CH663951A5 - Procede d'enrichissement selectif en acides gras polyinsatures d'un melange contenant des acides gras fractions enrichies obtenues et compositions les contenant. - Google Patents

Procede d'enrichissement selectif en acides gras polyinsatures d'un melange contenant des acides gras fractions enrichies obtenues et compositions les contenant. Download PDF

Info

Publication number: CH663951A5
Authority: CH; Switzerland
Prior art keywords: fatty acids; mixture; urea; gamma; polyunsaturated fatty
Prior art date: 1984-10-10

Application number

CH4858/84A

Other languages

English (en)

French (fr)

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

1984-10-10

Publication date

1988-01-29

1984-10-10 Application filed by Nestle Sa filed Critical Nestle Sa

1984-10-10 Priority to CH4858/84A priority Critical patent/CH663951A5/fr

1985-09-04 Priority to DE8585111161T priority patent/DE3561890D1/de

1985-09-04 Priority to EP85111161A priority patent/EP0178442B1/fr

1985-09-04 Priority to AT85111161T priority patent/ATE33037T1/de

1985-09-10 Priority to IL76349A priority patent/IL76349A/xx

1985-09-11 Priority to AU47371/85A priority patent/AU580330B2/en

1985-09-12 Priority to ZA857008A priority patent/ZA857008B/xx

1985-09-12 Priority to CA000490579A priority patent/CA1265156A/en

1985-10-03 Priority to NO853916A priority patent/NO163825C/no

1985-10-08 Priority to DK458685A priority patent/DK164817C/da

1985-10-08 Priority to GR852437A priority patent/GR852437B/el

1985-10-09 Priority to JP60225941A priority patent/JP2657056B2/ja

1985-10-09 Priority to NZ213767A priority patent/NZ213767A/en

1985-10-09 Priority to ES547701A priority patent/ES8604850A1/es

1985-10-10 Priority to FI853940A priority patent/FI81830C/fi

1985-10-10 Priority to HU853932A priority patent/HU198171B/hu

1987-02-27 Priority to US07/018,778 priority patent/US4776984A/en

1988-01-29 Publication of CH663951A5 publication Critical patent/CH663951A5/fr

Links

239000000203 mixture Substances 0.000 title claims abstract description 57
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
235000020777 polyunsaturated fatty acids Nutrition 0.000 title claims abstract description 12
238000000034 method Methods 0.000 title claims description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims abstract description 24
239000004202 carbamide Substances 0.000 claims abstract description 24
235000020664 gamma-linolenic acid Nutrition 0.000 claims abstract description 21
VZCCETWTMQHEPK-UHFFFAOYSA-N gamma-Linolensaeure Natural products CCCCCC=CCC=CCC=CCCCCC(O)=O VZCCETWTMQHEPK-UHFFFAOYSA-N 0.000 claims abstract description 20
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 20
229960002733 gamolenic acid Drugs 0.000 claims abstract description 20
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 15
230000015572 biosynthetic process Effects 0.000 claims abstract description 5
239000012047 saturated solution Substances 0.000 claims abstract description 5
HOBAELRKJCKHQD-UHFFFAOYSA-N (8Z,11Z,14Z)-8,11,14-eicosatrienoic acid Natural products CCCCCC=CCC=CCC=CCCCCCCC(O)=O HOBAELRKJCKHQD-UHFFFAOYSA-N 0.000 claims abstract description 4
235000021298 Dihomo-γ-linolenic acid Nutrition 0.000 claims 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 claims abstract description 4
238000003786 synthesis reaction Methods 0.000 claims abstract description 4
238000004128 high performance liquid chromatography Methods 0.000 claims abstract description 3
239000012071 phase Substances 0.000 claims description 23
239000000243 solution Substances 0.000 claims description 14
239000007791 liquid phase Substances 0.000 claims description 8
235000001466 Ribes nigrum Nutrition 0.000 claims description 7
241001312569 Ribes nigrum Species 0.000 claims description 7
238000007127 saponification reaction Methods 0.000 claims description 7
235000016954 Ribes hudsonianum Nutrition 0.000 claims description 4
235000013399 edible fruits Nutrition 0.000 claims description 4
235000011483 Ribes Nutrition 0.000 claims description 3
241000220483 Ribes Species 0.000 claims description 3
210000000614 rib Anatomy 0.000 claims description 3
235000016709 nutrition Nutrition 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
238000002360 preparation method Methods 0.000 claims 1
239000003814 drug Substances 0.000 abstract description 3
239000007858 starting material Substances 0.000 abstract description 3
230000000050 nutritive effect Effects 0.000 abstract description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 30
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 13
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
238000003756 stirring Methods 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000003921 oil Substances 0.000 description 9
