WO2005012470A1 - Antioxidative composition - Google Patents

Antioxidative composition Download PDF

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Publication number
WO2005012470A1
WO2005012470A1 PCT/JP2004/011405 JP2004011405W WO2005012470A1 WO 2005012470 A1 WO2005012470 A1 WO 2005012470A1 JP 2004011405 W JP2004011405 W JP 2004011405W WO 2005012470 A1 WO2005012470 A1 WO 2005012470A1
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WIPO (PCT)
Prior art keywords
extract
oil
animal
soluble
group
Prior art date
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PCT/JP2004/011405
Other languages
French (fr)
Japanese (ja)
Inventor
Tadahiro Hiramoto
Kenji Saiki
Eiichi Hirose
Osamu Fukaya
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Takasago International Corporation
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Priority to JP2005512609A priority Critical patent/JP4583309B2/en
Publication of WO2005012470A1 publication Critical patent/WO2005012470A1/en

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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22Organic compounds
    • C11D7/26Organic compounds containing oxygen
    • C11D7/267Heterocyclic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23DEDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00Other edible oils or fats, e.g. shortenings, cooking oils
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, 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
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/46Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09KMATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/34Anti-oxidant compositions; Compositions inhibiting chemical change containing plant or animal materials of unknown composition
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11BPRODUCING, 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
    • C11B5/00Preserving by using additives, e.g. anti-oxidants
    • C11B5/0092Mixtures
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005Other compounding ingredients characterised by their effect
    • C11D3/0084Antioxidants; Free-radical scavengers
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22Organic compounds
    • C11D7/24Hydrocarbons
    • C11D7/248Terpenes
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D7/00Compositions of detergents based essentially on non-surface-active compounds
    • C11D7/22Organic compounds
    • C11D7/40Products in which the composition is not well defined
    • C11D7/44Vegetable products

Definitions

  • the present invention relates to antioxidant compositions.
  • antioxidants have been developed and reported to address this.
  • BHT butylated hydroxytoluene
  • BHA butylhydroxydisole
  • ascorbic acid and tocopherol are widely used as having excellent antioxidant ability.
  • BHT Synthetic antioxidants such as BHA are effective in terms of efficacy, but these compounds are considered to be carcinogenic based on the results of animal tests, and are used in foods. , The amount added, the type of food to be added, etc. are strictly restricted. Therefore, natural antioxidants having excellent effects have been demanded in view of safety and palatability.
  • tocopherol is widely used in various fields, including food, because it is safe and has an excellent antioxidant effect against oxidative deterioration of oil.
  • tocopherol has a peculiar odor and a bad taste. When an effective amount is contained, the oxidative deterioration of the oil is suppressed, but the bad odor and the bad taste are conspicuous, seriously deteriorating the value of foods and the like. there were.
  • Ascorbic acid is extremely difficult to dissolve in fat-soluble substances, so it is difficult to use it as an antioxidant for fat-soluble substances.
  • an ascorbyl ester derivative such as stearic acid or ascorbyl palmitate.
  • the antioxidant effect is inferior to that of tocopherol, and that the use of a high concentration may accelerate the deterioration of animal and vegetable oils. Therefore, there has been a demand for a safe antioxidant composition capable of suppressing the addition amount of a conventionally known natural antioxidant such as tocopherol while maintaining the same or higher antioxidant power as tocopherol.
  • antioxidants that combine tocopherol with other components include amino acids such as ascorbic acid, phospholipids, L-lysine, L-histidine, L-tributophane, and L-methionine; citrate, malic acid, and succinic acid.
  • amino acids such as ascorbic acid, phospholipids, L-lysine, L-histidine, L-tributophane, and L-methionine
  • citrate malic acid
  • succinic acid succinic acid
  • perilla essential oil is included as a food having pharmacological effects and physiological functions, and is not expected to function as an antioxidant. Rather, it merely combines an antioxidant such as tocopherol as an essential component to prevent oxidation of perilla essential oil, which is easily oxidized.
  • potato-derived extracts have not been reported to function as an antioxidant, and conversely have a function to prevent the deterioration of food flavors that could not be achieved with conventionally known antioxidants.
  • Japanese Patent Application Laid-Open No. 2000-27 was reported only (Japanese Patent Application Laid-Open No. 2000-27).
  • An object of the present invention is to provide a safe antioxidant which has an antioxidant power equal to or higher than that of tocopherol, and which has reduced odor and odor derived from the antioxidant.
  • the present inventors have conducted repeated studies to obtain a component that is superior in antioxidant capacity and that is naturally present, and as a result, extracted a potato extract, which is a component derived from potato, with an oil-soluble solvent.
  • the oil-soluble fraction of the banana extract and the grape skin extract extracted by the oil-soluble solvent are extracted with the oil-soluble fraction of the grape skin extract and the grape seed extract.
  • An oil-soluble fraction of a grape seed extract extracted with an oil-soluble solvent, an oil-soluble fraction of a burdock extract extracted from a Gopo extract with the oil-soluble solvent, an oil-soluble fraction of a marjoram extract extracted from the marjoram extract with the oil-soluble solvent A fraction or an oil-soluble fraction of a sunflower seed extract obtained by extracting the sunflower seed extract with the oil-soluble solvent, and at least one selected from the group consisting of tocopherol, ascorbate, jS-carotene, and lycopene. It has been found that the antioxidant ability of the combination of the above is higher than that of the above-described various oil extracts of the extract alone or the conventionally known antioxidant alone such as tocopherol.
  • the present inventors have further studied based on this finding. For example, when tocopherol is used as a component to be combined with the oil extract of various extracts, by suppressing the amount of tocopherol added, the unpleasant and unpleasant odor peculiar to tocopherol is reduced. And found that the use of the above-described extract oil-soluble fraction can reduce the effective amount compared to the case of tocopherol alone, and that the amount of tocopherol added can be further reduced. We have completed the present invention.
  • Satsumaimo extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
  • oil-soluble solvents selected from the group consisting of lower alcohols, polyol-based organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Extract oil-soluble fraction;
  • a perilla extract having a perilla essential oil content of 1% by weight or less is selected from the group consisting of lower alcohols, polyol-based organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils.
  • Banana extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
  • Grape seed extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Grape seed extract oil fraction;
  • the gopo extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils.
  • Bow extract oil-soluble fraction selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils.
  • Bow extract oil-soluble fraction selected from the group consisting of lower alcohols, polyol organic solvents, benz
  • the marjoram extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Marjoram extract oil fraction; and
  • oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Extract oil-soluble fraction;
  • One or more oil extract fractions selected from the group consisting of:
  • An antioxidant composition comprising:
  • the antioxidant composition comprises:
  • Potato extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Potato extract oil fraction;
  • Satsumaimo extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
  • a perilla extract having a perilla essential oil content of 1% by weight or less is selected from the group consisting of lower alcohols, polyol-based organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils.
  • Perilla extract oil-soluble fraction extracted with one or more selected oil-soluble solvents; Apple extract extracted with at least one oil-soluble solvent selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Oil-soluble fraction;
  • the banana extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils.
  • oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils.
  • the grape seed extract is treated with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Grape seed extract oil-soluble fraction extracted;
  • Gopo extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Burdock extract oil-soluble fraction;
  • Marjoram extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction; and
  • Castor seed extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Castor seed extract oil soluble fraction;
  • One or more oil extract fractions selected from the group consisting of: (b) at least one selected from the group consisting of tocopherol, ascorbate, jS-carotene, and lycopene
  • the antioxidant composition comprises:
  • Potato extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Potato extract oil fraction;
  • Satsumaimo extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
  • perilla extract containing less than 1% by weight of perilla essential oil from the group consisting of lower alcohol, polyol organic solvent, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride and animal and vegetable oils
  • perilla extract oil-soluble fraction extracted with one or more selected oil-soluble solvents;
  • the apple extract is extracted with at least one oil-soluble solvent selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
  • Oil extract of banana extract selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils.
  • the grape skin extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Grape skin extract oil-soluble fraction;
  • Grape seed extract lower alcohol, polyol organic solvent, benzyl alcohol Grape seed extract oil-soluble fraction extracted with at least one oil-soluble solvent selected from the group consisting of coal, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride and animal and vegetable oils;
  • Marjoram extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction; and
  • oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Extract oil-soluble fraction;
  • One or more oil extract fractions selected from the group consisting of:
  • the ratio of component (a) to component (b) in the antioxidant composition is preferably 1: 9 to 9: 1 by weight.
  • an animal or vegetable oil characterized by containing the antioxidant composition, wherein the content of the antioxidant composition is 0.01% by weight to 10% by weight based on the total amount of the animal or vegetable oil. %, and the animal and vegetable oil is not particularly limited, but is preferably lacquer oil, almond oil, cocoa oil, hazelnut oil, macadamia nut oil, rapeseed oil or fish oil.
  • a food or drink a medicine, or a fragrance comprising the above-mentioned animal or vegetable oil.
  • Cosmetics and household goods are provided.
  • the present invention provides a method for imparting antioxidant ability to animal and vegetable oils by adding the above antioxidant composition to animal and vegetable oils.
  • the present invention it is suitable for practical use by using at least one selected from tocophere, ascorbic acid ester,] 3-carotene, and lycopene together with various extract oil-soluble fractions.
  • the antioxidant ability of the conventionally known antioxidant alone such as tocopherol and the antioxidant ability of the natural product extracted oil fraction are synergistically enhanced.
  • the amount of the conventional antioxidant for example, tocopherol can be reduced in order to obtain an antioxidant power equal to or higher than that of tocopherol, so that the unpleasant odor and odor peculiar to tocopherol can be reduced.
  • the effective amount of the antioxidant composition itself can be lower than when using tocopherol alone, so that the amount of tocopherol added can be further reduced.
  • FIG. 1 is a flow chart showing an example of the production process of oil-soluble fractions of various extracts used as component (a) of the present invention.
  • Oil extract of the apple extract obtained by extracting the apple extract with the above-mentioned oil-soluble solvent, oil-soluble fraction of the banana extract obtained by extracting the banana extract with the above-mentioned oil-soluble solvent, and grape peel extract The grape peel extract oil-soluble fraction extracted with the predetermined oil-soluble solvent, the grape seed extract oil-soluble fraction extracted from the grape seed extract with the predetermined oil-soluble solvent, The oil-soluble fraction of Gopo extract extracted with the oil-soluble solvent, the oil-soluble fraction of marjoram extract obtained by extracting the marjoram extract with the predetermined oil-soluble solvent, and the sunflower seed extract were extracted with the predetermined oil-soluble solvent.
  • One or more oil extract fractions selected from the group consisting of oil fractions of castor seed extract; and (b) selected from the group consisting of tocopherol, ascorbate,) 3-carotene, and lycopene Contains one or more.
  • antioxidant refers to a substance having a property of preventing the action of oxygen on an autoxidizable substance.
  • the function of preventing autoxidation (the effect of oxygen) (antioxidant capacity) can be classified in various ways.
  • a radical inhibitor that suppresses the chain reaction of autoxidation
  • a metal inactivator that inactivates the pro-oxidant action of metals such as iron and copper
  • non-radical decomposition of peroxide (4) It has no antioxidant effect by itself, but can be divided into four groups: a synergist that enhances its effect in cooperation with a radical inhibitor.
  • the “antioxidant composition” in the present invention refers to a composition that prevents autoxidation of a substance that autoxidizes by various functions as described above.
  • the oil-soluble fractions of various extracts used as the component (a) of the present invention can be obtained by further extracting extracts obtained from various plant raw materials with an oil-soluble solvent.
  • various extracts are obtained, for example, by drying a plant material and cutting it into an appropriate size, immersing the extract in a solvent under a certain condition, filtering and removing the plant material from the solvent, concentrating the extract, and further purifying the extract. Can be obtained.
  • FIG. 1 shows an example of the production process of the oil-soluble fractions of various extracts used as the component (a) of the present invention.
  • the steps indicated by the dotted lines indicate steps that can be arbitrarily performed.
  • the plant raw materials (1) include potato, sweet potato, coffee beans, perilla, apple, banana, grape peel, grape seed, burdock, marjoram, Castor seeds can be used.
  • the raw material is potato or sweet potato
  • tubers, rhizomes, stems and leaves can be used.
  • raw or roasted coffee beans can be used without particular limitation. Any type of bean can be used, but green soybeans are particularly preferred.
  • perilla leaves and stems can be used.
  • a plant of the genus Perilla can be used without any particular limitation.
  • Perilla frutescens Britton var.acuta Kudo Perilla forma discolor Makino, J-year-old Nsso (Perilla forma viridis Majdno), Cilimennso (Perilla frutescens Britton var. Japonica Hara) I can do it.
  • the raw material is apple or banana
  • use the fruit including the peel If the raw material is apple or banana, use the fruit including the peel. Alternatively, only the peel can be used.
  • any kind of grape peel can be used, but each kind of red grape is particularly preferred.
  • grape seeds of any variety can be used.
  • burdock is used as the raw material, use the rhizome.
  • the raw material is sunflower seeds
  • sunflower seeds belonging to the family Asteraceae or the genus Himagri use sunflower seeds belonging to the family Asteraceae or the genus Himagri.
  • various extracts (3) are obtained using the crushed material (2).
  • Extraction of various extracts (3) is carried out by solvent extraction (A) using water, lower alcohol, hydrated lower alcohol and the like.
  • lower alcohol refers to an alcohol having 1 to 4 carbon atoms, that is, methanol, ethanol, propanol, and butanol, and particularly, methanol, ethanol, and the like.
  • Hydrophilic lower alcohol means a mixture of water and lower alcohol.
  • the extraction operation is not particularly limited, and varies depending on the plant and the solvent used.In general, the crushed material is immersed in the solvent at a temperature of 4 ° C to 100 ° C or extracted by gentle stirring. Do by things.
  • the extraction operation can be performed efficiently.
  • the time required for extraction is usually about 30 minutes to 12 hours. Note that a multi-stage extraction method known before the present application may be adopted.
  • the extract (3) obtained above may be further subjected to a chromatographic treatment (D) to concentrate the active ingredient (6).
  • D chromatographic treatment
  • the above extract is poured into a chromatographic column prepared and prepared in advance, and then an eluate composed of a solvent is poured, and what is temporarily retained in the column is washed away with the solvent, and the solvent that flows out May be adopted by a known method.
  • the carrier used for the column is not particularly limited, but examples thereof include synthetic adsorbents such as silica gel, Diaion HP20 (Mitsubishi Kasei), Amberlite XAD-2 (Rohm & Haas), and Hitachi Gel # 3010 (Hitachi Chemical).
  • the elution is usually performed at room temperature, but may be performed at a low temperature.
  • the solvent flowing out by the above method is fractionated by a known means to obtain a fraction.
  • Each fraction or a combination of a plurality of fractions may be used as an extract after further distilling off the solvent under reduced pressure.
  • an extract obtained by subjecting the extract to any treatment for example, a concentrate obtained by further removing a solvent from the extract, a so-called extract ⁇ ⁇
  • An extract obtained by further removing a specific compound from the extract may be used as the extract.
  • the solvent used for extracting various extracts from the crushed steam distillation residue is water, lower alcohol,
  • the solvent is preferably one or more solvents selected from water lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils.
  • “monodaliceride” is a fatty acid ester of glycerol esterified with one molecule of a fatty acid, and examples of the fatty acid include bromobronic acid, palmitic acid, and stearic acid.
  • the “diglyceride” is a fatty acid ester of glycerol esterified with two molecules of fatty acid, and examples of the fatty acid include cabronic acid, palmitic acid, and stearic acid.
  • “animal or vegetable oil” refers to an oil containing triglyceride as a main component, and any oil can be used without any particular limitation as long as it is liquid at normal temperature.
  • the perilla extract obtained from perilla has a perilla essential oil content of 1% or less and is substantially free of perilla essential oil. That is, in the present invention, the content of perilla essential oil in the perilla extract is 1% by weight or less, preferably 0.1% by weight or less, and more preferably 0.01% by weight or less. In the present specification, the content of perilla essential oil is measured by gas chromatography. As used herein, the term “perilla essential oil” refers to a complex of volatile aroma components contained in perilla.
