WO2005005586A1 - 対称型トリグリセリドの製造方法 - Google Patents
対称型トリグリセリドの製造方法 Download PDFInfo
- Publication number
- WO2005005586A1 WO2005005586A1 PCT/JP2004/009307 JP2004009307W WO2005005586A1 WO 2005005586 A1 WO2005005586 A1 WO 2005005586A1 JP 2004009307 W JP2004009307 W JP 2004009307W WO 2005005586 A1 WO2005005586 A1 WO 2005005586A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- reaction
- chain fatty
- fatty acid
- medium
- triglyceride
- Prior art date
Links
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 title claims abstract description 212
- 238000000034 method Methods 0.000 title claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 221
- 150000004667 medium chain fatty acids Chemical class 0.000 claims abstract description 165
- 150000004668 long chain fatty acids Chemical class 0.000 claims abstract description 129
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 116
- 150000003626 triacylglycerols Chemical class 0.000 claims abstract description 51
- 108090000790 Enzymes Proteins 0.000 claims abstract description 49
- 102000004190 Enzymes Human genes 0.000 claims abstract description 49
- 239000000194 fatty acid Substances 0.000 claims abstract description 47
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 46
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 46
- 229930195729 fatty acid Natural products 0.000 claims abstract description 46
- 239000000126 substance Substances 0.000 claims abstract description 45
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 44
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 32
- 239000003054 catalyst Substances 0.000 claims abstract description 23
- 239000000470 constituent Substances 0.000 claims abstract description 23
- 238000004519 manufacturing process Methods 0.000 claims description 56
- 239000002994 raw material Substances 0.000 claims description 48
- 108090001060 Lipase Proteins 0.000 claims description 33
- 239000004367 Lipase Substances 0.000 claims description 33
- 102000004882 Lipase Human genes 0.000 claims description 33
- 235000019421 lipase Nutrition 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 24
- -1 medium-chain fatty acid triglycerides Chemical class 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- 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 claims description 16
- 239000000047 product Substances 0.000 claims description 15
- 238000006911 enzymatic reaction Methods 0.000 claims description 14
- 239000002245 particle Substances 0.000 claims description 13
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 13
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 13
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 9
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 8
- 150000002148 esters Chemical group 0.000 claims description 7
- 239000000376 reactant Substances 0.000 claims description 6
- 229940057917 medium chain triglycerides Drugs 0.000 claims description 4
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 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 claims description 2
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 2
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 2
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 claims 1
- YYZUSRORWSJGET-UHFFFAOYSA-N ethyl octanoate Chemical compound CCCCCCCC(=O)OCC YYZUSRORWSJGET-UHFFFAOYSA-N 0.000 description 73
- 238000004821 distillation Methods 0.000 description 63
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 30
- 229940093609 tricaprylin Drugs 0.000 description 26
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 26
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 description 17
- OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 16
- 239000002253 acid Substances 0.000 description 15
- ITNKVODZACVXDS-YNUSHXQLSA-N ethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosahexaenoate Chemical compound CCOC(=O)CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC ITNKVODZACVXDS-YNUSHXQLSA-N 0.000 description 13
- 229920000064 Ethyl eicosapentaenoic acid Polymers 0.000 description 12
- SSQPWTVBQMWLSZ-AAQCHOMXSA-N ethyl (5Z,8Z,11Z,14Z,17Z)-icosapentaenoate Chemical compound CCOC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CC SSQPWTVBQMWLSZ-AAQCHOMXSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000003921 oil Substances 0.000 description 11
- 235000019198 oils Nutrition 0.000 description 11
- 239000010409 thin film Substances 0.000 description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 10
- 238000000199 molecular distillation Methods 0.000 description 10
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 9
- 125000004494 ethyl ester group Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 8
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 8
- 239000005642 Oleic acid Substances 0.000 description 8
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 8
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 8
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 8
- 150000004671 saturated fatty acids Chemical class 0.000 description 8
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 6
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 6
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 6
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 6
- 229940093471 ethyl oleate Drugs 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 108010048733 Lipozyme Proteins 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000006297 dehydration reaction Methods 0.000 description 5
- 235000011187 glycerol Nutrition 0.000 description 5
- FCCDDURTIIUXBY-UHFFFAOYSA-N lipoamide Chemical compound NC(=O)CCCCC1CCSS1 FCCDDURTIIUXBY-UHFFFAOYSA-N 0.000 description 5
- 235000003441 saturated fatty acids Nutrition 0.000 description 5
- 239000008117 stearic acid Substances 0.000 description 5
- 235000021355 Stearic acid Nutrition 0.000 description 4
- 235000019486 Sunflower oil Nutrition 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 230000006837 decompression Effects 0.000 description 4
- 230000018044 dehydration Effects 0.000 description 4
- 239000003925 fat Substances 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 238000005194 fractionation Methods 0.000 description 4
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 4
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 4
- 239000002600 sunflower oil Substances 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 244000299461 Theobroma cacao Species 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 235000014593 oils and fats Nutrition 0.000 description 3
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical class C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000004347 Perilla Nutrition 0.000 description 2
- 244000124853 Perilla frutescens Species 0.000 description 2
- 235000019484 Rapeseed oil Nutrition 0.000 description 2
- 241000235403 Rhizomucor miehei Species 0.000 description 2
- 235000019485 Safflower oil Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 235000009470 Theobroma cacao Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000010495 camellia oil Substances 0.000 description 2
- 235000012343 cottonseed oil Nutrition 0.000 description 2
- 239000002385 cottonseed oil Substances 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- 235000021323 fish oil Nutrition 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 125000005473 octanoic acid group Chemical group 0.000 description 2
- 235000021313 oleic acid Nutrition 0.000 description 2
- 235000005713 safflower oil Nutrition 0.000 description 2
- 239000003813 safflower oil Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000002699 waste material Substances 0.000 description 2
- BITHHVVYSMSWAG-KTKRTIGZSA-N (11Z)-icos-11-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCC(O)=O BITHHVVYSMSWAG-KTKRTIGZSA-N 0.000 description 1
- LGHXTTIAZFVCCU-SSVNFBSYSA-N (2E,4E,6E,8E)-octadeca-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O LGHXTTIAZFVCCU-SSVNFBSYSA-N 0.000 description 1
- BBWMTEYXFFWPIF-CJBMEHDJSA-N (2e,4e,6e)-icosa-2,4,6-trienoic acid Chemical compound CCCCCCCCCCCCC\C=C\C=C\C=C\C(O)=O BBWMTEYXFFWPIF-CJBMEHDJSA-N 0.000 description 1
- DVSZKTAMJJTWFG-SKCDLICFSA-N (2e,4e,6e,8e,10e,12e)-docosa-2,4,6,8,10,12-hexaenoic acid Chemical compound CCCCCCCCC\C=C\C=C\C=C\C=C\C=C\C=C\C(O)=O DVSZKTAMJJTWFG-SKCDLICFSA-N 0.000 description 1
- YUFFSWGQGVEMMI-JLNKQSITSA-N (7Z,10Z,13Z,16Z,19Z)-docosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCCCC(O)=O YUFFSWGQGVEMMI-JLNKQSITSA-N 0.000 description 1
- 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
- ATNNLHXCRAAGJS-QZQOTICOSA-N (e)-docos-2-enoic acid Chemical compound CCCCCCCCCCCCCCCCCCC\C=C\C(O)=O ATNNLHXCRAAGJS-QZQOTICOSA-N 0.000 description 1
