Patents Assigned to Bizen Chemical Co., Ltd.
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Patent number: 11230704Abstract: The present invention provides a lipoxygenase that enables the highly efficient formation of an oxide of a highly unsaturated fatty acid or an oxide of a highly unsaturated fatty acid derivative from a highly unsaturated fatty acid or a highly unsaturated fatty acid derivative. The present invention provides a lipoxygenase that enables the highly efficient formation of 8-hydroxyeicosatetraenoic acid from arachidonic acid, the highly efficient formation of 8-hydroxyeicosapentaenoic acid from eicosapentaenoic acid, and the highly efficient formation of 10-hydroxy docosahexaenoic acid from docosahexaenoic acid. Specifically, the present invention provides a polynucleotide that comprises the nucleic acid sequence represented by SEQ ID NO: 1 and 3, or a homolog thereof, and a polypeptide that comprises the amino acid sequence represented by SEQ ID NO: 2 and 4, or a homolog thereof.Type: GrantFiled: February 27, 2019Date of Patent: January 25, 2022Assignees: Bizen Chemical Co., Ltd., Iwate Prefectural GovernmentInventors: Hidetoshi Yamada, Sayaka Yuki, Akira Yano, Naomichi Bamba, Tadahiro Tsushima, Yoshihisa Misawa
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Patent number: 11198893Abstract: Provided is a method for producing an unsaturated fatty acid oxide (e.g. ?3 fatty acid oxide) that is new and has more beneficial features compared to conventional technologies. This method uses a lipoxygenase-containing composition (e.g. a lipoxygenase-containing composition derived from beans) as a lipoxygenase enzyme, and also uses a freezing method with organic solvent extraction. The present invention makes it possible to produce an unsaturated fatty acid oxide (e.g. ?3 fatty acid oxide) efficiently and at a low cost. The present invention also provides a pharmaceutical composition containing an ?3 fatty acid oxide isolated and purified by this method as an active ingredient.Type: GrantFiled: June 19, 2017Date of Patent: December 14, 2021Assignee: Bizen Chemical Co., Ltd.Inventors: Shiho Saito, Yoshihisa Misawa, Naomichi Baba, Hiroshi Tabata, Tadahiro Tsushima, Jun Fujii
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Patent number: 10252972Abstract: A method of chemically extending a carbon chain of an unsaturated fatty acid for conversion into a different unsaturated fatty acid has been reported. The present invention shortens reaction steps of conventional methods, and completes a carbon chain extending reaction in a shorter time. The present invention provides a method of extending a carbon chain of an unsaturated fatty acid by two carbons, comprising steps of four stages including a short-path conversion reaction of an unsaturated fatty chain obtained from an unsaturated fatty acid into a malonic ester derivative, and heating of the malonic ester derivative to reflux in a lower fatty acid solution. The method of the present invention can complete a carbon chain extending reaction in a shorter time.Type: GrantFiled: June 27, 2016Date of Patent: April 9, 2019Assignee: Bizen Chemical Co., Ltd.Inventors: Naomichi Bamba, Yoshihisa Misawa, Hiroshi Tabata, Yoshio Shimizu
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Patent number: 10240172Abstract: The present invention relates to the field of methods for purifying fatty acid ethyl esters. According to the present invention, a method for obtaining a ?3 fatty acid ethyl ester, such as EPA and DHA, each as a high purity product at a high yield is provided. In the method according to the present invention, a raw material fat including EPA and DHA is treated with a lipolytic enzyme and ethyl-esterification is performed as needed; the treated substance is fractionated into a glyceride fraction and a free fatty acid fraction; a fraction comprising more EPA ester and a fraction comprising DHA ester are obtained from the respective fractions; the fraction comprising more EPA ester is purified to prepare a high-purity EPA ester; and the fraction comprising more DHA ester is purified to prepare a high-purity DHA ester.Type: GrantFiled: August 18, 2014Date of Patent: March 26, 2019Assignee: Bizen Chemical Co., Ltd.Inventors: Yoshio Shimizu, Keisuke Uryu, Tetsuro Taira, Jun Fujii
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Patent number: 10196584Abstract: A production method of highly unsaturated fatty acids with a high purity/high yield that compensates for shortcomings of conventional techniques is provided. A purification method of highly unsaturated fatty acids and/or derivatives thereof comprising (a) contacting and stirring first raw materials comprising the substances with a first silver salt aqueous solution to collect a first oil layer and a first aqueous layer; (b) separating the first aqueous layer into a second silver salt aqueous solution and the substances; and (c) contacting and stirring the first oil layer with the second silver salt aqueous solution for separation into an oil layer and an aqueous layer to obtain a second aqueous layer comprising the substances.Type: GrantFiled: May 30, 2016Date of Patent: February 5, 2019Assignee: Bizen Chemical Co., Ltd.Inventors: Hiroshi Tabata, Tetsuro Taira, Jun Fujii, Yoshihisa Misawa, Yoshio Shimizu