  • the essential oil contains berylaldehyde as the main component, and also contains 1-limonene, rioliophylene, -fuarnesene, perilla, linalool, and peryl alcohol.
  • the essential oil derived from perilla contains no berylaldehyde and contains 1-piperitone and naginata ketone as main components. Commercial products may be used for any of the extracts.
  • the oil-soluble fractions of various extracts used as the component (a) are obtained by extracting the extract obtained as described above with a lower alcohol, a polyol organic solvent, benzyl alcohol, ethyl acetate, petroleum ether. , Glycerol, monoglyceride, diglyceride and animal and vegetable oils by performing solvent extraction-filtration (B) with at least one oil-soluble solvent selected from the group consisting of:
  • the extraction operation is not particularly limited, and varies depending on the plant material and the solvent used to obtain the extract, but usually, lower alcohols (eg, methanol, ethanol, etc.) Phenol, organic solvents such as ethyl alcohol, ethyl alcohol, propylene glycol), benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils (for example, One or more oil-soluble solvents selected from the group consisting of soybean oil, corn oil, rapeseed oil, and lard), preferably benzyl alcohol, and the extract at 20 ° C to 80 ° C, preferably 40 ° C.
  • lower alcohols eg, methanol, ethanol, etc.
  • Phenol organic solvents
  • benzyl alcohol ethyl acetate
  • petroleum ether ethyl alcohol
  • glycerol benzyl alcohol
  • monoglycerides
  • Extraction is performed by immersion or gentle stirring at a temperature of ° C to 80 ° C.
  • the time required for the extraction is usually about 10 minutes to 12 hours, preferably 30 minutes to 3 hours. Note that a multi-stage extraction method known before the present application may be employed. After extraction and filtration, the filtrate (4) is used as the extract oil-soluble fraction.
  • the raw material contains essentially no essential oil, or the one from which the essential oil has been removed by steam distillation or the like, the raw material is directly used as a lower alcohol, a polyol organic solvent, benzyl alcohol, or acetic acid.
  • the oil-soluble fraction may be adjusted by extraction with one or more oil-soluble solvents selected from the group consisting of ethyl, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils. This is not enough in terms of efficiency.
  • the oxidized botanical composition of the present invention comprises various extract oil-soluble fractions obtained by the above method, that is, a potato extract oil-soluble fraction, a sweet potato extract oil-soluble fraction, and an oil extract-oil.
  • Oil fraction Perilla extract oil fraction, Apple extract oil fraction, Banana extract oil fraction, Grape peel extract oil fraction, Grape seed extract oil fraction, Burdock extract oil
  • a component comprising at least one extract oil-soluble fraction selected from the group consisting of a soluble fraction, an oil-soluble fraction of marjoram extract, and an oil-soluble fraction of sunflower seed extract; And at least one member selected from the group consisting of tocopherol, ascorbate, i3-carotene, and lycopene.
  • the antioxidant composition of the present invention reduces the off-flavor and odor derived from the antioxidant while maintaining the same or higher antioxidant ability as tocopherol by using the components (a) and (b) in combination. This is an excellent effect.
  • the oil extract of potato extract is preferably at least one extract oil-soluble fraction selected from the group consisting of an extract oil-soluble fraction, a marjoram extract oil-soluble fraction, and a sunflower seed extract oil-soluble fraction.
  • extract oil-soluble fractions are particularly excellent in antioxidant effect, and are easy to handle with almost no problems such as material odor and coloring.
  • coffee extract oil-soluble for 11 minutes has a raw material odor and its color is black, so it may be difficult to handle.
  • tocopherol, ascorbic acid ester, ⁇ -carotene, and lycopene, tocopherol or ascorbic acid ester may be used alone or in combination with tocopheric acid and ascorbic acid ester. I like it.
  • tocopherol exhibits a safe and excellent antioxidant effect
  • ascorbic acid ester is oil-soluble, so that it is easy to use for oil-soluble components such as lipids.
  • tocopherol and ascorbic acid are used in combination, a higher antioxidant effect can be obtained than when these components are used alone.
  • the combined use of tocopherol and ascorbic acid can further reduce the amount of tocopherol added.
  • the tocopherol one or more of ⁇ -tocopherol,) 3-tocopherol, ⁇ -tocopherol, -tocopherol and the like can be used without limitation.
  • the ratio of the component (a) to the component (b) is preferably 1: 9 to 9: 1 by weight, more preferably 2: 8 to 7: 3. It is more preferably 3: 7 to 5: 5.
  • antioxidant composition of the present invention may further contain, if necessary, other deoxidizing agents in addition to the components (a) and (b).
  • extracts include, for example, extracts of rosemary sage, basil, and green tea.
  • the antioxidant composition of the present invention can be added to and blended with animal and vegetable oils that are easily oxidized to prevent oxidation of the animal and vegetable oils.
  • animal and vegetable oils include soybean oil, corn oil, safflower oil, cottonseed oil, laccase oil (peanut oil), almond oil, cocoa oil, hazelnut oil, macadamia nut oil, rapeseed oil (canola oil), lard, head, r %
  • fish oil such as sardine oil, liver oil and the like can be mentioned, but not limited thereto.
  • laccase oil, almond oil, cocoa oil, methanol nut oil, macadamia nut oil and fish oil can be mentioned.
  • the amount of the antioxidant composition contained in the animal and vegetable oils of the present invention varies depending on the purpose and is not particularly limited, but is usually 0.01% by weight to 1% by weight based on the total amount of the animal and vegetable oils. If the content is 0% by weight, the object is achieved. Preferably, it is 0.05% to 3% by weight.
  • the animal and vegetable oils of the present invention may contain, in addition to the antioxidant composition, thickening agents such as anhydrous silicates, anhydrous sulfates, various inorganic chlorides, saccharides, polysaccharides, etc., surfactants, stabilizers, and benzoic acid.
  • thickening agents such as anhydrous silicates, anhydrous sulfates, various inorganic chlorides, saccharides, polysaccharides, etc., surfactants, stabilizers, and benzoic acid.
  • An antibacterial agent such as sodium benzoate, a dye, a fragrance, or a known antioxidant such as BHT, BHA, vitamin C, or the like may be coexisted in advance.
  • Animal and vegetable oils containing the antioxidant composition of the present invention include various foods and beverages; fragrance products, basic cosmetics, hair cosmetics, bath cosmetics and other cosmetics; toiletries, detergents, finishing agents, aromatic deodorants, etc. Supplies: Any of those that use animal and vegetable oils, such as pharmaceuticals, can be used.
  • Examples of the above foods and drinks include confectionery products such as chocolate, gum, candy, potato chips, cookies, and biscuits; beverages such as lactic acid beverages and powdered beverages; ice creams, cherries, ice confectionery, mousse, frozen yogurt Frozen desserts; desserts such as pudding, jelly, bavarois, yogurt, cream; cooked foods such as soups, curries, stews; seasonings such as noodle soup, dressings, mayonnaise; And other daily products such as butter cream and margarine; fish paste products.
  • confectionery products such as chocolate, gum, candy, potato chips, cookies, and biscuits
  • beverages such as lactic acid beverages and powdered beverages
  • desserts such as pudding, jelly, bavarois, yogurt, cream
  • cooked foods such as soups, curries, stews
  • seasonings such as noodle soup, dressings, mayonnaise
  • And other daily products such as butter cream and margarine; fish paste products.
  • Examples of the above-mentioned Frederance products include perfume, eau de toilette, eau de cologne, and escologone.
  • the above basic cosmetics include skin creams, cleansing creams, night creams, hand creams, emulsions, lotions, after-shave lotions, body-lotions, foundations, lipsticks, lip balms, talcum powders, anti-aging cosmetics, anti-aging products Cosmetics, sun care products, massage oils, etc. can be mentioned.
  • hair cosmetics include shampoos, rinses, conditioners, rinse-in shampoos, treatments, and other hair-washing agents; pomades, hair tonics, hair liquids, hair styling agents such as hair, hair creams, hair creams; Agents; cold wave agents and the like.
  • bath agent examples include a powder bath agent, a solid bath agent, a solid foaming bath agent, bath oil, a bubble bath, and the like.
  • toiletry products examples include toilet stones, bath stones, and transparent stones.
  • detergent examples include powder detergent for clothing, liquid detergent for clothing, fabric softener, kitchen detergent, toilet detergent, bathroom detergent, glass cleaner, mold remover and the like.
  • aromatic deodorant examples include a gel aromatic deodorant, a liquid aromatic deodorant, an impregnated aerosol aromatic deodorant, and a mist type aromatic deodorant.
  • Examples of the pharmaceuticals include salves, ointments, suppositories, tablets, liquid medicines, capsule-type medicines, and granular medicines.
  • Sample 1 oil extract of perilla extract
  • the green coffee beans were pulverized with a pulverizer (mesh 5 mm), added with water, and extracted with 85-95 for 2 hours. After the extract was filtered, the filtrate was concentrated to dryness to obtain a coffee extract.
  • Gopo was pulverized with a mill, and ethanol was added thereto for 2 hours of reflux extraction. Lottery After the filtrate was filtered, the filtrate was concentrated to dryness to obtain a burdock extract.
  • Tocopherol (manufactured by Nacalai Tesque, Inc.) (1 g) was added with benzyl alcohol and dissolved to 100 g to give a tocopher solution.
  • Antioxidant compositions (Examples 1 to 35 and Comparative Examples 1 to 20) were prepared by blending the obtained various samples, the tocopherol solution, and the ascorbic acid ester solution according to the blending ratio (wZw) shown in Table 1.
  • wZw blending ratio
  • a stabilization test was performed by autoxidation under the following conditions, and the results are shown in Table 1 in comparison with the case of tocopherol alone. Stabilization test by autoxidation
  • Test method Volatility generated by oxidation according to the method (Rancimat method) according to “Oil Chemistry Vol. 42, No. 6 (1993), 2.4.28.2-93” Decomposition products were collected in water, and the stability was confirmed by measuring the time until the bending point where the conductivity changed abruptly.
  • Example 21 2 8 1.25 Hibiki father 8 Sannore 8 10: 0 0.68 ⁇ ⁇
  • Example 22 8: 2 1 ⁇ 21
  • Example 23 5: 5 1.45
  • Example 24 8 1.39 9 10: 0 0.73
  • Example 25 8: 2 1.51 Hook SI example 26
  • Volatile decomposition products (mostly formic acid) generated by the oxidative decomposition of fats and oils are collected in pure water, and the conductivity is plotted automatically. Time to point. It is considered that the longer the induction time, the more the oxidative deterioration of fats and oils is suppressed. From Table 1, the synergistic effect with tocopherol was observed in Examples 13 and 13 in which sample 1 and tocopherol were combined, Examples 4 and 6 in which sample 2 was combined with tocopherol, and combination of sample 3 and tocopherol. Example 7 9 Example 10 12 combining sample 4 and tocopherol
  • Example 5 with sample 5 combined with tocopherol 13 15 Example with sample 6 combined with tocopherol 16 18, Example with sample 7 combined with tocopherol 1 9 21, Example 8 with sample 8 combined with tocopherol Example 22-24, Example 25 27 combining sample 9 with tocopherol, Example 28 30 combining sample 10 with tocopherol, Example 3 1 33 combining sample 11 with tocopherol, It became clear that the oxidative degradation of laccase oil was suppressed more than in the case. In Comparative Example 12 15 in which Sample 12 and Tocopherol were combined, although a certain synergistic effect was observed, the effect was not sufficient compared to each combination of Sample 11 and Tocopherol.
  • an antioxidant composition was prepared by blending Sample 1 and the tocopherol solution according to the blending ratio (wZw) shown in Table 2, and this was added to 4 g of laccase oil in the amount shown in Table 2 to achieve oxidation stability.
  • the sex was examined.
  • the test method and measurement conditions are as in Test Example 1. Table 2 shows the results. Table 2
  • An antioxidant composition was prepared by mixing Sample 1 and the tocopherol solution according to the mixing ratio (wZw) shown in Table 3, and 1 g of each antioxidant composition was added to 4 g of each animal and vegetable oil. Was examined for its oxidative stability. The degree of deterioration was evaluated by a sensory test conducted by five expert panelists according to the score index. Table 3 shows the results. Score index)
  • vanilla flavor containing the antioxidant composition of the present invention was prepared according to the following formulation.
  • Canola oil (a type of rapeseed oil) _97. 75
  • vanilla flavor shown in Formulation Example 3 was kneaded into chocolate dough at 0.05 to 0.2% by weight to prepare chocolate.
  • the dried peanuts were ground using a food processor according to the amounts shown below, and then butter was added and mixed well. Thereto, maple syrup, oil extract of sweet potato extract and tocopherol were added and mixed well to prepare a peanut butter containing the antioxidant composition of the present invention.
  • maple syrup, oil extract of sweet potato extract and tocopherol were added and mixed well to prepare a peanut butter containing the antioxidant composition of the present invention.
  • Sand cream containing the antioxidant composition of the present invention was prepared according to the following formulation.
  • the antioxidant composition of the present invention includes, for example, animal and vegetable oils; various foods and beverages; cosmetics such as foods, basic cosmetics, hair cosmetics, bath preparations; household goods such as toiletry products, detergents and finishing agents, and aromatic deodorants. Used as a useful antioxidant for pharmaceuticals and the like.

Abstract

It is intended to provide an antioxidative agent which has an antioxidative effect comparable to tocopherol or even exceeding the same and yet shows reduced offensive taste or smell inherent to antioxidant agents. The above object can be achieved by providing an antioxidant composition containing: (a) at least one member selected from among fat-soluble fractions of various extracts including potato extract, sweet potato extract, coffee extract, Japanese basil oil extract containing not more than 1 % by weight of essential Japanese basil oil, apple extract, banana extract, grape peel extract, grape seed extract, burdock extract, marjoram extract and sunflower seed extract each prepared by extraction with a definite fat-soluble solvent; and (b) at least one member selected from among tocopherol, ascorbic acid esters, β-carotene and lycopene.

Description

明細書 抗酸化組成物 技術分野  Description Antioxidant composition Technical field
本発明は、 抗酸化組成物に関する。 背景技術  The present invention relates to antioxidant compositions. Background art
古くから油脂などの有機物が酸化や熱により変質され、 本来有する性質が劣化 したり、 あるいは失われてしまうことが知られていた。 その点を解決するため、 数多くの抗酸化剤が開発され、 報告されている。 例えば、 プチル化ヒドロキシト ルェン (B H T)、 プチルヒドロキシァ二ソール (B H A)、 ァスコルビン酸、 ト コフエロールなどが優れた抗酸化能を有するものとして広く使用されている。 し かしながら、 B H T、: B H Aといつた合成抗酸化剤は効果の点では有効であるが、 これら化合物は、 動物試験の結果から発ガン性が懸念されており、 食品に使用す る場合は、 添加量、 添加する食品の種類等が厳しく制限されている。 このため、 安全性、 嗜好性の面から、 優れた効果を有する天然抗酸化剤が要望されてきた。  It has been known for a long time that organic substances such as fats and oils are deteriorated by oxidation and heat, and their inherent properties are deteriorated or lost. A number of antioxidants have been developed and reported to address this. For example, butylated hydroxytoluene (BHT), butylhydroxydisole (BHA), ascorbic acid, and tocopherol are widely used as having excellent antioxidant ability. However, BHT: Synthetic antioxidants such as BHA are effective in terms of efficacy, but these compounds are considered to be carcinogenic based on the results of animal tests, and are used in foods. , The amount added, the type of food to be added, etc. are strictly restricted. Therefore, natural antioxidants having excellent effects have been demanded in view of safety and palatability.
しかしながら、 従来の天然抗酸化剤には、 それ由来の異味異臭があることが問 題とされてきた。 例えば、 トコフエロールは、 安全で且つオイルの酸化劣化に対 して優れた抗酸化効果を示すことから、 食品をはじめとして様々な分野で幅広く 利用されている。 しかしながら、 トコフエロールには特有の嫌臭と嫌味があり、 有効量を含有させると、 オイルの酸化劣化は抑制されるものの、 その嫌臭嫌味が 目立ち、 食品等の価値を大きく損ねるという重大な問題があった。  However, it has been a problem that conventional natural antioxidants have a peculiar off-flavor. For example, tocopherol is widely used in various fields, including food, because it is safe and has an excellent antioxidant effect against oxidative deterioration of oil. However, tocopherol has a peculiar odor and a bad taste. When an effective amount is contained, the oxidative deterioration of the oil is suppressed, but the bad odor and the bad taste are conspicuous, seriously deteriorating the value of foods and the like. there were.
ァスコルビン酸は脂溶性物質に極めて溶けにくいので、 脂溶性物質の酸化防止 剤として使用するには困難である。 ァスコルビン酸を脂溶性物質に溶解させるた めに、 例えば、 ステアリン酸、 パルミチン酸ァスコルビルのようなァスコルビル エステル誘導体を用いることが提案された。 しかしながら、 トコフエロールと比 ベて抗酸化効果が劣っているし、 高濃度で使用すると逆に動植物油の劣化を促進 する場合があることが知られている。 そこで、 トコフエロールと同等若しくはそれ以上の抗酸化力を維持しながら、 トコフエロール等の従来公知の天然抗酸化剤の添加量を抑えることができる安全 な抗酸化組成物の提供が求められてきた。 Ascorbic acid is extremely difficult to dissolve in fat-soluble substances, so it is difficult to use it as an antioxidant for fat-soluble substances. In order to dissolve ascorbic acid in a fat-soluble substance, it has been proposed to use an ascorbyl ester derivative such as stearic acid or ascorbyl palmitate. However, it is known that the antioxidant effect is inferior to that of tocopherol, and that the use of a high concentration may accelerate the deterioration of animal and vegetable oils. Therefore, there has been a demand for a safe antioxidant composition capable of suppressing the addition amount of a conventionally known natural antioxidant such as tocopherol while maintaining the same or higher antioxidant power as tocopherol.
トコフエロールとの組み合わせとしては、 ローズマリー抽出物が報告されてい る (特開平 4一 2 2 6 5 8 8号公報)。 しかし、 その効果は満足のいくものではな い。  As a combination with tocopherol, a rosemary extract has been reported (Japanese Patent Application Laid-Open No. Hei 412,688). However, the effect is not satisfactory.
トコフエロールと他の成分を組み合わせた抗酸化剤の例として、 ァスコルビン 酸、 リン脂質、 L—リジン、 L—ヒスチジン、 L—トリブトファン、 L一メチォ ニンなどのアミノ酸、 クェン酸、 リンゴ酸、 コハク酸などの有機酸との組み合わ せが報告されている (特許第 2 5 8 8 6 6 8号公報)。 しかしながら、 これらの組 合せでは、 効果の点で満足のいくものでないばかりか、 食品の風味に影響を与え ることからその使用が大きく限定されている。  Examples of antioxidants that combine tocopherol with other components include amino acids such as ascorbic acid, phospholipids, L-lysine, L-histidine, L-tributophane, and L-methionine; citrate, malic acid, and succinic acid. A combination with an organic acid has been reported (Japanese Patent No. 2588868). However, the use of these combinations is not only unsatisfactory in terms of effect, but also greatly limits their use because they affect the flavor of the food.
さらに、 トコフエロールと、 シソ由来の成分である精製シソ油 (シソ精油) と を組み合わせた油脂組成物が報告されている (特開平 8— 1 1 6 8 7 8号公報)。 しかしながら、 本公報では、 シソ精油は、 薬理効果、 生理機能のある食品として 含まれているのであって、 抗酸化剤としての機能は期待されていない。 むしろ、 酸化されやすいシソ精油の酸化を防止するために、 トコフエロール等の酸化防止 剤を必須の成分として組み合わせているにすぎない。  Furthermore, an oil / fat composition combining tocopherol and a refined perilla oil (perilla essential oil), which is a perilla-derived component, has been reported (Japanese Patent Application Laid-Open No. 8-116688). However, in this publication, perilla essential oil is included as a food having pharmacological effects and physiological functions, and is not expected to function as an antioxidant. Rather, it merely combines an antioxidant such as tocopherol as an essential component to prevent oxidation of perilla essential oil, which is easily oxidized.
また、 シソ由来のその他の成分として、 水溶性のクマリン類縁体が知られてい る。しかしながら、当該成分の抗酸化能について報告された文献はなく、むしろ、 従来公知の抗酸化剤である B H T、 ァスコルピン酸或いはトコフエロールが達成 し得なかった、 食品香料の劣化を防止する性質を有することが報告されるにとど まるものであった (特開 2 0 0 1 - 1 3 6 9 3 1号公報)。  Water-soluble coumarin analogs are also known as other components derived from perilla. However, no literature has been reported on the antioxidant capacity of the component, but rather it has the property of preventing the deterioration of food flavors, which could not be achieved by the conventionally known antioxidants BHT, ascorbic acid or tocopherol. Was reported only (Japanese Patent Application Laid-Open No. 2001-36931).
同様に、 ジャガイモ由来の抽出液についても、 抗酸化剤としての機能が報告さ れた例はなく、 逆に、 従来公知の抗酸化剤では達成し得なかった食品香料の劣化 防止機能があることが報告されるにとどまるものであった (特開 2 0 0 2 - 2 7 Similarly, potato-derived extracts have not been reported to function as an antioxidant, and conversely have a function to prevent the deterioration of food flavors that could not be achieved with conventionally known antioxidants. Was reported only (Japanese Patent Application Laid-Open No. 2000-27).
5 4 9 7号公報)。 発明の開示 本発明は、 トコフエロールと同等若しくはそれ以上の抗酸化力を備えながら、 抗酸化剤由来の嫌味嫌臭等が低減された安全な抗酸化剤を提供することを課題と する。 No. 497 publication). Disclosure of the invention An object of the present invention is to provide a safe antioxidant which has an antioxidant power equal to or higher than that of tocopherol, and which has reduced odor and odor derived from the antioxidant.
本発明者らは、 抗酸化能により優れた成分であって、 しかも天然に存在するも のを得るべく、 研究を重ねた結果、 ジャガイモ由来の成分であるジャガイモ抽出 物を油溶性溶媒によって抽出したジャガイモ抽出物油溶画分、 サツマィモ抽出物 を前記油溶性溶媒によって抽出したサッマイモ抽出物油溶画分、 コーヒー抽出物 を前記油溶性溶媒によって抽出したコーヒー抽出物油溶画分、 シソ精油を実質的 に含まないシソ抽出物を油溶性溶媒によって抽出したシソ抽出物油溶画分、 リン ゴ抽出物を前記油溶性溶媒によって抽出したリンゴ抽出物油溶画分、 バナナ抽出 物を前記油溶性溶媒によって抽出したバナナ抽出物油溶画分、 ブドウ果皮抽出物 を前記油溶性溶媒によって抽出したブドウ果皮抽出物油溶画分、 ブドウ種子抽出 物を前記油溶性溶媒によって抽出したブドウ種子抽出物油溶画分、 ゴポゥ抽出物 を前記油溶性溶媒によって抽出したゴボウ抽出物油溶画分、 マジョラム抽出物を 前記油溶性溶媒によって抽出したマジョラム抽出物油溶画分、 或いはヒマヮリ種 子抽出物を前記油溶性溶媒によって抽出したヒマヮリ種子抽出物油溶画分と、 ト コフエロール、 ァスコルビン酸エステル、 jS -カロチン、 及びリコピンからなる群 から選ばれる 1種以上とを組み合わせたものの抗酸化能が、 上記各種抽出物油溶 画分単体、 又はトコフエロール等の従来公知の抗酸化剤単体の場合よりも高いと いう知見を得た。 本発明者らは、 この知見に基づきさらに検討し、 例えば、 各種 抽出物油溶画分と組み合わせる成分としてトコフエロールを用いた場合には、 ト コフエロールの添加量を抑えることでトコフエロール特有の嫌味嫌臭を低減した 抗酸化組成物を見いだし、 さらに、 上記抽出物油溶画分を用いることで、 トコフ エロール単体の場合よりも有効量を低減できることを見いだし、 もってトコフエ ロールの添加量をより低減できることを見いだし、 本発明を完成させた。  The present inventors have conducted repeated studies to obtain a component that is superior in antioxidant capacity and that is naturally present, and as a result, extracted a potato extract, which is a component derived from potato, with an oil-soluble solvent. An oil-soluble fraction of a potato extract, an oil-soluble fraction of a sweet potato extract obtained by extracting a sweet potato extract with the oil-soluble solvent, an oil-soluble fraction of a coffee extract obtained by extracting a coffee extract with the oil-soluble solvent, and a perilla essential oil Oil extract of a perilla extract extracted from a perilla extract that is not specifically contained with an oil-soluble solvent, an oil extract of an apple extract obtained by extracting an apple extract with the oil-soluble solvent, and a banana extract extracted from the oil-soluble solvent The oil-soluble fraction of the banana extract and the grape skin extract extracted by the oil-soluble solvent are extracted with the oil-soluble fraction of the grape skin extract and the grape seed extract. An oil-soluble fraction of a grape seed extract extracted with an oil-soluble solvent, an oil-soluble fraction of a burdock extract extracted from a Gopo extract with the oil-soluble solvent, an oil-soluble fraction of a marjoram extract extracted from the marjoram extract with the oil-soluble solvent A fraction or an oil-soluble fraction of a sunflower seed extract obtained by extracting the sunflower seed extract with the oil-soluble solvent, and at least one selected from the group consisting of tocopherol, ascorbate, jS-carotene, and lycopene. It has been found that the antioxidant ability of the combination of the above is higher than that of the above-described various oil extracts of the extract alone or the conventionally known antioxidant alone such as tocopherol. The present inventors have further studied based on this finding. For example, when tocopherol is used as a component to be combined with the oil extract of various extracts, by suppressing the amount of tocopherol added, the unpleasant and unpleasant odor peculiar to tocopherol is reduced. And found that the use of the above-described extract oil-soluble fraction can reduce the effective amount compared to the case of tocopherol alone, and that the amount of tocopherol added can be further reduced. We have completed the present invention.
すなわち、 本発明では、  That is, in the present invention,
(a) ジャガイモ抽出物を、 低級アルコール、 ポリオ一ル系有機溶媒、 ベンジルァ ルコ一ル、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリ セリド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出 したジャガイモ抽出物油溶画分; (a) extracting the potato extract with one or more oil-soluble compounds selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils; Extracted by solvent Potato extract oil soluble fraction;
サツマィモ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たサツマィモ抽出物油溶画分;  Satsumaimo extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
コーヒー抽出吻を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコ ール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリ ド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出した コーヒー抽出物油溶画分;  Coffee extracted from a roasted coffee extract with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol-based organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Extract oil-soluble fraction;
シソ精油の含有量が 1重量%以下であるシソ抽出物を、 低級アルコール、 ポリ オール系有機溶媒、 ベンジルアルコール、 酢酸ェチル、 石油エーテル、 グリセ口 ール、 モノグリセリド、 ジグリセリド及び動植物油からなる群より選ばれる 1種 以上の油溶性溶媒によって抽出したシソ抽出物油溶画分;  A perilla extract having a perilla essential oil content of 1% by weight or less is selected from the group consisting of lower alcohols, polyol-based organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Perilla extract oil-soluble fraction extracted with one or more selected oil-soluble solvents;
リンゴ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコー ル、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したリ ンゴ抽出物油溶画分;  Apple extract extracted with at least one oil-soluble solvent selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Oil-soluble fraction;
バナナ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコ一 ル、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したバ ナナ抽出物油溶画分;  Banana extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
ブドウ果皮抽出物を、 低級アルコール、 ポリオ一ル系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たブドウ果皮抽出物油溶画分;  Extract grape skin extract with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Grape skin extract oil-soluble fraction;
ブドウ種子抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たブドウ種子抽出物油溶画分; ゴポゥ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコー ル、 酢酸ェチル、 石油ェ一テル、 グリセロール、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したゴ ボウ抽出物油溶画分; Grape seed extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Grape seed extract oil fraction; The gopo extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils. Bow extract oil-soluble fraction;
マジョラム抽出物を、 低級アルコール、 ポリオ一ル系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たマジョラム抽出物油溶画分;並びに  The marjoram extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Marjoram extract oil fraction; and
ヒマヮリ種子抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルァ ルコール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリ セリド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出 したヒマヮリ種子抽出物油溶画分;  Sunflower seed extracted from sunflower seed extract with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Extract oil-soluble fraction;
からなる群より選ばれる 1種以上の抽出物油溶画分と、  One or more oil extract fractions selected from the group consisting of:
(b) トコフエロール、 ァスコルビン酸エステル、 )3 -カロチン、 及びリコピンから なる群から選ばれる 1種以上と (b) at least one selected from the group consisting of tocopherol, ascorbate,) 3-carotene, and lycopene
を含有する抗酸化組成物が提供される。 An antioxidant composition comprising:
本発明の一態様では、 上記抗酸化組成物は、  In one aspect of the invention, the antioxidant composition comprises:
(a) ジャガイモ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルァ ルコール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリ セリド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出 したジャガイモ抽出物油溶画分;  (a) Potato extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Potato extract oil fraction;
サツマィモ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たサツマィモ抽出物油溶画分;  Satsumaimo extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
シソ精油の含有量が 1重量%以下であるシソ抽出物を、 低級アルコール、 ポリ オール系有機溶媒、 ベンジルアルコール、 酢酸ェチル、 石油エーテル、 グリセ口 ール、 モノグリセリド、 ジグリセリド及び動植物油からなる群より選ばれる 1種 以上の油溶性溶媒によって抽出したシソ抽出物油溶画分; リンゴ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコー ル、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したリ ンゴ抽出物油溶画分; A perilla extract having a perilla essential oil content of 1% by weight or less is selected from the group consisting of lower alcohols, polyol-based organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Perilla extract oil-soluble fraction extracted with one or more selected oil-soluble solvents; Apple extract extracted with at least one oil-soluble solvent selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Oil-soluble fraction;
バナナ抽出物を、 低級アルコール、 ポリオ一ル系有機溶媒、 ベンジルアルコー ル、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したバ ナナ抽出物油溶画分;  The banana extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Nana extract oil fraction;
ブドウ果皮抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油ェ一テル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たブドウ果皮抽出物油溶画分;  Extract grape skin extract with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Grape skin extract oil-soluble fraction;
ブドウ種子抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセ口一ル、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たブドウ種子抽出物油溶画分;  The grape seed extract is treated with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Grape seed extract oil-soluble fraction extracted;
ゴポゥ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコ一 ル、 酢酸ェチル、 石油エーテル、 グリセ口一ル、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したゴ ボウ抽出物油溶画分;  Gopo extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Burdock extract oil-soluble fraction;
マジョラム抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たマジョラム抽出物油溶画分;並びに  Marjoram extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction; and
ヒマヮリ種子抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルァ ルコール、 酢酸ェチル、 石油ェ一テル、 グリセロール、 モノグリセリド、 ジグリ セリド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出 したヒマヮリ種子抽出物油溶画分;  Castor seed extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Castor seed extract oil soluble fraction;
からなる群より選ばれる 1種以上の抽出物油溶画分と、 (b) トコフエロール、 ァスコルビン酸エステル、 jS -カロチン、 及びリコピンから なる群から選ばれる 1種以上と One or more oil extract fractions selected from the group consisting of: (b) at least one selected from the group consisting of tocopherol, ascorbate, jS-carotene, and lycopene
を含有するものであることが好ましい。 Is preferable.