235000019198 oils Nutrition 0.000 description 9
235000020661 alpha-linolenic acid Nutrition 0.000 description 7
238000010908 decantation Methods 0.000 description 6
238000005194 fractionation Methods 0.000 description 6
229960004488 linolenic acid Drugs 0.000 description 6
239000002253 acid Substances 0.000 description 5
239000002994 raw material Substances 0.000 description 5
229940094199 black currant oil Drugs 0.000 description 4
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 3
150000007513 acids Chemical class 0.000 description 3
238000005119 centrifugation Methods 0.000 description 3
238000004817 gas chromatography 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
JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 3
235000015112 vegetable and seed oil Nutrition 0.000 description 3
239000003109 Disodium ethylene diamine tetraacetate Substances 0.000 description 2
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 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
239000007864 aqueous solution Substances 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
230000000052 comparative effect Effects 0.000 description 2
235000019301 disodium ethylene diamine tetraacetate Nutrition 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
239000007788 liquid Substances 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
238000004237 preparative chromatography Methods 0.000 description 2
239000000047 product Substances 0.000 description 2
235000003441 saturated fatty acids Nutrition 0.000 description 2
150000004671 saturated fatty acids Chemical class 0.000 description 2
238000000926 separation method Methods 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
150000003626 triacylglycerols Chemical class 0.000 description 2
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
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 1
239000011786 L-ascorbyl-6-palmitate Substances 0.000 description 1
OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
241000219925 Oenothera Species 0.000 description 1
235000001537 Ribes X gardonianum Nutrition 0.000 description 1
235000001535 Ribes X utile Nutrition 0.000 description 1
235000002357 Ribes grossularia Nutrition 0.000 description 1
244000171263 Ribes grossularia Species 0.000 description 1
235000016919 Ribes petraeum Nutrition 0.000 description 1
244000281247 Ribes rubrum Species 0.000 description 1
235000002355 Ribes spicatum Nutrition 0.000 description 1
241000269821 Scombridae 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
230000003078 antioxidant effect Effects 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
235000010385 ascorbyl palmitate Nutrition 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000004587 chromatography analysis 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
230000000378 dietary effect Effects 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
235000008524 evening primrose extract Nutrition 0.000 description 1
229940089020 evening primrose oil Drugs 0.000 description 1
239000010475 evening primrose oil Substances 0.000 description 1
235000019197 fats Nutrition 0.000 description 1
235000021588 free fatty acids Nutrition 0.000 description 1
229940098330 gamma linoleic acid Drugs 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-M hexadecanoate Chemical compound CCCCCCCCCCCCCCCC([O-])=O IPCSVZSSVZVIGE-UHFFFAOYSA-M 0.000 description 1
235000020778 linoleic acid Nutrition 0.000 description 1
OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
235000020640 mackerel Nutrition 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
230000003472 neutralizing effect Effects 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
235000010388 propyl gallate Nutrition 0.000 description 1
239000000473 propyl gallate Substances 0.000 description 1
229940075579 propyl gallate Drugs 0.000 description 1
230000006798 recombination Effects 0.000 description 1
238000005215 recombination Methods 0.000 description 1
238000007670 refining Methods 0.000 description 1
238000004007 reversed phase HPLC Methods 0.000 description 1
229920006395 saturated elastomer Polymers 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
UEUXEKPTXMALOB-UHFFFAOYSA-J tetrasodium;2-[2-[bis(carboxylatomethyl)amino]ethyl-(carboxylatomethyl)amino]acetate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)CN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O UEUXEKPTXMALOB-UHFFFAOYSA-J 0.000 description 1
235000021122 unsaturated fatty acids Nutrition 0.000 description 1
150000004670 unsaturated fatty acids Chemical class 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
238000005406 washing Methods 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)

CH4858/84A 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. CH663951A5 (fr)

Priority Applications (17)

