WO2006106809A1 - 共役脂肪酸濃縮物の製造方法 - Google Patents
共役脂肪酸濃縮物の製造方法 Download PDFInfo
- Publication number
- WO2006106809A1 WO2006106809A1 PCT/JP2006/306634 JP2006306634W WO2006106809A1 WO 2006106809 A1 WO2006106809 A1 WO 2006106809A1 JP 2006306634 W JP2006306634 W JP 2006306634W WO 2006106809 A1 WO2006106809 A1 WO 2006106809A1
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- WO
- WIPO (PCT)
- Prior art keywords
- isomer
- fatty acid
- conjugated
- unsaturated fatty
- acid
- Prior art date
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 44
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 44
- 239000000194 fatty acid Substances 0.000 title claims abstract description 44
- 150000004665 fatty acids Chemical class 0.000 title claims abstract description 43
- 239000012141 concentrate Substances 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 46
- 238000000034 method Methods 0.000 claims abstract description 39
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 36
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 36
- 239000007788 liquid Substances 0.000 claims abstract description 27
- 239000013078 crystal Substances 0.000 claims abstract description 23
- 239000011259 mixed solution Substances 0.000 claims abstract description 13
- 238000002425 crystallisation Methods 0.000 claims abstract description 12
- 238000000926 separation method Methods 0.000 claims abstract description 11
- 230000008025 crystallization Effects 0.000 claims abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical group CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 40
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical class CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 claims description 36
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 33
- 229940108924 conjugated linoleic acid Drugs 0.000 claims description 32
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 10
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 10
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 10
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 10
- 239000005642 Oleic acid Substances 0.000 claims description 10
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 10
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 10
- 239000003960 organic solvent Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 230000001476 alcoholic effect Effects 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 5
- 230000001376 precipitating effect Effects 0.000 claims description 4
- 239000000243 solution Substances 0.000 abstract description 7
- 239000007787 solid Substances 0.000 description 24
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 239000004367 Lipase Substances 0.000 description 11
- 102000004882 Lipase Human genes 0.000 description 11
- 108090001060 Lipase Proteins 0.000 description 11
- 235000019421 lipase Nutrition 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 5
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 description 5
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 235000013305 food Nutrition 0.000 description 5
- 229960004488 linolenic acid Drugs 0.000 description 5
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 5
- 238000003828 vacuum filtration Methods 0.000 description 5
- 230000009471 action Effects 0.000 description 4
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 4
- 238000004458 analytical method Methods 0.000 description 4
- 230000008859 change Effects 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 3
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 239000003925 fat Substances 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 238000001640 fractional crystallisation Methods 0.000 description 3
- -1 glyceride ester Chemical class 0.000 description 3
- 235000020778 linoleic acid Nutrition 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 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
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 2
- 229940090949 docosahexaenoic acid Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 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 1
- NPDSHTNEKLQQIJ-SIGMCMEVSA-N 9-hode Chemical compound CCCCC\C=C\C=C\C(O)CCCCCCCC(O)=O NPDSHTNEKLQQIJ-SIGMCMEVSA-N 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 210000000577 adipose tissue Anatomy 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 208000011775 arteriosclerosis disease Diseases 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012159 carrier gas Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- NPDSHTNEKLQQIJ-UHFFFAOYSA-N dimorphecolic acid Natural products CCCCCC=CC=CC(O)CCCCCCCC(O)=O NPDSHTNEKLQQIJ-UHFFFAOYSA-N 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- LDHQCZJRKDOVOX-IHWYPQMZSA-N isocrotonic acid Chemical compound C\C=C/C(O)=O LDHQCZJRKDOVOX-IHWYPQMZSA-N 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 235000013622 meat product Nutrition 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- JBXYCUKPDAAYAS-UHFFFAOYSA-N methanol;trifluoroborane Chemical compound OC.FB(F)F JBXYCUKPDAAYAS-UHFFFAOYSA-N 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- JBYXPOFIGCOSSB-UQGDGPGGSA-N rumenic acid Chemical compound CCCCCC\C=C/C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-UQGDGPGGSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C11C1/007—Preparation of fatty acids from fats, fatty oils, or waxes; Refining the fatty acids using organic solvents
-
- 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
- C11C1/005—Splitting up mixtures of fatty acids into their constituents
-
- 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
-
- 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
Definitions
- the present invention relates to a method for producing a concentrate in which conjugated fatty acids cannot be purified by an ordinary fractional crystallization method.
