NO312371B1 - Fremgangsmåte ved stabilisering av umettede oljer - Google Patents
Fremgangsmåte ved stabilisering av umettede oljer Download PDFInfo
- Publication number
- NO312371B1 NO312371B1 NO20003676A NO20003676A NO312371B1 NO 312371 B1 NO312371 B1 NO 312371B1 NO 20003676 A NO20003676 A NO 20003676A NO 20003676 A NO20003676 A NO 20003676A NO 312371 B1 NO312371 B1 NO 312371B1
- Authority
- NO
- Norway
- Prior art keywords
- oil
- acid
- unsaturated
- citric acid
- unsaturated oil
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 23
- 230000000087 stabilizing effect Effects 0.000 title claims description 4
- 239000003921 oil Substances 0.000 title description 87
- 235000019198 oils Nutrition 0.000 claims description 99
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 54
- 239000000203 mixture Substances 0.000 claims description 16
- 239000003963 antioxidant agent Substances 0.000 claims description 13
- 235000006708 antioxidants Nutrition 0.000 claims description 13
- 150000007524 organic acids Chemical class 0.000 claims description 12
- 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 claims description 12
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 11
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims description 11
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 11
- 235000010385 ascorbyl palmitate Nutrition 0.000 claims description 11
- 239000000787 lecithin Substances 0.000 claims description 11
- 235000010445 lecithin Nutrition 0.000 claims description 11
- 229940067606 lecithin Drugs 0.000 claims description 11
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 9
- 230000003078 antioxidant effect Effects 0.000 claims description 9
- 239000011732 tocopherol Substances 0.000 claims description 8
- 229930003799 tocopherol Natural products 0.000 claims description 8
- 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 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 6
- 235000010384 tocopherol Nutrition 0.000 claims description 6
- 229960001295 tocopherol Drugs 0.000 claims description 6
- GJJVAFUKOBZPCB-ZGRPYONQSA-N (r)-3,4-dihydro-2-methyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2h-1-benzopyran-6-ol Chemical class OC1=CC=C2OC(CC/C=C(C)/CC/C=C(C)/CCC=C(C)C)(C)CCC2=C1 GJJVAFUKOBZPCB-ZGRPYONQSA-N 0.000 claims description 3
- BDDLHHRCDSJVKV-UHFFFAOYSA-N 7028-40-2 Chemical compound CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O BDDLHHRCDSJVKV-UHFFFAOYSA-N 0.000 claims description 3
- 239000004135 Bone phosphate Substances 0.000 claims description 3
- 125000005263 alkylenediamine group Chemical group 0.000 claims description 3
- 235000006408 oxalic acid Nutrition 0.000 claims description 3
- 229930003802 tocotrienol Natural products 0.000 claims description 3
- 239000011731 tocotrienol Substances 0.000 claims description 3
- 235000019148 tocotrienols Nutrition 0.000 claims description 3
- 229940068778 tocotrienols Drugs 0.000 claims description 3
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- 235000021323 fish oil Nutrition 0.000 claims description 2
- 235000020660 omega-3 fatty acid Nutrition 0.000 claims description 2
- 125000002640 tocopherol group Chemical class 0.000 claims description 2
- 235000019149 tocopherols Nutrition 0.000 claims description 2
- 235000013311 vegetables Nutrition 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 description 22
- 238000007254 oxidation reaction Methods 0.000 description 22
- 239000002994 raw material Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 238000010586 diagram Methods 0.000 description 4
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 4
- 150000002978 peroxides Chemical class 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 235000019197 fats Nutrition 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- 229960000984 tocofersolan Drugs 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 239000002076 α-tocopherol Substances 0.000 description 3
- 235000004835 α-tocopherol Nutrition 0.000 description 3
- 241000972773 Aulopiformes Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 229940087168 alpha tocopherol Drugs 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- -1 citric acid Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000006698 induction Effects 0.000 description 2
- 150000002632 lipids Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 235000019515 salmon Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000251730 Chondrichthyes Species 0.000 description 1
- 241000252203 Clupea harengus Species 0.000 description 1
- 241001454694 Clupeiformes Species 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- 241001125046 Sardina pilchardus Species 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 235000019513 anchovy Nutrition 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000003026 cod liver oil Substances 0.000 description 1
- 235000012716 cod liver oil Nutrition 0.000 description 1
