JP2657056B2 - γ‐リノレン酸の豊富化方法 - Google Patents
γ‐リノレン酸の豊富化方法Info
- Publication number
- JP2657056B2 JP2657056B2 JP60225941A JP22594185A JP2657056B2 JP 2657056 B2 JP2657056 B2 JP 2657056B2 JP 60225941 A JP60225941 A JP 60225941A JP 22594185 A JP22594185 A JP 22594185A JP 2657056 B2 JP2657056 B2 JP 2657056B2
- Authority
- JP
- Japan
- Prior art keywords
- fatty acids
- mixture
- linolenic acid
- urea
- polyunsaturated fatty
- 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.)
- Expired - Lifetime
Links
- 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 title claims abstract description 25
- 239000000203 mixture Substances 0.000 claims abstract description 58
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 37
- 239000000194 fatty acid Substances 0.000 claims abstract description 37
- 229930195729 fatty acid Natural products 0.000 claims abstract description 37
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 30
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 26
- 239000004202 carbamide Substances 0.000 claims abstract description 26
- VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims abstract description 23
- 235000020664 gamma-linolenic acid Nutrition 0.000 claims abstract description 23
- 229960002733 gamolenic acid Drugs 0.000 claims abstract description 23
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 claims abstract description 19
- 239000012047 saturated solution Substances 0.000 claims abstract description 3
- 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 claims description 20
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 13
- 229960004488 linolenic acid Drugs 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 13
- 239000007791 liquid phase Substances 0.000 claims description 9
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 7
- 235000001537 Ribes X gardonianum Nutrition 0.000 claims description 3
- 235000001535 Ribes X utile Nutrition 0.000 claims description 3
- 235000016919 Ribes petraeum Nutrition 0.000 claims description 3
- 244000281247 Ribes rubrum Species 0.000 claims description 3
- 235000002355 Ribes spicatum Nutrition 0.000 claims description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 3
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 3
- 238000004007 reversed phase HPLC Methods 0.000 claims 2
- 235000011483 Ribes Nutrition 0.000 claims 1
- 241000220483 Ribes Species 0.000 claims 1
- 210000000614 rib Anatomy 0.000 claims 1
- 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 7
- 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 4
- 235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 abstract description 4
- 230000015572 biosynthetic process Effects 0.000 abstract description 4
- 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 4
- 238000004128 high performance liquid chromatography Methods 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 239000003814 drug Substances 0.000 abstract description 2
- 230000000050 nutritive effect Effects 0.000 abstract 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
- 239000012071 phase Substances 0.000 description 20
- 239000000243 solution Substances 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 9
- 235000019198 oils Nutrition 0.000 description 9
- 238000003756 stirring Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010908 decantation Methods 0.000 description 6
- 238000005194 fractionation Methods 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 description 4
- 235000001466 Ribes nigrum Nutrition 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 235000013399 edible fruits Nutrition 0.000 description 4
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 3
- 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 3
- 235000016954 Ribes hudsonianum Nutrition 0.000 description 3
- 240000001890 Ribes hudsonianum Species 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 229940094199 black currant oil Drugs 0.000 description 3
