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WO2000039248A1 - Procede de protection d'une substance susceptible de se deteriorer par oxydation - Google Patents

Procede de protection d'une substance susceptible de se deteriorer par oxydation Download PDF

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Publication number
WO2000039248A1
WO2000039248A1 PCT/IL1999/000693 IL9900693W WO0039248A1 WO 2000039248 A1 WO2000039248 A1 WO 2000039248A1 IL 9900693 W IL9900693 W IL 9900693W WO 0039248 A1 WO0039248 A1 WO 0039248A1
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WO
WIPO (PCT)
Prior art keywords
substance
antioxidant
compositions
food
acid
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.)
Ceased
Application number
PCT/IL1999/000693
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English (en)
Inventor
Rena Reznik
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.)
RAD Natural Technologies Ltd
Original Assignee
RAD Natural Technologies Ltd
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
Priority claimed from IL12772498A external-priority patent/IL127724A0/xx
Priority claimed from IL12859399A external-priority patent/IL128593A0/xx
Application filed by RAD Natural Technologies Ltd filed Critical RAD Natural Technologies Ltd
Priority to EP99959658A priority Critical patent/EP1246884A1/fr
Priority to AU16787/00A priority patent/AU1678700A/en
Priority to CA2432441A priority patent/CA2432441C/fr
Publication of WO2000039248A1 publication Critical patent/WO2000039248A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729—Organic compounds; Microorganisms; Enzymes
    • A23B2/733—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
    • A23B2/742—Organic compounds containing oxygen
    • A23B2/754—Organic compounds containing oxygen containing carboxyl groups
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23B—PRESERVATION OF FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES; CHEMICAL RIPENING OF FRUIT OR VEGETABLES
    • A23B2/00—Preservation of foods or foodstuffs, in general
    • A23B2/70—Preservation of foods or foodstuffs, in general by treatment with chemicals
    • A23B2/725—Preservation of foods or foodstuffs, in general by treatment with chemicals in the form of liquids or solids
    • A23B2/729—Organic compounds; Microorganisms; Enzymes
    • A23B2/742—Organic compounds containing oxygen
    • A23B2/754—Organic compounds containing oxygen containing carboxyl groups
    • A23B2/758—Carboxylic acid esters
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/105—Aliphatic or alicyclic compounds
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K30/00—Processes specially adapted for preservation of materials in order to produce animal feeding-stuffs
    • 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
    • A61K8/37—Esters of carboxylic acids
    • A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • 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
    • C11B5/0035—Phenols; Their halogenated and aminated derivates, their salts, their esters with carboxylic acids
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A40/00—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production
    • Y02A40/90—Adaptation technologies in agriculture, forestry, livestock or agroalimentary production in food processing or handling, e.g. food conservation

