IE903486A1 - Protection of a food, cosmetic or pharmaceutical product against oxidation - Google Patents

Protection of a food, cosmetic or pharmaceutical product against oxidation

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Publication number
IE903486A1
IE903486A1 IE348690A IE348690A IE903486A1 IE 903486 A1 IE903486 A1 IE 903486A1 IE 348690 A IE348690 A IE 348690A IE 348690 A IE348690 A IE 348690A IE 903486 A1 IE903486 A1 IE 903486A1
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IE
Ireland
Prior art keywords
fat
cosmetic
food
pharmaceutical product
coenzyme
Prior art date
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IE348690A
Other versions
IE71936B1 (en
Inventor
Umberto Bracco
Jurg Loeliger
Francoise Saucy
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Nestle Sa
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Publication date
Application filed by Nestle Sa filed Critical Nestle Sa
Publication of IE903486A1 publication Critical patent/IE903486A1/en
Publication of IE71936B1 publication Critical patent/IE71936B1/en

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    • 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

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  • 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)
  • Nutrition Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Birds (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Dermatology (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)
  • General Preparation And Processing Of Foods (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Coloring Foods And Improving Nutritive Qualities (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
  • Fodder In General (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

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 quinones are normally considered to be deactivation products of antioxidants of the hydroquinone type.
It has now unexpectedly been found that ubi20 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 charac25 terized in that an effective quantity of coenzyme Q is incorporated in the fat or in the food, cosmetic or pharma ceutical product.
In the context of the invention, the term food product is to be understood in a broad sense encompassing 30 products intended for human or animal consumption providing they contain lipids susceptible to oxidation. Similarly, a cosmetic or pharmaceutical product is to be understood in a broad sense intended for topical application or for oral, enteral or parenteral administration providing the product in question contains lipids susceptible to oxidation.
According to the invention, CoQ is understood to be a quinone derivative corresponding to the following formula 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 % 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 0 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 2-5 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 anhyIE 903486 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 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 20% 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 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 0 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, 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.
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 is eliminated.
The fats to be protected in accordance with the invention are preferably those most sensitive to oxidation, for example fats rich in unsaturated, particularly polyunsaturated, fatty acids, such as vegetable oils, for example 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.
The foods, cosmetic products or pharmaceutical products 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 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 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 α-linolenic acid by oxidation and also the residual oxygen content. For comparison, the same analyses are conducted with samples prepared without 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.
