Aromatic Patents (Class 435/156)
  • Patent number: 4970163
    Abstract: Described is a microbilogical method for producing the lactone, sclareolide and a diol having the chemical structure: ##STR1## using sclareol having the structure: ##STR2## as a substrate and using one of the microorganisms: Cryptococcus albidus (saito [skinner var. albidus]), ATCC 20918Bensingtonia ciliata, ATCC 20919Cryptococcus laurentii, ATCC 20920Cryptococcus albidus, ATCC 20921.
    Type: Grant
    Filed: August 28, 1989
    Date of Patent: November 13, 1990
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Mohamad I. Farbood, James A. Morris, Arthur E. Downey
  • Patent number: 4962031
    Abstract: The present invention provides a process for producing optically active compounds by a biochemical method in which specific compounds having hydroxyl groups are reacted with esters in the presence of hydrolases. The compounds have the following general formula: ##STR1## wherein X is selected from halogen atoms and a cyano group. Y is selected from the group constituting substituted phenyl groups, halogen atoms, cyano, trifluoromethyl and amino groups and alkylamino and alkyloxycarbonyl groups in which alkyl groups have 1-20 carbon atoms. R is an alkylene group having 1-20 carbon atoms and n is 0 or 1.
    Type: Grant
    Filed: May 2, 1988
    Date of Patent: October 9, 1990
    Assignee: Chisso Corporation
    Inventors: Naoyuki Yoshida, Masakazu Kaneoya, Manabu Uchida, Hiroshi Morita
  • Patent number: 4948732
    Abstract: There is disclosed a novel microorganism Aspergillus niveus, ATCC 20922, and a process for chiral reduction of ketones using said microorganisms.
    Type: Grant
    Filed: September 26, 1989
    Date of Patent: August 14, 1990
    Assignee: Schering Corporation
    Inventor: William Charney
  • Patent number: 4937192
    Abstract: A halogenation method using a haloperoxidase obtained from a fungus selected from the dematiaceous hyphomycetes. The enzyme has an optimum activity above about pH 5.0, and can oxidize chloride, bromide, or iodide ions.
    Type: Grant
    Filed: November 12, 1987
    Date of Patent: June 26, 1990
    Assignee: Cetus Corporation
    Inventors: Jennie C. Hunter, Angela Belt, Lynn S. Sotos, Michelle E. Fonda
  • Patent number: 4937191
    Abstract: A method producing a non-heme haloperoxidase which is substantially resistant to inactivation, at room temperature, in up to 0.3M H.sub.2 O.sub.2 for up to 25 hours, and up to 0.5mM HOCl for up to two minutes. One such haloperoxidase, isolated from Curvularia inaequalis, contains about 2 gram atoms of zinc per molecule. A halogenation reaction employing the enzyme can be performed at H.sub.2 O.sub.2 and hypohalous acid concentrations which produce rapid inactivation of heme-containing haloperoxidases.
    Type: Grant
    Filed: November 12, 1987
    Date of Patent: June 26, 1990
    Assignee: Cetus Corporation
    Inventors: John Geigert, Te-Ning E. Liu, Thabiso N'timkulu
  • Patent number: 4931399
    Abstract: The invention relates to a method for microbiologically resolving racemic 2,3-o-substituted glycerol esters to obtain optically activated 2,3-o-substituted glycerol with remaining esters also being optically active.
    Type: Grant
    Filed: September 9, 1985
    Date of Patent: June 5, 1990
    Assignee: The Wisconsin Alumni Research Foundation
    Inventor: Charles J. Sih
  • Patent number: 4927759
    Abstract: Strains of Pseudomonas putida selected from Pseudomonas putida NCIB 12190 and mutant strains thereof, which mutant strains can be obtained by chemical and physical mutation, allowing the mutated bacteria to grow prior to exposure to benzene or fluorobenzene, and subsequently, after further growth in the presence of benzene or fluorobenzene, selecting those mutant strains which accumulate cis-dihydroxycyclohexadiene or catechol or their fluorinated analogues. The new strains can be used in biochemical processes for the preparation of cis-dihydroxycyclohexadienes and catechols.