- LKZDFKLGDGSGEO-UHFFFAOYSA-N 2',8-Di-Me ether,7-O-beta-D-glucuronoside-2',5,7,8-Tetrahydroxyflavone Natural products OC1C(O)C(O)C(CO)OC1OC1C(OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=CC(O)=CC=2)=O)OC(CO)C(O)C1O LKZDFKLGDGSGEO-UHFFFAOYSA-N 0.000 description 1
- JRMAQQQTXDJDNC-UHFFFAOYSA-M 2-ethoxy-2-oxoacetate Chemical compound CCOC(=O)C([O-])=O JRMAQQQTXDJDNC-UHFFFAOYSA-M 0.000 description 1
- WXBXVVIUZANZAU-UHFFFAOYSA-N 2E-decenoic acid Natural products CCCCCCCC=CC(O)=O WXBXVVIUZANZAU-UHFFFAOYSA-N 0.000 description 1
- GZJLLYHBALOKEX-UHFFFAOYSA-N 6-Ketone, O18-Me-Ussuriedine Natural products CC=CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O GZJLLYHBALOKEX-UHFFFAOYSA-N 0.000 description 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
- 241000588810 Alcaligenes sp. Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 235000019487 Hazelnut oil Nutrition 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000021353 Lignoceric acid Nutrition 0.000 description 1
- CQXMAMUUWHYSIY-UHFFFAOYSA-N Lignoceric acid Natural products CCCCCCCCCCCCCCCCCCCCCCCC(=O)OCCC1=CC=C(O)C=C1 CQXMAMUUWHYSIY-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 241000589540 Pseudomonas fluorescens Species 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 235000019774 Rice Bran oil Nutrition 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 235000019498 Walnut oil Nutrition 0.000 description 1
- 241000179532 [Candida] cylindracea Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 238000006136 alcoholysis reaction Methods 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
- 239000010775 animal oil Substances 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000021324 borage oil Nutrition 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- 235000019219 chocolate Nutrition 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 230000009089 cytolysis Effects 0.000 description 1
- KAUVQQXNCKESLC-UHFFFAOYSA-N docosahexaenoic acid (DHA) Natural products COC(=O)C(C)NOCC1=CC=CC=C1 KAUVQQXNCKESLC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940108623 eicosenoic acid Drugs 0.000 description 1
- BITHHVVYSMSWAG-UHFFFAOYSA-N eicosenoic acid Natural products CCCCCCCCC=CCCCCCCCCCC(O)=O BITHHVVYSMSWAG-UHFFFAOYSA-N 0.000 description 1
- FARYTWBWLZAXNK-WAYWQWQTSA-N ethyl (z)-3-(methylamino)but-2-enoate Chemical compound CCOC(=O)\C=C(\C)NC FARYTWBWLZAXNK-WAYWQWQTSA-N 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 235000013341 fat substitute Nutrition 0.000 description 1
- 239000003778 fat substitute Substances 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010468 hazelnut oil Substances 0.000 description 1
- SZQQHKQCCBDXCG-UHFFFAOYSA-N hexadeca-2,4,6-trienoic acid Chemical compound CCCCCCCCCC=CC=CC=CC(O)=O SZQQHKQCCBDXCG-UHFFFAOYSA-N 0.000 description 1
- 239000010903 husk Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- LKZDFKLGDGSGEO-PABQPRPFSA-N kaempferol 3-O-beta-D-glucosylgalactoside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@H]1[C@H](OC=2C(C3=C(O)C=C(O)C=C3OC=2C=2C=CC(O)=CC=2)=O)O[C@H](CO)[C@H](O)[C@@H]1O LKZDFKLGDGSGEO-PABQPRPFSA-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
- 239000000944 linseed oil Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 150000002886 octanoic acid esters Chemical class 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000000075 primary alcohol group Chemical group 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000008171 pumpkin seed oil Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000008165 rice bran oil Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 239000013076 target substance Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- WXBXVVIUZANZAU-CMDGGOBGSA-N trans-2-decenoic acid Chemical compound CCCCCCC\C=C\C(O)=O WXBXVVIUZANZAU-CMDGGOBGSA-N 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000010497 wheat germ oil Substances 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
-
- 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
-
- 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
- C12P7/6472—Glycerides containing polyunsaturated fatty acid [PUFA] residues, i.e. having two or more double bonds in their backbone
Definitions
- the present invention relates to a method for producing a symmetric triglyceride in which sn (stereo-specific numbering) -positions 1 and 3 are medium-chain fatty acids and sn-position 2 is a long-chain fatty acid.
- sn stereo-specific numbering
- sn-position 2 is a long-chain fatty acid.
- it enables industrially efficient production of high-purity symmetric triglycerides in which the sn-1,3-position is a medium-chain fatty acid and the sn-2 position is a long-chain fatty acid.
- MLM-type triglycerides in which the 1- and 3-positions are medium-chain fatty acids and the sn-2 position is a long-chain fatty acid (hereinafter referred to as MLM-type triglycerides.
- M medium-chain fatty acids
- L long-chain fatty acids
- lipase having no regiospecificity is allowed to act on glycerin and a polyunsaturated fatty acid or a lower alcohol ester thereof to synthesize polyunsaturated fatty acid triglyceride while dehydrating.
- the highly unsaturated fatty acid triglyceride and a fatty acid having 12 or less carbon atoms or a lower alcohol ester thereof are reacted with a lipase which specifically acts on the sn-1,3 position to obtain a target substance.
- the number of carbon atoms of the fatty acid bonded to the sn-1 and sn-3 positions is 12 or less, and 90% by mass or more of the composition of the fatty acid bonded to the sn-2 position is a highly unsaturated fatty acid Manufacturing method of structural fats and oils. '
- MLM-type triglycerides and MLL-type triglycerides are obtained after the reaction.
- these two types of triglycerides are both high-boiling oils and fats and cannot be practically separated.
- a large amount of medium-chain fatty acid ethyl ester must be used in the acidolysis reaction, which lowers productivity and further increases cost. turn into.
- the first reaction is a dehydration reaction
- the enzyme cannot be charged into the ram or the like, and it is difficult to make the continuation.
- the second reaction has a disadvantage that a large excess of a lower alcohol ester must be used in the reaction. Disclosure of the invention
- Another object of the present invention is to reduce the amount of waste generated during production and reduce the amount of MLM Twin-to provide a method for producing triglycerides industrially efficiently and in high purity 0
- the present invention provides the above-mentioned production method, wherein the medium-chain fatty acid triglyceride is taken out (partly or entirely) after the first reaction.
- the present invention provides a method for removing (partially or completely) medium-chain fatty acid triglyceride, medium-chain fatty acid alcohol monoester and long-chain fatty acid alcohol monoester from the reaction product obtained in the second reaction. And / or the medium-chain fatty acid triglyceride taken out after the second reaction is reused as a raw material for the first reaction, and the alcohol monoester of the medium-chain fatty acid taken out after the second reaction is reused as a raw material for the second reaction.
- I will provide a.
- the medium-chain fatty acid triglyceride and the alcohol monoester of long-chain fatty acid are subjected to a random transesterification reaction using an enzyme or a chemical catalyst to obtain a medium-chain fatty acid and A reaction product containing a triglyceride containing a long-chain fatty acid as a constituent fatty acid was obtained, and an alcohol monoester of a medium-chain fatty acid, an alcohol monoester of a long-chain fatty acid, and a medium-chain triglyceride were extracted from the reaction product.
- a triglyceride-containing substance (partly or wholly removed) was obtained.
- the triglyceride-containing substance was transesterified with an alcohol monoester of a medium-chain fatty acid using an sn-1,3-position specific enzyme.
- the alcohol monoester of the medium-chain fatty acid and the alcohol monoester of the long-chain fatty acid are taken out of the reaction product obtained in the second reaction (partially or entirely), and the sn-1,3-positions are in the middle chain.
- a method for producing a symmetric triglyceride which comprises obtaining a symmetric triglyceride in which the fatty acid, sn-2, is a long-chain fatty acid.
- the present invention provides the above production method, wherein the medium-chain fatty acid triglyceride is removed (partly or entirely) after the second reaction.