Definitions

  • the present invention relates to protecting a substance liable to oxidative deterioration and to materials which are so protected
  • antioxidant material is isolated from rosemary by extraction with a non-polar solvent, removal of the solvent and steam distillation, giving an aqueous dispersion, which was filtered, antioxidant being obtained from the solid material by further processing including extraction with aqueous alkali at pH at least 10 5
  • An isolated antioxidant is 7 ⁇ , 11 , 12-t ⁇ hydroxy-6, 10-(epoxymethano)ab ⁇ eta- 8,11 ,13-t ⁇ en-20-one
  • US 4,877,635 (Todd) describes a process for producing an oil-soluble extract of a Labiatae herb claimed to contain essentially all of the antioxidant substances in the herb, in the course of which acetone- or methyl ethyl ketone-insolubles, defined as pro-oxidant substances, are, so far as practicable, removed by precipitation US 5,023,017 (Todd) relates to a stable Labiatae antioxidant solution, having a pH 84-11 8, prepared from an initial solvent extract of the herb, and claimed to contain (besides ⁇ 75% water, and an edible alcohol and/or polyol) essentially all of the antioxidant substances in the herb, which is preferably rosemary, sage or thyme
  • rosmarinic acid is valuable in view of its antnnflammatory properties, see e g US 4,329,361 (Zenk et al )
  • rosmarinic acid is also known for its use in skin-treatment or cosmetic compositions, see e g JP 63162611 , JP 9067251 and US 5,393,526 (Castro)
  • rosmarinic acid is claimed to be useful in a composition for protection against erythema and inflammatory reactions caused by exposure to UV rays, and to have antioxidant, antibacterial and antifungal activity, see FR 2652001 (cf JP 06145034)
  • the action of rosmarinic acid as a 5-l ⁇ poxygenase inhibitor is also featured in JP 1121217, where, extracted from pe ⁇ lla species, it is used as a constituent of an antiallergic food
  • a still further object of the invention is to provide a process protection for a substance liable to oxidative deterioration by inclusion of water-soluble antioxidant material prepared by permitting maximum recovery of the industrially useful components from plants of the Labiatae family, such components including essential oils, completely water-soluble antioxidant material and known components which are both water-insoluble and organic solvent soluble, such as vitamin E and carnosic acid
  • the present invention accordingly provides in one aspect a substance liable to oxidative deterioration, which is characterized by the fact that it incorporates as antioxidant for that substance, at least one compound selected from sub-groups ( ⁇ ), ( ⁇ ) and ( ⁇ ), namely ( ⁇ ) rosmarinic acid,
  • the invention provides use of at least one compound selected from sub-groups ( ⁇ ), ( ⁇ ) and ( ⁇ ), namely ( ⁇ ) rosmarinic acid, ( ⁇ ) salts of the carboxylic acid function in rosmarinic acid, ( ⁇ ) esters and amides of the carboxylic acid function in rosmarinic acid, in admixture with a substance liable to oxidative deterioration, in at least a minimum amount necessary to confer antioxidative protection on said substance, provided that when said substance is a dermato-cosmetic composition, said at least one compound is used in an amount less than 0 1 % of the admixture, and that said at least one compound excludes mixtures in a form as extracted from natural sources and comprising any compound in sub-groups ( ⁇ ), ( ⁇ and ( ⁇ ), together with any other ant ⁇ ox ⁇ dant(s)
  • the invention provides a method for treating a substance liable to oxidative deterioration, in order to confer antioxidative protection on said substance, which comprises admixing said substance with at least one compound selected from sub-groups ( ⁇ ), ( ⁇ ) and ( ⁇ ), namely ( ⁇ ) rosmarinic acid, ( ⁇ ) salts of the carboxylic acid function in rosmarinic acid, ( ⁇ ) esters and amides of the carboxylic acid function in rosmarinic acid, in at least a minimum amount necessary to confer said protection on said substance, provided that when said substance is a dermato-cosmetic composition, said at least one compound is used in an amount less than 0 1 % of the admixture, and that said at least one compound excludes mixtures in a form as extracted from natural sources and comprising any compound in sub-groups ( ⁇ ), ( ⁇ and ( ⁇ ), together with any other ant ⁇ ox ⁇ dant(s)
  • the proviso as to the dermato-cosmetic composition excludes the disclosure of FR 2,652,
  • FIG. 1 illustrates chromatographic fractionation of antioxidant material from rosemary, having utility in accordance with an embodiment of the invention
  • FIG. 2 illustrates chromatographic fractionation of antioxidant material from oregano, having utility in accordance with an embodiment of the invention
  • antioxidant in a form selected from completely water-soluble materials containing a major proportion of non-antioxidant diluent, and which are solid at ambient temperatures, and aqueous solutions thereof,
  • said antioxidant comprises at least one of
  • a sodium rosma ⁇ nate preferably isolated from tissue of plants of the Labiatae family, most preferably by use of an aqueous extractant
  • the substance incorporating antioxidant according to the invention is selected from sub-groups (I), (II) and (III), namely
  • compositions (I) pharmaceutical compositions, cosmetic compositions, animal feedstuff compositions and food compositions adapted for human consumption,
  • compositions selected from pharmaceutical compositions, cosmetic compositions, animal feedstuff compositions and food compositions adapted for human consumption,
  • compositions selected from pharmaceutical compositions, cosmetic compositions, animal feedstuff compositions and food compositions adapted for human consumption, which composition comprises an ingredient liable to oxidative deterioration
  • Such food composition may be e g , selected from sugar-based confectionery, manufactured cereals, fruit or vegetable products, beverages or beverage concentrates, ground meat products and vegetable analogues thereof
