GB2343101A - Antioxidant formulations - Google Patents
Antioxidant formulations Download PDFInfo
- Publication number
- GB2343101A GB2343101A GB9825719A GB9825719A GB2343101A GB 2343101 A GB2343101 A GB 2343101A GB 9825719 A GB9825719 A GB 9825719A GB 9825719 A GB9825719 A GB 9825719A GB 2343101 A GB2343101 A GB 2343101A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formulation
- fat
- vitamin
- tocopherol
- ascorbyl
- 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 abstract description 37
- 238000009472 formulation Methods 0.000 title claims abstract description 33
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 16
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 14
- 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 abstract description 21
- 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 abstract description 16
- 235000006708 antioxidants Nutrition 0.000 claims abstract description 15
- 125000003289 ascorbyl group Chemical group [H]O[C@@]([H])(C([H])([H])O*)[C@@]1([H])OC(=O)C(O*)=C1O* 0.000 claims abstract description 12
- 230000003647 oxidation Effects 0.000 claims abstract description 10
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 10
- 239000006185 dispersion Substances 0.000 claims abstract description 7
- 239000002270 dispersing agent Substances 0.000 claims abstract description 6
- 235000010389 delta-tocopherol Nutrition 0.000 claims abstract description 5
- 230000002195 synergetic effect Effects 0.000 claims abstract description 5
- 239000002446 δ-tocopherol Substances 0.000 claims abstract description 5
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 3
- 238000005580 one pot reaction Methods 0.000 claims abstract description 3
- 230000002265 prevention Effects 0.000 claims abstract description 3
- 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 34
- 238000000034 method Methods 0.000 claims description 7
- 229930003799 tocopherol Natural products 0.000 claims description 5
- 239000011732 tocopherol Substances 0.000 claims description 5
- 235000010384 tocopherol Nutrition 0.000 claims description 5
- 229960001295 tocopherol Drugs 0.000 claims description 5
- 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 5
- 239000011786 L-ascorbyl-6-palmitate Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- QAQJMLQRFWZOBN-UHFFFAOYSA-N 2-(3,4-dihydroxy-5-oxo-2,5-dihydrofuran-2-yl)-2-hydroxyethyl hexadecanoate Chemical group CCCCCCCCCCCCCCCC(=O)OCC(O)C1OC(=O)C(O)=C1O QAQJMLQRFWZOBN-UHFFFAOYSA-N 0.000 claims description 3
- 235000000072 L-ascorbyl-6-palmitate Nutrition 0.000 claims description 3
- 235000013305 food Nutrition 0.000 abstract description 6
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 229940088594 vitamin Drugs 0.000 abstract description 3
- 229930003231 vitamin Natural products 0.000 abstract description 3
- 235000013343 vitamin Nutrition 0.000 abstract description 3
- 239000011782 vitamin Substances 0.000 abstract description 3
- 238000006243 chemical reaction Methods 0.000 abstract description 2
- 238000002360 preparation method Methods 0.000 abstract description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 22
- 229930003427 Vitamin E Natural products 0.000 description 15
- 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 15
- 235000019165 vitamin E Nutrition 0.000 description 15
- 239000011709 vitamin E Substances 0.000 description 15
- 229940046009 vitamin E Drugs 0.000 description 15
- ZZZCUOFIHGPKAK-UHFFFAOYSA-N D-erythro-ascorbic acid Natural products OCC1OC(=O)C(O)=C1O ZZZCUOFIHGPKAK-UHFFFAOYSA-N 0.000 description 10
- 229930003268 Vitamin C Natural products 0.000 description 10
- 235000019154 vitamin C Nutrition 0.000 description 10
- 239000011718 vitamin C Substances 0.000 description 10
- 239000003925 fat Substances 0.000 description 5
- 235000015112 vegetable and seed oil Nutrition 0.000 description 4
- 239000008158 vegetable oil Substances 0.000 description 4
- 235000021323 fish oil Nutrition 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 239000000787 lecithin Substances 0.000 description 2
- 235000010445 lecithin Nutrition 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- -1 palmitate ester Chemical class 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- CDOUZKKFHVEKRI-UHFFFAOYSA-N 3-bromo-n-[(prop-2-enoylamino)methyl]propanamide Chemical compound BrCCC(=O)NCNC(=O)C=C CDOUZKKFHVEKRI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 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 description 1
- 230000004075 alteration Effects 0.000 description 1
- SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
- 235000010385 ascorbyl palmitate Nutrition 0.000 description 1
- 235000013734 beta-carotene Nutrition 0.000 description 1
- 239000011648 beta-carotene Substances 0.000 description 1
- 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 description 1
