JPS63112993A - Production of saccharide or sugarlcohol fatty acid ester by enzymatic method - Google Patents
Production of saccharide or sugarlcohol fatty acid ester by enzymatic methodInfo
- Publication number
- JPS63112993A JPS63112993A JP25801486A JP25801486A JPS63112993A JP S63112993 A JPS63112993 A JP S63112993A JP 25801486 A JP25801486 A JP 25801486A JP 25801486 A JP25801486 A JP 25801486A JP S63112993 A JPS63112993 A JP S63112993A
- Authority
- JP
- Japan
- Prior art keywords
- acid
- fatty acid
- saccharide
- acetylated
- lipase
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 24
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 24
- 239000000194 fatty acid Substances 0.000 title claims abstract description 24
- -1 fatty acid ester Chemical class 0.000 title claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- 150000001720 carbohydrates Chemical class 0.000 title abstract 4
- 238000006911 enzymatic reaction Methods 0.000 title description 2
- 102000004882 Lipase Human genes 0.000 claims abstract description 15
- 108090001060 Lipase Proteins 0.000 claims abstract description 15
- 239000004367 Lipase Substances 0.000 claims abstract description 15
- 235000019421 lipase Nutrition 0.000 claims abstract description 15
- 150000005846 sugar alcohols Chemical class 0.000 claims abstract description 15
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 13
- 239000003960 organic solvent Substances 0.000 claims abstract description 12
- 235000000346 sugar Nutrition 0.000 claims description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000758 substrate Substances 0.000 abstract description 6
- 108090000790 Enzymes Proteins 0.000 abstract description 5
- 102000004190 Enzymes Human genes 0.000 abstract description 5
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 abstract description 4
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 abstract description 4
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract description 3
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 abstract description 3
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 3
- 239000008103 glucose Substances 0.000 abstract description 3
- 238000010438 heat treatment Methods 0.000 abstract description 3
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 abstract description 3
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 abstract description 2
- HEBKCHPVOIAQTA-QWWZWVQMSA-N D-arabinitol Chemical compound OC[C@@H](O)C(O)[C@H](O)CO HEBKCHPVOIAQTA-QWWZWVQMSA-N 0.000 abstract description 2
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 abstract description 2
- 229930091371 Fructose Natural products 0.000 abstract description 2
- 239000005715 Fructose Substances 0.000 abstract description 2
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 abstract description 2
- 239000005639 Lauric acid Substances 0.000 abstract description 2
- 229930195725 Mannitol Natural products 0.000 abstract description 2
- PYMYPHUHKUWMLA-LMVFSUKVSA-N Ribose Natural products OC[C@@H](O)[C@@H](O)[C@@H](O)C=O PYMYPHUHKUWMLA-LMVFSUKVSA-N 0.000 abstract description 2
- HMFHBZSHGGEWLO-UHFFFAOYSA-N alpha-D-Furanose-Ribose Natural products OCC1OC(O)C(O)C1O HMFHBZSHGGEWLO-UHFFFAOYSA-N 0.000 abstract description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 abstract description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 abstract description 2
- 230000006196 deacetylation Effects 0.000 abstract description 2
- 238000003381 deacetylation reaction Methods 0.000 abstract description 2
- 239000000594 mannitol Substances 0.000 abstract description 2
- 235000010355 mannitol Nutrition 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 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 abstract 1
- 235000020661 alpha-linolenic acid Nutrition 0.000 abstract 1
- 229960004488 linolenic acid Drugs 0.000 abstract 1
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 150000008163 sugars Chemical class 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 229930006000 Sucrose Natural products 0.000 description 4
- 229940088598 enzyme Drugs 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000008117 stearic acid Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000000397 acetylating effect Effects 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
- KHAVLLBUVKBTBG-UHFFFAOYSA-N dec-9-enoic acid Chemical compound OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- UKMSUNONTOPOIO-UHFFFAOYSA-N docosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCCCC(O)=O UKMSUNONTOPOIO-UHFFFAOYSA-N 0.000 description 2
