EP0897264A1 - Natürliche antoxidantien - Google Patents

Natürliche antoxidantien

Info

Publication number
EP0897264A1
EP0897264A1 EP97921349A EP97921349A EP0897264A1 EP 0897264 A1 EP0897264 A1 EP 0897264A1 EP 97921349 A EP97921349 A EP 97921349A EP 97921349 A EP97921349 A EP 97921349A EP 0897264 A1 EP0897264 A1 EP 0897264A1
Authority
EP
European Patent Office
Prior art keywords
grape seeds
composition
antioxidant
freezer
lyophilized
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.)
Withdrawn
Application number
EP97921349A
Other languages
English (en)
French (fr)
Other versions
EP0897264A4 (de
Inventor
Harald P. Wulff
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel Corp
Original Assignee
Henkel Corp
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 Henkel Corp filed Critical Henkel Corp
Publication of EP0897264A1 publication Critical patent/EP0897264A1/de
Publication of EP0897264A4 publication Critical patent/EP0897264A4/de
Withdrawn legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/0012—Galenical forms characterised by the site of application
    • A61K9/0014—Skin, i.e. galenical aspects of topical compositions
    • 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
    • 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
    • A23B2/90—Preservation of foods or foodstuffs, in general by drying or kilning; Subsequent reconstitution
    • A23B2/92—Freeze drying
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/87—Vitaceae or Ampelidaceae (Vine or Grape family), e.g. wine grapes, muscadine or peppervine
    • 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
    • A61K47/46—Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts
    • 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
    • A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783—Angiosperms [Magnoliophyta]
    • A61K8/9789—Magnoliopsida [dicotyledons]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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

