub.4 lower alkyl or C.sub.1 -C.sub.2 acyl; and wherein R.sub.1 represents C.sub.1 -C.sub.4 lower alkyl with the additional proviso that when Y is the moiety: ##STR3## then the dashed line is a carbon carbon single bond, and uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, perfumed articles and colognes.Type: GrantFiled: January 28, 1997Date of Patent: March 24, 1998Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, James Joseph Koestler, Jan Van Elst
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Patent number: 5728891Abstract: A process for the preparation of 3,3,5-trimethylcyclohexanone by catalytic hydrogenation of isophorone, wherein the hydrogenation is carried out in a plurality of two or more series-connected loops, wherein each loop involves the use of one reactor, which comprises:(a) feeding isophorone and hydrogen to an upper part of a reactor to catalytically hydrogenate said isophorone to produce a hydrogenation product,(b) recycling a portion of said hydrogenation product back into said upper part of said reactor,(c) feeding the remainder of said hydrogenation product from said reactor to an upper part of a subsequent reactor wherein isophorone is catalytically hydrogenated to produce a subsequent hydrogenation product, and wherein a portion of said subsequent hydrogenation product has been recycled and is fed with said remainder of said hydrogenation product to said upper part of said subsequent reactor,(d) repeating step (c) until the subsequent reactor is the last reactor,(e) recovering the remainder of said subsequeType: GrantFiled: June 26, 1996Date of Patent: March 17, 1998Assignee: Huels AktiengesellschaftInventors: Wilfried Bueschken, Juergen Hummel
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Patent number: 5603866Abstract: A composition comprising A) an aqueous solution wherein the total content of 3-isothiazolinones is below 8 wt/%, and B) a stabilizing compound of the formula:[R.sub.x A--C.sub.6 H.sub.2 R.sup.1 R.sup.2 ].sub.y --Zwherein:R, R.sup.1 and R.sup.2 each independently represents hydrogen, a straight-chained or branched or cyclic alkyl radical, aralkyl or aryl;A is oxygen or nitrogen;Z represents AR.sub.x, R.sup.1, R.sup.2, alkoxy methylene, methylene or alkylidene;provided that when A is oxygen, x is 0 or 1 and when A is nitrogen, x is 1 or 2; and y is 1 or 2;exhibits improved stability.Type: GrantFiled: May 17, 1995Date of Patent: February 18, 1997Assignee: Bromine Compounds, Ltd.Inventors: Jeane Segall, Leonard M. Shorr
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Patent number: 5583262Abstract: The present invention is directed to solid salts of hop acids and to processes for their production. Preferred are solid sodium and potassium salts of isoalpha acids rho-isoalpha acids, tetrahydroisoalpha acids, hexahydroisoalpha acids and beta acids.Type: GrantFiled: November 10, 1994Date of Patent: December 10, 1996Inventors: John P. Maye, Scot W. Weis
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Patent number: 5583247Abstract: Ethylenically unsaturated monomers are protected from premature polymerization during manufacture and storage by the incorporation therein of an effective stabilizing amount of a 7-substituted quinone methide compound.Type: GrantFiled: April 14, 1995Date of Patent: December 10, 1996Assignee: Ciba-Geigy CorporationInventors: Peter Nesvadba, Samuel Evans, Matthew E. Gande, Volker H. von Ahn, Roland A. E. Winter
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Patent number: 5411728Abstract: Use of derivatives of 6,6-dimethyl-2-acylcyclohex-4-en-1,3-diones in the sun protection sector of the cosmetics industry and preparations containing these derivatives, novel derivative and process for the production thereof.Use of a 6,6-dimethyl-2-acylcyclohex-4-en-1,3-dione derivative of the formula (I) ##STR1## in which R.sub.1 is a C.sub.1 -C.sub.6 alkyl radical, R.sub.2 is a hydrogen atom or a C.sub.1 -C.sub.6 alkyl radical, R.sub.3 is a hydrogen atom, a hydroxy radical or a C.sub.1 -C.sub.6 alkoxy radical as a sunscreen, preparations containing this derivative, novel derivative and process for the production thereof.Type: GrantFiled: March 2, 1994Date of Patent: May 2, 1995Assignee: Robertet S.A.Inventors: Daniel Joulain, Philippe Racine
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Patent number: 5326748Abstract: The invention relates to compounds of formula ##STR1## having a double bond in one of the positions indicated by the dotted lines. Compounds (I) are useful as perfuming ingredients for the preparation of perfuming compositions and perfuming articles, to which they impart sandalwood-animal notes.Type: GrantFiled: May 10, 1993Date of Patent: July 5, 1994Assignee: Firmenich SAInventor: Christian Chapuis
