WO1995005747A1 - Systeme antioxydant naturel - Google Patents
Systeme antioxydant naturel Download PDFInfo
- Publication number
- WO1995005747A1 WO1995005747A1 PCT/US1994/009271 US9409271W WO9505747A1 WO 1995005747 A1 WO1995005747 A1 WO 1995005747A1 US 9409271 W US9409271 W US 9409271W WO 9505747 A1 WO9505747 A1 WO 9505747A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- composition
- oil
- fat
- antioxidant
- fats
- Prior art date
Links
- 239000003963 antioxidant agent Substances 0.000 title description 47
- 230000003078 antioxidant effect Effects 0.000 title description 42
- 239000000203 mixture Substances 0.000 claims abstract description 83
- 239000003925 fat Substances 0.000 claims abstract description 55
- 239000003921 oil Substances 0.000 claims abstract description 47
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 46
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims abstract description 33
- 239000011732 tocopherol Substances 0.000 claims abstract description 23
- 229930003799 tocopherol Natural products 0.000 claims abstract description 20
- 235000019149 tocopherols Nutrition 0.000 claims abstract description 19
- 235000010323 ascorbic acid Nutrition 0.000 claims abstract description 18
- 239000011668 ascorbic acid Substances 0.000 claims abstract description 17
- 229960005070 ascorbic acid Drugs 0.000 claims abstract description 17
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 claims abstract description 16
- 235000013734 beta-carotene Nutrition 0.000 claims abstract description 16
- 239000011648 beta-carotene Substances 0.000 claims abstract description 16
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 claims abstract description 16
- 229960002747 betacarotene Drugs 0.000 claims abstract description 16
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 claims abstract description 16
- 235000015165 citric acid Nutrition 0.000 claims abstract description 14
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 14
- 229960004106 citric acid Drugs 0.000 claims abstract description 3
- 229940067631 phospholipid Drugs 0.000 claims abstract description 3
- QUEDXNHFTDJVIY-UHFFFAOYSA-N γ-tocopherol Chemical class OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-UHFFFAOYSA-N 0.000 claims abstract 5
- 230000003647 oxidation Effects 0.000 claims description 18
- 238000007254 oxidation reaction Methods 0.000 claims description 18
- -1 ascorbic acid ester Chemical class 0.000 claims description 10
- 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 7
- 239000000787 lecithin Substances 0.000 claims description 7
- 235000010445 lecithin Nutrition 0.000 claims description 7
- 229940067606 lecithin Drugs 0.000 claims description 7
- 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 6
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 5
- 229940083466 soybean lecithin Drugs 0.000 claims description 4
- 229960001295 tocopherol Drugs 0.000 claims description 4
- WGVKWNUPNGFDFJ-DQCZWYHMSA-N β-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1C WGVKWNUPNGFDFJ-DQCZWYHMSA-N 0.000 claims description 4
- QAQJMLQRFWZOBN-LAUBAEHRSA-N L-ascorbyl-6-palmitate Chemical group CCCCCCCCCCCCCCCC(=O)OC[C@H](O)[C@H]1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-LAUBAEHRSA-N 0.000 claims description 3
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 3
- 235000010385 ascorbyl palmitate Nutrition 0.000 claims description 3
- 229940087168 alpha tocopherol Drugs 0.000 claims description 2
- 229940066595 beta tocopherol Drugs 0.000 claims description 2
- 229960000984 tocofersolan Drugs 0.000 claims description 2
- 235000004835 α-tocopherol Nutrition 0.000 claims description 2
- 239000002076 α-tocopherol Substances 0.000 claims description 2
- 235000007680 β-tocopherol Nutrition 0.000 claims description 2
- 239000011590 β-tocopherol Substances 0.000 claims description 2
- GZIFEOYASATJEH-VHFRWLAGSA-N δ-tocopherol Chemical compound OC1=CC(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-VHFRWLAGSA-N 0.000 claims 2
- GZIFEOYASATJEH-UHFFFAOYSA-N D-delta tocopherol Natural products OC1=CC(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1 GZIFEOYASATJEH-UHFFFAOYSA-N 0.000 claims 1
- 235000010389 delta-tocopherol Nutrition 0.000 claims 1
- 239000002446 δ-tocopherol Substances 0.000 claims 1
- 230000006866 deterioration Effects 0.000 abstract description 3
- 230000001590 oxidative effect Effects 0.000 abstract description 2
- 235000006708 antioxidants Nutrition 0.000 description 46
- 235000019197 fats Nutrition 0.000 description 46
- 235000019198 oils Nutrition 0.000 description 37
- 150000002978 peroxides Chemical class 0.000 description 17
- 125000002640 tocopherol group Chemical class 0.000 description 14
- 239000003760 tallow Substances 0.000 description 10
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 150000003254 radicals Chemical class 0.000 description 9
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 6
- 230000003064 anti-oxidating effect Effects 0.000 description 5
- 229910001385 heavy metal Inorganic materials 0.000 description 5
- 150000004665 fatty acids Chemical group 0.000 description 4
- 150000002432 hydroperoxides Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000003549 soybean oil Substances 0.000 description 4
- 235000012424 soybean oil Nutrition 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- JZNWSCPGTDBMEW-UHFFFAOYSA-N Glycerophosphorylethanolamin Natural products NCCOP(O)(=O)OCC(O)CO JZNWSCPGTDBMEW-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 description 3
- 150000008104 phosphatidylethanolamines Chemical class 0.000 description 3
- 150000003905 phosphatidylinositols Chemical class 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- FPPBCRLXUHYGHR-UHFFFAOYSA-N 2-tert-butyl-3-hydroxycyclohexa-2,5-diene-1,4-dione Chemical compound CC(C)(C)C1=C(O)C(=O)C=CC1=O FPPBCRLXUHYGHR-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000019634 flavors Nutrition 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 150000000996 L-ascorbic acids Chemical class 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000019482 Palm oil Nutrition 0.000 description 1
- 235000019483 Peanut oil Nutrition 0.000 description 1
- 235000019484 Rapeseed oil Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 235000014121 butter Nutrition 0.000 description 1
- 235000019282 butylated hydroxyanisole Nutrition 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 235000021466 carotenoid Nutrition 0.000 description 1
- 150000001747 carotenoids Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000013068 control sample Substances 0.000 description 1
- 235000005687 corn oil Nutrition 0.000 description 1
- 239000002285 corn oil Substances 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 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
- 230000007423 decrease Effects 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 229940013317 fish oils Drugs 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical group CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001976 improved effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000013310 margarine Nutrition 0.000 description 1
- 239000003264 margarine Substances 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 235000010384 tocopherol Nutrition 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B20/00—Preservation of edible oils or fats
- A23B20/30—Preservation of other edible oils or fats, e.g. shortenings or cooking oils
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
- A23B2/00—Preservation of foods or foodstuffs, in general
- A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
- A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
- A23B2/729—Organic compounds; Microorganisms; Enzymes
- A23B2/733—Compounds of undetermined constitution obtained from animals or plants
Definitions
- the present invention is a composition for reducing or eliminating oxidative deterioration of fats and oils. Such deterioration is often described in terms like rancid and is characterized by off odors, flavors and colors in fats or oils and products containing them. Such fat and oil containing products include foods, cosmetics, pharmaceuticals and the like.
