NZ235548A - Use of coenzyme q as an antioxidant in food, fat, cosmetic or pharmaceutical products - Google Patents

Use of coenzyme q as an antioxidant in food, fat, cosmetic or pharmaceutical products

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Publication number
NZ235548A
NZ235548A NZ235548A NZ23554890A NZ235548A NZ 235548 A NZ235548 A NZ 235548A NZ 235548 A NZ235548 A NZ 235548A NZ 23554890 A NZ23554890 A NZ 23554890A NZ 235548 A NZ235548 A NZ 235548A
Authority
NZ
New Zealand
Prior art keywords
fat
food
cosmetic
coenzyme
pharmaceutical product
Prior art date
Application number
NZ235548A
Inventor
Umberto Bracco
Jurg Loeliger
Francoise Saucy
Original Assignee
Produits Nestles Sa Soc D
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Produits Nestles Sa Soc D filed Critical Produits Nestles Sa Soc D
Publication of NZ235548A publication Critical patent/NZ235548A/en

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/35—Ketones, e.g. benzophenone
    • A61K8/355—Quinones
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L3/00—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs
    • A23L3/34—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals
    • A23L3/3454—Preservation of foods or foodstuffs, in general, e.g. pasteurising, sterilising, specially adapted for foods or foodstuffs by treatment with chemicals in the form of liquids or solids
    • A23L3/3463—Organic compounds; Microorganisms; Enzymes
    • A23L3/3571—Microorganisms; Enzymes
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
    • 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
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/52—Stabilizers
    • A61K2800/522—Antioxidants; Radical scavengers

Landscapes

  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Microbiology (AREA)
  • Emergency Medicine (AREA)
  • Epidemiology (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Dermatology (AREA)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Birds (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Cosmetics (AREA)
  • Fats And Perfumes (AREA)
  • Medicinal Preparation (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • General Preparation And Processing Of Foods (AREA)
  • Fodder In General (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)

Abstract

To protect an oxidation-sensitive fatty substance or a food, cosmetic or pharmaceutical product containing an oxidation-sensitive fatty substance, in particular an oil rich in polyunsaturated fatty acids, coenzyme Q is employed, if appropriate in combination with ascorbic acid and a natural emulsifier.