また、 本発明の他の一態様では、 上記抗酸化組成物は、  In another aspect of the present invention, the antioxidant composition comprises:
(a) ジャガイモ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルァ ルコール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリ セリド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出 したジャガイモ抽出物油溶画分; (a) Potato extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Potato extract oil fraction;
サツマィモ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たサツマィモ抽出物油溶画分;  Satsumaimo extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
シソ精油の含有量が 1重量%以下であるシソ抽出物を、 低級アルコール、 ポリ オール系有機溶媒、 ベンジルアルコール、 酢酸ェチル、 石油エーテル、 グリセ口 —ル、 モノグリセリド、 ジグリセリド及び動植物油からなる群より選ばれる 1種 以上の油溶性溶媒によって抽出したシソ抽出物油溶画分;  Extracting perilla extract containing less than 1% by weight of perilla essential oil from the group consisting of lower alcohol, polyol organic solvent, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride and animal and vegetable oils Perilla extract oil-soluble fraction extracted with one or more selected oil-soluble solvents;
リンゴ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコ一 ル、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したリ ンゴ抽出物油溶画分;  The apple extract is extracted with at least one oil-soluble solvent selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
バナナ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコ一 ル、 酢酸ェチル、 石油エーテル、 グリセ口一ル、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したバ ナナ抽出物油溶画分;  Extract the banana extract with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Oil extract of banana extract;
ブドウ果皮抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たブドウ果皮抽出物油溶画分;  The grape skin extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Grape skin extract oil-soluble fraction;
ブドウ種子抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たブドウ種子抽出物油溶画分; Grape seed extract, lower alcohol, polyol organic solvent, benzyl alcohol Grape seed extract oil-soluble fraction extracted with at least one oil-soluble solvent selected from the group consisting of coal, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride and animal and vegetable oils;
ゴポゥ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコー ル、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したゴ ボウ抽出物油溶画分;  Burdock extract extracted from Gopo extract with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils Oil-soluble fraction;
マジョラム抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たマジョラム抽出物油溶画分;並びに  Marjoram extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction; and
ヒマヮリ種子抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルァ ルコール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリ セリド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出 したヒマヮリ種子抽出物油溶画分;  Sunflower seed extracted from sunflower seed extract with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Extract oil-soluble fraction;
からなる群より選ばれる 1種以上の抽出物油溶画分と、  One or more oil extract fractions selected from the group consisting of:
(b) トコフエ口一ル及びァスコルビン酸エステルからなる群から選ばれる 1種以 上と (b) at least one selected from the group consisting of tocophere and ascorbate
を含有するものであることが好ましい。本態様においては、上記 (b)成分の中でも、 トコフエロール又はァスコルビン酸エステルを単独で、 またはトコフエロール及 びァスコルビン酸エステルを併用することが好ましい。 Is preferable. In the present embodiment, among the above-mentioned components (b), it is preferable to use tocopherol or ascorbic acid ester alone or tocopherol and ascorbic acid ester in combination.
該抗酸化組成物中の (a)成分と (b)成分の比率は、 重量比で 1 : 9〜9 : 1である ことが好ましい。  The ratio of component (a) to component (b) in the antioxidant composition is preferably 1: 9 to 9: 1 by weight.
また、 本発明では、 上記抗酸化組成物を含むことを特徴とする動植物油が提供 され、 上記抗酸化組成物の含有量が、 動植物油全量に対して 0 . 0 1重量%〜1 0重量%であることが好ましく、 該動植物油は、 特に限定されないが、 ラッカセ ィ油、 アーモンド油、 カカオ油、 ヘーゼルナッツ油、 マカデミアナッツ油、 菜種 油又は魚油であることが好ましい。  Further, according to the present invention, there is provided an animal or vegetable oil characterized by containing the antioxidant composition, wherein the content of the antioxidant composition is 0.01% by weight to 10% by weight based on the total amount of the animal or vegetable oil. %, And the animal and vegetable oil is not particularly limited, but is preferably lacquer oil, almond oil, cocoa oil, hazelnut oil, macadamia nut oil, rapeseed oil or fish oil.
また、 本発明では、 上記動植物油を含むことを特徴とする飲食品、 医薬品、 香 粧品、 及び家庭用品が提供される。 Further, in the present invention, there is provided a food or drink, a medicine, or a fragrance comprising the above-mentioned animal or vegetable oil. Cosmetics and household goods are provided.
また、 本発明では、 上記抗酸化組成物を動植物油に添加することにより、 その 動植物油に抗酸化能を付与する方法が提供される。  In addition, the present invention provides a method for imparting antioxidant ability to animal and vegetable oils by adding the above antioxidant composition to animal and vegetable oils.
本発明によれば、 トコフエ口一ル、 ァスコルビン酸エステル、 ]3 -カロチン、 及 びリコピンから選ばれる 1種以上を、 各種抽出物油溶画分と併用することによつ て、 実用に適した使用量の範囲において、 トコフエロール等の従来公知の抗酸化 剤単体の抗酸化能と、 天然物抽出油溶画分の抗酸化能とが相乗的に増強される。 According to the present invention, it is suitable for practical use by using at least one selected from tocophere, ascorbic acid ester,] 3-carotene, and lycopene together with various extract oil-soluble fractions. Within the range of the used amount, the antioxidant ability of the conventionally known antioxidant alone such as tocopherol and the antioxidant ability of the natural product extracted oil fraction are synergistically enhanced.
• このため、 食品の賞味期間、 化粧品等の製品の陳列期間をより長くすることが可 能となる。 また、 トコフエロールと同等若しくはそれ以上の抗酸化力を得るため に、 従来の抗酸化剤、 例えばトコフエロールの添加量を低減させることができる ため、 トコフエロール特有の嫌味嫌臭を低減させることが可能となる。 また、 ト コフエロール単体を使用する場合に比べて、 抗酸化組成物の有効量そのものをよ り低くすることができるため、 トコフヱロールの添加量をより低減させることが 可能となる。 図面の簡単な説明 • For this reason, it is possible to extend the shelf life of food and the display period of products such as cosmetics. In addition, the amount of the conventional antioxidant, for example, tocopherol can be reduced in order to obtain an antioxidant power equal to or higher than that of tocopherol, so that the unpleasant odor and odor peculiar to tocopherol can be reduced. . In addition, the effective amount of the antioxidant composition itself can be lower than when using tocopherol alone, so that the amount of tocopherol added can be further reduced. Brief Description of Drawings
図 1は、本発明の (a)成分として使用される各種抽出物油溶画分の製造工程例を 示したフローチャートである。 発明を実施するための最良の形態  FIG. 1 is a flow chart showing an example of the production process of oil-soluble fractions of various extracts used as component (a) of the present invention. BEST MODE FOR CARRYING OUT THE INVENTION
以下に本発明を詳しく説明する。  Hereinafter, the present invention will be described in detail.
本発明の抗酸化組成物は、  The antioxidant composition of the present invention,
(a) ジャガイモ抽出物を前記所定の油溶性溶媒によって抽出したジャガイモ抽 出物油溶画分、 サツマィモ抽出物を前記所定の油溶性溶媒によって抽出したサッ マイモ抽出物油溶画分、 コーヒー抽出物を前記所定の油溶性溶媒によって抽出し たコーヒー抽出物油溶画分、 シソ精油の含有量が 1重量%以下であるシソ抽出物 を、 所定の油溶性溶媒によって抽出したシソ抽出物油溶画分、 リンゴ抽出物を前 記所定の油溶性溶媒によって抽出したリンゴ抽出物油溶画分、 バナナ抽出物を前 記所定の油溶性溶媒によって抽出したバナナ抽出物油溶画分、 ブドウ果皮抽出物 を前記所定の油溶性溶媒によって抽出したブドウ果皮抽出物油溶画分、 ブドウ種 子抽出物を前記所定の油溶性溶媒によって抽出したブドウ種子抽出物油溶画分、 ゴポゥ抽出物を前記所定の油溶性溶媒によって抽出したゴポゥ抽出物油溶画分、 マジョラム抽出物を前記所定の油溶性溶媒によって抽出したマジョラム抽出物油 溶画分、 及びヒマヮリ種子抽出物を前記所定の油溶性溶媒によって抽出したヒマ ヮリ種子抽出物油溶画分からなる群より選ばれる 1種以上の抽出物油溶画分と、 (b) トコフエロール、 ァスコルビン酸エステル、 )3 -カロチン、 及びリコピンか らなる群から選ばれる 1種以上とを含有する。 (a) an oil-soluble fraction of a potato extract extracted from the potato extract with the predetermined oil-soluble solvent, an oil-soluble fraction of a sweet potato extract extracted from the sweet potato extract with the predetermined oil-soluble solvent, and a coffee extract A perilla extract having a perilla essential oil content of 1% by weight or less, and a perilla extract extracted with the predetermined oil-soluble solvent. Oil extract of the apple extract obtained by extracting the apple extract with the above-mentioned oil-soluble solvent, oil-soluble fraction of the banana extract obtained by extracting the banana extract with the above-mentioned oil-soluble solvent, and grape peel extract The grape peel extract oil-soluble fraction extracted with the predetermined oil-soluble solvent, the grape seed extract oil-soluble fraction extracted from the grape seed extract with the predetermined oil-soluble solvent, The oil-soluble fraction of Gopo extract extracted with the oil-soluble solvent, the oil-soluble fraction of marjoram extract obtained by extracting the marjoram extract with the predetermined oil-soluble solvent, and the sunflower seed extract were extracted with the predetermined oil-soluble solvent. One or more oil extract fractions selected from the group consisting of oil fractions of castor seed extract; and (b) selected from the group consisting of tocopherol, ascorbate,) 3-carotene, and lycopene Contains one or more.
本明細書において、 「抗酸化剤」 とは、 自動酸化性物質に対して酸素の作用を防 止する性質をもつ物質のことである。 自動酸化(酸素の作用)を防止する機能(抗 酸化能) はいろいろに分類できる。  As used herein, the term “antioxidant” refers to a substance having a property of preventing the action of oxygen on an autoxidizable substance. The function of preventing autoxidation (the effect of oxygen) (antioxidant capacity) can be classified in various ways.
例えば、 (1) 自動酸化の連鎖反応を抑制するラジカル阻害剤、 (2) 鉄、 銅など の金属の酸化促進作用を不活性にする金属不活化剤、 (3) 過酸化物を非ラジカル 分解して不活性化する過酸化物分解剤、 (4) 自ら酸化防止作用はもたないが、 ラ ジカル阻害剤と共同してその作用を増強させる相乗剤と四つに分けることもでき る。  For example, (1) a radical inhibitor that suppresses the chain reaction of autoxidation, (2) a metal inactivator that inactivates the pro-oxidant action of metals such as iron and copper, and (3) non-radical decomposition of peroxide. (4) It has no antioxidant effect by itself, but can be divided into four groups: a synergist that enhances its effect in cooperation with a radical inhibitor.
本発明における 「抗酸化組成物」 とは、 上記に記載したような、 いろいろな機 能により、自動酸化する物質に対して、自動酸化を防止する組成物のことをいう。 本発明の (a)成分として使用される各種抽出物油溶画分は、各種植物原料から得 た抽出物を、 油溶性溶媒によって更に抽出することによって得ることができる。 ここで、 各種抽出物は、 たとえば、 植物原料を乾燥させて適宜の大きさに裁断し たものを溶媒に一定条件で浸し、当該溶媒から植物原料を濾過、除去後、濃縮し、 さらに精製処理を行うことにより得ることができる。  The “antioxidant composition” in the present invention refers to a composition that prevents autoxidation of a substance that autoxidizes by various functions as described above. The oil-soluble fractions of various extracts used as the component (a) of the present invention can be obtained by further extracting extracts obtained from various plant raw materials with an oil-soluble solvent. Here, various extracts are obtained, for example, by drying a plant material and cutting it into an appropriate size, immersing the extract in a solvent under a certain condition, filtering and removing the plant material from the solvent, concentrating the extract, and further purifying the extract. Can be obtained.
以下、 図 1のフローチャートに基づいて、 より具体的に説明する。  Hereinafter, a more specific description will be given based on the flowchart of FIG.
図 1は、本発明の (a)成分として使用される各種抽出物油溶画分の製造工程例を 示したものである。 図中、 点線で示す工程は任意に経ることができる工程を意味 する。  FIG. 1 shows an example of the production process of the oil-soluble fractions of various extracts used as the component (a) of the present invention. In the figure, the steps indicated by the dotted lines indicate steps that can be arbitrarily performed.
まず、 本発明において、 植物原料 (1)としては、 ジャガイモ、 サツマィモ、 コー ヒー豆、 シソ、 リンゴ、 バナナ、 ブドウ果皮、 ブドウ種子、 ゴボウ、 マジョラム、 ヒマヮリ種子を用いることができる。 First, in the present invention, the plant raw materials (1) include potato, sweet potato, coffee beans, perilla, apple, banana, grape peel, grape seed, burdock, marjoram, Castor seeds can be used.
原料がジャガイモ、 サツマィモの場合は、 塊茎、 根茎、 茎、 葉を用いることが できる。  When the raw material is potato or sweet potato, tubers, rhizomes, stems and leaves can be used.
原料がコーヒー豆の場合は、 生あるいはローストコーヒー豆を特に制限なく用 いることができる。 またいずれの品種の豆も使用できるが、 口ブス夕種の生豆が 特に好ましい。  When the raw material is coffee beans, raw or roasted coffee beans can be used without particular limitation. Any type of bean can be used, but green soybeans are particularly preferred.
原料がシソの場合は、 シソの葉や茎を用いることができる。 本発明において、 シソとしてはシソ属 (Perilla) の植物を特に制限なく用いることができ、 たとえ ば'、 ァ刀ンソ (Perilla frutescens Britton var. acuta Kudo)、 力夕メンソ (Perilla forma discolor Makino)、 J才ンソ (Perilla forma viridis Majdno)、 チリメンン ソ (Perilla frutescens Britton var. crisp a Decne)、 カタチリメンンソ (Perilla forma atro-purnurea Kudoノ、 ,ォナリメノンソ (Perilla forma viridicnspa 丄 Vlakmo)、エゴ (Perilla frutescens Britton var. Japonica Hara) 挙りるしと力 できる。  When the raw material is perilla, perilla leaves and stems can be used. In the present invention, as a perilla, a plant of the genus Perilla can be used without any particular limitation. For example, ', Perilla frutescens Britton var.acuta Kudo, Perilla forma discolor Makino, J-year-old Nsso (Perilla forma viridis Majdno), Cilimennso (Perilla frutescens Britton var. Japonica Hara) I can do it.
原料がリンゴゃバナナの場合は、 果皮を含めた果実を用いる。 また、 果皮のみ を使用することも出来る。  If the raw material is apple or banana, use the fruit including the peel. Alternatively, only the peel can be used.
原料がブドゥ果皮の場合は、 いずれの品種のブドウ果皮も使用することが出来 るが、 特に、 赤ブドウの各品種が好ましい。 ,  When the raw material is bud peel, any kind of grape peel can be used, but each kind of red grape is particularly preferred. ,
原料がブドゥ種子の場合は、 いずれの品種のブドウ種子も使用することが出来 る。  If the raw material is bud seed, grape seeds of any variety can be used.
原料がゴボウの場合は、 根茎を用いる。  If burdock is used as the raw material, use the rhizome.
原料がマジョラムの場合は、 茎、 葉を用いる。  If the raw material is marjoram, use stems and leaves.
原料がヒマヮリ種子の場合は、 キク科、 ヒマヮリ属に属するヒマヮリの種子を 用いる。  If the raw material is sunflower seeds, use sunflower seeds belonging to the family Asteraceae or the genus Himagri.
これら植物原料を単独で或いは 2種以上を使用し、 乾燥させ、 適宜の大きさに 裁断し、 原料破砕物 (2)とする。  These plant materials are used alone or in combination of two or more, dried, and cut into appropriate sizes to obtain crushed material (2).
続いて、 原料破砕物 (2)を用いて各種抽出物 (3)を得る。 各種抽出物 (3)を抽出す る際には、 水、 低級アルコール、 含水低級アルコール等を用いて溶媒抽出 (A)によ り行う。 本明細書において、「低級アルコール」とは、炭素数が 1ないし 4のアルコール、 すなわち、 メタノール、 エタノール、 プロパノール、 ブタノ一ルをいい、 特にメ 夕ノール、 エタノール等が好ましい。 また、 「含水低級アルコール」 とは、 水と低 級アルコールとの混合物を意味する。 抽出操作は特に限定されるものではなく、 上記植物や用いる溶媒により異なるが、 通常、 上記溶媒に原料破碎物を 4 °C〜1 0 0 °Cの温度で浸漬または穏やかに撹拌して抽出する事により行う。 さらに本出 願前周知のソックスレ一抽出器などの装置を用いると効率よく抽出操作を行うこ とができる。 抽出に要する時間は、 通常 3 0分〜 1 2時間程度である。 なお、 本 出願前から知られている多段抽出法を採用してもよい。 Subsequently, various extracts (3) are obtained using the crushed material (2). Extraction of various extracts (3) is carried out by solvent extraction (A) using water, lower alcohol, hydrated lower alcohol and the like. As used herein, the term "lower alcohol" refers to an alcohol having 1 to 4 carbon atoms, that is, methanol, ethanol, propanol, and butanol, and particularly, methanol, ethanol, and the like. “Hydrophilic lower alcohol” means a mixture of water and lower alcohol. The extraction operation is not particularly limited, and varies depending on the plant and the solvent used.In general, the crushed material is immersed in the solvent at a temperature of 4 ° C to 100 ° C or extracted by gentle stirring. Do by things. Further, if a device such as a soxhlet extractor known before the present application is used, the extraction operation can be performed efficiently. The time required for extraction is usually about 30 minutes to 12 hours. Note that a multi-stage extraction method known before the present application may be adopted.
