JPS60234590A - 油脂の製造方法 - Google Patents
油脂の製造方法Info
- Publication number
- JPS60234590A JPS60234590A JP59090799A JP9079984A JPS60234590A JP S60234590 A JPS60234590 A JP S60234590A JP 59090799 A JP59090799 A JP 59090799A JP 9079984 A JP9079984 A JP 9079984A JP S60234590 A JPS60234590 A JP S60234590A
- Authority
- JP
- Japan
- Prior art keywords
- oil
- reaction
- fat
- added
- 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.)
- Granted
Links
- 238000006460 hydrolysis reaction Methods 0.000 title claims abstract description 17
- 230000007062 hydrolysis Effects 0.000 title abstract description 8
- 239000004367 Lipase Substances 0.000 claims abstract description 15
- 102000004882 Lipase Human genes 0.000 claims abstract description 15
- 108090001060 Lipase Proteins 0.000 claims abstract description 15
- 235000019421 lipase Nutrition 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 14
- 230000003301 hydrolyzing effect Effects 0.000 claims abstract description 8
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims abstract description 5
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims abstract description 5
- 238000006243 chemical reaction Methods 0.000 claims description 20
- 239000003921 oil Substances 0.000 claims description 18
- 239000003925 fat Substances 0.000 claims description 12
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 abstract description 5
- IRHTZOCLLONTOC-UHFFFAOYSA-N hexacosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCCCO IRHTZOCLLONTOC-UHFFFAOYSA-N 0.000 abstract description 4
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 abstract description 4
- 241001465754 Metazoa Species 0.000 abstract description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 abstract 2
- 244000005700 microbiome Species 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 235000019198 oils Nutrition 0.000 description 16
- 235000014113 dietary fatty acids Nutrition 0.000 description 11
- 229930195729 fatty acid Natural products 0.000 description 11
- 239000000194 fatty acid Substances 0.000 description 11
- 235000019197 fats Nutrition 0.000 description 10
- 150000004665 fatty acids Chemical class 0.000 description 10
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 238000000034 method Methods 0.000 description 8
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 7
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 5
- 150000003626 triacylglycerols Chemical class 0.000 description 5
- -1 Fatty acid esters Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000004440 column chromatography Methods 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 4
- 235000021323 fish oil Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 3
- 102000004190 Enzymes Human genes 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 229940090949 docosahexaenoic acid Drugs 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 241000222120 Candida <Saccharomycetales> Species 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- 235000014593 oils and fats Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- TYWMIZZBOVGFOV-UHFFFAOYSA-N tetracosan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCO TYWMIZZBOVGFOV-UHFFFAOYSA-N 0.000 description 2
- 239000010698 whale oil Substances 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000004255 Butylated hydroxyanisole Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- 241000588881 Chromobacterium Species 0.000 description 1
- 101100244345 Dunaliella acidophila DHA1 gene Proteins 0.000 description 1
- 108010093096 Immobilized Enzymes Proteins 0.000 description 1
- 102000019280 Pancreatic lipases Human genes 0.000 description 1
- 108050006759 Pancreatic lipases Proteins 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 241000589516 Pseudomonas Species 0.000 description 1
- 241000235527 Rhizopus Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003833 bile salt Substances 0.000 description 1
- 229940093761 bile salts Drugs 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- GVJHHUAWPYXKBD-UHFFFAOYSA-N d-alpha-tocopherol Natural products OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000010701 ester synthesis reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 229940106134 krill oil Drugs 0.000 description 1
