JP5786215B1 - Antioxidant composition and fats and oils to which it is added - Google Patents
Antioxidant composition and fats and oils to which it is added Download PDFInfo
- Publication number
- JP5786215B1 JP5786215B1 JP2015037381A JP2015037381A JP5786215B1 JP 5786215 B1 JP5786215 B1 JP 5786215B1 JP 2015037381 A JP2015037381 A JP 2015037381A JP 2015037381 A JP2015037381 A JP 2015037381A JP 5786215 B1 JP5786215 B1 JP 5786215B1
- Authority
- JP
- Japan
- Prior art keywords
- oils
- fats
- antioxidant composition
- weight
- antioxidant
- 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.)
- Active
Links
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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Botany (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Edible Oils And Fats (AREA)
Abstract
【課題】油脂に不溶のカテキン類を白濁や沈殿することなく油脂に溶解でき、さらに抗酸化効果に優れた抗酸化剤組成物を得る。【解決手段】カテキン類0.1〜30重量部をジグリセリン脂肪酸エステル70〜99.9重量部に溶解して抗酸化剤組成物を得る。【選択図】なしAn antioxidant composition that can dissolve catechins that are insoluble in fats and oils without being clouded or precipitated, and that has an excellent antioxidant effect. An antioxidant composition is obtained by dissolving 0.1 to 30 parts by weight of catechins in 70 to 99.9 parts by weight of diglycerin fatty acid ester. [Selection figure] None
Description
本発明は、抗酸化剤組成物及びそれを添加した油脂に関する。 The present invention relates to an antioxidant composition and fats and oils to which the composition is added.
油脂の酸化は異臭の発生や変色の原因となるだけでなく、酸化により生成する過酸化脂質は人体に有害であることが知られている。したがって、このような弊害を防止するために優れた抗酸化剤が常に求められていた。BHA(Butylated hydroxyanisol)、BHT(Butylated hydroxytoluene)などの合成抗酸化剤は効果の高い抗酸化剤ではあるが、安全性の問題から消費者が天然物を好む傾向があるため使用が控えられている傾向がある。 It is known that the oxidation of fats and oils not only causes the generation of a strange odor and causes discoloration, but also the lipid peroxide produced by oxidation is 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 hydrogenisol) and BHT (Butylated hydrogentoluene) are effective antioxidants, but they are refrained from use because consumers tend to prefer natural products due to safety issues. Tend.
こうした背景から、天然の抗酸化剤としてトコフェロールやローズマリー抽出物が利用されている。しかしながら、その効果は合成抗酸化剤に比べて不十分である上、価格も高いといった問題がある。
一方、茶ポリフェノールのカテキン類にはきわめて優れた抗酸化性が知られている(特許文献1及び2参照)。Against this background, tocopherol and rosemary extract are used as natural antioxidants. However, the effect is insufficient as compared with synthetic antioxidants, and the price is high.
On the other hand, catechins of tea polyphenols are known to have extremely excellent antioxidant properties (see Patent Documents 1 and 2).
しかしながら、茶ポリフェノールのカテキン類は水溶性であるため、そのままでは油脂に対して均一に溶解することができず、十分な酸化防止効果を発揮することができない。そこで、カテキン類の抗酸化性を油脂中で発揮させるため、乳化剤等を用いてカテキン類を油脂に溶解する技術が提案されている。 However, since tea polyphenol catechins are water-soluble, they cannot be dissolved uniformly in fats and oils as they are, 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.
例えば、カテキン類を油脂に分散させる方法として、親油性乳化剤を用いてカテキン類を乳化した油中水型乳化物の親油性抗酸化剤(特許文献3参照)、あるいはカテキン類を水及びまたはアルコール類に溶解して更に複数の乳化剤を用いて油脂中に溶解する方法が提案されている(特許文献4及び5参照)。
油脂中にカテキン類を均一に溶解させる方法としては、上記のようにいくつかの手段が開示されている。しかしながら、これらの手段は油脂中にカテキン類を溶解するという目的についてはある程度達成されるものの、油脂を用いて調理することにより除去される水を添加したり、本来必要のないアルコールを添加するなど実用的でない。さらには、複数の乳化剤を用いて、何段階かの長い製造工程も必要となる。 Several methods have been disclosed as methods for uniformly dissolving catechins in fats and oils as described above. However, although these means are achieved to some extent for the purpose of dissolving catechins in fats and oils, water that is removed by cooking with fats and oils, alcohol that is not necessary in nature, etc. are added. Not practical. Furthermore, several long production processes are required using a plurality of emulsifiers.
