JPS59113099A - 高度不飽和油組成物 - Google Patents
高度不飽和油組成物Info
- Publication number
- JPS59113099A JPS59113099A JP22326482A JP22326482A JPS59113099A JP S59113099 A JPS59113099 A JP S59113099A JP 22326482 A JP22326482 A JP 22326482A JP 22326482 A JP22326482 A JP 22326482A JP S59113099 A JPS59113099 A JP S59113099A
- Authority
- JP
- Japan
- Prior art keywords
- oil
- distillation
- distilled
- thin film
- reaction
- 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
- 239000000203 mixture Substances 0.000 title claims description 14
- 239000003921 oil Substances 0.000 claims description 117
- 235000019198 oils Nutrition 0.000 claims description 117
- 238000004821 distillation Methods 0.000 claims description 36
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Natural products C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 claims description 35
- 235000021323 fish oil Nutrition 0.000 claims description 30
- 239000010409 thin film Substances 0.000 claims description 27
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 235000019197 fats Nutrition 0.000 claims description 23
- HVYWMOMLDIMFJA-UHFFFAOYSA-N 3-cholesterol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)CCCC(C)C)C1(C)CC2 HVYWMOMLDIMFJA-UHFFFAOYSA-N 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 20
- 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 20
- 125000005456 glyceride group Chemical group 0.000 claims description 20
- 239000007788 liquid Substances 0.000 claims description 19
- 238000000199 molecular distillation Methods 0.000 claims description 18
- 239000008157 edible vegetable oil Substances 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 230000009965 odorless effect Effects 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 15
- 239000007787 solid Substances 0.000 claims description 14
- -1 cholesterin fatty acid ester Chemical class 0.000 claims description 13
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 13
- 229930195729 fatty acid Natural products 0.000 claims description 13
- 239000000194 fatty acid Substances 0.000 claims description 13
- 238000004332 deodorization Methods 0.000 claims description 12
- 235000020669 docosahexaenoic acid Nutrition 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
- 239000010696 ester oil Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 10
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 claims description 9
- 238000000746 purification Methods 0.000 claims description 9
- 238000005809 transesterification reaction Methods 0.000 claims description 9
- 229940090949 docosahexaenoic acid Drugs 0.000 claims description 8
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 claims description 7
- 239000002994 raw material Substances 0.000 claims description 7
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 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 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 claims description 5
- 235000020673 eicosapentaenoic acid Nutrition 0.000 claims description 5
- 229960005135 eicosapentaenoic acid Drugs 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 4
- 235000019485 Safflower oil Nutrition 0.000 claims description 4
- 235000019486 Sunflower oil Nutrition 0.000 claims description 4
- 239000004927 clay Substances 0.000 claims description 4
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims description 4
- 235000020778 linoleic acid Nutrition 0.000 claims description 4
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 235000005713 safflower oil Nutrition 0.000 claims description 4
- 239000003813 safflower oil Substances 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 4
- 239000002600 sunflower oil Substances 0.000 claims description 4
- 238000007796 conventional method Methods 0.000 claims description 3
- 239000002285 corn oil Substances 0.000 claims description 3
- 235000005687 corn oil Nutrition 0.000 claims description 3
- 238000004042 decolorization Methods 0.000 claims description 3
- 125000004185 ester group Chemical group 0.000 claims description 3
- 235000011187 glycerol Nutrition 0.000 claims description 3
- 239000011261 inert gas Substances 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- RZRNAYUHWVFMIP-KTKRTIGZSA-N 1-oleoylglycerol Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)CO RZRNAYUHWVFMIP-KTKRTIGZSA-N 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 239000010775 animal oil Substances 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000018044 dehydration Effects 0.000 claims description 2