Description

New Zealand Paient Spedficaiion for Paient Number £35548 2355 Prior, iy ■ \ j .>-V !>r. :•• j P.c. ~ Comet's S^-5. : ; i <"///;-- '"' >*'■'■ ' ' - ■ 1 i<f^ <iJ ^ I »* t « ; i i Ti jiil'8® i t . ? j l\W k/i «ft *£«!-< Patents Form No. 5 ? - " - 3 OCT 1993 ? i Nr c NEW ZEALAND PATENTS ACT 1953 COMPLETE SPECIFICATION PROTECTION OF A FOOD, COSMETIC OR PHARMACEUTICAL PRODUCT AGAINST OXIDATION WE, SOCIETE DES PRODUITS NESTLE S.A., a Swiss company of Entre-deux-Villes, Vevey, SWITZERLAND hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement: (followed by page la) la • L ') • > < . i 1 > This invention relates to a process for the protection of a fat or a food, cosmetic or pharmaceutical product containing a fat against oxidation and to the use of coenzyme Q as an antioxidant in a food, cosmetic or pharmaceutical product containing a fat.
It is known that the coenzyme Q (CoQ), or ubiquinone, which has been isolated from the lipids of mitochondria, is involved in the basic mechanisms of energy production by respiration, in the transport of electrons in mitochondria """" and in oxidative phosphorylation. Its antioxidant activity in biological media is known, cf. for example Littarru et al., Fats and Perspectives, Drugs exptl. clin. Res. X (7), 491-496. However, in a different environment, such as a food, cosmetic or pharmaceutical product containing lipids, the oxidized form, namely quinone, could be expected to have no antioxidant activity because guinones are normally considered to be deactivation products of antioxidants of the hydroquinone type.
It has now unexpectedly been found that ubi quinone in its quinone form has a significant antioxidant activity in food, cosmetic or pharmaceutical products containing lipids, more particularly in oils rich in polyunsaturated fatty acids.
The process according to the invention is characterized in that an effective quantity of coenzyme Q is incorporated in the fat or in the food, cosmetic or pharmaceutical product.
The invention provides a process for the protection of a fat or a food, cosmetic or pharmaceutical product containing a y fat against oxidation wherein an effective quantity of coenzyme Q is incorporated in the fat or in the food, cosmetic or pharmaceutical product.
In the context of the invention, the term "food product" is to be understood in a broad sense encompassing products intended for human or animal consumption providing N 1 they contain lipids susceptible to oxidation. Similarly, 7 ^ V .a cosmetic or pharmaceutical product is to be understood in - ^'.a broad sense intended for topical application or for oral, 12 FEB1992 . enteral or parenteral administration providing the product nj>r • in question contains lipids susceptible to oxidation. 23 5 5 4 4: #» . -"-N 2 quinone derivative corresponding to the following formula ( I ) in which n = 6-10. The compound CoQ10, in which n = 10, is preferred because it is the most common and, at present, is the only industrially available derivative.
In the process or the use according to the invention, the CoQ is incorporated in the lipid phase of the food, comsetic or pharmaceutical product in a quantity of 0.1 to 5% by weight, based on the lipids present in the product. If less than 0.1% is added or used, there is a risk that the lipids of the product in question might not be adequately protected. If more than 5% is added or used, the level of protection obtained is not significantly greater than can be obtained by adding quantities in the range indicated.
In one preferred embodiment of the process according to the invention, the CoQ, which is liposoluble, is used in admixture with other antioxidants capable of producing a synergistic effect, for example water-soluble ascorbic acid (AA), in the presence of a natural emulsifier.
In the context of the invention, a "natural emulsifier" is understood to be any of the naturally occurring nonionic surfactants, for example saponins, or ionic surfactants, for example phospholipids, of animal or vegetable origin of milk, egg or soya, preferably lecithins, for example commercial lecithins, purified lecithins, soya lecithin fractions. The nature of the emulsifier used has only a secondary effect on the effect observed providing it is capable of forming a stable dispersion of AA in an anhy- 4* 235 5 4 8 drous product, for example a fat or a food containing a fat or a cosmetic or pharmaceutical product containing a fat. It is preferred to use soya lecithins or fractions P** thereof which are abundant and economical.
The preferred antioxidant mixture suitable for use in accordance with the invention advantageously contains 2.5 to 10% and preferably around 5% of CoQ and 2.5 to 20% and preferably 5 to 2 0% of AA, based on the weight of natural emulsifier.
It is of course possible to use the mixture as such or to incorporate the various components of the mixture separately from the fat to be protected. In cases where, for example, the fat is a vegetable oil already naturally containining lecithin (LC), for example soybean oil, it is 15 sufficient to add the CoQ and the AA in effective quantities.
