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WO1994022322A1 - Antioxydants solides microcristallins a base de catechines de the vert, pour lipides - Google Patents

Antioxydants solides microcristallins a base de catechines de the vert, pour lipides Download PDF

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Publication number
WO1994022322A1
WO1994022322A1 PCT/US1994/003505 US9403505W WO9422322A1 WO 1994022322 A1 WO1994022322 A1 WO 1994022322A1 US 9403505 W US9403505 W US 9403505W WO 9422322 A1 WO9422322 A1 WO 9422322A1
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Prior art keywords
particles
catechin
less
largest dimension
solid
Prior art date
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Ceased
Application number
PCT/US1994/003505
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English (en)
Inventor
Paul H. Todd, Jr.
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Kalamazoo Holdings Inc
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Kalamazoo Holdings Inc
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Filing date
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Publication of WO1994022322A1 publication Critical patent/WO1994022322A1/fr
Anticipated expiration legal-status Critical
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Classifications

    • 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
    • C11B5/0085—Substances of natural origin of unknown constitution, f.i. plant extracts
    • 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
    • A23B2/70—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

Definitions

  • Green tea catechins as antioxidants, especially for fats, oils, foods, and ingredients of foods, in the form of less than 38 micron particles, and suspensions thereof in lipid media in which they are insoluble.
  • FIG. 1 portrays the structures of the four significant catechins contained in and extractable from green tea.
  • Oxidation of fats, vegetable oils, carotenoids and their biologically active derivatives, Vitamin A, and of essential oils and other flavorings results in degradation of their quality, and is deleterious to foodstuffs contain ⁇ ing the oxidized products.
  • the art shows many methods of inhibiting lipid oxida ⁇ tion by adding fat-soluble antioxidants to the substrate.
  • the art does not show the stabilization of fats, oils, fatty foods and ingredients of foods employing green tea catechins in a form effective for such purpose.
  • Green tea is known to contain significant amounts of four catechins. Their structures are shown in FIG. 1. In the preparation of black or fermented teas, these catechins are partially or totally oxidized as shown by Sanderson, USP 3,812,266. The oxidized catechins are much less effective antioxidants, so that green tea is the preferred source of catechins for the product of this invention. Hara, in USP 4,840,966, describes the therapeutic use of catechins to reduce blood pressure. They are admin ⁇ istered orally in the form of tablets or incorporated into the diet. Other health benefits of green tea catechins are known.
  • Catechins are very soluble in water, and many patents have issued pertaining to methods of extracting them to make instant tea. Examples of such patents include Mish- kin, USP 3,451,823. He describes a method of first ex- tracting the tea with hot water, which will recover the catechins, and then reextracting with highly superheated water under pressure, to degrade and solubilize other tea materials, which may also have antioxidant properties. These undefined substances, of unknown toxicology, are not included in the preferred form of this invention.
  • the separation of caffeine which is also present in the aqueous and organic extracts, can be achieved by conventional methods as described in the Hara patent, employing chloroform, leaving the catechins in the water phase and the caffeine in the organic phase. Hara then recovers the catechins from the water using ethyl acetate, without any adjustment of pH, and this solvent is then removed to give a powder.
  • the caffeine may be removed from the tea leaves by supercritical carbon dioxide extraction, as is done in the preparation of decaffeinated tea leaves.
  • the separation of caffeine from the catechins is not necessary or even preferred in this invention, since it does not interfere with the antioxidant activity of the catechins in the lipid.
  • the elimination of the use of chloroform is an object of this invention. Hara, in USP 4,613,672, describes an elegant method of preparation of purified individual catechins for use in pharmaceutical preparations. These products can be used as aqueous solutions, or as dried powders. He also shows that ethanolic solutions of these powders, when added to lipids, act as antioxidants.
  • a further object is to provide the foregoing wherein the lipid medium is an edible medium.
  • Another object of the invention is the provision of such products embodying a non-ionic surface-active agent.
  • An additional object is the provision of synergistic combinations of such tea catechin particles or suspension and a natural or synthetic antioxidant. Additional objects of the invention will become apparent hereinafter, and still other objects will be obvious to one skilled in the art to which this invention pertains.