- 238000006297 dehydration reaction Methods 0.000 claims description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims 3
- 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 claims 2
- 229910052708 sodium Inorganic materials 0.000 claims 2
- 239000011734 sodium Substances 0.000 claims 2
- 150000005846 sugar alcohols Polymers 0.000 claims 1
- 239000003925 fat Substances 0.000 description 20
- 235000019645 odor Nutrition 0.000 description 20
- 238000010438 heat treatment Methods 0.000 description 17
- 150000007513 acids Chemical class 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 239000003513 alkali Substances 0.000 description 7
- 230000001877 deodorizing effect Effects 0.000 description 7
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 4
- 241000251468 Actinopterygii Species 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 235000019688 fish Nutrition 0.000 description 4
- 229940013317 fish oils Drugs 0.000 description 4
- 208000019622 heart disease Diseases 0.000 description 4
- 235000013372 meat Nutrition 0.000 description 4
- 150000004671 saturated fatty acids Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- 241001125048 Sardina Species 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 230000005674 electromagnetic induction Effects 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 235000019512 sardine Nutrition 0.000 description 3
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- 240000008415 Lactuca sativa Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 208000007536 Thrombosis Diseases 0.000 description 2
- 229930003427 Vitamin E Natural products 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 235000012000 cholesterol Nutrition 0.000 description 2
- 239000003240 coconut oil Substances 0.000 description 2
- 235000019864 coconut oil Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 235000012045 salad Nutrition 0.000 description 2
- 238000007127 saponification reaction Methods 0.000 description 2
- 235000003441 saturated fatty acids Nutrition 0.000 description 2
- 239000003549 soybean oil Substances 0.000 description 2
- 235000012424 soybean oil Nutrition 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 235000019165 vitamin E Nutrition 0.000 description 2
- 229940046009 vitamin E Drugs 0.000 description 2
- 239000011709 vitamin E Substances 0.000 description 2
- KYARBIJYVGJZLB-UHFFFAOYSA-N 7-amino-4-hydroxy-2-naphthalenesulfonic acid Chemical compound OC1=CC(S(O)(=O)=O)=CC2=CC(N)=CC=C21 KYARBIJYVGJZLB-UHFFFAOYSA-N 0.000 description 1
- 241000238366 Cephalopoda Species 0.000 description 1
- 241001149724 Cololabis adocetus Species 0.000 description 1
- BKCJZNIZRWYHBN-UHFFFAOYSA-N Isophosphamide mustard Chemical compound ClCCNP(=O)(O)NCCCl BKCJZNIZRWYHBN-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 241000785681 Sander vitreus Species 0.000 description 1
- 241000269821 Scombridae Species 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000015278 beef Nutrition 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 239000011552 falling film Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000008172 hydrogenated vegetable oil Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 235000020640 mackerel Nutrition 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 235000008935 nutritious Nutrition 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 1
- 235000015277 pork Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000002797 proteolythic effect Effects 0.000 description 1
- 235000020995 raw meat Nutrition 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Fats And Perfumes (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22326482A JPS59113099A (ja) | 1982-12-20 | 1982-12-20 | 高度不飽和油組成物 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22326482A JPS59113099A (ja) | 1982-12-20 | 1982-12-20 | 高度不飽和油組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59113099A true JPS59113099A (ja) | 1984-06-29 |
| JPH0516478B2 JPH0516478B2 (enrdf_load_stackoverflow) | 1993-03-04 |
Family
ID=16795379
