JP2000516480A - 共役リノール酸組成物 - Google Patents
共役リノール酸組成物Info
- Publication number
- JP2000516480A JP2000516480A JP11547251A JP54725199A JP2000516480A JP 2000516480 A JP2000516480 A JP 2000516480A JP 11547251 A JP11547251 A JP 11547251A JP 54725199 A JP54725199 A JP 54725199A JP 2000516480 A JP2000516480 A JP 2000516480A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- composition
- linoleic acid
- cla
- octadecadienoic
- 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- Withdrawn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 title claims abstract description 172
- 229940108924 conjugated linoleic acid Drugs 0.000 title claims abstract description 133
- 239000000203 mixture Substances 0.000 title claims abstract description 105
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 title claims abstract 13
- 239000000047 product Substances 0.000 claims abstract description 45
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims abstract description 43
- 235000020778 linoleic acid Nutrition 0.000 claims abstract description 39
- 235000015872 dietary supplement Nutrition 0.000 claims abstract description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 57
- 230000008569 process Effects 0.000 claims description 39
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 32
- 238000006317 isomerization reaction Methods 0.000 claims description 31
- 241001465754 Metazoa Species 0.000 claims description 30
- ADHNUPOJJCKWRT-JLXBFWJWSA-N (2e,4e)-octadeca-2,4-dienoic acid Chemical class CCCCCCCCCCCCC\C=C\C=C\C(O)=O ADHNUPOJJCKWRT-JLXBFWJWSA-N 0.000 claims description 29
- 239000003921 oil Substances 0.000 claims description 28
- 235000019198 oils Nutrition 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- 235000019485 Safflower oil Nutrition 0.000 claims description 22
- 235000021588 free fatty acids Nutrition 0.000 claims description 22
- 239000003813 safflower oil Substances 0.000 claims description 22
- 235000005713 safflower oil Nutrition 0.000 claims description 22
- 239000003513 alkali Substances 0.000 claims description 21
- 235000015112 vegetable and seed oil Nutrition 0.000 claims description 21
- 150000002148 esters Chemical class 0.000 claims description 18
- 235000013305 food Nutrition 0.000 claims description 18
- 238000010438 heat treatment Methods 0.000 claims description 12
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- 239000011541 reaction mixture Substances 0.000 claims description 10
- 235000019486 Sunflower oil Nutrition 0.000 claims description 9
- JGFMXQLVWUGIPI-UHFFFAOYSA-N octadeca-11,13-dienoic acid Chemical class CCCCC=CC=CCCCCCCCCCC(O)=O JGFMXQLVWUGIPI-UHFFFAOYSA-N 0.000 claims description 9
- QJKCKUNKNNYJNS-UHFFFAOYSA-N octadeca-8,10-dienoic acid Chemical class CCCCCCCC=CC=CCCCCCCC(O)=O QJKCKUNKNNYJNS-UHFFFAOYSA-N 0.000 claims description 9
- 239000002600 sunflower oil Substances 0.000 claims description 9
- 125000005907 alkyl ester group Chemical group 0.000 claims description 8
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- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 4
- 125000001095 phosphatidyl group Chemical group 0.000 claims description 4
- 239000011260 aqueous acid Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 238000000199 molecular distillation Methods 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 2
- 235000012041 food component Nutrition 0.000 claims description 2
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- 229940049918 linoleate Drugs 0.000 claims description 2
- 238000004332 deodorization Methods 0.000 claims 1
- 244000144972 livestock Species 0.000 claims 1
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- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims 1
- 238000001291 vacuum drying Methods 0.000 claims 1