- the present invention provides the above-mentioned production method, wherein the medium-chain fatty acid triglyceride taken out after the second reaction is reused as a raw material for the first reaction.
- the present invention provides the above-mentioned production method, wherein the alcohol monoester of a long-chain fatty acid taken out after the second reaction is reused as a raw material for the first reaction.
- the present invention provides the above production method, wherein the medium-chain fatty acid triglyceride taken out after the first reaction is reused as a raw material for the first reaction.
- the present invention provides the above-mentioned production method, wherein the alcohol monoester of a long-chain fatty acid taken out after the first reaction is reused as a raw material for the first reaction.
- the present invention relates to a method for producing alcohol
- the present invention provides the above method for recycling ter as a raw material for the second reaction.
- the present invention recycles the alcohol monoester of a long-chain fatty acid and the medium-chain triglyceride taken out after the first reaction and after the Z or the second reaction as raw materials for the first reaction, and after the first reaction and / or It is intended to provide the above-mentioned production method wherein the alcohol monoester of a medium-chain fatty acid taken out after the second reaction is reused as a raw material for the second reaction.
- the present invention provides, in the first reaction, at least one selected from the group consisting of (a) a medium-chain fatty acid triglyceride, (b) a long-chain fatty acid triglyceride, an alcohol monoester of a long-chain fatty acid, and a long-chain fatty acid.
- the seed is subjected to a random transesterification reaction using an enzyme or a chemical catalyst to obtain a reactant containing a first triglyceride containing a medium-chain fatty acid and a long-chain fatty acid as constituent fatty acids.
- Ester exchange of at least one selected from the group consisting of (c) alcohol monoesters of medium-chain fatty acids and medium-chain fatty acids with the first one, liglyceride, using sn-1 and 3-position specific enzymes The present invention provides a method for producing a symmetric triglyceride, which comprises reacting to obtain a symmetric triglyceride in which the sn-1 and 3 positions are medium-chain fatty acids and the sn-2 position is a long-chain fatty acid.
- the present invention provides the above method, wherein the long-chain fatty acid is a long-chain unsaturated fatty acid.
- the present invention provides the method of the present invention, wherein the long-chain unsaturated fatty acid is one or more fatty acids selected from the group consisting of fatty acids having 18 carbon atoms, EPA dicosapentaenoic acid), and DHA (docosahexaenoic acid). Is provided.
- the present invention provides the lipase, wherein the enzyme used in the first reaction and the Z or the second reaction is a powdery lipase having a particle diameter of 90% by mass or more of 1 to 100 ⁇ m. Is provided in the absence of a solvent and in an anhydrous system.
- the present invention relates to a method of enzymatic reaction of the first reaction and / or the second reaction, wherein a powdery lipase is enclosed in a filter together with a filter aid, and a reaction raw material is passed through the filter.
- FIG. 1 is a flow chart schematically showing a method for producing a symmetric (MLM) triglyceride using a medium-chain triglyceride and a long-chain triglyceride of the present invention.
- MLM symmetric triglyceride
- FIG. 2 is a flowchart schematically showing a method for producing a symmetric (MLM type) triglyceride using an alcohol monoester of a medium-chain fatty acid triglyceride and a long-chain fatty acid of the present invention.
- the medium-chain fatty acid may be either a saturated fatty acid or an unsaturated fatty acid. Specific examples include decanoic acid and octanoic acid. '
- Such medium-chain fatty acid triglycerides containing a medium-chain fatty acid as a constituent fatty acid can be easily obtained as a commercial product, and examples of commercially available ones include ODO (manufactured by Seiki Oilio Co., Ltd.). .
- the long-chain fatty acid triglyceride used in the present invention is a component fatty acid having 14 to 28 carbon atoms, preferably 16 to 22 carbon atoms, more preferably 16 to 18 long-chain fatty acids. It is a triglyceride consisting of PT / JP2004 / 009307.
- This long-chain fatty acid triglyceride can be used, for example, to perform a dehydration synthesis reaction of glycerin and one or more kinds of long-chain fatty acids without a catalyst, or to transesterify glycerin with one or more kinds of alcohol esters of long-chain fatty acids. Or by reacting.
- the synthesis can be similarly performed using an enzyme as a catalyst.
- the long-chain fatty acid may be either a saturated fatty acid or an unsaturated fatty acid.
- Examples of long chain fatty acids having 14 to 28 carbon atoms are myristic acid, palmitic acid, stearic acid, arachidic acid, behenic acid, lignoceric acid, serotinic acid, myristoleic acid, quinone decenoic acid, and ⁇ .
- long-chain fatty acids having 16 to 22 carbon atoms are preferred.
- the long-chain fatty acid is preferably a long-chain unsaturated fatty acid in terms of low melting point and operability, and furthermore, in view of versatility and functionality, unsaturated fatty acid having 18 carbon atoms, It is preferably one or more fatty acids selected from 0 HA.
- a commercially available product can be easily obtained, and commercially available soybean oil, rapeseed oil, high-oleic rapeseed oil, sesame oil, corn oil, Cottonseed oil, safflower oil, safflower oil with high oleic acid, sunflower oil, sunflower oil with high oleic acid, cocoa oil, rice bran oil, peanut oil, oleaf oil, perilla oil, perilla oil, linseed oil, pudow seed oil, madou Demiana oil, hazelnut oil, pumpkin seed oil, walnut oil, camellia oil, teaseed oil, borage oil, cottonseed oil, wheat germ oil, algal oil, tallow, lard, chicken oil, fish oil, lard, seal oil, breeding
- oils and fats, and hydrogenated oils and fats thereof which have been made less saturated by the above method, can be used. This Among them,
- the alcohol monoester of a long-chain fatty acid used in the present invention is a long-chain fatty acid having 14 to 28 carbon atoms, preferably 16 to 22 carbon atoms, and more preferably 20 to 22 carbon atoms. It is an ester of an alcohol having 1 to 28, preferably 1 to 4 carbon atoms.
- the alcohol constituting the alcohol monoester of long-chain fatty acid is a monoalcohol having one hydroxyl group.
- the alcohol may be a primary, secondary or tertiary alcohol, and may be a saturated aliphatic alcohol or an unsaturated aliphatic alcohol.
- alcohols constituting alcohol monoesters of long-chain fatty acids include methanol, ethanol, propanol, isopropyl alcohol, and butanol.Although alcohols having 1 to 4 carbon atoms are preferred, particularly safe. In this respect, ethanol is preferred.
- the long-chain fatty acids having 14 to 28 carbon atoms include those described above.
- Alcohol monoesters of long-chain fatty acids can be obtained, for example, by subjecting animal or vegetable oils to an alcoholysis reaction in ethanol using an acid or an alcohol catalyst.
- commercially available products can be easily obtained, and commercially available products such as DHA-90E (docosahexane acid ethyl ester) manufactured by Nippon Kagaku Feed and EPA-90E manufactured by Nippon Kagaku Feed (Ethyl ester of eicosapentaenoic acid).
- the long-chain fatty acids and medium-chain fatty acids used in the present invention include those described in the section of long-chain fatty acid triglycerides and medium-chain fatty acid triglycerides.
- the random transesterification reaction performed in the present invention is performed using an enzyme or a chemical catalyst.
- the fatty acid constituting the reaction raw material is a polyunsaturated fatty acid
- a reaction using a chemical catalyst causes a side reaction, and therefore it is desirable to perform the reaction using an enzyme.
- the enzyme used is preferably a non-specific lipase.
- Non-specific lipases include animals, plants, and microorganisms
- the origin of the deviation may be, for example, a lipase derived from Candida cylindracea, Alcaligenes sp., AlcaHgenes faecalis, or the like.
- the enzyme preferably lipase
- the amount of the enzyme used in the random transesterification reaction is preferably 0.01 to 20% by mass, more preferably 0.1 to 5% by mass, based on the total mass of the reaction raw materials.