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.
DE8585111161T DE3561890D1 (en)	1984-10-10	1985-09-04	Process for the selective enrichment of a delta-6 and delta-9 fatty acids containing mixture with delta-6 polyunsaturated fatty acids, the enriched fractions thus obtained and their use
EP85111161A EP0178442B1 (fr)	1984-10-10	1985-09-04	Procédé d'enrichissement sélectif en acides gras polyinsaturés delta-6 d'un mélange contenant des acides gras delta-6 et delta-9, fractions enrichies obtenues et leur utilisation
AT85111161T ATE33037T1 (de)	1984-10-10	1985-09-04	Selektives anreicherungsverfahren an delta-6 polyungesaettigten fettsaeuren der delta-6 und delta-9 enthaltenden fettsaeuremischung, so erhaltene angereicherte fraktionen und ihre verwendung.
IL76349A IL76349A (en)	1984-10-10	1985-09-10	Process for the selective enrichment of a delta-6 and delta-9 fatty acid containing mixture with delta-6 polyunsaturated fatty acids
AU47371/85A AU580330B2 (en)	1984-10-10	1985-09-11	Process for the enrichment with ``6 fatty acids of a mixture of fatty acids
ZA857008A ZA857008B (en)	1984-10-10	1985-09-12	Process for the enrichment with delta6 fatty acids of a mixture of fatty acids
CA000490579A CA1265156A (en)	1984-10-10	1985-09-12	Process for the enrichment with .delta.6 fatty acids of a mixture of fatty acids
NO853916A NO163825C (no)	1984-10-10	1985-10-03	Fremgangsmaate for selektiv anrikning av en fettsyreblanding paa delta6-fettsyrer.
DK458685A DK164817C (da)	1984-10-10	1985-10-08	Fremgangsmaade til berigelse af fedtsyreblandinger med delta6-fedtsyrer
GR852437A GR852437B (2)	1984-10-10	1985-10-08
JP60225941A JP2657056B2 (ja)	1984-10-10	1985-10-09	γ‐リノレン酸の豊富化方法
NZ213767A NZ213767A (en)	1984-10-10	1985-10-09	Process for the enrichment with #w#6 fatty acids of a mixture of fatty acids
ES547701A ES8604850A1 (es)	1984-10-10	1985-10-09	Procedimiento para enriquecer selectivamente en acidos gra- sos poliinsaturados delta-6 un producto que contiene acidos grasos delta-6 y delta-9
FI853940A FI81830C (fi)	1984-10-10	1985-10-10	Foerfarande foer att berika en blandning av fettsyror med 6-fettsyror.
HU853932A HU198171B (en)	1984-10-10	1985-10-10	Process for concentrating delta 6 polyinsaturated fatty acids in the mixture of polyinsaturated fatty acids
US07/018,778 US4776984A (en)	1984-10-10	1987-02-27	Process for the enrichment with Δ6 fatty acids of a mixture of fatty acids

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 (1)

Publication Number	Publication Date
CH663951A5 true CH663951A5 (fr)	1988-01-29

Family

ID=4283774

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
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.

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)

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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
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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
HU198171B (en)	1989-08-28
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
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
2001-06-15	PL	Patent ceased

Publication	Publication Date	Title
EP0178442B1 (fr)	1988-03-16	Procédé d'enrichissement sélectif en acides gras polyinsaturés delta-6 d'un mélange contenant des acides gras delta-6 et delta-9, fractions enrichies obtenues et leur utilisation
EP0271747B1 (fr)	1994-08-10	Procédé de fractionnement en continu d'un mélange d'acides gras
EP0682006B1 (fr)	1999-04-07	Procédé de préparation d'un concentrat d'esters d'acides gras polyinsaturés
EP3789476B1 (en)	2024-11-27	Method for producing very long chain polyunsaturated fatty acids from natural oils and nutraceutical composition thereof.
EP2659780B2 (en)	2021-06-23	Omega 3 concentrate
JPH0159318B2 (2)	1989-12-15
KR100972703B1 (ko)	2010-07-27	분리 기술의 개선 방법
WO1994021764A1 (fr)	1994-09-29	Matieres insaponifiables d'origine vegetale et compositions cosmetiques les contenant
US5243046A (en)	1993-09-07	Process for the continuous fractionation of a mixture of fatty acids
EP0137862B1 (fr)	1987-09-16	Procédé de préparation de corps gras
GB2185976A (en)	1987-08-05	Process for the enrichment with ???6 fatty acids of a mixture of fatty acids
EP2736356A2 (fr)	2014-06-04	Extraction liquide/liquide avec un solvant comprenant au moins 5 atomes de carbone et 1 ou 2 atomes d'oxygene