- KEMQGTRYUADPNZ-UHFFFAOYSA-N heptadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(O)=O KEMQGTRYUADPNZ-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- FYGDTMLNYKFZSV-UHFFFAOYSA-N mannotriose Natural products OC1C(O)C(O)C(CO)OC1OC1C(CO)OC(OC2C(OC(O)C(O)C2O)CO)C(O)C1O FYGDTMLNYKFZSV-UHFFFAOYSA-N 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 2
- 239000012454 non-polar solvent Substances 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- SECPZKHBENQXJG-FPLPWBNLSA-N palmitoleic acid Chemical compound CCCCCC\C=C/CCCCCCCC(O)=O SECPZKHBENQXJG-FPLPWBNLSA-N 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 238000005809 transesterification reaction Methods 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- 150000004043 trisaccharides Chemical class 0.000 description 2
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- WBBQTNCISCKUMU-PDBXOOCHSA-N (13Z,16Z,19Z)-docosatrienoic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCCCCC(O)=O WBBQTNCISCKUMU-PDBXOOCHSA-N 0.000 description 1
- YKHVVNDSWHSBPA-BLHCBFLLSA-N (2E,4E)-deca-2,4-dienoic acid Chemical compound CCCCC\C=C\C=C\C(O)=O YKHVVNDSWHSBPA-BLHCBFLLSA-N 0.000 description 1
- BJNARTXTPVWSGJ-SRGMUBKESA-N (2E,4E,6E,8E)-hexadeca-2,4,6,8-tetraenoic acid Chemical compound CCCCCCC\C=C\C=C\C=C\C=C\C(O)=O BJNARTXTPVWSGJ-SRGMUBKESA-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
- UYQJCPNSAVWAFU-ZEUIETHYSA-N (2r,3r,4r,5r)-4-[(2s,3r,4r,5s,6r)-5-[(2s,3r,4r,5s,6r)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2,3,5,6-tetrahydroxyhexanal Chemical compound O[C@@H]1[C@@H](O)[C@H](O[C@H]([C@H](O)CO)[C@H](O)[C@@H](O)C=O)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@@H](CO)O1 UYQJCPNSAVWAFU-ZEUIETHYSA-N 0.000 description 1
- FPRKGXIOSIUDSE-SYACGTDESA-N (2z,4z,6z,8z)-docosa-2,4,6,8-tetraenoic acid Chemical compound CCCCCCCCCCCCC\C=C/C=C\C=C/C=C\C(O)=O FPRKGXIOSIUDSE-SYACGTDESA-N 0.000 description 1
- HXBYBCASAVUYKF-GVYWOMJSSA-N (4r,5s,6r,7r)-4,5,6,7,8-pentahydroxyoctane-2,3-dione Chemical compound CC(=O)C(=O)[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO HXBYBCASAVUYKF-GVYWOMJSSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N 12-hydroxylauric acid Chemical compound OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 1
- TWJNQYPJQDRXPH-UHFFFAOYSA-N 2-cyanobenzohydrazide Chemical compound NNC(=O)C1=CC=CC=C1C#N TWJNQYPJQDRXPH-UHFFFAOYSA-N 0.000 description 1
- DBTMGCOVALSLOR-UHFFFAOYSA-N 32-alpha-galactosyl-3-alpha-galactosyl-galactose Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(OC2C(C(CO)OC(O)C2O)O)OC(CO)C1O DBTMGCOVALSLOR-UHFFFAOYSA-N 0.000 description 1
- PVXPPJIGRGXGCY-DJHAAKORSA-N 6-O-alpha-D-glucopyranosyl-alpha-D-fructofuranose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@](O)(CO)O1 PVXPPJIGRGXGCY-DJHAAKORSA-N 0.000 description 1
- YWWVWXASSLXJHU-UHFFFAOYSA-N 9E-tetradecenoic acid Natural products CCCCC=CCCCCCCCC(O)=O YWWVWXASSLXJHU-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 235000021357 Behenic acid Nutrition 0.000 description 1
- DPUOLQHDNGRHBS-UHFFFAOYSA-N Brassidinsaeure Natural products CCCCCCCCC=CCCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-UHFFFAOYSA-N 0.000 description 1
- 101100112111 Caenorhabditis elegans cand-1 gene Proteins 0.000 description 1
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 1
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
- RXVWSYJTUUKTEA-UHFFFAOYSA-N D-maltotriose Natural products OC1C(O)C(OC(C(O)CO)C(O)C(O)C=O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 RXVWSYJTUUKTEA-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 1
- 235000021292 Docosatetraenoic acid Nutrition 0.000 description 1
- URXZXNYJPAJJOQ-UHFFFAOYSA-N Erucic acid Natural products CCCCCCC=CCCCCCCCCCCCC(O)=O URXZXNYJPAJJOQ-UHFFFAOYSA-N 0.000 description 1
- OPGOLNDOMSBSCW-CLNHMMGSSA-N Fursultiamine hydrochloride Chemical compound Cl.C1CCOC1CSSC(\CCO)=C(/C)N(C=O)CC1=CN=C(C)N=C1N OPGOLNDOMSBSCW-CLNHMMGSSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- 235000021360 Myristic acid Nutrition 0.000 description 1
- TUNFSRHWOTWDNC-UHFFFAOYSA-N Myristic acid Natural products CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 235000021319 Palmitoleic acid Nutrition 0.000 description 1
- 108010019160 Pancreatin Proteins 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 101000968491 Pseudomonas sp. (strain 109) Triacylglycerol lipase Proteins 0.000 description 1