- 229960002747 betacarotene Drugs 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- 235000004280 healthy diet Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000693 micelle Substances 0.000 description 1
- 239000004530 micro-emulsion Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003712 vitamin E derivatives Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 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 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
- 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
- A23B2/742—Organic compounds containing oxygen
-
- 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
- A23B2/742—Organic compounds containing oxygen
- A23B2/754—Organic compounds containing oxygen containing carboxyl groups
- A23B2/758—Carboxylic acid esters
-
- 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
- A23B2/771—Organic compounds containing hetero rings
-
- 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
- C11B5/0092—Mixtures
Landscapes
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fats And Perfumes (AREA)
Abstract
A formulation used in the prevention of oxidation in the fat phase, particularly in food preparations containing poly-unsaturated fatty compounds, fat-soluble vitamins and natural colourants, characterised in that said formulation comprises a delta tocopherol homologue and an ascorbyl moiety. The formulation is a fat-soluble synergistic antioxidant formulation producible in a 'one pot' reaction vessel, which can utilise heat to increase the dispersion of the formulation. A dispersing agent may be used in preparing the formulation, with removal of the agent once the dispersion has been formed.
Description
ANTI-OXIDANT FORMULATIONS
The present invention relates to anti-oxidant formulations. Anti-oxidants are well known substances and are found in many of the foods we eat. Anti-oxidants are used to stabilise constituents in food as such constituents can be prone to oxidation and if oxidation occurs, the quality of the food can be adversely affected. Anti-oxidants are also useful as part of a healthy diet and provide a number of physiological benefits to a consumer. As a result consumers look for the presence of antioxidants in the products they use today.
One such anti-oxidant is the naturally occurring vitamin E (Tocopherol). Vitamin E is naturally fat-soluble. Vegetable oil naturally contains vitamin E however this vitamin E is lost during the purification process used in the production of vegetable oil. Therefore it is useful to add an appropriate amount of vitamin E to the purified vegetable oil to replace what was lost during the purification process. Vegetable oils are rich in unsaturated fatty acids, which require anti-oxidants to prevent oxidation.
Fat soluble vitamins A, D and beta-carotene are very susceptible to oxidation. The addition of vitamin E to products containing these fat-soluble vitamins will prevent their oxidation and therefore enhance the properties of the product in which they are contained.
Some of the colourants used in food today can undergo discolouration due to oxidation resulting in a decrease in their commercial value. Vitamin E can also assist in reducing this discolouration.
The effectiveness of vitamin E can be enhanced by the use of a synergist. An example of which is vitamin C. As vitamin E works to prevent oxidation of fats, oils etc. it is itself oxidised and as a result loses its anti-oxidant ability. In the presence of vitamin C (ascorbic acid), vitamin E is regenerated by reduction and is then available to resume its anti-oxidant effect.
However at present, the combined use of vitamin E and vitamin C is hampered in that naturally occurring vitamin C is water-soluble and not at all fat-soluble. This reduces the versatility of the synergistic combination of vitamin E and vitamin C.
In an effort to overcome this problem, research has been carried out into various methods of dissolving vitamin C into fat-soluble systems. The use of micro-emulsions sometimes referred to as'reversed micelles'is one such method. Research work carried out in this area was in relation to fish oil and the solvation of vitamin C (JAOCS, Vol. 68 No. 10 (Oct.
1991) Daeseok Han, Ock-Sook Yi and Hyun-Kyuny Shin). This system uses water and lecithin along with the fish oil. This combination allows for vitamin C to be dissolved in the fish oil and in turn act as an synergist to vitamin E. There are other chemicals which can be used as surfactants to dissolve vitamin C instead of lecithin for example dioctyl sodium sulfosuccinate and cetylbrimethyl ammonium bromide. By using any of the above synthetic chemicals, further additives are being introduced which are usually expensive and sometimes undesirable from the point of view of the customer.