- 230000002366 lipolytic effect Effects 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 238000003541 multi-stage reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 229960001295 tocopherol Drugs 0.000 description 1
- 229930003799 tocopherol Natural products 0.000 description 1
- 239000011732 tocopherol Substances 0.000 description 1
- 125000005457 triglyceride group Chemical group 0.000 description 1
- GVJHHUAWPYXKBD-IEOSBIPESA-N α-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-IEOSBIPESA-N 0.000 description 1
Landscapes
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59090799A JPS60234590A (ja) | 1984-05-07 | 1984-05-07 | 油脂の製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP59090799A JPS60234590A (ja) | 1984-05-07 | 1984-05-07 | 油脂の製造方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60234590A true JPS60234590A (ja) | 1985-11-21 |
| JPH0533988B2 JPH0533988B2 (enrdf_load_stackoverflow) | 1993-05-20 |
Family
ID=14008631
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP59090799A Granted JPS60234590A (ja) | 1984-05-07 | 1984-05-07 | 油脂の製造方法 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60234590A (enrdf_load_stackoverflow) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2652588A1 (fr) * | 1989-10-04 | 1991-04-05 | Medgenix Group Sa | Procede de production d'un melange de glycerides enrichis en acides gras. |
| WO1991016442A1 (en) * | 1990-04-19 | 1991-10-31 | The Procter & Gamble Company | Regio and stereoselective synthesis of triglycerides |
| WO1991016441A1 (en) * | 1990-04-20 | 1991-10-31 | The Procter & Gamble Company | Stereoselective synthesis of 1,2-diglycerides and triglycerides |
| US5089404A (en) * | 1987-12-22 | 1992-02-18 | The Japanese Research And Development Association For Bioreactor System In Food Industry | Process for the transesterification of fat and oil |
| US5137660A (en) * | 1991-03-15 | 1992-08-11 | The Procter & Gamble Company | Regioselective synthesis of 1,3-disubstituted glycerides |
| US5316927A (en) * | 1988-10-04 | 1994-05-31 | Opta Food Ingredients, Inc. | Production of monoglycerides by enzymatic transesterification |
| JP2009153485A (ja) * | 2007-12-27 | 2009-07-16 | Maruha Nichiro Seafoods Inc | 高度不飽和脂肪酸の濃縮方法 |
| JP2013121366A (ja) * | 2013-02-13 | 2013-06-20 | Maruha Nichiro Seafoods Inc | 高度不飽和脂肪酸の濃縮方法 |
-
1984
- 1984-05-07 JP JP59090799A patent/JPS60234590A/ja active Granted
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5089404A (en) * | 1987-12-22 | 1992-02-18 | The Japanese Research And Development Association For Bioreactor System In Food Industry | Process for the transesterification of fat and oil |
| US5316927A (en) * | 1988-10-04 | 1994-05-31 | Opta Food Ingredients, Inc. | Production of monoglycerides by enzymatic transesterification |
| FR2652588A1 (fr) * | 1989-10-04 | 1991-04-05 | Medgenix Group Sa | Procede de production d'un melange de glycerides enrichis en acides gras. |
| WO1991016442A1 (en) * | 1990-04-19 | 1991-10-31 | The Procter & Gamble Company | Regio and stereoselective synthesis of triglycerides |
| US5116745A (en) * | 1990-04-19 | 1992-05-26 | The Procter & Gamble Company | Process for preparing 2-acylglycerides or 1,2-diacyl diglycerides or 2,3-diacyl diglycerides |
| WO1991016441A1 (en) * | 1990-04-20 | 1991-10-31 | The Procter & Gamble Company | Stereoselective synthesis of 1,2-diglycerides and triglycerides |
| US5149642A (en) * | 1990-04-20 | 1992-09-22 | The Procter & Gamble Company | Process for preparing 2-acylglycerides or 1,2 or 2,3-diacylglycerides |
| US5137660A (en) * | 1991-03-15 | 1992-08-11 | The Procter & Gamble Company | Regioselective synthesis of 1,3-disubstituted glycerides |
| JP2009153485A (ja) * | 2007-12-27 | 2009-07-16 | Maruha Nichiro Seafoods Inc | 高度不飽和脂肪酸の濃縮方法 |
| JP2013121366A (ja) * | 2013-02-13 | 2013-06-20 | Maruha Nichiro Seafoods Inc | 高度不飽和脂肪酸の濃縮方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0533988B2 (enrdf_load_stackoverflow) | 1993-05-20 |
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