Definitions

  • This invention provides a composition comprising pulverized, lyophilized grape seeds, having beneficial antioxidant properties.
  • This composition may be
  • compositions which may be administered orally or topically to humans and animals, to provide protection from the harmful effects of free radicals in the human or animal body.
  • This composition also may be used as a natural food additive to prevent the oxidation of food products during
  • the present invention also provides a stable, natural source of proanthocyanodin antioxidant compounds which may be extracted by conventional means to provide a stable, highly purified, high potency antioxidant composition.
  • antioxidants are capable of protecting healthy cells from free radical damage.
  • Free radicals are unstable chemicals formed in the body during metabolism and from exposure to environmental sources, such as air pollution, cigarette smoke, and dietary fats. When there is an excessive number of free radicals in the body, they can attack healthy cells and can contribute to a number of degenerative diseases, such as cancer. The following is a list of diseases and conditions to which free radicals have been linked: Conditions Involving Multiple Organs
  • Senile dementia Contact dermatitis Parkinson disease - MPTP Photosensitive dyes Hypertensive cerebrovascular injury; Bloom syndrome cerebral trauma Allergic encephalomyelitis and other demyelinating diseases Ataxia-telangiectasia syndrome Potentiation of traumatic injury Aluminum overload Abetalipoproteinemia
  • Antioxidants quench free radicals before they have a chance to attack healthy cells. Antioxidants have been shown in the majority of studies to lower the risk for certain cancers, such as lung, stomach, cervix, breast, bladder, and
  • oral cancers Other health benefits include protection against heart diseases, cataracts, and age-related macular degeneration. While free radicals can cause or complicate many diseases, including cancer, arthritis, cataracts, and heart disease, antioxidants can help protect the body from these chronic disorders. They also enhance the body's immune system.
  • Typical antioxidant compounds used in pharmaceutical compositions include vitamin A and other carotenoid compounds, vitamin E and other tocopherols, and proanthocyanodins and their derivatives. These compounds may be produced synthetically (e.g. , by the method of U.S. Patent 2,917,539 (beta-
  • Proanthocyanodins are also nonteratogenic, nonmutagenic, and nonantigenic (thus providing for a very low risk of allergic reaction upon therapeutic administration), and have high
  • Antioxidants are also useful in the preservation of food, cosmetic, and pharmaceutical products.
  • Common antioxidants used in food, cosmetic, and pharmaceutical processing include sulfites, such as sodium bisulfite (a mixture of monosodium sulfite, NaHSO 3 , and sodium metabisulfite, Na 2 S 2 O 5 ), sodium metabisulfite, potassium metabisulfite (K 2 S : O 5 ), sulfur dioxide, and acids such as ascorbic and benzoic acid.
  • acids are unsuitable for use in many food, cosmetic, and pharmaceutical formulations.
  • exposure to sulfites, which are commonly used as antioxidants in the processing of many food products, including wine can produce acute airway obstruction and respiratory distress in sensitive individuals, particularly those suffering from asthma.
  • the present invention provides a natural antioxidant composition
  • a natural antioxidant composition comprising pulverized, lyophilized grape seeds. Grape seeds provide a natural source of antioxidant proanthocyanodins.
  • the composition of the present invention is thus a completely namral antioxidant which may readily be formulated into oral and topical pharmaceutical products for administration to humans or animals to provide protection from the harmful effects of free
  • the antioxidant composition of the present invention may also be used as a natural additive in food, cosmetic, or pharmaceutical products to prevent or retard their oxidation and spoilage.
  • the present invention also provides a stable, natural source of antioxidant
  • proanthocyanodins which may be extracted by conventional means to provide a stable, highly purified, high potency antioxidant proanthocyanodin composition for use in any application for which antioxidants are suitable.
  • the present invention provides a composition with beneficial antioxidant properties, comprising pulverized, lyophilized grape seeds.
  • a composition may be formulated as a stable, completely natural product.
  • the pulverized, lyophilized grape seeds which comprise the antioxidant composition of the present invention provide a natural source of antioxidant proanthocyanodins.
  • Proanthocyanodins form a class of natural polyphenols, defined by an exclusive property, namely the production of a red pigment (anthocyanodin) by the Bate-Smith reaction (Bate-Smith, E.C , and Swain, T. (1953) Chemistry & Industry pp 377-378).
  • Natural proanthocyanodins are typically an oligomeric mixture of proanthocyanodins having the general formula:
  • grape seeds may be ground or pulverized into a fine powder using any suitable method.
  • the whole or pulverized grape seeds are then lyophilized (freeze-dried) in order to remove at least 99%, and preferably more than 99% , of the water naturally contained in the grape seeds.
  • Lyophilization is a process of drying in which water is sublimed from the product after it is frozen. This serves to enhance their stability and shelf life, while maintaining the status of the grape seeds as a completely natural product. Lyophilization may be carried out using any means known in the art. Lyophilization essentially comprises freezing the product (in this case, pulverized grape seeds), evacuating the air from the freezer such that the air pressure falls usually below 0.1 torr (ice sublimes at pressures below 3 torr), subliming ice in the freezer on a cold condensing surface at a temperature below that of the product, and introducing heat to the product under controlled conditions, thus providing energy for sublimation of the ice in the product while maintaining the product below its eutectic temperature.
  • freezing the product in this case, pulverized grape seeds
  • evacuating the air from the freezer such that the air pressure falls usually below 0.1 torr (ice sublimes at pressures below 3 torr)
  • the grape seeds of the present invention may be used directly in any application in which a completely natural antioxidant is desired.
  • the pulverized, lyophilized grape seeds of the present invention are subject to conventional chemical extraction procedures in order to extract the antioxidant proanthocyanodins contained therein. This provides a stable, highly purified, high potency antioxidant proanthocyanodin composition for use in any application for which antioxidants are suitable. Proanthocyanodins may be extracted from
  • grapeseeds by any method known in the art, for example, by the method of U.S.
