WO2022131656A1 - Composition émulsifiée soluble dans l'eau contenant un alcaloïde - Google Patents

Composition émulsifiée soluble dans l'eau contenant un alcaloïde Download PDF

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Publication number
WO2022131656A1
WO2022131656A1 PCT/KR2021/018432 KR2021018432W WO2022131656A1 WO 2022131656 A1 WO2022131656 A1 WO 2022131656A1 KR 2021018432 W KR2021018432 W KR 2021018432W WO 2022131656 A1 WO2022131656 A1 WO 2022131656A1
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Prior art keywords
water
weight
emulsion
alkaloid
soluble
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PCT/KR2021/018432
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English (en)
Korean (ko)
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윤관식
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윤관식
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Priority claimed from KR1020200174987A external-priority patent/KR102524312B1/ko
Priority claimed from KR1020210026166A external-priority patent/KR20220122840A/ko
Application filed by 윤관식 filed Critical 윤관식
Publication of WO2022131656A1 publication Critical patent/WO2022131656A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/005—Edible oil or fat compositions containing an aqueous phase, e.g. margarines characterised by ingredients other than fatty acid triglycerides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D7/00—Edible oil or fat compositions containing an aqueous phase, e.g. margarines
    • A23D7/01—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/007—Other edible oils or fats, e.g. shortenings, cooking oils characterised by ingredients other than fatty acid triglycerides
    • A23D9/013—Other fatty acid esters, e.g. phosphatides
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23D—EDIBLE OILS OR FATS, e.g. MARGARINES, SHORTENINGS, COOKING OILS
    • A23D9/00—Other edible oils or fats, e.g. shortenings, cooking oils
    • A23D9/06—Preservation of finished products
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23K—FODDER
    • A23K20/00—Accessory food factors for animal feeding-stuffs
    • A23K20/10—Organic substances
    • A23K20/158—Fatty acids; Fats; Products containing oils or fats
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/15—Vitamins
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/10—Alcohols; Phenols; Salts thereof, e.g. glycerol; Polyethylene glycols [PEG]; Poloxamers; PEG/POE alkyl ethers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/08—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing oxygen, e.g. ethers, acetals, ketones, quinones, aldehydes, peroxides
    • A61K47/14—Esters of carboxylic acids, e.g. fatty acid monoglycerides, medium-chain triglycerides, parabens or PEG fatty acid esters
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/46—Ingredients of undetermined constitution or reaction products thereof, e.g. skin, bone, milk, cotton fibre, eggshell, oxgall or plant extracts

