WO2019167331A1 - 2位がパルミチン酸に富む油脂組成物の製造方法 - Google Patents
2位がパルミチン酸に富む油脂組成物の製造方法 Download PDFInfo
- Publication number
- WO2019167331A1 WO2019167331A1 PCT/JP2018/037928 JP2018037928W WO2019167331A1 WO 2019167331 A1 WO2019167331 A1 WO 2019167331A1 JP 2018037928 W JP2018037928 W JP 2018037928W WO 2019167331 A1 WO2019167331 A1 WO 2019167331A1
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- Prior art keywords
- oil
- fatty acid
- raw
- fat
- raw material
- Prior art date
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- 239000000203 mixture Substances 0.000 title claims abstract description 68
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 title claims abstract description 66
- 235000021314 Palmitic acid Nutrition 0.000 title claims abstract description 34
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 238000004519 manufacturing process Methods 0.000 title claims description 28
- 239000003925 fat Substances 0.000 claims abstract description 86
- 239000003921 oil Substances 0.000 claims abstract description 73
- 239000002994 raw material Substances 0.000 claims abstract description 61
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 59
- 229930195729 fatty acid Natural products 0.000 claims abstract description 59
- 239000000194 fatty acid Substances 0.000 claims abstract description 59
- -1 alcohol ester Chemical class 0.000 claims abstract description 38
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 38
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 claims abstract description 24
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 12
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 6
- 150000004671 saturated fatty acids Chemical class 0.000 claims abstract description 5
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 claims description 30
- 239000002253 acid Substances 0.000 claims description 27
- 238000005809 transesterification reaction Methods 0.000 claims description 26
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 22
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 20
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 20
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 20
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 20
- 239000005642 Oleic acid Substances 0.000 claims description 20
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 20
- 108090000790 Enzymes Proteins 0.000 claims description 15
- 102000004190 Enzymes Human genes 0.000 claims description 15
- 238000002156 mixing Methods 0.000 claims description 13
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052740 iodine Inorganic materials 0.000 claims description 10
- 239000011630 iodine Substances 0.000 claims description 10
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 11
- 239000013078 crystal Substances 0.000 abstract description 8
- 235000014593 oils and fats Nutrition 0.000 abstract description 4
- 230000008021 deposition Effects 0.000 abstract 1
- 235000019197 fats Nutrition 0.000 description 63
- 235000019198 oils Nutrition 0.000 description 58
- 238000000034 method Methods 0.000 description 10
- 108090001060 Lipase Proteins 0.000 description 9
- 239000004367 Lipase Substances 0.000 description 9
- 102000004882 Lipase Human genes 0.000 description 9
- 235000019421 lipase Nutrition 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 6
- 235000020256 human milk Nutrition 0.000 description 5
- 210000004251 human milk Anatomy 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 235000019482 Palm oil Nutrition 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 235000013336 milk Nutrition 0.000 description 4
- 239000008267 milk Substances 0.000 description 4
- 210000004080 milk Anatomy 0.000 description 4
- 239000002540 palm oil Substances 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 2
- 235000019486 Sunflower oil Nutrition 0.000 description 2
- 238000011437 continuous method Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 2
- 229940093471 ethyl oleate Drugs 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000002600 sunflower oil Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- 125000003203 triacylglycerol group Chemical group 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- 125000005314 unsaturated fatty acid group Chemical group 0.000 description 2
- 235000019871 vegetable fat Nutrition 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
- 241000228212 Aspergillus Species 0.000 description 1
- 108010048733 Lipozyme Proteins 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 235000019485 Safflower oil Nutrition 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 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 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products 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 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- 238000010799 enzyme reaction rate Methods 0.000 description 1
- 235000013350 formula milk Nutrition 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 229960004488 linolenic acid Drugs 0.000 description 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 description 1
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000003278 mimic effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000003346 palm kernel oil Substances 0.000 description 1
- 235000019865 palm kernel oil Nutrition 0.000 description 1
- 150000002943 palmitic acids Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- 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
-
- 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
- C11C3/003—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by esterification of fatty acids with alcohols
-
- 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
- C11C3/10—Ester interchange
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/64—Fats; Fatty oils; Ester-type waxes; Higher fatty acids, i.e. having at least seven carbon atoms in an unbroken chain bound to a carboxyl group; Oxidised oils or fats
- C12P7/6436—Fatty acid esters
- C12P7/6445—Glycerides
- C12P7/6458—Glycerides by transesterification, e.g. interesterification, ester interchange, alcoholysis or acidolysis
Definitions
- the present invention relates to a method for producing an oil-and-fat composition containing XPX triglyceride in which palmitic acid is bonded to the 2-position and X is bonded to the 1,3-position.
