JPS5914793A - 高度不飽和脂肪酸低級アルコ−ルエステルの濃縮分離方法 - Google Patents
高度不飽和脂肪酸低級アルコ−ルエステルの濃縮分離方法Info
- Publication number
- JPS5914793A JPS5914793A JP12300782A JP12300782A JPS5914793A JP S5914793 A JPS5914793 A JP S5914793A JP 12300782 A JP12300782 A JP 12300782A JP 12300782 A JP12300782 A JP 12300782A JP S5914793 A JPS5914793 A JP S5914793A
- Authority
- JP
- Japan
- Prior art keywords
- fatty acid
- lower alcohol
- highly unsaturated
- ester
- unsaturated fatty
- 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
- -1 alcohol ester Chemical class 0.000 title claims abstract description 12
- 235000021122 unsaturated fatty acids Nutrition 0.000 title claims abstract description 9
- 150000004670 unsaturated fatty acids Chemical class 0.000 title claims abstract description 8
- 238000000926 separation method Methods 0.000 title description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims abstract description 29
- 229930195729 fatty acid Natural products 0.000 claims abstract description 29
- 239000000194 fatty acid Substances 0.000 claims abstract description 29
- 150000004665 fatty acids Chemical class 0.000 claims abstract description 23
- 150000001298 alcohols Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 20
- 239000000758 substrate Substances 0.000 claims description 3
- 239000004367 Lipase Substances 0.000 abstract description 12
- 102000004882 Lipase Human genes 0.000 abstract description 12
- 108090001060 Lipase Proteins 0.000 abstract description 12
- 235000019421 lipase Nutrition 0.000 abstract description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 9
- 239000000203 mixture Substances 0.000 abstract description 8
- 230000000694 effects Effects 0.000 abstract description 5
- 241001465754 Metazoa Species 0.000 abstract description 4
- 239000010775 animal oil Substances 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract description 4
- 239000003054 catalyst Substances 0.000 abstract description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract description 3
- 239000008158 vegetable oil Substances 0.000 abstract description 3
- 238000007796 conventional method Methods 0.000 abstract description 2
- 230000007062 hydrolysis Effects 0.000 abstract description 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 2
- 239000012141 concentrate Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000005119 centrifugation Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- 238000006386 neutralization reaction Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000021323 fish oil Nutrition 0.000 description 3
- 238000005194 fractionation Methods 0.000 description 3
- 235000020660 omega-3 fatty acid Nutrition 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 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 2
- 241000228212 Aspergillus Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- MBMBGCFOFBJSGT-KUBAVDMBSA-N all-cis-docosa-4,7,10,13,16,19-hexaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 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
- 239000004202 carbamide Substances 0.000 description 2
- 238000006317 isomerization reaction Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 230000001766 physiological effect Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 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
- 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
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000555825 Clupeidae Species 0.000 description 1
- 235000021294 Docosapentaenoic acid Nutrition 0.000 description 1
- 235000021292 Docosatetraenoic acid Nutrition 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 241000235395 Mucor Species 0.000 description 1
- 241000269821 Scombridae Species 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
- AHANXAKGNAKFSK-PDBXOOCHSA-N all-cis-icosa-11,14,17-trienoic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCCCC(O)=O AHANXAKGNAKFSK-PDBXOOCHSA-N 0.000 description 1
- 235000021342 arachidonic acid Nutrition 0.000 description 1
- 229940114079 arachidonic acid Drugs 0.000 description 1
- 210000001217 buttock Anatomy 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 235000020673 eicosapentaenoic acid Nutrition 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
- IQLUYYHUNSSHIY-HZUMYPAESA-N eicosatetraenoic acid Chemical compound CCCCCCCCCCC\C=C\C=C\C=C\C=C\C(O)=O IQLUYYHUNSSHIY-HZUMYPAESA-N 0.000 description 1
- PRHHYVQTPBEDFE-UHFFFAOYSA-N eicosatrienoic acid Natural products CCCCCC=CCC=CCCCCC=CCCCC(O)=O PRHHYVQTPBEDFE-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 235000019387 fatty acid methyl ester Nutrition 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000199 molecular distillation Methods 0.000 description 1
- YIYBQIKDCADOSF-UHFFFAOYSA-N pent-2-enoic acid Chemical compound CCC=CC(O)=O YIYBQIKDCADOSF-UHFFFAOYSA-N 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12300782A JPS5914793A (ja) | 1982-07-16 | 1982-07-16 | 高度不飽和脂肪酸低級アルコ−ルエステルの濃縮分離方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP12300782A JPS5914793A (ja) | 1982-07-16 | 1982-07-16 | 高度不飽和脂肪酸低級アルコ−ルエステルの濃縮分離方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5914793A true JPS5914793A (ja) | 1984-01-25 |
| JPH0433838B2 JPH0433838B2 (enExample) | 1992-06-04 |
Family
ID=14849939
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP12300782A Granted JPS5914793A (ja) | 1982-07-16 | 1982-07-16 | 高度不飽和脂肪酸低級アルコ−ルエステルの濃縮分離方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5914793A (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5945318A (en) * | 1994-03-08 | 1999-08-31 | Norsk Hydro A.S. | Refining oil compositions |
| WO2007119811A1 (ja) * | 2006-04-13 | 2007-10-25 | Nippon Suisan Kaisha, Ltd. | 高度不飽和脂肪酸濃縮油の製造方法 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58165796A (ja) * | 1982-03-26 | 1983-09-30 | Asahi Denka Kogyo Kk | 長鎖高度不飽和脂肪酸グリセリドの濃縮法 |
-
1982
- 1982-07-16 JP JP12300782A patent/JPS5914793A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58165796A (ja) * | 1982-03-26 | 1983-09-30 | Asahi Denka Kogyo Kk | 長鎖高度不飽和脂肪酸グリセリドの濃縮法 |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5945318A (en) * | 1994-03-08 | 1999-08-31 | Norsk Hydro A.S. | Refining oil compositions |
| WO2007119811A1 (ja) * | 2006-04-13 | 2007-10-25 | Nippon Suisan Kaisha, Ltd. | 高度不飽和脂肪酸濃縮油の製造方法 |
| US9150817B2 (en) | 2006-04-13 | 2015-10-06 | Nippon Suisan Kaisha, Ltd. | Process for preparing concentrated polyunsaturated fatty acid oil |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0433838B2 (enExample) | 1992-06-04 |
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