  • Water-soluble and fat-insoluble polyphenolic antioxi ⁇ dants (catechins), recovered from green tea and reduced to a particle size less than 38 microns on their largest dimension, are effective antioxidants in lipid media such as fats, oils, foods, and ingredients of foods without imparting undesirable flavors, aromas, and precipitates, preferably in the form of suspensions or dispersions in a lipid medium in which they are insoluble. Since it is known that tea polyphenols have positive effects on human health, the resulting stabilized lipids can be considered to have nutritional qualities superior to the same lipid stabilized with common synthetic antioxidants. Synergistic effects with other natural antioxidants and with phosphates are also disclosed.
  • the present invention provides a form of solid tea catechins which is completely dispersible in oil.
  • Critical to this invention is that the particles be less than 38 microns in size on their largest dimension. It provides maximum utilization of the antioxidant properties of the catechins, even at ambient temperatures, which cannot be achieved using the powdered tea extracts of the present art in the stabilization of lipids.
  • the preferred form of this invention utilizes the water-soluble and fat-insoluble constituents of the tea extract as a lipid antioxidant, and preferably discards the fat-soluble portion of the tea extract.
  • the fat-soluble portion may be present, with or without chlorophyll.
  • the products of this invention are effective in stabilizing foods containing lipids, such as pie crusts, snacks, dressings, meats, pastries, and similar foods, as well as food ingredients such as breadings, flavorings, and colorings.
  • My invention then comprises, inter alia, the follow- ing, individually or in combination:
  • a solid green tea catechin which is less than 38 microns in size on its largest dimension, preferably less than 10 microns on its largest dimension, such a catechin suspended in an oleogenous medium in which it is insoluble, such a product wherein the medium is an edible medium, and any such catechin or product in combination with a tocoph- erol, a Labiatae extract, or solid ascorbic acid or phos ⁇ phate particles of less than 38 micron size on their largest dimension, or a non-ionic surface active agent.
  • a fat, oil, fatty food or food ingredient substrate stabilized against oxidation with any such catechin, product, or composition such a stabilized substrate wherein the substrate includes a carotenoid
  • a method of stabilizing a fat, oil, food, or food ingredient substrate which includes the step of combining the substrate with any such catechin, product, or composi ⁇ tion as set forth in the foregoing, and such a method wherein the substrate includes a carotenoid.
  • a method of preparing solid tea catechin particles of less than 38 micron particle size on their largest dimension or suspensions thereof in a lipid medium in which they are insoluble which consists essentially of the steps of a. extracting green tea with a substantially anhy- drous lower alkanol, b. admixing the extract with water, c. removing alcohol from the aqueous extract, d.
  • a water-immiscible solvent selected from the group consisting of lower-alkyl ketones, lower alka- nols, and lower alkyl esters of lower-aliphatic acids, and adding a water-soluble salt, and adjusting the pH of the aqueous phase to a pH between 1 and 6, these latter two steps being conducted simultaneously or in either order, e. removing the water-immiscible solvent - catechin solution from the aqueous phase and recovering the solid catechin particles therefrom, and f. reducing the size of the solid catechin particles 5 to less than 38 micron on their largest dimension, such a method wherein the lower-alkanol employed in step a.
  • step f is essentially anhydrous methanol, such a method wherein the water-immiscible solvent employed in step d. is ethyl acetate, such a 10 method wherein step b. or c. is carried out in the presence of a hydrocarbon solvent and includes the further step of removing the hydrocarbon solvent and the lipids dissolved therein from the aqueous catechin solution, such a 15 method wherein the solid catechin particles from step f.
  • lipid medium in which they are insoluble
  • the lipid medium is an edible medium
  • the lipid medium comprises a non-ionic surface-active agent
  • the surface-active agent is selected from lecithin, glycerol mono-oleate, liquid mono- and di- glycerides, acylated mono- and di-glycerides, benzyl 25 alcohol, triacetin, caproic-caprylic acid polyglycerides, and polysorbate.
  • An art accepted method of measuring the antioxidant activity of a substance employs the RancimatTM to ascertain the induction time of a given lipid using a given dose of
  • the antioxidant generally with 18 liters of air per hour blowing through the fat held at a constant temperature
  • the Rancimat measures conductivity of an aqueous solution which captures the volatile oxidation products formed as the fat oxidizes.
  • the results are reported as the ratio of the induction time of the test sample to the control, the higher the ratio, the more stable the fat.
  • the results correlate very well with other standard measures of rancidity development, such as the active oxygen method, organoleptic evaluations, and so forth.
  • RM rosemary extract especially HerbaloxTM product of Kalsec, Inc., Kalamazoo, Michigan
  • Labiatae Extract The solvent extract of a Labiatae herb, and preferably rosemary, sage, or thyme, especially rosemary.