- 235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000007790 solid phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000011877 solvent mixture Substances 0.000 description 3
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 description 2
- 235000000072 L-ascorbyl-6-palmitate Nutrition 0.000 description 2
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 2
- 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
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- 235000020778 linoleic acid Nutrition 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- DWPVTYBWOACIHU-PZVVRBJASA-N (6e,8e,11e,14e)-icosa-6,8,11,14-tetraenoic acid Chemical compound CCCCC\C=C\C\C=C\C\C=C\C=C\CCCCC(O)=O DWPVTYBWOACIHU-PZVVRBJASA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-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
- 235000004496 Oenothera biennis Nutrition 0.000 description 1
- 241001312569 Ribes nigrum Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000004492 methyl ester group Chemical group 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 235000010388 propyl gallate Nutrition 0.000 description 1
- 239000000473 propyl gallate Substances 0.000 description 1
- 229940075579 propyl gallate Drugs 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 239000003352 sequestering agent Substances 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
- 239000000725 suspension Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- DTOSIQBPPRVQHS-UHFFFAOYSA-N α-Linolenic acid Chemical compound CCC=CCC=CCC=CCCCCCCCC(O)=O DTOSIQBPPRVQHS-UHFFFAOYSA-N 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)
- Bipolar Transistors (AREA)
- Control Of El Displays (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
Applications Claiming Priority (2)
| 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. |
| CH4858/84-6 | 1984-10-10 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6195095A JPS6195095A (ja) | 1986-05-13 |
| JP2657056B2 true JP2657056B2 (ja) | 1997-09-24 |
Family
ID=4283774
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60225941A Expired - Lifetime JP2657056B2 (ja) | 1984-10-10 | 1985-10-09 | γ‐リノレン酸の豊富化方法 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4776984A (cg-RX-API-DMAC7.html) |
| EP (1) | EP0178442B1 (cg-RX-API-DMAC7.html) |
| JP (1) | JP2657056B2 (cg-RX-API-DMAC7.html) |
| AT (1) | ATE33037T1 (cg-RX-API-DMAC7.html) |
| AU (1) | AU580330B2 (cg-RX-API-DMAC7.html) |
| CA (1) | CA1265156A (cg-RX-API-DMAC7.html) |
| CH (1) | CH663951A5 (cg-RX-API-DMAC7.html) |
| DE (1) | DE3561890D1 (cg-RX-API-DMAC7.html) |
| DK (1) | DK164817C (cg-RX-API-DMAC7.html) |
| ES (1) | ES8604850A1 (cg-RX-API-DMAC7.html) |
| FI (1) | FI81830C (cg-RX-API-DMAC7.html) |
| GR (1) | GR852437B (cg-RX-API-DMAC7.html) |
| HU (1) | HU198171B (cg-RX-API-DMAC7.html) |
| IL (1) | IL76349A (cg-RX-API-DMAC7.html) |
| NO (1) | NO163825C (cg-RX-API-DMAC7.html) |
| NZ (1) | NZ213767A (cg-RX-API-DMAC7.html) |
| ZA (1) | ZA857008B (cg-RX-API-DMAC7.html) |
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 (cg-RX-API-DMAC7.html) * | 1989-05-22 | 1991-08-15 | Nestle Sa | |
| DK0682006T3 (da) * | 1994-05-09 | 1999-10-18 | Nestle Sa | Fremgangsmåde til fremstilling af et koncentrat af estere af flerumættede fede syrer |
| ATE178087T1 (de) * | 1995-05-04 | 1999-04-15 | Nestle Sa | Verfahren zur fraktionierung von fettsäuren |
| 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 |
| 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 |
| US6579551B1 (en) | 1998-05-21 | 2003-06-17 | Beech-Nut Nutrition Corporation | Baby-food compositions containing egg yolk and methods therefor |
| US7141266B2 (en) * | 1998-05-21 | 2006-11-28 | Beech-Nut Nutrition Corporation | Baby-food compositions enhancing visual acuity and methods therefor |
| US6149964A (en) * | 1998-05-21 | 2000-11-21 | Beech-Nut Nutrition Corporation | Egg yolk-containing baby food compositions and methods therefor |
| WO2001051598A1 (en) | 2000-01-11 | 2001-07-19 | Monsanto Technology Llc | 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 |
