AU747057B2 - Methods of using isomer enriched conjugated linoleic acid compositions - Google Patents
Methods of using isomer enriched conjugated linoleic acid compositions Download PDFInfo
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- AU747057B2 AU747057B2 AU30083/99A AU3008399A AU747057B2 AU 747057 B2 AU747057 B2 AU 747057B2 AU 30083/99 A AU30083/99 A AU 30083/99A AU 3008399 A AU3008399 A AU 3008399A AU 747057 B2 AU747057 B2 AU 747057B2
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- AU
- Australia
- Prior art keywords
- linoleic acid
- cla
- conjugated linoleic
- acid
- tlo
- 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.)
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Classifications
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- 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
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- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/20—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids
- A61K31/202—Carboxylic acids, e.g. valproic acid having a carboxyl group bound to a chain of seven or more carbon atoms, e.g. stearic, palmitic, arachidic acids having three or more double bonds, e.g. linolenic
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
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- A—HUMAN NECESSITIES
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/001—Refining fats or fatty oils by a combination of two or more of the means hereafter
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- 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
- C11C1/02—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils
- C11C1/025—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids from fats or fatty oils by saponification and release of fatty acids
-
- 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/02—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with glycerol
-
- 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
- C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
- C11C3/14—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by isomerisation
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
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- Pharmacology & Pharmacy (AREA)
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- Polymers & Plastics (AREA)
- Microbiology (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Zoology (AREA)
- Physical Education & Sports Medicine (AREA)
- Animal Husbandry (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Child & Adolescent Psychology (AREA)
- Rheumatology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Epidemiology (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Fodder In General (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Fats And Perfumes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/072421 | 1998-05-04 | ||
| US09/072,421 US6214372B1 (en) | 1998-05-04 | 1998-05-04 | Method of using isomer enriched conjugated linoleic acid compositions |
| US09/072,422 US6060514A (en) | 1998-05-04 | 1998-05-04 | Isomer enriched conjugated linoleic acid compositions |
| US09/072422 | 1998-05-04 | ||
| PCT/US1999/005808 WO1999056781A1 (en) | 1998-05-04 | 1999-03-17 | Methods of using isomer enriched conjugated linoleic acid compositions |
Publications (2)
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| AU3008399A AU3008399A (en) | 1999-11-23 |
| AU747057B2 true AU747057B2 (en) | 2002-05-09 |
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| AU30953/99A Ceased AU747058B2 (en) | 1998-05-04 | 1999-03-17 | Isomer enriched conjugated linoleic acid compositions |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU30953/99A Ceased AU747058B2 (en) | 1998-05-04 | 1999-03-17 | Isomer enriched conjugated linoleic acid compositions |
Country Status (14)
| Country | Link |
|---|---|
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| EP (2) | EP0954983B1 (enExample) |
| JP (12) | JP2001508812A (enExample) |
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Families Citing this family (57)
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| US7101914B2 (en) * | 1998-05-04 | 2006-09-05 | Natural Asa | Isomer enriched conjugated linoleic acid compositions |