Legend: -: not determined, excessively high value S s s S cn nj s S S S cn *r) 0 H- H· H- H- 0) H· V J H· H· H- H· ro η· 0 ft rt ft rt 3 cn 0 w rt rt rt rt 3 cn 3 *0 cr 0 cr cr cr ts cr R 9 Γ\ι cr 0 cr 3" cr Ό cr R CD c Ul R o ro o PI β Ul R o ro o 0 Π- oV> • H· Π rt o\° okP • H· H· Ul R H· R R cn Ω a Ω oV> cn π a Ω ci <#> o Ο o 0 o O 0 3 iO iO )O Ω P iO IO iO Ω R R R Ο 1-‘ R R o o o o iO o O O iO R R o o Ok Ό R tu tu kD Ό • • ro • • • • ro 1 R tu 1 3 3 Ul tu kD Ul 3 3 • tu rt tu • ui rt R • CD • • R • ro o R 3 R R O R 3 1 o ro o O 1 O ro R 1 1 1 R 1 R H‘ R R tu R o o tu tu Ul Ok M R Ok R 'J w • rt • • • • rt 1 Ul Ul 1 3 cr R Ul 03 kD 3 cr R R ro Ul Ul 03 kD ro • • 3 • • • • 3 R R ro R R R R ro O O I O O I O I O | 1 R 1 R R 1 H* 1 R R O o O R R o 1—* o o R Η» R R ok° O R tu Ul tu • • • • • Ul GJ ΓΌ R -U tu R Ok kD N) tu kD 13 • • ro • • • • ro gj R cn 1 3 3 R 00 -J R 3 3 -U to rt O • • O rt • • ro w 1 R Ok 1 ro R R 3 rt R O 1 R 3 O o ro 0 O 1 R O ro 1 R o R O R O ro R O kQ R R w ro R tu GJ R M rt • • • • rt 1 o O 1 3 cr I—1 rt Ok Ok Ok 3 cr Ul Ok ro Ok H· R tu • ro 3 3 • • • R 3 1-* R ro ro R R R O ro o O O O O 1 1 1 1 1 1 00 kD 03 P- 03 R kD ro O o kD 1-· o o O R Ul o o . . tu cn tu • tu Ok • kO -u (-> TJ w ro • • ro 1 Ok | 1 3 3 1 kD CO 1 3 3 tu rt kD kO rt • ro • • ro R 3 Η-» 3 O ro o 1 o I ro I-* 1 H 1 H O H O R M w • rt • « rt t CD 1 | 3 cr R 1 Ul Ul 1 3 cr W ro •U Ok • ro • 3 • R 3 R ro R O ro O O 1 1 1 R kD R O O o -J o O o o R o <#> o • tu R • tu 00 • U Ok Storage time (days) 0> O' t—1 Φ c s Z S S Μ rii φ 0 ri- ri- ri- ri- Φ Η- vfl 0 ft ft ft ft 3 Μ ro 3 3 3 3" 3* Ό 3* 3 Ό O μ & Φ 3 Ol μ Ο Φ 0 • · ri rt <Λ° • Η- Η- μ μ Μ ω a Ω λ» 1 0 0 0 0 • · 3 iO iO ίθ Ω -x^ μ μ μ Ο 3 o o ο ίθ O μ rt ο w to o. • φ Φ 1 I 1 3 3 rt 01 ft Φ • Φ ri μ 3 3 o Φ H- 1 3 μ ro o α Ul η • rt | vo I 1 3 3" φ 01 Φ X • 3 0 μ Φ Φ o tn 1 tn VO H- < O o ο Ο ο\° Ο Φ • Ν) μ 01 *< 3 H- vQ 3* < Φ μ C Φ Storage time (days) -J Legend: -: not determined, excessively high value s S in s 32 s s tn •tl H- I— H· H- fU p. o H- H- H- H- ro H- rt ft ft rt 3 in 0 It ft ft ft 3 cn 3" tr 3 3* •u 3* 3 3· 3· 3 3* Ό 3· Ο H· Ό O 1—' C σι o ro o ro c Ul o ro o ft <#> cK> • H· h ft <#> <#> a H· σι H- H Η1 o n Ω <*> in Q Ω Ω 0 o 0 0 0 O 0 lO ο lO O 3 lO lO lO a H t •j 0 ·· H I-1 H 0 3 O ( □ lO O o O iO 1-· M o O KJ 4» ►0 • • • « ro KJ CJ KO 3 3 t-· 03 • ok rt . . I—* , ro l-> I—1 O l-j 3 to l-> σι 13 o o , 1 o ro • . • ro 1 1 I—1 1 X 4b 4b 3 3 00 I—1 o KO • 4b ft o • I—1 a ro σι H H to w H o H 3 • • • • rt O 1 O ro 4b Ό I—* to 3 3· to 1 I—* 1 -J OK 4» , ro ω 1—* I—* l-> « . H 3 o H I—· I—1 1—1 O ro l·-1 KO KJ w o o O 1 • • • rt 1 1 1 KO OK X 4b σι 3 S' VO I—1 H< 4b to ro o O • a • 3 K ui o I—1 OK ro to H to • to O o 1 r- • • • KO 1 I I—1 KO Ό ok I—* H H> o to 00 KJ »ϋ H H H <#> o • • ro to 4b KJ to I 4b σ» 1 3 3 • X « b 4b 00 ft I-1 4b OK • a ro Ul M 1— 3 ft 1—* ok 4b 4b 13 O O ro 0 • • • • ro 1 | tl o Ul ok o 3 3 Η» KO ro H σι a KO ft 1—* kQ • • I—* . ro w ro H* H o H* 3 • • rt O O 1 o ro 1 KO OK | 3 3 L·) rt | 1 H 1 Ό σι ro o H- OO H· o H • • 3 3 H H H ro ro 4b 4b to to w O O • • • b rt 1 1 KJ H· ok KO 3 S' 1—* KO CL σι Ό H a ro 1—* ro • • • H· 3 o t—· Ό o o H I—1 H O ro to • to D) O O O 1 • Ι-» 1 | 1 1—* 00 KO H 1—· H H o 00 u> tJ h-' H H> «* o • • ro 4b KJ l·—* KJ to 1 KJ H 1 3 3 • • • • 00 rt OK to OK • • ro H· H* 3 o I O | ro 1 I—* I 00 O 1—* M • • rt 1 F* (-* 1 3 3* uj tO OI ro • * 3 Η» H* ro O O I I I—* 00 to Ul tO •o Storage time (days) O O KO Ο O O to ►3 Ql σ Φ to f X s 22 S cn Η Φ O H· H- Η- Η- 01 Η· 01 vQ 0 3 3 3 3 3 cn σ Φ 3 3 3 3 3 Τ3 3 1—1 3 Ό 0 Μ φ CL Φ C U1 Η* Ο Φ 0 • « 3 o\° • Η· Μ H- )- Μ 1 cn a Q Ο οΥ> 0 o o 0 Ο Ο • · 3 iO lO ο a 3 -— H* H Η* ο 3 3 O O Ο ιθ Η· O Η 3 ft Ο C σι Τ3 Φ cl . φ ο. Φ 1 σι | 1 3 3 3 00 3 ω Φ • 01 3 i-< Η 3 ο 3 Ο Φ Η H· 1 0) 3 <0 VQ Φ φ cl Μ Μ • 3 3 1 Η 1 1 3 3 W Η- φ σι οι ·& 3 X • 3 Φ n Η» Φ φ Ο cn 1 & cn νο οι H- ►< < o ο Ο Λ° Ο cn φ • Μ --- ·< 3* H- vQ 3 < 0> <0 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 (C1), 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. tr* ΟΠΟ to NJ NJ ω ro gj nj p • • • 0J H- iQ CJ P 1—* 3 ro ro Ό 3* 3 p CX ro o A 0) cr P (1) GJ O rt P NJ NJ cn H Ό ex • • • • • • ro ro 03 P o σι ΙΌ CJ 3 3 rt • o NJ CJ 03 rt ro P 1 • • • • 0> η O P P P P P 3 3 1 P o o o o ro Η· P 1 1 1 1 3 P P P P P ro P NJ NJ P ex o P P GJ P 10 Μ • • • • • • ft 10 o NJ in o 3 S' ro • Ι-» P 10 Qi X P • • • • • 3 0 o P P P P P ro ro 1 o o o o o ro P 1 t 1 1 1 ro o P P P P P p· P o NJ H P < P P P P P P O ro NJ GJ GO in GJ NJ P « • • • • ·< ω P •t» σ« GJ S' 00 03 00 NJ ►ΰ P· . • • • • • ro iQ 00 P in P o V0 3 3 S' . o σ o P σ rt P 1 • 1 • • £U < o P P P P P 3 CD 1 o o NJ o o ro P P 1 1 1 C o P P P ro o P o o o P 03 NJ σ M a > • • • • rt V0 σ GJ P in 3 S' • 00 o in σ ro P • • 1 • • 3 o P P P H Η ro 1 Ol o NJ O Ο 00 00 1 1 1 03 M kO O o o O P Η» Μ o . in fO NJ CTi in • • tsj 1 P « ro 1 | 1 | 3 3 GJ rt • ro Η» 3 O I ro 1 M O CJ w • rt 1 | 1 H* | 1 3 S' ro • 3 P ro o SO o o o 03 o Ο oY> o Storage time (days) N> 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.

