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 PDF

Info

Publication number: HU198171B
Authority: HU; Hungary
Prior art keywords: fatty acids; mixture; acid; urea; linolenic acid
Prior art date: 1984-10-10

Application number

HU853932A

Other languages

English (en)

Hungarian (hu)

Other versions

HUT43990A (en

Inventor

Helmut Traitler

Alfred Studer

Original Assignee

Nestle Sa

Priority date (The priority date 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 date listed.)

1984-10-10

Filing date

1985-10-10

Publication date

1989-08-28

1985-10-10 Application filed by Nestle Sa filed Critical Nestle Sa

1988-01-28 Publication of HUT43990A publication Critical patent/HUT43990A/hu

1989-08-28 Publication of HU198171B publication Critical patent/HU198171B/hu

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)
Life Sciences & Earth Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material 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)

HU853932A 1984-10-10 1985-10-10 Process for concentrating delta 6 polyinsaturated fatty acids in the mixture of polyinsaturated fatty acids HU198171B (en)

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 (2)
EP (1)	EP0178442B1 (2)
JP (1)	JP2657056B2 (2)
AT (1)	ATE33037T1 (2)
AU (1)	AU580330B2 (2)
CA (1)	CA1265156A (2)
CH (1)	CH663951A5 (2)
DE (1)	DE3561890D1 (2)
DK (1)	DK164817C (2)
ES (1)	ES8604850A1 (2)
FI (1)	FI81830C (2)
GR (1)	GR852437B (2)
HU (1)	HU198171B (2)
IL (1)	IL76349A (2)
NO (1)	NO163825C (2)
NZ (1)	NZ213767A (2)
ZA (1)	ZA857008B (2)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
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
CH669208A5 (fr) *	1986-12-17	1989-02-28	Nestle Sa	Procede de fractionnement en continu d'un melange d'acides gras.
US5243046A (en) *	1986-12-17	1993-09-07	Nestec S.A.	Process for the continuous fractionation of a mixture of fatty acids
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 (2) *	1989-05-22	1991-08-15	Nestle Sa
DE69417726T2 (de) *	1994-05-09	1999-08-19	Societe Des Produits Nestle S.A.	Verfahren zur Herstellung eines Konzentrates von Estern von mehrfach ungesättigten Fettsäuren
DE69508558T2 (de) *	1995-05-04	1999-08-26	Societe Des Produits Nestle S.A.	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
US6149964A (en) *	1998-05-21	2000-11-21	Beech-Nut Nutrition Corporation	Egg yolk-containing baby food compositions and methods therefor
US7141266B2 (en) *	1998-05-21	2006-11-28	Beech-Nut Nutrition Corporation	Baby-food compositions enhancing visual acuity and methods therefor
US6579551B1 (en)	1998-05-21	2003-06-17	Beech-Nut Nutrition Corporation	Baby-food compositions containing egg yolk 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
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
EP2275101A1 (en) *	2001-05-14	2011-01-19	Martek Biosciences Corporation	Polar lipid-rich fraction containing stearidonic acid and gamma linolenic acid from plant seeds and microbes, and its uses
AU2002309856B2 (en) *	2001-05-14	2008-10-23	Dsm Ip Assets B.V.	Production and use of a polar lipid-rich fraction containing omega-3 and/or omega-6 highly unsaturated fatty acids from microbes, genetically modified plant seeds and marine organisms
EP2277551B1 (en)	2002-09-06	2013-05-08	Cerulean Pharma Inc.	Cyclodextrin-based polymers for delivering the therapeutic agents covalently bound thereto
WO2004032862A2 (en) *	2002-10-09	2004-04-22	Insert Therapeutics, Inc.	Cyclodextrin-based materials, compositions and uses related thereto
CA2436650A1 (en) *	2003-08-06	2005-02-06	Naturia Inc.	Conjugated linolenic acid (clnatm) compositions: synthesis, purification and uses
ATE430802T1 (de) *	2003-08-21	2009-05-15	Monsanto Technology Llc	Fettsäuredesaturasen aus primula
CN1968688A (zh)	2004-04-16	2007-05-23	孟山都技术有限公司	脂肪酸去饱和酶在玉米中的表达
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
WO2011056982A1 (en)	2009-11-05	2011-05-12	Purdue Research Foundation	Method of lowering the cloud point of fatty acid esters
KR20140113921A (ko) *	2011-11-29	2014-09-25	디그너티 사이언스 리미티드	20-탄소 지방산을 포함하는 조성물 및 이를 제조 및 사용하는 방법
US20140094432A1 (en)	2012-10-02	2014-04-03	Cerulean Pharma Inc.	Methods and systems for polymer precipitation and generation of particles
HUE055277T2 (hu)	2013-12-04	2021-11-29	Nippon Suisan Kaisha Ltd	Dihomo-gamma-linolénsavat tartalmazó mikrobális olaj és dihomo-gamma-linolénsavat tartalmazó mikrobális biomassza
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)

