CA2287476A1 - Conjugated linolenic acid-based synthetic triglycerides - Google Patents

Conjugated linolenic acid-based synthetic triglycerides Download PDF

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Publication number
CA2287476A1
CA2287476A1 CA002287476A CA2287476A CA2287476A1 CA 2287476 A1 CA2287476 A1 CA 2287476A1 CA 002287476 A CA002287476 A CA 002287476A CA 2287476 A CA2287476 A CA 2287476A CA 2287476 A1 CA2287476 A1 CA 2287476A1
Authority
CA
Canada
Prior art keywords
providing
synthetic triglycerides
fatty acid
linolenic acid
based synthetic
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.)
Granted
Application number
CA002287476A
Other languages
French (fr)
Other versions
CA2287476C (en
Inventor
Franz Timmermann
Rolf Gaupp
Juergen Gierke
Rainer Von Kries
Wolfgang Adams
Andreas Sander
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF Personal Care and Nutrition GmbH
Original Assignee
Henkel Kommanditgesellschaft Auf Aktien
Franz Timmermann
Rolf Gaupp
Juergen Gierke
Rainer Von Kries
Wolfgang Adams
Andreas Sander
Cognis Deutschland Gmbh
Cognis Chemie Gmbh & Co. Kg
Cognis Deutschland Ii Gmbh & Co. Kg
Cognis Deutschland Gmbh & Co. Kg
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.)
Filing date
Publication date
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=7828208&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=CA2287476(A1) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Application filed by Henkel Kommanditgesellschaft Auf Aktien, Franz Timmermann, Rolf Gaupp, Juergen Gierke, Rainer Von Kries, Wolfgang Adams, Andreas Sander, Cognis Deutschland Gmbh, Cognis Chemie Gmbh & Co. Kg, Cognis Deutschland Ii Gmbh & Co. Kg, Cognis Deutschland Gmbh & Co. Kg filed Critical Henkel Kommanditgesellschaft Auf Aktien
Publication of CA2287476A1 publication Critical patent/CA2287476A1/en
Application granted granted Critical
Publication of CA2287476C publication Critical patent/CA2287476C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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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
    • C11C3/08—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with fatty acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/02—Other edible oils or fats, e.g. shortenings, cooking oils characterised by the production or working-up
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3481—Organic compounds containing oxygen
    • A23L3/3508—Organic compounds containing oxygen containing carboxyl groups
    • A23L3/3517—Carboxylic acid esters
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • 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
    • A23L33/115—Fatty acids or derivatives thereof; Fats or oils
    • A23L33/12—Fatty acids or derivatives thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L5/00—Preparation or treatment of foods or foodstuffs, in general; Food or foodstuffs obtained thereby; Materials therefor
    • A23L5/40—Colouring or decolouring of foods
    • A23L5/41—Retaining or modifying natural colour by use of additives, e.g. optical brighteners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/02—Nutrients, e.g. vitamins, minerals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
    • C07C69/587—Monocarboxylic acid esters having at least two carbon-to-carbon double bonds
    • 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
    • C11B3/008—Refining fats or fatty oils by filtration, e.g. including ultra filtration, dialysis
    • 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
    • C11B3/10—Refining fats or fatty oils by adsorption
    • 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
    • C11C3/04—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils
    • C11C3/06—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fats or fatty oils with glycerol
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polymers & Plastics (AREA)
  • Food Science & Technology (AREA)
  • Nutrition Science (AREA)
  • Wood Science & Technology (AREA)
  • Microbiology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Mycology (AREA)
  • Biochemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Obesity (AREA)
  • Toxicology (AREA)
  • Fats And Perfumes (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

A process for making synthetic triglycerides involving: (a) providing a reaction component selected from the group consisting of glycerol, a triglyceride, and mixtures thereof; (b) providing a fatty acid mixture containing at least 50% by weight, based on the weight of the fatty acid mixture, of conjugated linoleic acid; (c) providing an inert gas atmosphere;
(d) combining the reaction component with the fatty acid mixture, in the inert atmosphere, to form a reaction mixture; and (e) heating the reaction mixture to a temperature of from 180 to 240°C, at a heating rate of from 0.5 to 3 K per minute, thus forming the synthetic triglyceride.
CA002287476A 1997-04-30 1998-04-21 Conjugated linolenic acid-based synthetic triglycerides Expired - Fee Related CA2287476C (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19718245.3 1997-04-30
DE19718245A DE19718245C5 (en) 1997-04-30 1997-04-30 Synthetic triglycerides based on conjugated linoleic acid, process for their preparation and their use
PCT/EP1998/002332 WO1998049129A1 (en) 1997-04-30 1998-04-21 Conjugated linolenic acid-based synthetic triglycerides