  • Such food composition may comprise at least one additional ingredient selected from the water-soluble vitamins thiamine, ⁇ boflavin, niacin, py ⁇ doxine, pantothenic acid, biotin, fo c acid, cobalamin and ascorbic acid, the oil-soluble vitamins retinol, calciferol, tocopherol and menadione, in combined form the elements sodium, potassium, calcium, phosphorus, magnesium, chlorine, sulfur, iron, copper, iodine, manganese, cobalt, zinc molybdenum, fluorine, selenium and chromium, unsaturated fatty acids which are known to metabolized in the body to prostaglandins, and physiologically compatible derivatives of said fatty acids, food colorants and pigments, acceptable dispersing and suspending agents, and
  • an amount of ant ⁇ ox ⁇ dant(s) effective to prevent oxidation of the ingredient liable to oxidative deterioration should be used Generally, from about 0 0001 to about 1 %, preferably from about 0 0005 to about 0 1% by weight of the food composition may be used, depending on the nature of the composition and the type of oxidative activity which is to be inhibited
  • Colorants or pigments, used in food compositions, which are liable to oxidative deterioration are for example, polyene pigments and colorants such as ⁇ -carotene
  • compositions which contain fats or oils comprising fatty acids or their esters, either saturated or unsaturated may be preserved using ant ⁇ ox ⁇ dant(s) according to the invention
  • fatty acids are well known and are listed in Noller, Textbook of Organic Chemistry, 2nd Ed pp 108-113 and 138-146 (1958), which is incorporated by reference herein
  • Typical but non-limiting examples of food compositions, including fats and oils adapted for use therein, are soybean oil, corn oil, cottonseed oil, olive oil, butter, margarine, salad creams and mayonnaises, dairy products, ice cream, frozen vegetables, soups, fried foods and
  • a particular aspect of the present invention resides in the use of rosmarinic acid and its derivatives as described herein, for the purpose of antioxidative protection of vitamins and their analogs and functional derivatives of the vitamins and the analogs
  • the water-soluble vitamins thiamine, ⁇ boflavin, niacin, py ⁇ doxine, pantothenic acid, biotin, fo c acid, cobalamin and ascorbic acid the oil-soluble vitamins retinol, calciferol, tocopherol and menadione, and their analogs and functional derivatives thereof, especially such analogs and derivatives having analogous biological activity
  • vitamins which are themselves known to be antioxidants in particular ascorbic acid (including its salts and esters) and ⁇ -tocopherol (including its esters) can themselves be protected from deterioration by use of rosmarinic acid and its derivatives
  • the substance liable to oxidative deterioration, the oxidation which is inhibited in accordance with the present invention includes the essential oils, such as those derived, for example, from citrus fruit and flowers
  • the antioxidants utilized in accordance with the invention are selected from rosmarinic acid, salts of the carboxylic acid function in rosmarinic acid, and esters and amides of the carboxylic acid function in rosmarinic acid Rosmarinic acid may be isolated from natural sources e g as described in certain of the above-mentioned published documents, or it (and indeed its salts, esters and amides) may be chemically synthesized It may also be made by enzymatic or cell culture procedures, see e g US 5,011 ,775 (Rao) and published documents mentioned therein, the contents of this patent and of such documents, being incorporated herein by reference
  • Example 1 shows inter alia that the prior art practice of obtaining antioxidant material from Labiatae family plants, from organic solvent soluble extracts, while rejecting aq fractions, and/or rejecting acetone-insolubles, results in substantial loss of potentially valuable antioxidant Moreover, Example 1 (c) shows surprisingly, that contrary to Viani and Todd, useful completely water-soluble antioxidant material can be obtained by alkaline extraction
  • the method is based on the rate of oxidation of linoleic acid (LA) to its conjugated diene hydroperoxide (Pryor et al , in J Org Chem , 1993, 58 (13) 3521 -3532), and 2,2'-azob ⁇ s (2-am ⁇ d ⁇ nopropane) 2HCI (ABAP) is used to provide a constant rate of radical production
  • LA linoleic acid
  • ABAP 2,2'-azob ⁇ s (2-am ⁇ d ⁇ nopropane) 2HCI
  • a 1 % LA aq emulsion was prepared with 1 % Tween 20 and 0 05M sodium phosphate buffer (pH 7 4)
  • a control sample contained 0 025 ml of the LA emulsion + 2 87 ml of the buffer + 0 1 ml 0 05M ABAP
  • a test sample contained 0 05 ml of the LA emulsion + 2 7-2 8
  • a column of 8cm x 1cm is packed with MacroPrep-methyl (hydrophobic interaction 40 ⁇ m, Bio-Rad) was washed exhaustively with water and ethanol, and then used for purification of the water extract lyophilizate (see Example 1(f), above) 200 mg of the lyophilizate was dissolved in 1 ml water, and the solution was loaded on the MacroPrep column that had been pre-equilibrated with water Elution was carried out using a 0 1 % acetic acid/ 70 30 ethanol in water gradient starting with a 100 0 ratio at 0 minutes and ending with a 0 100 ratio at 220 minutes, and at a flow rate of 2 0 ml/minute Peaks are monitored by UV absorption at 280nm The column effluent was collected after 85 minutes (193 ml) and the active material was found to be eluted between 85 to 100 minutes (36 ml, 30-40%o ethanol (balance water))
  • a concentrate was first prepared containing 40% lecithin, 40% oil (e g soybean oil), 20% propylene glycol and 4% based on the foregoing mixture of 65% ( ⁇ 2 6% pure) sodium rosmannate Rosmarinic acid can alternatively be substituted for the sodium salt
  • the thus-prepared concentrate can then be used in a bulk oil which it is desired to protect against oxidative deterioration
  • oil is soybean oil
  • test results at 60°C were as follows Antioxidant Concentration Days until oxidation
  • Vitamin E 0 06% 4