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Patent number: 10189770Abstract: The present invention provides a method of producing/purifying highly unsaturated fatty acids and/or derivatives thereof while suppressing deterioration of a silver salt aqueous solution, in production/purification of highly unsaturated fatty acids and/or derivatives thereof using the aqueous solution of silver salt. The present invention also contacts or mixes a mixture having a peroxide value (POV) of 10 or smaller with an aqueous solution of silver salt, in a method of purifying highly unsaturated fatty acids and/or derivatives thereof from a mixture comprising highly unsaturated fatty acids and/or derivatives thereof.Type: GrantFiled: May 30, 2016Date of Patent: January 29, 2019Assignee: Bizen Chemical Co., Ltd.Inventors: Mitsumasa Mankura, Yoshihisa Misawa, Yoshio Shimizu
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Patent number: 10005712Abstract: The present invention relates to a method for the chemical conversion of an unsaturated fatty acid, particularly a carbon chain extension reaction. According to the present invention, a method for extending the length of a carbon chain in an unsaturated fatty acid by two carbon atoms is provided, said method comprising a step of heating a malonic acid ester derivative of an unsaturated fatty acid to reflux in a lower fatty acid solution in the presence of an antioxidative agent. It is preferred that the unsaturated fatty acid is an unsaturated fatty acid having 16 to 24 carbon atoms. It is preferred that the unsaturated fatty acid is selected from the group consisting of linoleic acid, linolenic acid, arachidonic acid, stearidonic acid, icosatetraenoic acid, icosapentaenoic acid, tetracosahexaenoic acid and docosahexaenoic acid. According to the method of the present invention, a carbon chain extension reaction can be completed within a shorter time.Type: GrantFiled: January 14, 2015Date of Patent: June 26, 2018Assignee: BIZEN CHEMICAL CO., LTD.Inventors: Yoshio Shimizu, Naomichi Bamba, Mitsumasa Mankura
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Publication number: 20170166512Abstract: The present invention relates to a method for the chemical conversion of an unsaturated fatty acid, particularly a carbon chain extension reaction. According to the present invention, a method for extending the length of a carbon chain in an unsaturated fatty acid by two carbon atoms is provided, said method comprising a step of heating a malonic acid ester derivative of an unsaturated fatty acid to reflux in a lower fatty acid solution in the presence of an antioxidative agent. It is preferred that the unsaturated fatty acid is an unsaturated fatty acid having 16 to 24 carbon atoms. It is preferred that the unsaturated fatty acid is selected from the group consisting of linoleic acid, linolenic acid, arachidonic acid, stearidonic acid, icosatetraenoic acid, icosapentaenoic acid, tetracosahexaenoic acid and docosahexaenoic acid. According to the method of the present invention, a carbon chain extension reaction can be completed within a shorter time.Type: ApplicationFiled: January 14, 2015Publication date: June 15, 2017Applicant: Bizen Chemical Co., Ltd.Inventors: Yoshio Shimizu, Naomichi Bamba, Mitsumasa Mankura
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Publication number: 20160208296Abstract: The present invention relates to the field of methods for purifying fatty acid ethyl esters. According to the present invention, a method for obtaining a ?3 fatty acid ethyl ester, such as EPA and DHA, each as a high purity product at a high yield is provided. In the method according to the present invention, a raw material fat including EPA and DHA is treated with a lipolytic enzyme and ethyl-esterification is performed as needed; the treated substance is fractionated into a glyceride fraction and a free fatty acid fraction; a fraction comprising more EPA ester and a fraction comprising DHA ester are obtained from the respective fractions; the fraction comprising more EPA ester is purified to prepare a high-purity EPA ester; and the fraction comprising more DHA ester is purified to prepare a high-purity DHA ester.Type: ApplicationFiled: August 18, 2014Publication date: July 21, 2016Applicant: Bizen Chemical Co., Ltd.Inventors: Yoshio SHIMIZU, Keisuke URYU, Tetsuro TAIRA, Jun FUJII
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Patent number: 8680305Abstract: A method of obtaining a polyunsaturated fatty acid derivative comprises contacting a mixture of fatty acid derivatives with a silver salt aqueous solution, and adjusting the free fatty acid content in the silver salt aqueous solution to 0.2 meq or less per gram of silver when repeatedly using the silver salt aqueous solution. A polyunsaturated fatty acid derivative having high purity and excellent quality can thus be economically obtained.Type: GrantFiled: September 2, 2009Date of Patent: March 25, 2014Assignees: Q.P. Corporation, Bizen Chemical Co., Ltd.Inventors: Hiroyuki Sakaguchi, Hideaki Kobayashi, Yoshihisa Misawa, Keisuke Uryu, Yoshio Shimizu