| FR2784268B1 (fr) * | 1998-10-12 | 2000-12-29 | Gervais Danone Sa | Nouvelle composition alimentaire, a base de matiere issue du lait, sous la forme d'une emulsion huile dans eau |
| GB9828380D0 (en) * | 1998-12-22 | 1999-02-17 | Unilever Plc | Skin lightening composition |
| US6020378A (en) * | 1999-03-30 | 2000-02-01 | Wisconsin Alumni Research Foundation | Method for selectively altering body fat level, feed efficiently, or weight gain |
| JP4565750B2 (ja) * | 1999-04-27 | 2010-10-20 | 株式会社ヤクルト本社 | 共役リノール酸エステルの製造法 |
| JP3207823B2 (ja) | 1999-04-28 | 2001-09-10 | リノール油脂株式会社 | 共役リノール酸を有効成分とする褐色脂肪増加剤 |
| US6420577B1 (en) * | 1999-12-01 | 2002-07-16 | Her Majesty The Queen In Right Of Canada, As Represented By The Minister Of Agriculture | Method for commercial preparation of conjugated linoleic acid |
| JP4262382B2 (ja) * | 2000-02-03 | 2009-05-13 | 株式会社ヤクルト本社 | 共役脂肪酸グリセリド含有発酵食品及びその製造法 |
| WO2001060331A2 (en) * | 2000-02-15 | 2001-08-23 | Zen-Bio, Inc. | Compositions for preventing cellulite in mammalian skin |
| CA2404799C (en) * | 2000-04-06 | 2007-08-07 | Conlinco, Inc. | Conjugated linoleic acid compositions |
| US20030149288A1 (en) * | 2000-04-18 | 2003-08-07 | Natural Asa | Conjugated linoleic acid powder |
| JP5258134B2 (ja) * | 2000-04-18 | 2013-08-07 | エイカー バイオマリン アーエスアー | 共役リノール酸粉末 |
| US6380409B1 (en) * | 2000-04-24 | 2002-04-30 | Conlin Co., Inc. | Methods for preparing CLA isomers |
| US7025984B1 (en) * | 2000-06-26 | 2006-04-11 | The Procter & Gamble Company | Compositions and methods for body weight management |
| AU2005242170B2 (en) * | 2000-06-26 | 2008-12-18 | The Procter & Gamble Company | Compositions and methods for body weight management |
| US6809115B2 (en) * | 2000-09-21 | 2004-10-26 | Nutrition 21, Inc. | Methods and compositions for the treatment of diabetes, the reduction of body fat, improvement of insulin sensitivity, reduction of hyperglycemia, and reduction of hypercholesterolemia with chromium complexes, conjugated fatty acids, and/or conjugated fatty alcohols |
| WO2002041706A2 (en) * | 2000-11-21 | 2002-05-30 | Alpha Foods Ingredients, Inc. | Bioactive compositions comprising conjugated linoleic acid glycerides and methods for producing bioactive conjugated linoleic acid |
| GB0105622D0 (en) | 2001-03-07 | 2001-04-25 | Natural Asa | Compositions |
| CA2442106A1 (en) * | 2001-03-29 | 2002-10-10 | Basf Aktiengesellschaft | Conjugated unsaturated glyceride mixtures and a method for producing the same |
| KR20020081632A (ko) * | 2001-04-19 | 2002-10-30 | (주)라이브맥스 | Ｃｌａ가 함유된 재구성 지질의 제조방법 및 이용방법 |
| US6677470B2 (en) | 2001-11-20 | 2004-01-13 | Natural Asa | Functional acylglycerides |
| DE10158046A1 (de) * | 2001-11-27 | 2003-06-05 | Basf Ag | Formulierung für den Einsatz in Lebensmitteln, Nahrungsergänzungsmitteln, Futtermitteln, Futterzusatzstoffen, pharmazeutischen und kosmetischen Zubereitungen sowie Verfahren zu deren Herstellung |
| WO2003061402A2 (en) * | 2002-01-22 | 2003-07-31 | Mars, Incorporated | Reduction of renal damage in companion animals |
| US20030138547A1 (en) * | 2002-01-22 | 2003-07-24 | Mars, Incorporated | Weight management system for animals |
| DE10219781A1 (de) | 2002-05-03 | 2003-11-13 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von konjugierten Linolsäureglyceriden |
| DE10236086A1 (de) * | 2002-08-07 | 2004-02-19 | Cognis Deutschland Gmbh & Co. Kg | Verfahren zur Herstellung von konjugierter Linolsäure |
| US20040044079A1 (en) * | 2002-09-04 | 2004-03-04 | The Iams Company | Methods and compositions for weight control |
| US7244874B2 (en) * | 2002-09-17 | 2007-07-17 | The Regents Of The University Of California | Stearoyl CoA desaturase transgenic non-human animals |
| US6743931B2 (en) * | 2002-09-24 | 2004-06-01 | Natural Asa | Conjugated linoleic acid compositions |
| WO2004048504A2 (en) * | 2002-11-26 | 2004-06-10 | George Washington University | Method and composition with conjugated linoleic acid esters |
| JP4510045B2 (ja) * | 2003-01-31 | 2010-07-21 | 日清オイリオグループ株式会社 | 共役リノール酸異性体の精製方法およびその用途 |
| JP2004248671A (ja) * | 2003-01-31 | 2004-09-09 | Rinoru Oil Mills Co Ltd | 共役リノール酸異性体の精製方法およびその用途 |
| WO2004096748A1 (en) * | 2003-04-25 | 2004-11-11 | Ilshinwells Co., Ltd. | Preparation method of conjugated linoleic acid diglycerides |
| US6897327B2 (en) * | 2003-05-08 | 2005-05-24 | Stepan Company | Manufacture of conjugated linoleic salts and acids |