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  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
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  • Food Science & Technology (AREA)
  • Wood Science & Technology (AREA)
  • Veterinary Medicine (AREA)
  • Emergency Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Animal Behavior & Ethology (AREA)
  • Animal Husbandry (AREA)
  • Organic Chemistry (AREA)
  • Dermatology (AREA)
  • Birds (AREA)
  • Epidemiology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Materials Engineering (AREA)
  • Food Preservation Except Freezing, Refrigeration, And Drying (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Cosmetics (AREA)

Abstract

On assure une protection antioxydation d'une substance susceptible de se détériorer par oxydation, en mélangeant cette dernière avec au moins un composé choisi dans les sous-groupes (α), (β) et (η) : (α) correspondant à de l'acide rosmarinique, (β) à des sels de la fonction acide carboxylique de l'acide rosmarinique, (η) correspondant à des esters et amides de la fonction acide carboxylique de l'acide rosmarinique, et ce, dans certaines conditions.
PCT/IL1999/000693 1998-12-24 1999-12-22 Procede de protection d'une substance susceptible de se deteriorer par oxydation Ceased WO2000039248A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
EP99959658A EP1246884A1 (fr) 1998-12-24 1999-12-22 Procede de protection d'une substance susceptible de se deteriorer par oxydation
AU16787/00A AU1678700A (en) 1998-12-24 1999-12-22 Method for protecting a substance liable to oxidative deterioration
CA2432441A CA2432441C (fr) 1999-12-22 1999-12-22 Procede de protection d'une substance susceptible de se deteriorer par oxydation