したがって、本発明の目的は、上記問題点を克服した、本来油脂を使用した調理中に除かれる水や不必要なアルコールを含まず、抗酸化剤組成物の調整が簡便で、更には油脂中への溶解性に優れる抗酸化剤組成物を提供することである。 Accordingly, 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.
本発明者らは、カテキン類の分子構造中に親水基と親油基があり、同様な親水基と親油基のバランスの物質であれば、カテキン類を溶解可能であるとの着想の下、鋭意研究の結果本発明を完成するに至った。 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.
すなわち、本発明は、
〔1〕カテキン類0.1〜30重量部をジグリセリン脂肪酸エステル70〜99.9重量部に溶解し、前記ジグリセリン脂肪酸エステルがジグリセリンオレイン酸エステルであり、このジグリセリンオレイン酸エステルがモノエステル含量70%以上である抗酸化剤組成物。
〔2〕〔1〕記載の抗酸化剤組成物を含有する油脂。That is, 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 70% or more .
[2] [1] Symbol mounting of fats and oils comprising the antioxidant composition.
本発明の抗酸化剤組成物は、カテキン類をジグリセリン脂肪酸エステルに加熱溶解するという非常に簡便な方法で製造することができる。更には本来抗酸化と関係なく、油脂を利用した調理中の除かれる水やアルコール類を添加する必要もないという利点もある。
このように、従来行われていた高速撹拌や加圧乳化を行わず、本来抗酸化とは関係ない成分の含有も少なく、短い工程で製造できるので、安価な抗酸化剤組成物の供給を可能にする。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.
本発明における抗酸化剤製剤とは、カテキン類をジグリセリン脂肪酸エステルに溶解することを特徴とする。また、抗酸化剤組成物を含有する油脂とは、本発明の抗酸化剤製剤を油脂に溶解することを特徴とする、 The antioxidant preparation in the present invention is characterized by dissolving catechins in diglycerin fatty acid ester. Moreover, the fat and oil containing the antioxidant composition is characterized by dissolving the antioxidant preparation of the present invention in the fat and oil.
本発明においてカテキン類とは、エピカテキン、エピガロカテキン、エピカテキンガレート、エピガロカテキンガレート等があげられ、天然抽出品、合成品いずれも用いることができる。これらは単品もしくは組み合わせで用いることができる。 In the present invention, 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.
天然抽出品は日本茶、ウーロン茶、紅茶等から、エタノール、酢酸エチル、クロロホルム、ヘキサン等の有機溶剤や、水、超臨界二酸化炭素などで抽出することにより得られる。天然抽出品中にはカテキン類のほかに糖質などの不純物が含まれているが、これらの不純物を分離することなく用いることができる。また、必要に応じて溶媒留去などによる濃縮や、HPLC法、溶媒分画法、カラム精製法などを用いて不純物を除去したものも用いることができる。 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.
また、本発明に用いるカテキン類は市販の茶抽出物、例えば三井農林(株)製「ポリフェノン」、太陽化学(株)製「サンフェノン」などの商品群を例示することができ、これらを原料として精製処理しても良いが、その中でもすでに精製処理が施されている市販品として、三井農林(株)製「ポリフェノン70S」、太陽化学(株)製「サンフェノン100S」を好適に使用することができる。 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. Of these, “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.
本発明のカテキン類は、日本食品分析センター編、「五訂 日本食品成分分析マニュアルの解説」、中央法規、2001年7月、P.252に記載の酒石酸鉄を用いた比色定量法(酒石酸鉄試薬法)により測定可能であるが、カテキン類の組成を詳細に測定するためには、逆相高速液体クロマトグラフィーで測定することができる。 The catechins of the present invention can be obtained from the Japan Food Analysis Center, “Explanation of Manual for Fifth Japanese Food Ingredient Analysis”, 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.