  • the preferable form is that described in Todd
  • RancimatTM An instrument which measures the induction time of an oleogenous substrate, usually at 120 degrees Celsius and at 18 liters of air per hour. This is an accepted methodology for determining relative strengths of preparations of antioxidants. The effectiveness is ex ⁇ pressed as the induction time of the sample divided by the induction time of the control, as a percent.
  • this specifi- cation represents a nonionic surface-active agent, especially one taken from the class consisting of: a. mono and di glycerides of fatty acids, b. polyglyceride esters of fatty acids, c. mono and diglyceride esters further esterified with a dibasic organic acid taken from the class consisting of citric, lactic, and tartaric acids, d. acylated mono and diglyceride esters further esterified with a dibasic organic acid taken from the class consisting of citric, lactic, and tartaric acids, e. sorbitan esters of fatty acids, f.
  • Example 1 Preparation of the preferred form of green tea extract to be used in the lipid antioxidant preparations.
  • the solvent layer is removed, the aqueous layer again partitioned against the hydrocarbon solvent to remove traces of lipids, and again separated.
  • the pH of the water layer is then adjusted to an acidic pH between 1 and 6, preferably 2.5 to 4.5, and optimally 3 to 4, and a water-soluble salt, preferably a non-toxic salt such as sodium or potassium chloride, sodium citrate, or sodium sulfate, added to a concentration of at least 0.2%, optimally between 5% and 30%, W/W of the water to salt out the catechins.
  • a water-soluble salt preferably a non-toxic salt such as sodium or potassium chloride, sodium citrate, or sodium sulfate
  • the catechins are then extracted from the water phase using ethyl acetate or other water-immiscible solvent preferably selected from lower alkanols, lower alkyl ketones, and lower-alkyl lower- aliphatic acid esters.
  • ethyl acetate or other water-immiscible solvent preferably selected from lower alkanols, lower alkyl ketones, and lower-alkyl lower- aliphatic acid esters.
  • the ethyl acetate or other water-immiscible solvent solution is used as such, or desolventized to make a powder. These in turn are used to make the lipid antioxidant preparations of this invention. Steps (c) and (d) are essential only when all tea lipids are to be eliminated.
  • This preferred process differs from the prior art in requiring a substantially anhydrous lower alkanol, e.g., less than about 7% to 9% water being present in the alco ⁇ holic solvent, and most preferably less than 5%; the elimination of chloroform by the use of a hydrocarbon solvent, and criticality in adjusting the pH of the aqueous solution prior to ethyl acetate or other water-immiscible solvent extraction to between 1 and 6, and preferably 3 to 4, in the presence of a water-soluble salt for salting the catechins out of the aqueous phase. It goes without saying that the salt addition and pH adjustment can be carried out simultaneously or in either order.
  • Ethyl acetate can be replaced by other solvents which are immiscible with the aqueous phase, preferably selected from lower alkanols, lower-alkyl ketones, and lower-alkyl esters of lower-aliphatic acids, such as methyl ethyl ketone, acetone, butanol, and other lower aliphatic acid esters of lower alcohols such as isopropanol, e.g., isopro- pyl acetate, and the like.
  • solvents which are immiscible with the aqueous phase preferably selected from lower alkanols, lower-alkyl ketones, and lower-alkyl esters of lower-aliphatic acids, such as methyl ethyl ketone, acetone, butanol, and other lower aliphatic acid esters of lower alcohols such as isopropanol, e.g., isopro- pyl acetate, and the like.
  • Example 2 Preparation of less than 38 micron sized tea catechin solids in a medium in which they are insoluble.
  • Example 3 Preparation of less than 38 micron sized tea catechin solids from a solution of catechins. 150 ml of an ethyl acetate solution containing 25 g catechins was added to 150 g of soy oil, and desolventized. The desolventized product, containing lumps of catechins and liquid soy oil, was placed in a pebble mill and ground to less than 38 microns in size on the largest dimension of the catechin particles. It had the physical appearance of the product of Example 1.
  • Preparation Preparation of a suspension or dispersion of less than 38 micron sized phosphate particles in a medium in which they are insoluble.
  • Potassium salts of the phosphates can be substituted for the sodium salts if sodium reduction is an objective.
  • the above products are representative food-grade phosphates of less than 38 micron particle size on their largest dimension which are effective antioxidants in fats, oils, fatty foods, and ingredients of foods, especially when employed in the form of a suspension in an edible oleogenous medium such as the vegetable oil employed in the foregoing (a).
  • Example 4 Use of the Product of Example 1 in lard.
  • Example 5 Synergistic mixtures of the ⁇ 38 micron cate ⁇ chins with other natural antioxidants.
  • the synergism of the ⁇ 38 micron size catechins with ascorbic acid is demonstrated by admixing known amounts of each, and their combination, with the lard.
  • the synergism is expressed as the % increase in induction time over the induction time increase if the antioxidants are used by themselves. The results are shown in Table II. TABLE II. Synergism between catechins and ascorbic acid.
