JP4217798B2 - 共役リノール酸をベースとする合成トリグリセリドの製造方法 - Google Patents
共役リノール酸をベースとする合成トリグリセリドの製造方法 Download PDFInfo
- Publication number
- JP4217798B2 JP4217798B2 JP54655698A JP54655698A JP4217798B2 JP 4217798 B2 JP4217798 B2 JP 4217798B2 JP 54655698 A JP54655698 A JP 54655698A JP 54655698 A JP54655698 A JP 54655698A JP 4217798 B2 JP4217798 B2 JP 4217798B2
- Authority
- JP
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- Prior art keywords
- conjugated linoleic
- linoleic acid
- acid
- triglycerides
- reaction
- 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.)
- Expired - Fee Related
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- 229940108924 conjugated linoleic acid Drugs 0.000 title claims abstract description 51
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- 238000000034 method Methods 0.000 title claims description 7
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- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 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 2
- 150000003626 triacylglycerols Chemical class 0.000 title abstract description 27
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 19
- 239000000194 fatty acid Substances 0.000 claims abstract description 19
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 24
- 150000004665 fatty acids Chemical class 0.000 claims description 16
- 238000005886 esterification reaction Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 238000005809 transesterification reaction Methods 0.000 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 8
- 230000032050 esterification Effects 0.000 claims description 8
- 239000011541 reaction mixture Substances 0.000 claims description 8
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- 239000011261 inert gas Substances 0.000 claims description 6
- 239000012298 atmosphere Substances 0.000 claims description 4
- 239000010409 thin film Substances 0.000 claims description 3
- -1 fatty acid esters Chemical class 0.000 abstract description 7
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- 235000013305 food Nutrition 0.000 description 15
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- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
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- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
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- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 2
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- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ZQPPMHVWECSIRJ-MDZDMXLPSA-N elaidic acid Chemical compound CCCCCCCC\C=C\CCCCCCCC(O)=O ZQPPMHVWECSIRJ-MDZDMXLPSA-N 0.000 description 2
- 235000013373 food additive Nutrition 0.000 description 2
- 239000002778 food additive Substances 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
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- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- SIOLDWZBFABPJU-UHFFFAOYSA-N isotridecanoic acid Chemical compound CC(C)CCCCCCCCCC(O)=O SIOLDWZBFABPJU-UHFFFAOYSA-N 0.000 description 2
- 229960004488 linolenic acid Drugs 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- 239000003346 palm kernel oil Substances 0.000 description 2
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- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
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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 1
- ADHNUPOJJCKWRT-JLXBFWJWSA-N (2e,4e)-octadeca-2,4-dienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C(O)=O ADHNUPOJJCKWRT-JLXBFWJWSA-N 0.000 description 1
- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
- CUXYLFPMQMFGPL-UHFFFAOYSA-N (9Z,11E,13E)-9,11,13-Octadecatrienoic acid Natural products CCCCC=CC=CC=CCCCCCCCC(O)=O CUXYLFPMQMFGPL-UHFFFAOYSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- GKJZMAHZJGSBKD-ANYPYVPJSA-N 10-trans-12-cis-linoleic acid Natural products CCCCCC=C\C=C\CCCCCCCCC(O)=O GKJZMAHZJGSBKD-ANYPYVPJSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
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- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
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- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 240000007817 Olea europaea Species 0.000 description 1
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- 229930003268 Vitamin C Natural products 0.000 description 1
- ISKQADXMHQSTHK-UHFFFAOYSA-N [4-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=C(CN)C=C1 ISKQADXMHQSTHK-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
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- CUXYLFPMQMFGPL-SUTYWZMXSA-N all-trans-octadeca-9,11,13-trienoic acid Chemical compound CCCC\C=C\C=C\C=C\CCCCCCCC(O)=O CUXYLFPMQMFGPL-SUTYWZMXSA-N 0.000 description 1
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- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
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- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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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
- 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
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
- A23B2/742—Organic compounds containing oxygen
- A23B2/754—Organic compounds containing oxygen containing carboxyl groups
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
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- 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
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- C—CHEMISTRY; METALLURGY
