JP2006517237A5 - - Google Patents
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- Publication number
- JP2006517237A5 JP2006517237A5 JP2004539384A JP2004539384A JP2006517237A5 JP 2006517237 A5 JP2006517237 A5 JP 2006517237A5 JP 2004539384 A JP2004539384 A JP 2004539384A JP 2004539384 A JP2004539384 A JP 2004539384A JP 2006517237 A5 JP2006517237 A5 JP 2006517237A5
- Authority
- JP
- Japan
- Prior art keywords
- linoleic acid
- conjugated linoleic
- composition
- acid
- conjugated
- 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.)
- Withdrawn
Links
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 85
- 229940108924 conjugated linoleic acid Drugs 0.000 claims description 78
- 239000000203 mixture Substances 0.000 claims description 78
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 claims description 72
- 239000002253 acid Substances 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 33
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
- 239000003921 oil Substances 0.000 claims description 15
- 235000019198 oils Nutrition 0.000 claims description 15
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 14
- 229930195729 fatty acid Natural products 0.000 claims description 14
- 239000000194 fatty acid Substances 0.000 claims description 14
- 150000004665 fatty acids Chemical class 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000012071 phase Substances 0.000 claims description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- -1 conjugated linoleic acid ester Chemical class 0.000 claims description 7
- 235000020778 linoleic acid Nutrition 0.000 claims description 7
- 235000019485 Safflower oil Nutrition 0.000 claims description 4
- 235000019486 Sunflower oil Nutrition 0.000 claims description 4
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 claims description 4
- 239000008346 aqueous phase Substances 0.000 claims description 4
- 239000002285 corn oil Substances 0.000 claims description 4
- 235000005687 corn oil Nutrition 0.000 claims description 4
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 claims description 4
- 239000003813 safflower oil Substances 0.000 claims description 4
- 235000005713 safflower oil Nutrition 0.000 claims description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 4
- 239000002600 sunflower oil Substances 0.000 claims description 4
- 230000000593 degrading effect Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 14
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims 6
- 239000002775 capsule Substances 0.000 claims 5
- 235000013305 food Nutrition 0.000 claims 5
- 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 claims 3
- 239000003513 alkali Substances 0.000 claims 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000005119 centrifugation Methods 0.000 claims 1
- 238000000926 separation method Methods 0.000 claims 1
- 230000001268 conjugating effect Effects 0.000 description 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/253,216 US6743931B2 (en) | 2002-09-24 | 2002-09-24 | Conjugated linoleic acid compositions |
| PCT/IB2003/004897 WO2004029186A2 (en) | 2002-09-24 | 2003-09-24 | Conjugated linoleic acid compositions |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011102764A Division JP2011190451A (ja) | 2002-09-24 | 2011-05-02 | 共役リノール酸組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006517237A JP2006517237A (ja) | 2006-07-20 |