  • Patents 3,436,407 and 4,698,360 are disclosed.
  • proanthocyanodins are extracted from grape seeds by the following steps: grape seeds are first pulverized and extracted with boiling water (the extracted grape seeds can then be compressed or pressed to physically remove all liquid possible). The liquid is cooled to 20 ° C and filtered. Sodium chloride is added to saturation, and the precipitate formed is separated. The filtrate is extracted 3X with ethyl acetate at the rate of 1/10 the volume of
  • the ethyl acetate collected is dried on anhydrous Na 2 SO 4 and brought back to 1/5 of its volume by distillation under reduced pressure. It is then poured into three volumes of chloroform, while stirring mechanically.
  • the proanthocyanodins precipitate out, and may be collected by filtration. They may be further purified by redissolution in ethyl acetate and reprecipitation in chloroform. They may be finally washed with chloroform and dried at reduced pressure at a temperature no higher than 50 ° C.
  • the grape seeds are lyophilized first; in this form they may be stored for long periods prior to pulverizing and/or extraction of proanthocyanodins.
  • the lyophilized grape seeds may be pulverized while in the lyophilized state; alternatively, the grape seeds may be reconstituted prior to pulverizing.
  • the present invention also provides an oral antioxidant pharmaceutical composition.
  • a composition may comprise the pulverized, lyophilized grapeseeds according to the present invention, where a completely natural
  • the composition may comprise purified proanthocyanodins extracted from pulverized, lyophilized grapeseeds, where a more purified antioxidant composition is desired.
  • the oral antioxidant pharmaceutical composition according to the present invention will be described in detail below.
  • a pharmaceutically acceptable carrier suitable for oral administration.
  • compositions of the present invention can be made by conventional compounding procedures known in the pharmaceutical art, that is, by mixing the active substances with edible pharmaceutically acceptable non-toxic inert, solid or liquid carriers and/or excipients suitable for systemic administration and conventionally used in oral dosage forms.
  • carriers for use in the present invention will be natural carriers, such as edible oils.
  • edible oil may be a vegetable oil such as avocado, coconut, corn, grape seed, palm, peanut, olive, sesame, soya, rapeseed, or walnut oil or any other edible vegetable oil or mixture of one or more of these oils. Additionally, edible, non- toxic pharmaceutically acceptable stabilizers usually used as stabilizers in oral dosage forms or edible, non-toxic salts thereof can be included in the
  • the stabilizer will be beeswax or silica. All the above carriers, excipients and stabilizers are intended to include only those suitable for oral administration and all are conventional and known to the pharmaceutical art.
  • the pharmaceutical compositions for oral administration may be in the
  • the patient ingests the composition preferably daily to obtain the benefit of the administration of the proanthocyanodins.
  • the dosage of the antioxidant composition of the present invention administered to a patient will vary depending upon several factors, including, but not limited to, the age and weight of the patient, the general health of the patient, the severity of the symptoms, and the like.
  • the present invention also provides topical antioxidant pharmaceutical compositions, and cosmetic compositions containing antioxidants. Such a
  • composition may comprise the pulverized, lyophilized grapeseeds according to the present invention, where a completely natural product is desired.
  • composition may comprise purified proanthocyanodins extracted from pulverized, lyophilized grapeseeds, where a more purified antioxidant composition is desired.
  • the topical antioxidant may comprise the pulverized, lyophilized grapeseeds according to the present invention, where a completely natural product is desired.
  • the composition may comprise purified proanthocyanodins extracted from pulverized, lyophilized grapeseeds, where a more purified antioxidant composition is desired.
  • the topical antioxidant may comprise the pulverized, lyophilized grapeseeds according to the present invention, where a completely natural product is desired.
  • the topical antioxidant may comprise the topical antioxidant
  • compositions or cosmetic composition according to the present invention will further comprise a carrier suitable for topical administration.
  • the pulverized lyophilized grape seeds which comprise the natural antioxidant
  • composition of the present invention may be used in all galenical forms normally used for topical application, in particular lotion or serum-type solutions or dispersions, liquid or semi-liquid milk emulsions produced by dispersions of a fatty phase in an aqueous phase (O/W) or the reverse (W/O), or cream- or gel- type emulsions having a soft consistency, or microgranulates or vesicular ionic and/or non- ionic dispersions.
  • lotion or serum-type solutions or dispersions liquid or semi-liquid milk emulsions produced by dispersions of a fatty phase in an aqueous phase (O/W) or the reverse (W/O)
  • cream- or gel- type emulsions having a soft consistency or microgranulates or vesicular ionic and/or non- ionic dispersions.
  • the natural antioxidant composition of the present invention may be added to a wide variety of products for topical application, including makeup, creams for cleansing, protecting, treating, or caring for the skin, in particular, the face, hands, and feet (e.g. , day and night creams, makeup removal creams, foundation creams and sunscreens), liquid foundations, makeup removal lotions, protective or skin-care body lotions, sunscreen lotions, skin care lotions, gels, or foams, such as cleansing, sunscreen, and artificial tanning lotions, bath preparations, deodorant compositions, after-shave gels or lotions, depilatory creams, and compositions used for insect stings and against pain.
  • the topical compositions according to the invention may also consist of solid preparations used for soaps and cleansing bars.
  • topical compositions according to the present invention may also contain additives customarily used in cosmetics, such as
  • water-absorbent or lipophilic gelling agents water-absorbent or lipophilic active ingredients, preservatives, solvents, perfumes, fillers, screens, and coloring substances.
  • the quantities of these various additives are those conventionally used in cosmetics; for example, from 0.1 % to 10% of the total weight of the
  • additives may, depending on the nature thereof, be added to the fatty phase, the aqueous phase, and/or in lipidic spherules.
  • lipidic spherules Preferably, such additives are natural substances.
  • Oils suitable for use in the topical compositions of the present invention include mineral oils (e.g. , vaseline oil), vegetable oils (e.g., sunflower oil), animal oils (e.g., perhydrosqualene), synthetic oils (e.g., Purcellin oil), silicone containing oils, (e.g. , cyclomethicone) and fluorinated oils (e.g. , perfluoropolyethers).