- X is an unsaturated fatty acid or a saturated fatty acid having 10 or less carbon atoms
- XPX is a triglyceride in which palmitic acid is bonded to the 2-position and X is bonded to the 1,3-position.
- the present invention relates to a method for producing an oil and fat composition containing 1,3-dioleoyl-2-palmitoyl triglyceride (OPO).
- OPO 1,3-dioleoyl-2-palmitoyl triglyceride
- Triacylglycerol is a major component of the lipids that make up food, and is an important nutrient for the growth of organisms and the activities of organisms.
- 1,3-dioleoyl-2-palmitoyl triglyceride (OPO) is the main fat component of lipids contained in human milk.
- the triacylglycerol structure of fats and oils contained in human milk is very characteristic, and most of the palmitic acid in the fatty acids that make up fats and oils is present in the form linked to the 2nd position, such as oleic acid at the 1st and 3rd positions. It is known that unsaturated fatty acids are bound. On the other hand, in the case of formula milk prepared by mixing vegetable oils and fats, it is known that most of palmitic acid in the fatty acids constituting the oils and fats is bonded to the 1st and 3rd positions and unsaturated fatty acids are bonded to the 2nd position. It has been.
- Non-patent Documents 1 and 2 have been widely studied that the structural differences described above bring about nutritionally important results (Non-patent Documents 1 and 2), and from these results, many of the palmitic acids constituting the fats and oils for prepared milk powder Has been desired for a long time and has been studied.
- Patent Document 1 the content of palmitic acid at the 2-position is increased by random transesterification of a fatty triglyceride using a chemical catalyst, and then enzymatically desired using a lipase that acts specifically at the 1- and 3-positions.
- a method for producing a triglyceride having a high palmitic acid content at the 2-position is disclosed, wherein the fatty acid is introduced into the 1,3-position by transesterification with a fatty acid.
- Patent Document 2 palm oil stearin containing tripalmitoyl glyceride and having an iodine value of 18 to 40 is subjected to random transesterification, and then transesterified using a 1,3-position specific lipase to place oleic acid in 1,3-position.
- a process for the production of OPO triglycerides comprising introduction into
- Patent Document 1 does not specifically limit the 2-position palmitic acid content of chemically transesterified triglyceride to be a raw oil and fat, but even the raw oil and fat with the highest 2-position palmitic acid content in the examples is 59.3.
- the object of the present invention is to provide an efficient method in which the raw material mixture and the 1,3-position specific enzyme transesterification reaction solution do not crystallize even when the temperature of the transesterification reaction is lowered, and problems such as reactor clogging do not occur. It is to provide a manufacturing method.
- raw fatty acid ester a specific raw fatty acid or a lower alcohol ester thereof (hereinafter referred to as “raw fatty acid ester”) if the 2-position palmitic acid content of the triglyceride is a raw material fat in a specific range. Etc.)), the cloud point of the raw material mixture can be reduced to 39.5 ° C. or less, and even if the temperature of the transesterification reaction is low, fat crystal precipitation does not occur, and the fat composition contains XPX triglyceride.
- the present inventors have found that a product can be efficiently manufactured and completed the present invention.
- the present invention (1) In a method for producing an oil and fat composition in which a raw material mixture obtained by mixing raw oil and fat and raw fatty acid or a lower alcohol ester thereof is subjected to 1,3-position specific enzyme transesterification, the raw material oil or fat has a 2-position palmitic acid content of 60 to 90% by weight.
- XPX triglyceride characterized in that the fatty acid constituting the raw fatty acid or its lower alcohol ester is X, and the cloud point of the raw material mixture and the 1,3-position specific enzyme transesterification reaction solution is 39.5 ° C. or lower
- the manufacturing method of the oil-fat composition containing this.
- X unsaturated fatty acid or saturated fatty acid having 10 or less carbon atoms
- XPX triglyceride in which palmitic acid is bonded to the 2nd position and X is bonded to the 1st and 3rd positions
- the fat or oil containing at least one kind of palm stearin is a random ester
- the method for producing an oil / fat composition according to (1) which is an oil / fat having an iodine value of 6 or more and less than 18 which is exchanged.
- (3) The manufacturing method of the oil-fat composition of (1) whose fatty acid which comprises the said raw material fatty acid or its lower alcohol ester is unsaturated fatty acid.
- XPX triglyceride The present invention relates to a method for producing an oil-and-fat composition containing XPX triglyceride in which palmitic acid is bonded to the 2-position and X is bonded to the 1,3-position.
- the fatty acids X bonded to the 1- and 3-positions of XPX may be the same or different.