- the reaction temperature is preferably from 20 to 100 ° C, more preferably from 40 to 80 ° C, from the viewpoint of durability.
- an alkaline chemical catalyst such as sodium methylate or an acidic chemical catalyst such as sulfuric acid can be used.
- sodium methylates include sodium methylate (manufactured by Nippon Soda Co., Ltd.) and sodium methoxide (Wako Pure Chemical Industries, Ltd.).
- the amount of the chemical catalyst used in the reaction is preferably 0.01 to 5% by mass, more preferably 0.1 to 2% by mass, based on the total mass of the reaction raw materials.
- the reaction time when a chemical catalyst is used is preferably 0.5 to 20 hours, more preferably 2 to 5 hours.
- the triglycerides sn- an ester exchange reaction with specificity for L 3 3-position.
- the sn Examples of 1- and 3-position-specific enzymes include lipase derived from buyu-teng, lipase derived from soybeans, rice husk, castor seed, Aspergillus niger, hizopus delemar, and Rhizopus jabanicas (Hizopus javanicus) s Mucor miehei, Pseudomonas fluorescens and the like.
- the sn-1,3-position specific enzyme preferably lipase
- a powdery one or an immobilized one can be used.
- these enzymes include, for example, lipase PL (manufactured by Meito Sangyo), Lipozym TL (manufactured by Novo), and enzyme powder derived from Ehizomucor miehei.
- powdery enzyme powdery lipase in which 90% or more of the powder particles have a particle diameter of 1 to 100 ⁇ m can be used. The particle size of the enzyme powder particles can be measured by the method described above.
- the amount of the sn-1,3-position specific enzyme is preferably from 0.01 to 10% by mass, more preferably from 0.1 to 5% by mass, based on the total mass of the reaction raw materials.
- the reaction temperature when the sn-1,3-position specific enzyme is used is preferably from 20 to 90 ° C, more preferably from 30 to 60 ° C, from the viewpoint of durability.
- the random transesterification reaction using an enzyme and the transesterification reaction using an sn-1,3-position specific enzyme are preferably performed without a solvent and in an anhydrous system from the viewpoint of workability. Further, from the viewpoint of efficiency, the enzyme reaction is preferably performed by enclosing powdery lipase together with a filter aid in a filter and passing the reaction raw material through the filter. By doing so, there are effects such as separating the reaction product from the remaining enzyme after the reaction.
- the reaction time for random transesterification or sn-1,3-position specific ester exchange in batch mode using enzymes will be described in detail later.
- a random transesterification reaction of a medium-chain fatty acid triglyceride and a long-chain fatty acid triglyceride is performed using an enzyme or a chemical catalyst.
- the reaction time is preferably 1 to 50 hours, more preferably 15 to 25 hours.
- the mixing mass ratio of medium-chain fatty acid triglyceride and long-chain fatty acid triglyceride used as a raw material for the first reaction is not particularly limited, but is preferable when the ratio of long-chain fatty acid triglyceride in the reaction product is suppressed and the reaction efficiency is taken into consideration.
- medium- and long-chain fatty acid triglycerides undergo a random transesterification reaction, with the result that the sn-1,3-position is a medium-chain fatty acid and the sn-2 position is a long-chain fatty acid in addition to the MLM-type triglyceride.
- LML, MLL, LMM, MMM, and LLL triglycerides are obtained.
- the ratio of the medium-chain fatty acid triglyceride to the long-chain fatty acid triglyceride is out of the above range, a large amount of LLL-type triglyceride will be present in the reaction product after the first reaction. Then, in the second reaction to be described later, a large amount of alcohol monoester of a medium-chain fatty acid is required to obtain the target MLM-type triglyceride, which causes a problem that the reaction efficiency is reduced.
- the medium-chain fatty acid triglyceride and the long-chain fatty acid triglyceride are preferably subjected to a random transesterification reaction, and then the medium-chain fatty acid triglyceride (MMM type) is preferably removed (partly or wholly) from the reaction product.
- MMM type medium-chain fatty acid triglyceride
- the content of the medium-chain fatty acid triglyceride in the triglyceride-containing material after the removal treatment is preferably 0 to 10% by mass, more preferably 0 to 6% by mass, and most preferably 0 to 3% by mass. It is good to be.
- MMM type medium-chain fatty acid triglycerides
- a distillation method for example, at 200 ° C and 3 OP.
- the components distilled in a can be divided into those that have a high content of medium-chain triglycerides and those that have a residual content that is high in other triglycerides.
- Examples of the distillation method include a batch method, a continuous method, a thin film method, and a falling film method.
- the medium-chain fatty acid triglyceride extracted by the distillation method can be reused as a reaction raw material in the first reaction, which is efficient.
- the reactant after the first reaction, or the triglyceride-containing medium chain fatty acid triglyceride taken out (partially or completely) from the reaction product is used in the second reaction to prepare the alcohol monoester of the medium chain fatty acid.
- transesterification using sn-1 and 3-position specific enzymes.
- the reaction time is preferably 1 to 50 hours, more preferably 15 to 30 hours.
- the use ratio (mass) of the (first) triglyceride and medium-chain fatty acid alcohol monoester and / or medium-chain fatty acid in the second reaction, in which the medium-chain fatty acid and the long-chain fatty acid are constituent fatty acids is as follows.
- the ratio is preferably 1: 0.5 to 1:20, and more preferably 1: 2 to 1: 7.
- the alcohol monoester of a medium-chain fatty acid and the alcohol monoester of a long-chain fatty acid are taken out, whereby the purity of the MLM-type triglyceride in the finally obtained product can be increased. Further, it is preferable to extract medium-chain fatty acid triglycerides. These substances can be removed by a distillation process such as a batch system.
- Removal of alcohol monoesters of medium-chain fatty acids, alcohol monoesters of long-chain fatty acids, and triglycerides of medium-chain fatty acids from the reaction product obtained in the second reaction was conducted to increase the content of symmetric triglycerides in the final product. It is preferable to carry out the treatment so that the content of each of the above substances in the triglyceride-containing substance obtained after the treatment is reduced.
- medium-chain fatty acids in triglyceride-containing materials obtained after the removal process The alcohol monoester content is preferably from 0 to 5% by mass, more preferably from 0 to 3% by mass, and most preferably from 0 to 1% by mass. Further, the alcohol monoester content of the long-chain fatty acid in the triglyceride-containing substance obtained after the removal treatment is preferably 0 to 5% by mass, more preferably 0 to 3% by mass, and most preferably 0 to 1% by mass.
- the medium-chain fatty acid triglyceride content in the triglyceride-containing product obtained after the removal treatment is preferably 0 to 15% by mass, more preferably 0 to 10% by mass, and most preferably 0 to 8% by mass.
- the components distilled out in the first half of the distillation (50 ° C, 10 OPa) (for medium-chain fatty acids) It should be separated into components with high alcohol monoester content and components distilled in the latter half of distillation (230 ° C, 1 Pa) (content of medium-chain fatty acid triglyceride and long-chain fatty acid with high alcohol monoester content) Can be.
- components with high alcohol monoester content of medium-chain fatty acids In addition, components with high alcohol monoester content of long-chain fatty acids, components with high alcohol monoester content of long-chain fatty acids, and high contents of medium-chain fatty acid triglycerides. It can also be separated into three components. This fractionation can be performed by adjusting the distillation temperature, the degree of decompression, and the distillation time.
- the medium-chain fatty acid triglyceride taken out after the second reaction can be reused as a raw material for the first reaction.
- the alcohol monoester of a medium-chain fatty acid taken out after the second reaction can be reused as a raw material for the second reaction.