    Type: Grant
    Filed: June 8, 1989
    Date of Patent: May 22, 1990
    Assignee: Shell Oil Company
    Inventors: John A. Schofield, Peter R. Betteridge, George Ryback, Philip J. Geary
  • Patent number: 4921798
    Abstract: R- and S-1-Phenyl-1,3-propanediol, each of high optical purity, were prepared by a chemoenzymatic sequence starting with ethyl benzoylacetate. The first step was a catalytic hydrogenation of the .beta.-ketoester conducted at room temperature. The enzymatic hydrolysis of the resulting hydroxyester proceeded in a facile manner using a commercial preparation of the lipase from Pseudomonas fluorescens. The enzymatic hydrolysis proceeded at a moderate rate (350 mg lipase/0.10 mol of racemic ester required a 20-hour reaction time with an enantiomeric rate ratio (E value) of 36). The hydrolysis was run to 45-50% conversion to afford isolated S-3-phenyl-3-hydroxypropionic acid of 85-90% ee after separation from the residual ester (aqueous base extraction). The optical purity of the hydroxy acid was determined by conversion to the methyl ester (CH.sub.3 I, KHCO.sub.3, acetone), and derivatization with S-MTPA-Cl, and .sup.1 H NMR analysis.
    Type: Grant
    Filed: September 25, 1989
    Date of Patent: May 1, 1990
    Assignee: Eastman Kodak Company
    Inventor: Neil W. Boaz
  • Patent number: 4900671
    Abstract: A process for the preparation of a phenolic resin which comprises reacting a phenol with a peroxidase or an oxidase enzyme and a peroxide in an organic solvent containing medium to generate phenolic radicals which react to form a phenolic resin.
    Type: Grant
    Filed: July 8, 1987
    Date of Patent: February 13, 1990
    Assignee: The Mead Corporation
    Inventors: Alexander R. Pokora, William L. Cyrus, Jr.
  • Patent number: 4894337
    Abstract: A process for producing useful quantities of a cyclic hydroxide, such as pyrocatechol from a compound having a benzene ring, such as phenol using a Bacillus is described. The process uses tetracycline to inhibit the modification of the cyclic hydroxide by the Bacillus. Pyrocatechol and other related compounds are commercially useful chemicals.
    Type: Grant
    Filed: January 17, 1989
    Date of Patent: January 16, 1990
    Assignee: Board of Trustees operating Michigan State University
    Inventors: Patrick J. Oriel, Gopalakrishnan Gurujeyalakshmi
  • Patent number: 4894336
    Abstract: Process for the production of optically active (+)-bicyclo[3.3.0]octanol derivatives of formula (+)-I, in which R.sub.1 and R.sub.2 represent jointly an oxygen atom or the double-bond residue --O--X--O-- with X as a straight or branched-chain alkylene with 1-7 C-atoms, or R.sub.1 and R.sub.2 represent separately the residue OR.sub.5 with R.sub.5 as a straight or branched-chain alkyl with 1-7 C-atoms, and R.sub.3 the residue COOZ with Z as a hydrogen atom, straight or branched chain alkyl with 1-7 C atoms, cycloalkyl with 3-6 C atoms, phenyl or aralkyl with 7-10 atoms or R.sub.3 is the residue --(CH.sub.2).sub.n --O--COR.sub.4 with n having the meaning 1-4 and R.sub.4 as a straight or branched-chain alkyl with 1-7 C atoms, cycloalkyl with 3-6 C atoms, phenyl or aralkyl with 7-10 C atoms. The process is characterized in that racemic 3.alpha.-cyloxy-cis-bicyclo[3.3.0]-octane derivatives of formula (+)-II, wherein R.sub.1, R.sub.2 R.sub.3 and R.sub.
    Type: Grant
    Filed: July 13, 1988
    Date of Patent: January 16, 1990
    Assignee: Schering Aktiengesellschaft
    Inventors: Karl Petzoldt, Helmut Dahl, Werner Skuballa
  • Patent number: 4889804
    Abstract: Certain novel alkenyl-substituted dihydroxycyclohexadienes and the corresponding catechols are prepared by providing a culture of a microorganism selected from P.putida NCIB 12190 and mutants thereof, supplying to the culture the corresponding benzene derivatives in suitable fermentation medium, and subsequently recovering the desired dihydroxycyclohexadiene in cis-relationship, optionally followed by dehydrogenating the compound to afford the corresponding catechol.
    Type: Grant
    Filed: December 21, 1987
    Date of Patent: December 26, 1989
    Assignee: Shell Oil Company
    Inventor: John A. Schofield
  • Patent number: 4879233
    Abstract: There is disclosed a novel microorganism Aspergillus niveus, ATCC 20922, and a process for chiral reduction of ketones using said mircoorganisms.