Definitions

  • the present invention relates to an alkaloid-containing water-soluble emulsion composition containing a water-soluble antioxidant emulsion.
  • Alkaloids are basic compounds containing nitrogen, and are a generic term for organic compounds that exhibit strong pharmacological effects on humans and animals in relatively small amounts. .
  • alkaloids Most of the plants containing a large amount of alkaloids are known as medicinal herbs, and there are mainly tropical or subtropical plants. These alkaloids also have pharmacological and toxic effects. Caution is required when consuming.
  • ⁇ -Tocopherol is a representative natural antioxidant, widely distributed in seed oil, grains, and vegetables with green leaves.
  • vitamin E As vitamin E, it is a major fat-soluble antioxidant present in cell membranes and prevents oxidation of fat. .
  • Vitamin E can react directly with various oxygen radicals including peroxy radicals (ROO ⁇ ), CCl 3 , HO ⁇ as well as superoxide radicals (O 2 ⁇ ).
  • the antioxidant activity is high in the order of ⁇ > ⁇ > ⁇ > ⁇ .
  • ROO ⁇ peroxy radicals
  • CCl 3 CCl 3
  • HO ⁇ superoxide radicals
  • the antioxidant activity is high in the order of ⁇ > ⁇ > ⁇ > ⁇ .
  • polyunsaturated fatty acids composing cell membranes are easily oxidized by free radicals made in cells. Tocopherol stops this oxidation process and removes free radicals to protect cell membranes from oxidative damage.
  • An object of the present invention is to provide an alkaloid-containing water-soluble emulsion composition that not only can water-soluble functionally poorly soluble substances to increase the absorption rate and efficacy of the substances, but also has excellent oxidative stability in aqueous solution.
  • a water-soluble antioxidant emulsion comprising the following ingredients to satisfy 100% by weight of the total:
  • alkaloid-containing water-soluble emulsion composition containing a water-soluble antioxidant emulsion comprising a.
  • the water-soluble emulsion composition containing an alkaloid according to an embodiment of the present invention can increase the absorption rate and efficacy of the material by making the functional material for poor water solubility in water, so that the functionality of the material can be utilized in various fields.
  • Example 2 is a photograph of the emulsified particles of the alkaloid-containing water-soluble emulsion composition of Example 1 observed under an optical microscope.
  • An alkaloid-containing water-soluble emulsion composition includes a water-soluble antioxidant emulsion and an alkaloid emulsion.
  • the water-soluble antioxidant emulsion is 1 to 40% by weight of tocopherol, 1 to 40% by weight of catechin, 1 to 30% by weight of the first surfactant of HLB 3 to HLB 7, HLB 10 to HLB 14 to satisfy 100% by weight of the total amount of the water-soluble antioxidant emulsion 10 to 80% by weight of a second surfactant, 10 to 45% by weight of a cosurfactant, and 1 to 35% by weight of an edible oil and fat.
  • the tocopherol and catechin are included in the emulsion as fat-soluble and water-soluble antioxidants, respectively, and the content may be appropriately determined within the range of 1 to 40 wt%. For example, it may be 5 to 35% by weight, 5 to 25% by weight, 5 to 10% by weight, but is not limited thereto. At this time, if the content of tocopherol and catechin is less than the above range, the antioxidant effect of the addition is insignificant. On the contrary, if it exceeds the above range, there is a problem that the emulsion stability of the emulsion is significantly reduced.
  • the HLB Hydrophilicity
  • the water-soluble antioxidant emulsion and the alkaloid emulsion include two surfactants with different HLB (Hydrophile-Lipophile Balance) in terms of securing the emulsion stability of each emulsion, and exhibiting the surfactant effect while being well soluble in the hydrophilic co-surfactant. do.
  • HLB Hydrophilic co-surfactant
  • the first surfactant uses a HLB of 3 to 7
  • the second surfactant uses a HLB of 10 to 14 to prevent aggregation between emulsified particles, and is an antioxidant in the hydrophilic co-surfactant and edible oil Tocopherol and catechin are more effective in terms of maintaining their respective antioxidant powers.
  • HLB of the first surfactant is less than 3
  • the emulsion is not well formed, and when the HLB exceeds 7, agglomeration between particles occurs and the emulsion stability is reduced.
  • the HLB of the second surfactant is less than 10, it is difficult to emulsify, and on the contrary, when the HLB exceeds 14, the emulsion stability is deteriorated.
  • the first surfactant of HLB 3 to HLB 7 may be used without limitation as long as it is known, for example, from the group consisting of glycerin fatty acid ester, polyglycerol fatty acid ester, sorbitan fatty ester, lecithin, propylene glycol fatty acid ester, and mixtures thereof. Only 1 selected type is possible.
  • the content of the first surfactant is 1 to 30% by weight based on the total weight of the water-soluble antioxidant emulsion. In one example, it may be selected from 5 to 20% by weight, 5 to 25% by weight, and 5 to 15% by weight. If the content of the first surfactant is less than the above range, the emulsification action on the emulsified particles of the edible oil is weakened, making it difficult to form an emulsion.