It is an object of the present invention to alleviate the problems associated with the prior art.
The present invention accordingly provides formulations used in assisting in the prevention of oxidation in the fat phase, particularly in food preparations containing poly-unsaturated fatty compounds, fat-soluble vitamins and natural colourants, characterised in that said formulation comprises a delta tocopherol homologue and an ascorbyl moiety.
Preferably the delta tocopherol homologue and ascorbyl moiety are present in a ratio of 0.1 to 100 when expressed in the form;
Weight of d-delta tocopherol
Weight of ascorbyl moiety
Advantageously the tocopherol homologue is a delta isomer of tocopherol and the ascorbyl moiety is L-ascorbyl palmitate.
Conveniently the formulation is a fat-soluble synergistic anti-oxidant formulation producible in a'one pot'reaction vessel which can utilise heat to increase the dispersion of the formulation.
Preferably a method for producing the formulation involves a dispersing agent used to improve the dispersion of the components of said formulation which is removable at the end of the production process under vacuum.
The synergistic formulation is usable in fat phase (non-aqueous) systems due to the solubility of the compounds used. Vitamin E is naturally fat-soluble and the vitamin C (ascorbyl moiety) is in the form of a palmitate ester, which is fat-soluble.
D-delta Tocopherol is the most potent homologue of the fat-soluble naturally occurring forms of vitamin E and its properties as an anti-oxidant are well known. As a consequence of the anti-oxidant activity of d-delta Tocopherol, it is itself oxidised. In order to extend the life of d-delta Tocopherol a second element is required. Vitamin C (ascorbic acid) is a compound that can increase the working life of d-delta Tocopherol as an anti-oxidant. By using palmitate ester of vitamin C the ascorbic moiety is capable of regenerating oxidised d-delta Tocopherol in the fat phase by reduction of the oxidised d-delta Tocopherol it can then resume its anti-oxidant activity.
The present invention will now be described fully with reference to the following nonlimiting examples, which are given by way of example only.
Examples
Example 1.
The formulation for the anti-oxidant can be dispensed in an ampoule form for a dedicated application. The ingredients are used in the following amounts;
Ingredient Amount d-delta Tocopherol 29gms
L-ascorbyl palmitate 70gms
The ingredients are combined in a high-speed blender. The mixing vessel is warmed to 100 to increase dispersion of the formulation mixture and the formulation is dispensed into the ampoules as required
Example 2.
A dispersing agent for example ethanol and a solubilising agent, for example distilled monoglyceride at an approximate level of 0.25% W/W of the ascorbyl palmitale used are mixed with d-delta Tocopherol. This mixture is then blended (homogenised) with the ascorbyl moiety. The dispersing agent is removed under vacuum at the end of the process.
The formulation can then be packed into ampoules as required.
Example 3.
The formulation of d-delta tocopherol and ascorbyl palmitate are dispensed separately but in the ratio outlined example 1 into separate compartments of an ampoule, allowing for separate dispensation to liquid and solid components of a users process before eventual combination to form the synergistic mixture.
It will of course be understood that the invention is not limited to the specific details described herein, which are given by way of example only, and that various modifications and alterations are possible within the scope of the invention as defined in the appended claims.
Claims (9)
- Claims 1. A formulation useful in assisting in the prevention of oxidation in the fat phase, characterised in that said formulation comprises a delta tocopherol homologue and an ascorbyl moiety.
- 2. A formulation as claimed in claim 1 wherein the delta tocopherol homologue and ascorbyl moiety are present in a ratio of 0.1 to 100 when expressed in the form: Weight of d-delta tocopherol Weight of ascorbyl moiety
- 3. A formulation as claimed in claim 1 wherein the tocopherol homologue is a delta isomer of tocopherol.
- 4. A formulation as claimed in claim 1 wherein the ascorbyl moiety is L-ascorbyl palmitate.