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Patent number: 5262552Abstract: An optically active (S)- or (R)-pentane compound of the general formula (11): ##STR1## wherein R.sub.11, R.sub.12 and R.sub.13 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R.sub.14 represents a hydroxy, protected hydroxy or oxo group, if R.sub.14 is an oxo group, the ring denoting benzene in the above formula (11) is benzoquinone, R.sub.15 represents a hydrogen atom, hydroxy or acyloxy group, R.sub.16 represents a hydroxy or acyloxy group, and the chiral central carbon marked with a symbol * in said formula (11) alternatively has one of an R-configuration and an S-configuration, is disclosed. Further, intermediate products of the compound of the formula (11) are also disclosed. Still further, a process for manufacturing the above compounds is disclosed. The compound of the formula (11) is easily synthesized from an easily available optically active starting material.Type: GrantFiled: February 20, 1991Date of Patent: November 16, 1993Assignee: Asahi Denka Kogyo K.K.Inventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5229425Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing substantially all of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml. of said broth, containing not more than 0.06 ml of said oxidized limonene per ml. of said broth and incubated at 37.degree. C. in air for 60 minutes.Type: GrantFiled: May 29, 1992Date of Patent: July 20, 1993Assignee: Doyle E. ChastainInventors: Doyle E. Chastain, W. E. Sanders, Jr., Christine C. Sanders
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Patent number: 5210314Abstract: A process for preparing canthaxanthin (Ia) and astaxanthin (Ib) of the formula I ##STR1##where R is H (a) or OH (b), comprises reacting a tertiary alcohol of the formula II ##STR2##where R is H (a) or OH (b), with trifluoroacetic acid, reacting the resulting novel trifluoroacetate of the formula III ##STR3##with triphenylphosphine, and reacting the resulting novel triphenylphosphonium trifluoroacetate of the formula IV ##STR4##with 2,7-dimethyl-2,4,6-octatriene-1,8-dial under the conditions of a Wittig synthesis. The present invention also relates to the novel trifluoroacetates of the formula III and the corresponding triphenylphosphonium trifluoroacetates of the formula IV.Type: GrantFiled: April 29, 1991Date of Patent: May 11, 1993Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Joachim Paust, Werner Hoffmann
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Patent number: 5200227Abstract: New stable, concentrated aqueous solutions of tetrahydro iso-alpha acid (THIA) and hexahydro iso-alpha acid (HHIA) are disclosed. These solutions depend upon the presence of a second kind of iso-alpha acid to increase the solubility of both iso-alpha acids to a point outside of the ranges of their normal solubilities . . . in the case of THIA and HHIA, to a point above their solubility ranges and, in the case of unreduced iso-alpha acid (UIA) and dihydro iso-alpha acid (DHIA), to a point below their commercial prior-art solubility ranges. This "inversion" of solubility and stability behavior in water, which requires the presence of two different kinds of iso-alpha acids, is new to the art, and provides a novel approach for making commercially-desirable concentrates of THIA and HHIA available to the brewer.Type: GrantFiled: May 11, 1992Date of Patent: April 6, 1993Assignee: Kalamazoo Holdings, Inc.Inventors: James A. Guzinski, Larry J. Stegink
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Patent number: 5167955Abstract: The invention provides a new aggregation pheromone for the bark beetle Ips pini identified as lanierone. Lanierone is the compound 4,4,6-trimethyl-2-hydroxy-2,5-cyclohexadiene-1-one and can be used, for example, to attract or trap bark beetles for monitoring or controlling the reproduction of the bark beetles.Type: GrantFiled: May 17, 1991Date of Patent: December 1, 1992Assignee: The Research Foundation of State University of New YorkInventors: Stephen A. Teale, Francis X. Webster, Aijun Zhang
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Patent number: 5166449Abstract: A process for making hexahydrolupulone is described which involves the separation of beta acids from a hop extract, the removal of catalyst poisons from the beta acids, the hydrogenation of the beta acids to hexahydrolupulone, and the purification of the resulting hexahydrolupulone. Its use as an inhibitor of the growth of unwanted types of cells is described, as well as preferred forms for such use.Type: GrantFiled: June 5, 1991Date of Patent: November 24, 1992Assignee: Kalamazoo Holdings, Inc.Inventors: Paul H. Todd, Jr., James A. Guzinski