本発明の抗酸化剤組成物はカテキン類をジグリセリン脂肪酸エステルに対して0.1〜30重量部、好ましくは1〜20重量部、更に好ましくは1〜5重量部含有する。カテキン類の含有量が30重量部以上の場合抗酸化剤組成物の粘度が上がり、更には完全に溶解できなくなり、好ましくない。カテキン類の含量が0.1重量部以下の場合は抗酸化剤としての効果を十分発揮することができない。 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. When 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. When the content of catechins is 0.1 parts by weight or less, the effect as an antioxidant cannot be sufficiently exhibited.
本発明に用いるジグリセリン脂肪酸エステルは、ジグリセリンと脂肪酸を必要に応じて触媒例えば苛性ソーダなどを使用して、窒素雰囲気下、230〜250℃にてエステル化することにより得られる。
ジグリセリン脂肪酸エステルの製造に用いるジグリセリンは、例えば阪本薬品(株)製、ソルベー社製等の市販品がある。また、脂肪酸はその種類としては、特に限定するものではないが、オレイン酸、ステアリン酸、パルミチン酸、ミリスチン酸、ラウリン酸、カプリン酸、カプリル酸等を使用することができる。この中ではジグリセリンオレイン酸エステルが、常温で液状であるため使用しやすく、好ましい。
本発明に用いるジグリセリン脂肪酸エステルは、反応することにより得られる、モノエステル含量30〜40%のものを使用することができるが、好ましくは、分子蒸留を用いてモノエステル含量70%以上としたものが好適である。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. Further, 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.
As the diglycerin fatty acid ester used in the present invention, a monoester content of 30 to 40% obtained by reacting can be used. Preferably, the monoester content is set to 70% or more using molecular distillation. Those are preferred.
本発明に用いるジグリセリン脂肪酸エステルは市販の、理研ビタミン(株)製「ポエム」、太陽化学(株)製「サンソフト」などの商品群を例示することができ、その中でもモノエステル含量が70%以上のジグリセリンオレイン酸エステルである、理研ビタミン製「ポエム DO−100V」、太陽化学製「サンソフト Q−17D」を好適に使用することができる。 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 suitably use “Poem DO-100V” manufactured by Riken Vitamin and “Sunsoft Q-17D” manufactured by Taiyo Kagaku, which are diglycerin oleate of at least%.
本発明の抗酸化剤製剤は、カテキン類の酸化防止効果を増加させる相乗剤を使用することができる。相乗剤としては、アスコルビン酸脂肪酸エステル、トコフェロール等を挙げることができるが特に限定するものではない。 The antioxidant preparation of the present invention can use a synergist that increases the antioxidant effect of catechins. Examples of the synergist include, but are not limited to, ascorbic acid fatty acid ester and tocopherol.
本発明の抗酸化剤製剤は、油脂に添加したときの分散性、あるいは添加した油脂の被乳化特性を調整することを目的としてジグリセリン脂肪酸エステル以外の乳化剤を併用することができる。
併用する乳化剤としては、グリセリン脂肪酸エステル、ポリグリセリン脂肪酸エステル、有機酸モノグリセリド、プロピレングリコール脂肪酸エステル、ソルビタン脂肪酸エステル、ショ糖脂肪酸エステル、レシチン、酵素分解レシチンなどが挙げられるが、特に限定するものではない。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.
Examples of 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. .
本発明の抗酸化剤組成物の製造方法について説明する。タンク中にジグリセリン脂肪酸エステルを60〜80℃に溶解し、必要に応じて窒素ガスを通気しながら、プロペラ撹拌をしながらカテキン類を投入し、5〜10分更に撹拌することにより完成する。また、粘度を低下させるなどの目的で、油脂等で希釈しても良い。
本発明の抗酸化剤組成物を含む油脂の製造方法は、油脂類に上記方法で得られた抗酸化剤製剤を配合、混合することにより容易に得ることができる。
本発明の抗酸化剤組成物の油脂に対する添加量は、添加対象となる油脂の種類または使用方法により適宜設定すればよく、例えば油脂に対する添加量を、好ましくは0.001〜10重量%、より好ましくは0.01〜1重量%添加することができる。The manufacturing method of the antioxidant composition of the present invention will be described. The diglycerin fatty acid ester is dissolved in the tank at 60 to 80 ° C., and catechins are added while stirring the propeller while agitating with nitrogen gas as necessary, and the mixture is further stirred for 5 to 10 minutes. Moreover, you may dilute with fats and oils for the purpose of decreasing a viscosity.