- the alcohol monoester of a long-chain fatty acid removed after the second reaction is the first reaction in the method for producing a symmetric triglyceride using a medium-chain fatty acid triglyceride and an alcohol monoester of a long-chain fatty acid according to the present invention described later. It can be used as a raw material.
- the method for producing a symmetric (MLM) triglyceride using the medium-chain fatty acid triglyceride and the long-chain fatty acid triglyceride of the present invention can utilize all the by-products other than the target product, MLM-type triglyceride. , It is efficient.
- a method for producing a symmetric triglyceride of the present invention for producing a MLM type triglyceride using an alcohol monoester of a medium-chain fatty acid triglyceride and a long-chain fatty acid will be described step by step.
- FIG. 2 is a flowchart schematically showing a method for producing the symmetric triglyceride.
- a random transesterification reaction between a medium-chain fatty acid triglyceride and an alcohol monoester of a long-chain fatty acid is performed using an enzyme or a chemical catalyst.
- the alcohol monoester of long-chain fatty acid uses the medium-chain fatty acid triglyceride and long-chain fatty acid triglyceride described above. Alcohol monoesters of long-chain fatty acids, which are by-products of symmetric triglycerides, can also be used.
- the reaction time is preferably 1 to 100 hours, more preferably 15 to 80 hours.
- the mixing mass ratio of the medium-chain fatty acid triglyceride and the alcohol monoester of the long-chain fatty acid used as a raw material for the first reaction is not particularly limited. However, considering the reaction efficiency and the like, the ratio of the long-chain fatty acid triglyceride in the reactant is suppressed. , Preferably 8: 1 to 1: 8, more preferably 2: 1 to 1: 5. The same applies when a long-chain fatty acid is used instead of a long-chain fatty acid alcohol monoester.
- the reactants are MLM type, in which the first and third positions are medium-chain fatty acids and the second position is long-chain fatty acids.
- MLM low-chain fatty acid
- the reactants are MLM type, in which the first and third positions are medium-chain fatty acids and the second position is long-chain fatty acids.
- LML, MLL, LMM, MMM, and LLL triglycerides alcohol monoesters of long-chain fatty acids, and alcohol monoesters of medium-chain fatty acids are obtained.
- the ratio of the medium-chain fatty acid triglyceride to the alcohol monoester of the long-chain fatty acid in the reaction raw material deviates from the above range, a large amount of LLL-type triglyceride may be present in the reaction product after the first reaction. become. Then, in the second reaction to be described later, a large amount of alcohol monoester of a medium-chain fatty acid is required to obtain the target MLM-type triglyceride, which causes a problem that the reaction efficiency is reduced.
- alcohol monoesters of medium-chain fatty acids obtained from the above-mentioned reaction products obtained in the first reaction. Part or all of this is removed by a distillation treatment such as a batch method. At this time, in order to increase the reaction rate in the second reaction, the content of each of the above substances in the triglyceride-containing substance obtained after the removal treatment is reduced. It is preferred to do so.
- the monoester content is preferably from 0 to 5% by mass, more preferably from 0 to 3% by mass, most preferably from 0 to 2% by mass. Further, the content of the alcohol monoester of the long-chain fatty acid in the triglyceride-containing material after the removal treatment is preferably 0 to 5% by mass, more preferably 0 to 3% by mass, and most preferably 0 to 2% by mass. The content of the medium-chain triglyceride in the triglyceride-containing material after the removal treatment is preferably 0 to 15% by mass, more preferably 0 to 10% by mass, and most preferably 0 to 8% by mass.
- the removal of alcohol monoesters of medium-chain fatty acids, alcohol monoesters of long-chain fatty acids and triglycerides of medium-chain fatty acids after the first reaction should be considered in consideration of their reuse as raw materials for reaction. It is preferable to separate and extract components having a high content and components having a high content of alcohol monoesters of long-chain fatty acids and triglyceride of medium-chain fatty acids. This fractionation can be performed by adjusting the temperature, the degree of decompression, and the distillation time of the distillation.
- the components distilled in the first half of the distillation (50 ° C, 10 OPa) (medium chain Fatty alcohol monoester content is high) and components distilled in the latter half of distillation (230 ° C, IPa) (long alcohol fatty acid monoester content and medium fatty acid triglyceride content are high).
- the components distilled in the first half of the distillation (50 ° C, 10 OPa) (medium chain Fatty alcohol monoester content is high) and components distilled in the latter half of distillation (230 ° C, IPa) (long alcohol fatty acid monoester content and medium fatty acid triglyceride content are high).
- a component having a high content of alcohol monoester of a medium-chain fatty acid a component having a high content of alcohol monoester of a long-chain fatty acid, and a component having a high content of triglyceride of a medium-chain fatty acid.
- This fractionation can be performed by adjusting the distillation temperature, the degree of decompression, and the distillation time.
- the components distilled out in the first half of the distillation 25 ° C, 30 Pa (for medium-chain fatty acids)
- the components distilled out in the middle stage of distillation (at 180 ° C, IPa) (those having a high alcohol monoester content of long-chain fatty acids) and the latter half of the distillation (230) ° C ;, 1 P a)
- the components distilling in (a) are those with a high content of medium-chain fatty acid triglycerides.
- the alcohol monoester of a long-chain fatty acid and the triglyceride of a medium-chain fatty acid taken out after the first reaction can be reused as raw materials for the first reaction. Also, the alcohol monoester of a medium-chain fatty acid taken out after the first reaction can be reused as a raw material for the second reaction, which is efficient.
- the medium-chain fatty acid triglyceride, the alcohol monoester of the medium-chain fatty acid, and the alcohol monoester of the long-chain fatty acid were taken out (partly or wholly).
- Transesterification is performed with the alcohol monoester using the sn-1,3-position specific enzyme described above.
- the reaction time is preferably 1 to 100 hours, and more preferably 15 to 80 hours.
- the use ratio (mass) of the (first) triglyceride and the alcohol monoester of the medium-chain fatty acid and / or the medium-chain fatty acid as the constituent fatty acids in the second reaction is defined as 1: It is preferably 0.5 to 1:20, more preferably 1: 2 to 1: 7.
- the alcohol monoester of medium-chain fatty acid and long-chain fatty acid By removing the alcohol monoester, the purity of the MLM triglyceride in the final product can be increased. Furthermore, the purity of the MLM-type triglyceride can be increased by removing the medium-chain triglyceride. The method of extracting these is as described above. It is also possible to obtain a mixture of MLM-type triglyceride and medium-chain fatty acid triglyceride as a final product.
- Alcohol of medium-chain triglycerides and long-chain fatty acids removed after the second reaction Lumonoester can be reused as a raw material for the first reaction.
- the alcohol monoester of a medium-chain fatty acid taken out after the second reaction can be reused as a raw material for the second reaction.
- the method for producing a symmetric (MLM) triglyceride using the medium-chain fatty acid triglyceride and the alcohol monoester of a long-chain fatty acid according to the present invention requires all the by-products other than the target product MLM triglyceride. It can be utilized and is efficient.
- a triglyceride of the present invention for producing an ML M-type triglyceride using a medium-chain fatty acid triglyceride and a long-chain fatty acid
- a triglyceride comprising a medium-chain fatty acid and a long-chain fatty acid as constituent fatty acids
- Components other than triglycerides containing long-chain fatty acids as constituent fatty acids are extracted, and after the second reaction, the target product is a symmetrical trig in which the sn-1,3-positions are medium-chain fatty acids and the sn-2 position is long-chain fatty acids.
- the same components as the first reaction material can be reused as the first reaction material, and the same components as the second reaction material can be reused as the second reaction material. Can be reused. Also, of the components taken out after the second reaction, the same components as the first reaction material can be reused as the first reaction material, and the same components as the second reaction material can be reused as the second reaction material. Can be used.
- the medium-chain fatty acid triglyceride, the long-chain fatty acid, and the medium-chain fatty acid are taken out of the reaction product to obtain a triglyceride-containing substance.