- MUPFEKGTMRGPLJ-RMMQSMQOSA-N Raffinose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 MUPFEKGTMRGPLJ-RMMQSMQOSA-N 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- UQZIYBXSHAGNOE-USOSMYMVSA-N Stachyose Natural products O(C[C@H]1[C@@H](O)[C@H](O)[C@H](O)[C@@H](O[C@@]2(CO)[C@H](O)[C@@H](O)[C@@H](CO)O2)O1)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](CO[C@@H]2[C@@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O2)O1 UQZIYBXSHAGNOE-USOSMYMVSA-N 0.000 description 1
- ZIJKGAXBCRWEOL-SAXBRCJISA-N Sucrose octaacetate Chemical compound CC(=O)O[C@H]1[C@H](OC(C)=O)[C@@H](COC(=O)C)O[C@@]1(COC(C)=O)O[C@@H]1[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](COC(C)=O)O1 ZIJKGAXBCRWEOL-SAXBRCJISA-N 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-UHFFFAOYSA-N UNPD196149 Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC2C(C(O)C(O)C(CO)O2)O)O1 MUPFEKGTMRGPLJ-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- UAOKXEHOENRFMP-ZJIFWQFVSA-N [(2r,3r,4s,5r)-2,3,4,5-tetraacetyloxy-6-oxohexyl] acetate Chemical compound CC(=O)OC[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](OC(C)=O)C=O UAOKXEHOENRFMP-ZJIFWQFVSA-N 0.000 description 1
- 241000179532 [Candida] cylindracea Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- LHAOFBCHXGZGOR-NAVBLJQLSA-N alpha-D-Manp-(1->3)-alpha-D-Manp-(1->2)-alpha-D-Manp Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@@H](O[C@@H]2[C@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](O)[C@@H](CO)O1 LHAOFBCHXGZGOR-NAVBLJQLSA-N 0.000 description 1
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- FYGDTMLNYKFZSV-ZWSAEMDYSA-N cellotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@@H](O[C@@H]2[C@H](OC(O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-ZWSAEMDYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- FBPFZTCFMRRESA-GUCUJZIJSA-N galactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-GUCUJZIJSA-N 0.000 description 1
- 229930182830 galactose Natural products 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- YAQXGBBDJYBXKL-UHFFFAOYSA-N iron(2+);1,10-phenanthroline;dicyanide Chemical compound [Fe+2].N#[C-].N#[C-].C1=CN=C2C3=NC=CC=C3C=CC2=C1.C1=CN=C2C3=NC=CC=C3C=CC2=C1 YAQXGBBDJYBXKL-UHFFFAOYSA-N 0.000 description 1
- XDQQQSFYCSYSCP-UHFFFAOYSA-N kaempferol 3-O-beta-D-glucopyranosyl(1-3)-alpha-L-rhamnopyranosyl(1-6)-beta-D-glucopyranoside Natural products CC=CCCC=CCCC(O)=O XDQQQSFYCSYSCP-UHFFFAOYSA-N 0.000 description 1
- 239000000832 lactitol Substances 0.000 description 1
- 235000010448 lactitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-JVCRWLNRSA-N lactitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-JVCRWLNRSA-N 0.000 description 1
- 229960003451 lactitol Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 235000020778 linoleic acid Nutrition 0.000 description 1
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 description 1
- 239000000845 maltitol Substances 0.000 description 1
- 235000010449 maltitol Nutrition 0.000 description 1
- VQHSOMBJVWLPSR-WUJBLJFYSA-N maltitol Chemical compound OC[C@H](O)[C@@H](O)[C@@H]([C@H](O)CO)O[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O VQHSOMBJVWLPSR-WUJBLJFYSA-N 0.000 description 1
- 229940035436 maltitol Drugs 0.000 description 1
- 150000002772 monosaccharides Chemical class 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- 229940055695 pancreatin Drugs 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- MUPFEKGTMRGPLJ-ZQSKZDJDSA-N raffinose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)O1 MUPFEKGTMRGPLJ-ZQSKZDJDSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 1
- 229960003656 ricinoleic acid Drugs 0.000 description 1
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- UQZIYBXSHAGNOE-XNSRJBNMSA-N stachyose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO[C@@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO[C@@H]3[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O3)O)O2)O)O1 UQZIYBXSHAGNOE-XNSRJBNMSA-N 0.000 description 1
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004044 tetrasaccharides Chemical class 0.000 description 1
- 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 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
Description
【発明の詳細な説明】
本光凱立昆旦
本発明は、リパーゼを使用するエステル交換反応による
糖もしくは糖アルコールの脂肪酸エステルの製法に関す
る。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a method for producing fatty acid esters of sugars or sugar alcohols by transesterification using lipase.