- XPX triglyceride contains triglyceride (OPO) with palmitic acid at the 2-position and oleic acid at the 1,3-position, palmitic acid at the 2-position, oleic acid at one of the 1,3-positions, and DHA at the other. Also included triglycerides.
- the raw material fat used in the present invention is required to have a 2-position palmitic acid content of triglyceride of 60 to 90% by weight, preferably 70% by weight or more, more preferably 76% by weight or more, and further preferably 78% by weight or more. It is. Further, it is preferably 88% by weight or less, more preferably 85% by weight or less, and still more preferably 83% by weight or less. If the 2-position palmitic acid content is within this range, an oil / fat composition containing XPX triglyceride can be produced efficiently, and the cloud point of the raw material mixture does not become too high.
- the raw oil and fat used in the present invention is not particularly limited as long as the 2-position palmitic acid content is in the above range, but palm oil, soybean oil, rapeseed oil, corn oil, cottonseed oil, peanut oil, sunflower oil, rice oil, safflower oil , Vegetable oils such as safflower oil, olive oil, sesame oil, coconut oil, palm kernel oil, and animal fats such as beef tallow, pork tallow, and processed fats and oils that have been subjected to transesterification, fractionation, hydrogenation, etc., or these Can be mentioned.
- the fats and oils which carried out random transesterification of the fats and oils containing at least 1 type of palm stearin are suitable, and the iodine value is further more preferable in it being 6 or more and less than 18. Further, it is preferably 8 or more, more preferably 10 or more, still more preferably 12 or more, preferably 17 or less, more preferably 16 or less, and still more preferably 15 or less.
- the two or more types of palm stearin and palm oil of different quality, palm fractionation oils, such as a palm middle melting point, and the random transesterification oil of fats and oils other than palm related fats and oils were mix
- Examples of the random transesterification include a method using a chemical catalyst such as sodium methylate and a method using a lipase having no position specificity as a catalyst. If the cloud point of oils and fats is relatively high, a method using a chemical catalyst may be used. preferable. Further, hydrogenation may be performed before or after the transesterification. In this case, it is possible to obtain an oil / fat composition rich in the stearic acid content as well as the palmitic acid content at the 2-position.
- the raw material fat used in the present invention preferably has an acid value of 2 or less. More preferably, it is 1 or less, more preferably 0.5 or less, and most preferably 0.3 or less. An acid value of 2 or less is preferred because the cloud point of the raw material mixture is lowered.
- the fatty acid which comprises the raw material fatty acid ester etc. which are used in this invention needs to be a C10 or less saturated fatty acid and unsaturated fatty acid.
- unsaturated fatty acids are preferred, and specific examples include oleic acid, linoleic acid, linolenic acid, DHA, EPA, and the like.
- oleic acid is more preferable because it provides an oil and fat composition containing OPO triglyceride known to be contained in a large amount in human milk, and thus has high utility value as a raw oil and fat such as prepared milk powder.
- the fatty acid lower alcohol ester of the present invention is not defined as long as it is an ester of a fatty acid and an alcohol having 1 to 6 carbon atoms, preferably an alcohol having 1 to 3 carbon atoms. More preferred is ethanol.
- the fatty acid constituting the raw material fatty acid ester or the like used in the present invention may be a mixture of a plurality of fatty acid species, but may contain a single fatty acid with a purity of 50% by weight or more.
- the purity is preferably 60% by weight or more, more preferably 70% by weight or more, and still more preferably 80% by weight or more.
- the oleic acid content when the fatty acid constituting the raw material fatty acid ester or the like is oleic acid is not particularly specified, but is preferably 70% by weight or more, more preferably 75% by weight or more, and still more preferably 80% by weight or more. is there.
- the palmitic acid content in this case is not particularly specified, but is preferably 10% by weight or less, more preferably 8% by weight or less, and further preferably 5% by weight or less.
- the raw material of oleic acid or oleic acid lower alcohol ester is not defined as long as it is a vegetable oil that matches the above composition, and preferably has a high oleic acid content such as high oleic sunflower oil or high oleic soybean oil. It ’s fine.
- a single free fatty acid or a single lower alcohol ester can be used, but a mixture thereof may also be used.
- the acid value is preferably 70 or less, preferably 50 or less, more preferably 30 or less, still more preferably 20 or less, and most preferably 10 or less.
- the acid value is 70 or less, that is, the proportion of the lower alcohol ester is large, the cloud point of the raw material mixture tends to be low, which is preferable.
- the cloud point of the raw material mixture in the present invention and the 1,3-position specific enzyme transesterification reaction solution during and after the reaction must be 39.5 ° C. or lower. Further, it is preferably 39 ° C. or lower, more preferably 38 ° C. or lower, still more preferably 35 ° C. or lower, and most preferably 30 ° C. or lower.