- a second reaction is carried out using the triglyceride-containing substance and the medium-chain fatty acid as raw materials.
- the fatty acid triglyceride, the long-chain fatty acid, and the medium-chain fatty acid are taken out, and a symmetric triglyceride in which the sn-1,3 position is a medium-chain fatty acid and the sn-2 position is a long-chain fatty acid can be obtained.
- the medium-chain fatty acid triglyceride and the long-chain fatty acid taken out after the first reaction and after the second reaction can be reused as the first reaction raw material, and after the first reaction and the second reaction
- the medium-chain fatty acid taken out after completion can be reused as a second reaction raw material.
- unsaturated long chain fatty acid triglycerides, long chain fatty acid monoesters, and long chain fatty acids are used as raw materials from the viewpoint of low melting point and operability.
- symmetric triglycerides containing long-chain saturated fatty acids as constituent fatty acids can be obtained by further performing hydrogenation treatment.
- the symmetric triglyceride containing unsaturated fatty acids obtained by the production of the present invention as constituent fatty acids is further hydrogenated to obtain symmetric triglycerides containing long chain saturated fatty acids as constituent fatty acids. . If manufactured in this way, in the reaction and purification stages, long-chain saturated fatty acid triglycerides, monoesters of long-chain saturated fatty acids, and long-chain saturated fatty acids with high melting points are not used as raw materials. It will be easier.
- s n-1 3 3-position octanoic acid produced by the present invention s n-2-position symmetric triglyceride is Orein acid, by hydrotreating, S 1 ⁇ -
- a symmetric triglyceride comprising a saturated fatty acid having octanoic acid at the 1- and 3-positions and stearic acid at the sn-2 position can be obtained.
- a known method can be used for the hydrogenation treatment.
- DHA ethyl ester refers to docosahexanoic acid ester
- EPA ethyl ester refers to eicosapenic ethyl ester.
- Tricaprylin (trade name: Tricaprylin, Sigma-Aldrich Japan Co., Ltd.) 500 g
- DHA ethyl ester (trade name: DHA-90E, Nippon Dani Gaku Feed Co., Ltd.) 500 g
- non-specific lipase (trade name: Lipase QLM (Meito Sangyo Co., Ltd.) (20 g) was added to a 2000 ml reaction flask, and an enzymatic reaction was carried out at 50 ° C. for 72 hours while stirring with a propeller to obtain 980 g of a reaction product.
- the components (A) to (C) were analyzed by GLC (manufactured by Agilent, 6890 Series GC stem), and the following main components were found.
- ethyl octanoate (trade name: ethyl ethyl octanoate, manufactured by Inoue Koryo Co., Ltd.), and sn-1,3-position specific lipase (trade name: Lipozame TL, manufactured by Novo) 40 g was added to a 500 Oml reaction flask, and an enzymatic reaction was carried out at 50 ° C for 72 hours while stirring with a propeller to obtain 2000 g of a reaction product.
- ethyl octanoate trade name: ethyl ethyl octanoate, manufactured by Inoue Koryo Co., Ltd.
- sn-1,3-position specific lipase (trade name: Lipozame TL, manufactured by Novo) 40 g was added to a 500 Oml reaction flask, and an enzymatic reaction was carried out at 50 ° C for 72 hours while stirring with a propeller to obtain 2000 g of
- the triglyceride-containing substance from which octanoic acid ethyl ester, DH acetyl ester, and tricabrylin were respectively removed was analyzed by GLC and HPLC (manufactured by Shimadzu Corporation, LC-9A LIQUID CHOROMAT 0 GRAPH).
- the content of symmetric triglycerides with -l, position 3 being octanoic acid and sn-2 position being DHA was 93% by mass.
- the triglyceride-containing material from which octanoic acid ethyl ester, DHA ethyl ester, and triglyceride were removed was analyzed by GLC and HPLC, and it was found that sn-l, position 3 were octanoic acid, and sn-2 position.
- Tricaprylin (trade name: Tricaprylin, Sigma-Aldrich Japan Co., Ltd.) 500 g, EPA ethyl ester (trade name: EPA—90E, Nippon Dani Gakuin Feed Co., Ltd.) 500 g ⁇ Lipase QLM (Meito Sangyo 20 g) 200
- the triglyceride-containing substances obtained by removing the octanoic acid ethyl ester, EPA ethyl ester, and tricaprylin, respectively, were analyzed by GLC and HPLC.
- the content of EPA-type symmetric triglycerides was 93% by mass.
- Hyaleak sunflower oil (trade name: Olein-rich, manufactured by Showa Sangyo Co., Ltd.) 700 g and medium-chain fatty acid triglyceride (trade name: ODO, Nisshin Oillio Co., Ltd.) 300 g to lipase QLM (Meito Sangyo Co., Ltd.) 10 g was added to a 2000 ml reaction flask, and an enzymatic reaction was carried out at 50 ° C. for 17 hours while stirring with a propeller, and the remaining enzyme was removed by filtration to obtain 980 g of a reaction product.
- ODO Nisshin Oillio Co., Ltd.
- GLC and HPLC confirmed the triglyceride-containing contents of ethyl octanoate, ethyl decanoate, ethyl oleate, and medium-chain fatty acid triglyceride.
- the content of fatty acid, symmetric triglyceride in which sn-2 position was oleic acid was 95% by mass.
- the composition of the constituent fatty acids was 50% by mass of octanoic acid, 17% by mass of decanoic acid, and 33% by mass of oleic acid.
- the method for producing a symmetric (MLM-type) triglyceride of the present invention can produce a high-purity MLM-type triglyceride.