- conjugated linoleic acid has attracted attention because it has various physiological functions such as lipid metabolism improvement, body fat lowering action, pile cancer action, hyperallergic action, and anti-arteriosclerosis action.
- Conjugated linoleic acid is a general term for 18-carbon fatty acids having one conjugated double bond, and is a kind of fatty acid contained in meat and dairy products. It is known that conjugated linoleic acid can be generally produced by an alkali conjugation method (Patent No. 3017108) using an organic solvent typified by propylene glycol.
- Synthetic linoleic acid obtained by this production method is equivalent to 9c, l lt-conjugated linoleic acid (9cis, l ltrans-conjugated linoleic acid) and 10t, 12c-conjugated linoleic acid (10trans, 12ds-conjugated linoleic acid) The resulting mixture.
- 9c 9c
- l lt-conjugated linoleic acid 9cis, l ltrans-conjugated linoleic acid
- the resulting mixture are known to have differences in physiological activity and side effects, and there is a need for a concentrate that concentrates the desired isomer.
- fractional crystallization methods distillation methods, urea addition methods, silver complex methods, enzyme (lipase) methods, and the like are known as methods for purifying fatty acids, but conjugated fatty acids generally have a high boiling point and are heated. Distillation is not suitable because of its instability.
- the urea addition method is a very useful method. It is not suitable for the use of force-purified fatty acids in food applications and is very expensive.
- the silver complex method is also very useful for unsaturated fatty acids, but it is not suitable for using purified fatty acids in food applications and is very expensive.
- the enzymatic method is very expensive and complicated.
- the fractional crystallization method is an excellent method and is widely used in general, but it is difficult to purify isomers of fatty acids with close freezing points such as conjugated fatty acids.
- a fatty acid mixture or a glyceride ester mixture containing a conjugated linoleic acid isomer mixture as a constituent in the presence of lipase may be subjected to a selective reaction for the conjugated linoleic acid isomer in a reaction system that does not contain an organic solvent.
- a method for purifying a characteristic conjugated linoleic acid isomer has been reported (for example, see Patent Document 1).
- Patent Document 2 Japanese Patent Publication No. 11-514887
- Patent Document 3 Japanese Patent Laid-Open No. 2001-169794
- Tokubori 1 0. Berdeaus, J. Voinot, E. Angioni, P. Jurneda, and J.L. Sebedio, J. Am. Oil. Chem. Soc, Vol. 75, 1749-1755 (1998).
- An object of the present invention is to provide a simple and inexpensive method capable of producing a concentrate obtained by concentrating a predetermined isomer from a conjugated fatty acid mixture that has conventionally been difficult to concentrate.
- Another object of the present invention is to provide a method for producing an ester cake using the above concentrate.
- the present invention is a method for producing a concentrate obtained by concentrating a desired isomer (a) from a conjugated fatty acid mixture (A),
- Solid-liquid separation process to obtain crystals enriched in isomer (a) or to obtain crystals enriched in isomer (a) by removing crystals with dilute isomer (a)
- a method for producing the concentrate is provided.
- the present invention provides a method for producing an esterified product characterized in that a compound having at least one alcoholic hydroxyl group in the molecule is esterified with an unsaturated fatty acid concentrate obtained by the above production method. provide.
- a concentrate obtained by concentrating a predetermined conjugated fatty acid which has been difficult to concentrate, can be produced by a very inexpensive method. Since crystallization and solvent 'unsaturated fatty acid removal only are performed, it is simple.
- the resulting concentrate can be used for food applications and was produced using the concentrate Monodallylide (MG), diglyceride (DG), and triglyceride (TG) can also be used for food applications.
- MG Monodallylide
- DG diglyceride
- TG triglyceride
- the present invention relates to a method for producing a concentrate in which a desired isomer is concentrated from a specific conjugated fatty acid mixture.
- the method of the present invention includes a step of obtaining a mixed solution in which a conjugated fatty acid mixture (A) and one or more unsaturated fatty acids (B) are mixed.
- conjugated fatty acid contained in the mixture (A) examples include conjugated linoleic acid, conjugated linolenic acid, conjugated icosapentaenoic acid, conjugated docosahexaenoic acid, styringinic acid, and dimorphecolic acid.
- it is a C-C conjugated unsaturated fatty acid, more preferably
- Examples of the unsaturated fatty acid (B) include isocrotonic acid, strong proleic acid, myristoleic acid, palmitoleic acid, oleic acid, asclebic acid, linoleic acid, and linolenic acid.
