Unsaturation In The Ring Patents (Class 568/377)
  • Publication number: 20020055453
    Abstract: 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: Application
    Filed: August 2, 2001
    Publication date: May 9, 2002
    Inventors: Marcus Eh, Ingo Wohrle
  • Publication number: 20020049317
    Abstract: 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: Application
    Filed: April 12, 2001
    Publication date: April 25, 2002
    Inventor: Paul Walter Wojtkowski
  • Patent number: 6362254
    Abstract: 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: Grant
    Filed: March 11, 1999
    Date of Patent: March 26, 2002
    Assignee: Shearwater Corporation
    Inventors: J. Milton Harris, Antoni Kozlowski
  • Patent number: 6346551
    Abstract: An inhibitory or blocking agent of molecular generating and/or inducing functions according to the formula:
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: February 12, 2002
    Inventors: Shozo Koyoma, Yoshihiro Yamaguchi
  • Patent number: 6342644
    Abstract: 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: Grant
    Filed: May 7, 2001
    Date of Patent: January 29, 2002
    Assignee: Takasago International Corporation
    Inventors: Noboru Sayo, Takaji Matsumoto
  • Patent number: 6297404
    Abstract: 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: Grant
    Filed: June 21, 2000
    Date of Patent: October 2, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Jochen Klatt, Thomas Müller, Bernhard Bockstiegel
  • Publication number: 20010011115
    Abstract: 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: Application
    Filed: March 11, 1999
    Publication date: August 2, 2001
    Inventors: J. MILTON HARRIS, ANTONI KOZLOWSKI
  • Patent number: 6228893
    Abstract: 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: Grant
    Filed: February 14, 2000
    Date of Patent: May 8, 2001
    Assignee: Meiji Milk Products Co., Ltd.
    Inventors: Bang Luu, Gaby Schmitt, Florence Keyling, Celine Junges-Girlanda, Masashi Yamada, Yukie Suma
  • Patent number: 6201155
    Abstract: 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: Grant
    Filed: August 3, 1999
    Date of Patent: March 13, 2001
    Assignee: Roche Vitamins Inc.
    Inventors: Bruno Burdet, August Rüttimann
  • Patent number: 6198004
    Abstract: 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: Grant
    Filed: June 10, 1999
    Date of Patent: March 6, 2001
    Assignee: Haas Hop Products, Inc.
    Inventors: John Paul Maye, Jianping Xu, George Gauthier, Scott W. Weis
  • Patent number: 6184419
    Abstract: 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: Grant
    Filed: May 10, 2000
    Date of Patent: February 6, 2001
    Assignee: Givaudan Roure (International) SA
    Inventors: Katja Berg-Schultz, Jerzy A. Bajgrowiecz
  • Patent number: 6177400
    Abstract: 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: Grant
    Filed: May 7, 1999
    Date of Patent: January 23, 2001
    Assignee: Firmenich SA
    Inventors: Hubert Mimoun, Wolfgang Klaus Giersch
  • Patent number: 6177474
    Abstract: 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: Grant
    Filed: December 10, 1998
    Date of Patent: January 23, 2001
    Assignee: Hoechst Marion Roussel
    Inventors: Kunikazu Sakai, Yusuke Satoh, Kazuyuki Doi, Kazuyuki Kitamura
  • Patent number: 6166261
    Abstract: 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: Grant
    Filed: May 21, 1999
    Date of Patent: December 26, 2000
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Ikuo Takahashi
  • Patent number: 6150374
    Abstract: 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: Grant
    Filed: September 29, 1997
    Date of Patent: November 21, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Herbert Gayer, Peter Gerdes, Ralf Tiemann, Stefan Dutzmann, Klaus Stenzel
  • Patent number: 6111125
    Abstract: 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: Grant
    Filed: March 3, 1995
    Date of Patent: August 29, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael John, Udo Rheude, Joachim Paust, Joachim Meyer
  • Patent number: 6025527
    Abstract: 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: Grant
    Filed: June 18, 1999
    Date of Patent: February 15, 2000
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Richard M. Boden, Marie R. Hanna
  • Patent number: 5969196
    Abstract: 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: Grant
    Filed: April 27, 1998
    Date of Patent: October 19, 1999
    Assignee: Rutgers VFT AG
    Inventors: Wolfgang Bergins, Jorg Talbiersky
  • Patent number: 5965777
    Abstract: 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: Grant
    Filed: October 29, 1996
    Date of Patent: October 12, 1999
    Assignee: Cultor Food Service, Inc.