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
IL12772498A IL127724A0 (en) 1998-12-24 1998-12-24 Method for protecting a substance liable to oxidative deterioration
IL127724 1998-12-24
IL12859399A IL128593A0 (en) 1999-02-18 1999-02-18 Method for protecting a substance susceptible to oxidative deterioration
IL128593 1999-02-18

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WO2000039248A1 true WO2000039248A1 (fr) 2000-07-06

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1314435A1 (fr) * 2001-11-27 2003-05-28 Rahn Ag Préparation d'agents actifs pour usage cosmétique et/ou dermatologique
WO2009013757A1 (fr) * 2007-07-26 2009-01-29 Frutarom Ltd. Composition protégeant les huiles et les graisses
WO2015095545A1 (fr) * 2013-12-20 2015-06-25 Abbott Laboratories Composition nutritionnelle contenant de l'huile oxydable et de l'acide rosmarinique
WO2016057818A1 (fr) * 2014-10-08 2016-04-14 Abbott Laboratories Compositions nutritionnelles comprenant un composant oxydable et un extrait végétal soluble dans l'eau
EP3425033A4 (fr) * 2016-03-02 2019-10-23 Fuji Oil Holdings Inc. Composition de graisse ou d'huile présentant des propriétés anti-oxydation
US11957135B2 (en) 2016-03-02 2024-04-16 Fuji Oil Holdings Inc. Chocolate-like food containing polyunsaturated fatty acid

Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012531A (en) * 1973-10-26 1977-03-15 Societe D'assistance Technique Pour Produits Nestle S.A. Process for extracting antioxydants
US4329361A (en) * 1979-12-22 1982-05-11 Nattermann & Cie Gmbh Use of rosmarinic acid in the treatment of inflammations and pharmaceutical products used therein
US4354035A (en) * 1980-03-15 1982-10-12 A. Nattermann & Cie Gmbh Process for isolating rosmarinic acid from plants
US4358442A (en) * 1979-12-22 1982-11-09 Nattermann & Cie Gmbh Rosmarinic acid-phospholipide-complex
JPS63162611A (ja) * 1986-12-24 1988-07-06 Pola Chem Ind Inc 美肌化粧料
JPH01121217A (ja) * 1987-11-05 1989-05-12 Advance Co Ltd ５−リポキシゲナーゼ作用阻害剤
FR2652001A1 (fr) * 1989-09-20 1991-03-22 Andary Claude Composition dermato-cosmetique a base d'acide rosmarinique presentant des proprietes de filtre solaire et d'agent anti-inflammatoire.
US5023017A (en) * 1989-08-21 1991-06-11 Kalamazoo Holdings, Inc. Stable alkaline labiatae antioxidant extracts
US5393526A (en) * 1994-02-07 1995-02-28 Elizabeth Arden Company, Division Of Conopco, Inc. Cosmetic compositions
WO1997014319A1 (fr) * 1995-10-20 1997-04-24 Hauser Chemical Research, Inc. Aliments et boissons contenant des anthocyanines stabilisees par des extraits vegetaux
WO1998058656A1 (fr) * 1997-06-23 1998-12-30 Hauser, Inc. Compositions aromatisees aux agrumes, stables en conservation, renfermant des extraits de plantes