- C 8 -C unsaturated fatty acids such as myristoleic acid, palmitooleic acid, oleic acid, asclebic acid, linoleic acid and linolenic acid are preferred.
- Unsaturated fatty acids containing one cis double bond such as oleic acid, oleic acid, asclebic acid, linoleic acid and linolenic acid are more preferred. Further, oleic acid is more preferable.
- These unsaturated fatty acids (B) may be used alone or in combination of two or more. When the mixture (A) and the unsaturated fatty acid (B) l type or more are mixed, it is preferable to prepare a mixed solution in which the desired isomer (a) to be concentrated in the concentrate is dissolved. An organic solvent can also be used for mixing.
- preferred organic solvents include ketones (eg, acetone, methyl ethyl ketone, etc.), hydrocarbons (eg, hexane, petroleum ether, etc.), aromatic hydrocarbons (eg, benzene, toluene, etc.), alcohols, etc. (For example, methanol, ethanol, propanol, etc.), hydrous alcohol, ethers (for example, jetyl ether), esters (for example, ethyl acetate, etc.), and the like. Any solvent that dissolves fatty acids at normal temperature is acceptable as long as the melting point is lower than the cooling temperature. More preferred are acetone, hexane, alcohol, hydrous alcohol and the like, and most preferred is acetone.
- ketones eg, acetone, methyl ethyl ketone, etc.
- hydrocarbons eg, hexane, petroleum ether, etc.
- aromatic hydrocarbons eg, benzene, tolu
- the mixing ratio of the mixture (A) and one or more unsaturated fatty acids (B) is preferably the mixture (A) 1
- One or more unsaturated fatty acids (B) are 15 parts by mass or more with respect to 00 parts by mass. More preferably, one or more unsaturated fatty acids (B) are 20 to LOO parts by mass with respect to 100 parts by mass of the mixture (A).
- the method of the present invention is effective when the desired isomer (a) force is a conjugated fatty acid having a cis configuration at the 16th position.
- preferred unsaturated fatty acids having a cis configuration at positions 4 to 16 include conjugated linoleic acid, conjugated linolenic acid, conjugated icosapentaenoic acid, conjugated docosahexaenoic acid, styringic acid, dimorphecholine Acid, and the like. More preferred is conjugated linoleic acid, and more preferred is 9 cis, 11-trans conjugated linoleic acid.
- the method of the present invention is effective when the mixture (A) contains a conjugated fatty acid that is different from the isomer (a) in the cis configuration by 2 or more positions. Further, the method of the present invention is effective when the mixture (A) contains two or more kinds of conjugated fatty acids. It is more effective when two or more conjugated linoleic acids are included as two or more conjugated fatty acids, and two or more conjugated linoleic acids are 9 cis, 11 trans conjugated linoleic acid and 10 trans, 12 cis conjugated linoleic acid. It is most effective when it contains luric acid.
- It includes a crystallization treatment step in which crystals rich in isomer (a) are precipitated or crystals in which isomer (a) is dilute are precipitated.
- crystals rich in isomer (a) means that the content of isomer ( a , al or a2) relative to other isomers in mixture (A) is higher than that in mixture (A). Means a crystal having a high content, preferably 1.2 times or more of the content in the mixture (A), more preferably 1.3 times or more, most preferably The content is 1.5 times or more.
- a crystal in which the isomer (a) is dilute means a crystal in which the content of the isomer (a) relative to the other isomers contained in the mixture (A) is lower than that in the mixture (A).
- the content in the mixture (A) is not more than 0.8 times, more preferably not more than 0.7 times, and most preferably not more than 0.65 times. It is the content rate of.
- the crystallization method can be carried out in the same manner as that for general fats and oils and fatty acids, and a cooling crystallization method and the like can be used.
- the crystallization temperature varies depending on the type of unsaturated fatty acid to be concentrated and the saturated fatty acid to be added, the presence or absence, type, and concentration of the solvent.
- the crystallization temperature under the condition of using 3 times the amount of acetone solvent as the fractional separation condition is 4 to ⁇ 60 ° C., preferably ⁇ 10 to ⁇ 50 ° C., more preferably ⁇ 20 to ⁇ 45 ° C. In the crystallization, it is not necessary to add a solvent, but it is preferable to add an appropriate solvent.