    Type: Grant
    Filed: February 10, 1989
    Date of Patent: November 7, 1989
    Assignee: Schering Corporation
    Inventor: William Charney
  • Patent number: 4877732
    Abstract: Novel compound cis-1,2-dihydroxy-3-trifluoromethylcyclohexa-3,5-diene (and certain fluoro-substituted analogues) can be produced biochemically by culturing a wild type or mutant strain of P.putida with benzotrifluoride or certain fluoro-substituted analogues as substrate.
    Type: Grant
    Filed: July 2, 1987
    Date of Patent: October 31, 1989
    Assignee: Shell Oil Company
    Inventor: John A. Schofield
  • Patent number: 4876200
    Abstract: Strains of Pseudomonas putida selected from Pseudomonas putida NCIB 12190 and mutant strains thereof, which mutant strains can be obtained by chemical and physical mutation, allowing the mutated bacteria to grow prior to exposure to benzene or fluorobenzene, and subsequently, after further growth in the presence of benzene or fluorobenzene, selecting those mutant strains which accumulate cis-dihydroxycyclohexadiene or catechol or their fluorinated analogues. The new strains can be used in biochemical processes for the preparation of cis-dihydroxycyclohexadienes and catechols.
    Type: Grant
    Filed: July 1, 1987
    Date of Patent: October 24, 1989
    Assignee: Shell Oil Company
    Inventors: John A. Schofield, Peter R. Betteridge, George Ryback, Philip J. Geary
  • Patent number: 4874701
    Abstract: Novel microorganisms can be used to convert n-eugenol to coniferylaldehyde.
    Type: Grant
    Filed: February 9, 1987
    Date of Patent: October 17, 1989
    Assignee: BASF Aktiengesellschaft
    Inventor: Bryan Cooper
  • Patent number: 4857468
    Abstract: A process for preparing optically active 2-halo-1-phenyl ethanol having the general formula [I*]: ##STR1## wherein X is a halogen atom, by asymmetrically reducing 2-halo-acetophenone having the general formula [II]: ##STR2## wherein X is as above, to give optically active 2-halo-1-phenyl ethanol, (R)-form or (S)-form, employing the microorganism. ##STR3## According to the present invention, optically active 2-halo-1-phenyl ethanol can be prepared with a good optical purity and yield in a simple process.
    Type: Grant
    Filed: April 10, 1986
    Date of Patent: August 15, 1989
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hidetoshi Kutsuki, Ikuo Sawa, Natsuki Mori, Junzo Hasegawa, Kiyoshi Watanabe
  • Patent number: 4851344
    Abstract: Monocarboxylic and dicarboxylic acids of up to 10 carbon atoms, which may also contain double bonds and be substituted by halogen, phenyl or hydroxyl, are microbially reduced to the corresponding alcohols by performing the reduction with carbon monoxide and/or a formate in the presence of a mediator.
    Type: Grant
    Filed: January 26, 1988
    Date of Patent: July 25, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Simon, Herbert Lebertz
  • Patent number: 4837399
    Abstract: Three naphthoquinones isolated from cultures of Fusarium solani were found to be effective antibiotics against gram-positive bacteria. Controlling the dissolved oxygen concentration in the fermentation medium between 0.7 and 2.0 ppm resulted in maximum yields of the naphthoquinones. 2,3-Dihydro-5,8-dihydroxy-6-methoxy-2-hydroxymethyl-3-(2-hydroxypropyl)-1, 4- naphtholenedione was the most effective antibiotic.
    Type: Grant
    Filed: May 10, 1988
    Date of Patent: June 6, 1989
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: Robert A. Baker, James H. Tatum
  • Patent number: 4837150
    Abstract: A process in which a culture of a methane-oxidizing bacterium or an extract thereof containing a methane oxidizing system is used as oxidizing agent for the oxidation of a higher short-chain alkane, an alkene or a cyclic organic compound.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: June 6, 1989
    Assignee: National Research Development Corporation
    Inventors: Howard Dalton, John Colby, David I. Stirling
  • Patent number: 4798799
    Abstract: The invention provides a microbiological method for preparing diol and furan compounds from a variety of substrates using the microorganism Hyphozyma roseoniger, CBS 214.83 and ATCC 20624.
    Type: Grant
    Filed: August 29, 1986
    Date of Patent: January 17, 1989
    Assignee: Fritzsche Dodge & Olcott Inc.