  • the second surfactant of HLB 10 to HLB 14 may be one selected from the group consisting of polyglycerin fatty acid ester, polyoxyethylene sorbitan fatty acid ester, sucrose fatty acid ester, enzymatically decomposed lecithin, and mixtures thereof, but is limited thereto not.
  • the content of the second surfactant may be appropriately determined in the range of 10 to 80% by weight based on the total weight of the water-soluble antioxidant emulsion, for example, 20 to 70% by weight, 30 to 60% by weight, 40 to 50% by weight.
  • the present invention is not limited thereto.
  • the tocopherol and catechin can be stably dispersed in the water-soluble antioxidant emulsion without impairing the antioxidant ability of tocopherol and catechin.
  • the co-surfactant serves as an auxiliary agent for emulsification and is used as a solubilizer.
  • the co-surfactant may be one selected from the group consisting of glycerin, sorbitol, polyethylene glycol, propylene glycol, triacetin, and mixtures thereof, but is not limited thereto.
  • the content of the co-surfactant is preferably 10 to 45% by weight based on the total weight of the water-soluble antioxidant emulsion. In one example, it may be selected from 10 to 40% by weight, 15 to 30% by weight, and 15 to 20% by weight. If the co-surfactant content is less than the above range, it is not easy to dissolve the catechin, and when used in excess of the above range, there is a problem in that emulsified particles are not well formed and emulsion stability is lowered.
  • the edible oil can be used without limitation as long as it is manufactured or processed using crude oil obtained from plants or animals or the raw material thereof.
  • at least one oil selected from soybean oil, corn oil, rapeseed oil, high oleic rapeseed oil, safflower oil, rice bran oil, palm oil, olive oil, sunflower oil, palm oil, wheat germ oil, and medium chain triglyceride (MCT Oil) is possible.
  • the content of such edible oils and fats may be 1 to 35% by weight based on the total weight of the composition, for example, 1 to 30% by weight, 3 to 25% by weight, 5 to 20% by weight, but is not limited thereto. If it is less than the above range, the amount of oil is too small to dissolve the tocopherol, and if it exceeds the above range, the stability over time of the emulsion is poor.
  • the alkaloid emulsion contains 1 to 30% by weight of alkaloids, 1 to 10% by weight of water-in-oil surfactants of HLB 3 to HLB 7, and 1 to 20 oil-in-water surfactants of HLB 10 to HLB 14 to satisfy 100% by weight of the total. % by weight, and 40 to 97% by weight of a cosurfactant.
  • the alkaloid may be used without limitation if it has a biological effect on a mammal when administered orally.
  • a biological effect on a mammal when administered orally.
  • piperine for example, piperine, capsaicin.
  • alkaloids are included in an amount of 1 to 30% by weight based on the total weight of the alkaloid emulsion. For example, it may be 1 to 30% by weight, 3 to 25% by weight, 5 to 20% by weight, 10 to 20% by weight, but is not limited thereto. If the content of the alkaloid is less than the above range, the effect of the addition is insignificant, and if it exceeds the above range, there is a problem in that it is difficult to form emulsified particles.
  • the alkaloid emulsion comprises a first surfactant and a second surfactant having the above-described HLB value in order to maintain the emulsion stability of the emulsion composition by exhibiting a surfactant effect while being well soluble in the hydrophilic co-surfactant.
  • the first surfactant having an HLB of 3 to 7 is included in an amount of 1 to 10% by weight based on the total weight of the alkaloid emulsion. In one example, it may be selected from 3 to 10 wt%, 5 to 10 wt%, and 8 to 10 wt%. If the content of the first surfactant is less than the above range, there is a problem in that it is difficult to form an emulsion because the emulsification action on the alkaloid emulsified particles is weakened.
  • the second surfactant having an HLB of 10 to 14 may be contained in an amount of 1 to 20% by weight based on the total weight of the alkaloid emulsion, for example, 3 to 20% by weight, 5 to 20% by weight, 10 to 20% by weight, However, the present invention is not limited thereto. At this time, if the content of the second surfactant is less than the above range, the emulsification action on the hydrophilic co-surfactant is weakened, making it difficult to emulsify, and if it exceeds the above range, there is a problem in that it is difficult to maintain emulsion stability.
  • first surfactant and the second surfactant are as described above.
  • the cosurfactant is added to disperse and dissolve the alkaloid and to play an auxiliary role in emulsification, and the content of the alkaloid emulsion is 40 to 97 wt%.
  • the content of the alkaloid emulsion is 40 to 97 wt%.
  • it may be 40 to 90% by weight, 40 to 80% by weight, 40 to 70% by weight, 50 to 60% by weight, but is not limited thereto. If it is less than the above range, it is difficult to maintain emulsion stability, and if it exceeds the above range, it is difficult to stably disperse the alkaloid.
