Aromatic Patents (Class 435/156)
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Patent number: 4970163Abstract: 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: GrantFiled: August 28, 1989Date of Patent: November 13, 1990Assignee: International Flavors & Fragrances Inc.Inventors: Mohamad I. Farbood, James A. Morris, Arthur E. Downey
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Patent number: 4962031Abstract: 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: GrantFiled: May 2, 1988Date of Patent: October 9, 1990Assignee: Chisso CorporationInventors: Naoyuki Yoshida, Masakazu Kaneoya, Manabu Uchida, Hiroshi Morita
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Patent number: 4948732Abstract: There is disclosed a novel microorganism Aspergillus niveus, ATCC 20922, and a process for chiral reduction of ketones using said microorganisms.Type: GrantFiled: September 26, 1989Date of Patent: August 14, 1990Assignee: Schering CorporationInventor: William Charney
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Patent number: 4937191Abstract: 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: GrantFiled: November 12, 1987Date of Patent: June 26, 1990Assignee: Cetus CorporationInventors: John Geigert, Te-Ning E. Liu, Thabiso N'timkulu
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Patent number: 4937192Abstract: 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: GrantFiled: November 12, 1987Date of Patent: June 26, 1990Assignee: Cetus CorporationInventors: Jennie C. Hunter, Angela Belt, Lynn S. Sotos, Michelle E. Fonda
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Patent number: 4931399Abstract: 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: GrantFiled: September 9, 1985Date of Patent: June 5, 1990Assignee: The Wisconsin Alumni Research FoundationInventor: Charles J. Sih
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Patent number: 4927759Abstract: 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: GrantFiled: June 8, 1989Date of Patent: May 22, 1990Assignee: Shell Oil CompanyInventors: John A. Schofield, Peter R. Betteridge, George Ryback, Philip J. Geary
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Patent number: 4921798Abstract: 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: GrantFiled: September 25, 1989Date of Patent: May 1, 1990Assignee: Eastman Kodak CompanyInventor: Neil W. Boaz
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Patent number: 4900671Abstract: 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: GrantFiled: July 8, 1987Date of Patent: February 13, 1990Assignee: The Mead CorporationInventors: Alexander R. Pokora, William L. Cyrus, Jr.
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Patent number: 4894336Abstract: 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: GrantFiled: July 13, 1988Date of Patent: January 16, 1990Assignee: Schering AktiengesellschaftInventors: Karl Petzoldt, Helmut Dahl, Werner Skuballa
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Patent number: 4894337Abstract: 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: GrantFiled: January 17, 1989Date of Patent: January 16, 1990Assignee: Board of Trustees operating Michigan State UniversityInventors: Patrick J. Oriel, Gopalakrishnan Gurujeyalakshmi
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Patent number: 4889804Abstract: 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: GrantFiled: December 21, 1987Date of Patent: December 26, 1989Assignee: Shell Oil CompanyInventor: John A. Schofield
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Patent number: 4879233Abstract: There is disclosed a novel microorganism Aspergillus niveus, ATCC 20922, and a process for chiral reduction of ketones using said mircoorganisms.Type: GrantFiled: February 10, 1989Date of Patent: November 7, 1989Assignee: Schering CorporationInventor: William Charney
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Patent number: 4877732Abstract: 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: GrantFiled: July 2, 1987Date of Patent: October 31, 1989Assignee: Shell Oil CompanyInventor: John A. Schofield
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Patent number: 4876200Abstract: 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: GrantFiled: July 1, 1987Date of Patent: October 24, 1989Assignee: Shell Oil CompanyInventors: John A. Schofield, Peter R. Betteridge, George Ryback, Philip J. Geary
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Patent number: 4874701Abstract: Novel microorganisms can be used to convert n-eugenol to coniferylaldehyde.Type: GrantFiled: February 9, 1987Date of Patent: October 17, 1989Assignee: BASF AktiengesellschaftInventor: Bryan Cooper
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Patent number: 4857468Abstract: 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: GrantFiled: April 10, 1986Date of Patent: August 15, 1989Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hidetoshi Kutsuki, Ikuo Sawa, Natsuki Mori, Junzo Hasegawa, Kiyoshi Watanabe