  • Example 6 The effectiveness of the ⁇ 38 micron catechins in vegetable oils.
  • rancid aromas As in the case of animal fats, including marine oils, the development of rancid aromas is inhibited by the ⁇ 38 micron tea catechins, even when they are added at ambient or lower temperatures and the fat refrigerated.
  • Example 7 Mixtures of ⁇ 38 micron sized catechins with non-ionic surface-active agents.
  • Example 1 The generally-preferred method of preparation of the catechins is shown in Example 1, and their size reduction in Example 2.
  • a lipid-soluble, non-ionic surface-active agent in the preparation. This can be done before or after grinding.
  • Suitable surface-active agents are lecithin, mono- and di-glycerides, acylated mono- and diglycerides, caproic- caprylic acid polyglycerides, and tartaric acid esters of mono- and diglycerides, as well as polysorbates.
  • the above list is not limiting, but rather preferred.
  • the teachings of this invention are particularly useful in stabilizing extruded animal foods and snacks, in which a fat is applied to the surface.
  • the enhancement of synergism by the employment of a non-ionic surface-active agent is useful in such applications, as well as in doughs such as frozen pie crusts. It is clear from the foregoing that the microcrysta ⁇ lline catechins of this invention improve the stability of lipids in broad classes of foods, including snacks, nuts, dressings, breadings, and meats, as well as flavorings such as essential oils and colorings such as those containing oxidizable carotenoids.
  • Example 8 Stabilization of a carotenoid and food ingredi ⁇ ent and food.
  • a 10% W/W suspension of tea catechins prepared accord- ing to Example 1 was mixed with oleoresin paprika at the level of 1.5% to provide 0.1% W/W of tea catechins in the oleoresin.
  • the oleoresin without catechins, and the oleoresin to which they had been added, were plated on dextrose and the dispersions then placed in an oven main- tained at 65° C.
  • the oleoresin without catechins lost one- third of its color in 28 hours, whereas that containing the catechins took 72 hours to lose the same amount of its carotenoid color.
  • oleoresin paprika contains alpha and beta carotene, lutein, zeaxanthin, capsanthin, and other carotenoids such as apo-carotenals in minor amounts. Therefore the invention will stabilize oxygenated carotenoids as well as hydrocarbons such as beta-carotene.
  • a dispersion of oleoresin paprika is a common food ingredient, being used in meats, baked goods, breadings, snacks, dressings, and the like, making it desirable to stabilize the color in order to have uniformity of color in the food. Because of the ability of the catechins to inhibit the development of rancidity in fats and oils, it is particularly desirable to utilize the thus-stabilized carotenoids in an oil medium, for the purpose of introduc- ing the stabilizing effect of the catechins into the food.
  • the present application discloses the prepara ⁇ tion of a novel form of solid tea catechins, which are unexpectedly powerful antioxidants in fats and oils in which they are insoluble. Critical to this effectiveness is the reduction of particle size to less than 38 microns. Synergism when used in combination with other antioxidants has been shown. Further, enhancement of the synergism by the incorporation of non-ionic surface-active agents in the catechin suspension is demonstrated. Other general and specific utility of the products and method of the present invention will be apparent to those practicing the art of food stabilization.
  • the present invention provides a novel and advantageous form of solid antioxidant tea catechin particles of less than 38 microns on their largest dimension and antioxidant suspensions or dispersions thereof in an oleogenous or lipidic medium in which they are insoluble, such products having increased antioxidant activity in fats, oils, carotenoids, and fatty foods and food ingredients, especially such materials and products as are exposed to oxidative stress, as well as a method of stabilizing such materials and products against oxidative discoloration, including foods, feeds, and foodstuffs which may encounter oxidative stress stabilized with a product or composition of the invention, and a method of stabilizing a food, feed, foodstuff, flavoring, or coloring with such a more effective form of catechin antioxidant product or composition of the invention.
  • the stabilization of carot ⁇ enoid pigments may thus advantageously be carried out. Synergistic effects are obtained by the incorporation of a natural antioxidant in or with such products or composi ⁇ tions, methods, and stabilized products, and the antioxi ⁇ dant effectiveness of the catechin antioxidant, antioxidant compositions, and methods of the invention is further enhanced by inclusion of a natural Labiatae antioxidant, less than 38 micron ascorbic acid or phosphate particles, a tocopherol, or even a synthetic antioxidant such as BHT or BHA therein or therewith, and the antioxidant power and stabilization effectiveness of a composition of the inven ⁇ tion may be even further improved by inclusion of a non- ionic surface-active agent therein or therewith. All of the foregoing provide long-awaited solutions to previously- existing oxidation and instability problems not adequately solved by the prior art.