In one advantageous embodiment of the preferred variant described above, the mixture is prepared by combining LC and CoQ with stirring at a temperature below or 20 equal to 60°C, preferably while an inert gas, for example nitrogen, is bubbled through. The AA dissolved in a polar solvent, preferably of low boiling point, for example ethanol, is then progressively added to this premix, after which the solvent is eliminated at a temperature of 60°C, 25 for example in a light vacuum. The mixture obtained is in the form of a transparent and viscous liquid. It may be used in different ways, for example by incorporation in a fat to be protected, preferably with heating, the mixture being at approximately 60"C, with vigorous stirring. 30 In another advantageous embodiment of the preferred variant described above, the AA and the CoQ are incorporated in the fat to which the lecithin has previously been added, preferably in the form of a solution in a polar solvent, for example ethyl alcohol, after which the solvent 35 is eliminated. 2355 4 The fats to be protected in accordance with the invention are preferably those most sensitive to oxidation, for example fats rich in unsaturated, particularly polyunsatu-rated, fatty acids, such as vegetable oils, for example 5 wheat germ oil, grape seed oil, corn oil, soybean oil, safflower oil, olive oil, evening primrose oil, borage oil and, in particular, black currant seed oil. Animal fats susceptible to oxidation include chicken fat, butter oil, oils of marine animals, particularly fish oil. 10 The foods, cosmetic products or pharmaceutical prod ucts to be protected are preferably those containing such fats.
The invention is illustrated by the following Examples in which percentages and parts are by weight, unless 15 otherwise indicated.
Example 1 Preparation of samples Samples of 20 g oil stabilized by addition of ubiquinone CoQ10 (formula I, n = 10) in the quantity indicated are prepared and mixed while stirring, after which the samples are placed in lacquered, sterilized 200 ml tinplate 25 cans in a quantity of 0.5 g stabilized oil per batch per can. The cans are hermetically sealed and stored at 37°C.
Accelerated oxidation test The head space of the cans containing the samples are analyzed after a certain time (in days) by determining the contents of pentane and ethane as the respective degradation products of linoleic and a-linolenic acid by oxidation and also the residual oxygen content. For comparison, the 35 same analyses are conducted with samples prepared without 235548 antioxidant. The pentane and ethane contents are determined by gas-phase chromatography while the oxygen content is determined by measurement of the paramagnetic susceptibility.
The results of this test are set out in Tables 1 and 2 below.
I .
Table 1 Fish oil sample Pentane M £10' Storage time (days) 13 °2 0 With 1% CoQ-n 2.9-10 -12 With 5% CoQ Without CoQ (comparison) 2.27•10 -12 1.52•10 -10 Fish oil sample With 0.5% CoQ Pentane M With 1% CoQ1q 4.22*10 -10 With 5% CoQ Without CoQ 6.1•10 -11 Ethane o2 Pentane Ethane M %2 M N 7.99•10~ 1114 . 7 9.10~10 1.6-10" 1 O r-i CO CO (H "15. 7 2.7* 6~10 3.64 * 10 6.45*10~ 1216. 2 -11 2.8*10 2.42 * 10 1.54•10" 1014. 3 9.10~10 1.61*10 Storage time 16 Ethane °2 Pentane Ethane M £ M M - 6.51*10" 104 6.62*10 1.06.10 .51*10" 1011. 1.17*10~1C 'l.05* 10 0 2.3 .9 -10 -8 12 . -8 -9 °2 O 1.7 9.6 0 (comparison) Legend: -: not determined, excessively high value > ') 14 Pentane Ethane 0. M M % 0 3.39«10~104.5«10~10 4.7 4.99•10-114.56•10~1011.6 17 Pentane Ethane 0 MM _0 - 0 1.62*10~101.83*10~9 7.8 cm cn err co ( Table 1 continued Storage time (days) Fish oil Pentane Ethane 0_ sample M M % With 0.1% CoQ1q - - 0 With 1% CoQ1q - 0 With 5% CoQ1q 3.76'10~105.96*10"9 0.6 Without CoQ^0 - 0 (comparison) Legend: not determined, excessively high value Po cm en en 4S. ) 1 I Table 2 Fish oil sample With 0.1% CoQ With 1% CoQ With 5% CoQ Without CoQ (comparison) Pentane M Storage time (days) 25 27 0.
Ethane M %' Pentane M Ethane M 0, .44 .10~113.51.6~11 13.6 4 . 09 .10"1;L2 . 9 .10"11 13.6 1.4.10-11 9.42 .10~1214.4 4.6.10*"10 2.61.10~1011.2 X X 6.55.10 114.17.10_1113.1 , 2.71.10 1.64 .10 28 v-10 12.1 1.01.10 -8 4.35.10 -9 4.6 Storage time (days) 30 31 Fish oil sample Pentane M Ethane M 0, Pentane M Ethane M Pentane M With 0.5% CoQ1()4.76 .10~9 2.2.10-9 5.9 0 Ethane M .-10 .-10, .-8 .-8 With 1% COQ 1.9.10 "LU 1.14.10 ■L"l2.6 3.68.10*"9 1.65.10~9 7.1 3.11.10 " 1.15.10 ** 0 -10 with 5% CoQ Without CoQ -10 -11 -11 -10 -10 3.38.10 1.76.10 11.7 8.44.10 4.97.10 12.8 8.38.10 4.12.10 9 1.31.10-8 5.47.10~9 2.9 - 0 0 Legend: -: not determined, excessively high value x: not measured ro Cj4 cn CXI OO ( t 9 Table 2 continued Storage time (days) 34 Fish oil Pentane Ethane 0 sample M M % With 0.1% CoQ10 - - 0 With 1% CoQ10 - 0 With 5% CoQ1q 5.58•10~ 9 2.15«10~9 4.4 Without CoQ1q - - 0 (comparison) Legend: - : not determined, excessively high value ro Chi en en 4>* OO 235548 The above results clearly demonstrate the antioxidant activity of CoQ10 in fish oil and black currant seed oil by comparison with the same oils without CoQ10.
Example 2 The procedure described in Example 1 is again used to measure the pentane, ethane and oxygen contents of the head space of 200 ml cans containing 0.5 g fish oil stabilized with 2.1 0.1% CoQ10 2.2 0.1% CoQ10 and 1% purified soya lecithin (Topcithin®, LC) 2.3 0.1% CoQ10, 1% Topcithin® and 1,000 ppm (parts per million) ascorbic acid (AA) and stored at 37"C for the period indicated (days).
The pentane, ethane and oxygen contents of the head space of the cans containing the fish oil without stabilizer (C:) , with 1,000 ppm AA (C2) and finally with 1,000 ppm AA + 1% LC (C3) are determined for comparison.
The results obtained are shown in Table 3 below.
I , } 1 11 Table 3 Fish oil Sample 2.1 2.1 2.3 Pentane M 12 Ethane M Storage time (days) 19 Pentane Ethane 0, M M %' Pentane M —11 —11 —1n —Q 1.38-10 9.77-10 13.3 4.96-10 6.76-10 2 1.21,10_121.04*10~1114.6 2.01•10_112.55•10~1012.2 41 Ethane M %' 0 0 — 19 —19 —19 —19 —1 H —Q .53*10 3.59*10 15.4 8.10 8.10 15.4 1.73*10 3.14*10 8 2.02*10~111.21*10~1013.1 8.56*10~101.38*10"8 0 2 . 10 -11 1.01*10 1113 8. 10 -10 0.67 *108 0.5 1.8•10-11 0.9*10_1° 12.9 7.8*10~10 0.9*10~8 0.6 - 0 0 0 Legend: not determined, excessively high value Cn on -is.
CO 235548 12 The above results clearly show that the combination of CoQ10/ AA and LC in the quantities used affords fish oil effective protection against oxidation, even after storage for 41 days, whereas without stabilizer (Cx) fish oil oxidizes rapidly from the 12th day. In addition, the use of AA alone (C2) or in admixture with LC (C3) no longer affords fish oil protection against oxidation from the 19th day. 735548 13