  • the alkaloid-containing water-soluble emulsion composition comprises 0.1 to 20% by weight of the water-soluble antioxidant emulsion; and 80 to 99.9 wt% of the alkaloid emulsion.
  • the water-soluble antioxidant emulsion may be 0.1 to 15% by weight, 0.1 to 10% by weight, 1 to 15% by weight, 1 to 10% by weight, but is not limited thereto.
  • the alkaloid emulsion may be 80 to 99.9 wt%, 80 to 99.9 wt%, 90 to 99.9 wt%, 90 to 99 wt%, but is not limited thereto.
  • the water-soluble emulsion composition containing alkaloids of the present invention can increase the absorption rate and efficacy of substances by soluble in alkaloids, which are functional substances for poor water use, so that the functional properties of substances can be utilized in various fields.
  • it since it contains a water-soluble antioxidant emulsion, it has excellent oxidation stability that can prevent oxidation by oxygen in aqueous solution.
  • raw material 1 was prepared by sequentially adding catechin, soybean oil, and tocopherol.
  • raw material 2 was prepared by adding a second surfactant to glycerin.
  • the second surfactant 30 wt% and 70 wt% of the total amount of the raw material 1 and 2 were used, respectively.
  • Preparation 9 Preparation 10
  • Preparation 11 Preparation 12
  • Preparation 13 Preparation 14 piperine 20.0 20.0 20.0 20.0 20.0 20.0 20.0 20.0 first surfactant glycerin fatty acid esters (HLB:4) 10.0 - 10.0 - - 30.0 sucrose fatty acid esters (HLB: 2) - 10.0 - - - - Polyglyceryl-6 diisostearate (HLB: 8) - 10.0 - second surfactant polyglycerin fatty acid esters (HLB: 12) 20.0 20.0 - - 30.0 - Polyglyceryl-6 diisostearate (HLB: 8) - - 20.0 - - - PEG-18 Stearate (HLB: 18) - - - - 20.0 - - glycerin 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0
  • Preparation 15 Ingredients/mixture ratio (wt%) Preparation 15
  • Preparation 16 Preparation 17
  • Preparation 18 Preparation 19
  • Preparation 20 capsaicin 20.0 20.0 20.0 20.0 20.0 20.0 20.0 20.0 first surfactant glycerin fatty acid esters (HLB:4) 10.0 - 10.0 - - 30.0 sucrose fatty acid esters (HLB: 2) - 10.0 - - - - - Polyglyceryl-6 diisostearate (HLB: 8) - 10.0 - second surfactant polyglycerin fatty acid esters (HLB: 12) 20.0 20.0 - - 30.0 - Polyglyceryl-6 diisostearate (HLB: 8) - - 20.0 - - - PEG-18 Stearate (HLB: 18) - - - - 20.0 - - glycerin 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0 50.0
  • the mixture was stirred at 500 rpm or less while maintaining the temperature at 50° C. or higher.
  • the homomixer was stirred and the rpm was gradually increased while emulsifying and dispersing at 5,000 rpm or higher.
  • glycerin was added and stirred at 500 rpm or less to prepare an alkaloid emulsion.
  • the antioxidant effect of the alkaloid-containing water-soluble emulsion composition including the water-soluble antioxidant emulsion was measured using the DPPH measurement method.
  • Measurement of DPPH radical scavenging activity is the most commonly used method to measure antioxidant activity, and it is a method to evaluate antioxidant activity by color change. Since many changes do not occur, the absorbance is measured with a spectrophotometer (517 nm) to compare the antioxidant activity, and the higher the value, the higher the antioxidant effect is evaluated.
  • Experimental conditions severe condition test: oxidation induced by leaving at 40°C for 1 week) are as follows.
  • the aqueous solubility of the prepared alkaloid-containing water-soluble emulsion composition was confirmed as follows. 50 ml of distilled water was added to the emulsion composition of Examples and Comparative Examples while maintaining a water temperature of 38° C. in a constant temperature water bath and maintaining a speed of 100 rpm. After 1 hour, centrifugation was followed by filtration, and the water content was measured by Karl Fisher method to quantify the organic matter content.
  • the emulsified particle size of the alkaloid-containing water-soluble emulsion composition prepared according to Tables 8 and 11 was confirmed as follows. 50 ml of distilled water was added to the emulsion composition of Examples and Comparative Examples while maintaining a water temperature of 38° C. in a constant temperature water bath and maintaining a speed of 100 rpm. After 1 hour, the emulsified particles were observed under an optical microscope, and the results are shown in FIGS. 1 and 2 .
  • the size of the emulsified particles in the distilled water was measured using a Zetasizer Nano ZS (Malvern Instrument, U.K.). At this time, the sample was repeatedly measured three times, and the average value is shown in Table 15 below.
  • the alkaloid-containing water-soluble emulsion composition according to an embodiment of the present invention forms emulsified particles of 1.0 to 5.0 ⁇ m, while the alkaloid-containing water-soluble emulsion composition of Comparative Examples 33 to 52 The composition did not form emulsified particles, so the size of the emulsified particles could not be measured. From this, it can be expected that the alkaloid-containing water-soluble emulsion composition according to the present invention can be absorbed in the body and exhibit high bioavailability.

