AU2002366642B2 - Extraction and winterization of lipids from oilseed and microbial sources - Google Patents
Extraction and winterization of lipids from oilseed and microbial sources Download PDFInfo
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- AU2002366642B2 AU2002366642B2 AU2002366642A AU2002366642A AU2002366642B2 AU 2002366642 B2 AU2002366642 B2 AU 2002366642B2 AU 2002366642 A AU2002366642 A AU 2002366642A AU 2002366642 A AU2002366642 A AU 2002366642A AU 2002366642 B2 AU2002366642 B2 AU 2002366642B2
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- lipid
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- biomass
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- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
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- 239000001659 canthaxanthin Substances 0.000 description 1
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- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001746 carotenes Chemical class 0.000 description 1
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- 239000003518 caustics Substances 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 235000017471 coenzyme Q10 Nutrition 0.000 description 1
- 229940108924 conjugated linoleic acid Drugs 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 239000000287 crude extract Substances 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- AVSXSVCZWQODGV-DPAQBDIFSA-N desmosterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@@H](CCC=C(C)C)C)[C@@]1(C)CC2 AVSXSVCZWQODGV-DPAQBDIFSA-N 0.000 description 1
- 238000009882 destearinating Methods 0.000 description 1
- 235000015872 dietary supplement Nutrition 0.000 description 1
- HOBAELRKJCKHQD-QNEBEIHSSA-N dihomo-γ-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(O)=O HOBAELRKJCKHQD-QNEBEIHSSA-N 0.000 description 1
- IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
- 238000007922 dissolution test Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000000855 fermentation Methods 0.000 description 1
- 230000004151 fermentation Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 description 1
- VZCCETWTMQHEPK-QNEBEIHSSA-N gamma-linolenic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/CCCCC(O)=O VZCCETWTMQHEPK-QNEBEIHSSA-N 0.000 description 1
- 235000020664 gamma-linolenic acid Nutrition 0.000 description 1
- 229960002733 gamolenic acid Drugs 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- JQOAQUXIUNVRQW-UHFFFAOYSA-N hexane Chemical compound CCCCCC.CCCCCC JQOAQUXIUNVRQW-UHFFFAOYSA-N 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- AGBQKNBQESQNJD-UHFFFAOYSA-M lipoate Chemical compound [O-]C(=O)CCCCC1CCSS1 AGBQKNBQESQNJD-UHFFFAOYSA-M 0.000 description 1
- 235000019136 lipoic acid Nutrition 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 235000012680 lutein Nutrition 0.000 description 1
- 239000001656 lutein Substances 0.000 description 1
- 229960005375 lutein Drugs 0.000 description 1
- KBPHJBAIARWVSC-RGZFRNHPSA-N lutein Chemical compound C([C@H](O)CC=1C)C(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\[C@H]1C(C)=C[C@H](O)CC1(C)C KBPHJBAIARWVSC-RGZFRNHPSA-N 0.000 description 1
- ORAKUVXRZWMARG-WZLJTJAWSA-N lutein Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2C(=CC(O)CC2(C)C)C ORAKUVXRZWMARG-WZLJTJAWSA-N 0.000 description 1
- 235000012661 lycopene Nutrition 0.000 description 1