- Fatty acid free radicals can be rendered less reactive by the addition of free radical quenchers, also known as antioxidants.
- antioxidants include carotenoids, flavonoids, BHA, BHT and tocopherols.
- Antioxidants react with the fatty acid free radicals, generating a fat hydroperoxide and an antioxidant radical.
- the antioxidant radical is much less reactive than the second fatty acid free radical otherwise produced and effectively reduces the undesirable reation rates in the oxidation cycle.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Chemical & Material Sciences (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
Abstract
L'invention porte sur une composition destinée à réduire ou éliminer les altérations, dues à l'oxydation, des graisses et huiles. Ladite composition comporte des tocophérols, du β-carotène, de l'acide citrique, de l'acide ascorbique et des phospholipides.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU76331/94A AU7633194A (en) | 1993-08-20 | 1994-08-17 | Natural antioxidant system |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US9208893A | 1993-08-20 | 1993-08-20 | |
| US08/092,088 | 1993-08-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1995005747A1 true WO1995005747A1 (fr) | 1995-03-02 |
Family
ID=22231455
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US1994/009271 WO1995005747A1 (fr) | 1993-08-20 | 1994-08-17 | Systeme antioxydant naturel |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU7633194A (fr) |
| WO (1) | WO1995005747A1 (fr) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997006697A1 (fr) * | 1995-08-21 | 1997-02-27 | Unilever N.V. | Produits alimentaires contenant un agent antioxydant |
| ES2169990A1 (es) * | 2000-03-27 | 2002-07-16 | Compania Alimentaria Del Sur D | Procedimiento para obtencion de aceite virgen extra enriquecido con vitamina e. |
| ES2169989A1 (es) * | 2000-03-27 | 2002-07-16 | Compania Alimentaria Del Sur D | Procedimiento para obtencion de aceite virgen extra enriquecido con vitaminas. |
| EP1864578A1 (fr) * | 2006-06-09 | 2007-12-12 | FUJIFILM Corporation | Composition d'émulsion à base de caroténoïde, son procédé de fabrication et produit alimentaire et cosmétique le contenant |
| US8357356B2 (en) | 2008-06-19 | 2013-01-22 | Aveda Corporation | Stabilized hydrogen peroxide compositions and methods |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5077069A (en) * | 1991-01-07 | 1991-12-31 | Kabi Pharmacia Ab | Composition of natural antioxidants for the stabilization of polyunsaturated oils |
-
1994
- 1994-08-17 WO PCT/US1994/009271 patent/WO1995005747A1/fr active Application Filing
- 1994-08-17 AU AU76331/94A patent/AU7633194A/en not_active Abandoned
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5077069A (en) * | 1991-01-07 | 1991-12-31 | Kabi Pharmacia Ab | Composition of natural antioxidants for the stabilization of polyunsaturated oils |
Non-Patent Citations (1)
| Title |
|---|
| AUTOXIDATION AND ANTIOXIDANTS, Vol. II, W.O. LUNDBERG, INTERSCIENCE PUBLISHERS, 1962, pages 991-992. * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1997006697A1 (fr) * | 1995-08-21 | 1997-02-27 | Unilever N.V. | Produits alimentaires contenant un agent antioxydant |
| ES2169990A1 (es) * | 2000-03-27 | 2002-07-16 | Compania Alimentaria Del Sur D | Procedimiento para obtencion de aceite virgen extra enriquecido con vitamina e. |
| ES2169989A1 (es) * | 2000-03-27 | 2002-07-16 | Compania Alimentaria Del Sur D | Procedimiento para obtencion de aceite virgen extra enriquecido con vitaminas. |
| EP1864578A1 (fr) * | 2006-06-09 | 2007-12-12 | FUJIFILM Corporation | Composition d'émulsion à base de caroténoïde, son procédé de fabrication et produit alimentaire et cosmétique le contenant |
| US8357356B2 (en) | 2008-06-19 | 2013-01-22 | Aveda Corporation | Stabilized hydrogen peroxide compositions and methods |
Also Published As
| Publication number | Publication date |
|---|---|
| AU7633194A (en) | 1995-03-21 |
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