* Cited by examiner, † Cited by third party
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 EP EP85111161A patent/EP0178442B1/fr not_active Expired
- 1985-09-04 DE DE8585111161T patent/DE3561890D1/de not_active Expired
- 1985-09-04 AT AT85111161T patent/ATE33037T1/de not_active IP Right Cessation
- 1985-09-10 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 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
AU580330B2 (en)	1989-01-12
DE3561890D1 (en)	1988-04-21
NO163825C (no)	1990-07-25
US4776984A (en)	1988-10-11
HUT43990A (en)	1988-01-28
ATE33037T1 (de)	1988-04-15
FI81830B (fi)	1990-08-31
NZ213767A (en)	1988-02-29
JP2657056B2 (ja)	1997-09-24
EP0178442A1 (fr)	1986-04-23
JPS6195095A (ja)	1986-05-13
FI853940L (fi)	1986-04-11
IL76349A0 (en)	1986-01-31
NO163825B (no)	1990-04-17
ES547701A0 (es)	1986-03-01
AU4737185A (en)	1986-04-17
ZA857008B (en)	1986-04-30
CH663951A5 (fr)	1988-01-29
CA1265156A (en)	1990-01-30
FI81830C (fi)	1990-12-10
DK164817C (da)	1993-01-04
DK164817B (da)	1992-08-24
IL76349A (en)	1989-07-31
ES8604850A1 (es)	1986-03-01
NO853916L (no)	1986-04-11
DK458685D0 (da)	1985-10-08
GR852437B (2)	1986-02-10
EP0178442B1 (fr)	1988-03-16
DK458685A (da)	1986-04-11
FI853940A0 (fi)	1985-10-10

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
2000-07-28	HMM4	Cancellation of final prot. due to non-payment of fee

Publication	Publication Date	Title
US4776984A (en)	1988-10-11	Process for the enrichment with Δ6 fatty acids of a mixture of fatty acids
US5679809A (en)	1997-10-21	Concentrate of polyunsaturated fatty acid ethyl esters and preparation thereof
AU604802B2 (en)	1991-01-03	A process for the continuous fractionation of a mixture of fatty acids
US20090221705A1 (en)	2009-09-03	Omega 3
HU185359B (en)	1985-01-28	Process for producing nutritive compositions containing fats and for producing fats utilizaale as active agents
JPS60115522A (ja)	1985-06-22	血中のコレステロ−ル及びトリグリセリドのレベルを低下させるための複合脂肪酸組成物
JP2013151689A (ja)	2013-08-08	Ｄｈａを含有する脂肪酸組成物を製造する方法
KR102639143B1 (ko)	2024-02-21	초장쇄 지방산 조성물
TWI778199B (zh)	2022-09-21	Ｄｈａ富集的多不飽和脂肪酸組合物
JPH0159318B2 (2)	1989-12-15
TWI774898B (zh)	2022-08-21	基於植物之脂質組合物、包含該脂質組合物之油漆或清漆，及用於產生該脂質組合物的方法
TWI774896B (zh)	2022-08-21	基於植物之脂質組合物及其用途、包含該脂質組合物之類藥劑營養品組合物及食品以及產生該脂質組合物脂之方法
TWI774897B (zh)	2022-08-21	基於植物之脂質組合物及用於產生該組合物之方法
US4510093A (en)	1985-04-09	Synthetic liquid wax esters
JPH0761954B2 (ja)	1995-07-05	コレステロール低下または上昇抑制剤
WO1996031457A1 (en)	1996-10-10	Triglycerides
Gustafson et al.	2013	Pycnanthus angolensis: bioactive compounds and medicinal applications
US7740885B2 (en)	2010-06-22	Nutraceutical and pharmaceutical compositions and their uses
GB2185976A (en)	1987-08-05	Process for the enrichment with ???6 fatty acids of a mixture of fatty acids