The manufacturing method of the fats and oils containing the antioxidant composition of this invention can be easily obtained by mix | blending and mixing the antioxidant preparation obtained by the said method with fats and oils.
What is necessary is just to set suitably the addition amount with respect to the fats and oils of the antioxidant composition of this invention by the kind or usage method of the fats and oils used for addition, for example, the addition amount with respect to fats and oils, Preferably it is 0.001 to 10 weight%. Preferably 0.01 to 1 weight% can be added.
本発明を適用しうる油脂としては、食用油脂が好ましく例えば、パーム油、パーム核油、ヤシ油、コーン油、綿実油、大豆油、菜種油、米油、ひまわり油、サフラワー油、オリーブ油、落下生油、ごま油、月見草油、カカオ脂、牛脂、豚脂、魚油、鯨油などが上げられる。また、カプリル酸やカプリン酸をグリセリンとエステル化反応して得られる中鎖脂肪酸トリグリセライドの適用も可能である。
特に、てんぷらやフライ、菓子やラーメンなどの揚げ物等に用いる揚げ油に添加すると、調理時の油脂類の異臭の発生や変色の防止効果を発揮する。As the fats and oils to which the present invention can be applied, 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.
本発明を適用しうる加工食品とは、上記油脂を含む食品であり、例えば、ちくわ、かまぼこ、魚肉ソーセージ・ハム等の水産練り製品や干物等の珍味類、また、スナック、ポテトチップス、チョコレートなどの菓子類やインスタントラーメン、さらには食用油、マーガリン、ドレッシング、バター等の油脂を多く含有する食品、飲料、栄養ドリンク、健康食品、治療食などが揚げられる。 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.
本発明によって得られた、抗酸化剤製剤は、食品以外に、例えば、化粧品、医薬部外品、飼料、工業製品などの油脂を使用する製品の抗酸化剤としても使用することができる。 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, etc., in addition to foods.
以下に実勢例を挙げ、本発明を更に詳しく説明する。ただし、本発明はこれに限定されるものではない。 Hereinafter, the present invention will be described in more detail with examples. However, the present invention is not limited to this.
〔サンプルの作成〕 [Create sample]
実施例1
カテキン(ポリフェノン60A=カテキン含量60重量%:三井農林(株)製)0.5Kg(5重量%)を60℃に溶解したジグリセリンオレイン酸エステル(ポエム DO−100V=モノエステル含量80%:理研ビタミン(株)製)9.5Kg(95重量%)に添加して、プロペラ撹拌にて10分間混合した。透明な液状の抗酸化剤組成物を得ることができた。抗酸化剤組成物として良好な状態である。Example 1
Catechin (polyphenone 60A = catechin content 60% by weight: manufactured by Mitsui Norin Co., Ltd.) 0.5 kg (5% by weight) dissolved in diglycerin oleate (Poem DO-100V = monoester content 80%: RIKEN) Vitamin Co., Ltd.) was added to 9.5 kg (95% by weight) and mixed for 10 minutes with propeller stirring. A transparent liquid antioxidant composition could be obtained. It is in a good state as an antioxidant composition.
実施例2
カテキン(ポリフェノン60A=カテキン含量60重量%:三井農林(株)製)5g(5重量%)を80℃に溶解したジグリセリンステアリン酸エステル(サンソフト Q−18B=モノエステル含量35%:太陽化学(株)製)95g(95重量%)に添加して、プロペラ撹拌にて5分間混合した。透明な液状の抗酸化剤組成物を得ることができた。抗酸化剤組成物として良好な状態である。Example 2
Catechin (polyphenone 60A = catechin content 60% by weight: manufactured by Mitsui Norin Co., Ltd.) 5 g (5% by weight) dissolved in diglycerin stearate (Sunsoft Q-18B = monoester content 35%: Taiyo Kagaku) The product was added to 95 g (95% by weight) and mixed for 5 minutes with propeller stirring. A transparent liquid antioxidant composition could be obtained. It is in a good state as an antioxidant composition.
実施例3
カテキン(サンフェノン100S=カテキン含量90重量%:太陽化学(株)製)10g(10重量%)を70℃に溶解したジグリセリンオレイン酸エステル(ポエム DO−100V=モノエステル含量80%:理研ビタミン(株)製)90g(90重量%)に添加して、プロペラ撹拌にて10分間混合した。透明な液状の抗酸化剤組成物を得ることができた。抗酸化剤組成物として良好な状態である。Example 3
Catechin (Sanphenone 100S = catechin content 90% by weight: manufactured by Taiyo Kagaku Co., Ltd.) 10 g (10% by weight) dissolved in diglycerin oleate (Poem DO-100V = monoester content 80%: RIKEN vitamins) The product was added to 90 g (90% by weight) and mixed for 10 minutes with propeller stirring. A transparent liquid antioxidant composition could be obtained. It is in a good state as an antioxidant composition.
実施例4
カテキン(サンフェノン100S=カテキン含量90重量%:太陽化学(株)製)20g(20重量%)を60℃に溶解したジグリセリンラウリン酸エステル(ポエム DL−100=モノエステル含量80%:理研ビタミン(株)製)80g(80重量%)に添加して、プロペラ撹拌にて5分間混合した。透明な液状の抗酸化剤組成物を得ることができた。抗酸化剤組成物として良好な状態である。Example 4
Catechin (Sanphenone 100S = catechin content 90% by weight: manufactured by Taiyo Kagaku Co., Ltd.) 20 g (20% by weight) dissolved in diglycerin laurate (Poem DL-100 = monoester content 80%: RIKEN vitamins) The product was added to 80 g (80% by weight) and mixed for 5 minutes with propeller stirring. A transparent liquid antioxidant composition could be obtained. It is in a good state as an antioxidant composition.
実施例5
カテキン(ポリフェノン60A=カテキン含量60重量%:三井農林(株)製)10g(10重量%)を60℃に溶解したジグリセリンオレイン酸エステル(ポエム DO−100V=モノエステル含量80%:理研ビタミン(株)製)90g(90重量%)に添加して、プロペラ撹拌にて10分間混合した。透明な液状の抗酸化剤組成物を得ることができた。抗酸化剤組成物として良好な状態である。Example 5
Catechin (polyphenone 60A = catechin content 60% by weight: manufactured by Mitsui Norin Co., Ltd.) 10 g (10% by weight) dissolved in diglycerin oleate (Poem DO-100V = monoester content 80%: RIKEN vitamins) The product was added to 90 g (90% by weight) and mixed for 10 minutes with propeller stirring. A transparent liquid antioxidant composition could be obtained. It is in a good state as an antioxidant composition.
実施例6
カテキン(ポリフェノン60A=カテキン含量60重量%:三井農林(株)製)1g(1重量%)を60℃に溶解したジグリセリンオレイン酸エステル(ポエム DO−100V=モノエステル含量80%:理研ビタミン(株)製)99g(99重量%)に添加して、プロペラ撹拌にて10分間混合した。透明な液状の抗酸化剤組成物を得ることができた。抗酸化剤組成物として良好な状態である。Example 6
Catechin (polyphenone 60A = catechin content 60% by weight: manufactured by Mitsui Norin Co., Ltd.) 1 g (1% by weight) dissolved in diglycerin oleate (Poem DO-100V = monoester content 80%: RIKEN vitamin ( 99 g (99% by weight) and mixed for 10 minutes with propeller stirring. A transparent liquid antioxidant composition could be obtained. It is in a good state as an antioxidant composition.
比較例1
カテキン(ポリフェノン60A=カテキン含量60重量%:三井農林(株)製)0.5Kg(5重量%)を60℃に加熱した大豆油9.5Kg(95重量%)に添加して、プロペラ撹拌にて10分間混合した。カテキンが溶解せず沈殿した。抗酸化剤組成物として不適な状態である。Comparative Example 1
Catechin (Polyphenone 60A = Catechin content 60 wt%: Mitsui Norin Co., Ltd.) 0.5 kg (5 wt%) was added to soybean oil 9.5 kg (95 wt%) heated to 60 ° C., and propeller stirring was performed. And mixed for 10 minutes. Catechin was not dissolved but precipitated. This is an unsuitable state as an antioxidant composition.
比較例2
カテキン(ポリフェノン60A=カテキン含量60重量%:三井農林(株)製)5g(5重量%)を60℃に溶解したグリセリンオレイン酸エステル(エマルジー MO:理研ビタミン(株)製)95g(95重量%)に添加して、プロペラ撹拌にて10分間混合した。カテキンが溶解せず分離した。抗酸化剤組成物として不適な状態である。Comparative Example 2
Catechin (polyphenone 60A = catechin content 60% by weight: manufactured by Mitsui Norin Co., Ltd.) 5 g (5% by weight) dissolved in glycerin oleate (Emulsy MO: manufactured by Riken Vitamin Co., Ltd.) 95 g (95% by weight) And mixed for 10 minutes with propeller stirring. Catechin was not dissolved and separated. This is an unsuitable state as an antioxidant composition.
比較例3
カテキン(サンフェノン100S=カテキン含量90重量%:太陽化学(株)製)10g(10重量%)を70℃に溶解したポリグリセリン縮合リシノレイン酸エステル(サンソフト 818H:太陽化学(株)製)90g(90重量%)に添加して、プロペラ撹拌にて10分間混合した。不透明な液状のものを得た。しばらく保管すると沈殿が発生した。抗酸化剤組成物として不適な状態である。Comparative Example 3
90 g of polyglycerin condensed ricinoleic acid ester (Sunsoft 818H: manufactured by Taiyo Kagaku Co., Ltd.) in which 10 g (10 wt%) of catechin (Sanphenon 100S = catechin content 90 wt%: manufactured by Taiyo Chemical Co., Ltd.) was dissolved at 70 ° C. 90% by weight) and mixed for 10 minutes with propeller stirring. An opaque liquid was obtained. Precipitation occurred after storage for a while. This is an unsuitable state as an antioxidant composition.
比較例4
カテキン(サンフェノン100S=カテキン含量90重量%:太陽化学(株)製)20g(20重量%)を60℃に溶解した大豆レシチン(辻製油(株)製)80g80重量%に添加して、プロペラ撹拌にて10分間混合した。不透明なペースト状のものを得た。抗酸化剤組成物として不適な状態である。Comparative Example 4
Catechin (Sanphenon 100S = Catechin content 90 wt%: Taiyo Kagaku Co., Ltd.) 20 g (20 wt%) was added to soybean lecithin (Tsubame Oil Co., Ltd.) 80 g 80 wt% dissolved in 60 ° C., and propeller stirring For 10 minutes. An opaque paste was obtained. This is an unsuitable state as an antioxidant composition.
比較例5
カテキン(ポリフェノン60A=カテキン含量60重量%:三井農林(株)製)10g(10重量%)を80℃に溶解したポリグリセリンオレイン酸エステル(MO−3S:阪本薬品(株)製)90g(90重量%)に添加して、プロペラ撹拌にて5分間混合した。不透明な液状のものを得た。抗酸化剤組成物として不適な状態である。
〔比較試験1〕Comparative Example 5
90 g of polyglycerol oleate (MO-3S: manufactured by Sakamoto Yakuhin Co., Ltd.) in which 10 g (10 wt%) of catechin (polyphenone 60A = catechin content: 60% by weight: manufactured by Mitsui Norin Co., Ltd.) was dissolved at 80 ° C. And mixed for 5 minutes with propeller stirring. An opaque liquid was obtained. This is an unsuitable state as an antioxidant composition.
[Comparison test 1]
実施例1〜5、比較例1〜5で得られた抗酸化剤組成物の油脂への溶解性を評価するために、抗酸化剤組成物をカテキン添加量が100PPMとなるように菜種サラダ油に添加・混合してその状態を比較した。更に、25℃で12か月間保存したときの状態を比較した。結果を表1に示す。
〔比較試験2〕
比較試験1で調整した、抗酸化組成物を添加した菜種サラダ油の抗酸化性をAOM試験法(基準油脂分析試験法2.4.28.1−81)に基づいて測定した。比較例6として抗酸化剤組成物無添加の菜種サラダ油を試験した。結果を表1に示す。In order to evaluate the solubility of the antioxidant compositions obtained in Examples 1 to 5 and Comparative Examples 1 to 5 in fats and oils, the antioxidant composition was added to rapeseed salad oil so that the catechin addition amount was 100 PPM. The state was compared by adding and mixing. Furthermore, the state when it preserve | saved at 25 degreeC for 12 months was compared. The results are shown in Table 1.
[Comparison test 2]
Antioxidant property of the rapeseed salad oil prepared by the comparative test 1 to which the antioxidant composition was added was measured based on the AOM test method (standard oil analysis test method 2.4.28.1-81). As Comparative Example 6, rapeseed salad oil to which no antioxidant composition was added was tested. The results are shown in Table 1.
表1から明らかなように、本発明の抗酸化剤組成物は、カテキン類が均一に溶解されており、その結果油脂へ添加した場合でも、濁ることなく透明に溶解する。さらには、油脂に添加した際の抗酸化効果も優れていることがわかる。 As is clear from Table 1, 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.
〔比較試験3〕
実施例1、2で得られた抗酸化剤組成物の魚油に対する抗酸化性試験を行った。魚油99.8gに対して、0.2gの抗酸化剤組成物を添加し(カテキンとして魚油に対して100PPM添加)混合した。無添加及び0.02%トコフェロール添加区を対照として、25℃恒温槽中で保管後、過酸化物価を測定して比較した。試験開始時の魚油の過酸化物価は0.5であった。結果を表2に示す。[Comparative test 3]
The antioxidant property test with respect to the fish oil of the antioxidant composition obtained in Examples 1 and 2 was performed. 0.2g of the antioxidant composition was added to 99.8g of fish oil (100PPM added to fish oil as catechin) and mixed. Using the additive-free and 0.02% tocopherol-added sections as controls, the peroxide values were measured and compared after storage in a constant temperature bath at 25 ° C. The peroxide value of fish oil at the start of the test was 0.5. The results are shown in Table 2.
表2から明らかなように、実施例1,2の抗酸化剤組成物を添加した魚油は保存後も過酸化物価が上昇せず、本発明の抗酸化剤組成物の抗酸化性が優れていることがわかる。 As apparent from Table 2, the fish oil to which the antioxidant compositions of Examples 1 and 2 were added did not increase the peroxide value after storage, and the antioxidant composition of the present invention was excellent in antioxidant properties. I understand that.
実施例7
実施例1で調整した抗酸化剤組成物1Kg(0.1重量%)をコーン油999Kg(99.9重量%)に添加混合して5ガロン缶に、16.5Kg入り目で充填した。濁りのない液状油を得ることができた。臭い、色も良好であった。調整時の過酸化物価は0.2であった。
このコーン油を37℃の恒温室に6ヶ月間保管後、その状態を検査したところ、臭い、色の変化はなく、過酸化物価の測定結果は0.5であった。
本発明の抗酸化剤組成物を含有する油脂は優れた品質であることがわかる。
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.