糖類および糖アルコールの高級脂肪酸エステルは、脂肪
酸エステルと糖または糖アルコールとのエステル交換反
応によって化学的に合成し得ることは公知であり、特に
ショ糖脂肪酸エステルはこの方法によって大金に生産さ
れている。これら化学的合成法はいずれも加熱工程を含
むため、加熱により生成物が着色したり、複雑な混合物
となるなどの欠点がある。It is known that higher fatty acid esters of sugars and sugar alcohols can be chemically synthesized by transesterification of fatty acid esters with sugars or sugar alcohols, and sucrose fatty acid esters in particular have been produced with great success by this method. There is. Since all of these chemical synthesis methods involve a heating step, they have drawbacks such as coloring of the product due to heating and the formation of complex mixtures.
これらの欠点を避けるため、最近遊離脂肪酸と糖または
糖アルコールとを基質とし、リパーゼの存在下インキュ
ベートすることによる脂肪酸エステルの生化学的合成法
が提案され、本出願人らにより特許出願中である。In order to avoid these drawbacks, a biochemical synthesis method for fatty acid esters using free fatty acids and sugars or sugar alcohols as substrates and incubation in the presence of lipase has recently been proposed, and a patent application is currently being filed by the present applicants. .
本発明は、酵素法による糖もしくは糖アルコールの脂肪
酸エステルの合成を有機溶媒中で実施し得る方法を、提
案する。The present invention proposes a method in which fatty acid esters of sugars or sugar alcohols can be synthesized by enzymatic methods in organic solvents.
本光皿二皿丞
本発明は、アセチル化した糖もしくは糖アルコールと、
脂肪酸とを有機溶媒に溶解し、これにリパーゼを加えて
インキュベートすることを特徴とする糖もしくは糖アル
コール脂肪酸エステルの製法を提供する。The present invention provides an acetylated sugar or sugar alcohol,
The present invention provides a method for producing a sugar or sugar alcohol fatty acid ester, which comprises dissolving a fatty acid in an organic solvent, adding lipase to the solution, and incubating the solution.
糖および糖アルコールは複数の水酸基を有するため親水
性であるが、アセチル化することにより親油性となり、
有機溶媒に可溶になる。脂肪酸は元来疎水性であるので
水に熔けないが有機溶媒には可溶である。従って本発明
の反応は均一系で行われ、基質濃度を高くすることがで
きる。また水性溶媒中の反応では使用できなかった常温
で固体の脂肪酸も本発明では使用することができる。Sugars and sugar alcohols are hydrophilic because they have multiple hydroxyl groups, but they become lipophilic when acetylated.
Becomes soluble in organic solvents. Fatty acids are hydrophobic in nature and cannot be dissolved in water, but are soluble in organic solvents. Therefore, the reaction of the present invention is carried out in a homogeneous system, and the substrate concentration can be increased. Furthermore, fatty acids that are solid at room temperature but cannot be used in reactions in aqueous solvents can also be used in the present invention.
好遣ユＵ惺様
本発明においては、糖および糖アルコールのアセチル化
物を原料に使用する。Dear U.K., In the present invention, acetylated products of sugars and sugar alcohols are used as raw materials.
糖としては、グルコース、フルクトース、リボース、ア
ラビノース、マンノース、ガラクトース。Sugars include glucose, fructose, ribose, arabinose, mannose, and galactose.
キシロース等の単糖類、シヨ糖、マルトース、ラクト−
ス、セロビオース、トレハロース、パラチノース等の三
糖類、マルトトリオース、ラフィノース、セロトリオー
ス、マンノトリオース等の三糖類、セロテトロース、ス
タキオース等の四糖類がある。Monosaccharides such as xylose, sucrose, maltose, lactose
These include trisaccharides such as cellobiose, trehalose, and palatinose, trisaccharides such as maltotriose, raffinose, cellotriose, and mannotriose, and tetrasaccharides such as cellotetrose and stachyose.