- by-products other than the target symmetric triglyceride namely, medium-chain fatty acid triglyceride, alcohol monoester of medium-chain fatty acid, and alcohol monoester of long-chain fatty acid can be effectively reused as reaction raw materials. Reduces waste and is industrially efficient, high-purity M
- LM type triglyceride can be manufactured.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Zoology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN200480019349.4A CN1816614B (zh) | 2003-07-09 | 2004-06-24 | 生产对称的甘油三酯的方法 |
EP04746776A EP1642959B1 (en) | 2003-07-09 | 2004-06-24 | Process for producing symmetrical triglyceride |
DE602004027250T DE602004027250D1 (de) | 2003-07-09 | 2004-06-24 | Verfahren zur herstellung von symmetrischem triglycerid |
AT04746776T ATE468384T1 (de) | 2003-07-09 | 2004-06-24 | Verfahren zur herstellung von symmetrischem triglycerid |
CA2530123A CA2530123C (en) | 2003-07-09 | 2004-06-24 | Method for producing symmetric triglycerides |
JP2005511502A JP4290162B2 (ja) | 2003-07-09 | 2004-06-24 | 対称型トリグリセリドの製造方法 |
US11/326,436 US7442531B2 (en) | 2003-07-09 | 2006-01-06 | Method for producing symmetric triglycerides |
NO20060633A NO20060633L (no) | 2003-07-09 | 2006-02-09 | Fremgangsmate for produksjon av symmetriske triglycerider |
HK06113725.9A HK1092834A1 (en) | 2003-07-09 | 2006-12-14 | Process for producing symmetrical triglyceride |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2003-194322 | 2003-07-09 | ||
JP2003194322 | 2003-07-09 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/326,436 Continuation US7442531B2 (en) | 2003-07-09 | 2006-01-06 | Method for producing symmetric triglycerides |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2005005586A1 true WO2005005586A1 (ja) | 2005-01-20 |
Family
ID=34055660
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2004/009307 WO2005005586A1 (ja) | 2003-07-09 | 2004-06-24 | 対称型トリグリセリドの製造方法 |
Country Status (13)
Country | Link |
---|---|
US (1) | US7442531B2 (ja) |
EP (1) | EP1642959B1 (ja) |
JP (1) | JP4290162B2 (ja) |
KR (1) | KR101011161B1 (ja) |
CN (1) | CN1816614B (ja) |
AT (1) | ATE468384T1 (ja) |
CA (1) | CA2530123C (ja) |
DE (1) | DE602004027250D1 (ja) |
HK (1) | HK1092834A1 (ja) |
MY (1) | MY143864A (ja) |
NO (1) | NO20060633L (ja) |
TW (1) | TWI318237B (ja) |
WO (1) | WO2005005586A1 (ja) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006121182A1 (ja) | 2005-05-13 | 2006-11-16 | The Nisshin Oillio Group, Ltd. | 脂肪酸トリグリセリドの分子間化合物 |
WO2008010543A1 (fr) * | 2006-07-19 | 2008-01-24 | The Nisshin Oillio Group, Ltd. | Procédé destiné à produire un beurre solide adapté à un produit de chocolaterie |
WO2016013582A1 (ja) * | 2014-07-22 | 2016-01-28 | 日清オイリオグループ株式会社 | 粉末油脂組成物、粉末油脂組成物を含む食品及びこれらの製造方法 |
JP2017127255A (ja) * | 2016-01-21 | 2017-07-27 | 日清オイリオグループ株式会社 | 調味料用粉末油脂組成物 |
JP2018531043A (ja) * | 2015-09-28 | 2018-10-25 | コービオン バイオテック, インコーポレイテッド | 不斉トリグリセリド分子を有するトリグリセリド油 |
JP2020023700A (ja) * | 2013-12-18 | 2020-02-13 | コモンウェルス サイエンティフィック アンド インダストリアル リサーチ オーガナイゼーション | 長鎖多価不飽和脂肪酸を含む脂質 |
US11147285B2 (en) | 2015-09-24 | 2021-10-19 | The Nisshin Oillio Group, Ltd. | Powdery fat or oil composition and method for producing same |
US11219224B2 (en) | 2016-01-21 | 2022-01-11 | The Nisshin Oillio Group, Ltd. | Thickener for liquid component |
US11220654B2 (en) | 2016-01-21 | 2022-01-11 | The Nisshin Oillio Group, Ltd. | Powderizing agent for liquid component |
US11241020B2 (en) | 2016-01-21 | 2022-02-08 | The Nisshin Oillio Group, Ltd. | Powderizing agent for liquid component |
US11246322B2 (en) | 2016-01-21 | 2022-02-15 | The Nisshin Oillio Group, Ltd. | Thickener for liquid component |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102004019472A1 (de) * | 2004-04-22 | 2005-11-17 | Bayer Healthcare Ag | Phenylacetamide |
MY148943A (en) * | 2006-08-28 | 2013-06-14 | Univ Putra Malaysia | Production of acylglycerol esters |
KR100684642B1 (ko) * | 2006-09-14 | 2007-02-22 | 주식회사 일신웰스 | 어유 유래 글리세라이드 유지 조성물 및 이의 제조방법 |
UA97127C2 (uk) * | 2006-12-06 | 2012-01-10 | Бандж Ойлз, Инк. | Спосіб безперервної ферментативної обробки композиції, що містить ліпід, та система для його здійснення |
SG10201509864QA (en) | 2007-06-01 | 2015-12-30 | Solazyme Inc | Production of oil in microorganisms |
CN101485364B (zh) * | 2009-02-11 | 2013-05-01 | 罗盖特生物营养品(武汉)有限公司 | 酶法酯交换生产含二十二碳六烯酸的食用油脂的方法 |
AU2011257982B2 (en) | 2010-05-28 | 2017-05-25 | Corbion Biotech, Inc. | Tailored oils produced from recombinant heterotrophic microorganisms |
CN101979625B (zh) * | 2010-11-03 | 2013-07-17 | 江南大学 | 一种酶法催化酯交换合成中/长链结构甘油三酯的方法 |
SG10201509035WA (en) | 2010-11-03 | 2015-12-30 | Solazyme Inc | Microbial Oils With Lowered Pour Points, Dielectric Fluids Produced Therefrom, And Related Methods |
KR101964965B1 (ko) | 2011-02-02 | 2019-04-03 | 테라비아 홀딩스 인코포레이티드 | 재조합 유지성 미생물로부터 생산된 맞춤 오일 |
BR112014025719A8 (pt) | 2012-04-18 | 2017-10-03 | Solazyme Inc | Óleos customizados |
MX369685B (es) | 2013-10-04 | 2019-11-19 | Terravia Holdings Inc | Aceites adaptables. |
CN104543045A (zh) * | 2013-10-12 | 2015-04-29 | 中粮营养健康研究院有限公司 | 一种油脂组合物、其制备方法及其用途 |
US11718577B2 (en) | 2013-12-18 | 2023-08-08 | Commonwealth Scientific And Industrial Research Organisation | Lipid compositions comprising triacylglycerol with long-chain polyunsaturated fatty acids |
CN103897811A (zh) * | 2014-04-02 | 2014-07-02 | 河北康睿达脂质有限公司 | 一种中长链脂肪酸油脂的生产方法 |
EP3620517A3 (en) | 2014-07-10 | 2020-07-29 | Corbion Biotech, Inc. | Ketoacyl acp synthase genes and uses thereof |
CN105638927B (zh) * | 2014-11-13 | 2020-11-10 | 丰益(上海)生物技术研发中心有限公司 | 油脂组合物以及油脂组合物的制备方法 |
CN107549332A (zh) * | 2017-09-11 | 2018-01-09 | 江南大学 | 增强婴儿长链多不饱和脂肪酸生物利用率的方法及其产品 |
CN111893143B (zh) * | 2020-07-23 | 2021-10-26 | 广州福汇食品科技有限公司 | 一种可定制sn-2位脂肪酸的油脂的制备方法及其应用 |
CN116458645A (zh) * | 2023-04-20 | 2023-07-21 | 重庆第二师范学院 | Sn-2长链多不饱和脂肪酸结构脂及其制备方法和应用 |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5571797A (en) | 1978-11-21 | 1980-05-30 | Fuji Oil Co Ltd | Manufacture of cacao butter substitute fat |
US4364868A (en) * | 1980-02-07 | 1982-12-21 | Lever Brothers Company | Cocoabutter replacement fat compositions |
GB2170506B (en) * | 1984-12-17 | 1989-08-23 | Unilever Plc | Edible fats |
JP2749034B2 (ja) * | 1986-03-04 | 1998-05-13 | 名糖産業株式会社 | 高分子量リパーゼによる対称型トリグリセリドの製造法 |
JPH0783718B2 (ja) | 1986-05-21 | 1995-09-13 | 日清製油株式会社 | 1,3−ジステアロ−2−オレインの製造法 |
JPH0789944B2 (ja) * | 1986-12-23 | 1995-10-04 | 旭電化工業株式会社 | 製菓用油脂組成物の製法 |
GB8925352D0 (en) * | 1989-11-09 | 1989-12-28 | Unilever Plc | Fats |
US5149642A (en) * | 1990-04-20 | 1992-09-22 | The Procter & Gamble Company | Process for preparing 2-acylglycerides or 1,2 or 2,3-diacylglycerides |
