CA2795460A1 - Method for obtaining polyunsaturated fatty acid-containing compositions from microbial biomass - Google Patents
Method for obtaining polyunsaturated fatty acid-containing compositions from microbial biomass Download PDFInfo
- Publication number
- CA2795460A1 CA2795460A1 CA2795460A CA2795460A CA2795460A1 CA 2795460 A1 CA2795460 A1 CA 2795460A1 CA 2795460 A CA2795460 A CA 2795460A CA 2795460 A CA2795460 A CA 2795460A CA 2795460 A1 CA2795460 A1 CA 2795460A1
- Authority
- CA
- Canada
- Prior art keywords
- microbial biomass
- biomass
- acid
- oil
- extract
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
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- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
- C11B1/104—Production of fats or fatty oils from raw materials by extracting using super critical gases or vapours
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B7/00—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils
Landscapes
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Fats And Perfumes (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
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| PCT/US2011/033142 WO2011133610A1 (en) | 2010-04-22 | 2011-04-20 | Method for obtaining polyunsaturated fatty acid-containing compositions from microbial biomass |
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| EP2576801B1 (en) | 2010-06-01 | 2019-10-02 | DSM IP Assets B.V. | Extraction of lipid from cells and products therefrom |
| US20120213905A1 (en) * | 2010-08-11 | 2012-08-23 | E. I. Du Pont De Nemours And Company | Aquaculture feed compositions |
| JP6061866B2 (ja) | 2011-02-11 | 2017-01-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 微生物バイオマスから脂質含有組成物を得る方法 |
| JP2014510166A (ja) * | 2011-02-11 | 2014-04-24 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー | 短行程蒸留を使用する微生物源からのトリグリセリド油の精製 |
| CN105255738B (zh) * | 2011-07-21 | 2024-12-27 | 帝斯曼知识产权资产管理有限公司 | 生产二十碳五烯酸的微生物、脂肪酸组合物及其制作方法与用途 |
| SG11201403805WA (en) | 2012-01-06 | 2014-08-28 | Omthera Pharmaceuticals Inc | Dpa-enriched compositions of omega-3 polyunsaturated fatty acids in free acid form |
| AR095182A1 (es) | 2012-05-07 | 2015-09-30 | Omthera Pharmaceuticals Inc | Composiciones de estatinas y ácidos grasos omega-3 |
| FR2991337B1 (fr) * | 2012-05-29 | 2016-09-02 | Roquette Freres | Procede continu d'enrichissement en esters ethyliques de dha d'une huile produite par des microalgues |
| US10123986B2 (en) | 2012-12-24 | 2018-11-13 | Qualitas Health, Ltd. | Eicosapentaenoic acid (EPA) formulations |
| US9629820B2 (en) | 2012-12-24 | 2017-04-25 | Qualitas Health, Ltd. | Eicosapentaenoic acid (EPA) formulations |
| JP6824038B2 (ja) * | 2013-12-04 | 2021-02-03 | 日本水産株式会社 | ジホモ−γ−リノレン酸含有微生物油及びジホモ−γ−リノレン酸含有微生物菌体 |
| AU2014369042B2 (en) * | 2013-12-20 | 2020-04-30 | Dsm Ip Assets B.V. | Processes for obtaining microbial oil from microbial cells |
| BR112016014517B1 (pt) | 2013-12-20 | 2022-06-28 | Dsm Ip Assets B.V. | Processo para a obtenção de um óleo microbiano compreendendo um ou mais ácidos graxos poli-insaturados de uma ou mais células microbianas |
| JP2017500037A (ja) | 2013-12-20 | 2017-01-05 | ディーエスエム アイピー アセッツ ビー．ブイ． | 微生物細胞から微生物油を入手するための方法 |
| AR098893A1 (es) | 2013-12-20 | 2016-06-22 | Dsm Ip Assets Bv | Proceso para obtener aceite microbiano a partir de células microbianas |
| WO2015095696A1 (en) | 2013-12-20 | 2015-06-25 | Dsm Ip Assets B.V. | Processes for obtaining microbial oil from microbial cells |
| JP6998935B2 (ja) * | 2016-07-13 | 2022-01-18 | エボニック オペレーションズ ゲーエムベーハー | 溶解された脂質含有バイオマスから脂質を分離する方法 |
| EP3938480A4 (en) * | 2019-03-14 | 2022-12-28 | DSM IP Assets B.V. | Methods of obtaining lipids from a microbial cell composition by enzyme and ph shock |
| AU2022224053A1 (en) * | 2021-02-18 | 2023-09-14 | Cemvita Factory, Inc. | Systems and methods of making oil from microorganisms |
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| US4675132A (en) | 1985-03-28 | 1987-06-23 | The United States Of America As Represented By The Secretary Of Commerce | Polyunsaturated fatty acids from fish oils |