| JP2006517237A5 true JP2006517237A5 (enExample) | 2010-10-21 |
Family
ID=31993129
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004539384A Withdrawn JP2006517237A (ja) | 2002-09-24 | 2003-09-24 | 共役リノール酸組成物 |
| JP2011102764A Withdrawn JP2011190451A (ja) | 2002-09-24 | 2011-05-02 | 共役リノール酸組成物 |
| JP2014075877A Pending JP2014159580A (ja) | 2002-09-24 | 2014-04-02 | 共役リノール酸組成物 |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011102764A Withdrawn JP2011190451A (ja) | 2002-09-24 | 2011-05-02 | 共役リノール酸組成物 |
| JP2014075877A Pending JP2014159580A (ja) | 2002-09-24 | 2014-04-02 | 共役リノール酸組成物 |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US6743931B2 (enExample) |
| EP (1) | EP1546295B1 (enExample) |
| JP (3) | JP2006517237A (enExample) |
| AU (1) | AU2003274548B2 (enExample) |
| CA (1) | CA2499138C (enExample) |
| DK (1) | DK1546295T3 (enExample) |
| ES (1) | ES2551680T3 (enExample) |
| NO (1) | NO333298B1 (enExample) |
| WO (1) | WO2004029186A2 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6743931B2 (en) * | 2002-09-24 | 2004-06-01 | Natural Asa | Conjugated linoleic acid compositions |
| DE10259157A1 (de) * | 2002-12-18 | 2004-07-01 | Cognis Deutschland Gmbh & Co. Kg | Verfahren zur Herstellung von konjugierter Linolsäure |
| US6897327B2 (en) * | 2003-05-08 | 2005-05-24 | Stepan Company | Manufacture of conjugated linoleic salts and acids |
| US7193096B2 (en) * | 2003-07-01 | 2007-03-20 | Loders Croklaan Usa Llc | Process for producing a conjugated di- or poly-unsaturated fatty acid of 12 to 24 carbon atoms or salt or ester thereof |
| EP1696873B1 (en) * | 2003-12-23 | 2017-06-21 | Stepan Company | Production and purification of esters of conjugated linoleic acids |
| US20050215641A1 (en) * | 2004-03-10 | 2005-09-29 | Asgeir Saebo | Compositions comprising reverse isomers of conjugated linoleic acid |
| US7767713B2 (en) * | 2004-08-05 | 2010-08-03 | Palo Alto Investors | Linoleic acid active agents for enhancing probability of becoming pregnant |
| US20060051462A1 (en) * | 2004-09-03 | 2006-03-09 | Wang Jimmy X | Self emulsifying compositions for delivering lipophilic coenzyme Q10 and other dietary ingredients |
| US20070049763A1 (en) * | 2005-08-23 | 2007-03-01 | Reaney Martin J | Methods for preparation and use of strong base catalysts |
| EP1957063B1 (en) * | 2005-12-05 | 2010-08-25 | Stepan Company | Process for preparing conjugated linoleic acid and derivatives thereof from ricinoleic acid |
| BRPI0810127A2 (pt) * | 2007-04-24 | 2014-09-23 | Lipid Nutrition Bv | Iogurte, processo para produzir o iogurte, e, uso de um iogurte |
| ES2430200T3 (es) * | 2007-10-29 | 2013-11-19 | Stepan Specialty Products, Llc | Composición de aderezo |
| CN102229527B (zh) | 2009-12-14 | 2016-05-04 | 脂质营养品有限公司 | 工艺方法 |
| US8809560B2 (en) | 2011-05-17 | 2014-08-19 | Board Of Trustees Of The University Of Arkansas | Trans-, trans-conjugated linoleic acid compositions and use thereof |
| US9062276B2 (en) | 2012-12-03 | 2015-06-23 | Board Of Trustees Of The University Of Arkansas | Conjugated linoleic acid rich vegetable oil production from linoleic rich oils by heterogeneous catalysis |