Claims (8)

WHAT WE CLAIM IS:
1. A process for the protection of a fat or a food, cosmetic or pharmaceutical product containing a fat against oxidation, wherein an effective quantity of 5 coenzyme Q is incorporated in the fat or in the food, cosmetic or pharmaceutical product.
2. A process as claimed in claim 1, wherein coenzyme Q is incorporated in the fat or in the food, cosmetic or pharmaceutical product in a quantity of 0.1 to 10 5% by weight, based on the weight of the fat.
3. A process as claimed in claim 1, wherein effective quantities of coenzyme Q, ascorbic acid and natural emulsifier are incorporated in the fat or in the food, cosmetic or pharmaceutical product. 15
4. A process as claimed in claim 3, wherein a mixture containing 2.5 to 10% by weight coenzyme Q and 2.5 to 20% by weight ascorbic acid, based on the weight of natural emulsifier, is incorporated in the fat or in the food, cosmetic or pharmaceutical product so that the quantity of 20 coenzyme Q is from 0.1 to 5%, based on the weight of the fat.
5. A process as claimed in claim 1, wherein the coenzyme Q is the coenzyme Q1C.
6. A fat or a food, cosmetic or pharmaceutical product 25 protected against oxidation by application of the process claimed in any one of claims 1 to 5.
7. An animal fat, protected against oxidation by application of the process claimed in any one of claims 1 to 5. 30 8. An animal fat as claimed in claim 7 which is the oil of marine animals.
9. Vegetable oil, protected against oxidation by application of the process claimed in any one of claims 1 to 5.
10. Vegetable oil as claimed in claim 9 which is black N r 35 9Acurrant seed oil. "2Vl. The use of the coenzyme Q in an effective quantity m a UW592 food, cosmetic or pharmaceutical product containing a fat to protect it against oxidation.
12. The use of the coenzyme Q in an effective quantity in combination with ascorbic acid and a natural emulsifier in a food, cosmetic or pharmaceutical product to protect it against oxidation. as described in this specification with reference to the example.
14. A fat or a food, cosaetic or pharmaceutical product as clained in claim 6 and substantially as described in this specification with reference to the example. A process as claimed in claim 1 and substantially S0CI5TS PES PRODUITS NESTLE
S.A. By Their Attorneys 3ALDWI!! so:; 4 CAREY ;v
NZ235548A 1989-10-27 1990-10-03 Use of coenzyme q as an antioxidant in food, fat, cosmetic or pharmaceutical products NZ235548A (en)