- the mixing ratio of the raw material mixture is preferably 5/95 to 40/60 by weight. More preferably, it is 10/90 or more, and further preferably 15/85 or more. Further, it is more preferably 25/75 or less, further preferably 30/70 or less, and most preferably 35/65 or less.
- the mixing ratio of the raw material mixture is less than 5/95, the production amount of the oil / fat composition per raw material mixture is small, and the production efficiency tends to deteriorate. If it exceeds 40/60, the cloud point tends to be too high.
- a lipase produced by a microorganism belonging to the genus Rhizopus, Aspergillus, or Mucor can be used in the transesterification reaction at the 1,3-position specific enzyme. Any other lipase having the same properties as these may be used other than those described above.
- Such lipases are commercially available.
- Amano A manufactured by Amano Pharmaceutical Co., Ltd.
- lipozyme manufactured by NOVOZYMES
- the use form of the lipase is not particularly limited, but it is preferably used after being immobilized on a carrier by a known method from the viewpoint of efficiency.
- This reaction can be carried out by a batch method using a stirring tank or a continuous method using a packed reactor.
- a continuous method using a packed reactor there are concerns about clogging due to crystal precipitation of the raw material mixture. Since it is eliminated by the invention, it is particularly preferable.
- the temperature of the enzyme reaction is 30 to 90 ° C. from the viewpoint of maintaining the enzyme activity for a long time while ensuring a sufficient enzyme reaction rate, from the viewpoint of avoiding the precipitation of fat crystals during the reaction, and from the viewpoint of suppressing the generation of isomeric triglycerides as much as possible.
- the temperature is more preferably 35 to 75 ° C, and still more preferably 40 to 55 ° C.
- the temperature is desirably at least 5 ° C. higher than the cloud point of the raw material mixture.
- the enzyme reaction time is not particularly limited as long as a sufficient transesterification rate can be achieved, but 2 hours to 4 days is preferable.
- the method for separating and removing fatty acid esters and the like from the 1,3-position specific enzyme transesterification reaction solution is not particularly limited, but distillation can be used. Moreover, the oil-and-fat composition containing XPX triglyceride obtained as a triglyceride fraction can raise the purity by fractionation.
- the cloud point is measured by the following method according to the oil and fat standard analysis method 2.2.7-1996. 1. 4.0 g of sample is weighed into a small test tube and completely dissolved in a warm bath (over 60 ° C. for 15 minutes). 2. Set 1 small test tube to the large test tube and move it to the measuring bath (60 ° C setting). 3. When the oil reaches 60 ° C., cooling starts. The cooling rate is 0.25 to 0.3 ° C./min. The crystal precipitation is confirmed visually, and the temperature is taken as the cloud point. In the present invention, a cloud point of 39.5 ° C. or lower is accepted, and if it exceeds that, it is rejected.
- Example 1 After adding 0.15 wt% sodium methylate to palm stearin (iodine value 14.2) and conducting random transesterification reaction at 80 ° C for 30 minutes, washing with water according to a conventional method, palm stearin random ester An exchange oil was obtained.
- This oil / fat had a 2-position palmitic acid content of 80% by weight and an acid value of 0.24.
- 20 parts by weight of the fats and oils as raw material fats and 80 parts by weight of ethyl oleate (oleic acid content of constituent fatty acids 84 wt%, acid value 8.8) as raw material fatty acid esters were mixed to obtain a raw material mixture.
- the cloud point of the raw material mixture was 26.0 ° C. and passed.
- the ester exchange reaction was carried out by passing the solution through a fixed bed reactor filled with 1.3-position specific lipase. After the reaction, the obtained reaction solution was separated into a triglyceride fraction and a fatty acid fraction by distillation.
- the fatty acid composition of the obtained triglyceride fraction is such that the content of palmitic acid in the total fatty acid is 36% by weight and the content of palmitic acid in the 2-position bonded fatty acid is 76% by weight. there were.
- Example 2 As a raw material fatty acid ester or the like, ethyl oleate (purity 80% by weight, acid value 8.8) and oleic acid (purity 80% by weight, acid value 198.0) are mixed to prepare a mixture having a specific acid value, Sample A having a value of 198.0 (oleic acid alone), Sample B having an acid value of 50.0, Sample C having an acid value of 30.0, Sample D having an acid value of 20.0, and Sample E having an acid value of 8.8 were obtained. It was.
- Samples A to E such as raw material fatty acid esters are 15/85, 20/80, 25/75, and 30/85 of palm stearin random transesterified oil and raw oil / fat / raw fatty acid ester obtained in Example 1.
- the raw material mixture was adjusted to 70, 40/60, 41.5 / 58.5, and the cloud point was measured. The results are shown in Table 1.