糖アルコールとしては、ソルゴ１−−ル、アラビトール
、キシリトール、マンニトール、ズルシトール、マルチ
トール、ラクチトール、バラチットールなどがある。Examples of sugar alcohols include sorgol, arabitol, xylitol, mannitol, dulcitol, maltitol, lactitol, and barachitol.
アセチル化は常法によって行うことができる。Acetylation can be carried out by conventional methods.
すなわち、無水酢酸ナトリウムの触媒の存在下無水酢酸
を反応させるか、または無水酢酸とピリジンを用いてア
セチル化するのが便利である。またすべての水酸基をア
セチル化する必要はなく、有機溶媒に可溶であれば部分
的にアセチル化した糖および糖アルコールも本発明にお
いて用いることができる。That is, it is convenient to react acetic anhydride in the presence of an anhydrous sodium acetate catalyst or to acetylate using acetic anhydride and pyridine. Furthermore, it is not necessary to acetylate all hydroxyl groups, and partially acetylated sugars and sugar alcohols can also be used in the present invention as long as they are soluble in organic solvents.
脂肪酸としては、炭素数６ないし２２の飽和または不飽
和脂肪酸が好ましい。その例としては、カプロン酸、カ
プリル酸、カプリン酸、ウンデカン酸、ラウリル酸、ト
リデカン酸、ミリスチン酸。The fatty acid is preferably a saturated or unsaturated fatty acid having 6 to 22 carbon atoms. Examples are caproic acid, caprylic acid, capric acid, undecanoic acid, lauric acid, tridecanoic acid, myristic acid.
ペンタデカン酸、パルミチン酸、ヘプタデカン酸。Pentadecanoic acid, palmitic acid, heptadecanoic acid.
ステアリン酸、アラキン酸、ベヘニン酸等の飽和脂肪酸
、カプロレイン酸、リンデル酸、ミリストレイン酸、パ
ルミトレイン酸、オレイン酸、カドレイン酸、エルカ酸
、デカジエン酸、リノール酸。Saturated fatty acids such as stearic acid, arachidic acid, behenic acid, caproleic acid, lindelic acid, myristoleic acid, palmitoleic acid, oleic acid, cadreic acid, erucic acid, decadienoic acid, linoleic acid.
ヒラゴ酸、リルン酸、エイコサトリエン酸、ドコサトリ
エン酸、ヘキサデカテトラエン酸、ステアリドン酸、ア
ラキドン酸、ドコサテトラエン酸。Hylaric acid, lylunic acid, eicosatrienoic acid, docosatrienoic acid, hexadecatetraenoic acid, stearidonic acid, arachidonic acid, docosatetraenoic acid.
エイコサペンタエン酸、イワシ酸等の不飽和脂肪酸、お
よびサビニン酸、イブロール酸、ヤラピノール酸、リシ
ノール酸、フエロン酸などのヒドロキシ脂肪酸がある。These include unsaturated fatty acids such as eicosapentaenoic acid and sardine acid, and hydroxy fatty acids such as sabinic acid, ibrolic acid, yarapinoleic acid, ricinoleic acid, and feronic acid.
リパーゼには周知のように微生物由来のものと動物８原
のものとあるが、いずれも使用することができる。微生
物由来のものとしては、Ａｓｐｅｒ−ｇｉｌｌｕｓ ｎ
ｉｇｅｒ （天野製薬裂、リパーゼＡＰ−６）、Ｍｕｃ
ｏｒ屈（天野裂薬製、リパーゼＭＡＰ−１０）、Ｍｕｃ
ｏｒ ｍ１ｅｈｅｉ （ノボインダスＩ−り一社製、リ
パーゼ５Ｐ−２２５） 、Ｐｓｅｕｄｏｍｏｎａｓ
（天野裂薬製、リパーゼＰ ） 、Ｒｈ１ｚｏｐｕｓ
ｊａｐｏｎｉｃｕｓ （大阪細研社ｔ！。As is well known, there are two types of lipase: those derived from microorganisms and those derived from animal sources, and either of them can be used. As for those derived from microorganisms, Asper-gillus n.
iger (Amano Seiyaku, Lipase AP-6), Muc
orku (Amano Rippaku, lipase MAP-10), Muc
or m1ehei (manufactured by Novoindas I-Riichi Co., Ltd., lipase 5P-225), Pseudomonas
(Lipase P manufactured by Amano Hiyaku), Rh1zopus
japonicus (Osaka Seikensha t!.