本発明において、 上記で得られた抽出物 (3)を、 更に、 クロマログラフィー処理 (D)することにより有効成分を濃縮して得た濃縮物 (6)を抽出物として用いても良 い (図 1中、 点線で示す)。 例えば、 上記抽出物を、 予め作成、 調製したクロマト グラフィー用カラムに注ぎ込み、 ついで、 溶媒から構成される溶出液を注ぎ込ん でカラム内に一時的に保持されたものを溶媒とともに流し去り、 流出する溶媒を 公知の手段でいくつかに分ける方法を採用すればよい。 カラムに使用する担持体 は特に限定されないが、 シリカゲル、 ダイヤイオン HP20 (三菱化成) やアンバ 一ライト XAD-2 (Rohm&Haas社)、 日立ゲル # 3010 (日立化成) 等の合成吸着 剤を挙げることが出来る。溶出温度は通常室温で行うが、低温下で行っても良い。 上記方法により流出する溶媒を公知の手段で分取して画分を得る。 各画分あるい は複数の画分を合一したものを、 さらに減圧下にて溶媒を留去したものを抽出物 として用いても良い。  In the present invention, the extract (3) obtained above may be further subjected to a chromatographic treatment (D) to concentrate the active ingredient (6). (Indicated by the dotted line in Fig. 1). For example, the above extract is poured into a chromatographic column prepared and prepared in advance, and then an eluate composed of a solvent is poured, and what is temporarily retained in the column is washed away with the solvent, and the solvent that flows out May be adopted by a known method. The carrier used for the column is not particularly limited, but examples thereof include synthetic adsorbents such as silica gel, Diaion HP20 (Mitsubishi Kasei), Amberlite XAD-2 (Rohm & Haas), and Hitachi Gel # 3010 (Hitachi Chemical). I can do it. The elution is usually performed at room temperature, but may be performed at a low temperature. The solvent flowing out by the above method is fractionated by a known means to obtain a fraction. Each fraction or a combination of a plurality of fractions may be used as an extract after further distilling off the solvent under reduced pressure.
また、 本発明において、 上記方法により得られる抽出物以外に、 該抽出物に何 らかの処理を施して得られた抽出物、 例えば抽出物からさらに溶媒を除去した濃 縮物、 所謂エキストラクトゃ抽出物からさらに特定の化合物を除去したものなど を抽出物として用いてもよい。  In the present invention, in addition to the extract obtained by the above method, an extract obtained by subjecting the extract to any treatment, for example, a concentrate obtained by further removing a solvent from the extract, a so-called extractも の An extract obtained by further removing a specific compound from the extract may be used as the extract.
また、 本発明において、 原料破砕物 (2)の代わりに、 上記植物原料 (1)を破碎した 後、 水蒸気蒸留 (C)し、 得られた蒸留残渣を破砕した水蒸気蒸留残渣破碎物 (5)を 用いて抽出物を得ても良い (図 1中、 点線で示す)。 この場合、 水蒸気蒸留残渣破 砕物から各種抽出物を抽出する際に用いられる溶媒は、 水、 低級アルコール、 含 水低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリド及び動植物油の中 から選ばれる 1種あるいは 2種以上の溶媒であることが好ましい。 Further, in the present invention, instead of the raw material crushed material (2), after crushing the plant material (1), steam distillation (C) is performed, and the obtained distillation residue is crushed to obtain a crushed steam distillation residue (5). The extract may be obtained using (see the dotted line in FIG. 1). In this case, the solvent used for extracting various extracts from the crushed steam distillation residue is water, lower alcohol, The solvent is preferably one or more solvents selected from water lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils.
本明細書において、 「モノダリセリド」 とは、 グリセロールの脂肪酸エステルの うち、 1分子の脂肪酸によりエステル化されたものであり、 脂肪酸としては、 力 ブロン酸、パルミチン酸、ステアリン酸などが挙げられる。また、 「ジグリセリド」 とは、 グリセロールの脂肪酸エステルのうち、 2分子の脂肪酸によりエステル化 されたものであり、 脂肪酸としては、 カブロン酸、 パルミチン酸、 ステアリン酸 などが挙げられる。 また、 本明細書において、 「動植物油」 とは、 トリグリセリド を主成分とする油のことを指し、 常温で液状であれば特に制限なく使用すること ができる。  In the present specification, “monodaliceride” is a fatty acid ester of glycerol esterified with one molecule of a fatty acid, and examples of the fatty acid include bromobronic acid, palmitic acid, and stearic acid. The “diglyceride” is a fatty acid ester of glycerol esterified with two molecules of fatty acid, and examples of the fatty acid include cabronic acid, palmitic acid, and stearic acid. In this specification, “animal or vegetable oil” refers to an oil containing triglyceride as a main component, and any oil can be used without any particular limitation as long as it is liquid at normal temperature.
本発明において用いられる抽出物のうち、 シソから得られたシソ抽出物は、 シ ソ精油の含有量 1 %以下のものであり、シソ精油を実質的に含まないものである。 つまり、 本発明において、 シソ抽出物中、 シソ精油の含有量は 1重量%以下であ り、 好ましくは、 0 . 1重量%以下であり、 より好ましくは 0 . 0 1重量%以下 である。 本明細書において、 シソ精油の含有量の測定はガスクロマトグラフィー によるものである。 本明細書で 「シソ精油」 とは、 シソに含まれる揮発性香気成 分の複合体のことをいう。 精油はべリルアルデヒドを主成分とし、 他に 1—リモ ネン、 力リオフィレン、 -フアルネセン、 シソオール、 リナロール、 ペリルァ ルコール等を含んでいる。 エゴマ由来の精油はべリルアルデヒドを全く含まず 1 ーピペリトン、 ナギナタケトン等を主成分として含有している。 いずれの抽出物 も市販品を用いても良い。  Among the extracts used in the present invention, the perilla extract obtained from perilla has a perilla essential oil content of 1% or less and is substantially free of perilla essential oil. That is, in the present invention, the content of perilla essential oil in the perilla extract is 1% by weight or less, preferably 0.1% by weight or less, and more preferably 0.01% by weight or less. In the present specification, the content of perilla essential oil is measured by gas chromatography. As used herein, the term “perilla essential oil” refers to a complex of volatile aroma components contained in perilla. The essential oil contains berylaldehyde as the main component, and also contains 1-limonene, rioliophylene, -fuarnesene, perilla, linalool, and peryl alcohol. The essential oil derived from perilla contains no berylaldehyde and contains 1-piperitone and naginata ketone as main components. Commercial products may be used for any of the extracts.
本発明において、 (a)成分として用いられる各種抽出物油溶画分は、 上記のよう にして得られた抽出物を低級アルコール、 ポリオ一ル系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって溶媒抽 出 -濾過 (B)を行うことによって得られる。  In the present invention, the oil-soluble fractions of various extracts used as the component (a) are obtained by extracting the extract obtained as described above with a lower alcohol, a polyol organic solvent, benzyl alcohol, ethyl acetate, petroleum ether. , Glycerol, monoglyceride, diglyceride and animal and vegetable oils by performing solvent extraction-filtration (B) with at least one oil-soluble solvent selected from the group consisting of:
抽出操作は特に限定されるものではなく、 抽出物を得る際に用いられた植物材 料、 溶媒により異なるが、 通常、 低級アルコール (たとえば、 メタノール、 エタ ノール、 ブタノ一ル、 プロパノール)、 ポリオール系有機溶媒 (たとえば、 ェチレ ングリコ一ル、 プロピレングリコール)、 ベンジルアルコール、 酢酸ェチル、 石油 エーテル、 グリセ口ール、 モノグリセリド、 ジグリセリド、 及び動植物油 (たと えば、 大豆油、 コーン油、 菜種油、 ラード) からなる群より選ばれる 1種以上の 油溶性溶媒、 好ましくは、 ベンジルアルコールに、 抽出物を 2 0 °C〜8 0 °C、 好 ましくは 4 0 °C〜8 0 °Cの温度で浸漬または穏やかに撹拌して抽出する事により 行う。 抽出に要する時間は、 通常 1 0分〜 1 2時間程度、 好ましくは 3 0分〜 3 時間である。 なお、 本出願前から知られている多段抽出法を採用してもよい。 抽 出後、 濾過操作を施した後、 濾過液 (4)を抽出物油溶画分として用いる。 The extraction operation is not particularly limited, and varies depending on the plant material and the solvent used to obtain the extract, but usually, lower alcohols (eg, methanol, ethanol, etc.) Phenol, organic solvents such as ethyl alcohol, ethyl alcohol, propylene glycol), benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils (for example, One or more oil-soluble solvents selected from the group consisting of soybean oil, corn oil, rapeseed oil, and lard), preferably benzyl alcohol, and the extract at 20 ° C to 80 ° C, preferably 40 ° C. Extraction is performed by immersion or gentle stirring at a temperature of ° C to 80 ° C. The time required for the extraction is usually about 10 minutes to 12 hours, preferably 30 minutes to 3 hours. Note that a multi-stage extraction method known before the present application may be employed. After extraction and filtration, the filtrate (4) is used as the extract oil-soluble fraction.
なお、 原料に、 本来精油をほとんど含まないもの、 あるいは、 水蒸気蒸留等に より精油を除去したものを使用した場合、 直接、 原料を低級アルコ一ル、 ポリオ ール系有機溶媒、 ベンジルアルコール、 酢酸ェチル、 石油エーテル、 グリセロー ル、 モノグリセリド、 ジグリセリド、 及び動植物油からなる群より選ばれる 1種 以上の油溶性溶媒によって抽出することにより油溶画分を調整してもよいが、 有 効成分の抽出効率からみて今一つである。  If the raw material contains essentially no essential oil, or the one from which the essential oil has been removed by steam distillation or the like, the raw material is directly used as a lower alcohol, a polyol organic solvent, benzyl alcohol, or acetic acid. The oil-soluble fraction may be adjusted by extraction with one or more oil-soluble solvents selected from the group consisting of ethyl, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils. This is not enough in terms of efficiency.
本発明の坊酸化組成物は、 上記方法によって得られた各種抽出物油溶画分、 す なわち、 ジャガイモ抽出物油溶画分、 サツマィモ抽出物油溶画分、 コ一ヒ一抽出 物油溶画分、 シソ抽出物油溶画分、 リンゴ抽出物油溶画分、 バナナ抽出物油溶画 分、 ブドウ果皮抽出物油溶画分、 ブドウ種子抽出物油溶画分、 ゴボウ抽出物油溶 画分、 マジョラム抽出物油溶画分、 及びヒマヮリ種子抽出物油溶画分からなる群 より選ばれる 1種以上の抽出物油溶画分を (a)成分として含み、かつ、(b)成分とし てトコフエロール、 ァスコルビン酸エステル、 i3 -カロチン、 及びリコピンからな る群から選ばれる 1種以上とを含む。本発明の抗酸化組成物は、(a)成分と (b)成分 を併用することにより、 トコフエロールと同等若しくはそれ以上の抗酸化能を維 持しながら、 抗酸化剤由来の異味異臭を低減するという優れた効果を奏するもの である。  The oxidized botanical composition of the present invention comprises various extract oil-soluble fractions obtained by the above method, that is, a potato extract oil-soluble fraction, a sweet potato extract oil-soluble fraction, and an oil extract-oil. Oil fraction, Perilla extract oil fraction, Apple extract oil fraction, Banana extract oil fraction, Grape peel extract oil fraction, Grape seed extract oil fraction, Burdock extract oil A component comprising at least one extract oil-soluble fraction selected from the group consisting of a soluble fraction, an oil-soluble fraction of marjoram extract, and an oil-soluble fraction of sunflower seed extract; And at least one member selected from the group consisting of tocopherol, ascorbate, i3-carotene, and lycopene. The antioxidant composition of the present invention reduces the off-flavor and odor derived from the antioxidant while maintaining the same or higher antioxidant ability as tocopherol by using the components (a) and (b) in combination. This is an excellent effect.
上記 (a)成分である抽出物油溶画分の中では、 ジャガイモ抽出物油溶画分、 サッ マイモ抽出物油溶画分、 シソ抽出物油溶画分、 リンゴ抽出物油溶画分、 バナナ抽 出物油溶画分、 ブドウ果皮抽出物油溶画分、 ブドウ種子抽出物油溶画分、 ゴボウ 抽出物油溶画分、 マジョラム抽出物油溶画分、 及びヒマヮリ種子抽出物油溶画分 からなる群より選ばれる 1種以上の抽出物油溶画分であることが好ましい。 これ らの抽出物油溶画分は抗酸化効果に特に優れ、 かつ素材臭や着色などの問題も殆 どなく扱いが容易であるからである。 これに対し、 コーヒ一抽出物油溶 11分は素 材臭があり、 色も黒いことから扱いづらい場合がある。 Among the oil extract fractions of component (a), the oil extract of potato extract, oil extract of sweet potato extract, oil extract of perilla extract, oil extract of apple extract, Banana extract oil-soluble fraction, grape peel extract oil-soluble fraction, grape seed extract oil-soluble fraction, Burdock It is preferably at least one extract oil-soluble fraction selected from the group consisting of an extract oil-soluble fraction, a marjoram extract oil-soluble fraction, and a sunflower seed extract oil-soluble fraction. This is because these extract oil-soluble fractions are particularly excellent in antioxidant effect, and are easy to handle with almost no problems such as material odor and coloring. In contrast, coffee extract oil-soluble for 11 minutes has a raw material odor and its color is black, so it may be difficult to handle.
(b)成分であるトコフエ口一ル、 ァスコルビン酸エステル、 β -カロチン、 及び リコピンのなかでは、 トコフエロール又はァスコルビン酸エステルをそれぞれ単 独で、 或いはトコフエ口一ル及びァスコルビン酸エステルを併用することが好ま しい。 前述したようにトコフエロールは安全で且つ優れた抗酸化効果を示すもの であり、 ァスコルビン酸エステルは油溶性であることから、 脂質などの油溶性成 分に使いやすい。 また、 トコフエロール及びァスコルビン酸を併用すると、 これ らの成分を単独で用いた場合よりもさらに高い抗酸化効果を奏することができる。 また、 トコフエロール及びァスコルビン酸を併用することによりトコフエロール の添加量をさらに低く抑えることもできる。 なお、 トコフエロールとしては、 α - トコフエロール、 )3 -トコフエロール、 Τ -トコフエロール、 -トコフエロール等 の 1種または 2種以上を制限無く使用することができる。  Among the components (b), tocopherol, ascorbic acid ester, β-carotene, and lycopene, tocopherol or ascorbic acid ester may be used alone or in combination with tocopheric acid and ascorbic acid ester. I like it. As described above, tocopherol exhibits a safe and excellent antioxidant effect, and ascorbic acid ester is oil-soluble, so that it is easy to use for oil-soluble components such as lipids. When tocopherol and ascorbic acid are used in combination, a higher antioxidant effect can be obtained than when these components are used alone. In addition, the combined use of tocopherol and ascorbic acid can further reduce the amount of tocopherol added. As the tocopherol, one or more of α-tocopherol,) 3-tocopherol, Τ-tocopherol, -tocopherol and the like can be used without limitation.
本発明の抗酸化組成物中、 (a)成分と (b)成分の比率は、 重量比で 1 : 9〜9 : 1 であることが好ましく、 2 : 8〜7 : 3であることがより好ましく、 3 : 7〜5 : 5であることがさらに好ましい。  In the antioxidant composition of the present invention, the ratio of the component (a) to the component (b) is preferably 1: 9 to 9: 1 by weight, more preferably 2: 8 to 7: 3. It is more preferably 3: 7 to 5: 5.