- 239000001751 lycopene Substances 0.000 description 1
- OAIJSZIZWZSQBC-GYZMGTAESA-N lycopene Chemical compound CC(C)=CCC\C(C)=C\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C=C(/C)CCC=C(C)C OAIJSZIZWZSQBC-GYZMGTAESA-N 0.000 description 1
- 229960004999 lycopene Drugs 0.000 description 1
- 230000002934 lysing effect Effects 0.000 description 1
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- CKQVRZJOMJRTOY-UHFFFAOYSA-N octadecanoic acid;propane-1,2,3-triol Chemical compound OCC(O)CO.CCCCCCCCCCCCCCCCCC(O)=O CKQVRZJOMJRTOY-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
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- 150000003254 radicals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229940092258 rosemary extract Drugs 0.000 description 1
- 235000020748 rosemary extract Nutrition 0.000 description 1
- 239000001233 rosmarinus officinalis l. extract Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
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- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229960002663 thioctic acid Drugs 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 235000019148 tocotrienols Nutrition 0.000 description 1
- ZCIHMQAPACOQHT-ZGMPDRQDSA-N trans-isorenieratene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/c1c(C)ccc(C)c1C)C=CC=C(/C)C=Cc2c(C)ccc(C)c2C ZCIHMQAPACOQHT-ZGMPDRQDSA-N 0.000 description 1
- 235000010692 trans-unsaturated fatty acids Nutrition 0.000 description 1
- 150000003669 ubiquinones Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 235000008210 xanthophylls Nutrition 0.000 description 1
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Classifications
-
- 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
- C11B1/00—Production of fats or fatty oils from raw materials
-
- 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
- C11B1/00—Production of fats or fatty oils from raw materials
- C11B1/10—Production of fats or fatty oils from raw materials by extracting
-
- 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
- C11B3/00—Refining fats or fatty oils
- C11B3/006—Refining fats or fatty oils by extraction
-
- 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
- C11B7/0008—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents
- C11B7/0025—Separation of mixtures of fats or fatty oils into their constituents, e.g. saturated oils from unsaturated oils by differences of solubilities, e.g. by extraction, by separation from a solution by means of anti-solvents in solvents containing oxygen in their molecule
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Analytical Chemistry (AREA)
- Fats And Perfumes (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Extraction Or Liquid Replacement (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Edible Oils And Fats (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2009200718A AU2009200718B2 (en) | 2001-12-12 | 2009-02-24 | Extraction and winterization of lipids from oilseed and microbial sources |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US34118001P | 2001-12-12 | 2001-12-12 | |
| US60/341,180 | 2001-12-12 | ||
| PCT/US2002/039930 WO2003049832A1 (en) | 2001-12-12 | 2002-12-12 | Extraction and winterization of lipids from oilseed and microbial sources |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009200718A Division AU2009200718B2 (en) | 2001-12-12 | 2009-02-24 | Extraction and winterization of lipids from oilseed and microbial sources |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2002366642A1 AU2002366642A1 (en) | 2003-06-23 |