    Inventors: Mohamad I. Farbood, Brian J. Willis
  • Patent number: 4765901
    Abstract: A process for treating waste water containing both phenolic compounds being toxic for methanogenic organisms and degradable non-phenolic compounds prior to its anaerobic purification as well as a process for detoxifying waste water containing phenolic compounds being toxic for aquatic organisms by subjecting said waste water to an oxidative treatment in such a way that no or virtually no precipitation is formed of the polyphenol compounds produced and virtually no influence is executed on the biochemical oxygen demand and the chemical oxygen demand of the waste water.
    Type: Grant
    Filed: March 16, 1987
    Date of Patent: August 23, 1988
    Assignee: Pacques B.V.
    Inventor: James A. Field
  • Patent number: 4707447
    Abstract: A halogenation method using a haloperoxidase obtained from a fungus selected from the dematiaceous hyphomycetes. The enzyme has an optimum activity above about pH 5.0, and can oxidize chloride, bromide, or iodide ions.
    Type: Grant
    Filed: May 24, 1983
    Date of Patent: November 17, 1987
    Assignee: Cetus Corporation
    Inventors: Jennie C. Hunter, Angela Belt, Lynn S. Sotos, Michelle E. Fonda
  • Patent number: 4634668
    Abstract: The present invention provides a process for the production of p-cresol in a quantitative yield, which involves the acidification of an aqueous solution of 4-methylcyclohexa-3,5-diene-1,2-diol-1-carboxylic acid under ambient conditions of temperature and pressure to cause spontaneous decomposition of the starting material to p-cresol. The aqueous solution of 4-methylcyclohexa-3,5-diene-1,2-diol-1-carboxylic acid is produced by microbiological conversion of p-xylene with Pseudomonas putida Biotype A strain ATCC 39119.
    Type: Grant
    Filed: August 15, 1984
    Date of Patent: January 6, 1987
    Assignee: Celanese Corporation
    Inventor: Scott Hagedorn
  • Patent number: 4594324
    Abstract: A process in which a culture of a methane-oxidizing bacterium or an extract thereof containing a methane oxidizing system is used as oxidizing agent for the oxidation of a higher short-chain alkane, an alkene or a cyclic organic compound.
    Type: Grant
    Filed: December 28, 1982
    Date of Patent: June 10, 1986
    Assignee: National Research Development Corp.
    Inventors: Howard Dalton, John Colby, David I. Stirling
  • Patent number: 4587216
    Abstract: A purified hydroxylase enzyme component A of the methane monooxygenase enzyme isolated from the soluble fraction of Methylobacterium organophilum (CRL.26) (NRRL B-11,222) is found to contain three subunits. Any component A derived from methylotrophs having the particular characteristics of this isolated component A may be employed in conjunction with the flavoprotein component C of the methane monooxygenase enzyme, preferably the flavoportein component derived from the same organism, to catalyze the oxidation of various oxidizable organic substrates to their respective oxidation products. Preferably, the substrate is propylene.
    Type: Grant
    Filed: August 31, 1983
    Date of Patent: May 6, 1986
    Assignee: Exxon Research and Engineering Co.
    Inventors: Ramesh N. Patel, Leonard E. Mortenson
  • Patent number: 4542100
    Abstract: The present invention provides a process for the production of p-cresol in a quantitative yield, which involves the acidification of an aqueous solution of the starting material, 4-methylcyclohexa-3,5-diene-1,2-diol-1-carboxylic acid, under ambient conditions of temperature and pressure to cause spontaneous decomposition of the starting material to p-cresol. The starting material is produced with Pseudomonas putida Biotype A strain ATCC 39119.
    Type: Grant
    Filed: August 15, 1984
    Date of Patent: September 17, 1985
    Assignee: Celanese Corporation
    Inventor: Scott Hagedorn
  • Patent number: 4536474
    Abstract: An undifferentiated symbiotic combination of alga and fungus cells, obtained directly from a lichen explant, are cultured in a media under appropriate conditions to produce aromatic lichenous substances and these substances are recovered.
    Type: Grant
    Filed: September 30, 1982
    Date of Patent: August 20, 1985
    Assignee: Nippon Paint Co., Ltd.
    Inventors: Yoshikazu Yamamoto, Ryuzo Mizuguchi, Yasuyuki Yamada
  • Patent number: 4532209
    Abstract: The present invention provides a process for the production of p-cresol in a quantitative yield, which involves the acidification of an aqueous solution of 4-methylcyclohexa-3,5-diene-1,2-diol-1-carboxylic acid under ambient conditions of temperature and pressure to cause spontaneous decomposition of the starting material to p-cresol. The 4-methylcyclohexa-3,5-diene-1,2-diol-1-carboxylic acid is produced by the conversion of p-xylene with the microorganism, Pseudomonas putida Biotype A strain ATCC No. 39119.