本発明において、 (a)成分の比率が少なすぎると、 たとえばトコフエロールとの 組合せの場合には、 トコフエロール特有の異味異臭が目立ってくる、 また、 (b) 成分の比率が少なすぎると、抗酸化効果が充分でない場合があり、好ましくない。 本発明の抗酸化組成物は、(a)成分および (b)成分の他に、必要に応じて他の钪酸 化剤を配合することもできる。 このようなものとして、 例えばローズマリーゃセ ージ、 バジル、 緑茶のの各抽出物等を挙げることができる。  In the present invention, if the proportion of the component (a) is too small, for example, in the case of a combination with tocopherol, an unpleasant odor peculiar to tocopherol becomes conspicuous, and if the proportion of the component (b) is too small, antioxidant The effect may not be sufficient, which is not preferable. The antioxidant composition of the present invention may further contain, if necessary, other deoxidizing agents in addition to the components (a) and (b). Such extracts include, for example, extracts of rosemary sage, basil, and green tea.
本発明の抗酸化組成物は、 酸化されやすい動植物油に添加 ·配合し、 動植物油 の酸化を防止することができる。 上記動植物油としては、 大豆油、 コーン油、 紅 花油、 綿実油、 ラッカセィ油 (ピーナッツ油)、 アーモンド油、 カカオ油、 へーゼ ルナッツ油、 マカデミアナッツ油、 菜種油 (キャノーラ油)、 ラード、 ヘッド、 r% 夕一、 いわし油などの魚油、 肝油などを挙げることができるが、 これらに限定さ れるものではない。 好ましくは、 ラッカセィ油、 ァ一モンド油、 カカオ油、 へ一 ゼルナッツ油、 マカデミアナッツ油、 魚油を挙げることができる。 The antioxidant composition of the present invention can be added to and blended with animal and vegetable oils that are easily oxidized to prevent oxidation of the animal and vegetable oils. The animal and vegetable oils include soybean oil, corn oil, safflower oil, cottonseed oil, laccase oil (peanut oil), almond oil, cocoa oil, hazelnut oil, macadamia nut oil, rapeseed oil (canola oil), lard, head, r % In the evening, fish oil such as sardine oil, liver oil and the like can be mentioned, but not limited thereto. Preferably, laccase oil, almond oil, cocoa oil, methanol nut oil, macadamia nut oil and fish oil can be mentioned.
本発明の動植物油に含有される抗酸化組成物の量は、 目的に応じて変わり、 特 に限定されるものではないが、 通常、 動植物油全量に対して、 0 . 0 1重量%〜 1 0重量%であれば目的は達成される。 好ましくは、 0 . 0 5重量%〜3重量% である。  The amount of the antioxidant composition contained in the animal and vegetable oils of the present invention varies depending on the purpose and is not particularly limited, but is usually 0.01% by weight to 1% by weight based on the total amount of the animal and vegetable oils. If the content is 0% by weight, the object is achieved. Preferably, it is 0.05% to 3% by weight.
本発明の動植物油は、 抗酸化組成物の他に、 無水珪酸塩、 無水硫酸塩、 各種無 機塩化物、 糖類、 多糖類等の増量増粘剤、 界面活性剤、 安定化剤、 安息香酸、 安 息香酸ナトリウム等の抗菌剤、 色素、 香料あるいは BHT、 BHA、 ビタミン C等 の公知の抗酸化剤などをあらかじめ共存させておいてもよい。  The animal and vegetable oils of the present invention may contain, in addition to the antioxidant composition, thickening agents such as anhydrous silicates, anhydrous sulfates, various inorganic chlorides, saccharides, polysaccharides, etc., surfactants, stabilizers, and benzoic acid. An antibacterial agent such as sodium benzoate, a dye, a fragrance, or a known antioxidant such as BHT, BHA, vitamin C, or the like may be coexisted in advance.
本発明の抗酸化組成物を含有する動植物油は、各種飲食品;フレダランス製品、 基礎化粧品、 頭髪化粧品、 浴用剤等の香粧品; トイレタリ一製品、 洗剤 ·仕上げ 剤、 芳香消臭剤等の家庭用品;医薬品など、 動植物油を使用するものに対しては いずれにおいても使用することが出来る。  Animal and vegetable oils containing the antioxidant composition of the present invention include various foods and beverages; fragrance products, basic cosmetics, hair cosmetics, bath cosmetics and other cosmetics; toiletries, detergents, finishing agents, aromatic deodorants, etc. Supplies: Any of those that use animal and vegetable oils, such as pharmaceuticals, can be used.
上記飲食品としては、 例えば、 チョコレート、 ガム、 キャンディ、 ポテトチッ ブス、 クッキー、 ビスケットなどの製菓類;乳酸菌飲料、粉末飲料などの飲料類; アイスクリーム、 シャ一ベッド、 氷菓、 ムース、 フローズンヨーグルトなどの冷 菓類;プリン、 ゼリー、 ババロア、 ヨーグルト、 クリームなどのデザート類;ス ープ、 カレー、 シチューなどの調理食品類;めんつゆ、 ドレッシング、 マヨネ一 ズ等の調味料類;パン、 ドーナツ等のベーカリー製品類;バタークリーム、 マー ガリンなどデイリー製品類;水産練り製品などを挙げることができる。  Examples of the above foods and drinks include confectionery products such as chocolate, gum, candy, potato chips, cookies, and biscuits; beverages such as lactic acid beverages and powdered beverages; ice creams, cherries, ice confectionery, mousse, frozen yogurt Frozen desserts; desserts such as pudding, jelly, bavarois, yogurt, cream; cooked foods such as soups, curries, stews; seasonings such as noodle soup, dressings, mayonnaise; And other daily products such as butter cream and margarine; fish paste products.
上記フレダランス製品としては、 香水、 オードトワレ、 オーデコロン、 シャヮ 一コロンなどを挙げることができる。  Examples of the above-mentioned Frederance products include perfume, eau de toilette, eau de cologne, and escologone.
上記基礎化粧品としては、 スキンクリーム、 クレンジングクリーム、 ナイトク リーム、 ハンドクリーム、 乳液、 化粧水、 アフターシェイブローション、 ボディ —ローション、 ファンデ一ション、 口紅、 リップクリーム、 タルカムパウダー、 シヮ防止化粧品、 老化防止化粧品、 サンケア製品、 マッサージオイルなどを挙げ ることができる。 上記頭髪化粧品としては、 シャンプー、 リンス、 コンディショナー、 リンスィ ンシャンプー、 トリートメントなどの洗髪剤;ポマード、 ヘアトニック、 ヘアリ キッド、 へアジエル、 ヘアクリーム、 へアム一スなどの整髪剤;育毛剤;染毛剤; コールドウェーブ剤などを挙げることができる。 The above basic cosmetics include skin creams, cleansing creams, night creams, hand creams, emulsions, lotions, after-shave lotions, body-lotions, foundations, lipsticks, lip balms, talcum powders, anti-aging cosmetics, anti-aging products Cosmetics, sun care products, massage oils, etc. can be mentioned. Examples of the above hair cosmetics include shampoos, rinses, conditioners, rinse-in shampoos, treatments, and other hair-washing agents; pomades, hair tonics, hair liquids, hair styling agents such as hair, hair creams, hair creams; Agents; cold wave agents and the like.
上記浴用剤としては、粉末入浴剤、固形入浴剤、固形発泡入浴剤、バスオイル、 バブルバスなどを挙げることができる。  Examples of the bath agent include a powder bath agent, a solid bath agent, a solid foaming bath agent, bath oil, a bubble bath, and the like.
上記トイレタリー製品としては、 化粧石鹼、 浴用石鹼、 透明石鹼などを挙げる ことができる。  Examples of the toiletry products include toilet stones, bath stones, and transparent stones.
上記洗剤としては、 衣類用粉末洗剤、 衣類用液体洗剤、 柔軟仕上げ剤、 台所用 洗剤、 トイレ用洗浄剤、 浴室用洗浄剤、 ガラスクリーナー、 カビ取り剤などを挙 げることができる。  Examples of the detergent include powder detergent for clothing, liquid detergent for clothing, fabric softener, kitchen detergent, toilet detergent, bathroom detergent, glass cleaner, mold remover and the like.
上記芳香消臭剤としては、 ゲル状芳香消臭剤、 液体芳香消臭剤、 含浸型エアゾ ール芳香消臭剤、 ミストタイプ芳香消臭剤などを挙げることができる。  Examples of the aromatic deodorant include a gel aromatic deodorant, a liquid aromatic deodorant, an impregnated aerosol aromatic deodorant, and a mist type aromatic deodorant.
上記医薬品としては、 膏薬、 軟膏、 座薬、 錠剤、 液状の薬、 カプセルタイプの 薬、 顆粒状の薬などを挙げることができる。 実施例  Examples of the pharmaceuticals include salves, ointments, suppositories, tablets, liquid medicines, capsule-type medicines, and granular medicines. Example
以下に実施例および比較例を挙げて本発明をさらに詳細に説明するが、 本発明 はこれらの実施例に限定されるものではない。  Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited to these Examples.
<サンプルの調製 > <Sample preparation>
サンプル 1 (シソ抽出物油溶画分)  Sample 1 (oil extract of perilla extract)
シソ葉'茎の乾燥物 1 0 0 gをミルで破片し、ソックスレー抽出器にセットし、 5 0 %含水エタノール 1 0 0 O m Lを加え、 室温で 8時間抽出した。 抽出液の濃 縮液を、 水—へキサン混合溶媒 (水一へキサン = 1 : 1容積比) 2 0 0 0 m Lで 室温下分配させた。 上記混合溶媒を 5 °Cで一晩放置し、 水画分を得た。 水画分を 濃縮乾固し、 シソ抽出物を得た。 ガスクロマトグラフィー法にて分析した残存シ ソ精油分は、 検出限界外であった。  100 g of dried perilla leaf's stem was broken into pieces with a mill, set in a Soxhlet extractor, added with 100% aqueous ethanol (50 mL), and extracted at room temperature for 8 hours. The concentrated solution of the extract was partitioned at room temperature with a water-hexane mixed solvent (water-hexane = 1: 1 volume ratio) of 2000 mL. The mixed solvent was left at 5 ° C overnight to obtain a water fraction. The water fraction was concentrated to dryness to obtain a perilla extract. The residual perilla essential oil analyzed by gas chromatography was outside the detection limit.
得られたシソ抽出物 1 gに、 ベンジルアルコールを加えて 1 0 0 gとした後、 5 0 °C、 3 0分間攪拌して溶解させた。 濾過により不溶物を除去してシソ抽出物 油溶性画分を得た。 サンプル 2 (ジャガイモ抽出物油溶画分) Benzyl alcohol was added to 1 g of the obtained perilla extract to make 100 g, and the mixture was dissolved by stirring at 50 ° C. for 30 minutes. Remove insolubles by filtration to extract perilla An oil-soluble fraction was obtained. Sample 2 (potato extract oil-soluble fraction)
ジャガイモ塊茎の乾燥物 1 0 0 gをミルで粉碎し、 エタノール 1 0 0 O m Lを 加えて、 3時間リフラックス抽出した。 得られた抽出物を濾過した後、 濾液部を 濃縮乾固し、 ジャガイモ抽出物を得た。  100 g of the dried potato tuber was ground with a mill, 100 mL of ethanol was added, and reflux extraction was performed for 3 hours. After the obtained extract was filtered, the filtrate was concentrated to dryness to obtain a potato extract.
得られたジャガイモ抽出物 1 gに、 ベンジルアルコールを加えて 1 0 0 gとし た後、 5 0 °C、 3 0分間攪拌して溶解させた。 濾過により不溶物を除去してジャ ガイモ抽出物油溶性画分を得た。 サンプル 3 (コーヒー抽出物油溶画分)  Benzyl alcohol was added to 1 g of the obtained potato extract to make 100 g, which was then dissolved by stirring at 50 ° C for 30 minutes. The insoluble matter was removed by filtration to obtain a potato extract oil-soluble fraction. Sample 3 (oil extract of coffee extract)
生コーヒー豆を粉砕機で粉砕後 (メッシュ 5 mm)、水を加えて 8 5〜9 5でで 2時間抽出した。 抽出液を濾過した後、 濾液部を濃縮乾固し、 コーヒー抽出物を 得た。  The green coffee beans were pulverized with a pulverizer (mesh 5 mm), added with water, and extracted with 85-95 for 2 hours. After the extract was filtered, the filtrate was concentrated to dryness to obtain a coffee extract.
得られたコ一ヒ一抽出物 1 gに、 ベンジルアルコールを加えて 1 0 0 とした 後、 5 0 ° (:、 3 0分間攪拌して溶解させた。 濾過により不溶物を除去してコ一ヒ 一抽出物油溶性画分を得た。 サンプル 4 (サツマィモ抽出物油溶画分)  Benzyl alcohol was added to 1 g of the obtained coffee extract to make it 100, and then dissolved by stirring at 50 ° (:, 30 minutes. Sample 4 (Satsumaimo extract oil-soluble fraction) was obtained.
サツマィモ類の葉茎及び根茎の乾燥物 1 0 0 gをミルで粉砕し、 エタノール 2 0 0 O m Lを加えて、 7 0〜7 5 °C、 4時間攪拌抽出した。 得られた抽出液を濾 過した後、 冷蔵下で一昼夜静置し、 再濾過してオリを除去した。 濾液部を濃縮乾 固し、 サツマィモ抽出物を得た。  100 g of dried leaves and rhizomes of sweet potatoes were pulverized with a mill, added with 200 mL of ethanol, and extracted with stirring at 70 to 75 ° C for 4 hours. After filtering the obtained extract, it was allowed to stand still in a refrigerator for a day and night, and re-filtered to remove the residue. The filtrate was concentrated to dryness to obtain a sweet potato extract.
得られたサッマイモ抽出物 1 gに、 ベンジルアルコールを加えて 1 0 0 gとし た後、 5 0 ° (、 3 0分間攪拌して溶解させた。 濾過により不溶物を除去してサッ マイモ抽出物油溶性画分を得た。 サンプル 5 (リンゴ果皮抽出物油溶画分)  Benzyl alcohol was added to 1 g of the obtained sweet potato extract to make 100 g, and then dissolved by stirring at 50 ° (30 minutes. Insoluble matter was removed by filtration to remove the sweet potato extract. Sample 5 (oil extract of apple peel extract)
リンゴ (品種ふじ) 果皮乾燥物をミルで粉碎し、 粉末化し、 リンゴパウダー 1 O O gを得た。 そのパウダー 8 0 gに、 水 8 0 0 m Lを加えて、 3時間、 リフラ ックス抽出した。 抽出液を濾過した後濾過液を濃縮乾固し、 リンゴ果皮抽出物を 得た。 Apple (Cultivar Fuji) Dried pericarp is crushed with a mill, pulverized, and apple powder 1 OO g was obtained. To 800 g of the powder, 800 mL of water was added, and reflux extraction was performed for 3 hours. After the extract was filtered, the filtrate was concentrated to dryness to obtain an apple peel extract.
得られたリンゴ果皮抽出物 1 gに、 ベンジルアルコールを加えて 1 0 0 gとし た後、 5 0 °C、 3 0分間攪拌して溶解させた。 濾過により不純物を除去してリン ゴ果皮抽出物油溶性画分を得た。 サンプル 6 (バナナ抽出物油溶画分)  Benzyl alcohol was added to 1 g of the obtained apple peel extract to make 100 g, and the mixture was dissolved by stirring at 50 ° C for 30 minutes. The impurities were removed by filtration to obtain an oil-soluble fraction of the apple peel extract. Sample 6 (banana extract oil fraction)
バナナ全果にエタノールを加えた後、 7 0 °C、 2時間攙拌抽出した。 抽出液を 濾過した後、 濾過液を減圧下、 乾固濃縮してバナナ抽出物を得た。  After adding ethanol to all the banana fruits, extraction was carried out by stirring at 70 ° C. for 2 hours. After the extract was filtered, the filtrate was concentrated to dryness under reduced pressure to obtain a banana extract.