| US5169968A (en) * | 1985-09-10 | 1992-12-08 | Vitamins, Inc. | Mass separation of liquid or soluble components from solid materials utilizing supercritical fluids |
| ES2052564T3 (es) | 1986-07-08 | 1994-07-16 | Suntory Ltd | Procedimiento para la produccion de acido bishomo-gamma-linolenico y acido eicosapanteonico. |
| US5246841A (en) | 1986-12-26 | 1993-09-21 | Sagami Chemical Research Center | Microbial process for production of eicosapentaenoic acid |
| JP2582622B2 (ja) | 1987-10-27 | 1997-02-19 | 日東化学工業株式会社 | 糸状菌による高度不飽和脂肪酸の製造法 |
| US5340742A (en) | 1988-09-07 | 1994-08-23 | Omegatech Inc. | Process for growing thraustochytrium and schizochytrium using non-chloride salts to produce a microfloral biomass having omega-3-highly unsaturated fatty acids |
| US5244921A (en) | 1990-03-21 | 1993-09-14 | Martek Corporation | Eicosapentaenoic acids and methods for their production |
| US5658767A (en) | 1991-01-24 | 1997-08-19 | Martek Corporation | Arachidonic acid and methods for the production and use thereof |
| US5246842A (en) | 1991-10-30 | 1993-09-21 | The United States Of America As Represented By The Secretary Of Agriculture | Production of eicosapentaenoic acid from filamentous fungi utilizing lactose as a primary carbon source |
| JPH05308978A (ja) | 1992-05-11 | 1993-11-22 | Onoda Cement Co Ltd | 藻類によるドコサヘキサエン酸の製造方法 |
| DE4219360C2 (de) * | 1992-06-12 | 1994-07-28 | Milupa Ag | Verfahren zur Gewinnung von Lipiden mit einem hohen Anteil von langkettig-hochungesättigten Fettsäuren |
| AU5346296A (en) | 1995-04-17 | 1996-11-07 | Japan As Represented By Director-General Of Agency Of Industrial Science And Technology | Novel microorganisms capable of producing highly unsaturated fatty acids and process for producing highly unsaturated fa tty acids by using the microorganisms |
| US6255505B1 (en) | 1996-03-28 | 2001-07-03 | Gist-Brocades, B.V. | Microbial polyunsaturated fatty acid containing oil from pasteurised biomass |
| EP1506996A3 (en) * | 1996-03-28 | 2006-06-14 | DSM IP Assets B.V. | Preparation of microbial polyunsaturated fatty acid containing oil from pasteurised biomass |
| DK0935667T3 (da) | 1996-07-23 | 2007-04-10 | Nagase Chemtex Corp | Fremgangsmåde til fremstilling af docosahexaensyre og docosapentaensyre |
| US5968809A (en) | 1997-04-11 | 1999-10-19 | Abbot Laboratories | Methods and compositions for synthesis of long chain poly-unsaturated fatty acids |
| KR19990046733A (ko) | 1999-04-20 | 1999-07-05 | 류성구 | 미생물슈도모나스에의한도코사핵사노인산(ｄｈａ)의제조방법 |
| GB2377455A (en) | 2001-02-09 | 2003-01-15 | Univ Hull | Method of culturing crypthecodinium cohnii |
| DK1513941T3 (en) * | 2002-06-19 | 2016-04-18 | Dsm Ip Assets Bv | PREPARATION OF MICROBIAL OILS CONTAINING MULTI-Saturated FAT ACIDS |
| JP4280158B2 (ja) | 2002-12-27 | 2009-06-17 | 富士フイルム株式会社 | ドコサヘキサエン酸生産能を有する微生物及びその利用 |
| US7214491B2 (en) * | 2003-05-07 | 2007-05-08 | E. I. Du Pont De Nemours And Company | Δ-12 desaturase gene suitable for altering levels of polyunsaturated fatty acids in oleaginous yeasts |
| US8313911B2 (en) | 2003-05-07 | 2012-11-20 | E I Du Pont De Nemours And Company | Production of polyunsaturated fatty acids in oleaginous yeasts |
| US7238482B2 (en) | 2003-05-07 | 2007-07-03 | E. I. Du Pont De Nemours And Company | Production of polyunsaturated fatty acids in oleaginous yeasts |
| US7504259B2 (en) * | 2003-11-12 | 2009-03-17 | E. I. Du Pont De Nemours And Company | Δ12 desaturases suitable for altering levels of polyunsaturated fatty acids in oleaginous yeast |
| AU2005250074B2 (en) | 2004-06-04 | 2011-04-14 | Fluxome Sciences A/S | Metabolically engineered cells for the production of polyunsaturated fatty acids |
| US7550651B2 (en) | 2004-06-25 | 2009-06-23 | E.I. Du Pont De Nemours And Company | Delta-8 desaturase and its use in making polyunsaturated fatty acids |
| US7465564B2 (en) | 2004-08-10 | 2008-12-16 | E.I. Du Pont De Nemours And Company | Production of γ-linolenic acid in oleaginous yeast |