| AU2002366642B2 true AU2002366642B2 (en) | 2008-12-11 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2002366642A Ceased AU2002366642B2 (en) | 2001-12-12 | 2002-12-12 | Extraction and winterization of lipids from oilseed and microbial sources |
| AU2009200718A Expired - Fee Related AU2009200718B2 (en) | 2001-12-12 | 2009-02-24 | Extraction and winterization of lipids from oilseed and microbial sources |
| AU2011250697A Abandoned AU2011250697A1 (en) | 2001-12-12 | 2011-11-10 | Extraction and winterization of lipids from oilseed and microbial sources |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2009200718A Expired - Fee Related AU2009200718B2 (en) | 2001-12-12 | 2009-02-24 | Extraction and winterization of lipids from oilseed and microbial sources |
| AU2011250697A Abandoned AU2011250697A1 (en) | 2001-12-12 | 2011-11-10 | Extraction and winterization of lipids from oilseed and microbial sources |
Country Status (9)
| Country | Link |
|---|---|
| US (4) | US7419596B2 (cg-RX-API-DMAC7.html) |
| EP (3) | EP2239028A1 (cg-RX-API-DMAC7.html) |
| JP (3) | JP4647212B2 (cg-RX-API-DMAC7.html) |
| CN (1) | CN1267174C (cg-RX-API-DMAC7.html) |
| AT (1) | ATE522264T1 (cg-RX-API-DMAC7.html) |
| AU (3) | AU2002366642B2 (cg-RX-API-DMAC7.html) |
| CA (2) | CA2718374C (cg-RX-API-DMAC7.html) |
| NO (1) | NO20042929L (cg-RX-API-DMAC7.html) |
| WO (1) | WO2003049832A1 (cg-RX-API-DMAC7.html) |
Families Citing this family (85)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1267174C (zh) | 2001-12-12 | 2006-08-02 | 马泰克生物科学博尔德公司 | 从含油种子和微生物来源提取和冬化脂类的方法 |
| US7122216B2 (en) * | 2003-06-16 | 2006-10-17 | I.P. Holdings, L.L.C. | Vegetable oil extraction methods |
| DK1656449T3 (da) | 2003-08-21 | 2009-06-02 | Monsanto Technology Llc | Fedtsyredesaturaser fra primula |
| US20050215640A1 (en) | 2004-03-26 | 2005-09-29 | Baxter Jeffrey H | HMB compositions and uses thereof |
| EP2902021B1 (en) | 2004-04-16 | 2018-11-14 | Monsanto Technology LLC | Expression of fatty acid desaturases in corn |
| PL1809118T3 (pl) | 2004-11-04 | 2017-07-31 | Monsanto Technology Llc | Kompozycje oleju z nasion |
| CN101098628B (zh) * | 2004-11-04 | 2010-09-01 | 孟山都技术公司 | 种子油组合物 |
| EP2447356B1 (en) | 2005-06-07 | 2016-04-20 | DSM Nutritional Products AG | Eukaryotic microorganisms for producing lipids and antioxidants |
| EP1903883A4 (en) * | 2005-07-01 | 2010-06-23 | Martek Biosciences Corp | OIL PRODUCT CONTAINING MULTIPLE UNSATURATED FATTY ACIDS AND ITS USES AND MANUFACTURING |
| CA2632262C (en) * | 2005-12-19 | 2015-04-07 | Abbott Laboratories | Method of using .beta.-hydroxy-.beta.-methylbutyrate |
| CA2645148C (en) | 2006-03-10 | 2018-05-22 | Monsanto Technology Llc | Soybean seed and oil compositions and methods of making same |
| BRPI0715442B1 (pt) | 2006-07-21 | 2018-01-30 | Xyleco, Inc. | Método para produzir produtos a partir de material celulósico ou lignocelulósico em biomassa |
| ES2572833T3 (es) | 2006-08-01 | 2016-06-02 | Dsm Nutritional Products Ag | Proceso de producción de aceite microbiano que contiene ácidos grasos poliinsaturados |
| DE102007037783A1 (de) * | 2007-08-10 | 2009-02-19 | Cognis Ip Management Gmbh | Lipophile Zubereitungen |