得られたバナナ抽出物 1 gに、ベンジルアルコールを加えて 1 0 0 gとした後、 5 0 °C、 3 0分間攙拌して溶解させた。 濾過により不純物を除去してバナナ抽出 物油溶性画分を得た。 サンプル 7 (ブドウ果実抽出物油溶画分)  Benzyl alcohol was added to 1 g of the obtained banana extract to make 100 g, and the mixture was stirred at 50 ° C. for 30 minutes to be dissolved. The impurities were removed by filtration to obtain an oil-soluble fraction of the banana extract. Sample 7 (Grape fruit extract oil fraction)
ブドウ果皮 (品種:キャンベル種) にエタノールを加えた後、 7 0 °C、 2時間 攪拌抽出した。 抽出液を濾過した後、 濾過液を減圧下、 乾固濃縮してブドウ果皮 抽出物を得た。  After ethanol was added to the grape skin (cultivar: Campbell varieties), the mixture was stirred and extracted at 70 ° C for 2 hours. After the extract was filtered, the filtrate was concentrated to dryness under reduced pressure to obtain a grape skin extract.
得られたブドウ果皮抽出物 1 gに、 ベンジルアルコールを加えて 1 0 0 gとし た後、 5 0 °C、 3 0分間攪拌して溶解させた。 濾過により不純物を除去してブド ゥ果皮抽出物油溶性画分を得た。 サンプル 8 (ブドウ種子抽出物油溶画分)  Benzyl alcohol was added to 1 g of the obtained grape skin extract to make 100 g, which was then dissolved by stirring at 50 ° C for 30 minutes. The impurities were removed by filtration to obtain an oil-soluble fraction of the perilla extract. Sample 8 (Grape seed extract oil-soluble fraction)
ブドウ種子抽出物 (キッコーマン㈱製) 1 gに、 ベンジルアルコールを加えて 1 0 0 gとした後、 5 0 °C、 3 0分間攪拌して溶解させた。 濾過により不純物を 除去してブドウ種子抽出物油溶性画分を得た。 サンプル 9 (ゴボウ抽出物油溶画分)  Benzyl alcohol was added to 1 g of grape seed extract (manufactured by Kikkoman Co., Ltd.) to make 100 g, which was then dissolved by stirring at 50 ° C. for 30 minutes. The impurities were removed by filtration to obtain a grape seed extract oil-soluble fraction. Sample 9 (burdock extract oil fraction)
ゴポゥをミルで粉砕し、 エタノールを加えて 2時間リフラックス抽出した。 抽 出液を濾過した後濾過液を濃縮乾固し、 ゴボウ抽出物を得た。 Gopo was pulverized with a mill, and ethanol was added thereto for 2 hours of reflux extraction. Lottery After the filtrate was filtered, the filtrate was concentrated to dryness to obtain a burdock extract.
得られたゴポゥ抽出物 1 gに、ベンジルアルコールを加えて 1 0 0 gとした後、 5 0 °C、 3 0分間攪拌して溶解させた。 濾過により不純物を除去してゴボウ抽出 物油溶性画分を得た。 サンプル 1 0 (マジョラム抽出物油溶画分)  Benzyl alcohol was added to 1 g of the obtained Gopo extract to make 100 g, and the mixture was dissolved by stirring at 50 ° C for 30 minutes. The impurities were removed by filtration to obtain a burdock extract oil-soluble fraction. Sample 10 (marjoram extract oil fraction)
マジョラム乾燥物 1 k gに、水 2 0 Lを加えて、 4 、 2時間攪拌抽出した。 抽出液を濾過した後濾過液を濃縮乾固し、 マジョラム抽出物を得た。  To 1 kg of the dried marjoram, 20 L of water was added, and the mixture was extracted with stirring for 4.2 hours. After filtering the extract, the filtrate was concentrated to dryness to obtain a marjoram extract.
得られたマジョラム抽出物 1 gに、 ベンジルアルコールを加えて 1 0 0 gとし た後、 5 0 °C、 3 0分間攪拌して溶解させた。 濾過により不純物を除去してマジ ョラム抽出物油溶性画分を得た。 サンプル 1 1 (ヒマヮリ種子抽出物油溶画分)  Benzyl alcohol was added to 1 g of the obtained marjoram extract to make 100 g, and the mixture was stirred and dissolved at 50 ° C for 30 minutes. The impurities were removed by filtration to obtain an oil-soluble fraction of marjoram extract. Sample 1 1 (oil fraction of castor seed extract)
市販のヒマヮリ種子抽出物 (大日本インキ㈱製) l gに、 ベンジルアルコール を加えて 1 0 0 gとした後、 5 0 t:、 3 0分間攪拌して溶解させた。 濾過により 不純物を除去してヒマヮリ種子抽出物油溶性画分を得た。 サンプル 1 2 (ローズマリ一抽出物油溶画分)  To 1 g of a commercially available sunflower seed extract (manufactured by Dainippon Ink and Chemicals, Inc.) was added 100 g of benzyl alcohol, and the mixture was dissolved by stirring at 50 t: for 30 minutes. The impurities were removed by filtration to obtain an oil-soluble fraction of the castor seed extract. Sample 1 2 (Rose Mali extract oil-soluble fraction)
市販のローズマリー抽出物 (東京田辺製薬㈱製) l gに、 ベンジルアルコール を加えて 1 0 0 gとした後、 5 0 °C、 3 0分間攪拌して溶解させた。 濾過により 不純物を除去してローズマリー抽出物油溶性画分を得た。 サンプル 1 3 (ペパーミント抽出物油溶性画分)  To 1 g of commercially available rosemary extract (manufactured by Tokyo Tanabe Seiyaku Co., Ltd.) was added 100 g of benzyl alcohol, and the mixture was dissolved by stirring at 50 ° C. for 30 minutes. The impurities were removed by filtration to obtain an oil-soluble fraction of the rosemary extract. Sample 1 3 (oil-soluble fraction of peppermint extract)
水蒸気蒸留によりオイルを回収した後のペパーミント乾燥葉 2 5 0 gをミルで 粉碎し、 蒸留水 3 0 0 O mLを加えて、 2時間リフラックス抽出した。 得られた 抽出物を濾過した後、 濾液部を濃縮乾固し、 ペパーミント抽出物を得た。 得ら れたぺパ一ミント抽出物 1 gに、ベンジルアルコールを加えて 1 0 0 gとした後、 5 0 °C、 3 0分間攪拌して溶解させた。 濾過により不溶物を除去してペパーミン ト抽出物油溶性画分を得た。 トコフエロール溶液の調製 250 g of dried peppermint leaves after recovering the oil by steam distillation were ground with a mill, and 300 O mL of distilled water was added thereto, followed by reflux extraction for 2 hours. After filtering the obtained extract, the filtrate was concentrated to dryness to obtain a peppermint extract. Benzyl alcohol was added to 1 g of the obtained peppermint extract to make 100 g, and the mixture was dissolved by stirring at 50 ° C. for 30 minutes. The insoluble matter was removed by filtration to obtain a peppermint extract oil-soluble fraction. Preparation of tocopherol solution
トコフエロール (ナカライテスク社製) 1 gに、 ベンジルアルコールを加えて 1 0 0 gとして溶解させ、 トコフエ口一ル溶液とした。 ァスコルビン酸エステル溶液の調製  Tocopherol (manufactured by Nacalai Tesque, Inc.) (1 g) was added with benzyl alcohol and dissolved to 100 g to give a tocopher solution. Preparation of ascorbic acid ester solution
ァスコルビン酸エステル 1 gに、 ベンジルアルコールを加えて 1 0 0 gとして 溶解させ、 ァスコルビン酸エステル溶液とした。 <試験例 1 >  Benzyl alcohol was added to 1 g of ascorbic acid ester to make 100 g and dissolved to obtain an ascorbic acid ester solution. <Test Example 1>
得られた各種サンプルと、 トコフエロール溶液、 ァスコルビン酸エステル溶液 を表 1記載の配合比(wZw)に従って配合した抗酸化組成物(実施例 1〜 3 5 , 比較例 1〜2 0 ) を作製した。 得られた各抗酸化組成物について、 下記の条件で 自動酸化による安定化試験を行い、 その結果をトコフエロール単体の場合との比 較で、 表 1に示した。 自動酸化による安定化試験  Antioxidant compositions (Examples 1 to 35 and Comparative Examples 1 to 20) were prepared by blending the obtained various samples, the tocopherol solution, and the ascorbic acid ester solution according to the blending ratio (wZw) shown in Table 1. For each of the obtained antioxidant compositions, a stabilization test was performed by autoxidation under the following conditions, and the results are shown in Table 1 in comparison with the case of tocopherol alone. Stabilization test by autoxidation
試験方法: 「油化学第 4 2巻第 6号 (1 9 9 3 )、 2 . 4 . 2 8 . 2— 9 3」 に 準じた方法 (ランシマット法) で、 酸化により生成された揮発性の分解生成物を 水中に捕集させ、 その導電率が急激に変化する折曲点までの時間を測定すること によって安定性を確認した。  Test method: Volatility generated by oxidation according to the method (Rancimat method) according to “Oil Chemistry Vol. 42, No. 6 (1993), 2.4.28.2-93” Decomposition products were collected in water, and the stability was confirmed by measuring the time until the bending point where the conductivity changed abruptly.
測定条件 温度: 1 2 0 、 空気流量: 2 0 L / h r  Measurement conditions Temperature: 120, Air flow: 20 L / hr
サンプル添加方法:各 1 %ベンジルアルコールを表 1記載の配合比に従って配 合し、 計 1 gになるようにしたものを、 予め消泡シリコンを 0 . 0 2 5 %懸濁し たラッカセィ油 4 gに添加した。 表 1 Sample addition method: 1 g benzyl alcohol was mixed according to the mixing ratio shown in Table 1 to make a total of 1 g, and 4 g of laccase oil in which 0.025% of defoamed silicon was suspended in advance. Was added. table 1
Θ己合比 Induction time 比 , . ■ .__ ·置、 Induction time ratio,. ■ .__
(サンフル:トコフェロール (^rトコノエロール単体) 卜コフェローレ 0:10 1.00  (Sanfur: Tocopherol (^ r Toconoerol only) Tocopherol 0:10 1.00
溶液  Solution
比較例 1 サンプル 1 10:0 0.85 実施例 1 8:2 1.77 実施例 2 5:5 2. 26 実施例 3 2:8 2.25 比較例 2 サンプル 2 10:0 0. 26 実施例 4 8:2 0.82 実施例 5 5:5 1.54 実施例 6 2:8 1. 16 比車父例 3 サンプル 3 10:0 0.74 実施例 7 8:2 1.56 実施例 8 5:5 1.84 実施例 9 2:8 1.75 比較例 4 サンプル 4 10:0 0.63 実施例 10 8:2 1. 12 実施例 11 5:5 1.63 実施例 12 2:8 1.38 Comparative Example 1 Sample 1 10: 0 0.85 Example 1 8: 2 1.77 Example 2 5: 5 2.26 Example 3 2: 8 2.25 Comparative Example 2 Sample 2 10: 0 0.26 Example 4 8: 2 0.82 Example 5 5: 5 1.54 Example 6 2: 8 1.16 Comparative Example 3 Sample 3 10: 0 0.74 Example 7 8: 2 1.56 Example 8 5: 5 1.84 Example 9 2: 8 1.75 Comparative Example 4 Sample 4 10: 0 0.63 Example 10 8: 2 1.12 Example 11 5: 5 1.63 Example 12 2: 8 1.38
 "
比單父 i例ni — 比 独 Father i ex ni —
5 サンス レ 5 10:0 0.43 実施例 13 8:2 1. 28 実施例 14 5:5 1.74 実施例 15 2:8 1.39 比較例 6 サンプル 6 10:0 0.38 実施例 16 8:2 1.52 芙施 1列 17 o: o . bo 美 BS1タ1 Π 8 Z: o ,, / / 比軍 7 サンノレ 7 10:0 0.44 夷施例 19 : 2 I . i b 施例 20 5: 5 5 Sensure 5 10: 0 0.43 Example 13 8: 2 1.28 Example 14 5: 5 1.74 Example 15 2: 8 1.39 Comparative Example 6 Sample 6 10: 0 0.38 Example 16 8: 2 1.52 Fuse 1 row 17 o: o. Bo Beauty BS1 1 8 : Z: o ,, // Higun 7 Sannore 7 10: 0 0.44 Inhibit 19: 2 I.ib Invest 20 5: 5
施例 21 2: 8 1. 25 比車父例 8 サンノレ 8 10:0 0.68 夹她例 22 8: 2 1 · 21 施例 23 5: 5 1.45 施例 24 2:8 1.39 比早父例 9 サンフル 9 10:0 0.73 実施例 25 8: 2 1.51 臾 SI例 26 5: 5 1.92 実 S¾l例 27 2:8 1.65 比車父例 10 サノフル 10 10:0  Example 21 2: 8 1.25 Hibiki father 8 Sannore 8 10: 0 0.68 夹 她 Example 22 8: 2 1 · 21 Example 23 5: 5 1.45 Example 24 2: 8 1.39 9 10: 0 0.73 Example 25 8: 2 1.51 Hook SI example 26 5: 5 1.92 Real S¾l example 27 2: 8 1.65
夹カ ffi例 28 8: 2 6 1.56 施例 29 ο:5 1.8寸9 夷施例 30 2:8 1.75 比早父例 11 サンブル 11 10:0 0.74夹 カ ffi 例 28 8 : 2 6 1.56 Example 29 ο: 5 1.8 Dimensions 9 Inhibit Example 30 2: 8 1.75 Hihaya Father 11 Samburu 11 10: 0 0.74
^:施例 31 8: 2 1.21 夷施例 32 5:5 1.83 夷她例 33 2:8 1.65 比 ¥父例" 12 サンフゾレ 12 10:0 0.53 比早父例 13 8: 2 0.78^: Example 31 8: 2 1.21 Example of Inhibition 32 5: 5 1.83 Example of Inhibition 33 2: 8 1.65 Compared to Father "12 Sanfuzore 12 10: 0 0.53
£じ卑父 1タリ 14 : 1. 12 比較例 15 2:8 1.06 比較例 16 サンプル 13 10:0 0. 17 比較例 17 8:2 0.52 比較 rfrit例 18 5:5 £ 1 per month 14: 1.12 Comparative example 15 2: 8 1.06 Comparative example 16 Sample 13 10: 0 0.17 Comparative example 17 8: 2 0.52 Comparative rfrit example 18 5: 5
比較例 19 2: 8 0.63  Comparative Example 19 2: 8 0.63
酉己合八比 Induction time 比  Inori time ratio
(サンノ レ:卜コフエ口一 レ: (对卜コフエ口一 レ単 1本ノ (Sanno Re: Ukkou Fuchi Ichi Re: (对 Ukko Fue Kichiichi Re 1 Single
/ Λコ レヒノ @Sエス丁ノレ) / ΛKo Lehino
比較例 20 サンプル 1 0:2:1 1.06  Comparative Example 20 Sample 1 0: 2: 1 1.06
実施例 34 2:2:1 3.08  Example 34 2: 2: 1 3.08
実施例 35 1 :1 :1 2.93  Example 35 1: 1: 1 2.93
induction time:  induction time:
油脂の酸化分解により生じた揮発性分解生成物(大部分がギ酸)を純水中に捕集し、その導 電率を自動的にプロットした誘導曲線における、導電率が急激に変化する変曲点までの時 間。 Induction timeが長いものほど油脂の酸化劣化が抑制されているとみる。 表 1から、 トコフエロールとの相乗効果がみられたのは、 サンプル 1とトコフ エロールを組み合わせた実施例 1 3、 サンプル 2とトコフエロールを組み合わ せた実施例 4 6、 サンプル 3とトコフエロールを組み合わせ〇た実施例 7 9 サンプル 4とトコフエロールを組み合わせた実施例 10 12、 サ卜 Volatile decomposition products (mostly formic acid) generated by the oxidative decomposition of fats and oils are collected in pure water, and the conductivity is plotted automatically. Time to point. It is considered that the longer the induction time, the more the oxidative deterioration of fats and oils is suppressed. From Table 1, the synergistic effect with tocopherol was observed in Examples 13 and 13 in which sample 1 and tocopherol were combined, Examples 4 and 6 in which sample 2 was combined with tocopherol, and combination of sample 3 and tocopherol. Example 7 9 Example 10 12 combining sample 4 and tocopherol
0 0ンプル 5とト コフエロールを組み合わせた実施例 13 1 5、 サンプル 6とトコフエロールを 組み合わせた実施例 16 18、 サンプル 7とトコフエロールを組み合わせた実 施例 1 9 21、サンプル 8とトコフエロールを組み合わせた実施例 22-24, サンプル 9とトコフエロールを組み合わせた実施例 25 27、 サンプル 10と トコフエロールを組み合わせた実施例 28 30、 サンプル 1 1とトコフエ口一 ルを組み合わせた実施例 3 1 33で、 トコフエロール単体の場合よりもラッカ セィ油の酸化劣化が顕著に抑制されることが明らかになった。 また、 サンプル 1 2とトコフエロールを組み合わせた比較例 12 1 5では、 多少の相乗効果は認 められるものの、 サンプル 1 1 1とトコフエ口 ルの各組み合わせに比べ充分 な効果ではなかった。 サンプル 13とトコフエロールを組み合わせた比較例 1 6 1 9では、 トコフエロール単独の場合のほうが優れた酸化抑制効果を示した。 また、 サンプル 1と、 トコフエロール及びァスコルビン酸エステルとを組み合わ せた実施例 3 4及び 3 5で、 トコフエロール単体の場合に比べてラッカセィ油の 酸化劣化がさらに顕著に抑制されることが明らかになった。 0 0 Example 5 with sample 5 combined with tocopherol 13 15 Example with sample 6 combined with tocopherol 16 18, Example with sample 7 combined with tocopherol 1 9 21, Example 8 with sample 8 combined with tocopherol Example 22-24, Example 25 27 combining sample 9 with tocopherol, Example 28 30 combining sample 10 with tocopherol, Example 3 1 33 combining sample 11 with tocopherol, It became clear that the oxidative degradation of laccase oil was suppressed more than in the case. In Comparative Example 12 15 in which Sample 12 and Tocopherol were combined, although a certain synergistic effect was observed, the effect was not sufficient compared to each combination of Sample 11 and Tocopherol. In Comparative Example 16 19, in which Sample 13 and Tocopherol were combined, the case of Tocopherol alone showed a superior oxidation inhibitory effect. Sample 1 was combined with tocopherol and ascorbate. In Examples 34 and 35, the oxidative deterioration of laccase oil was more remarkably suppressed as compared with the case of tocopherol alone.