- 238000004737 colorimetric analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- JVSWJIKNEAIKJW-UHFFFAOYSA-N dimethyl-hexane Natural products CCCCCC(C)C JVSWJIKNEAIKJW-UHFFFAOYSA-N 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000009931 harmful effect Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 235000019514 herring Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229940119224 salmon oil Drugs 0.000 description 1
- 235000019512 sardine Nutrition 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 230000004584 weight gain Effects 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B5/00—Preserving by using additives, e.g. anti-oxidants
- C11B5/0021—Preserving by using additives, e.g. anti-oxidants containing oxygen
- C11B5/0028—Carboxylic acids; Their derivates
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
- C11B3/00—Refining fats or fatty oils
- C11B3/02—Refining fats or fatty oils by chemical reaction
- C11B3/04—Refining fats or fatty oils by chemical reaction with acids
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Emergency Medicine (AREA)
- Fats And Perfumes (AREA)
- Lubricants (AREA)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO20003676A NO312371B1 (no) | 2000-07-18 | 2000-07-18 | Fremgangsmåte ved stabilisering av umettede oljer |
DE60114013T DE60114013D1 (de) | 2000-07-18 | 2001-06-27 | Verfahren zur stabilisierung ungesaettigter oele |
AU2001274695A AU2001274695A1 (en) | 2000-07-18 | 2001-06-27 | Process for stabilising unsaturated oils |
EP01941335A EP1303579B1 (de) | 2000-07-18 | 2001-06-27 | Verfahren zur stabilisierung ungesaettigter oele |
AT01941335T ATE306528T1 (de) | 2000-07-18 | 2001-06-27 | Verfahren zur stabilisierung ungesaettigter oele |
PCT/NO2001/000271 WO2002006429A1 (en) | 2000-07-18 | 2001-06-27 | Process for stabilising unsaturated oils |
US10/333,329 US20040015000A1 (en) | 2000-07-18 | 2001-06-27 | Process for stabilizing unsaturated oils |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
NO20003676A NO312371B1 (no) | 2000-07-18 | 2000-07-18 | Fremgangsmåte ved stabilisering av umettede oljer |
Publications (3)
Publication Number | Publication Date |
---|---|
NO20003676D0 NO20003676D0 (no) | 2000-07-18 |
NO20003676L NO20003676L (no) | 2002-01-21 |
NO312371B1 true NO312371B1 (no) | 2002-04-29 |
Family
ID=19911396
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO20003676A NO312371B1 (no) | 2000-07-18 | 2000-07-18 | Fremgangsmåte ved stabilisering av umettede oljer |
Country Status (7)
Country | Link |
---|---|
US (1) | US20040015000A1 (de) |
EP (1) | EP1303579B1 (de) |
AT (1) | ATE306528T1 (de) |
AU (1) | AU2001274695A1 (de) |
DE (1) | DE60114013D1 (de) |
NO (1) | NO312371B1 (de) |
WO (1) | WO2002006429A1 (de) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NO324262B1 (no) * | 2005-11-29 | 2007-09-17 | Pharmalogica As | Bruksklar sammensetning omfattende fiskeolje og juice og fremstilling av denne, samt en forseglet beholder. |
NO20081487L (no) * | 2008-03-27 | 2009-09-28 | Smartfish As | Helsefremmende drikk |
NO333013B1 (no) * | 2009-07-06 | 2013-02-18 | Smartfish As | Sammensetning omfattende bioaktive aminosyrer eller derivater derav og marin olje i en stabil olje-i-vannemulsjon, og fremgangsmate for fremstilling av nevnte sammensetning. |
CN108753457A (zh) * | 2018-08-03 | 2018-11-06 | 梁云 | 提高微生物油脂稳定性和安全性的方法 |
CN108753458A (zh) * | 2018-08-03 | 2018-11-06 | 梁云 | 提高微生物油脂稳定性和安全性的精炼工艺 |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3519662A (en) * | 1969-03-21 | 1970-07-07 | Sybron Corp | Fat separation process |
NO144727C (no) * | 1979-05-03 | 1981-10-28 | Fiskeritek Forskning | Fremgangsmaate for fremstilling av renset fiskemasse fra fet eller mager smaafisk som er kuttet i biter til bruk i ferdigmatproduksjon |
US5006281A (en) * | 1985-03-26 | 1991-04-09 | Century Laboratories, Inc. | Process for the production of a marine animal oil |
US5077069A (en) * | 1991-01-07 | 1991-12-31 | Kabi Pharmacia Ab | Composition of natural antioxidants for the stabilization of polyunsaturated oils |
US5258557A (en) * | 1992-10-09 | 1993-11-02 | Vargas Garza Hector | Process for the preparation of chelatant organic acids |
US6723370B2 (en) * | 1999-02-11 | 2004-04-20 | Cargill, Incorporated | Products comprising corn oil and corn meal obtained from corn |
-
2000
- 2000-07-18 NO NO20003676A patent/NO312371B1/no not_active IP Right Cessation
-
2001
- 2001-06-27 AT AT01941335T patent/ATE306528T1/de not_active IP Right Cessation
- 2001-06-27 WO PCT/NO2001/000271 patent/WO2002006429A1/en active IP Right Grant
- 2001-06-27 DE DE60114013T patent/DE60114013D1/de not_active Expired - Lifetime
- 2001-06-27 US US10/333,329 patent/US20040015000A1/en not_active Abandoned
- 2001-06-27 EP EP01941335A patent/EP1303579B1/de not_active Revoked
- 2001-06-27 AU AU2001274695A patent/AU2001274695A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
DE60114013D1 (de) | 2006-02-23 |
NO20003676D0 (no) | 2000-07-18 |
ATE306528T1 (de) | 2005-10-15 |
NO20003676L (no) | 2002-01-21 |
EP1303579B1 (de) | 2005-10-12 |
EP1303579A1 (de) | 2003-04-23 |
US20040015000A1 (en) | 2004-01-22 |
AU2001274695A1 (en) | 2002-01-30 |
WO2002006429A1 (en) | 2002-01-24 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |