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WO2016129611A1 - Composition d'antioxydant et huile dans laquelle celle-ci a été ajoutée - Google Patents

Composition d'antioxydant et huile dans laquelle celle-ci a été ajoutée Download PDF

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Publication number
WO2016129611A1
WO2016129611A1 PCT/JP2016/053876 JP2016053876W WO2016129611A1 WO 2016129611 A1 WO2016129611 A1 WO 2016129611A1 JP 2016053876 W JP2016053876 W JP 2016053876W WO 2016129611 A1 WO2016129611 A1 WO 2016129611A1
Authority
WO
WIPO (PCT)
Prior art keywords
antioxidant composition
weight
oil
oils
fats
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2016/053876
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English (en)
Japanese (ja)
Inventor
基 名坂
孝史 岩田
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
FOODTECH TRADING Co Ltd
Original Assignee
FOODTECH TRADING Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by FOODTECH TRADING Co Ltd filed Critical FOODTECH TRADING Co Ltd
Publication of WO2016129611A1 publication Critical patent/WO2016129611A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/04—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds
    • C09K15/06—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen
    • C09K15/08—Anti-oxidant compositions; Compositions inhibiting chemical change containing organic compounds containing oxygen containing a phenol or quinone moiety
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K15/00—Anti-oxidant compositions; Compositions inhibiting chemical change
    • C09K15/34—Anti-oxidant compositions; Compositions inhibiting chemical change containing plant or animal materials of unknown composition
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom

Definitions

  • the present invention relates to an antioxidant composition and fats and oils to which it is added.
  • Oxidation of fats and oils is not only a cause of off-flavor and discoloration, but lipid peroxides produced by oxidation are known to be harmful to the human body. Accordingly, there has always been a demand for an excellent antioxidant to prevent such harmful effects.
  • Synthetic antioxidants such as BHA (Butylated hydroxyanisol) and BHT (Butylated hydroxytoluene) are highly effective antioxidants, but are refrained from use because consumers tend to prefer natural products due to safety issues. Tend.
  • tocopherol and rosemary extract are used as natural antioxidants.
  • the effect is insufficient as compared with synthetic antioxidants, and the price is high.
  • catechins of tea polyphenols are known to have extremely excellent antioxidant properties (see Patent Documents 1 and 2).
  • tea catechins of tea polyphenols are water-soluble, and as such, cannot be uniformly dissolved in fats and oils and cannot exhibit a sufficient antioxidant effect. Therefore, a technique for dissolving catechins in fats and oils using an emulsifier or the like has been proposed in order to exhibit the antioxidant properties of catechins in fats and oils.
  • the object of the present invention is to overcome the above-mentioned problems, does not contain water or unnecessary alcohol that is originally removed during cooking using fats and oils, is easy to adjust the antioxidant composition, and further in fats and oils. It is to provide an antioxidant composition having excellent solubility in water.
  • the inventors of the present invention have the idea that catechins can be dissolved if there is a hydrophilic group and a lipophilic group in the molecular structure of catechins, and the substance has a similar balance of hydrophilic group and lipophilic group. As a result of intensive studies, the present invention has been completed.
  • the present invention [1] 0.1-30 parts by weight of catechins are dissolved in 70-99.9 parts by weight of diglycerin fatty acid ester, the diglycerin fatty acid ester is diglycerin oleate, and the diglycerin oleate is mono An antioxidant composition having an ester content of 50% or more. [2] An oil or fat containing the antioxidant composition according to claim 1.
  • the antioxidant composition of the present invention can be produced by a very simple method in which catechins are heated and dissolved in diglycerin fatty acid ester. Furthermore, there is an advantage that it is not necessary to add water and alcohols that are excluded during cooking using fats and oils, regardless of the antioxidant. In this way, high-speed agitation and pressure emulsification, which have been conventionally performed, are not performed, and the content of components that are not originally related to anti-oxidation is small, and it can be manufactured in a short process, so it is possible to supply an inexpensive antioxidant composition To.
  • the antioxidant preparation in the present invention is characterized by dissolving catechins in diglycerin fatty acid ester.
  • the fat and oil containing the antioxidant composition is characterized by dissolving the antioxidant preparation of the present invention in the fat and oil.
  • catechins include epicatechin, epigallocatechin, epicatechin gallate, epigallocatechin gallate and the like, and both natural extracts and synthetic products can be used. These can be used alone or in combination.
  • Natural extracts are obtained from Japanese tea, oolong tea, black tea, etc. by extraction with organic solvents such as ethanol, ethyl acetate, chloroform, hexane, water, supercritical carbon dioxide and the like. Natural extracts contain impurities such as saccharides in addition to catechins, but these impurities can be used without separation. Moreover, what removed the impurities using the concentration by solvent distillation etc. as needed, HPLC method, a solvent fractionation method, column purification method, etc. can also be used.
  • the catechins used in the present invention can be exemplified by commercial tea extracts such as “Polyphenone” manufactured by Mitsui Norin Co., Ltd., “Sunphenon” manufactured by Taiyo Kagaku Co., Ltd., and these as raw materials.
  • “Polyphenon 70S” manufactured by Mitsui Norin Co., Ltd. and “Sunphenon 100S” manufactured by Taiyo Kagaku Co., Ltd. are preferably used as commercially available products that have already been subjected to purification treatment. it can.
  • Catechins of the present invention can be obtained from the Japan Food Analysis Center, “Fiveth Explanation of Japanese Food Ingredient Analysis Manual”, Central Law, July 2001, p. 252 can be measured by colorimetric determination using iron tartrate (iron tartrate reagent method), but in order to measure the composition of catechins in detail, it can be measured by reversed-phase high-performance liquid chromatography. it can.
  • the antioxidant composition of the present invention contains catechins in an amount of 0.1 to 30 parts by weight, preferably 1 to 20 parts by weight, more preferably 1 to 5 parts by weight, based on the diglycerin fatty acid ester.
  • catechins in an amount of 0.1 to 30 parts by weight, preferably 1 to 20 parts by weight, more preferably 1 to 5 parts by weight, based on the diglycerin fatty acid ester.
  • the content of catechins is 30 parts by weight or more, the viscosity of the antioxidant composition is increased, and further, the catechins cannot be completely dissolved, which is not preferable.
  • the content of catechins is 0.1 parts by weight or less, the effect as an antioxidant cannot be sufficiently exhibited.
  • the diglycerin fatty acid ester used in the present invention is obtained by esterifying diglycerin and a fatty acid at 230 to 250 ° C. in a nitrogen atmosphere using a catalyst such as caustic soda as required.
  • Examples of the diglycerin used for the production of the diglycerin fatty acid ester include commercially available products such as those manufactured by Sakamoto Yakuhin Co., Ltd. and Solvay.
  • the type of fatty acid is not particularly limited, and oleic acid, stearic acid, palmitic acid, myristic acid, lauric acid, capric acid, caprylic acid and the like can be used. Of these, diglycerin oleate is preferred because it is liquid at room temperature and is easy to use.
  • the diglycerin fatty acid ester used in the present invention can be obtained by reacting and having a monoester content of 30 to 40%. Preferably, the monoester content is set to 50% or more using molecular distillation. Those are preferred.
  • Examples of the diglycerin fatty acid ester used in the present invention include commercially available product groups such as “Poem” manufactured by Riken Vitamin Co., Ltd. and “Sunsoft” manufactured by Taiyo Kagaku Co., Ltd. It is possible to preferably use “Poem DO-100V” manufactured by Riken Vitamin and “Sunsoft Q-17D” manufactured by Taiyo Kagaku, which are diglycerin oleate of at least%.
  • a synergist that increases the antioxidant effect of catechins can be used.
  • examples of the synergist include, but are not limited to, ascorbic acid fatty acid ester and tocopherol.
  • the antioxidant preparation of the present invention can be used in combination with an emulsifier other than diglycerin fatty acid ester for the purpose of adjusting the dispersibility when added to fats and oils or the emulsified properties of the added fats and oils.
  • an emulsifier other than diglycerin fatty acid ester for the purpose of adjusting the dispersibility when added to fats and oils or the emulsified properties of the added fats and oils.
  • the emulsifier used in combination include glycerin fatty acid ester, polyglycerin fatty acid ester, organic acid monoglyceride, propylene glycol fatty acid ester, sorbitan fatty acid ester, sucrose fatty acid ester, lecithin, and enzymatically decomposed lecithin, but are not particularly limited. .
  • the manufacturing method of the antioxidant composition of the present invention will be described.
  • the diglycerin fatty acid ester is dissolved in a tank at 60 to 80 ° C., and catechins are added while agitating with a propeller while agitating with nitrogen gas as necessary, and further stirred for 5 to 10 minutes.
  • the manufacturing method of the fats and oils containing the antioxidant composition of this invention can be easily obtained by mix
  • the amount of the antioxidant composition of the present invention added to the fats and oils may be appropriately set depending on the type of fats and oils to be added or the method of use.
  • the amount added to the fats and oils is preferably 0.001 to 10% by weight.
  • 0.01 to 1% by weight can be added.
  • edible fats and oils are preferable, for example, palm oil, palm kernel oil, coconut oil, corn oil, cottonseed oil, soybean oil, rapeseed oil, rice oil, sunflower oil, safflower oil, olive oil, fallen green Oil, sesame oil, evening primrose oil, cacao butter, beef tallow, lard, fish oil, whale oil, etc. are raised. Further, it is also possible to apply medium chain fatty acid triglyceride obtained by esterifying caprylic acid or capric acid with glycerin. In particular, when added to deep-fried oil used for fried foods such as tempura, fried food, confectionery, ramen, etc., it exhibits the effect of preventing the generation of strange odors and discoloration of fats and oils during cooking.
  • Processed foods to which the present invention can be applied are foods containing the above fats and oils, for example, fish paste products such as chikuwa, kamaboko, fish sausage and ham, and delicacies such as dried fish, snacks, potato chips, chocolate, etc.
  • Foods, beverages, energy drinks, health foods, therapeutic foods, and the like that contain a large amount of fats and oils such as confectionery, instant noodles, edible oil, margarine, dressing, butter and the like are fried.
  • the antioxidant preparation obtained by the present invention can be used as an antioxidant for products using oils and fats such as cosmetics, quasi-drugs, feeds, industrial products and the like in addition to foods.
  • the antioxidant composition of the present invention has catechins dissolved uniformly, and as a result, even when added to fats and oils, it dissolves transparently without becoming cloudy. Furthermore, it turns out that the antioxidant effect at the time of adding to fats and oils is also excellent.
  • Example 9 1 kg (0.1% by weight) of the antioxidant composition prepared in Example 1 was added to and mixed with 999 kg (99.9% by weight) of corn oil and filled into a 5 gallon can with 16.5 kg. A liquid oil without turbidity could be obtained. The smell and color were good. The peroxide value at the time of adjustment was 0.2. When this corn oil was stored in a thermostatic chamber at 37 ° C. for 6 months and then inspected, the odor and color did not change, and the measurement result of the peroxide value was 0.5. It turns out that the fats and oils containing the antioxidant composition of this invention are the outstanding quality.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Botany (AREA)
  • General Chemical & Material Sciences (AREA)
  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Fats And Perfumes (AREA)
  • Edible Oils And Fats (AREA)