    Inventor: George Gauthier
  • Patent number: 5919986
    Abstract: 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: Grant
    Filed: October 13, 1998
    Date of Patent: July 6, 1999
    Assignee: Hoffmann-la Roche Inc.
    Inventors: Pierre Barbier, Franz Bauer, Peter Mohr, Marc Muller, Wolfgang Pirson
  • Patent number: 5917093
    Abstract: 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: Grant
    Filed: November 13, 1997
    Date of Patent: June 29, 1999
    Assignee: Miller Brewing Company
    Inventors: Patrick L. Ting, Jay R. Refling, Michael A. VanSanford, Henry Goldstein
  • Patent number: 5892124
    Abstract: 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: Grant
    Filed: December 29, 1997
    Date of Patent: April 6, 1999
    Assignee: Institut Fran.cedilla.ais du Petrole
    Inventors: Helene Olivier, Andre Hirschauer
  • Patent number: 5877354
    Abstract: 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: Grant
    Filed: December 3, 1997
    Date of Patent: March 2, 1999
    Assignee: Aristech Chemical Corporation
    Inventors: Chandrashekhar P. Kelkar, Alain A. Schutz
  • Patent number: 5874633
    Abstract: 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: Grant
    Filed: October 30, 1996
    Date of Patent: February 23, 1999
    Assignee: Miller Brewing Company
    Inventors: Patrick L. Ting, Henry Goldstein
  • Patent number: 5750765
    Abstract: 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: Grant
    Filed: August 27, 1996
    Date of Patent: May 12, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Peter Nesvadba, Samuel Evans, Matthew E. Gande, Volker H. von Ahn, Roland A. E. Winter
  • Patent number: 5731283
    Abstract: 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: Grant
    Filed: January 28, 1997
    Date of Patent: March 24, 1998
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Anubhav P. S. Narula, James Joseph Koestler, Jan Van Elst
  • Patent number: 5728891
    Abstract: 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 subseque
    Type: Grant
    Filed: June 26, 1996
    Date of Patent: March 17, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Wilfried Bueschken, Juergen Hummel
  • Patent number: 5603866
    Abstract: 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: Grant
    Filed: May 17, 1995
    Date of Patent: February 18, 1997
    Assignee: Bromine Compounds, Ltd.
    Inventors: Jeane Segall, Leonard M. Shorr
  • Patent number: 5583262
    Abstract: 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: Grant
    Filed: November 10, 1994
    Date of Patent: December 10, 1996
    Inventors: John P. Maye, Scot W. Weis
  • Patent number: 5583247
    Abstract: 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: Grant
    Filed: April 14, 1995
    Date of Patent: December 10, 1996
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Nesvadba, Samuel Evans, Matthew E. Gande, Volker H. von Ahn, Roland A. E. Winter
  • Patent number: 5411728
    Abstract: 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: Grant
    Filed: March 2, 1994
    Date of Patent: May 2, 1995
    Assignee: Robertet S.A.
    Inventors: Daniel Joulain, Philippe Racine
  • Patent number: 5326748
    Abstract: 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: Grant
    Filed: May 10, 1993
    Date of Patent: July 5, 1994
    Assignee: Firmenich SA
    Inventor: Christian Chapuis
  • Patent number: 5262552
    Abstract: 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: Grant
    Filed: February 20, 1991
    Date of Patent: November 16, 1993
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5229425
    Abstract: 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: Grant
    Filed: May 29, 1992
    Date of Patent: July 20, 1993
    Assignee: Doyle E. Chastain
    Inventors: Doyle E. Chastain, W. E. Sanders, Jr., Christine C. Sanders
  • Patent number: 5210314
    Abstract: 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: Grant
    Filed: April 29, 1991
    Date of Patent: May 11, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Hansgeorg Ernst, Joachim Paust, Werner Hoffmann
  • Patent number: 5200227
    Abstract: 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: Grant
    Filed: May 11, 1992
    Date of Patent: April 6, 1993
    Assignee: Kalamazoo Holdings, Inc.