| EP2262376B1 (en) * | 2008-03-17 | 2017-08-09 | Stepan Specialty Products, LLC | Process for refining a triglyceride oil |
| US8043496B1 (en) | 2008-03-18 | 2011-10-25 | Peter Allen Schuh | System for extracting oil from algae |
| US9896642B2 (en) | 2008-10-14 | 2018-02-20 | Corbion Biotech, Inc. | Methods of microbial oil extraction and separation |
| SG10201401472YA (en) * | 2009-04-14 | 2014-08-28 | Solazyme Inc | Methods Of Microbial Oil Extraction And Separation |
| US9480271B2 (en) | 2009-09-15 | 2016-11-01 | Monsanto Technology Llc | Soybean seed and oil compositions and methods of making same |
| US8552098B2 (en) * | 2009-09-30 | 2013-10-08 | Dow Global Technologies Llc | Purified acetylated derivatives of castor oil and compositions including same |
| US20130101723A1 (en) * | 2009-11-03 | 2013-04-25 | Daniel Verkoeijen | Vegetable oil comprising a polyunsaturated fatty acid having at least 20 carbon atoms |
| JP5920890B2 (ja) | 2010-01-19 | 2016-05-18 | ディーエスエム アイピー アセッツ ビー．ブイ． | エイコサペンタエン酸生成微生物、脂肪酸組成物、ならびにそれらを作る方法およびそれらの使用 |
| US8187861B1 (en) | 2010-01-26 | 2012-05-29 | Allen John Schuh | Phosphate removal-recovery and biofuel feedstock system |
| CN102711524B (zh) | 2010-01-29 | 2014-09-10 | 雅培制药有限公司 | 包含hmb钙的营养乳剂 |
| PE20121730A1 (es) | 2010-01-29 | 2013-01-13 | Abbott Lab | Liquidos nutricionales envasados asepticamente que comprenden beta-hidroxi-beta-metilbutirato (hmb) |
| US9693577B2 (en) | 2010-01-29 | 2017-07-04 | Abbott Laboratories | Method of preparing a nutritional powder comprising spray dried HMB |
| US8313648B2 (en) | 2010-04-06 | 2012-11-20 | Heliae Development, Llc | Methods of and systems for producing biofuels from algal oil |
| US8115022B2 (en) * | 2010-04-06 | 2012-02-14 | Heliae Development, Llc | Methods of producing biofuels, chlorophylls and carotenoids |
| US8308951B1 (en) | 2010-04-06 | 2012-11-13 | Heliae Development, Llc | Extraction of proteins by a two solvent method |
| US8475660B2 (en) | 2010-04-06 | 2013-07-02 | Heliae Development, Llc | Extraction of polar lipids by a two solvent method |
| US8211309B2 (en) | 2010-04-06 | 2012-07-03 | Heliae Development, Llc | Extraction of proteins by a two solvent method |
| AU2011237698A1 (en) | 2010-04-06 | 2012-10-11 | Heliae Development, Llc | Selective extraction of proteins from freshwater algae |
| WO2011127127A2 (en) | 2010-04-06 | 2011-10-13 | Arizona Board Of Regents For And On Behalf Of Arizona State University | Extraction with fractionation of oil and co-products from oleaginous material |
| US8273248B1 (en) | 2010-04-06 | 2012-09-25 | Heliae Development, Llc | Extraction of neutral lipids by a two solvent method |
| US8202425B2 (en) | 2010-04-06 | 2012-06-19 | Heliae Development, Llc | Extraction of neutral lipids by a two solvent method |
| US8211308B2 (en) | 2010-04-06 | 2012-07-03 | Heliae Development, Llc | Extraction of polar lipids by a two solvent method |
| US20130217904A1 (en) * | 2010-04-06 | 2013-08-22 | Heliae Development, Llc | Method of extracting polar lipids and neutral lipids with two solvents |
| US20140005422A1 (en) * | 2010-04-06 | 2014-01-02 | Heliae Development, Llc | Method of extracting neutral lipids with two solvents |
| US10125331B2 (en) * | 2010-04-29 | 2018-11-13 | Advanced Energy Development | Renewable oil refining processes |