    Type: Grant
    Filed: September 7, 1982
    Date of Patent: July 30, 1985
    Assignee: Celanese Corporation
    Inventor: Scott Hagedorn
  • Patent number: 4455373
    Abstract: Microbiological oxidations of organic compounds including C6 to C28 alkanes, C2 to C18 alkenes and cyclic compounds such as cyclohexane and benzene carried out using as catalysts methane-utilizing bacteria adapted to utilize methanol as a carbon source. The application also covers methane-utilizing bacteria adapted to utilize methanol as a carbon source and a method for producing such bacteria. In the method methane-utilizing bacteria are cultured in the presence of methanol vapor as principal carbon source for sufficient time to allow adaptation to occur.
    Type: Grant
    Filed: July 29, 1981
    Date of Patent: June 19, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventor: Irving J. Higgins
  • Patent number: 4431736
    Abstract: Microbiological oxidation of biphenyl to bis-hydroxylated biphenyl employing Thamnostylum piriforme.
    Type: Grant
    Filed: June 1, 1982
    Date of Patent: February 14, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: James A. Romesser
  • Patent number: 4426449
    Abstract: A method is described for the manufacture of vicinal dihalogenated products from alkenes and alkynes by enzymatic reaction. The respective alkene or alkyne is contacted with a reaction mixture consisting of halogenating enzyme, an oxidizing agent and a halide ion source.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: January 17, 1984
    Assignee: Cetus Corporation
    Inventors: John Geigert, Saul L. Neidleman
  • Patent number: 4323649
    Abstract: A process for the partial degradation of complex cyclicorganic compounds such as 1-phenylheptane and m-chlorotoluene using methane-utilizing microorganisms or enzyme extracts thereof containing the enzymes methane mono-oxygenase and/or a de-halogenase. The preferred microorganism is Methylosinus trichosporium strain OB3b (NCIB 11131).
    Type: Grant
    Filed: February 28, 1980
    Date of Patent: April 6, 1982
    Assignee: Imperial Chemical Industries Limited
    Inventor: Irving J. Higgins
  • Patent number: 4196266
    Abstract: The present invention relates to new compound nanaomycin A and derivatives thereof represented by general formula: ##STR1## in which (a) R is H and R' is OH (nanaomycin A),(b) R is H and R' is NH.sub.2 (nanaomycin C),(c) R is COCH.sub.3 and R' is CH (acetylnanaomycin A), and(d) R is H and R' is OCH.sub.3 (nanaomycin A methyl ester).Nanaomycin A is a new compound of quinone type and its acute toxicity (LD.sub.50, intra-penetrial injection) in mice is 28.2 mg/Kg. Nanaomycin A and derivatives thereof are active on Gram-positive bacteria, trichophyton and mycoplasma and are useful as a medicament for humans and animals. Nanaomycins A and C are produced by culturing a nanaomycin-producing strain belonging to the genus Streptomyces aerobically in a medium to accumulate nanaomycins A and C in the cultured broths. The derivatives acetylnanaomycin A and nanaomycin A methyl ester have similar properties to those of nanaomycin A.
    Type: Grant
    Filed: December 7, 1977
    Date of Patent: April 1, 1980
    Assignee: The Kitasato Institute (Kitasato Kenkyuosho)
    Inventors: Satoshi Omura, Haruo Tanaka, Juichi Awaya, Toju Hata
  • Patent number: 4194064
    Abstract: The present invention relates to new compound designated as nanaomycin B represented by general formula: ##STR1## Nanaomycin B is a quinone type and is active on mycoplasma, Gram-positive bacteria and trycophyton. This compound is useful as a medicament for infectious diseases of humans and animals caused by a parasite of trichophyton or mycoplasma etc. The acute toxicity (LD.sub.50, intra-penetrial injection) in mice of this compound is 169 mg/kg. Nanaomycin B is produced by fermentation in which a nanaomycin-producing strain belonging to the genus Streptomyces is cultured in a medium under aerobic conditions and the accumulated nanaomycin B in the cultured broths is recovered therefrom.
    Type: Grant
    Filed: December 7, 1977
    Date of Patent: March 18, 1980
    Assignee: The Kitasato Institute (Kitasato Kenkyusho)
    Inventors: Satoshi Omura, Haruo Tanaka, Juichi Awaya, Toju Hata