| US20040228948A1 (en) * | 2003-05-16 | 2004-11-18 | Kennelly John J. | Increasing the concentration of conjugated linoleic acid isomers in the milk fat and/or tissue fat of ruminants |
| US20050069593A1 (en) * | 2003-09-29 | 2005-03-31 | Life Time Fitness, Inc. | Nutritional supplement containing 7-Keto-DHEA and conjugated linoleic acid |
| EP1541040A1 (de) * | 2003-12-04 | 2005-06-15 | Cognis Iberia S.L | Zubereitung zur oralen Aufnahme (VI) enthaltend einen Extrakt oder Wirkstoffe der Pflanze Medicago sativa |
| AU2003299920A1 (en) * | 2003-12-23 | 2005-08-03 | 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 |
| EP1627565A1 (en) * | 2004-08-10 | 2006-02-22 | Consejo Superior de Investigaciones Cientificas (CSIC) | Use of flavanol derivatives for the cryopreservation of living cells |
| ES2258928A1 (es) * | 2005-02-25 | 2006-09-01 | Aceites Borges Pont, S.A. | Composicion a base de aceites vegetales y acido linoleico conjugado. |
| DE602006016476D1 (de) * | 2005-12-05 | 2010-10-07 | Stepan Co | Verfahren zur herstellung von konjugierter linolsäure und derivaten davon aus ricinolsäure |
| WO2007118614A1 (en) * | 2006-04-13 | 2007-10-25 | Lipid Nutrition B.V. | Process for producing isomer enriched conjugated linoleic acid compositions |
| JP5099808B2 (ja) * | 2006-05-29 | 2012-12-19 | 独立行政法人農業・食品産業技術総合研究機構 | 脂質代謝改善用組成物 |
| DE102007009649A1 (de) * | 2007-02-26 | 2008-08-28 | Beiersdorf Ag | Nahrungsergänzungsmittel zur Pflege und/oder Verschönerung der Haut |
| JP2008237032A (ja) * | 2007-03-23 | 2008-10-09 | Ezaki Glico Co Ltd | 高嗜好性食品 |
| CN101686696A (zh) * | 2007-04-24 | 2010-03-31 | 脂质营养品有限公司 | 低糖酸奶 |
| KR100809411B1 (ko) * | 2007-08-31 | 2008-03-05 | (주)에이치케이바이오텍 | 체지방감소용 조성물 |
| ES2430200T3 (es) * | 2007-10-29 | 2013-11-19 | Stepan Specialty Products, Llc | Composición de aderezo |
| KR101482775B1 (ko) * | 2010-08-25 | 2015-01-16 | 이화여자대학교 산학협력단 | 운데실렌산 및/또는 공액리놀렌산을 포함하는 퇴행성 신경질환의 예방 또는 치료용 조성물 |
| WO2012026663A1 (ko) * | 2010-08-25 | 2012-03-01 | 이화여자대학교 산학협력단 | 운데실렌산, 공액리놀레산 및/또는 공액리놀레산 이성질체를 포함하는 항암보조제 |
| AU2014228387B2 (en) | 2013-03-11 | 2016-09-01 | Sciadonics, Inc. | Lipid compositions containing bioactive fatty acids |
| CN120240575A (zh) * | 2014-03-13 | 2025-07-04 | 巴斯夫欧洲公司 | 富含瘤胃不稳定成分的颗粒的反刍动物饲料 |
| KR101907438B1 (ko) * | 2016-12-08 | 2018-10-15 | 현대오트론 주식회사 | 차량용 게이트웨이의 주기 메시지 송수신 방법 |
| CN112451512A (zh) * | 2020-11-26 | 2021-03-09 | 青海省人民医院 | 一种药物组合物及其治疗骨质疏松的用途 |
| CN116618414A (zh) * | 2023-05-25 | 2023-08-22 | 贵州民族大学 | 一种餐厨垃圾全量资源化利用方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5554646A (en) * | 1992-04-29 | 1996-09-10 | Wisconsin Alumni Research Foundation | Method for reducing body fat in animals |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US5208356A (en) | 1989-02-17 | 1993-05-04 | Wisconsin Alumni Research Foundation | Octadecadienoic phospholipic esters, antioxidant and mold inhibiting compositions |
| GB2240051B (en) | 1990-01-18 | 1993-04-14 | Pall Corp | Cylindrical filters and their manufacture |
| 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 |
| US5428072A (en) * | 1992-04-29 | 1995-06-27 | Wisconsin Alumni Research Foundation | Method of increasing the efficiency of feed conversion 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 |
| 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 |
| US5856149A (en) | 1995-06-01 | 1999-01-05 | Wisconsin Alumni Research Foundation | Method of producing conjugated fatty acids |
| DE69615513T2 (de) | 1995-11-14 | 2002-05-08 | Unilever N.V., Rotterdam | Essbarer Brotaufstrich |
| KR100300826B1 (ko) * | 1995-11-14 | 2001-08-31 | 씨.지. 온닝크 | 장쇄다불포화지방산을다량함유한물질의제조방법 |
| US5585400A (en) | 1996-02-27 | 1996-12-17 | Wisconsin Alumni Research Foundation | Methods of attenuating the allergic response in animals |
| 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 |
| 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 |
| 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 |
| 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 |
| SE9704584L (sv) * | 1997-12-05 | 1999-07-19 | Lennart Bjoerck | Framställning av konjugerad linolsyra |
| US6015833A (en) | 1998-03-17 | 2000-01-18 | Conlinco., Inc. | Conjugated linoleic acid compositions |
-
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
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