- the cloud point tended to increase as the raw material mixing ratio increased, and the cloud point tended to decrease as the acid value of the raw material fatty acid ester decreased, that is, as the purity of the ethyl ester increased. Also, a mixture of 41.5 / 58.5 of a random transesterified oil of palm stearin (iodine value 14.2) and a sample A (oleic acid alone) having an acid value of 198.0 has a cloud point of 40.0 ° C and is rejected. However, all of the cloud points of the other mixtures were 39.5 ° C. or lower and passed.
- Example 3 A palm stearin random transesterified oil was obtained in the same manner as in Example 1 except that palm stearin having an iodine value of 17.5 was used, and used as a raw oil.
- a raw material fatty acid ester, etc. a sample A having an acid value of 198.0 (oleic acid alone) was used, a raw material mixture was prepared so that the raw material fat / raw material fatty acid ester, etc. became 40/60, and the cloud point was measured. However, it was 36.0 ° C. and passed.
- Example 4 A palm stearin random transesterified oil was obtained in the same manner as in Example 1 except that palm stearin having an iodine value of 6.0 was used, and used as a raw oil. Further, as a raw material fatty acid ester and the like, sample A having an acid value of 198.0 (oleic acid alone), sample B having an acid value of 50.0, and sample E having an acid value of 8.8 were obtained in the same manner as in Example 2. Prepare raw material fats and fats and raw materials fatty acid ester samples A, B and E, adjust the raw material mixture so that the raw material fats and fats / raw fatty acid esters are 25/75, 30/70, 40/60, and measure the cloud point did. The results are shown in Table 2.
- the cloud point tended to increase as the raw material mixing ratio increased, and the cloud point tended to decrease as the acid value of the raw material fatty acid ester decreased, that is, as the purity of the ethyl ester increased.
- a mixture of a random transesterified oil of palm stearin (iodine value 6.0) and a sample A (oleic acid alone) having an acid value of 198.0 has a cloud point of 40.9 ° C. when the raw material mixing ratio is 40/60. Although it was rejected, it was 39.0 ° C. in the case of a mixture with Sample B having an acid value of 50.0.
- the raw material mixing ratio was 25/70, 30/70, all passed.