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Abstract

L'invention se rapporte à des antioxydants polyphénoliques (catéchines) solubles dans l'eau et insolubles dans les graisses, extraits du thé vert et réduits en particules dont la plus grande dimension est inférieure à 38 microns, ces antioxydants ayant une action antioxydante efficace sur les milieux lipides tels que les graisses, les huiles, les aliments et les ingrédients alimentaires, sans créer d'odeurs, d'arômes et de précipités indésirables, ces antioxydants se présentant de préférence sous la forme de suspensions ou de dispersions dans un milieu lipide dans lequel ils sont insolubles. Comme on sait que les polyphénols du thé ont des effets positifs sur la santé, les lipides stabilisés qui en résultent peuvent être considérés comme possédant des qualités nutritives supérieures à un même lipide stabilisé avec des antioxydants synthétiques habituels. Des effets synergiques avec d'autres antioxydants naturels et avec des phosphates sont également décrits.
PCT/US1994/003505 1993-04-01 1994-03-31 Antioxydants solides microcristallins a base de catechines de the vert, pour lipides Ceased WO1994022322A1 (fr)

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Application Number Priority Date Filing Date Title
US4045693A 1993-04-01 1993-04-01
US08/040,456 1993-04-01

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WO1994022322A1 true WO1994022322A1 (fr) 1994-10-13

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032947A1 (fr) * 1996-03-05 1997-09-12 Comiter Trading & Services S.R.L. Produit a base d'huile d'olive, enrichi et complete par des antioxydants
US5888574A (en) * 1996-03-07 1999-03-30 Nestec Sa., Process to improve color stability of fruits and vegetables containing carotenoids
WO1999018814A1 (fr) * 1997-10-14 1999-04-22 Quest International B.V. Preparation permettant d'accroitre le statut antioxydant de cellules
WO2001032040A1 (fr) * 1999-11-01 2001-05-10 University Of Massachusetts Technique d'apport selectif dans des lipides membranaires d'antioxydants solubles dans la fraction lipidique polaire d'un produit alimentaire
US6254898B1 (en) * 2000-05-25 2001-07-03 Protective Factors, Inc. Nutraceutical composition for protection against solar radiation
US6375992B1 (en) 2000-02-23 2002-04-23 The Procter & Gamble Co. Methods of hydrating mammalian skin comprising oral administration of a defined composition
US7364763B1 (en) 1999-11-01 2008-04-29 University Of Massachusetts Method for selective delivery of lipid-soluble antioxidants into the polar lipid fraction of a food product
WO2009044240A1 (fr) * 2007-10-04 2009-04-09 Vitiva D.D. Protection antioxydante et anti-microbiologique de matières grasses et aliments contenant des matières grasses avec un mélange d'extraits de labiatae et de thé vert
FR2933850A1 (fr) * 2008-07-17 2010-01-22 Polaris Nouvelles compositions anti-oxydantes et les huiles ainsi additionnees
WO2010033034A1 (fr) * 2008-09-19 2010-03-25 Epax As Composition antioxydante pour huiles marines comprenant du tocophérol, de l'extrait de romarin, de l'acide ascorbique et de l'extrait de thé vert
WO2011025382A1 (fr) * 2009-08-26 2011-03-03 Epax As Composition d'anti-oxydant
FR3016168A1 (fr) * 2014-01-07 2015-07-10 Oleos Composition grasse stable comprenant des antioxydants, son procede de preparation et ses utilisations
CN107164088A (zh) * 2017-05-18 2017-09-15 西北农林科技大学 一种牡丹籽油复合天然抗氧化剂