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Publication number: 20140005144Abstract: It is an object of the present invention to provide a leukotriene receptor antagonist that can be conveniently prepared from a natural source. The object has been achieved by finding that a marine product such as a squid phospholipid extract or an Akiami paste shrimp phospholipid extract contains the antagonists of BLT and CysLT1, which are leukotriene receptors. Therefore, the present invention provides a dietary composition and a pharmaceutical composition for inhibiting the activity of leukotriene receptors, containing a squid phospholipid extract or an Akiami paste shrimp phospholipid extract.Type: ApplicationFiled: August 28, 2013Publication date: January 2, 2014Applicant: BIZEN CHEMICAL CO., LTD.Inventors: Teruyuki Kanada, Toru Kuyama, Takahiko Hada, Takafumi Ishihara
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Publication number: 20130165514Abstract: The present invention provides an orally administered composition and a dietary composition, which have a serum lipid improving effect. The orally administered composition and dietary composition, having a serum lipid improving effect, according to the present invention camp rise 2.0% by weight or less of a DHA ethyl ester composition comprising 75% by weight or more of DHA ethyl ester. It is preferable to comprise 1.2% by weight or less of the DHA ethyl ester composition. It is preferable not to substantially comprise a DHA ethyl ester composition comprising 30% by weight or less of DHA ethyl ester.Type: ApplicationFiled: February 18, 2011Publication date: June 27, 2013Applicant: BIZEN CHEMICAL CO., LTD.Inventors: Kenji Fukunaga, Yoshio Shimizu, Mikiya Takamoto, Teruyuki Kanada
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Publication number: 20110224452Abstract: A method of obtaining a polyunsaturated fatty acid derivative comprises contacting a mixture of fatty acid derivatives with a silver salt aqueous solution, and adjusting the free fatty acid content in the silver salt aqueous solution to 0.2 meq or less per gram of silver when repeatedly using the silver salt aqueous solution. A polyunsaturated fatty acid derivative having high purity and excellent quality can thus be economically obtained.Type: ApplicationFiled: September 2, 2009Publication date: September 15, 2011Applicants: Q.P. CORPORATION, BIZEN CHEMICAL CO., LTD.Inventors: Hiroyuki Sakaguchi, Hideaki Kobayashi, Yoshihisa Misawa, Keisuke Uryu, Yoshio Shimizu
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Publication number: 20110065673Abstract: It is an object of the present invention to provide a leukotriene receptor antagonist that can be conveniently prepared from a natural source. The object has been achieved by finding that a marine product such as a squid phospholipid extract or an Akiami paste shrimp phospholipid extract contains the antagonists of BLT and CysLT1, which are leukotriene receptors. Therefore, the present invention provides a dietary composition and a pharmaceutical composition for inhibiting the activity of leukotriene receptors, containing a squid phospholipid extract or an Akiami paste shrimp phospholipid extract.Type: ApplicationFiled: May 8, 2008Publication date: March 17, 2011Applicant: BIZEN CHEMICAL CO., LTD.Inventors: Teruyuki Kanada, Toru Kuyama, Takahiko Hada, Takafumi Ishihara
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Publication number: 20080262217Abstract: A method of producing glycogen is provided. The method comprises the step of heat- and pressure-treating a sugar-containing material under acidic conditions. The sugar-containing material is a polysaccharide or an oligosaccharide. Alternatively, the sugar-containing material is a plant material selected from the group consisting of Panax notoginseng, Yun Nan San-chi powder (trademark), Panax ginseng, wheat flour, soybean, soy flour, shiitake, and coffee extract residue. Representatively, the glycogen includes a molecule having a molecular weight of 10,000 or less. The glycogen has a specific rotation of [?]D+197° and anomeric proton peaks at 5.37 ppm and 4.95 to 5.33 ppm in 1H NMR spectra.Type: ApplicationFiled: June 24, 2008Publication date: October 23, 2008Applicant: BIZEN CHEMICAL CO., LTD.Inventors: Kazuyoshi Matsunaga, Takafumi Ishihara
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Patent number: 7396543Abstract: A method of producing glycogen is provided. The method comprises the step of heat- and pressure-treating a sugar-containing material under acidic conditions. The sugar-containing material is a polysaccharide or an oligosaccharide. Alternatively, the sugar-containing material is a plant material selected from the group consisting of Panax notoginseng, Yun Nan San-chi powder (trademark), Panax ginseng, wheat flour, soybean, soy flour, shiitake, and coffee extract residue. Representatively, the glycogen includes a molecule having a molecular weight of 10,000 or less. The glycogen has a specific rotation of [?]D+197° and anomeric proton peaks at 5.37 ppm and 4.95 to 5.33 ppm in 1H NMR spectra.Type: GrantFiled: December 6, 2002Date of Patent: July 8, 2008Assignee: Bizen Chemical Co., Ltd.Inventors: Kazuyoshi Matsunaga, Takafumi Ishihara