- 235000019730 animal feed additive Nutrition 0.000 abstract 1
- JBYXPOFIGCOSSB-XBLVEGMJSA-N 9E,11E-octadecadienoic acid Chemical group CCCCCC\C=C\C=C\CCCCCCCC(O)=O JBYXPOFIGCOSSB-XBLVEGMJSA-N 0.000 description 125
- 238000006243 chemical reaction Methods 0.000 description 55
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 33
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 235000014113 dietary fatty acids Nutrition 0.000 description 17
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- 230000015572 biosynthetic process Effects 0.000 description 16
- 230000021615 conjugation Effects 0.000 description 16
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 241000030538 Thecla Species 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 13
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- 241000282849 Ruminantia Species 0.000 description 6
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- 150000002632 lipids Chemical class 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 229960004106 citric acid Drugs 0.000 description 5
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- 238000004519 manufacturing process Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 4
- 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 3
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- GKJZMAHZJGSBKD-BLHCBFLLSA-N (10e,12e)-octadeca-10,12-dienoic acid Chemical compound CCCCC\C=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-BLHCBFLLSA-N 0.000 description 2
- GKJZMAHZJGSBKD-ANYPYVPJSA-N 10-trans-12-cis-linoleic acid Natural products CCCCCC=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-ANYPYVPJSA-N 0.000 description 2
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- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- YASYEJJMZJALEJ-UHFFFAOYSA-N Citric acid monohydrate Chemical compound O.OC(=O)CC(O)(C(O)=O)CC(O)=O YASYEJJMZJALEJ-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- 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
- A61K31/201—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 one or two double bonds, e.g. oleic, linoleic acids
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
- A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
- A61K47/543—Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biophysics (AREA)
- Food Science & Technology (AREA)
- Nutrition Science (AREA)
- Mycology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polymers & Plastics (AREA)
- Molecular Biology (AREA)
- Fodder In General (AREA)
- Fats And Perfumes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Edible Oils And Fats (AREA)
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US4253898A | 1998-03-17 | 1998-03-17 | |
| US09/042,767 | 1998-03-17 | ||
| US09/042,538 | 1998-03-17 | ||
| US09/042,767 US6015833A (en) | 1998-03-17 | 1998-03-17 | Conjugated linoleic acid compositions |
| US09/132,593 US7078051B1 (en) | 1998-08-11 | 1998-08-11 | Conjugated linoleic acid alkyl esters in feedstuffs and food |
| US09/132,593 | 1998-08-11 | ||
| US16041698A | 1998-09-25 | 1998-09-25 | |
| US09/160,416 | 1998-09-25 | ||
| PCT/US1999/005806 WO1999047135A1 (en) | 1998-03-17 | 1999-03-17 | Conjugated linoleic acid compositions |
Related Child Applications (1)
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|---|---|---|---|
| JP2002188781A Division JP2003073269A (ja) | 1998-03-17 | 2002-06-27 | 共役リノール酸組成物 |
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|---|---|
| JP2000516480A true JP2000516480A (ja) | 2000-12-12 |
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| JP11547251A Withdrawn JP2000516480A (ja) | 1998-03-17 | 1999-03-17 | 共役リノール酸組成物 |
Country Status (14)
| Country | Link |
|---|---|
| US (4) | US7029691B1 (enExample) |
| EP (1) | EP0950410B1 (enExample) |