リパーゼサイケンｒｌｏＯＪ ） 、Ｒｈ１ｚｏｐｕｓ
ｄｅｌｅｍａｒ（田辺製薬製、タリパーゼ） 、、
Ｃａｎｄｉｄａ ｃｙｌｉｎｄ−ｒａｃｅａ （名糖
産業語、リパーゼＭＹ）等がある。動物８原のものとし
ては、ブタすい臓由来のパンクレアチンなどがある。Lipase cyclerloOJ), Rh1zopus
delemar (Talipase, manufactured by Tanabe Pharmaceutical)
Candida cylind-racea (Meito industry term, lipase MY) and the like. Examples of animal sources include pancreatin derived from pig pancreas.
有ｔａ溶媒中の反応であるので、酵素の安定化のためリ
パーゼは固定化されていることが望ましい。Since the reaction is carried out in a solvent containing TA, it is desirable that the lipase be immobilized in order to stabilize the enzyme.
有機溶媒がベンゼンのような非極性溶媒の場合は、ある
種の酵素は遊離の状態でも活性を発現するので、その状
態で反応に供することができる。When the organic solvent is a nonpolar solvent such as benzene, certain enzymes exhibit activity even in a free state, so they can be used in the reaction in that state.
有機溶媒としては、アセチル化した糖または糖アルコー
ルおよび脂肪酸が可溶な有機溶媒であればよ（、その例
としては、ベンゼン、トルエン。The organic solvent may be any organic solvent in which acetylated sugars or sugar alcohols and fatty acids are soluble (eg, benzene, toluene, etc.).
ジエチルエーテル、クロロホルム、四塩化炭素。Diethyl ether, chloroform, carbon tetrachloride.
アセトン、メチルエチルケトン、ジオキサン、テトラヒ
ドロフランなどがある。Examples include acetone, methyl ethyl ketone, dioxane, and tetrahydrofuran.
出発反応混合液中の糖もしくは糖アルコールアセテート
と脂肪酸の比は、モル比で１対３ないし３対１の範囲が
好適である。The molar ratio of sugar or sugar alcohol acetate to fatty acid in the starting reaction mixture is preferably in the range of 1:3 to 3:1.
有Ｉａ溶媒中の基質の濃度は１〜２０％の範囲が好まし
い。をｔｌｉ３１溶媒中には若干の水の存在が必要であ
り、１％以下が好ましく、またベンゼン等の非極性溶媒
では飽和水程度でよい。The concentration of substrate in the Ia solvent is preferably in the range of 1-20%. A small amount of water is required in the tli31 solvent, preferably 1% or less, and in the case of a nonpolar solvent such as benzene, about saturated water may be sufficient.
酵素の量は、基質の合計重量の０．１〜１０９／６が
。The amount of enzyme is 0.1 to 109/6 of the total weight of the substrate.
.
好ましく、粉末状で加えればよい。Preferably, it may be added in powder form.
本発明によって合成されるエステルは、脂肪酸のほかに
アセチル基を含有しているため良好な親油性を示す。こ
の生成エステルは化粧品分野などにおける基剤やワック
ス成分として用いることができるほか、脱アセチル化に
より従来の糖もしくは糖アルコールの脂肪酸エステルと
同じ用途に用いることができる。The ester synthesized according to the present invention exhibits good lipophilicity because it contains an acetyl group in addition to fatty acids. This produced ester can be used as a base or wax component in the cosmetics field, and by deacetylation, it can be used in the same applications as conventional fatty acid esters of sugars or sugar alcohols.
以下に本発明の実施例を示す。Examples of the present invention are shown below.