- the present invention in the 1,3-position enzyme transesterification step in OPO fat production, a smooth reaction step without crystal precipitation is possible even when raw material fat with a high 2-position palmitic acid content and a high cloud point is used. High-quality OPO fat production has become possible.
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Abstract
Description
また前述の構造上の差異は、栄養学的に重要な結果をもたらすことが広く研究されており(非特許文献1、2)、これらの結果から、調製粉乳用油脂を構成するパルミチン酸の多くを2位に結合した油脂へと改変することが古くより望まれ、検討が実施されてきた。
また結晶析出を避けるためエステル交換反応の温度を比較的高く設定すると酵素触媒の反復使用における活性の低下が起こり、酵素触媒のコストが増加する問題が懸念された。
本発明の目的は、エステル交換反応の温度を低くしても原料混合物及び反応中の1,3位特異酵素エステル交換反応液が結晶析出せず、反応器閉塞等の問題が起こらない効率的な製造方法を提供することにある。
(1)原料油脂と原料脂肪酸又はその低級アルコールエステルを混合した原料混合物を1,3位特異酵素エステル交換する油脂組成物の製造方法において、原料油脂の2位パルミチン酸含量が60~90重量%であり、原料脂肪酸又はその低級アルコールエステルを構成する脂肪酸がXであり、原料混合物及び1,3位特異酵素エステル交換反応液の曇り点が39.5℃以下であることを特徴とするXPXトリグリセリドを含む油脂組成物の製造方法。
ただしX:不飽和脂肪酸又は炭素数10以下の飽和脂肪酸
XPX:2位にパルミチン酸、1,3位にXが結合したトリグリセリド
(2)前記原料油脂が少なくとも一種のパームステアリンを含む油脂をランダムエステル交換した、ヨウ素価6以上18未満の油脂である(1)の油脂組成物の製造方法。
(3)前記原料脂肪酸又はその低級アルコールエステルを構成する脂肪酸が不飽和脂肪酸である(1)の油脂組成物の製造方法。
(4)前記不飽和脂肪酸がオレイン酸である(3)の油脂組成物の製造方法。
(5)前記原料混合物の混合比(原料油脂/原料脂肪酸又はその低級アルコールエステル)が、重量比で5/95~40/60である(1)の油脂組成物の製造方法。
(6)前記原料脂肪酸又はその低級アルコールエステルの酸価が70以下である(1)の油脂組成物の製造方法。
(7)前記原料油脂の酸価が2以下である(1)の油脂の製造方法。
に関するものである。
本発明は、2位にパルミチン酸、1,3位にXが結合したXPXトリグリセリドを含む油脂組成物の製造方法に関する。XPXの1,3位に結合する脂肪酸Xは同一であっても異なっていても良い。例えばXPXトリグリセリドは、2位にパルミチン酸、1,3位にオレイン酸が結合したトリグリセリド(OPO)を含むし、2位にパルミチン酸、1,3位の一方にオレイン酸、他方にDHAが結合したトリグリセリドをも含む。
本発明において使用する原料油脂は、トリグリセリドの2位パルミチン酸含量が60~90重量%である必要があり、好ましくは70重量%以上、より好ましくは76重量%以上、更に好ましくは78重量%以上である。また好ましくは88重量%以下、より好ましくは85重量%以下、更に好ましくは83重量%以下である。
2位パルミチン酸含量がこの範囲にあればXPXトリグリセリドを含む油脂組成物を効率的に製造でき、しかも原料混合物の曇り点が高くなりすぎない。
本発明において使用する原料油脂は、2位パルミチン酸含量が前記の範囲であれば特に限定されないが、パーム油、大豆油、菜種油、コーン油、綿実油、落花生油、ひまわり油、こめ油、ベニバナ油、サフラワー油、オリーブ油、ゴマ油、ヤシ油、パーム核油等の植物油脂及び牛脂、豚脂等の動物脂、並びにこれらをエステル交換、分別、水素添加等を施した加工油脂の単品又は、これらの組み合わせ油脂を挙げることができる。そして前記原料油脂としては、少なくとも一種のパームステアリンを含む油脂をランダムエステル交換した油脂が好適であり、そのヨウ素価は6以上18未満であると更に好適である。また好ましくは8以上、より好ましくは10以上、更に好ましくは12以上、また好ましくは17以下、より好ましくは16以下、更に好ましくは15以下である。また前記原料油脂としては、異なる品質の二種以上のパームステアリンやパーム油、パーム中融点等のパーム分別油、パーム関連油脂以外の油脂を配合した油脂のランダムエステル交換油であっても良い。
前記ランダムエステル交換はナトリウムメチラート等の化学触媒を用いる方法や位置特異性のないリパーゼを触媒として用いる方法が挙げられるが、油脂の曇り点が比較的高くなる場合は、化学触媒を用いる方法が好ましい。
また前記エステル交換の前又は後に、水素添加を実施しても構わない。この場合は、2位のパルミチン酸含量はもとよりステアリン酸含量にも富む油脂組成物を得ることができる。
本発明において使用する原料油脂は、酸価が2以下であることが好ましい。またより好ましくは1以下、更に好ましくは0.5以下、最も好ましくは0.3以下である。
酸価が2以下であると原料混合物の曇り点が低くなるため好ましい。
本発明において使用する原料脂肪酸エステル等を構成する脂肪酸は炭素数10以下の飽和脂肪酸や不飽和脂肪酸である必要がある。また特に不飽和脂肪酸が好ましく、具体的にはオレイン酸,リノール酸,リノレン酸,DHA,EPA等が例示される。また特にオレイン酸であれば、人乳中に多く含まれることが知られているOPOトリグリセリドを含む油脂組成物が得られるので調製粉乳などの原料油脂として利用価値が高くより好ましい。