Abstract

La présente invention concerne une composition émulsifiée soluble dans l'eau contenant un alcaloïde comprenant une émulsion antioxydante soluble dans l'eau. Une composition émulsifiée soluble dans l'eau contenant un alcaloïde selon un mode de réalisation de la présente invention peut solubiliser un matériau fonctionnel non soluble dans l'eau pour augmenter le taux d'absorption et l'efficacité du matériau, ce qui permet d'utiliser la fonctionnalité du matériau dans divers domaines. De plus, contenant une émulsion antioxydante soluble dans l'eau, la composition est parfaite en termes de stabilité à l'oxydation, ce qui permet d'empêcher l'oxydation induite par l'oxygène dans une solution aqueuse.
PCT/KR2021/018432 2020-12-15 2021-12-07 Composition émulsifiée soluble dans l'eau contenant un alcaloïde WO2022131656A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
KR10-2020-0174987 2020-12-15
KR1020200174987A KR102524312B1 (ko) 2020-12-15 2020-12-15 엑디스테로이드 함유 수용성 유화 조성물
KR10-2021-0026166 2021-02-26
KR1020210026166A KR20220122840A (ko) 2021-02-26 2021-02-26 알칼로이드 함유 수용성 유화 조성물

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WO2022131656A1 true WO2022131656A1 (fr) 2022-06-23

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07227227A (ja) * 1993-12-20 1995-08-29 Sanei Gen F F I Inc 安定な乳化組成物及びそれを含有する食品
KR100359044B1 (ko) * 1993-07-08 2003-02-05 노파르티스 아게 난용성활성물질용제약조성물
US20070087104A1 (en) * 2005-10-14 2007-04-19 Wild Flavors, Inc. Microemulsions for use in food and beverage products
JP2011252015A (ja) * 2003-05-22 2011-12-15 Lipocine Inc 疎水性薬物投与のための医薬組成物及び剤形
JP2013159730A (ja) * 2012-02-07 2013-08-19 Ogawa & Co Ltd 油溶性酸化防止剤及びその製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR100359044B1 (ko) * 1993-07-08 2003-02-05 노파르티스 아게 난용성활성물질용제약조성물
JPH07227227A (ja) * 1993-12-20 1995-08-29 Sanei Gen F F I Inc 安定な乳化組成物及びそれを含有する食品
JP2011252015A (ja) * 2003-05-22 2011-12-15 Lipocine Inc 疎水性薬物投与のための医薬組成物及び剤形
US20070087104A1 (en) * 2005-10-14 2007-04-19 Wild Flavors, Inc. Microemulsions for use in food and beverage products
JP2013159730A (ja) * 2012-02-07 2013-08-19 Ogawa & Co Ltd 油溶性酸化防止剤及びその製造方法

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