実施例１
グルコースを常法に従ってアセチル化して得られたペン
タアセチルグルコース０．３９ ｇと、オレインｒ１１
０．２８ｇとを、ｐＨ７，００） ’） ７ ａｍ街？
＆ ’ｃ Ｙａ和させたベンゼン１０ｍに溶解し、これ
にＣａｎｄ １ｄａｃｙｌｉｎｄｒａｃｅａ起原の市販
リパーゼ０．５ｇを粉末の状態で加え、３７℃で９６時
間インキュベートした。反応物を高速液体クロマトグラ
フィーで分析したところ、アセチルグルコースのオレイ
ン酸モノエステル０．１０ ｇが生成していた。対脂肪
酸反応率１５．３％
実施例２
実施例１において、酵素源としてリパーゼを含有するＲ
ｈ１ｚｏｐｕｓ ｊａｐｏｎｉｃｕｓの乾燥菌体１．Ｏ
ｇを用いて反応を行ったところ、アセチルグルコースの
モノオレイン酸エステル０．１４ ｇが生成した。対脂
肪酸反応率２１６５％
実施例３
シュクロースを常法に従ってアセチル化して得られたオ
クタアセチルシュクロース０．６８ ｇと、ステアリン
酸０．２８ｇを使用し、他は実施例１と同様に反応させ
たところ、アセチルシュクロースのステアリン酸モノエ
ステル０．１４ ｇが生成した。Example 1 0.39 g of pentaacetyl glucose obtained by acetylating glucose according to a conventional method and olein r11
0.28g and pH 7,00) ') 7 am street?
&'c Ya was dissolved in 10 ml of benzene, and 0.5 g of a commercially available lipase originating from Cand 1 dacylindracea was added thereto in powder form, followed by incubation at 37° C. for 96 hours. When the reaction product was analyzed by high performance liquid chromatography, 0.10 g of oleic acid monoester of acetyl glucose was produced. Reaction rate for fatty acids 15.3% Example 2 In Example 1, R containing lipase as an enzyme source
Dried bacterial cells of h1zopus japonicus 1. O
When the reaction was carried out using g, 0.14 g of acetylglucose monooleic acid ester was produced. Reaction rate for fatty acids: 2165% Example 3 Using 0.68 g of octaacetyl sucrose obtained by acetylating sucrose according to a conventional method and 0.28 g of stearic acid, the reaction was carried out in the same manner as in Example 1. As a result, 0.14 g of stearic acid monoester of acetyl sucrose was produced.
対脂肪酸反応率１５％Fatty acid reaction rate 15%
Claims (1)
機溶媒に溶解し、これにリパーゼを加えてインキュベー
トすることを特徴とする糖もしくは糖アルコール脂肪酸
エステルの製法。A method for producing a sugar or sugar alcohol fatty acid ester, which comprises dissolving an acetylated sugar or sugar alcohol and a fatty acid in an organic solvent, adding lipase to the solution, and incubating the solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25801486A JPS63112993A (en) | 1986-10-29 | 1986-10-29 | Production of saccharide or sugarlcohol fatty acid ester by enzymatic method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP25801486A JPS63112993A (en) | 1986-10-29 | 1986-10-29 | Production of saccharide or sugarlcohol fatty acid ester by enzymatic method |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS63112993A true JPS63112993A (en) | 1988-05-18 |
Family
ID=17314328
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP25801486A Pending JPS63112993A (en) | 1986-10-29 | 1986-10-29 | Production of saccharide or sugarlcohol fatty acid ester by enzymatic method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS63112993A (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2634497A1 (en) * | 1988-07-20 | 1990-01-26 | Beghin Say Sa | NOVEL METHOD FOR OBTAINING MODIFIED SACCHAROSE DERIVATIVES IN POSITION 4 (PRIME) |
| US4959459A (en) * | 1988-03-21 | 1990-09-25 | Cerestar Holding Bv | Surface active compounds and a process for their preparation |
| FR2646439A1 (en) * | 1989-04-28 | 1990-11-02 | Gattefosse Ets Sa | Process for the preparation of sucroesters by reaction of a sugar and a fatty acid in solvent medium and in the presence of an enzyme, and sucroesters thus prepared |
| US5191071A (en) * | 1987-08-21 | 1993-03-02 | Novo Nordisk A/S | Monoesters of glycosides and a process for enzymatic preparation thereof |
| US5200328A (en) * | 1989-02-17 | 1993-04-06 | Novo Nordisk A/S | Process for producing methyl glycoside esters |
| JPH0665274A (en) * | 1991-10-29 | 1994-03-08 | Unilever Nv | Preparation of sugar ester |
| US5508182A (en) * | 1991-02-13 | 1996-04-16 | Schneider; Manfred P. | Esterification of hydrophilic polyols by adsorption onto a solid support and employing a substrate-immiscible solvent |
| JP2008043210A (en) * | 2006-08-11 | 2008-02-28 | Toyobo Co Ltd | Method for producing glycolipid |
| CN103626799A (en) * | 2013-12-03 | 2014-03-12 | 广西新方向化学工业有限公司 | Preparation of composite phytic acid sugar alcohol ester chelating agent |