  • mineral oils e.g. , vaseline oil
  • vegetable oils e.g., sunflower oil
  • animal oils e.g., perhydrosqualene
  • synthetic oils e.g., Purcellin oil
  • silicone containing oils e.g. , cyclomethicone
  • fluorinated oils e.g. , perfluoropolyethers.
  • Fatty alcohols and fatty acids e.g. , stearic acid
  • the oil is a natural vegetable oil.
  • Emulsifiers suitable for use in the topical compositions of the present invention include, for example, glycerol stearate, polysorbate 60, and a PEG-6/PEG-32/glycol stearate mixture (Tefose ® ).
  • Solvents suitable for use in the topical compositions of the present invention include, for example, the lower alcohols, in particular ethanol and
  • carboxyvinyl polymers include carboxyvinyl polymers, acrylic copolymers (e.g. , acrylate/alkylacrylate copolymers), poly aery lamides, polysaccharides (e.g. , hydroxypropylcellulose), and, preferably, natural gums and clays.
  • Lipophilic gelling agents suitable for use in the topical compositions of the present invention include carboxyvinyl polymers, acrylic copolymers (e.g. , acrylate/alkylacrylate copolymers), poly aery lamides, polysaccharides (e.g. , hydroxypropylcellulose), and, preferably, natural gums and clays.
  • Lipophilic gelling agents suitable for use in the topical compositions of the present invention include carboxyvinyl polymers, acrylic copolymers (e.g. , acrylate/alkylacrylate copolymers), poly aery lamides, polysaccharides (e.g. , hydroxy
  • modified clays e.g., bentonites
  • the metallic salts of fatty acids e.g. , aluminum stearates
  • hydrophobic silica e.g., silica
  • Water-absorbing active ingredients include proteins and protein hydrolysates, amino acids, polyalcohols, urea, allantoin, sugars and sugar
  • Lipophilic active ingredients include retinol (vitamin A) and derivatives thereof, tocopherol (vitamin E) and derivatives thereof, essential fatty acids,
  • ceramides ceramides, essential oils, and salicylic acid and derivatives thereof.
  • the pulverized, lyophilized grape seeds of the present invention may also be combined with active ingredients intended, in particular, for the prevention and/or treatment of skin disorders.
  • active ingredients may include, for example:
  • agents modulating the differentiation, proliferation, and/or skin pigmentation such as retinoic acid and isomers thereof, retinol and esters thereof, vitamin D and derivatives thereof, estrogens such as estradiol, kojik acid and hydroquinone;
  • - antibacterial agents such as clindamycin phosphate, erythromycin, tetracycline antibiotics, and the like
  • - antifungal agents such as imidazoles (e.g. , econazole, ketoconazole,
  • miconazole and salts thereof, polyenes (e.g. , amphotericin B), allylamines (e.g. , terbinafine, octopirox), and the like;
  • polyenes e.g. , amphotericin B
  • allylamines e.g. , terbinafine, octopirox
  • - steroidal anti-inflammatory agents such as hydrocortisone, betamethasone valerate, clobetasol propionate, and the like, or nonsteroidal anti- inflammatory agents, such as ibuprofen, ketoprofen, and salts thereof, diclofenac
  • - anesthetic agents such as lidocaine chlorhydrate and derivatives thereof, and the like;
  • - anti-pruriginous agents such as thenaldine, trimeprazine, and cyproheptadine, and the like;
  • antiviral agents such as acyclovir, and the like
  • - keratolytic agents such as a- and ⁇ -hydroxycarboxylic and ⁇ - ketocarboxylic acids, and salts, amides, and esters thereof, hydroxy acids, such as glycolic, lactic, salicylic, and citric acid, and, in general, fruit acids, and the like;
  • antioxidants such as ⁇ -tocopherol and esters thereof, superoxide dismutases, metal chelating agents, ascorbic acid and esters thereof, and the like;
  • - anti-seborrhea agents such as progesterone, and the like;
  • the present invention also includes a method for quenching free radicals comprising administering to a mammal, including a human, in need of such treatment an antioxidant effective amount of an antioxidant composition according to the present invention.
  • a method for quenching free radicals comprising administering to a mammal, including a human, in need of such treatment an antioxidant effective amount of an antioxidant composition according to the present invention.
  • Such a method may comprise administering
  • the method may comprise administering an antioxidant effective amount of purified proanthocyanodins extracted from pulverized, lyophilized grapeseeds.
  • This method may be practiced by administration of an antioxidant composition according to the present invention by itself, or in combination with other active ingredients, including other antioxidants, and/or therapeutic agents in
  • Suitable for use herein are any compatible drugs that are effective by the same or other mechanisms for the intended purpose, or drugs that are complementary to those of the present agents.
  • Examples include carotenoids (e.g. , beta carotene derived from Dunaliella salina) and vitamins (e.g. , natural tocopherols derived from soybean oil, such as d- ⁇ -tocopherol), among others.
  • the compatible compounds will preferably be natural antioxidants.
  • the compounds utilized in combination therapy may be administered simultaneously, in either separate or combined formulations, or at different times than the compositions according to the present invention, e.g. , sequentially, such that a combined effect is achieved.
  • the amounts and regime of administration will be adjusted by the practitioner, by preferably initially lowering their standard doses and then titrating the results obtained.
  • Antioxidant food additive The present invention also provides an antioxidant composition which may be added to food products to prevent oxidation.
  • a composition may comprise the pulverized, lyophilized grapeseeds according to the present invention, where a completely natural product is desired.
  • the composition may comprise purified proanthocyanodins extracted from pulverized, lyophilized grapeseeds, where a more purified antioxidant composition is desired.
  • the antioxidant composition of the present invention is suitable for addition to wine, in order to prevent oxidation of the wine. In the typical fermentation process, wines may be dosed with the antioxidant composition of the present invention at any time during fermentation.
  • wines are dosed with the antioxidant composition of the present invention at the time of bottling, as a substitute for all or part of the sulfur dioxide typically used to prevent oxidation in winemaking.
  • the present invention also provides a process for preventin the oxidation of food products comprising adding to a food product an antioxidant effective amount of an antioxidant composition according to the present invention during the preparation or processing of the food product. While the invention has been described and illustrated herein by