| JP (1) | JP2000516480A (enExample) |
| KR (1) | KR100619651B1 (enExample) |
| AT (1) | ATE350028T1 (enExample) |
| AU (1) | AU764699B2 (enExample) |
| CA (1) | CA2289648C (enExample) |
| DE (1) | DE69934627T2 (enExample) |
| DK (1) | DK0950410T3 (enExample) |
| ES (1) | ES2279586T3 (enExample) |
| IN (1) | IN2000KO00319A (enExample) |
| MX (1) | MX238954B (enExample) |
| NO (1) | NO331483B1 (enExample) |
| WO (1) | WO1999047135A1 (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005534708A (ja) * | 2002-08-07 | 2005-11-17 | コグニス・ドイッチュランド・ゲゼルシヤフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンデイトゲゼルシヤフト | 共役リノール酸の製造方法 |
| JP2006008532A (ja) * | 2004-06-22 | 2006-01-12 | Juntendo | 共役脂肪酸を有効成分とする運動能力改善剤 |
| JP2006517237A (ja) * | 2002-09-24 | 2006-07-20 | ナチュラル エイエスエイ | 共役リノール酸組成物 |
| JP2008528778A (ja) * | 2005-02-04 | 2008-07-31 | ローダース・クロクラーン・ベスローテンフェンノートシャップ | 脂肪酸の製造方法 |
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- 1999-03-17 CA CA002289648A patent/CA2289648C/en not_active Expired - Fee Related
- 1999-03-17 JP JP11547251A patent/JP2000516480A/ja not_active Withdrawn
- 1999-03-17 US US09/271,024 patent/US7029691B1/en not_active Expired - Lifetime
- 1999-03-17 EP EP99105497A patent/EP0950410B1/en not_active Revoked
- 1999-03-17 DE DE69934627T patent/DE69934627T2/de not_active Expired - Lifetime
- 1999-03-17 US US09/270,940 patent/US6410761B1/en not_active Expired - Lifetime
- 1999-03-17 KR KR1020007010266A patent/KR100619651B1/ko not_active Expired - Fee Related
- 1999-03-17 AU AU31886/99A patent/AU764699B2/en not_active Ceased
- 1999-03-17 ES ES99105497T patent/ES2279586T3/es not_active Expired - Lifetime
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2000
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2002
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2005534708A (ja) * | 2002-08-07 | 2005-11-17 | コグニス・ドイッチュランド・ゲゼルシヤフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンデイトゲゼルシヤフト | 共役リノール酸の製造方法 |
| JP2006517237A (ja) * | 2002-09-24 | 2006-07-20 | ナチュラル エイエスエイ | 共役リノール酸組成物 |
| JP2011190451A (ja) * | 2002-09-24 | 2011-09-29 | Aker Biomarine Asa | 共役リノール酸組成物 |
| JP2014159580A (ja) * | 2002-09-24 | 2014-09-04 | Aker Biomarine Asa | 共役リノール酸組成物 |
| JP2006008532A (ja) * | 2004-06-22 | 2006-01-12 | Juntendo | 共役脂肪酸を有効成分とする運動能力改善剤 |
| JP2008528778A (ja) * | 2005-02-04 | 2008-07-31 | ローダース・クロクラーン・ベスローテンフェンノートシャップ | 脂肪酸の製造方法 |
| JP2008545407A (ja) * | 2005-05-23 | 2008-12-18 | エイカー バイオマリン エイエスエイ | グリセロールを用いた酵素反応による脂肪酸アルキルエステルの濃縮方法 |
| JP2014050403A (ja) * | 2005-05-23 | 2014-03-20 | Epax Hovdebygda As | グリセロールを用いた酵素反応による脂肪酸アルキルエステルの濃縮方法 |
| JP2020512559A (ja) * | 2017-03-31 | 2020-04-23 | メタボロン，インコーポレイテッド | 包括的および定量的な脂質およびトコフェロールの分析 |
Also Published As
| Publication number | Publication date |
|---|---|
| US6610868B2 (en) | 2003-08-26 |
| IN2000KO00319A (enExample) | 2005-03-11 |
| DK0950410T3 (da) | 2007-05-07 |
| AU764699B2 (en) | 2003-08-28 |
| EP0950410B1 (en) | 2007-01-03 |
| AU3188699A (en) | 1999-10-11 |
| KR100619651B1 (ko) | 2006-09-05 |
| WO1999047135A1 (en) | 1999-09-23 |
| KR20010074447A (ko) | 2001-08-04 |
| US20020169332A1 (en) | 2002-11-14 |
| CA2289648C (en) | 2004-06-01 |
| MX238954B (es) | 2006-07-26 |
| ATE350028T1 (de) | 2007-01-15 |
| EP0950410A1 (en) | 1999-10-20 |
| US20040018225A1 (en) | 2004-01-29 |
| NO20004615L (no) | 2000-11-07 |
| NO20004615D0 (no) | 2000-09-15 |
| NO331483B1 (no) | 2012-01-16 |
| WO1999047135A8 (en) | 2001-07-05 |
| US7029691B1 (en) | 2006-04-18 |
| US7514096B2 (en) | 2009-04-07 |
| DE69934627T2 (de) | 2007-10-25 |
| MXPA00009106A (es) | 2002-04-01 |
| CA2289648A1 (en) | 1999-09-23 |
| ES2279586T3 (es) | 2007-08-16 |
| US6410761B1 (en) | 2002-06-25 |
| DE69934627D1 (de) | 2007-02-15 |
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