EP0519561A1 (en) | 1991-06-18 | 1992-12-23 | Unilever N.V. | Enzymic triglyceride conversion |
US5304427A (en) * | 1992-07-02 | 1994-04-19 | General Electric Company | Composite structure with NBTIA1CRHF alloy matrix and niobium base metal reinforcement |
US6369252B1 (en) | 1998-02-26 | 2002-04-09 | The University Of Georgia Research Foundation, Inc. | Structured lipids |
JPH11243982A (ja) | 1998-03-03 | 1999-09-14 | Asahi Denka Kogyo Kk | エステル交換油脂の製造方法 |
JP2000270885A (ja) | 1999-03-26 | 2000-10-03 | Nippon Suisan Kaisha Ltd | 高度不飽和脂肪酸を含有する構造油脂の製造方法 |
US6737100B1 (en) * | 1999-03-30 | 2004-05-18 | Fuji Oil Company, Limited | Foamed chocolate and process for producing the same |
-
2004
- 2004-06-24 CN CN200480019349.4A patent/CN1816614B/zh not_active Expired - Lifetime
- 2004-06-24 JP JP2005511502A patent/JP4290162B2/ja not_active Expired - Lifetime
- 2004-06-24 AT AT04746776T patent/ATE468384T1/de not_active IP Right Cessation
- 2004-06-24 KR KR1020067000356A patent/KR101011161B1/ko not_active IP Right Cessation
- 2004-06-24 DE DE602004027250T patent/DE602004027250D1/de not_active Expired - Lifetime
- 2004-06-24 WO PCT/JP2004/009307 patent/WO2005005586A1/ja active Application Filing
- 2004-06-24 CA CA2530123A patent/CA2530123C/en not_active Expired - Fee Related
- 2004-06-24 EP EP04746776A patent/EP1642959B1/en not_active Expired - Lifetime
- 2004-06-28 MY MYPI20042550A patent/MY143864A/en unknown
- 2004-06-30 TW TW093119863A patent/TWI318237B/zh active
-
2006
- 2006-01-06 US US11/326,436 patent/US7442531B2/en active Active
- 2006-02-09 NO NO20060633A patent/NO20060633L/no not_active Application Discontinuation
- 2006-12-14 HK HK06113725.9A patent/HK1092834A1/xx not_active IP Right Cessation
Non-Patent Citations (3)
Title |
---|
IRIMESCU R. ET AL: "Enzymatic synthesis of 1,3-dicapryloyl-2-eicosaentaenoylglycerol", J. AM. OIL CHEM. SOC., vol. 77, no. 5, 2000, pages 501 - 506, XP002946597 * |
IWASAKI Y. ET AL: "Enzymatic synthesis of structured lipids", J. OF MOLECULAR CATALYSIS B: ENZYMATIC, vol. 10, no. 1-3, 2000, pages 129 - 140, XP002977744 * |
XU X. ET AL: "Pilot batch production of specific-structured lipids by lipase-catalyzed interesterification: preliminary study on incorporation and acyl migration", J. AM. OIL CHEM. SOC., vol. 72, no. 2, 1998, pages 301 - 308, XP002977743 * |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7648724B2 (en) | 2005-05-13 | 2010-01-19 | The Nisshin Oillio Group, Ltd. | Intermolecular compounds of fatty acid triglycerides |
WO2006121182A1 (ja) | 2005-05-13 | 2006-11-16 | The Nisshin Oillio Group, Ltd. | 脂肪酸トリグリセリドの分子間化合物 |
WO2008010543A1 (fr) * | 2006-07-19 | 2008-01-24 | The Nisshin Oillio Group, Ltd. | Procédé destiné à produire un beurre solide adapté à un produit de chocolaterie |
JPWO2008010543A1 (ja) * | 2006-07-19 | 2009-12-17 | 日清オイリオグループ株式会社 | チョコレート製品に適するハードバターの製造方法 |
RU2445351C2 (ru) * | 2006-07-19 | 2012-03-20 | Дзе Ниссин Ойллио Груп, Лтд. | Способ получения твердого масла, подходящего для шоколадных продуктов |
JP2020023700A (ja) * | 2013-12-18 | 2020-02-13 | コモンウェルス サイエンティフィック アンド インダストリアル リサーチ オーガナイゼーション | 長鎖多価不飽和脂肪酸を含む脂質 |
WO2016013582A1 (ja) * | 2014-07-22 | 2016-01-28 | 日清オイリオグループ株式会社 | 粉末油脂組成物、粉末油脂組成物を含む食品及びこれらの製造方法 |
JP5937771B1 (ja) * | 2014-07-22 | 2016-06-22 | 日清オイリオグループ株式会社 | 粉末油脂組成物、粉末油脂組成物を含む食品及びこれらの製造方法 |
US11292989B2 (en) | 2014-07-22 | 2022-04-05 | The Nisshin Oillio Group, Ltd. | Powdered fat/oil composition, food including powdered fat/oil composition, and methods for producing same |
US11147285B2 (en) | 2015-09-24 | 2021-10-19 | The Nisshin Oillio Group, Ltd. | Powdery fat or oil composition and method for producing same |
JP2018531043A (ja) * | 2015-09-28 | 2018-10-25 | コービオン バイオテック, インコーポレイテッド | 不斉トリグリセリド分子を有するトリグリセリド油 |
US11219224B2 (en) | 2016-01-21 | 2022-01-11 | The Nisshin Oillio Group, Ltd. | Thickener for liquid component |
US11220654B2 (en) | 2016-01-21 | 2022-01-11 | The Nisshin Oillio Group, Ltd. | Powderizing agent for liquid component |
US11241020B2 (en) | 2016-01-21 | 2022-02-08 | The Nisshin Oillio Group, Ltd. | Powderizing agent for liquid component |
US11246322B2 (en) | 2016-01-21 | 2022-02-15 | The Nisshin Oillio Group, Ltd. | Thickener for liquid component |
JP2017127255A (ja) * | 2016-01-21 | 2017-07-27 | 日清オイリオグループ株式会社 | 調味料用粉末油脂組成物 |
Also Published As
Publication number | Publication date |
---|---|
JP4290162B2 (ja) | 2009-07-01 |
DE602004027250D1 (de) | 2010-07-01 |
TW200504200A (en) | 2005-02-01 |
EP1642959B1 (en) | 2010-05-19 |
EP1642959A1 (en) | 2006-04-05 |
JPWO2005005586A1 (ja) | 2006-08-24 |
US7442531B2 (en) | 2008-10-28 |
CN1816614A (zh) | 2006-08-09 |
KR20060027403A (ko) | 2006-03-27 |
CA2530123A1 (en) | 2005-01-20 |
EP1642959A4 (en) | 2007-04-18 |
ATE468384T1 (de) | 2010-06-15 |
US20060115882A1 (en) | 2006-06-01 |
NO20060633L (no) | 2006-04-07 |
KR101011161B1 (ko) | 2011-01-26 |
CN1816614B (zh) | 2010-04-21 |
MY143864A (en) | 2011-07-15 |
CA2530123C (en) | 2012-05-01 |
TWI318237B (en) | 2009-12-11 |
HK1092834A1 (en) | 2007-02-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
WO2005005586A1 (ja) | 対称型トリグリセリドの製造方法 | |
US11781161B2 (en) | Enzymatic enrichment of n-3 fatty acids in the form of glycerides | |
EP1300470B1 (en) | Process for the prodcution of glycerides with lipases | |
US9476008B2 (en) | Process for separating polyunsaturated fatty acids from long chain unsaturated or less saturated fatty acids | |
US10119098B2 (en) | Concentration of fatty acid alkyl esters by enzymatic reactions with glycerol | |
JPWO2019167331A1 (ja) | 2位がパルミチン酸に富む油脂組成物の製造方法 | |
EP1749099B1 (en) | Process for enzymatic production of triglycerides | |
Piazza et al. | Lipase-catalyzed harvesting and/or enrichment of industrially and nutritionally important fatty acids | |
Shimada et al. | Application of multistep reactions with lipases to the oil and fat industry |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
WWE | Wipo information: entry into national phase |
Ref document number: 200480019349.4 Country of ref document: CN |
|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2530123 Country of ref document: CA |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2005511502 Country of ref document: JP Ref document number: 11326436 Country of ref document: US Ref document number: 1020067000356 Country of ref document: KR |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2004746776 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 2004746776 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 11326436 Country of ref document: US |