<試験例 2 > <Test Example 2>
つぎに、 サンプル 1とトコフエロール溶液を表 2記載の配合比 (wZw) に従 つて配合した抗酸化組成物を調製し、 これを表 2記載の添加量でラッカセィ油 4 gに添加したものの酸化安定性を調べた。 試験方法、 測定条件は試験例 1のとお りである。 結果を表 2に示す。 表 2  Next, an antioxidant composition was prepared by blending Sample 1 and the tocopherol solution according to the blending ratio (wZw) shown in Table 2, and this was added to 4 g of laccase oil in the amount shown in Table 2 to achieve oxidation stability. The sex was examined. The test method and measurement conditions are as in Test Example 1. Table 2 shows the results. Table 2
Figure imgf000026_0001
Figure imgf000026_0001
* )ベンジルアルコールのみ 1 gをラッカセィ油に添加 表 2から、 本発明にかかる抗酸化組成物において、 その添加量をトコフェロー ル単独の場合より低減させても充分な抗酸化能を奏することが明らかになり、 ト コフエロール単体の場合のわずか 1 0分の 1程度の量で、 トコフエロール単体の 場合と同等レベルの効果を得られることがわかった。  *) Addition of only 1 g of benzyl alcohol to laccase oil From Table 2, it can be seen that the antioxidant composition according to the present invention can exhibit sufficient antioxidant ability even when the amount of addition is smaller than that of tocopherol alone. It became clear that only about one-tenth the amount of tocopherol alone can achieve the same level of effect as tocopherol alone.
<試験例 3 > <Test Example 3>
サンプル 1とトコフェロール溶液を表 3記載の配合比 (wZw) に従って配合 した抗酸化組成物を調製し、 各抗酸化組成物 1 gを各動植物油 4 gに添加したも のの酸化安定性を調べた。 劣化の度合いは評点指標に従って専門パネラー 5名に よる官能検査により評価した。 結果を表 3に示す。 評点指標) An antioxidant composition was prepared by mixing Sample 1 and the tocopherol solution according to the mixing ratio (wZw) shown in Table 3, and 1 g of each antioxidant composition was added to 4 g of each animal and vegetable oil. Was examined for its oxidative stability. The degree of deterioration was evaluated by a sensory test conducted by five expert panelists according to the score index. Table 3 shows the results. Score index)
1:油脂の劣化臭を著しく強く感じる  1: Feel the deterioration odor of fats and oils extremely strong
2:油脂の劣化臭を強く感じる  2: Deterioration smell of fats and oils is strongly felt
3:油脂の劣化臭を感じる  3: Feel the deterioration odor of fats and oils
:油脂の劣化臭をわずかに感じる  : Slightly deteriorating odor of fats and oils
5:油脂の劣化臭を感じない  5: No deterioration odor of fats and oils is felt
表 3 動植物油 配合比 官能評価の平均値 Table 3 Animal and vegetable oil blending ratio Average value of sensory evaluation
(サンプル 1:卜コフ: I:ロール溶液)  (Sample 1: Torkov: I: Roll solution)
ラッカセィ油 0:0* 1.4  Peanut oil 0: 0 * 1.4
0:10 2.8  0:10 2.8
10:0 2.0  10: 0 2.0
5:5 4.0  5: 5 4.0
アーモンド油 0:0* 1.6  Almond oil 0: 0 * 1.6
0:10 2.8  0:10 2.8
10:0 2. 2  10: 0 2.2
5:5 4.0  5: 5 4.0
マカデミアナッツ油 0:0* 1. 8  Macadamia nut oil 0: 0 * 1.8
0:10 3.0  0:10 3.0
10:0 2. 2  10: 0 2.2
5:5 4. 2
Figure imgf000028_0001
5: 5 4.2
Figure imgf000028_0001
*)ベンジルアルコールのみ 1 gを各動植物油に添加 表 3から、 サンプル 1とトコフエロールを組み合わせた抗酸化組成物を添加す ることにより、 トコフエロ一ル単体の場合よりも各動植物油の酸化劣化が抑制さ れ、 トコフエロール特有の嫌臭を効果的に抑えることができることが明らかにな つた。  *) Only 1 g of benzyl alcohol was added to each animal and vegetable oil.From Table 3, adding the antioxidant composition combining sample 1 and tocopherol reduced the oxidative degradation of each animal and vegetable oil compared to the case of tocopherol alone. It was clear that the odor characteristic of tocopherol can be suppressed effectively.
<処方例 1 > <Prescription example 1>
下記のような処方で本発明の抗酸化組成物を含むバターフレーバーを調製した c バターフレーパー C butter flavour prepared with a butter flavor containing the antioxidant composition of the present invention in the following formulation
バター香料 40. 00  Butter flavor 40.00
エステル類 0. 10  Esters 0.10
ケトン類 0. 70  Ketones 0.70
脂肪酸類 2. 60  Fatty acids 2.60
トコフエロール 0. 05  Tocopherols 0.05
シソ抽出物油溶画分 0. 05 ラッカセィ油 56. 50 Perilla extract oil-soluble fraction 0.05 Peanut oil 56.50
1 00. 00重量%  1 00.00% by weight
<処方例 2 > <Prescription example 2>
常法通り、 下記に示す原料を混合、 攪拌し、 その生地に処方例 1のバターフレ ーバ一を 0. 2重量%添加し、 適度な大きさに分割後、 成形し、 オーブンで 1 8 5 、 12分焼成してソフトビスケットを調製した。 ソフトビスケット処方  Mix and stir the following ingredients as usual, add the butter flavor of Formulation Example 1 to the dough in an amount of 0.2% by weight, divide it into appropriate sizes, mold, and form in an oven. The mixture was baked for 12 minutes to prepare a soft biscuit. Soft biscuit prescription
薄力粉 44. 8  Soft flour 44. 8
ショートニング 24. 0  Shortening 24.0
粉糖 21. 0  Powdered sugar 21.0
脱脂粉乳 3. 7  Nonfat dry milk 3.7
全卵 6. 0  Whole egg 6.0
食塩 0. 2  Salt 0.2
炭酸水素アンモニゥム 0. 2  Ammonium bicarbonate 0.2
炭酸水素ナトリウム — 0. _1_  Sodium bicarbonate — 0. _1_
100. 0重量%  100.0% by weight
<処方例 3 > <Prescription example 3>
下記のような処方で本発明の抗酸化組成物を含むバニラフレーバーを調製した < バニラフレーバー  A vanilla flavor containing the antioxidant composition of the present invention was prepared according to the following formulation.
バニリン 2. 00  Vanillin 2.00
トコフエロール 0. 20  Tocopherols 0.20
ジャガイモ抽出物油溶画分 0. 05  Potato extract oil-soluble fraction 0.05
キヤノ一ラ油 (菜種油の 1種) _97. 75  Canola oil (a type of rapeseed oil) _97. 75
100. 00重量% <処方例 4> 100.00% by weight <Prescription example 4>
処方例 3に示すバニラフレーバーをチョコレート生地に 0.05〜0.2重量% 練りこみ、 チョコレートを調製した。  The vanilla flavor shown in Formulation Example 3 was kneaded into chocolate dough at 0.05 to 0.2% by weight to prepare chocolate.
<処方例 5 > <Prescription example 5>
下記に示す配合量にしたがって、 フードプロセッサ一を用いて乾燥落花生を粉 砕した後、 バターを加えてよく混ぜた。 そこへ、 メ一プルシロップ、 サツマィモ 抽出物油溶画分、 トコフェロールを加えてよく混ぜ、 本発明の抗酸化組成物を含 むピーナッツバターを調製した。 ピー'  The dried peanuts were ground using a food processor according to the amounts shown below, and then butter was added and mixed well. Thereto, maple syrup, oil extract of sweet potato extract and tocopherol were added and mixed well to prepare a peanut butter containing the antioxidant composition of the present invention. P '
乾燥落花生 100. 00  Dried peanuts 100.00
バター 25. 00  Butter 25.00
メ一プルシロップ 20. 00  Maple syrup 20.00
トコフエロール 0. 14  Tocopherols 0.14
サツマィモ抽出物油溶画分 0. 14  Oil extract of sweet potato extract 0.14
145. 28 g <処方例 6 >  145.28 g <Formulation Example 6>
下記のような処方で、本発明の抗酸化組成物を含むサンドクリームを調製した サンドクリーム  Sand cream containing the antioxidant composition of the present invention was prepared according to the following formulation.
ショー卜ニング 40. 00  Shortening 40.00
脱脂粉乳 16. 00  Skim milk powder 16.00
トコフエロール 0. 04  Tocopherols 0.04
バナナ抽出物油溶画分 0. 04  Banana extract oil fraction 0.04
―粉糖 43. 92  ― Powdered sugar 43.92
100. 00重量% 産業上の利用可能性 100.00% by weight Industrial applicability
本発明の抗酸化組成物は、例えば、動植物油;各種飲食品;フ 品, 基礎化粧品、 頭髪化粧品、 浴用剤等の香粧品; トイレタリー製品、 洗剤 ·仕上げ 剤、 芳香消臭剤等の家庭用品;医薬品等に有用な抗酸化剤として利用される。  The antioxidant composition of the present invention includes, for example, animal and vegetable oils; various foods and beverages; cosmetics such as foods, basic cosmetics, hair cosmetics, bath preparations; household goods such as toiletry products, detergents and finishing agents, and aromatic deodorants. Used as a useful antioxidant for pharmaceuticals and the like.

Claims

請 求 の 範 囲 The scope of the claims
1 . (a) ジャガイモ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベン ジルアルコール、 酢酸ェチル、 石油ェ一テル、 グリセロール、 モノグリセリド、 ジグリセリド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によつ て抽出したジャガイモ抽出物油溶画分; 1. (a) Potato extract is soluble in at least one oil selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils. Potato extract oil-soluble fraction extracted with solvent;
サッマイモ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たサッマイモ抽出物油溶画分;  The sweet potato extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction;
コーヒー抽出物を、 低級アルコール、 ポリオ一ル系有機溶媒、 ベンジルアルコ ール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリ ド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出した コーヒー抽出物油溶画分;  Extract coffee extract with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Oil extract of coffee extract;
シソ精油の含有量が 1重量%以下であるシソ抽出物を、 低級アルコール、 ポリ オール系有機溶媒、 ベンジルアルコール、 酢酸ェチル、 石油エーテル、 グリセ口 ール、 モノグリセリド、 ジグリセリド及び動植物油からなる群より選ばれる 1種 以上の油溶性溶媒によって抽出したシソ抽出物油溶画分;  A perilla extract having a perilla essential oil content of 1% by weight or less is selected from the group consisting of lower alcohols, polyol-based organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Perilla extract oil-soluble fraction extracted with one or more selected oil-soluble solvents;
リンゴ抽出物を、 低級アルコール、 ポリオ一ル系有機溶媒、 ベンジルアルコ一 ル、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したリ ンゴ抽出物油溶画分;  The apple extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Oil extract of lingo extract;
バナナ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコー ル、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したバ ナナ抽出物油溶画分;  Banana extract extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Oil-soluble fraction;
ブドウ果皮抽出物を、 低級アルコール、 ポリオ一ル系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセ口一ル、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たブドウ果皮抽出物油溶画分; The grape skin extract is made of one or more oil-soluble compounds selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extracted by solvent Grape peel extract oil fraction;
ブドウ種子抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たブドウ種子抽出物油溶画分;  Grape seed extract was extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Grape seed extract oil fraction;
ゴポゥ抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアルコ一 ル、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセリド 及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出したゴ ボウ抽出物油溶画分;  Gobo extract is extracted with at least one oil-soluble solvent selected from the group consisting of lower alcohol, polyol organic solvent, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglyceride, diglyceride, and animal and vegetable oils. Extract oil-soluble fraction;
マジョラム抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルアル コール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリセ リド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出し たマジョラム抽出物油溶画分;並びに  Marjoram extract is extracted with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils. Extract oil-soluble fraction; and
ヒマヮリ種子抽出物を、 低級アルコール、 ポリオール系有機溶媒、 ベンジルァ ルコール、 酢酸ェチル、 石油エーテル、 グリセロール、 モノグリセリド、 ジグリ セリド及び動植物油からなる群より選ばれる 1種以上の油溶性溶媒によって抽出 したヒマヮリ種子抽出物油溶画分;  Sunflower seed extracted from sunflower seed extract with one or more oil-soluble solvents selected from the group consisting of lower alcohols, polyol organic solvents, benzyl alcohol, ethyl acetate, petroleum ether, glycerol, monoglycerides, diglycerides, and animal and vegetable oils Extract oil-soluble fraction;
からなる群より選ばれる 1種以上の抽出物油溶画分と、  One or more oil extract fractions selected from the group consisting of:
(b) トコフエロール、 ァスコルビン酸エステル、 )3 -カロチン、 及びリコピンから なる群から選ばれる 1種以上と (b) at least one selected from the group consisting of tocopherol, ascorbate,) 3-carotene, and lycopene
を含有する抗酸化組成物。 An antioxidant composition containing
2 . 特許請求の範囲第 1項に記載の抗酸化組成物を含むことを特徴とする動植 物油。 2. A plant and animal oil comprising the antioxidant composition according to claim 1.
3 . 特許請求の範囲第 2項に記載の動植物油を含むことを特徴とする飲食品。 3. A food or drink comprising the animal or vegetable oil according to claim 2.
4 . 特許請求の範囲第 2項に記載の動植物油を含むことを特徴とする医薬品。 4. A pharmaceutical product comprising the animal or vegetable oil according to claim 2.
5 . 特許請求の範囲第 2項に記載の動植物油を含むことを特徴とする香粧品。 5. A cosmetic product comprising the animal or vegetable oil according to claim 2.
6 . 特許請求の範囲第 2項に記載の動植物油を含むことを特徴とする家庭用品 7 . 特許請求の範囲第 1項に記載の抗酸化組成物を動植物油に添加することに より、 その動植物油に抗酸化能を付与する方法。 6. Houseware characterized by containing the animal and vegetable oil according to claim 2 7. The antioxidant composition according to claim 1 is added to the animal and vegetable oil to A method for imparting antioxidant ability to animal and vegetable oils.
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