- 5. A formulation as claimed in any one of the preceding claims wherein the formulation is a fat-soluble synergistic anti-oxidant formulation which can be produced as a"one pot" formulation.
- 6. A method for producing a formulation as claimed in claim 1 wherein a dispersing agent is used to improve the dispersion of the components of said formulation, the method including the step of removing the dispersing agent after it has performed its function.
- 7. A method as claimed in claim 6 wherein the dispersion agent is removed under vacuum.
- 8. A formulation according to claim 1, substantially as herein described with reference to the examples.
- 9. A method according to claim 6, substantially as herein described with reference to the examples.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE19990789A IES990789A2 (en) | 1998-10-27 | 1999-09-22 | Anti-oxidant formulations |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE19980887A IE980887A1 (en) | 1998-10-27 | 1998-10-27 | Anti-oxidant formulations |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9825719D0 GB9825719D0 (en) | 1999-01-20 |
| GB2343101A true GB2343101A (en) | 2000-05-03 |
| GB2343101B GB2343101B (en) | 2002-11-20 |
Family
ID=11041917
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9825719A Expired - Fee Related GB2343101B (en) | 1998-10-27 | 1998-11-25 | Anti-oxidant formulations |
Country Status (2)
| Country | Link |
|---|---|
| GB (1) | GB2343101B (en) |
| IE (2) | IE980887A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002034072A3 (en) * | 2000-10-24 | 2002-10-10 | Novartis Nutrition Ag | Synergistic antioxidant combination of delta tocols and polyphenols |
| US9132117B2 (en) | 2013-06-17 | 2015-09-15 | Kgk Synergize, Inc | Compositions and methods for glycemic control of subjects with impaired fasting glucose |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1370303A (en) * | 1970-09-08 | 1974-10-16 | Kongo Yakuhin Kk | Anti-oxidant and colour stabiliser |
| GB2169611A (en) * | 1985-01-14 | 1986-07-16 | Henkel Kgaa | Stabilization of palm kernal oil or its alkyl esters |
| GB2245812A (en) * | 1990-07-12 | 1992-01-15 | Shaklee Corp | Natural antioxidant compositions |
| US5234702A (en) * | 1992-03-19 | 1993-08-10 | Abbott Laboratories | Antioxidant system for powdered nutritional products |
-
1998
- 1998-10-27 IE IE19980887A patent/IE980887A1/en not_active IP Right Cessation
- 1998-11-25 GB GB9825719A patent/GB2343101B/en not_active Expired - Fee Related
-
1999
- 1999-09-22 IE IE19990789A patent/IES990789A2/en not_active IP Right Cessation
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1370303A (en) * | 1970-09-08 | 1974-10-16 | Kongo Yakuhin Kk | Anti-oxidant and colour stabiliser |
| GB2169611A (en) * | 1985-01-14 | 1986-07-16 | Henkel Kgaa | Stabilization of palm kernal oil or its alkyl esters |
| GB2245812A (en) * | 1990-07-12 | 1992-01-15 | Shaklee Corp | Natural antioxidant compositions |
| US5234702A (en) * | 1992-03-19 | 1993-08-10 | Abbott Laboratories | Antioxidant system for powdered nutritional products |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002034072A3 (en) * | 2000-10-24 | 2002-10-10 | Novartis Nutrition Ag | Synergistic antioxidant combination of delta tocols and polyphenols |
| US7452549B2 (en) | 2000-10-24 | 2008-11-18 | Nestec S.A. | Synergistic antioxidant combination of delta tocols and polyphenols |
| US9132117B2 (en) | 2013-06-17 | 2015-09-15 | Kgk Synergize, Inc | Compositions and methods for glycemic control of subjects with impaired fasting glucose |
| US9610276B2 (en) | 2013-06-17 | 2017-04-04 | Kgk Synergize, Inc. | Compositions and methods for glycemic control of subjects with impaired fasting glucose |
Also Published As
| Publication number | Publication date |
|---|---|
| GB2343101B (en) | 2002-11-20 |
| IE980887A1 (en) | 2000-05-03 |
| IES990789A2 (en) | 2000-07-12 |
| GB9825719D0 (en) | 1999-01-20 |
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