| JP2004536059A (ja) * | 2001-05-14 | 2004-12-02 | マーテック バイオサイエンシズ ボールダー コーポレーション | 微生物、遺伝的に改変された植物種子および海洋生物由来のω−３および／またはω−６高度不飽和脂肪酸を含有する極性脂質の豊富な画分の生成および使用 |
| WO2002092073A1 (en) * | 2001-05-14 | 2002-11-21 | Martek Biosciences Corporation | Production and use of a polar lipid-rich fraction containing stearidonic acid and gamma linolenic acid from plant seeds and microbes |
| PT2277551E (pt) | 2002-09-06 | 2013-08-22 | Cerulean Pharma Inc | Polímeros à base de ciclodextrina para a administração de medicamentos ligados por ligação covalente |
| 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 |
| DK1656449T3 (da) | 2003-08-21 | 2009-06-02 | Monsanto Technology Llc | Fedtsyredesaturaser fra primula |
| ES2541537T3 (es) | 2004-04-16 | 2015-07-21 | Monsanto Technology, Llc | Expresión de desaturasas de ácido graso en maíz |
| KR100539357B1 (ko) * | 2005-04-11 | 2005-12-28 | 동부한농화학 주식회사 | 불포화 지방산의 제조방법 |
| US8003813B2 (en) * | 2006-06-27 | 2011-08-23 | Pos Pilot Plant Corporation | Process for separating saturated and unsaturated fatty acids |
| 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 |
| 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 |
| BR112014013098A2 (pt) * | 2011-11-29 | 2017-06-13 | Dignity Sciences Ltd | composições compreendendo ácidos graxos que têm 20 carbonos e métodos de produção e uso dos mesmos |
| US20140094432A1 (en) | 2012-10-02 | 2014-04-03 | Cerulean Pharma Inc. | Methods and systems for polymer precipitation and generation of particles |
| PL3101138T3 (pl) * | 2013-12-04 | 2021-10-25 | Nippon Suisan Kaisha, Ltd. | Olej drobnoustrojowy, sposób wytwarzania oleju drobnoustrojowego, stężony olej drobnoustrojowy oraz sposób wytwarzania stężonego oleju drobnoustrojowego |
| 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 |
| CN117209376A (zh) * | 2019-09-11 | 2023-12-12 | 上海同田生物技术有限公司 | 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 |
| DE3368377D1 (en) * | 1982-04-16 | 1987-01-29 | Nestle Sa | Lipid composition for oral, enteral or parenteral feeding |
-
1984
- 1984-10-10 CH CH4858/84A patent/CH663951A5/fr not_active IP Right Cessation
-
1985
- 1985-09-04 DE DE8585111161T patent/DE3561890D1/de not_active Expired
- 1985-09-04 AT AT85111161T patent/ATE33037T1/de not_active IP Right Cessation
- 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 CA CA000490579A patent/CA1265156A/en not_active Expired - Fee Related
- 1985-09-12 ZA ZA857008A patent/ZA857008B/xx unknown
- 1985-10-03 NO NO853916A patent/NO163825C/no unknown
- 1985-10-08 DK DK458685A patent/DK164817C/da not_active IP Right Cessation
- 1985-10-08 GR GR852437A patent/GR852437B/el unknown
- 1985-10-09 JP JP60225941A patent/JP2657056B2/ja not_active Expired - Lifetime
- 1985-10-09 NZ NZ213767A patent/NZ213767A/en unknown
- 1985-10-09 ES ES547701A patent/ES8604850A1/es not_active Expired
- 1985-10-10 FI FI853940A patent/FI81830C/fi not_active IP Right Cessation
- 1985-10-10 HU HU853932A patent/HU198171B/hu 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 |
|---|---|
| FI853940L (fi) | 1986-04-11 |
| EP0178442A1 (fr) | 1986-04-23 |
| FI853940A0 (fi) | 1985-10-10 |
| DK164817B (da) | 1992-08-24 |
| IL76349A (en) | 1989-07-31 |
| HUT43990A (en) | 1988-01-28 |
| DE3561890D1 (en) | 1988-04-21 |
| FI81830C (fi) | 1990-12-10 |
| DK458685D0 (da) | 1985-10-08 |
| GR852437B (cg-RX-API-DMAC7.html) | 1986-02-10 |
| US4776984A (en) | 1988-10-11 |
| ATE33037T1 (de) | 1988-04-15 |
| AU580330B2 (en) | 1989-01-12 |
| FI81830B (fi) | 1990-08-31 |
| IL76349A0 (en) | 1986-01-31 |
| NO853916L (no) | 1986-04-11 |
| CA1265156A (en) | 1990-01-30 |
| DK164817C (da) | 1993-01-04 |
| EP0178442B1 (fr) | 1988-03-16 |
| HU198171B (en) | 1989-08-28 |
| ZA857008B (en) | 1986-04-30 |
| AU4737185A (en) | 1986-04-17 |
| JPS6195095A (ja) | 1986-05-13 |
| NO163825C (no) | 1990-07-25 |
| NO163825B (no) | 1990-04-17 |
| CH663951A5 (fr) | 1988-01-29 |
| ES8604850A1 (es) | 1986-03-01 |
| ES547701A0 (es) | 1986-03-01 |
| NZ213767A (en) | 1988-02-29 |
| DK458685A (da) | 1986-04-11 |
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