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Veterinary Medicine (AREA)
  • Chemical & Material Sciences (AREA)
  • Epidemiology (AREA)
  • Botany (AREA)
  • Medicinal Chemistry (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biotechnology (AREA)
  • Mycology (AREA)
  • Microbiology (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Medical Informatics (AREA)
  • Alternative & Traditional Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Cosmetics (AREA)
EP97921349A 1996-04-22 1997-04-22 Natürliche antoxidantien Withdrawn EP0897264A4 (de)

Applications Claiming Priority (5)

Application Number Priority Date Filing Date Title
US1620896P 1996-04-22 1996-04-22
US16208P 1996-04-22
US82120197A 1997-03-20 1997-03-20
US821201 1997-03-20
PCT/US1997/006821 WO1997039632A1 (en) 1996-04-22 1997-04-22 Natural antioxidant composition

Publications (2)

Publication Number Publication Date
EP0897264A1 true EP0897264A1 (de) 1999-02-24
EP0897264A4 EP0897264A4 (de) 1999-09-08

Family

ID=26688312

Family Applications (1)

Application Number Title Priority Date Filing Date
EP97921349A Withdrawn EP0897264A4 (de) 1996-04-22 1997-04-22 Natürliche antoxidantien

Country Status (3)

Country Link
EP (1) EP0897264A4 (de)
AU (1) AU2741197A (de)
WO (1) WO1997039632A1 (de)

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