| EP3617318A1 (en) * | 2010-06-01 | 2020-03-04 | DSM IP Assets B.V. | Extraction of lipid from cells and products therefrom |
| TWI526161B (zh) | 2010-06-10 | 2016-03-21 | 亞培公司 | 包含鈣ｈｍｂ及可溶性蛋白質之實質上透明營養液 |
| SG185578A1 (en) | 2010-06-14 | 2013-01-30 | Io Mega Holding Corp | Methods for the production of algae derived oils |
| DK2450425T3 (da) * | 2010-11-08 | 2014-07-07 | Neste Oil Oyj | Fremgangsmåde til lipidekstraktion fra biomasse |
| CA3026436A1 (en) | 2011-02-11 | 2012-08-16 | E. I. Du Pont De Nemours And Company | Method for obtaining a lipid-containing composition from microbial biomass |
| AU2012214285A1 (en) | 2011-02-11 | 2013-07-18 | E. I. Du Pont De Nemours And Company | Purification of triglyceride oil from microbial sources using short path distillation |
| US8365462B2 (en) | 2011-05-31 | 2013-02-05 | Heliae Development, Llc | V-Trough photobioreactor systems |
| USD661164S1 (en) | 2011-06-10 | 2012-06-05 | Heliae Development, Llc | Aquaculture vessel |
| USD682637S1 (en) | 2011-06-10 | 2013-05-21 | Heliae Development, Llc | Aquaculture vessel |
| USD679965S1 (en) | 2011-06-10 | 2013-04-16 | Heliae Development, Llc | Aquaculture vessel |
| US10383839B2 (en) | 2011-06-30 | 2019-08-20 | Johnson & Johnson Vision Care, Inc. | Esters for treatment of ocular inflammatory conditions |
| EP2952183A1 (en) | 2011-07-21 | 2015-12-09 | DSM IP Assets B.V. | Fatty acid compositions |
| KR20220059969A (ko) | 2011-11-01 | 2022-05-10 | 디에스엠 아이피 어셋츠 비.브이. | 산화적으로 안정한 다중불포화된 지방산 함유 오일 |
| WO2013075116A2 (en) | 2011-11-17 | 2013-05-23 | Heliae Development, Llc | Omega 7 rich compositions and methods of isolating omega 7 fatty acids |
| CN103156003B (zh) * | 2011-12-16 | 2015-04-29 | 丰益(上海)生物技术研发中心有限公司 | 一种调和油及其制备方法 |
| WO2013172087A1 (ja) * | 2012-05-17 | 2013-11-21 | 株式会社竹田測量設計 | 一酸化窒素産生阻害活性を備える組成物 |
| US9632797B2 (en) | 2013-01-31 | 2017-04-25 | Hewlett Packard Enterprise Development Lp | Updating a commit list to indicate data to be written to a firmware interface variable repository |
| WO2014141098A1 (en) | 2013-03-13 | 2014-09-18 | Dsm Nutritional Products Ag | Engineering microorganisms |
| KR102435269B1 (ko) | 2013-12-20 | 2022-08-22 | 디에스엠 아이피 어셋츠 비.브이. | 미생물 세포로부터의 미생물 오일의 수득 방법 |
| AR098890A1 (es) | 2013-12-20 | 2016-06-22 | Dsm Ip Assets Bv | Proceso para obtener aceite microbiano a partir de células microbianas |
| AU2014369042B2 (en) | 2013-12-20 | 2020-04-30 | Dsm Ip Assets B.V. | Processes for obtaining microbial oil from microbial cells |
| US11124736B2 (en) | 2013-12-20 | 2021-09-21 | Dsm Ip Assets B.V. | Processes for obtaining microbial oil from microbial cells |
| CA2934509C (en) | 2013-12-20 | 2022-05-03 | Neil Francis Leininger | Processes for obtaining microbial oil from microbial cells |
| ES2727082T3 (es) * | 2014-05-30 | 2019-10-14 | Drei Lilien Pvg Gmbh&Co Kg | Método para purificar fases lipídicas refinadas |
| CN107532179B (zh) * | 2014-11-14 | 2021-10-15 | 巴斯夫植物科学有限公司 | 产生pufa的材料和方法及含有pufa的组合物 |
| AR104042A1 (es) | 2015-03-26 | 2017-06-21 | Mara Renewables Corp | Producción de alta densidad de biomasa y aceite utilizando glicerol en bruto |
| JP6977231B2 (ja) | 2015-07-13 | 2021-12-08 | マラ リニューアブルズ コーポレーション | Ｃ５有機炭素の微生物による代謝の増強 |
| US10851395B2 (en) | 2016-06-10 | 2020-12-01 | MARA Renewables Corporation | Method of making lipids with improved cold flow properties |