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4515804A (en) * 1982-02-24 1985-05-07 Zyma Sa Crystal modifications of (+)-catechin and pharmaceutical preparations containing them
US4613672A (en) * 1983-07-05 1986-09-23 Mitsu Norin Co., Ltd. Process for the production of tea catechins
US4673530A (en) * 1983-05-30 1987-06-16 Mitsui Norin Co., Ltd. Process for the production of a natural antioxidant obtained from tea leaves

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4515804A (en) * 1982-02-24 1985-05-07 Zyma Sa Crystal modifications of (+)-catechin and pharmaceutical preparations containing them
US4673530A (en) * 1983-05-30 1987-06-16 Mitsui Norin Co., Ltd. Process for the production of a natural antioxidant obtained from tea leaves
US4613672A (en) * 1983-07-05 1986-09-23 Mitsu Norin Co., Ltd. Process for the production of tea catechins

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1997032947A1 (fr) * 1996-03-05 1997-09-12 Comiter Trading & Services S.R.L. Produit a base d'huile d'olive, enrichi et complete par des antioxydants
US5888574A (en) * 1996-03-07 1999-03-30 Nestec Sa., Process to improve color stability of fruits and vegetables containing carotenoids
WO1999018814A1 (fr) * 1997-10-14 1999-04-22 Quest International B.V. Preparation permettant d'accroitre le statut antioxydant de cellules
US7364763B1 (en) 1999-11-01 2008-04-29 University Of Massachusetts Method for selective delivery of lipid-soluble antioxidants into the polar lipid fraction of a food product
WO2001032040A1 (fr) * 1999-11-01 2001-05-10 University Of Massachusetts Technique d'apport selectif dans des lipides membranaires d'antioxydants solubles dans la fraction lipidique polaire d'un produit alimentaire
US6375992B1 (en) 2000-02-23 2002-04-23 The Procter & Gamble Co. Methods of hydrating mammalian skin comprising oral administration of a defined composition
US6254898B1 (en) * 2000-05-25 2001-07-03 Protective Factors, Inc. Nutraceutical composition for protection against solar radiation
WO2009044240A1 (fr) * 2007-10-04 2009-04-09 Vitiva D.D. Protection antioxydante et anti-microbiologique de matières grasses et aliments contenant des matières grasses avec un mélange d'extraits de labiatae et de thé vert
FR2933850A1 (fr) * 2008-07-17 2010-01-22 Polaris Nouvelles compositions anti-oxydantes et les huiles ainsi additionnees
WO2010033034A1 (fr) * 2008-09-19 2010-03-25 Epax As Composition antioxydante pour huiles marines comprenant du tocophérol, de l'extrait de romarin, de l'acide ascorbique et de l'extrait de thé vert
US9301536B2 (en) 2008-09-19 2016-04-05 Epax Norway As Antioxidant composition for marine oils comprising tocopherol, rosemary extract, ascorbic acid and green tea extract
WO2011025382A1 (fr) * 2009-08-26 2011-03-03 Epax As Composition d'anti-oxydant
FR3016168A1 (fr) * 2014-01-07 2015-07-10 Oleos Composition grasse stable comprenant des antioxydants, son procede de preparation et ses utilisations
CN107164088A (zh) * 2017-05-18 2017-09-15 西北农林科技大学 一种牡丹籽油复合天然抗氧化剂
CN107164088B (zh) * 2017-05-18 2021-10-12 西北农林科技大学 一种牡丹籽油复合天然抗氧化剂

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