Patent Citations (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4012531A (en) * 1973-10-26 1977-03-15 Societe D'assistance Technique Pour Produits Nestle S.A. Process for extracting antioxydants
US4329361A (en) * 1979-12-22 1982-05-11 Nattermann & Cie Gmbh Use of rosmarinic acid in the treatment of inflammations and pharmaceutical products used therein
US4358442A (en) * 1979-12-22 1982-11-09 Nattermann & Cie Gmbh Rosmarinic acid-phospholipide-complex
US4354035A (en) * 1980-03-15 1982-10-12 A. Nattermann & Cie Gmbh Process for isolating rosmarinic acid from plants
JPS63162611A (ja) * 1986-12-24 1988-07-06 Pola Chem Ind Inc 美肌化粧料
JPH01121217A (ja) * 1987-11-05 1989-05-12 Advance Co Ltd ５−リポキシゲナーゼ作用阻害剤
US5023017A (en) * 1989-08-21 1991-06-11 Kalamazoo Holdings, Inc. Stable alkaline labiatae antioxidant extracts
FR2652001A1 (fr) * 1989-09-20 1991-03-22 Andary Claude Composition dermato-cosmetique a base d'acide rosmarinique presentant des proprietes de filtre solaire et d'agent anti-inflammatoire.
US5393526A (en) * 1994-02-07 1995-02-28 Elizabeth Arden Company, Division Of Conopco, Inc. Cosmetic compositions
WO1997014319A1 (fr) * 1995-10-20 1997-04-24 Hauser Chemical Research, Inc. Aliments et boissons contenant des anthocyanines stabilisees par des extraits vegetaux
WO1998058656A1 (fr) * 1997-06-23 1998-12-30 Hauser, Inc. Compositions aromatisees aux agrumes, stables en conservation, renfermant des extraits de plantes

Non-Patent Citations (5)

* Cited by examiner, † Cited by third party
Title
CHEN J H ET AL: "ANTIOXIDANT ACTIVITIES OF CAFFEIC ACID AND ITS RELATED HYDROXYCINNAMIC ACID COMPOUNDS", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,US,AMERICAN CHEMICAL SOCIETY. WASHINGTON, vol. 45, no. 7, 1 July 1997 (1997-07-01), pages 2374 - 2378, XP000656898, ISSN: 0021-8561 *
FRANKEL E N ET AL: "ANTIOXIDANT ACTIVITY OF A ROSEMARY EXTRACT AND ITS CONSTITUENTS, CARNOSIC ACID, CARNOSOL, AND ROSMARINIC ACID, IN BULK OIL AND OIL-IN-WATER EMULSION", JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,US,AMERICAN CHEMICAL SOCIETY. WASHINGTON, vol. 44, no. 1, 1 January 1996 (1996-01-01), pages 131 - 135, XP000546463, ISSN: 0021-8561 *
NOLLER: "Textbook of Organic Chemistry", 1958, pages: 108 - 113
PATENT ABSTRACTS OF JAPAN vol. 012, no. 438 (C - 544) 17 November 1988 (1988-11-17) *
PATENT ABSTRACTS OF JAPAN vol. 013, no. 362 (C - 625) 14 August 1989 (1989-08-14) *

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1314435A1 (fr) * 2001-11-27 2003-05-28 Rahn Ag Préparation d'agents actifs pour usage cosmétique et/ou dermatologique
WO2009013757A1 (fr) * 2007-07-26 2009-01-29 Frutarom Ltd. Composition protégeant les huiles et les graisses
WO2015095545A1 (fr) * 2013-12-20 2015-06-25 Abbott Laboratories Composition nutritionnelle contenant de l'huile oxydable et de l'acide rosmarinique
WO2016057818A1 (fr) * 2014-10-08 2016-04-14 Abbott Laboratories Compositions nutritionnelles comprenant un composant oxydable et un extrait végétal soluble dans l'eau
CN107105743A (zh) * 2014-10-08 2017-08-29 雅培制药有限公司 包含可氧化组分和水溶性植物提取物的营养组合物
JP2017531429A (ja) * 2014-10-08 2017-10-26 アボット・ラボラトリーズＡｂｂｏｔｔ Ｌａｂｏｒａｔｏｒｉｅｓ 被酸化性成分および水溶性植物抽出物を含む栄養組成物
EP3425033A4 (fr) * 2016-03-02 2019-10-23 Fuji Oil Holdings Inc. Composition de graisse ou d'huile présentant des propriétés anti-oxydation
US11957135B2 (en) 2016-03-02 2024-04-16 Fuji Oil Holdings Inc. Chocolate-like food containing polyunsaturated fatty acid

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