Claims (2)
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015037381A JP5786215B1 (en) | 2015-02-09 | 2015-02-09 | Antioxidant composition and fats and oils to which it is added |
PCT/JP2016/053876 WO2016129611A1 (en) | 2015-02-09 | 2016-02-01 | Antioxidant composition and oil having same added thereto |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2015037381A JP5786215B1 (en) | 2015-02-09 | 2015-02-09 | Antioxidant composition and fats and oils to which it is added |
Publications (2)
Publication Number | Publication Date |
---|---|
JP5786215B1 true JP5786215B1 (en) | 2015-09-30 |
JP2016145309A JP2016145309A (en) | 2016-08-12 |
Family
ID=54207163
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2015037381A Active JP5786215B1 (en) | 2015-02-09 | 2015-02-09 | Antioxidant composition and fats and oils to which it is added |
Country Status (2)
Country | Link |
---|---|
JP (1) | JP5786215B1 (en) |
WO (1) | WO2016129611A1 (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018016776A (en) * | 2016-07-29 | 2018-02-01 | ミヨシ油脂株式会社 | Antioxidant, oil-and-fat composition containing antioxidant and oily food product containing the same |
JP7151979B1 (en) | 2022-04-27 | 2022-10-12 | 株式会社Ftt | Antioxidant composition and edible oil |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP3358225B2 (en) * | 1993-03-02 | 2002-12-16 | 日本油脂株式会社 | Water-soluble compound oil-solubilized preparation and production method thereof |
JP2001131572A (en) * | 1999-10-29 | 2001-05-15 | Riken Vitamin Co Ltd | Antioxidant composition and oil and fat composition |
JP5086634B2 (en) * | 2006-12-28 | 2012-11-28 | 三井農林株式会社 | Method for inhibiting coloration of fats and oils containing catechins |
EP2163252A4 (en) * | 2007-05-17 | 2012-01-11 | Kaneka Corp | Composition containing licorice-derived polyphenol |
JP5442315B2 (en) * | 2009-05-08 | 2014-03-12 | ツヤック株式会社 | Rust preventive, rust preventive treatment method and removal method thereof |
-
2015
- 2015-02-09 JP JP2015037381A patent/JP5786215B1/en active Active
-
2016
- 2016-02-01 WO PCT/JP2016/053876 patent/WO2016129611A1/en active Application Filing
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2018016776A (en) * | 2016-07-29 | 2018-02-01 | ミヨシ油脂株式会社 | Antioxidant, oil-and-fat composition containing antioxidant and oily food product containing the same |
JP7151979B1 (en) | 2022-04-27 | 2022-10-12 | 株式会社Ftt | Antioxidant composition and edible oil |
JP2023162573A (en) * | 2022-04-27 | 2023-11-09 | 株式会社Ftt | Antioxidant composition, and edible oil and fat |
Also Published As
Publication number | Publication date |
---|---|
JP2016145309A (en) | 2016-08-12 |
WO2016129611A1 (en) | 2016-08-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6027749B2 (en) | Oil-soluble antioxidant and method for producing the same | |
JP5652557B2 (en) | Edible oil and fat, food containing the same, and method for producing the same | |
CN105636450B (en) | Oil and fat containing polyvalent unsaturated fatty acid | |
CA2734477C (en) | Antioxidant composition for marine oils comprising tocopherol, rosemary extract, ascorbic acid and green tea extract, said green tea extract comprising a polysaccharide carrier | |
EP3290499B1 (en) | Method for manufacturing long chain polyunsaturated fatty acid-containing fat | |
EP2070429A1 (en) | Oxidative stabilisation of sterols and sterol esters | |
TWI678157B (en) | Fat and/or oil composition for heat cooking and method of preparing same, and method of preventing deterioration of fat and/or oil for heat cooking caused by heating | |
JP5786215B1 (en) | Antioxidant composition and fats and oils to which it is added | |
EP3213640B1 (en) | Long-chain polyunsaturated fatty-acid-containing fat and food containing same | |
CN106889206B (en) | Special oil for frying | |
JP6689049B2 (en) | Oil and fat composition for cooking and method for producing the same, and method for suppressing deterioration of oil and fat for cooking by heating | |
JP6746212B2 (en) | Method for producing oil and fat composition for heating cooking, method for suppressing deterioration of oil and fat for heating cooking by heating, oil and fat composition for heating cooking, and oil and fat composition containing high tocopherol | |
TW201813512A (en) | Fat and/or oil composition for heat cooking and method of preparing same, and method of preventing deterioration of fat and/or oil for heat cooking caused by heating | |
WO2023210454A1 (en) | Antioxidant composition, and edible oil and fat | |
CN107645910A (en) | The list of omega-3 fatty acid emulsion and two glyceride | |
JP6304451B2 (en) | Oil composition for coffee cream | |
KR20220053573A (en) | oil composition | |
JP6785083B2 (en) | Antioxidants, fat and oil compositions containing antioxidants and oily foods containing them | |
EP3940048A1 (en) | Oil/fat composition | |
JP2023137660A (en) | Method of producing anti-oxidizing agent for fat and oil-soluble functional component | |
JP6461471B2 (en) | Dairy products with reduced oxidative degradation | |
JP2024018136A (en) | Composition for preventing discoloration due to heating |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20150630 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20150703 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 5786215 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |