HU198171B - Process for concentrating delta 6 polyinsaturated fatty acids in the mixture of polyinsaturated fatty acids - Google Patents
Process for concentrating delta 6 polyinsaturated fatty acids in the mixture of polyinsaturated fatty acids Download PDFInfo
- Publication number
- HU198171B HU198171B HU853932A HU393285A HU198171B HU 198171 B HU198171 B HU 198171B HU 853932 A HU853932 A HU 853932A HU 393285 A HU393285 A HU 393285A HU 198171 B HU198171 B HU 198171B
- Authority
- HU
- Hungary
- Prior art keywords
- fatty acids
- mixture
- acid
- urea
- linolenic acid
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 50
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 36
- 239000000194 fatty acid Substances 0.000 title claims abstract description 36
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 36
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 36
- 238000000034 method Methods 0.000 title claims description 21
- 239000004202 carbamide Substances 0.000 claims abstract description 19
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 18
- 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 claims abstract description 17
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims abstract description 15
- 235000020664 gamma-linolenic acid Nutrition 0.000 claims abstract description 14
- 229960002733 gamolenic acid Drugs 0.000 claims abstract description 14
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims abstract description 6
- 239000002253 acid Substances 0.000 claims description 18
- 235000001466 Ribes nigrum Nutrition 0.000 claims description 10
- 235000016954 Ribes hudsonianum Nutrition 0.000 claims description 8
- 238000007127 saponification reaction Methods 0.000 claims description 7
- 240000001890 Ribes hudsonianum Species 0.000 claims description 6
- 235000013399 edible fruits Nutrition 0.000 claims description 6
- 239000007791 liquid phase Substances 0.000 claims description 6
- 235000011483 Ribes Nutrition 0.000 claims description 5
- 241000220483 Ribes Species 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 5
- 210000000614 rib Anatomy 0.000 claims description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 4
- -1 urea saturated methanol Chemical class 0.000 claims description 3
- 238000004007 reversed phase HPLC Methods 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical group 0.000 claims description 2
- 230000029087 digestion Effects 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 27
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract description 12
- 239000007858 starting material Substances 0.000 abstract description 9
- HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 abstract description 3
- 235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 abstract description 3
- 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 abstract description 3
- 239000012047 saturated solution Substances 0.000 abstract description 3
- 230000015572 biosynthetic process Effects 0.000 abstract description 2
- 239000003814 drug Substances 0.000 abstract description 2
- 238000003786 synthesis reaction Methods 0.000 abstract description 2
- 238000004128 high performance liquid chromatography Methods 0.000 abstract 1
- 230000000050 nutritive effect Effects 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- 239000012071 phase Substances 0.000 description 21
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 16
- 239000003921 oil Substances 0.000 description 12
- 235000019198 oils Nutrition 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 229960004488 linolenic acid Drugs 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000005119 centrifugation Methods 0.000 description 5
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 5
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 4
- 241001312569 Ribes nigrum Species 0.000 description 4
- 235000020778 linoleic acid Nutrition 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- 241000219925 Oenothera Species 0.000 description 2
- ZTHYODDOHIVTJV-UHFFFAOYSA-N Propyl gallate Chemical compound CCCOC(=O)C1=CC(O)=C(O)C(O)=C1 ZTHYODDOHIVTJV-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 239000010473 blackcurrant seed oil Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000002953 preparative HPLC Methods 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 0.000 description 2
- VZCCETWTMQHEPK-YHTMAJSVSA-N (6e,9e,12e)-octadeca-6,9,12-trienoic acid Chemical compound CCCCC\C=C\C\C=C\C\C=C\CCCCC(O)=O VZCCETWTMQHEPK-YHTMAJSVSA-N 0.000 description 1
- OYHQOLUKZRVURQ-UHFFFAOYSA-N 9,12-Octadecadienoic Acid Chemical compound CCCCCC=CCC=CCCCCCCCC(O)=O OYHQOLUKZRVURQ-UHFFFAOYSA-N 0.000 description 1
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical compound [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 1
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 1
- ZGTMUACCHSMWAC-UHFFFAOYSA-L EDTA disodium salt (anhydrous) Chemical compound [Na+].[Na+].OC(=O)CN(CC([O-])=O)CCN(CC(O)=O)CC([O-])=O ZGTMUACCHSMWAC-UHFFFAOYSA-L 0.000 description 1
- 235000004496 Oenothera biennis Nutrition 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000002357 Ribes grossularia Nutrition 0.000 description 1
- 244000171263 Ribes grossularia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
- VXLCKSFMONBCLQ-UHFFFAOYSA-N [Na]CC[Na] Chemical group [Na]CC[Na] VXLCKSFMONBCLQ-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 229940098330 gamma linoleic acid Drugs 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000008774 maternal effect Effects 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N n-hexadecanoic acid Natural products CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical group CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000008385 outer phase Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
- C11C1/00—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids
- C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/42—Separation; Purification; Stabilisation; Use of additives
- C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Microbiology (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Control Of El Displays (AREA)
- Bipolar Transistors (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH4858/84A CH663951A5 (fr) | 1984-10-10 | 1984-10-10 | Procede d'enrichissement selectif en acides gras polyinsatures d'un melange contenant des acides gras fractions enrichies obtenues et compositions les contenant. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT43990A HUT43990A (en) | 1988-01-28 |
| HU198171B true HU198171B (en) | 1989-08-28 |
Family
ID=4283774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU853932A HU198171B (en) | 1984-10-10 | 1985-10-10 | Process for concentrating delta 6 polyinsaturated fatty acids in the mixture of polyinsaturated fatty acids |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4776984A (enExample) |
| EP (1) | EP0178442B1 (enExample) |
| JP (1) | JP2657056B2 (enExample) |
| AT (1) | ATE33037T1 (enExample) |
| AU (1) | AU580330B2 (enExample) |
| CA (1) | CA1265156A (enExample) |
| CH (1) | CH663951A5 (enExample) |
| DE (1) | DE3561890D1 (enExample) |
| DK (1) | DK164817C (enExample) |
| ES (1) | ES8604850A1 (enExample) |
| FI (1) | FI81830C (enExample) |
| GR (1) | GR852437B (enExample) |
| HU (1) | HU198171B (enExample) |
| IL (1) | IL76349A (enExample) |
| NO (1) | NO163825C (enExample) |
| NZ (1) | NZ213767A (enExample) |
| ZA (1) | ZA857008B (enExample) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792418A (en) * | 1985-08-14 | 1988-12-20 | Century Laboratories, Inc. | Method of extraction and purification of polyunsaturated fatty acids from natural sources |
| US5243046A (en) * | 1986-12-17 | 1993-09-07 | Nestec S.A. | Process for the continuous fractionation of a mixture of fatty acids |
| CH669208A5 (fr) * | 1986-12-17 | 1989-02-28 | Nestle Sa | Procede de fractionnement en continu d'un melange d'acides gras. |
| US4999380A (en) * | 1988-10-18 | 1991-03-12 | Nestec S.A. | Treatment of lipoprotein disorders associated with cholesterol metabolism |
| US5234952A (en) * | 1988-12-23 | 1993-08-10 | Nestec S.A. | Reduction of thrombogenicity with lipids of blackcurrant seed |
| CH678181A5 (enExample) * | 1989-05-22 | 1991-08-15 | Nestle Sa | |
| EP0682006B1 (fr) * | 1994-05-09 | 1999-04-07 | Societe Des Produits Nestle S.A. | Procédé de préparation d'un concentrat d'esters d'acides gras polyinsaturés |
| EP0741183B1 (fr) * | 1995-05-04 | 1999-03-24 | Societe Des Produits Nestle S.A. | Procédé de fractionnement d'acides gras |
| JP3441630B2 (ja) * | 1997-08-08 | 2003-09-02 | 信越化学工業株式会社 | 高級不飽和脂肪族エステルの精製方法 |
| US6579551B1 (en) | 1998-05-21 | 2003-06-17 | Beech-Nut Nutrition Corporation | Baby-food compositions containing egg yolk and methods therefor |
| US6149964A (en) * | 1998-05-21 | 2000-11-21 | Beech-Nut Nutrition Corporation | Egg yolk-containing baby food compositions and methods therefor |
| US7413759B2 (en) * | 1998-05-21 | 2008-08-19 | Beech-Nut Nutrition Corporation | Method of enhancing cognitive ability in infant fed DHA containing baby-food compositions |
| US7141266B2 (en) * | 1998-05-21 | 2006-11-28 | Beech-Nut Nutrition Corporation | Baby-food compositions enhancing visual acuity and methods therefor |
| US6395778B1 (en) | 2000-01-11 | 2002-05-28 | Omegatech, Inc. | Process for making an enriched mixture of polyunsaturated fatty acid esters |
| KR20010008387A (ko) * | 2000-11-30 | 2001-02-05 | 이성권 | 결정화방법을 이용한 고순도 불포화지방산의 분리 정제 방법 |
| EP1392278A4 (en) * | 2001-05-14 | 2005-05-04 | Martek Biosciences Corp | PREPARATION AND USE OF A POLAR LIPIDREICH FRACTION WITH STEARIDONIC ACID AND GAMMA LINOLIC ACID FROM PLANT SEEDS AND MICROBES |
| EP1392623A4 (en) * | 2001-05-14 | 2005-05-04 | Martek Biosciences Corp | PREPARATION AND USE OF A POLAR LIPID RICH FRACTION CONTAINING HIGHLY UNSATURATED OMEGA-3 AND / OR OMEGA-6 FATTY ACIDS FROM MICROBES, SEEDS OF GENETICALLY MODIFIED PLANTS AND MARINE ORGANISMS |
| KR20140070676A (ko) | 2002-09-06 | 2014-06-10 | 인설트 테라페틱스, 인코퍼레이티드 | 공유결합된 치료제 전달을 위한 사이클로덱스트린-기초 중합체 |
| BR0315198A (pt) * | 2002-10-09 | 2005-08-30 | Insert Therapeutics Inc | Materiais e composições à base de ciclodextrina e usos relacionados aos mesmos |
| CA2436650A1 (en) * | 2003-08-06 | 2005-02-06 | Naturia Inc. | Conjugated linolenic acid (clnatm) compositions: synthesis, purification and uses |
| CA2881252C (en) * | 2003-08-21 | 2017-02-28 | Monsanto Technology Llc | Soybean oil having 5 to 50% sda and less than 10% gla |
| EP1734947B1 (en) | 2004-04-16 | 2015-04-15 | Monsanto Technology, LLC | Expression of fatty acid desaturases in corn |
| KR100539357B1 (ko) * | 2005-04-11 | 2005-12-28 | 동부한농화학 주식회사 | 불포화 지방산의 제조방법 |
| US20070299271A1 (en) * | 2006-06-27 | 2007-12-27 | Udaya Nayanskantha Wanasundara | Process for separating saturated and unsaturated fatty acids for producing cold-tolorant biodiesel fuel from soy oil |
| US8003813B2 (en) * | 2006-06-27 | 2011-08-23 | Pos Pilot Plant Corporation | Process for separating saturated and unsaturated fatty acids |
| US20080176958A1 (en) | 2007-01-24 | 2008-07-24 | Insert Therapeutics, Inc. | Cyclodextrin-based polymers for therapeutics delivery |
| US8974814B2 (en) * | 2007-11-12 | 2015-03-10 | California Institute Of Technology | Layered drug delivery polymer monofilament fibers |
| GB0907413D0 (en) | 2009-04-29 | 2009-06-10 | Equateq Ltd | Novel methods |
| EP2496546B1 (en) | 2009-11-05 | 2016-01-27 | Purdue Research Foundation | Method of lowering the cloud point of fatty acid esters |
| CA2856715A1 (en) * | 2011-11-29 | 2013-06-06 | Dignity Sciences Limited | Compositions comprising 20-carbon fatty acids and methods of making and using same |
| WO2014055493A1 (en) | 2012-10-02 | 2014-04-10 | Cerulean Pharma Inc. | Methods and systems for polymer precipitation and generation of particles |
| ES2872449T3 (es) * | 2013-12-04 | 2021-11-02 | Nippon Suisan Kaisha Ltd | Aceite microbiano, procedimiento para fabricar aceite microbiano, aceite microbiano concentrado y procedimiento para fabricar aceite microbiano concentrado |
| CN105967998A (zh) * | 2016-05-06 | 2016-09-28 | 安庆市中创生物工程有限公司 | 纯度99%亚油酸的制备方法 |
| CN107698444A (zh) * | 2017-03-03 | 2018-02-16 | 四川森迪科技发展股份有限公司 | 一种从毛叶山桐子油饼中提取亚麻酸的方法 |
| CN110590545B (zh) * | 2019-09-11 | 2023-08-29 | 上海同田生物技术股份有限公司 | 一种完全分离油酸和亚油酸的方法 |
| US20210315851A1 (en) | 2020-04-03 | 2021-10-14 | Afimmune Limited | Compositions comprising 15-hepe and methods of treating or preventing hematologic disorders, and/or related diseases |
| CN113185398B (zh) * | 2021-05-17 | 2022-08-16 | 武汉轻工大学 | 一种苦瓜籽油中高含量共轭亚麻酸α-桐酸的富集方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2596344A (en) * | 1948-08-21 | 1952-05-13 | Shell Dev | Fractionation process |
| US2662879A (en) * | 1949-01-29 | 1953-12-15 | Shell Dev | Separation of geometrical isomers by urea complex formation |
| GB1240513A (en) * | 1968-09-13 | 1971-07-28 | Ono Pharmaceutical Co | Poly-unsaturated fatty acid ester composition and its preparation |
| FR2490631A1 (fr) * | 1980-09-24 | 1982-03-26 | Roussel Uclaf | Nouvelle composition lipidique utilisable en dietetique, reanimation et therapeutique |
| JPS57164196A (en) * | 1981-04-03 | 1982-10-08 | Nippon Oils & Fats Co Ltd | Concentration separation of highly unsaturated fatty acids |
| JPS57187397A (en) * | 1981-05-15 | 1982-11-18 | Nippon Suisan Kaisha Ltd | Manufacture of eicosapentaenoic acid or ester of same |
| ATE24266T1 (de) * | 1982-04-16 | 1987-01-15 | Nestle Sa | Lipidhaltige zusammensetzung fuer die orale, enterale oder parenterale ernaehrung. |
-
1984
- 1984-10-10 CH CH4858/84A patent/CH663951A5/fr not_active IP Right Cessation
-
1985
- 1985-09-04 AT AT85111161T patent/ATE33037T1/de not_active IP Right Cessation
- 1985-09-04 DE DE8585111161T patent/DE3561890D1/de not_active Expired
- 1985-09-04 EP EP85111161A patent/EP0178442B1/fr not_active Expired
- 1985-09-10 IL IL76349A patent/IL76349A/xx not_active IP Right Cessation
- 1985-09-11 AU AU47371/85A patent/AU580330B2/en not_active Ceased
- 1985-09-12 ZA ZA857008A patent/ZA857008B/xx unknown
- 1985-09-12 CA CA000490579A patent/CA1265156A/en not_active Expired - Fee Related
- 1985-10-03 NO NO853916A patent/NO163825C/no unknown
- 1985-10-08 GR GR852437A patent/GR852437B/el unknown
- 1985-10-08 DK DK458685A patent/DK164817C/da not_active IP Right Cessation
- 1985-10-09 JP JP60225941A patent/JP2657056B2/ja not_active Expired - Lifetime
- 1985-10-09 ES ES547701A patent/ES8604850A1/es not_active Expired
- 1985-10-09 NZ NZ213767A patent/NZ213767A/en unknown
- 1985-10-10 HU HU853932A patent/HU198171B/hu not_active IP Right Cessation
- 1985-10-10 FI FI853940A patent/FI81830C/fi not_active IP Right Cessation
-
1987
- 1987-02-27 US US07/018,778 patent/US4776984A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4776984A (en) | 1988-10-11 |
| NO853916L (no) | 1986-04-11 |
| ATE33037T1 (de) | 1988-04-15 |
| ES547701A0 (es) | 1986-03-01 |
| NZ213767A (en) | 1988-02-29 |
| IL76349A0 (en) | 1986-01-31 |
| DK164817B (da) | 1992-08-24 |
| DK458685D0 (da) | 1985-10-08 |
| DE3561890D1 (en) | 1988-04-21 |
| EP0178442A1 (fr) | 1986-04-23 |
| ES8604850A1 (es) | 1986-03-01 |
| CA1265156A (en) | 1990-01-30 |
| AU4737185A (en) | 1986-04-17 |
| EP0178442B1 (fr) | 1988-03-16 |
| FI81830C (fi) | 1990-12-10 |
| IL76349A (en) | 1989-07-31 |
| GR852437B (enExample) | 1986-02-10 |
| ZA857008B (en) | 1986-04-30 |
| NO163825C (no) | 1990-07-25 |
| AU580330B2 (en) | 1989-01-12 |
| DK164817C (da) | 1993-01-04 |
| CH663951A5 (fr) | 1988-01-29 |
| HUT43990A (en) | 1988-01-28 |
| FI81830B (fi) | 1990-08-31 |
| FI853940A0 (fi) | 1985-10-10 |
| FI853940L (fi) | 1986-04-11 |
| JPS6195095A (ja) | 1986-05-13 |
| NO163825B (no) | 1990-04-17 |
| JP2657056B2 (ja) | 1997-09-24 |
| DK458685A (da) | 1986-04-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HU90 | Patent valid on 900628 | ||
| HMM4 | Cancellation of final prot. due to non-payment of fee |