| US7879591B2 (en) | 2004-11-04 | 2011-02-01 | E.I. Du Pont De Nemours And Company | High eicosapentaenoic acid producing strains of Yarrowia lipolytica |
| US7550286B2 (en) | 2004-11-04 | 2009-06-23 | E. I. Du Pont De Nemours And Company | Docosahexaenoic acid producing strains of Yarrowia lipolytica |
| JP4849806B2 (ja) * | 2005-02-08 | 2012-01-11 | 日本水産株式会社 | 新規な菌体処理方法を用いた高度不飽和脂肪酸の製造方法 |
| CN103589650A (zh) | 2005-03-18 | 2014-02-19 | 米克罗比亚公司 | 产油酵母和真菌中类胡萝卜素的产生 |
| US7470532B2 (en) | 2005-10-19 | 2008-12-30 | E.I. Du Pont De Nemours And Company | Mortierella alpina C16/18 fatty acid elongase |
| WO2007061742A1 (en) | 2005-11-23 | 2007-05-31 | E. I. Du Pont De Nemours And Company | Delta-9 elongases and their use in making polyunsaturated fatty acids |
| US7678560B2 (en) | 2006-05-17 | 2010-03-16 | E.I. Du Pont De Nemours And Company | Δ 5 desaturase and its use in making polyunsaturated fatty acids |
| US7695950B2 (en) | 2006-05-17 | 2010-04-13 | E. I. Du Pont De Nemours And Company | Δ5 desaturase and its use in making polyunsaturated fatty acids |
| WO2008054565A1 (en) | 2006-10-30 | 2008-05-08 | E. I. Du Pont De Nemours And Company | Δ17 desaturase and its use in making polyunsaturated fatty acids |
| US7709239B2 (en) | 2006-12-07 | 2010-05-04 | E.I. Du Pont De Nemours And Company | Mutant Δ8 desaturase genes engineered by targeted mutagenesis and their use in making polyunsaturated fatty acids |
| DK2129777T3 (en) | 2007-04-03 | 2016-01-25 | Du Pont | MULTIZYMER AND USE THEREOF FOR THE PRODUCTION OF polyunsaturated fatty acids |
| US8188338B2 (en) | 2007-04-10 | 2012-05-29 | E. I. Du Pont De Nemours And Company | Delta-8 desaturases and their use in making polyunsaturated fatty acids |
| US8119860B2 (en) | 2007-04-16 | 2012-02-21 | E. I. Du Pont De Nemours And Company | Delta-9 elongases and their use in making polyunsaturated fatty acids |
| US7943365B2 (en) | 2007-05-03 | 2011-05-17 | E.I. Du Pont De Nemours And Company | Δ-5 desaturases and their use in making polyunsaturated fatty acids |
| US8323935B2 (en) | 2007-10-03 | 2012-12-04 | E I Du Pont De Nemours And Company | Optimized strains of Yarrowia lipolytica for high eicosapentaenoic acid production |
| US8586104B2 (en) * | 2008-04-10 | 2013-11-19 | U.S. Nutraceuticals, LLC | Plant derived seed extract rich in essentially fatty acids derived from Salvia hispanica L. seed: composition of matter, manufacturing process and use |
| DK2324119T3 (en) | 2008-09-19 | 2016-07-18 | Du Pont | Mutant DELTA5 Desaturases AND USE THEREOF FOR THE PRODUCTION OF polyunsaturated fatty acids |
| CA2744716C (en) | 2008-12-18 | 2017-05-23 | E.I. Du Pont De Nemours And Company | Reducing byproduction of malonates in a fermentation process |
| US8399226B2 (en) | 2009-06-16 | 2013-03-19 | E I Du Pont De Nemours And Company | High eicosapentaenoic acid oils from improved optimized strains of Yarrowia lipolytica |
| JP6061866B2 (ja) * | 2011-02-11 | 2017-01-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 微生物バイオマスから脂質含有組成物を得る方法 |
-
2011
- 2011-04-20 CN CN2011800202385A patent/CN103282474A/zh active Pending
- 2011-04-20 CA CA2795460A patent/CA2795460A1/en not_active Abandoned
- 2011-04-20 WO PCT/US2011/033142 patent/WO2011133610A1/en not_active Ceased
- 2011-04-20 US US13/090,373 patent/US20110263709A1/en not_active Abandoned
- 2011-04-20 JP JP2013506252A patent/JP2013525549A/ja not_active Abandoned
- 2011-04-20 AU AU2011242843A patent/AU2011242843A1/en not_active Abandoned
- 2011-04-20 EP EP11718570A patent/EP2561050A1/en not_active Withdrawn
-
2012
- 2012-10-17 CL CL2012002897A patent/CL2012002897A1/es unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP2561050A1 (en) | 2013-02-27 |
| JP2013525549A (ja) | 2013-06-20 |
| CL2012002897A1 (es) | 2014-04-11 |
| CN103282474A (zh) | 2013-09-04 |
| US20110263709A1 (en) | 2011-10-27 |
| WO2011133610A1 (en) | 2011-10-27 |
| AU2011242843A1 (en) | 2012-09-27 |
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