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Patent number: 4851344Abstract: 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: GrantFiled: January 26, 1988Date of Patent: July 25, 1989Assignee: BASF AktiengesellschaftInventors: Helmut Simon, Herbert Lebertz
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Patent number: 4837399Abstract: 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: GrantFiled: May 10, 1988Date of Patent: June 6, 1989Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Robert A. Baker, James H. Tatum
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Patent number: 4837150Abstract: 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: GrantFiled: December 9, 1985Date of Patent: June 6, 1989Assignee: National Research Development CorporationInventors: Howard Dalton, John Colby, David I. Stirling
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Patent number: 4798799Abstract: 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: GrantFiled: August 29, 1986Date of Patent: January 17, 1989Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Mohamad I. Farbood, Brian J. Willis
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Patent number: 4765901Abstract: 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: GrantFiled: March 16, 1987Date of Patent: August 23, 1988Assignee: Pacques B.V.Inventor: James A. Field
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Patent number: 4707447Abstract: 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: GrantFiled: May 24, 1983Date of Patent: November 17, 1987Assignee: Cetus CorporationInventors: Jennie C. Hunter, Angela Belt, Lynn S. Sotos, Michelle E. Fonda
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4-methylcyclohexa-3,5-diene-1,2-diol-1-carboxylic acid produced by Pseudomonas putida ATCC No. 39119
Patent number: 4634668Abstract: 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: GrantFiled: August 15, 1984Date of Patent: January 6, 1987Assignee: Celanese CorporationInventor: Scott Hagedorn -
Patent number: 4594324Abstract: 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: GrantFiled: December 28, 1982Date of Patent: June 10, 1986Assignee: National Research Development Corp.Inventors: Howard Dalton, John Colby, David I. Stirling
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Patent number: 4587216Abstract: 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: GrantFiled: August 31, 1983Date of Patent: May 6, 1986Assignee: Exxon Research and Engineering Co.Inventors: Ramesh N. Patel, Leonard E. Mortenson
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Strain of Pseudomonas putida for producing an intermediate compound in the production of para-cresol
Patent number: 4542100Abstract: 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: GrantFiled: August 15, 1984Date of Patent: September 17, 1985Assignee: Celanese CorporationInventor: Scott Hagedorn -
Patent number: 4536474Abstract: 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: GrantFiled: September 30, 1982Date of Patent: August 20, 1985Assignee: Nippon Paint Co., Ltd.Inventors: Yoshikazu Yamamoto, Ryuzo Mizuguchi, Yasuyuki Yamada
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Patent number: 4532209Abstract: 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: GrantFiled: September 7, 1982Date of Patent: July 30, 1985Assignee: Celanese CorporationInventor: Scott Hagedorn
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Patent number: 4455373Abstract: 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: GrantFiled: July 29, 1981Date of Patent: June 19, 1984Assignee: Imperial Chemical Industries PLCInventor: Irving J. Higgins
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Patent number: 4431736Abstract: Microbiological oxidation of biphenyl to bis-hydroxylated biphenyl employing Thamnostylum piriforme.Type: GrantFiled: June 1, 1982Date of Patent: February 14, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: James A. Romesser
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Patent number: 4426449Abstract: 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: GrantFiled: December 14, 1981Date of Patent: January 17, 1984Assignee: Cetus CorporationInventors: John Geigert, Saul L. Neidleman
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Patent number: 4323649Abstract: 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: GrantFiled: February 28, 1980Date of Patent: April 6, 1982Assignee: Imperial Chemical Industries LimitedInventor: Irving J. Higgins
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Patent number: 4196266Abstract: 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: GrantFiled: December 7, 1977Date of Patent: April 1, 1980Assignee: The Kitasato Institute (Kitasato Kenkyuosho)Inventors: Satoshi Omura, Haruo Tanaka, Juichi Awaya, Toju Hata
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Patent number: 4194064Abstract: 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: GrantFiled: December 7, 1977Date of Patent: March 18, 1980Assignee: The Kitasato Institute (Kitasato Kenkyusho)Inventors: Satoshi Omura, Haruo Tanaka, Juichi Awaya, Toju Hata