- Examples of the solvent to be added include ketones (acetone, methyl ethyl ketone, etc.), hydrocarbons (hexane, petroleum ether, etc.), aromatic hydrocarbons (benzene, toluene, etc.), alcohols (methanol, ethanol, etc.). , Propanol, etc.), hydrous alcohol, ethers (eg, jetyl ether), esters (eg, ethyl acetate), and the like. More preferred are acetone, hexane, alcohol, hydrous alcohol and the like, and most preferred is acetone.
- the amount of the solvent to be added is 10 parts by mass or more with respect to 100 parts by mass of the mixed solution (mixture (A) + saturated fatty acid (B)), preferably 50 to: L000 parts by mass, more preferably 100 to 500 parts by mass. It is.
- the method of the present invention comprises:
- Solid-liquid separation process to obtain crystals enriched in isomer (a) or to obtain crystals enriched in isomer (a) by removing crystals with dilute isomer (a)
- the "solution rich in isomer (a)” means that the content of isomer ( a ) relative to other isomers contained in mixture (A) is higher than that in mixture (A). It means a solution having a high content, preferably 1.1 or more times the content in the mixture (A), more preferably 1.2 or more, most preferably 1. The content is more than 5 times.
- a solution in which the foreign substance (a) is dilute means that the content of the isomer (a) relative to the other isomers contained in the mixture (A) is lower than that in the mixture (A). It means a solution, preferably a content of 0.85 times or less of the content in the mixture (A), more preferably a content of 0.7 or less, most preferably 0.6 or less. It is a content rate.
- the solid-liquid separation method can be carried out in the same manner as that for general fats and oils and fatty acids, and can use a filtration method, a centrifugal separation method, a sedimentation separation method, etc. Good.
- the unsaturated fatty acids (B) and Z are removed after the solid-liquid separation treatment step.
- a step of removing the organic solvent may be included.
- the removal method can be carried out in the same manner as for ordinary fats and oils and fatty acids, and distillation method, surfactant fractionation method, chromatogram method and the like can be used. A distillation method is desirable.
- a concentrate obtained by highly concentrating a desired isomer can be obtained by repeating the above-described processing steps.
- Examples of the compound having at least one alcoholic hydroxyl group in the molecule include various compounds such as various alcohols, polyhydric alcohols and amino alcohols. Specific examples include short chain, medium chain, and long chain saturated, unsaturated, linear, branched alcohol, glycols, glycerin, and erythritols. Of these, glycerin is preferred.
- the conditions for esterification can be performed in accordance with, for example, the conditions described in JP-A Nos. 13-169795 and 15-113396.
- 0.1 to 2% by mass of lipase is added to the total mass of the substrate, ie, the total mass of the compound having an alcoholic hydroxyl group and the unsaturated fatty acid concentrate, and 24 to 30 to 60 ° C. React for 72 hours. At this time, it is preferable to carry out the reaction while reducing the pressure of the reaction system and removing water generated by esterification.
- the materials and analyzers used in this example are as follows.
- the isomeric purity used below is the amount given by the following formula.
- Isomeric purity (desired isomer amount or concentration) / (total isomer amount or concentration) The following symbols are used for the isomers of conjugated linoleic acid.
- Comparative Example 1 500 g of conjugated linoleic acid CLA-80HGR was weighed, and 1500 g of acetone was added and dissolved therein, followed by cooling at ⁇ 20 ° C. with stirring overnight. Subsequently, the solid part and the liquid part were separated by vacuum filtration, and acetone in the solid part and the liquid part was distilled off to obtain 19 g of solid part 1 and 480 g of liquid part 1. The results are shown in Table 1. There was no change in isomer purity in the solid and liquid parts, and no isomer concentrate was obtained.
- the liquid part 1 obtained in Comparative Example 1 was measured for lOg, dissolved in 30 g of acetone and then allowed to stand at ⁇ 30 ° C. Subsequently, after separation into a solid part and a liquid part by vacuum filtration, acetone in the solid part and the liquid part was distilled off to obtain 4.0 g of solid part 3 and 5.5 g of liquid part 3. The results are shown in Table 3. There was no significant change in isomer purity in the solid and liquid parts, and no isomer concentrate was obtained. It wasn't.
- Example 2 191 g of solid part 5 obtained in Example 2 was collected, and 575 g of acetone was added to prepare a mixed solution, which was cooled for 4 hours while stirring at -24 ° C. Next, the solid part and the liquid part were separated by vacuum filtration, and then acetone was distilled off to obtain 40 g of solid part 6 and 144 g of liquid part 5.
- Table 6 shows the results of isomer purity and fatty acid composition, and results of solid part 5. The isomer purity of the solid part changed significantly compared to that of the solid part 5, and the isomer purity power S of the 9cl It isomer was further improved.
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Abstract
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Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
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CN2006800094854A CN101146900B (zh) | 2005-03-30 | 2006-03-30 | 共轭脂肪酸浓缩物的制备方法 |
EP06730582A EP1865047A4 (en) | 2005-03-30 | 2006-03-30 | PROCESS FOR PRODUCING A CONCENTRATE OF A CONJUGATED FATTY ACID |
JP2007512839A JP5016483B2 (ja) | 2005-03-30 | 2006-03-30 | 共役脂肪酸濃縮物の製造方法 |
US11/902,349 US7423163B2 (en) | 2005-03-30 | 2007-09-20 | Process for producing concentrate of conjugated fatty acid |
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JP2005098770 | 2005-03-30 |
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US11/902,349 Continuation US7423163B2 (en) | 2005-03-30 | 2007-09-20 | Process for producing concentrate of conjugated fatty acid |
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US (1) | US7423163B2 (ja) |
EP (1) | EP1865047A4 (ja) |
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Citations (1)
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JPS58198423A (ja) * | 1982-05-12 | 1983-11-18 | Nippon Oil & Fats Co Ltd | 油脂の分別法 |
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US2895976A (en) * | 1956-07-09 | 1959-07-21 | Canada Packers Ltd | Process for fractionation of fatty acid mixtures |
DE69609196T3 (de) | 1995-11-14 | 2006-01-26 | Loders Croklaan B.V. | Verfahren zur Herstellung von Materialien mit hohem Gehalt an isomeren von konjugierter Linolsäure |
US6743609B1 (en) * | 1997-12-23 | 2004-06-01 | Arkion Life Sciences Llc | Linoleate isomerase |
EP1088552B1 (en) * | 1999-09-30 | 2006-04-19 | Loders Croklaan B.V. | Compositions containing pinolenic acid and its use a health component |
JP4405631B2 (ja) | 1999-12-15 | 2010-01-27 | 株式会社Adeka | 共役リノール酸異性体の精製方法 |
JP3853552B2 (ja) | 1999-12-17 | 2006-12-06 | 花王株式会社 | ジグリセリドの製造方法 |
JP3970669B2 (ja) | 2001-08-02 | 2007-09-05 | 日清オイリオグループ株式会社 | 共役脂肪酸含有モノグリセリドおよびその製造方法 |
CN1137975C (zh) * | 2001-09-25 | 2004-02-11 | 中国科学院新疆理化技术研究所 | 由脱水蓖麻油制备共轭亚油酸的方法 |
JP2004023810A (ja) | 2002-06-12 | 2004-01-22 | Nissan Motor Co Ltd | 電気自動車 |
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 |
CN1596884A (zh) * | 2004-07-22 | 2005-03-23 | 国家海洋局第一海洋研究所 | 高含量共轭亚油酸的组合物及其制备方法 |
AU2005293064B2 (en) * | 2004-10-08 | 2010-06-03 | The Nisshin Oillio Group, Ltd. | Process for producing concentrate of unsaturated fatty acid |
-
2006
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- 2006-03-30 JP JP2007512839A patent/JP5016483B2/ja not_active Expired - Fee Related
- 2006-03-30 CN CN2006800094854A patent/CN101146900B/zh not_active Expired - Fee Related
- 2006-03-30 WO PCT/JP2006/306634 patent/WO2006106809A1/ja active Application Filing
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JPS58198423A (ja) * | 1982-05-12 | 1983-11-18 | Nippon Oil & Fats Co Ltd | 油脂の分別法 |
Non-Patent Citations (2)
Title |
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See also references of EP1865047A4 * |
UEHARA ET AL.: "A Novel Method for Solvent Fractionation of Two CLA Isomers", JOURNAL OF THE AMERICAN OIL CHEMISTS' SOCIETY, vol. 83, no. 3, 2006, pages 261 - 267, XP003002298 * |
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EP1865047A1 (en) | 2007-12-12 |
JP5016483B2 (ja) | 2012-09-05 |
EP1865047A4 (en) | 2011-01-19 |
JPWO2006106809A1 (ja) | 2008-09-11 |
CN101146900B (zh) | 2012-10-03 |
CN101146900A (zh) | 2008-03-19 |
US20080027238A1 (en) | 2008-01-31 |
US7423163B2 (en) | 2008-09-09 |
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