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22326482A Granted JPS59113099A (ja) | 1982-12-20 | 1982-12-20 | 高度不飽和油組成物 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS59113099A (enrdf_load_stackoverflow) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59172596A (ja) * | 1983-03-22 | 1984-09-29 | 高尾 正保 | 精製魚油及びその製法 |
| JPS62185794A (ja) * | 1986-02-12 | 1987-08-14 | 日清製粉株式会社 | エイコサペンタエン酸のグリセリドを含む油脂製品 |
| US4961939A (en) * | 1989-06-02 | 1990-10-09 | Nabisco Brands, Inc. | Deodorized water-in-oil emulsion containing fish oil |
| JPH03500054A (ja) * | 1986-10-21 | 1991-01-10 | ゼネラル・ミルズ・インコーポレーテッド | 油脂の脱臭とコレステロール除去を同時に行う物理的方法 |
| GR890100345A (el) * | 1988-05-27 | 1991-10-10 | Staroil Ltd | Μέ?οδος παρασκευής μιγμάτων υψηλής συγκεντρώσεως πολυακόρεστων λιπαρών οξέων και των από έλαια ζωϊκά και/ή φυτικά εστέρων αυτών,τα προϊόντα που προέρχονται από αυτήν και η χρήση τούτων για πρ οφυλακτικούς ή ?εραπευτικούς σκοπούς. |
| WO1997027274A1 (en) * | 1996-01-26 | 1997-07-31 | Abbott Laboratories | Process for the isolation of polyunsaturated fatty acids and esters thereof from complex mixtures which contain sterols and phosphorus compounds |
| WO1997027275A1 (en) * | 1996-01-26 | 1997-07-31 | Abbott Laboratories | Polyunsaturated fatty acids and fatty acid esters free of sterols and phosphorus compounds |
| JP2005036037A (ja) * | 2003-07-16 | 2005-02-10 | Kaneka Corp | 油脂組成物の製造法、及びこれを用いる油脂組成物 |
| JP2010132631A (ja) * | 2008-11-04 | 2010-06-17 | Bizen Chemical Co Ltd | カンナビノイド受容体のインバースアゴニストおよびアンタゴニスト活性を有する組成物 |
| JP2014514264A (ja) * | 2011-03-08 | 2014-06-19 | コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 脂肪酸エステルの蒸留のための方法 |
| JP2014523470A (ja) * | 2012-01-04 | 2014-09-11 | ナトゥラリス ソシエダッド アノニマ | 脂肪酸エチルエステルを包含する分散媒組成物および魚油における難分解性有機汚染物質の濃度を低下させるための方法 |
| JP5753963B1 (ja) * | 2013-09-26 | 2015-07-22 | キユーピー株式会社 | 低級アルコール脂肪酸エステル化物含有組成物の製造方法および低級アルコール脂肪酸エステル化物含有組成物 |
| LU102019B1 (de) * | 2020-08-26 | 2022-02-28 | K D Pharma Bexbach Gmbh | Verfahren zur Herstellung von Öl aus einem Mikroalgenerzeugnis |
-
1982
- 1982-12-20 JP JP22326482A patent/JPS59113099A/ja active Granted
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59172596A (ja) * | 1983-03-22 | 1984-09-29 | 高尾 正保 | 精製魚油及びその製法 |
| JPS62185794A (ja) * | 1986-02-12 | 1987-08-14 | 日清製粉株式会社 | エイコサペンタエン酸のグリセリドを含む油脂製品 |
| JPH03500054A (ja) * | 1986-10-21 | 1991-01-10 | ゼネラル・ミルズ・インコーポレーテッド | 油脂の脱臭とコレステロール除去を同時に行う物理的方法 |
| GR890100345A (el) * | 1988-05-27 | 1991-10-10 | Staroil Ltd | Μέ?οδος παρασκευής μιγμάτων υψηλής συγκεντρώσεως πολυακόρεστων λιπαρών οξέων και των από έλαια ζωϊκά και/ή φυτικά εστέρων αυτών,τα προϊόντα που προέρχονται από αυτήν και η χρήση τούτων για πρ οφυλακτικούς ή ?εραπευτικούς σκοπούς. |
| US4961939A (en) * | 1989-06-02 | 1990-10-09 | Nabisco Brands, Inc. | Deodorized water-in-oil emulsion containing fish oil |
| WO1997027275A1 (en) * | 1996-01-26 | 1997-07-31 | Abbott Laboratories | Polyunsaturated fatty acids and fatty acid esters free of sterols and phosphorus compounds |
| WO1997027274A1 (en) * | 1996-01-26 | 1997-07-31 | Abbott Laboratories | Process for the isolation of polyunsaturated fatty acids and esters thereof from complex mixtures which contain sterols and phosphorus compounds |
| US6063946A (en) * | 1996-01-26 | 2000-05-16 | Eastman Chemical Company | Process for the isolation of polyunsaturated fatty acids and esters thereof from complex mixtures which contain sterols and phosphorus compounds |
| JP2005036037A (ja) * | 2003-07-16 | 2005-02-10 | Kaneka Corp | 油脂組成物の製造法、及びこれを用いる油脂組成物 |
| JP2010132631A (ja) * | 2008-11-04 | 2010-06-17 | Bizen Chemical Co Ltd | カンナビノイド受容体のインバースアゴニストおよびアンタゴニスト活性を有する組成物 |
| JP2014514264A (ja) * | 2011-03-08 | 2014-06-19 | コグニス・アイピー・マネージメント・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 脂肪酸エステルの蒸留のための方法 |
| JP2014523470A (ja) * | 2012-01-04 | 2014-09-11 | ナトゥラリス ソシエダッド アノニマ | 脂肪酸エチルエステルを包含する分散媒組成物および魚油における難分解性有機汚染物質の濃度を低下させるための方法 |
| JP5753963B1 (ja) * | 2013-09-26 | 2015-07-22 | キユーピー株式会社 | 低級アルコール脂肪酸エステル化物含有組成物の製造方法および低級アルコール脂肪酸エステル化物含有組成物 |
| LU102019B1 (de) * | 2020-08-26 | 2022-02-28 | K D Pharma Bexbach Gmbh | Verfahren zur Herstellung von Öl aus einem Mikroalgenerzeugnis |
| WO2022043453A1 (de) * | 2020-08-26 | 2022-03-03 | K.D. Pharma Bexbach Gmbh | Verfahren zur herstellung von öl aus einem mikroalgenerzeugnis |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0516478B2 (enrdf_load_stackoverflow) | 1993-03-04 |
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