本発明の脂肪酸低級アルコールエステルは脂肪酸と炭素数1~6のアルコールとのエステルであればなんら規定されず、好ましくは炭素数1~3のアルコールが良い。更に好ましくはエタノールが良い。
本発明において使用する原料脂肪酸エステル等を構成する脂肪酸は、複数の脂肪酸種の混合物でも良いが単一の脂肪酸を純度50重量%以上含むものでも良い。又その純度は好ましくは60重量%以上、より好ましくは70重量%以上、更に好ましくは80重量%以上である。
原料脂肪酸エステル等を構成する脂肪酸がオレイン酸の場合のオレイン酸含量は特に規定はしないが、70重量%以上であることが好ましく、より好ましくは75重量%以上、更に好ましくは80重量%以上である。またこの場合のパルミチン酸含量は、特に規定はしないが、10重量%以下であることが好ましく、より好ましくは8重量%以下、さらに好ましくは5重量%以下である。またオレイン酸又はオレイン酸低級アルコールエステルの原料は、前記の組成に合致した植物油脂であればなんら規定されず、好ましくはハイオレイックヒマワリ油やハイオレイック大豆油等のオレイン酸含量が高いものであれば良い。
本発明において使用する原料脂肪酸エステル等は、遊離脂肪酸単品又は低級アルコールエステル体単品を使用することができるが、それらの混合物であっても良い。混合物の場合は、酸価が70以下であることが好ましく、好ましくは50以下、より好ましくは30以下、更に好ましくは20以下、最も好ましくは10以下である。
酸価が70以下すなわち低級アルコールエステルの割合が多いと原料混合物の曇り点が低くなる傾向があり好ましい。
本発明における原料混合物並びに反応中及び反応後の1,3位特異酵素エステル交換反応液の曇り点は39.5℃以下である必要がある。また好ましくは39℃以下、より好ましくは38℃以下、更に好ましくは35℃以下、最も好ましくは30℃以下である。
本発明における原料混合物の混合比(原料油脂/原料脂肪酸エステル等)は、重量比で5/95~40/60であることが好ましい。またより好ましくは10/90以上、更に好ましくは15/85以上である。またより好ましくは25/75以下、更に好ましくは30/70以下、最も好ましくは35/65以下である。
原料混合物の混合比が5/95未満であると原料混合物あたりの油脂組成物の製造量が少なく、生産効率が悪くなる傾向がある。また40/60を超えると曇り点が高くなりすぎる傾向がある。
1,3位特異酵素エステル交換反応にはリゾプス(Rhizopus)属、アスペルギルス(Aspergillus)属、ムコール(Mucor)属の微生物が生産するリパーゼを使用することができる。また、少なくともこれらと同様な性質をもつリパーゼであれば上記以外のものでもよく、何ら差支えない。このようなリパーゼは市販されており、例えばアマノA(天野製薬社製)、リポザイム(NOVOZYMES社製)などが用いられる。上記リパーゼの使用形態は、特に制限されないが、効率の観点から公知の方法で担体に固定化して用いることが好ましい。またこの反応は、撹拌タンクを用いた回分法や、充填反応器を用いた連続法で実施できるが、充填反応器を用いる連続法の場合には原料混合物の結晶析出による閉塞などの懸念が本発明により解消されるので特に好ましい。
酵素反応の温度は、十分な酵素反応速度を確保しつつ酵素活性を長く維持する観点、反応中に油脂結晶の析出を避ける観点及び異性体トリグリセリドの生成をできるだけ抑制する観点から、30~90℃であることが望ましく、35~75℃であることがより好ましく、40~55℃であることがさらに好ましい。また反応中に油脂結晶の析出を避ける観点からは、原料混合物の曇り点よりも少なくとも5℃以上高い温度であることが望ましい。
酵素反応の時間は十分なエステル交換反応率が達成できれば特に限定されないが2時間から4日間が好適である。
1,3位特異酵素エステル交換反応液からの脂肪酸エステル等の分離除去の方法は特に限定されないが、蒸留を用いることができる。またトリグリセリド画分として得られたXPXトリグリセリドを含む油脂組成物は分別によりその純度を高めることができる。
本発明において曇り点は、油脂基準分析法2.2.7-1996に準じた以下の方法で測定される。
1. サンプル4.0gを小試験管に計量し、温浴(60℃以上で15分)で完全溶解させる。
2. 1の小試験管を大試験管にセットし、測定用温浴(60℃設定)に移動させる。
3. 油脂が60℃に達したら冷却開始する。冷却速度は0.25~0.3℃/分
4. 目視にて結晶析出を確認し、その温度を曇り点とする。
本発明においては、曇り点が39.5℃以下を合格とし、それを超えると不合格とする。
パームステアリン(ヨウ素価14.2)に対油0.15重量%のナトリウムメチラートを添加し、80℃にて30分ランダムエステル交換反応を実施した後、常法に従い水洗し、パームステアリンランダムエステル交換油を得た。本油脂の2位パルミチン酸含量は80重量%、酸価は0.24であった。本油脂を原料油脂として20重量部と、オレイン酸エチル(構成脂肪酸中オレイン酸含量84重量%、酸価8.8)を原料脂肪酸エステル等として80重量部を混合して原料混合物を得た。原料混合物の曇り点は26.0℃であり合格であった。この原料混合物を45℃に維持しながら、1.3位特異性リパーゼを充填した固定床反応装置に通液することでエステル交換反応を実施した。反応後、得られた反応液をトリグリセリド画分と脂肪酸画分に蒸留により分離した。得られたトリグリセリド画分の脂肪酸組成は、全脂肪酸中のパルミチン酸含量が36重量%、2位結合脂肪酸中のパルミチン酸含量が76重量%であり、調製粉乳用油脂として相応しい組成を有するものであった。