Publications (2)

Publication Number Publication Date
CA2287476A1 true CA2287476A1 (en) 1998-11-05
CA2287476C CA2287476C (en) 2007-04-10

Family

ID=7828208

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002287476A Expired - Fee Related CA2287476C (en) 1997-04-30 1998-04-21 Conjugated linolenic acid-based synthetic triglycerides

Country Status (13)

Country Link
EP (5) EP1135998B1 (en)
JP (1) JP4217798B2 (en)
KR (1) KR100483247B1 (en)
AT (5) ATE246881T1 (en)
AU (1) AU735493B2 (en)
BR (1) BR9809421A (en)
CA (1) CA2287476C (en)
DE (6) DE19718245C5 (en)
DK (5) DK0980349T3 (en)
ES (5) ES2201005T3 (en)
NZ (1) NZ500698A (en)
PT (1) PT980349E (en)
WO (1) WO1998049129A1 (en)

Families Citing this family (32)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6015833A (en) 1998-03-17 2000-01-18 Conlinco., Inc. Conjugated linoleic acid compositions
US7776353B1 (en) 1998-03-17 2010-08-17 Aker Biomarine Asa Conjugated linoleic acid compositions
KR100619651B1 (en) 1998-03-17 2006-09-05 콘린코 인크. Conjugated linoleic acid compositions
US7078051B1 (en) 1998-08-11 2006-07-18 Natural Asa Conjugated linoleic acid alkyl esters in feedstuffs and food
WO1999056781A1 (en) 1998-05-04 1999-11-11 Conlinco, Inc. Methods of using isomer enriched conjugated linoleic acid compositions
US7101914B2 (en) 1998-05-04 2006-09-05 Natural Asa Isomer enriched conjugated linoleic acid compositions
US6214372B1 (en) 1998-05-04 2001-04-10 Con Lin Co., Inc. Method of using isomer enriched conjugated linoleic acid compositions
US6060514A (en) * 1998-05-04 2000-05-09 Conlin Co., Inc. Isomer enriched conjugated linoleic acid compositions
KR100350432B1 (en) * 1998-09-02 2002-08-28 하영래 Derivatives of conjugated linoleic acid and method for synthesizing thereof
JP4565750B2 (en) * 1999-04-27 2010-10-20 株式会社ヤクルト本社 Method for producing conjugated linoleic acid ester
WO2001003688A2 (en) * 1999-07-09 2001-01-18 Pharmacia Corporation Treatment of cyclooxygenase-2 mediated disorders using conjugated fatty acid compounds
GB9918025D0 (en) * 1999-07-30 1999-09-29 Unilever Plc Skin care composition
GB9918028D0 (en) * 1999-07-30 1999-09-29 Unilever Plc Skin care composition
ITMI991894A1 (en) * 1999-09-09 2001-03-09 Carlo Ghisalberti CONJUGATED LINOLEIC ACID AND TRIGLYCERIDE NEW METHODS OF SYNTHESIS AND USE
US7947737B1 (en) 1999-09-30 2011-05-24 Aker Biomarine Asa Method of treating hypertension and reducing serum lipase activity
JP4262382B2 (en) * 2000-02-03 2009-05-13 株式会社ヤクルト本社 Conjugated fatty acid glyceride-containing fermented food and process for producing the same
AU5144901A (en) * 2000-04-06 2001-10-23 Conlinco Inc Conjugated linoleic acid compositions
JP5258134B2 (en) 2000-04-18 2013-08-07 エイカー バイオマリン アーエスアー Conjugated linoleic acid powder
US6380409B1 (en) 2000-04-24 2002-04-30 Conlin Co., Inc. Methods for preparing CLA isomers
AU2002228992A1 (en) * 2000-11-21 2002-06-03 Alpha Foods Ingredients, Inc. Bioactive compositions comprising conjugated linoleic acid glycerides and methods for producing bioactive conjugated linoleic acid
EP1373182A1 (en) * 2001-03-29 2004-01-02 Basf Aktiengesellschaft Conjugated unsaturated glyceride mixtures and a method for producing the same
AU2001252569B2 (en) * 2001-04-25 2008-06-19 Kabushiki Kaisha Yakult Honsha Fermented foods and process for producing the same
DE10143534B4 (en) 2001-09-06 2005-03-24 Cognis Deutschland Gmbh & Co. Kg Process for the preparation of conjugated fatty acid esters
US6677470B2 (en) 2001-11-20 2004-01-13 Natural Asa Functional acylglycerides
DE10219781A1 (en) 2002-05-03 2003-11-13 Cognis Deutschland Gmbh Process for the preparation of conjugated linoleic acid glycerides
US6743931B2 (en) 2002-09-24 2004-06-01 Natural Asa Conjugated linoleic acid compositions
JP4524547B2 (en) * 2003-07-16 2010-08-18 株式会社カネカ Oil and fat composition manufacturing method and oil and fat composition using the same
DE102004043824A1 (en) 2004-09-10 2006-03-16 Cognis Ip Management Gmbh Emulsions with unsaturated fatty acids and their esters
ITFI20050024A1 (en) * 2005-02-14 2006-08-15 Fernando Cantini LIPIDS FOR ANIMAL FEEDING
BE1021434B1 (en) 2013-11-20 2015-11-20 Proviron Holding FEED FEED WITH A COMBINATION OF MONOGLYCERIDES.
CN106361739A (en) * 2016-08-29 2017-02-01 大连槿藏商贸有限公司 Application of conjugated linoleic acid or derivatives thereof in aspect of preparing acetaldehyde dehydrogenase accelerant
CN111040882B (en) * 2019-11-25 2021-10-26 江南大学 Preparation method of medium-long carbon chain triglyceride based on modeling calculation