| KR102405390B1 (ko) | 2016-07-13 | 2022-06-03 | 에보닉 오퍼레이션스 게엠베하 | 용해된 지질을 함유하는 바이오매스로부터 지질을 분리하는 방법 |
| CN106343045A (zh) * | 2016-08-11 | 2017-01-25 | 青岛俏宝食品有限公司 | 一种富含长碳链多不饱和脂肪酸类脂质的营养强化型功能低温食用调和油脂 |
| RU2744913C2 (ru) | 2016-12-27 | 2021-03-17 | Эвоник Оперейшенс ГмбХ | Способ выделения липидов из липидсодержащей биомассы |
| CN110267654A (zh) * | 2017-02-22 | 2019-09-20 | 嘉吉公司 | 含dha的油的纯化 |
| EP3470502A1 (en) | 2017-10-13 | 2019-04-17 | Evonik Degussa GmbH | Method of separating lipids from a lysed lipids containing biomass |
| WO2019048327A1 (en) * | 2017-09-05 | 2019-03-14 | Evonik Degussa Gmbh | METHOD FOR SEPARATING LIPIDS IN A BIOMASS CONTAINING LYDE LIPIDS |
| EP3527664A1 (en) | 2018-02-15 | 2019-08-21 | Evonik Degussa GmbH | Method of isolating lipids from a lipids containing biomass |
| JP2021521882A (ja) * | 2018-04-20 | 2021-08-30 | ナノ アルジー ソリューションズ アーゲー | エイコサペンタエン酸オイル組成物を提供するための新規なプロセス |
| BR112020023222A2 (pt) | 2018-05-15 | 2021-03-23 | Evonik Operations Gmbh | método de isolamento de lipídios a partir de uma biomassa contendo lipídios lisados por inversão por emulsão |
| DK3794097T3 (da) | 2018-05-15 | 2024-12-16 | Evonik Operations Gmbh | Fremgangsmåde til isolering af lipider fra en lipid-indeholdende biomasse ved hjælp af hydrofob silica |
| EP3586642A1 (en) | 2018-06-21 | 2020-01-01 | Nuseed Pty Ltd | Ala enriched polyunsaturated fatty acid compositions |
| EP3586640A1 (en) | 2018-06-21 | 2020-01-01 | Nuseed Pty Ltd | Dha enriched polyunsaturated fatty acid compositions |
| FR3085962B1 (fr) | 2018-09-14 | 2021-06-18 | Fermentalg | Procede d'extracton d'une huile riche en pufa |
| FR3085825B1 (fr) | 2018-09-14 | 2021-07-16 | Fermentalg | Huile de microorganismes riche en acide docosahexaenoique |
| CN109731102B (zh) * | 2019-01-31 | 2022-05-17 | 广州白云山汉方现代药业有限公司 | 一种降低橄榄油甲氧基苯胺值的方法 |
| KR102673054B1 (ko) * | 2023-05-31 | 2024-06-07 | 종근당건강 주식회사 | 산패 억제 및 산화 안정성이 우수한 유지조성물 및 이를 포함하는 연질캡슐 |
| CN117844647B (zh) * | 2023-12-15 | 2025-12-09 | 嘉必优生物技术（武汉）股份有限公司 | 一种产高含量、高澄清度油脂的裂殖壶菌及其应用 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5959644A (ja) * | 1982-09-29 | 1984-04-05 | Kureha Chem Ind Co Ltd | 魚油中のエイコサペンタエン酸を濃縮する方法 |
| WO1986004354A1 (en) * | 1985-01-22 | 1986-07-31 | Japan As Represented By Director General Of Agency | Method for obtaining lipids from fungus bodies |
| US6166230A (en) * | 1996-05-15 | 2000-12-26 | Gist-Brocades B.V. | Sterol extraction with polar solvent to give low sterol, high triglyceride, microbial oil |
Family Cites Families (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3541123A (en) * | 1968-10-21 | 1970-11-17 | Kao Corp | Process for the fractionation of oils and fats |
| US4205006A (en) * | 1973-03-05 | 1980-05-27 | The United States Of America As Represented By The Secretary Of Agriculture | Physiochemically designed fat compositions from tallow and process for making |
| US3944585A (en) * | 1973-03-05 | 1976-03-16 | The United States Of America As Represented By The Secretary Of Agriculture | Multi-step crystallization and blending process for making physiochemically designed fat compositions from tallow |
| JPS5967241A (ja) * | 1982-10-08 | 1984-04-16 | Kureha Chem Ind Co Ltd | 魚油中のエイコサペンタエン酸の濃縮方法 |
| JPS60133094A (ja) * | 1983-12-21 | 1985-07-16 | 日清製油株式会社 | 高純度エイコサペンタエン酸の製造法 |
| JPS61192292A (ja) * | 1985-02-21 | 1986-08-26 | Agency Of Ind Science & Technol | γ−リノレン酸含有グリセリドの濃縮方法 |