原料脂肪酸エステル等として、オレイン酸エチル(純度80重量%、酸価8.8)とオレイン酸(純度80重量%、酸価198.0)を混合して特定酸価の混合物を調整し、酸価198.0の試料A(オレイン酸単品)、酸価50.0の試料B 、酸価30.0の試料C、酸価20.0の試料D、酸価8.8の試料Eを得た。
これら原料脂肪酸エステル等の試料A~Eを実施例1で得られた原料油脂のパームステアリンランダムエステル交換油と原料油脂/原料脂肪酸エステル等が15/85,20/80,25/75,30/70,40/60、41.5/58.5となるように原料混合物を調整し、その曇り点を測定した。結果を表1に示す。
ヨウ素価17.5のパームステアリンを用いた以外は実施例1と同様にしてパームステアリンランダムエステル交換油を得、原料油脂として用いた。
また原料脂肪酸エステル等として、酸価198.0の試料A(オレイン酸単品)を用い、原料油脂/原料脂肪酸エステル等が40/60となるように原料混合物を調製し、その曇り点を測定したところ36.0℃であり、合格であった。
ヨウ素価6.0のパームステアリンを用いた以外は実施例1と同様にしてパームステアリンランダムエステル交換油を得、原料油脂として用いた。
また原料脂肪酸エステル等として、実施例2と同様にして酸価198.0の試料A(オレイン酸単品)、酸価50.0の試料B、酸価8.8の試料Eを得た。
これら原料油脂と原料脂肪酸エステル等の試料A、B,Eを原料油脂/原料脂肪酸エステル等が25/75,30/70,40/60となるように原料混合物を調整し、その曇り点を測定した。結果を表2に示す。
Claims (7)
- 原料油脂と原料脂肪酸又はその低級アルコールエステルを混合した原料混合物を1,3位特異酵素エステル交換する油脂組成物の製造方法において、原料油脂の2位パルミチン酸含量が60~90重量%であり、原料脂肪酸又はその低級アルコールエステルを構成する脂肪酸がXであり、原料混合物及び1,3位特異酵素エステル交換反応液の曇り点が39.5℃以下であることを特徴とするXPXトリグリセリドを含む油脂組成物の製造方法。
ただしX:不飽和脂肪酸又は炭素数10以下の飽和脂肪酸
XPX:2位にパルミチン酸、1,3位にXが結合したトリグリセリド - 前記原料油脂が少なくとも一種のパームステアリンを含む油脂をランダムエステル交換した、ヨウ素価6以上18未満の油脂である請求項1に記載の油脂組成物の製造方法。
- 前記原料脂肪酸又はその低級アルコールエステルを構成する脂肪酸が不飽和脂肪酸である請求項1に記載の油脂組成物の製造方法。
- 前記不飽和脂肪酸がオレイン酸である請求項3に記載の油脂組成物の製造方法。
- 前記原料混合物の混合比(原料油脂/原料脂肪酸又はその低級アルコールエステル)が、5/95~40/60である請求項1に記載の油脂組成物の製造方法。
- 前記原料脂肪酸又はその低級アルコールエステルの酸価が70以下である請求項1に記載の油脂組成物の製造方法。
- 前記原料油脂の酸価が2以下である請求項1に記載の油脂の製造方法。
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CN201880090521.7A CN111787807A (zh) | 2018-03-02 | 2018-10-11 | 2位富含棕榈酸的油脂组合物的制造方法 |
JP2018554121A JP6593551B1 (ja) | 2018-03-02 | 2018-10-11 | 2位がパルミチン酸に富む油脂組成物の製造方法 |
CA3092876A CA3092876A1 (en) | 2018-03-02 | 2018-10-11 | Production method for oil/fat composition rich in palmitic acid at position 2 |
EP18908159.9A EP3750405A4 (en) | 2018-03-02 | 2018-10-11 | PROCESS FOR THE PRODUCTION OF OIL / FAT COMPOSITION RICH IN PALMITIC ACID AT POSITION 2 |
US16/976,549 US20210002681A1 (en) | 2018-03-02 | 2018-10-11 | Production method for oil/fat composition rich in palmitic acid at position 2 |
SG11202008310VA SG11202008310VA (en) | 2018-03-02 | 2018-10-11 | Production method for oil/fat composition rich in palmitic acid at position 2 |
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CA3092876A1 (en) | 2019-09-06 |
KR102401871B1 (ko) | 2022-05-25 |
JP6593551B1 (ja) | 2019-10-23 |
US20210002681A1 (en) | 2021-01-07 |
EP3750405A1 (en) | 2020-12-16 |
CN111787807A (zh) | 2020-10-16 |
SG11202008310VA (en) | 2020-09-29 |
JP2019214740A (ja) | 2019-12-19 |
KR20200125613A (ko) | 2020-11-04 |
EP3750405A4 (en) | 2020-12-16 |
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