Abstract

L'objectif de la présente invention est d'obtenir une composition d'antioxydant qui peut être facilement dissoute dans des graisses et des huiles sans précipiter ni mettre en suspension des catéchines qui sont insolubles dans les graisses et les huiles, et qui présente un excellent effet antioxydant. Cet objectif est atteint en ce que 0,1 à 30 parties en poids de catéchines sont dissoutes dans 70 à 99,9 parties en poids d'un monoester d'oléate de diglycérine afin d'obtenir ladite composition d'antioxydant.
PCT/JP2016/053876 2015-02-09 2016-02-01 Composition d'antioxydant et huile dans laquelle celle-ci a été ajoutée Ceased WO2016129611A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2015037381A JP5786215B1 (ja) 2015-02-09 2015-02-09 抗酸化剤組成物およびそれを添加した油脂
JP2015-037381 2015-02-09

Publications (1)

Publication Number Publication Date
WO2016129611A1 true WO2016129611A1 (fr) 2016-08-18

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PCT/JP2016/053876 Ceased WO2016129611A1 (fr) 2015-02-09 2016-02-01 Composition d'antioxydant et huile dans laquelle celle-ci a été ajoutée

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JP (1) JP5786215B1 (fr)
WO (1) WO2016129611A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023210454A1 (fr) * 2022-04-27 2023-11-02 株式会社Ftt Composition antioxydante, et huile et matière grasse comestibles

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6785083B2 (ja) * 2016-07-29 2020-11-18 ミヨシ油脂株式会社 抗酸化剤、抗酸化剤を含有する油脂組成物およびこれを含有する油性食品
JP7753138B2 (ja) * 2022-03-18 2025-10-14 理研ビタミン株式会社 油脂及び油溶性機能性成分用酸化防止剤の製造方法

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06254378A (ja) * 1993-03-02 1994-09-13 Nippon Oil & Fats Co Ltd 水溶性化合物油溶化製剤およびその製造方法
JP2001131572A (ja) * 1999-10-29 2001-05-15 Riken Vitamin Co Ltd 酸化防止剤組成物及び油脂組成物
JP2008163202A (ja) * 2006-12-28 2008-07-17 Mitsui Norin Co Ltd カテキン類が添加された油脂の着色抑制方法
WO2008143182A1 (fr) * 2007-05-17 2008-11-27 Kaneka Corporation Composition contenant un polyphénol dérivé de la réglisse
JP2010261075A (ja) * 2009-05-08 2010-11-18 Taiyo Kagaku Co Ltd 防錆剤、防錆処理方法、及びその除去方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06254378A (ja) * 1993-03-02 1994-09-13 Nippon Oil & Fats Co Ltd 水溶性化合物油溶化製剤およびその製造方法
JP2001131572A (ja) * 1999-10-29 2001-05-15 Riken Vitamin Co Ltd 酸化防止剤組成物及び油脂組成物
JP2008163202A (ja) * 2006-12-28 2008-07-17 Mitsui Norin Co Ltd カテキン類が添加された油脂の着色抑制方法
WO2008143182A1 (fr) * 2007-05-17 2008-11-27 Kaneka Corporation Composition contenant un polyphénol dérivé de la réglisse
JP2010261075A (ja) * 2009-05-08 2010-11-18 Taiyo Kagaku Co Ltd 防錆剤、防錆処理方法、及びその除去方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023210454A1 (fr) * 2022-04-27 2023-11-02 株式会社Ftt Composition antioxydante, et huile et matière grasse comestibles

Also Published As

Publication number Publication date
JP2016145309A (ja) 2016-08-12
JP5786215B1 (ja) 2015-09-30

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