| AU2014228387B2 (en) | 2013-03-11 | 2016-09-01 | Sciadonics, Inc. | Lipid compositions containing bioactive fatty acids |
| US9752099B2 (en) | 2014-12-05 | 2017-09-05 | Board Of Trustees Of The University Of Arkansas | Conjugated linoleic acid rich vegetable oil production using heterogeneous catalysis |
| CN104672088A (zh) * | 2015-02-12 | 2015-06-03 | 湖北华龙生物制药有限公司 | 一种由乌桕梓油制备共轭亚油酸乙酯的方法 |
| CN109984292A (zh) * | 2019-04-16 | 2019-07-09 | 天津阿尔发保健品有限公司 | 一种具有燃烧体内脂肪功效的谷物制品配方 |
| USD1050801S1 (en) | 2022-12-16 | 2024-11-12 | Yeti Coolers, Llc | Lid |
| USD1050803S1 (en) | 2022-12-16 | 2024-11-12 | Yeti Coolers, Llc | Lid |
Family Cites Families (61)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2242230A (en) | 1941-05-20 | Process of producing conjugation in | ||
| US2350583A (en) | 1944-06-06 | Drying oils | ||
| US558881A (en) | 1896-04-21 | Track-jack | ||
| GB558881A (enExample) | 1900-01-01 | |||
| DE1156788C2 (de) | 1959-12-02 | 1973-11-22 | Brinckmann Harburger Fett | Verfahren zur Umwandlung von Fettsaeureestern einwertiger Alkohole mit isolierten Doppelbindungen (íÀIsolenfettsaeureesterníÂ) in Fettsaeureester mit konjugierten Doppelbindungen (íÀKonjuenfettsaeureesteríÂ) |
| US3278567A (en) | 1965-01-19 | 1966-10-11 | Pacific Vegets Le Oil Corp | Process for conjugating and isomerizing drying oils and products |
| US3729379A (en) | 1971-08-31 | 1973-04-24 | Us Agriculture | Hydroxy-conjugated fatty acids |
| US4164505A (en) | 1977-07-08 | 1979-08-14 | Sylvachem Corporation | Flow process for conjugating unconjugated unsaturation of fatty acids |
| US4232052A (en) | 1979-03-12 | 1980-11-04 | National Starch And Chemical Corporation | Process for powdering high fat foodstuffs |
| DE3019963A1 (de) | 1980-05-24 | 1981-12-03 | Henkel KGaA, 4000 Düsseldorf | Verfahren zur konjugierung mehrfach ungesaettigter fettsaeuren und fettsaeuregemische |
| JPS6127941A (ja) * | 1984-07-16 | 1986-02-07 | Kuraray Co Ltd | ピルビン酸の製造方法 |
| US5017614A (en) | 1989-02-17 | 1991-05-21 | Wisconsin Alumni Research Foundation | Methods of preventing oxidation, quenching singlet oxygen and inhibiting mold growth and novel compositions therefor |
| US5070104A (en) | 1989-02-17 | 1991-12-03 | Wisconsin Alumni Research Foundation | Methods of chelating metal and novel compositions therefor |
| US5208356A (en) | 1989-02-17 | 1993-05-04 | Wisconsin Alumni Research Foundation | Octadecadienoic phospholipic esters, antioxidant and mold inhibiting compositions |
| US5288619A (en) | 1989-12-18 | 1994-02-22 | Kraft General Foods, Inc. | Enzymatic method for preparing transesterified oils |
| US5468887A (en) | 1992-03-13 | 1995-11-21 | The Dial Corp. | Production of fatty acid methyl esters and soaps therefrom |
| US5554646A (en) | 1992-04-29 | 1996-09-10 | Wisconsin Alumni Research Foundation | Method for reducing body fat in animals |
| US5430066A (en) | 1992-04-29 | 1995-07-04 | Wisconsin Alumni Research Foundation | Methods for preventing weight loss, reduction in weight gain, and anorexia due to immune stimulation |
| US5428072A (en) | 1992-04-29 | 1995-06-27 | Wisconsin Alumni Research Foundation | Method of increasing the efficiency of feed conversion in animals |