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Patent number: 5153229Abstract: A process for producing a stable, bactericidal and fungicidal composition which consists essentially of bubbling air or oxygen into limonene, to produce an oxidized limonene having a rapid bactericidal activity as evidenced by the capability of killing at least 99.99% of the bacteria in a suitable culture medium inoculated with 10.sup.6 colony forming units of Staphylococcus aureus ATCC 25923 per ml.Type: GrantFiled: June 1, 1990Date of Patent: October 6, 1992Assignee: Doyle E. ChastainInventors: Doyle E. Chastain, W. Eugene Sanders, Jr., Christine C. Sanders
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Patent number: 5131945Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.Type: GrantFiled: July 13, 1990Date of Patent: July 21, 1992Assignee: Shell Research LimitedInventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
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Patent number: 5118856Abstract: A process for the preparation of cyclohexanedione derivatives of the general formula I ##STR1## where R.sup.1 is C.sub.2 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.5 -C.sub.12 -cycloalkyl with 0-4 olefinically unsaturated bonds, C.sub.2 -C.sub.8 -alkylthioalkyl, C.sub.6 -C.sub.12 -bicycloalkyl with 0-3 olefinically unsaturated bonds, unsubstituted or substituted aryl or hetaryl, or a heterocyclic radical of 4 to 7 atoms of which not more than 3 may be hetero-atoms chosen from O, S and N, the radical being saturated or olefinically unsaturated, by reacting an .alpha.,.beta.-unsaturated ketone (II) with a dialkyl malonate in the presence of a base to give the alkoxycarbonylcyclohexenolone or its salt (III) ##STR2## and acylation, hydrolysis and decarboxylation of (III), wherein the .alpha.,.beta.Type: GrantFiled: August 2, 1990Date of Patent: June 2, 1992Assignee: BASF AktiengesellschaftInventors: Gernot Reissenweber, Winfried Richarz
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Patent number: 5118865Abstract: Novel compounds of formula ##STR1## wherein the dotted lines indicate the location of a single or double bond, symbol R.sup.1 stands for a hydrogen atom or a methyl radical, symbol R.sup.2 represents a linear or branched, saturated or unsaturated, C.sub.1 to C.sub.4 alkyl radical, provided that R.sup.1 is not hydrogen when R.sup.2 represents a methyl or n-propyl radical and the ring is saturated. Compounds (Ia) are useful as perfuming ingredients.A process for their preparation is disclosed.Type: GrantFiled: March 11, 1991Date of Patent: June 2, 1992Assignee: Firmenich SAInventors: Christian Chapuis, Karl-Heinrich Schulte-Elte, Herve Pamingle, Christian Margot
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Patent number: 5041300Abstract: Two-phase and salt-containing intermediate products and the final purified hop flavor which is essentially free of impurities and which purified isoalpha acid or isohumulone will therefore not produce fruity, estery, sour aromas when used to flavor beverages, e.g., beer or ale, are disclosed. A rapid test for the detection of such aromas, involving dissolution of the hop flavor in ethanol at a concentration of one-half percent w/v and allowing the solution to stand for four days, allows accelerated determination of the presence or absence of such aromas and the odor-forming impurities which cause the undesirable odors.Type: GrantFiled: April 30, 1990Date of Patent: August 20, 1991Assignee: Kalamazoo Holdings, Inc.Inventors: Paul H. Todd, Jr., James A. Guzinski
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Patent number: 5039659Abstract: Described are 2,2,3-trimethylcyclopentenyl acetone derivatives defined according to one or a mixture of compounds having the structures: ##STR1## organoleptic uses thereof, processes for preparing same using as a starting material the compound having the structure: ##STR2## which is reacted to form the compound having the structure: ##STR3## which is further reacted to form the novel intermediate: ##STR4## which is then converted to the 2,2,3-trimethylcyclopentenyl acetone derivatives or our invention using the allylic alcohol having the structure: ##STR5## wherein R.sub.3, R.sub.4, and R.sub.5 are the same or different hydrogen or methyl; R.sub.6 represents hydrogen, methyl, ethyl, or propyl or isopropyl; x is 0, 1 or 2; R.sub.7 is methyl or ethyl; R.sub.7 ' and R.sub.7 " represent methyl or ethyl or R.sub.7 ', (CH.sub.2).sub.x and R.sub.7 " taken together represents C.sub.2 -C.sub.6 alkylene; M represents Li, Mg, X or MgX; and X represents chloro or bromo.Type: GrantFiled: August 7, 1990Date of Patent: August 13, 1991Assignee: International Flavors & Fragrances Inc.Inventors: Anubhav P. S. Narula, John J. De Virgilio, Vincent F. Kuczinski, Anton V. Ouwerkerk, Charles E. J. Beck, Kathleen E. Boardwick, Marie R. Hanna