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DE513540C (en) * 1928-02-21 1930-11-29 Johannes Scheiber Dr Process for the production of varnishes and paints from castor oil fatty acids
DE2155727C3 (en) * 1971-11-10 1982-06-16 Hoechst Ag, 6000 Frankfurt Process for the isomerization of unsaturated fatty acid esters of polyhydric alcohols
US3984444A (en) * 1971-11-10 1976-10-05 Hoechst Aktiengesellschaft Isomerization process of a higher fatty acid ester having isolated double bonds
US5208356A (en) * 1989-02-17 1993-05-04 Wisconsin Alumni Research Foundation Octadecadienoic phospholipic esters, antioxidant and mold inhibiting compositions
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
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
JP3138358B2 (en) * 1993-03-31 2001-02-26 雪印乳業株式会社 Method for producing conjugated linoleic acid and food containing the same
MY118354A (en) * 1995-05-01 2004-10-30 Scarista Ltd 1,3-propane diol derivatives as bioactive compounds
WO1997018320A1 (en) * 1995-11-14 1997-05-22 Loders Croklaan B.V. Process for the preparation of materials with a high content of long chain polyunsaturated fatty acids

Also Published As

Publication number Publication date
ES2201005T3 (en) 2004-03-16
EP1135998A1 (en) 2001-09-26
DE19718245C5 (en) 2004-11-11
ATE243033T1 (en) 2003-07-15
DK1138326T3 (en) 2003-10-13
EP1138325A1 (en) 2001-10-04
JP4217798B2 (en) 2009-02-04
NZ500698A (en) 2001-06-29
EP1135996A1 (en) 2001-09-26
EP0980349B1 (en) 2001-12-19
ATE246881T1 (en) 2003-08-15
EP0980349A1 (en) 2000-02-23
ES2204784T3 (en) 2004-05-01
AU7431398A (en) 1998-11-24
DE19718245C1 (en) 1998-07-30
WO1998049129A1 (en) 1998-11-05
DK0980349T3 (en) 2002-04-15
KR100483247B1 (en) 2005-04-15
DE59808772D1 (en) 2003-07-24
ATE243032T1 (en) 2003-07-15
KR20010020344A (en) 2001-03-15
ES2169515T3 (en) 2002-07-01
JP2002510288A (en) 2002-04-02
EP1138326B1 (en) 2003-06-18
DE59809302D1 (en) 2003-09-18
ATE211126T1 (en) 2002-01-15
CA2287476C (en) 2007-04-10
EP1135998B1 (en) 2003-08-13
EP1138325B1 (en) 2003-06-18
PT980349E (en) 2002-06-28
DK1135996T3 (en) 2003-12-08
BR9809421A (en) 2000-06-13
EP1135996B1 (en) 2003-08-13
EP1138326A1 (en) 2001-10-04
ATE246879T1 (en) 2003-08-15
DE59808773D1 (en) 2003-07-24
DE59802540D1 (en) 2002-01-31
ES2201006T3 (en) 2004-03-16
ES2201004T3 (en) 2004-03-16
AU735493B2 (en) 2001-07-12
DE59809303D1 (en) 2003-09-18
DK1135998T3 (en) 2003-12-08
DK1138325T3 (en) 2003-10-13

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