| US5674901A (en) | 1995-06-01 | 1997-10-07 | Wisconsin Alumni Research Foundation | Methods of treating animals to maintain or increase CD-4 and CD-8 cell populations |
| US5814663A (en) | 1994-08-29 | 1998-09-29 | Wisconsin Alumni Research Foundation | Method for maintaining an existing level of body fat |
| US5760082C1 (en) | 1994-08-29 | 2001-03-06 | Wisconsin Alumni Res Found | Dietetic foods containing conjugated linoleic acids |
| MY118354A (en) | 1995-05-01 | 2004-10-30 | Scarista Ltd | 1,3-propane diol derivatives as bioactive compounds |
| US5856149A (en) | 1995-06-01 | 1999-01-05 | Wisconsin Alumni Research Foundation | Method of producing conjugated fatty acids |
| JPH0948994A (ja) * | 1995-08-07 | 1997-02-18 | Kao Corp | 脂肪酸の製造方法 |
| DE69615513T2 (de) | 1995-11-14 | 2002-05-08 | Unilever N.V., Rotterdam | Essbarer Brotaufstrich |
| ES2148814T5 (es) | 1995-11-14 | 2005-12-16 | Loders Croklaan B.V. | Procedimiento para la preparacion de materiales con un alto contenido de isomeros de acido linoleico conjugado. |
| US5585400A (en) | 1996-02-27 | 1996-12-17 | Wisconsin Alumni Research Foundation | Methods of attenuating the allergic response in animals |
| WO1997037546A1 (en) | 1996-04-11 | 1997-10-16 | Loders Croklaan B.V. | Free flowing fat compositions |
| US5725873A (en) | 1996-07-22 | 1998-03-10 | Wisconsin Alumni Research Foundation | Method of improving the growth or the efficiency of feed conversion of an animal and compositions for use therein |
| US5760083A (en) | 1996-08-07 | 1998-06-02 | Wisconsin Alumni Research Foundation | Use of CLA to reduce the incidence of valgus and varus leg deforomities in poultry |
| US5804210A (en) | 1996-08-07 | 1998-09-08 | Wisconsin Alumni Research Foundation | Methods of treating animals to maintain or enhance bone mineral content and compositions for use therein |
| JP3017108B2 (ja) | 1996-10-30 | 2000-03-06 | リノール油脂株式会社 | 共役リノール酸の製造方法 |
| US5855917A (en) | 1996-12-04 | 1999-01-05 | Wisconsin Alumni Research Foundation | Method for controlling body fat and/or body weight in animals and pharmaceutical compositions for use therein comprising 20-carbon conjugated unsaturated fatty acids |
| US5885594A (en) | 1997-03-27 | 1999-03-23 | The Procter & Gamble Company | Oral compositions having enhanced mouth-feel |
| US5851572A (en) | 1997-04-25 | 1998-12-22 | Wisconsin Alumni Research Foundation | Method of increasing fat firmness and improving meat quality in animals with conjugated linolenic acid |
| DE19718245C5 (de) | 1997-04-30 | 2004-11-11 | Cognis Deutschland Gmbh & Co. Kg | Synthetische Triglyceride auf Basis konjugierter Linolsäure, Verfahren zu deren Herstellung und deren Verwendung |
| CA2246085C (en) | 1997-09-12 | 2004-04-27 | Krish Bhaggan | Production of materials rich in conjugated isomers of long chain polyunsaturated fatty acid residues |
| US6019990A (en) | 1997-11-21 | 2000-02-01 | Natural Nutrition Ltd. As | Conjugated linoleic acid delivery system in cosmetic preparations |
| JPH11209279A (ja) | 1998-01-05 | 1999-08-03 | Natural Ltd As | 体重減少および肥満処置の方法 |
| US6042869A (en) | 1998-02-20 | 2000-03-28 | Natural Nutrition Ltd. | Bulk animal feeds containing conjugated linoleic acid |
| US6015833A (en) | 1998-03-17 | 2000-01-18 | Conlinco., Inc. | Conjugated linoleic acid compositions |