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Patent number: 5015491Abstract: A method for the production of an isomerized hop preparation comprises mixing together hop extract with a solid alkaline or alkaline earth metal salt, and subjecting the resulting mixture to a temperature of at least 80.degree. C. for a time sufficient to effect conversion of .alpha.-acid to iso-.alpha.-acid. The method may be a stage in a process for brewing beer or the isomerized hop preparation may be further processed to produce high purity isomerized extracts.Type: GrantFiled: September 12, 1989Date of Patent: May 14, 1991Assignee: The Brewing Research FoundationInventors: Keith T. Westwood, Allan Crescenzi
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Patent number: 5013571Abstract: A method of converting alpha acids to hop flavors by exposing the alpha acids to an environment capable of substantially simultaneously isomerizing and reducing the alpha acids to form either THIAA or HHIAA. Another aspect of this invention is directed to a method of reducing hop flavors by exposing an isoalpha acid, a dihydroisoalpha acid or a mixture thereof to conditions suitable to reduce said acids to produce THIAA, HHIAA or a mixture thereof at a pH of about 5 to about 12 in a reaction inert, protic solvent. Yet another aspect of this invention is directed to a method of reducing hop flavors comprising exposing an isoalpha acid, a dihydroisoalpha acid or a mixture thereof to conditions suitable to reduce said acids to produce THIAA, HHIAA or a mixture thereof in a reaction inert, aprotic solvent.Type: GrantFiled: January 31, 1990Date of Patent: May 7, 1991Assignee: Pfizer Inc.Inventor: Bruce A. Hay
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Patent number: 5008425Abstract: A process which comprises reacting under substantially anhydrous conditions a perfluoroalkyltrihydrocarbylsilane and a carbonyl compound in the presence of a catalyst such that the carbonyl compound is perfluoroalkylated.Type: GrantFiled: April 12, 1989Date of Patent: April 16, 1991Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4960946Abstract: The present invention relates to novel substituted cyclohexanol compounds possessing a sandalwood aroma which are useful as fragrance materials. The invention also provides methods for synthesis thereof through a novel aldehyde intermediate. The compounds of the invention have the formula: ##STR1## wherein A is ##STR2## and wherein R.sub.1 is methyl or ethyl, R.sub.2 -R.sub.7 are independently hydrogen or methyl with the proviso that a maximum of two of the substituents R.sub.2 -R.sub.7 are methyl, and R.sub.8 is hydrogen, lower alkyl (C.sub.1 to C.sub.5) or acyl. The invention also provides fragrance compositions which utilize the compounds of the invention to impart a sandalwood aroma to perfume compositions, colognes and perfumed articles.Type: GrantFiled: October 13, 1989Date of Patent: October 2, 1990Assignee: BASF K&FInventors: Robert Eilerman, Philip Christenson, John Yurecko, Jr., Thomas Zebovitz
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Patent number: 4956195Abstract: A novel product utilizing a method for the removal hitherto unrecognized undesirable odor-forming impurities from hop flavors, including unreduced alpha and isoalpha acids and reduced alpha and isoalpha acids. By extracting the impurities from these flavors into water at a pH above 4, preferably above 6 or 7, with or without the presence of salt or solvent, and separating the aqueous phase containing the impurities from the purified hop flavor, as well as the important two-phase and salt-containing intermediate products and the final purified hop flavor which is essentially free of such impurities and which purified isoalpha acid or isohumulone will therfore not produce fruity, estery, sour aromas when used to flavor beverages, e.g., beer or ale, is achieved.Type: GrantFiled: May 19, 1988Date of Patent: September 11, 1990Assignee: Kalamazoo Holdings, Inc.Inventors: Paul H. Todd, Jr., James A. Luziski
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Patent number: 4936906Abstract: Agents for regulating plant growth containing an effective amount of at least one cyclohexanone derivative of the formula I ##STR1## where A, X, n, Y, Z and R have the meanings given in the disclosure, or salts of these compounds, and a process for regulating plant growth.Type: GrantFiled: July 2, 1986Date of Patent: June 26, 1990Assignee: BASF AktiengesellschaftInventors: Dieter Jahn, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Rainer Becker, Johann Jung, Wilhelm Rademacher