-
1986
- 1986-10-29 JP JP25801486A patent/JPS63112993A/en active Pending
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5191071A (en) * | 1987-08-21 | 1993-03-02 | Novo Nordisk A/S | Monoesters of glycosides and a process for enzymatic preparation thereof |
| US4959459A (en) * | 1988-03-21 | 1990-09-25 | Cerestar Holding Bv | Surface active compounds and a process for their preparation |
| FR2634497A1 (en) * | 1988-07-20 | 1990-01-26 | Beghin Say Sa | NOVEL METHOD FOR OBTAINING MODIFIED SACCHAROSE DERIVATIVES IN POSITION 4 (PRIME) |
| US5200328A (en) * | 1989-02-17 | 1993-04-06 | Novo Nordisk A/S | Process for producing methyl glycoside esters |
| EP0458847B1 (en) * | 1989-02-17 | 1997-11-19 | Novo Nordisk A/S | A process for producing glycoside esters and compositions comprising glycoside esters |
| FR2646439A1 (en) * | 1989-04-28 | 1990-11-02 | Gattefosse Ets Sa | Process for the preparation of sucroesters by reaction of a sugar and a fatty acid in solvent medium and in the presence of an enzyme, and sucroesters thus prepared |
| US5508182A (en) * | 1991-02-13 | 1996-04-16 | Schneider; Manfred P. | Esterification of hydrophilic polyols by adsorption onto a solid support and employing a substrate-immiscible solvent |
| JPH0665274A (en) * | 1991-10-29 | 1994-03-08 | Unilever Nv | Preparation of sugar ester |
| JP2008043210A (en) * | 2006-08-11 | 2008-02-28 | Toyobo Co Ltd | Method for producing glycolipid |
| CN103626799A (en) * | 2013-12-03 | 2014-03-12 | 广西新方向化学工业有限公司 | Preparation of composite phytic acid sugar alcohol ester chelating agent |
| CN103626799B (en) * | 2013-12-03 | 2016-02-24 | 广西新方向化学工业有限公司 | A kind of preparation of composite phytic acid sugar alcohol sugar alcohol ester sequestrant |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Woudenberg‐van Oosterom et al. | Regioselective acylation of disaccharides in tert‐butyl alcohol catalyzed by Candida antarctica lipase | |
| Degn et al. | Lipase-catalysed synthesis of glucose fatty acid esters in tert-butanol | |
| EP0560408B1 (en) | Enantio- and regioselective syntheses of organic compounds using enol esters as irreversible transacylation reagents | |
| Ward et al. | Lipase-catalyzed synthesis of a sugar ester containing arachidonic acid | |
| JP4803557B2 (en) | Method for producing esterified product by lipase in aprotic organic solvent | |
| JPS63112993A (en) | Production of saccharide or sugarlcohol fatty acid ester by enzymatic method | |
| JP5997479B2 (en) | Method for synthesizing sugar fatty acid esters by enzymatic method | |
| Nott et al. | Enzymatic synthesis and surface properties of novel rhamnolipids | |
| JP4803436B2 (en) | Water-soluble mannosyl erythritol lipid and method for producing the same | |
| US5508182A (en) | Esterification of hydrophilic polyols by adsorption onto a solid support and employing a substrate-immiscible solvent | |
| EP0413307A1 (en) | Process for producing saccharide fatty acid monoesters | |
| Wu et al. | Regiospecific alkaline protease-catalyzed divinyl acyl transesterifications of primary hydroxyl groups of mono-and di-saccharides in pyridine | |
| JP5667050B2 (en) | Enzymatic synthesis of acetoacetate esters and derivatives | |
| Wu et al. | Regio-and stereo-selective synthesis of vinyl glucose ester catalyzed by an alkaline protease of Bacillus subtilis | |
| EP0571421B1 (en) | Enzymatic reverse hydrolysis of hydrophilic substrates - preparation of amphiphilic compounds | |
| EP0542996B1 (en) | Sugar-based polymers | |
| JPH0565159B2 (en) | ||
| JP3125809B2 (en) | Glycolipid production method | |
| JPH09173091A (en) | Production of saccharide fatty acid ester | |
| JPS63191802A (en) | Manufacture of fatty acid ester of cyclodextrins | |
| JPH0670789A (en) | Production of glyceroglycolipid | |
| JPH0439320B2 (en) | ||
| Riva | Enzymatic synthesis of carbohydrate esters | |
| JPH09168395A (en) | Production of saccharide fatty acid ester | |
| JPH0416194A (en) | Production of ester mixture |