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- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
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- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Engineering & Computer Science (AREA)
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- Health & Medical Sciences (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| DE19718245A DE19718245C5 (de) | 1997-04-30 | 1997-04-30 | Synthetische Triglyceride auf Basis konjugierter Linolsäure, Verfahren zu deren Herstellung und deren Verwendung |
| DE19718245.3 | 1997-04-30 | ||
| PCT/EP1998/002332 WO1998049129A1 (de) | 1997-04-30 | 1998-04-21 | Synthetische triglyceride auf basis konjugierter linolsäure |
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| JP2002510288A JP2002510288A (ja) | 2002-04-02 |
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| KR (1) | KR100483247B1 (enExample) |
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| PT (1) | PT980349E (enExample) |
| WO (1) | WO1998049129A1 (enExample) |
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| US7078051B1 (en) | 1998-08-11 | 2006-07-18 | Natural Asa | Conjugated linoleic acid alkyl esters in feedstuffs and food |
| 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 |
| US7776353B1 (en) | 1998-03-17 | 2010-08-17 | Aker Biomarine Asa | Conjugated linoleic acid compositions |
| KR100402040B1 (ko) | 1998-05-04 | 2003-10-17 | 콘린코 인크. | 이성질체가 강화된 공액 리놀레산 조성물의 이용 방법 |
| US7101914B2 (en) | 1998-05-04 | 2006-09-05 | Natural Asa | Isomer enriched conjugated linoleic acid compositions |
| US6060514A (en) * | 1998-05-04 | 2000-05-09 | Conlin Co., Inc. | 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 |
| KR100350432B1 (ko) * | 1998-09-02 | 2002-08-28 | 하영래 | 공역 리놀레인산 유도체 및 그의 합성방법 |
| AU3843200A (en) * | 1999-04-27 | 2000-11-10 | Kabushiki Kaisha Yakult Honsha | Conjugated fatty acid esters |
| AU6402700A (en) * | 1999-07-09 | 2001-01-30 | Monsanto Company | Treatment of cyclooxygenase-2 mediated disorders using conjugated fatty acid compounds |
| GB9918028D0 (en) * | 1999-07-30 | 1999-09-29 | Unilever Plc | Skin care composition |
| GB9918025D0 (en) * | 1999-07-30 | 1999-09-29 | Unilever Plc | Skin care composition |
| ITMI991894A1 (it) * | 1999-09-09 | 2001-03-09 | Carlo Ghisalberti | Acido linoleico coniugato e trigliceride nuovi metodi di sintesi e d'uso |
| US7947737B1 (en) | 1999-09-30 | 2011-05-24 | Aker Biomarine Asa | Method of treating hypertension and reducing serum lipase activity |
| 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 |
| US20040121042A1 (en) * | 2001-04-25 | 2004-06-24 | Kabushiki Kaisha Yakult Honsha | Fermented foods and process for producing the same |
| 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 |
| 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 |
| JP4220247B2 (ja) * | 2001-03-29 | 2009-02-04 | ビーエーエスエフ ソシエタス・ヨーロピア | 共役不飽和グリセリド混合物及びその製造方法 |
| DE10143534B4 (de) | 2001-09-06 | 2005-03-24 | Cognis Deutschland Gmbh & Co. Kg | Verfahren zur Herstellung von konjugierten Fettsäureestern |
| US6677470B2 (en) | 2001-11-20 | 2004-01-13 | Natural Asa | Functional acylglycerides |
| DE10219781A1 (de) | 2002-05-03 | 2003-11-13 | Cognis Deutschland Gmbh | Verfahren zur Herstellung von konjugierten Linolsäureglyceriden |
| US6743931B2 (en) | 2002-09-24 | 2004-06-01 | Natural Asa | Conjugated linoleic acid compositions |
| JP4524547B2 (ja) * | 2003-07-16 | 2010-08-18 | 株式会社カネカ | 油脂組成物の製造法、及びこれを用いる油脂組成物 |
| DE102004043824A1 (de) | 2004-09-10 | 2006-03-16 | Cognis Ip Management Gmbh | Emulsionen mit ungesättigten Fettsäuren und deren Estern |
| ITFI20050024A1 (it) * | 2005-02-14 | 2006-08-15 | Fernando Cantini | Lipidi per l'alimentazione degli animali |
| BE1021434B1 (nl) | 2013-11-20 | 2015-11-20 | Proviron Holding | Veevoeder aangerijkt met een combinatie van monoglycerides. |
| CN106361739A (zh) * | 2016-08-29 | 2017-02-01 | 大连槿藏商贸有限公司 | 共轭亚油酸或其衍生物在制备乙醛脱氢酶促进剂方面的应用 |
| CN111040882B (zh) * | 2019-11-25 | 2021-10-26 | 江南大学 | 一种基于模型化计算的中长碳链甘油三酯的制备方法 |
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| DE513540C (de) * | 1928-02-21 | 1930-11-29 | Johannes Scheiber Dr | Verfahren zur Herstellung von Lacken und Anstrichmitteln aus Rizinusoelfettsaeuren |
| DE2155727C3 (de) * | 1971-11-10 | 1982-06-16 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Isomerisierung von ungesättigten Fettsäureestern mehrwertiger Alkohole |
| US3984444A (en) * | 1971-11-10 | 1976-10-05 | Hoechst Aktiengesellschaft | Isomerization process of a higher fatty acid ester having isolated double bonds |
| 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 |
| US5208356A (en) * | 1989-02-17 | 1993-05-04 | Wisconsin Alumni Research Foundation | Octadecadienoic phospholipic esters, antioxidant and mold inhibiting compositions |
| 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 |
| US5554646A (en) * | 1992-04-29 | 1996-09-10 | Wisconsin Alumni Research Foundation | Method for reducing body fat in animals |
| JP3138358B2 (ja) * | 1993-03-31 | 2001-02-26 | 雪印乳業株式会社 | 共役リノール酸の製造方法およびそれを含有させた食品 |
| MY118354A (en) * | 1995-05-01 | 2004-10-30 | Scarista Ltd | 1,3-propane diol derivatives as bioactive compounds |
| 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. |
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1997
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1998
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- 1998-04-21 WO PCT/EP1998/002332 patent/WO1998049129A1/de not_active Ceased
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