| US4792418A (en) * | 1985-08-14 | 1988-12-20 | Century Laboratories, Inc. | Method of extraction and purification of polyunsaturated fatty acids from natural sources |
| KR970007568B1 (ko) * | 1990-03-12 | 1997-05-10 | 솔라 에이나 | 다가불포화 지방산과 인지질 강화지방 제조방법과 강화지방의 용도 |
| US5658767A (en) | 1991-01-24 | 1997-08-19 | Martek Corporation | Arachidonic acid and methods for the production and use thereof |
| JP3354582B2 (ja) * | 1991-09-30 | 2002-12-09 | サントリー株式会社 | オメガ９系高度不飽和脂肪酸およびこれを含有する脂質の製造方法 |
| DE4219360C2 (de) * | 1992-06-12 | 1994-07-28 | Milupa Ag | Verfahren zur Gewinnung von Lipiden mit einem hohen Anteil von langkettig-hochungesättigten Fettsäuren |
| ATE199481T1 (de) * | 1995-11-24 | 2001-03-15 | Loders Croklaan Bv | Zusammensetzung auf basis von fischöl |
| US6255505B1 (en) * | 1996-03-28 | 2001-07-03 | Gist-Brocades, B.V. | Microbial polyunsaturated fatty acid containing oil from pasteurised biomass |
| CN104017734A (zh) * | 1996-03-28 | 2014-09-03 | Dsmip资产有限公司 | 粒状微生物生物质的制备及其有价值的化合物的分离方法 |
| JP3343358B2 (ja) | 1996-07-23 | 2002-11-11 | ナガセケムテックス株式会社 | ドコサヘキサエン酸およびドコサペンタエン酸の製造方法 |
| EP1003869A1 (en) * | 1997-06-04 | 2000-05-31 | Calgene LLC | Production of polyunsaturated fatty acids by expression of polyketide-like synthesis genes in plants |
| KR20080007279A (ko) * | 2000-01-19 | 2008-01-17 | 마텍 바이오싸이언스스 코포레이션 | 무용매 추출 방법 |
| JP3425622B2 (ja) * | 2000-03-30 | 2003-07-14 | 独立行政法人産業技術総合研究所 | ラビリンチュラ属菌を用いた高度不飽和脂肪酸含有培養物および高度不飽和脂肪酸含有油脂の製造方法 |
| US6344574B1 (en) * | 2000-07-20 | 2002-02-05 | The United States Of America As Represented By The Secretary Of Agriculture | Solvent fractionation of chicken fat for making lipid compositions enriched in unsaturated fatty acid-containing triacylglycerols |
| EP1178103A1 (en) * | 2000-08-02 | 2002-02-06 | Dsm N.V. | Purifying crude pufa oils |
| CN1109093C (zh) * | 2000-09-28 | 2003-05-21 | 中国科学院武汉病毒研究所 | 一种微生物油脂的制备方法 |
| EP1322752B2 (en) * | 2000-09-28 | 2015-02-11 | Bioriginal Food & Science Corp. | Fad4, fad5, fad5-2, and fad6, fatty acid desaturase family members and uses thereof |
| EP1215274A1 (en) * | 2000-12-15 | 2002-06-19 | Dsm N.V. | Enrichment of microbial oils |
| US6492537B2 (en) * | 2001-02-20 | 2002-12-10 | The United States Of America As Represented By The Secretary Of Agriculture | Solvent fractionation of menhaden oil and partially hydrogenated menhaden oil for making lipid compositions enriched in unsaturated fatty acid-containing triacylglycerols |
| DE10151155A1 (de) | 2001-10-19 | 2003-05-08 | Nutrinova Gmbh | Native PUFA-Triglyceridmischungen mit einem hohen Gehalt an mehrfach ungesättigten Fettsäuren sowie Verfahren zu deren Herstellung und deren Verwendung |
| CN1267174C (zh) | 2001-12-12 | 2006-08-02 | 马泰克生物科学博尔德公司 | 从含油种子和微生物来源提取和冬化脂类的方法 |
| US20040209953A1 (en) * | 2002-12-06 | 2004-10-21 | Wai Lee Theresa Siu-Ling | Glyceride compositions and methods of making and using same |
| US7561412B2 (en) * | 2006-09-29 | 2009-07-14 | Rockwell Automation Technologies, Inc. | System and method for automatically securing a motor control center |
| US7528612B2 (en) * | 2006-09-29 | 2009-05-05 | Rockwell Automation Technologies, Inc. | System and method for monitoring a motor control center |
| US8228067B2 (en) * | 2006-11-02 | 2012-07-24 | Production Resource Group, Llc | Load bank |
-
2002
- 2002-12-12 CN CNB028280431A patent/CN1267174C/zh not_active Expired - Fee Related