| DK0950410T3 (da) | 1998-03-17 | 2007-05-07 | Natural Asa | Konjugeret linolsyresammensætninger |
| US6524527B2 (en) * | 1998-03-17 | 2003-02-25 | Natural Corporation | Conjugated linoleic acid compositions |
| US6060514A (en) | 1998-05-04 | 2000-05-09 | Conlin Co., Inc. | Isomer enriched conjugated linoleic acid compositions |
| KR100402040B1 (ko) * | 1998-05-04 | 2003-10-17 | 콘린코 인크. | 이성질체가 강화된 공액 리놀레산 조성물의 이용 방법 |
| US6214372B1 (en) | 1998-05-04 | 2001-04-10 | Con Lin Co., Inc. | Method of using isomer enriched conjugated linoleic acid compositions |
| EP1405666B1 (de) | 1998-08-28 | 2007-03-21 | febit biotech GmbH | Träger für Analytbestimmungsverfahren und Verfahren zur Herstellung des Trägers |
| TW483921B (en) | 1998-10-16 | 2002-04-21 | Idemitsu Petrochemical Co | Flame-retardant thermoplastic resin composition |
| US6440931B1 (en) | 1999-02-23 | 2002-08-27 | Natural Corporation | Conjugated linoleic acid in treatment and prophylaxis of diabetes |
| DE19914279C1 (de) | 1999-03-25 | 2000-09-07 | Jena Optronik Gmbh | Anordnung zum optischen Auslesen der Information von einem matrixförmigen Substrat mit einer Vielzahl von Einzelproben |
| DE19922942A1 (de) | 1999-05-14 | 2000-11-30 | Epigenomics Gmbh | Vorrichtung und Verfahren zur photolithographischen Belichtung von biologischen Stoffen |
| GB9929897D0 (en) * | 1999-12-18 | 2000-02-09 | Slabas Antoni R | Improvements in or relating to conjugated fatty acids and related compounds |
| CA2397655C (en) | 2000-01-19 | 2012-06-05 | Craig M. Ruecker | Solventless extraction process |
| US6432469B1 (en) | 2000-02-17 | 2002-08-13 | Natural Corporation | Bulk animal feeds containing conjugated linoleic acid |
| WO2001077271A2 (en) * | 2000-04-06 | 2001-10-18 | Conlinco, Inc. | Conjugated linoleic acid compositions |
| US6756405B2 (en) * | 2000-04-18 | 2004-06-29 | Natural Asa | Conjugated linoleic acid powder |
| US6380409B1 (en) | 2000-04-24 | 2002-04-30 | Conlin Co., Inc. | Methods for preparing CLA isomers |
| US6217404B1 (en) | 2000-06-16 | 2001-04-17 | Yun Hwan Liao | Toy airplane |
| JP2004514685A (ja) * | 2000-11-29 | 2004-05-20 | スミスクライン・ビーチャム・コーポレイション | 健康状態の改善のための共役リノール酸およびカルシウムを含有するダイエタリー組成物 |
| US6743931B2 (en) * | 2002-09-24 | 2004-06-01 | Natural Asa | Conjugated linoleic acid compositions |
-
2002
- 2002-09-24 US US10/253,216 patent/US6743931B2/en not_active Expired - Lifetime
-
2003
- 2003-09-24 CA CA2499138A patent/CA2499138C/en not_active Expired - Fee Related
- 2003-09-24 DK DK03758523.9T patent/DK1546295T3/en active
- 2003-09-24 WO PCT/IB2003/004897 patent/WO2004029186A2/en not_active Ceased
- 2003-09-24 EP EP03758523.9A patent/EP1546295B1/en not_active Expired - Lifetime
- 2003-09-24 ES ES03758523.9T patent/ES2551680T3/es not_active Expired - Lifetime
- 2003-09-24 AU AU2003274548A patent/AU2003274548B2/en not_active Ceased
- 2003-09-24 JP JP2004539384A patent/JP2006517237A/ja not_active Withdrawn
-
2004
- 2004-06-01 US US10/858,158 patent/US7115759B2/en not_active Expired - Lifetime
-
2005
- 2005-04-22 NO NO20051989A patent/NO333298B1/no not_active IP Right Cessation
-
2011
- 2011-05-02 JP JP2011102764A patent/JP2011190451A/ja not_active Withdrawn
-
2014
- 2014-04-02 JP JP2014075877A patent/JP2014159580A/ja active Pending
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