Applications Claiming Priority (1)

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CH3891/89A CH680072A5 (en) 1989-10-27 1989-10-27

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NZ235548A true NZ235548A (en) 1992-07-28

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EP (1) EP0424679B1 (en)
JP (1) JP3081226B2 (en)
AT (1) ATE131696T1 (en)
AU (1) AU637828B2 (en)
CA (1) CA2027677A1 (en)
CH (1) CH680072A5 (en)
DE (1) DE69024321T2 (en)
DK (1) DK0424679T3 (en)
ES (1) ES2081888T3 (en)
IE (1) IE71936B1 (en)
NO (1) NO301651B1 (en)
NZ (1) NZ235548A (en)
PT (1) PT95677B (en)
ZA (1) ZA908049B (en)

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ES2074395B1 (en) * 1993-02-25 1996-03-01 Lifepharma Srl PHARMACEUTICAL OR DIETETIC COMPOSITION OF HIGH ANTIOXIDANT ACTIVITY IN CARDIOVASCULAR AND / OR HEPATIC PATHOLOGIES.
JP3106820B2 (en) * 1993-12-08 2000-11-06 アールティーエー・アソシエーツ有限会社 Livestock and fish meat and their processed products freshness preservative and productivity improver
EP1068805A1 (en) * 1996-04-23 2001-01-17 Cpc International Inc. Dietetic foods and pharmaceutical preparations inhibiting blood coagulation
DE10036799A1 (en) * 2000-07-28 2002-02-07 Beiersdorf Ag New treatment for hair and scalp
TW200302055A (en) * 2002-01-18 2003-08-01 Kaneka Corp Ubiquinol-enriched fat-containing foods
TW200302054A (en) * 2002-01-18 2003-08-01 Kaneka Corp Ubiquinone-enriched foods
ATE446685T1 (en) * 2003-03-11 2009-11-15 Kaneka Corp OIL-IN-WATER EMULSION CONTAINING COENZYME Q10 AND METHOD FOR THE PRODUCTION THEREOF
ATE555674T1 (en) * 2004-04-09 2012-05-15 Kaneka Corp COMPOSITION WITH THE REDUCED FORM OF COENZYME Q10 AND CAROTENOID COMPOUND
DE202013004949U1 (en) 2013-05-31 2013-07-08 Gabriele Pütz Carbohydrate concentrate
DE102014007762A1 (en) 2013-05-31 2014-12-04 Gabriele Pütz Carbohydrate concentrate, process for its preparation and aqueous beverage concentrate
EP3695729A1 (en) 2019-02-14 2020-08-19 Vandemoortele Lipids NV Stabilized pufa containing fat compositions

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US2333656A (en) * 1942-03-31 1943-11-09 Lever Brothers Ltd Antioxidant for fats and oils
IT1191608B (en) * 1985-02-01 1988-03-23 Zambon Spa PHARMACEUTICAL COMPOSITION AND PHARMACEUTICAL FORMS THAT CONTAIN IT
IL78611A0 (en) * 1986-04-23 1986-08-31 Yeda Res & Dev Production of polyprenoid and ubiquinone-type compounds
AU606637B2 (en) * 1986-11-05 1991-02-14 George Weston Foods Limited Novel improvers for flour and yeast raised baked goods

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NO301651B1 (en) 1997-11-24
CH680072A5 (en) 1992-06-15
AU637828B2 (en) 1993-06-10
PT95677A (en) 1991-09-13
ZA908049B (en) 1991-08-28
DE69024321T2 (en) 1996-05-15
NO904647L (en) 1991-04-29
JPH03167293A (en) 1991-07-19
JP3081226B2 (en) 2000-08-28
DE69024321D1 (en) 1996-02-01
AU6374590A (en) 1991-05-02
IE71936B1 (en) 1997-03-12
NO904647D0 (en) 1990-10-26
ATE131696T1 (en) 1996-01-15
EP0424679A3 (en) 1992-04-29
PT95677B (en) 1997-09-30
DK0424679T3 (en) 1996-03-25
IE903486A1 (en) 1991-05-08
EP0424679A2 (en) 1991-05-02
CA2027677A1 (en) 1991-04-28
EP0424679B1 (en) 1995-12-20
ES2081888T3 (en) 1996-03-16

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