JPS60227687A - 糖アルコ−ル脂肪酸エステルの製造法 - Google Patents
糖アルコ−ル脂肪酸エステルの製造法Info
- Publication number
- JPS60227687A JPS60227687A JP8477784A JP8477784A JPS60227687A JP S60227687 A JPS60227687 A JP S60227687A JP 8477784 A JP8477784 A JP 8477784A JP 8477784 A JP8477784 A JP 8477784A JP S60227687 A JPS60227687 A JP S60227687A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- sugar alcohol
- acid
- lipase
- sorbitol
- 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.)
- Granted
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title claims abstract description 52
- 229930195729 fatty acid Natural products 0.000 title claims abstract description 52
- 239000000194 fatty acid Substances 0.000 title claims abstract description 52
- -1 sugar alcohol fatty acid esters Chemical class 0.000 title claims abstract description 34
- 238000004519 manufacturing process Methods 0.000 title claims description 13
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 21
- 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 claims abstract description 17
- 239000000600 sorbitol Substances 0.000 claims abstract description 17
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical compound OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims abstract description 13
- 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 claims abstract description 8
- 108090000790 Enzymes Proteins 0.000 claims description 33
- 102000004190 Enzymes Human genes 0.000 claims description 33
- 239000004367 Lipase Substances 0.000 abstract description 21
- 102000004882 Lipase Human genes 0.000 abstract description 21
- 108090001060 Lipase Proteins 0.000 abstract description 21
- 238000006243 chemical reaction Methods 0.000 abstract description 21
- 235000019421 lipase Nutrition 0.000 abstract description 21
- 239000000758 substrate Substances 0.000 abstract description 7
- 244000005700 microbiome Species 0.000 abstract description 5
- 241001465754 Metazoa Species 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 235000013373 food additive Nutrition 0.000 abstract description 3
- 239000002778 food additive Substances 0.000 abstract description 3
- 230000002441 reversible effect Effects 0.000 abstract description 3
- 102000004867 Hydro-Lyases Human genes 0.000 abstract 2
- 108090001042 Hydro-Lyases Proteins 0.000 abstract 2
- 238000011534 incubation Methods 0.000 abstract 2
- 241000179532 [Candida] cylindracea Species 0.000 abstract 1
- 229940088598 enzyme Drugs 0.000 description 32
- 238000000034 method Methods 0.000 description 22
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 15
- 235000000346 sugar Nutrition 0.000 description 14
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 11
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 11
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 11
- 239000005642 Oleic acid Substances 0.000 description 11
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 11
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 11
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000008055 phosphate buffer solution Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 150000005846 sugar alcohols Chemical class 0.000 description 6
- 230000003301 hydrolyzing effect Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 108010093096 Immobilized Enzymes Proteins 0.000 description 4
- NWGKJDSIEKMTRX-AAZCQSIUSA-N Sorbitan monooleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O NWGKJDSIEKMTRX-AAZCQSIUSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 229940049964 oleate Drugs 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 229950004959 sorbitan oleate Drugs 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 108090000604 Hydrolases Proteins 0.000 description 3
- 102000004157 Hydrolases Human genes 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 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
- 239000008117 stearic acid Substances 0.000 description 3
- UHGGERUQGSJHKR-VCDGYCQFSA-N (2r,3r,4r,5s)-hexane-1,2,3,4,5,6-hexol;octadecanoic acid Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO.CCCCCCCCCCCCCCCCCC(O)=O UHGGERUQGSJHKR-VCDGYCQFSA-N 0.000 description 2
- YWWVWXASSLXJHU-AATRIKPKSA-N (9E)-tetradecenoic acid Chemical compound CCCC\C=C\CCCCCCCC(O)=O YWWVWXASSLXJHU-AATRIKPKSA-N 0.000 description 2
- 241000159512 Geotrichum Species 0.000 description 2
- 241000235395 Mucor Species 0.000 description 2
- 241000228143 Penicillium Species 0.000 description 2
- 229930006000 Sucrose Natural products 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