    Inventors: James A. Guzinski, Larry J. Stegink
  • Patent number: 5167955
    Abstract: 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: Grant
    Filed: May 17, 1991
    Date of Patent: December 1, 1992
    Assignee: The Research Foundation of State University of New York
    Inventors: Stephen A. Teale, Francis X. Webster, Aijun Zhang
  • Patent number: 5166449
    Abstract: 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: Grant
    Filed: June 5, 1991
    Date of Patent: November 24, 1992
    Assignee: Kalamazoo Holdings, Inc.
    Inventors: Paul H. Todd, Jr., James A. Guzinski
  • Patent number: 5153229
    Abstract: 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: Grant
    Filed: June 1, 1990
    Date of Patent: October 6, 1992
    Assignee: Doyle E. Chastain
    Inventors: Doyle E. Chastain, W. Eugene Sanders, Jr., Christine C. Sanders
  • Patent number: 5131945
    Abstract: Compounds of formula I ##STR1## are useful as herbicides, effective against dicotyledonous weeds.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: July 21, 1992
    Assignee: Shell Research Limited
    Inventors: Hans-Joachim Bissinger, Ludwig Schoeder, Helmut Baltruschat, Manfred Garrecht, Erich Raddatz, Wolfgang Fruhstorfer
  • Patent number: 5118856
    Abstract: 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: Grant
    Filed: August 2, 1990
    Date of Patent: June 2, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gernot Reissenweber, Winfried Richarz
  • Patent number: 5118865
    Abstract: 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: Grant
    Filed: March 11, 1991
    Date of Patent: June 2, 1992
    Assignee: Firmenich SA
    Inventors: Christian Chapuis, Karl-Heinrich Schulte-Elte, Herve Pamingle, Christian Margot
  • Patent number: 5041300
    Abstract: 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: Grant
    Filed: April 30, 1990
    Date of Patent: August 20, 1991
    Assignee: Kalamazoo Holdings, Inc.
    Inventors: Paul H. Todd, Jr., James A. Guzinski
  • Patent number: 5039659
    Abstract: 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: Grant
    Filed: August 7, 1990
    Date of Patent: August 13, 1991
    Assignee: 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
  • Patent number: 5015491
    Abstract: 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: Grant
    Filed: September 12, 1989
    Date of Patent: May 14, 1991
    Assignee: The Brewing Research Foundation
    Inventors: Keith T. Westwood, Allan Crescenzi
  • Patent number: 5013571
    Abstract: 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: Grant
    Filed: January 31, 1990
    Date of Patent: May 7, 1991
    Assignee: Pfizer Inc.
    Inventor: Bruce A. Hay
  • Patent number: 5008425
    Abstract: 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: Grant
    Filed: April 12, 1989
    Date of Patent: April 16, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4960946
    Abstract: 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: Grant
    Filed: October 13, 1989
    Date of Patent: October 2, 1990
    Assignee: BASF K&F
    Inventors: Robert Eilerman, Philip Christenson, John Yurecko, Jr., Thomas Zebovitz
  • Patent number: 4956195
    Abstract: 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: Grant
    Filed: May 19, 1988
    Date of Patent: September 11, 1990
    Assignee: Kalamazoo Holdings, Inc.
    Inventors: Paul H. Todd, Jr., James A. Luziski
  • Patent number: 4936906
    Abstract: 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: Grant
    Filed: July 2, 1986
    Date of Patent: June 26, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Dieter Jahn, Michael Keil, Dieter Kolassa, Ulrich Schirmer, Rainer Becker, Johann Jung, Wilhelm Rademacher