Claims (11)

1. A process for the protection of a fat or a food, cosmetic or pharmaceutical product containing a fat against oxidation, characterized in that an effective quantity of 5 coenzyme is incorporated in the fat or in the food, cosmetic or pharmaceutical product.
2. A process as claimed in claim 1, characterized in that coenzyme 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, characterized in that 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, characterized in that a mixture containing 2.5 to 10% 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 2 0 coenzyme Q is from 0.1 to 5%, based on the weight of the fat.
5. A process as claimed in claim 1, characterized in that the coenzyme Q is the coenzyme Q 10 .
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, more particularly the oil of marine animals, protected against oxidation by application of the process claimed in any one of claims 1 to 5. 30
8. Vegetable oil, more particularly black currant seed oil, protected against oxidation by application of the process claimed in any one of claims 1 to 5.
9. The use of the coenzyme Q in a food, cosmetic or pharmaceutical product containing a fat to protect it 35 against oxidation.
10. The use of the coenzyme Q in combination with ascorbic acid and a natural emulsifier in a food, cosmetic or pharmaceutical product to protect it against oxidation.
11. A process as claimed in any of claims 1 to 5, substantially as described herein by way of Example.
IE348690A 1989-10-27 1990-09-28 Protection of a food cosmetic or pharmaceutical product against oxidation IE71936B1 (en)

Applications Claiming Priority (1)

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

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IE903486A1 true IE903486A1 (en) 1991-05-08
IE71936B1 IE71936B1 (en) 1997-03-12

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AT (1) ATE131696T1 (en)
AU (1) AU637828B2 (en)
CA (1) CA2027677A1 (en)
CH (1) CH680072A5 (en)
DE (1) DE69024321T2 (en)
DK (1) DK0424679T3 (en)
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EP1602286B1 (en) * 2003-03-11 2009-10-28 Kaneka Corporation Oil-in-water type emulsion containing coenzyme q10 and process for producing the same
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DE102014007762A1 (en) 2013-05-31 2014-12-04 Gabriele Pütz Carbohydrate concentrate, process for its preparation and aqueous beverage concentrate
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ATE131696T1 (en) 1996-01-15
NO904647D0 (en) 1990-10-26
PT95677B (en) 1997-09-30
ES2081888T3 (en) 1996-03-16
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AU637828B2 (en) 1993-06-10
ZA908049B (en) 1991-08-28
NO301651B1 (en) 1997-11-24
JPH03167293A (en) 1991-07-19
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NO904647L (en) 1991-04-29
AU6374590A (en) 1991-05-02
NZ235548A (en) 1992-07-28
DE69024321T2 (en) 1996-05-15
IE71936B1 (en) 1997-03-12
EP0424679B1 (en) 1995-12-20
JP3081226B2 (en) 2000-08-28
CA2027677A1 (en) 1991-04-28
EP0424679A3 (en) 1992-04-29
CH680072A5 (en) 1992-06-15
DE69024321D1 (en) 1996-02-01
PT95677A (en) 1991-09-13

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