- 125000005907 alkyl ester group Chemical group 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
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 238000004040 coloring Methods 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
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 230000001804 emulsifying effect Effects 0.000 description 2
- 238000006911 enzymatic reaction Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 235000021588 free fatty acids Nutrition 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 230000000813 microbial effect Effects 0.000 description 2
- 238000000593 microemulsion method Methods 0.000 description 2
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-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
- 210000000496 pancreas Anatomy 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 238000010298 pulverizing process Methods 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 150000004671 saturated fatty acids Chemical class 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 150000008163 sugars Chemical class 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 2
- 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
- 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
- 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
- GCORITRBZMICMI-CMDGGOBGSA-N (e)-dodec-4-enoic acid Chemical compound CCCCCCC\C=C\CCC(O)=O GCORITRBZMICMI-CMDGGOBGSA-N 0.000 description 1
- ZDHCZVWCTKTBRY-UHFFFAOYSA-N 12-hydroxylauric acid Chemical compound OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-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
- 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
- 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 description 1
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 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
- 239000005639 Lauric acid Substances 0.000 description 1
- GCORITRBZMICMI-UHFFFAOYSA-N Linderic acid Natural products CCCCCCCC=CCCC(O)=O GCORITRBZMICMI-UHFFFAOYSA-N 0.000 description 1
- 241000108056 Monas Species 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
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 241001655798 Taku Species 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
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 229940079919 digestives enzyme preparation Drugs 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-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
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 229960002446 octanoic acid Drugs 0.000 description 1
- 229940055695 pancreatin Drugs 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
- JIWBIWFOSCKQMA-UHFFFAOYSA-N stearidonic acid Natural products CCC=CCC=CCC=CCC=CCCCCC(O)=O JIWBIWFOSCKQMA-UHFFFAOYSA-N 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 230000002747 voluntary effect Effects 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8477784A JPS60227687A (ja) | 1984-04-25 | 1984-04-25 | 糖アルコ−ル脂肪酸エステルの製造法 |
| US06/640,892 US4614718A (en) | 1983-08-23 | 1984-08-14 | Synthesis of sugar or sugar-alcohol fatty acid esters |
| DE19843430944 DE3430944A1 (de) | 1983-08-23 | 1984-08-22 | Verfahren zur herstellung von zucker- oder zuckeralkohol-fettsaeureestern |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8477784A JPS60227687A (ja) | 1984-04-25 | 1984-04-25 | 糖アルコ−ル脂肪酸エステルの製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60227687A true JPS60227687A (ja) | 1985-11-12 |
| JPS6314948B2 JPS6314948B2 (enrdf_load_stackoverflow) | 1988-04-02 |
Family
ID=13840109
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP8477784A Granted JPS60227687A (ja) | 1983-08-23 | 1984-04-25 | 糖アルコ−ル脂肪酸エステルの製造法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60227687A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003512343A (ja) * | 1999-10-15 | 2003-04-02 | ダニスコ カルター アメリカ，インコーポレイテッド | 脂肪酸によるソルビトールの直接エステル化方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62195292A (ja) * | 1986-02-21 | 1987-08-28 | Dai Ichi Kogyo Seiyaku Co Ltd | リパ−ゼを用いる脂肪酸エステルの製法 |
-
1984
- 1984-04-25 JP JP8477784A patent/JPS60227687A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS62195292A (ja) * | 1986-02-21 | 1987-08-28 | Dai Ichi Kogyo Seiyaku Co Ltd | リパ−ゼを用いる脂肪酸エステルの製法 |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003512343A (ja) * | 1999-10-15 | 2003-04-02 | ダニスコ カルター アメリカ，インコーポレイテッド | 脂肪酸によるソルビトールの直接エステル化方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6314948B2 (enrdf_load_stackoverflow) | 1988-04-02 |
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