- 2002-12-12 EP EP10166318A patent/EP2239028A1/en not_active Withdrawn
- 2002-12-12 CA CA2718374A patent/CA2718374C/en not_active Expired - Fee Related
- 2002-12-12 EP EP10176356A patent/EP2261312A1/en not_active Withdrawn
- 2002-12-12 AU AU2002366642A patent/AU2002366642B2/en not_active Ceased
- 2002-12-12 JP JP2003550880A patent/JP4647212B2/ja not_active Expired - Fee Related
- 2002-12-12 CA CA2469647A patent/CA2469647C/en not_active Expired - Fee Related
- 2002-12-12 AT AT02791414T patent/ATE522264T1/de not_active IP Right Cessation
- 2002-12-12 WO PCT/US2002/039930 patent/WO2003049832A1/en not_active Ceased
- 2002-12-12 US US10/498,598 patent/US7419596B2/en not_active Expired - Lifetime
- 2002-12-12 EP EP02791414A patent/EP1453583B1/en not_active Revoked
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2004
- 2004-07-08 NO NO20042929A patent/NO20042929L/no unknown
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2008
- 2008-08-01 US US12/184,974 patent/US7695626B2/en not_active Expired - Lifetime
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2009
- 2009-02-24 AU AU2009200718A patent/AU2009200718B2/en not_active Expired - Fee Related
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2010
- 2010-03-16 JP JP2010058682A patent/JP2010196060A/ja active Pending
- 2010-04-09 US US12/757,383 patent/US8012354B2/en not_active Expired - Fee Related
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2011
- 2011-09-06 US US13/226,324 patent/US8480904B2/en not_active Expired - Fee Related
- 2011-11-10 AU AU2011250697A patent/AU2011250697A1/en not_active Abandoned
-
2013
- 2013-01-18 JP JP2013007324A patent/JP2013100530A/ja not_active Withdrawn
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5959644A (ja) * | 1982-09-29 | 1984-04-05 | Kureha Chem Ind Co Ltd | 魚油中のエイコサペンタエン酸を濃縮する方法 |
| WO1986004354A1 (en) * | 1985-01-22 | 1986-07-31 | Japan As Represented By Director General Of Agency | Method for obtaining lipids from fungus bodies |
| US6166230A (en) * | 1996-05-15 | 2000-12-26 | Gist-Brocades B.V. | Sterol extraction with polar solvent to give low sterol, high triglyceride, microbial oil |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2013100530A (ja) | 2013-05-23 |
| JP4647212B2 (ja) | 2011-03-09 |
| CA2469647C (en) | 2011-02-15 |
| US8480904B2 (en) | 2013-07-09 |
| EP2239028A1 (en) | 2010-10-13 |
| CN1620330A (zh) | 2005-05-25 |
| AU2011250697A1 (en) | 2011-12-01 |
| JP2010196060A (ja) | 2010-09-09 |
| AU2009200718B2 (en) | 2011-08-11 |
| ATE522264T1 (de) | 2011-09-15 |
| EP1453583A2 (en) | 2004-09-08 |
| JP2005513051A (ja) | 2005-05-12 |
| NO20042929L (no) | 2004-07-08 |
| WO2003049832A8 (en) | 2003-10-23 |
| CA2469647A1 (en) | 2003-06-19 |
| US20120059180A1 (en) | 2012-03-08 |
| US7419596B2 (en) | 2008-09-02 |
| CA2718374C (en) | 2013-05-07 |
| AU2002366642A1 (en) | 2003-06-23 |
| AU2009200718A1 (en) | 2009-03-19 |
| CA2718374A1 (en) | 2003-06-19 |
| WO2003049832A1 (en) | 2003-06-19 |
| US20090099379A1 (en) | 2009-04-16 |
| CN1267174C (zh) | 2006-08-02 |
| EP1453583A4 (en) | 2005-08-17 |
| US20050115897A1 (en) | 2005-06-02 |
| EP1453583B1 (en) | 2011-08-31 |
| US8012354B2 (en) | 2011-09-06 |
| US20100261919A1 (en) | 2010-10-14 |
| EP2261312A1 (en) | 2010-12-15 |
| US7695626B2 (en) | 2010-04-13 |
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