JPS59204696A - Antioxidant - Google Patents

Antioxidant

Info

Publication number
JPS59204696A
JPS59204696A JP7836383A JP7836383A JPS59204696A JP S59204696 A JPS59204696 A JP S59204696A JP 7836383 A JP7836383 A JP 7836383A JP 7836383 A JP7836383 A JP 7836383A JP S59204696 A JPS59204696 A JP S59204696A
Authority
JP
Japan
Prior art keywords
antioxidant
oil
phytic acid
fats
oils
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.)
Pending
Application number
JP7836383A
Other languages
Japanese (ja)
Inventor
大道寺 恒
良一 塚原
敏夫 遠藤
宮内 臣信
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.)
MITSUI SEIYAKU KOGYO KK
Original Assignee
MITSUI SEIYAKU KOGYO KK
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 MITSUI SEIYAKU KOGYO KK filed Critical MITSUI SEIYAKU KOGYO KK
Priority to JP7836383A priority Critical patent/JPS59204696A/en
Publication of JPS59204696A publication Critical patent/JPS59204696A/en
Pending legal-status Critical Current

Links

Landscapes

  • Anti-Oxidant Or Stabilizer Compositions (AREA)
  • Fats And Perfumes (AREA)

Abstract

(57)【要約】本公報は電子出願前の出願データであるた
め要約のデータは記録されません。
(57) [Summary] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

【発明の詳細な説明】 本発明は油脂、脂肪酸又はこれらを含有する製品に対し
て実用上極めて有効かつ安全な酸化防止剤に関する。
DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an antioxidant that is extremely effective and safe in practice for oils and fats, fatty acids, and products containing these.

油脂及び脂肪酸と食品中に含まれる油脂及び脂肪酸は空
気と接触して自動酸化が起り製品の品質低下を生じる。
Fats and oils and fatty acids contained in food products undergo auto-oxidation when they come into contact with air, resulting in a deterioration in the quality of the product.

この自動酸化を防止するには酸化防止剤の機能として過
酸化物を分解すると同時にその発生原因となる銅、鉄等
の油脂類に含まれる金属イオンを不活化する機會旨が必
要である。従来の酸化防止剤は一つの機能だけを有する
物が大部分であるが、今回両方の機能を有する酸化防止
剤の開発に成功し本発明を完成するに至った。
In order to prevent this autooxidation, it is necessary to decompose peroxide as an antioxidant and at the same time inactivate the metal ions contained in fats and oils such as copper and iron, which are the cause of its generation. Most conventional antioxidants have only one function, but we have now succeeded in developing an antioxidant that has both functions, leading to the completion of the present invention.

従来の酸化防止剤としてはBHA(ブチルヒドロキシア
ニソール)、BHT(ブチルヒドロキシトルエン)など
の合成酸化防止剤やトコフェロールなどの天然物系酸化
防止剤がある。これらはいずれも油脂類中に含有する金
属イオンを封殺する機能を有していない。さらに合成酸
化防止剤(BHA、BHT)は近年に至りその安全性が
問題となってきている。一方トコフエロールは抗酸化力
の点で不足しており又高価であり安全性が高く安価で効
果の高い酸化防止剤の登場が望まれている。
Conventional antioxidants include synthetic antioxidants such as BHA (butylated hydroxyanisole) and BHT (butylated hydroxytoluene), and natural antioxidants such as tocopherol. None of these have the function of sealing off metal ions contained in fats and oils. Furthermore, the safety of synthetic antioxidants (BHA, BHT) has become a problem in recent years. On the other hand, tocopherols lack antioxidant power and are expensive, so there is a desire for a safe, inexpensive, and highly effective antioxidant.

本発明の酸化防止剤は強い金属キレート化作用をもつ水
溶性のフィチン酸に乳化剤を加え、さらに油脂類を混合
し乳化せしめることにより調製する安定な油溶性乳化エ
マルジョンに関する。
The antioxidant of the present invention relates to a stable oil-soluble emulsion prepared by adding an emulsifier to water-soluble phytic acid, which has a strong metal chelating effect, and further mixing and emulsifying fats and oils.

この製品自体に強い酸化防止力が有るが、さらに油溶性
のdt−α−トコフェロール又は天然ビタミンE類を添
加しても良く又さらにビタミンCを添加しても良好な酸
化防止効果を示し又容 ゛易に油溶化する事ができた。
This product itself has a strong antioxidant effect, but it is also possible to add oil-soluble dt-α-tocopherol or natural vitamin E, and even when vitamin C is added, it shows a good antioxidant effect. It could be easily made oil-soluble.

又これにアミノ酸例えばトリプトファン、チロシン、リ
ジン、グリシン、セリン等を加えても良い。本酸化防止
剤は水に対しても分散性は良好であり一般食品中の油脂
及び脂肪酸の酸化防止効果も有すると考えられる。
Further, amino acids such as tryptophan, tyrosine, lysine, glycine, serine, etc. may be added to this. The present antioxidant has good dispersibility in water and is thought to have the effect of preventing the oxidation of fats and oils and fatty acids in general foods.

フィチン酸油溶化の先行技術としては、フィチン酸又は
その塩類とレシチンを混合する方法(%公昭47−45
401)があるかこの混合物は十分に油脂類に溶解し得
ない。又フィチン酸とソルビタン系脂肪酸エステル又は
グリセリン系脂肪酸エステルとを混合する方法(特公昭
56−15839)があるがこの混合物は調製後数日で
分離現象を生じ実用に適さない。すなわち表1に示した
ように調製後1日ないし4日で不可逆的に分離してしま
う。
As a prior art for phytic acid oil solubilization, there is a method of mixing phytic acid or its salts with lecithin (% Kosho 47-45
401) or this mixture cannot be sufficiently dissolved in fats and oils. There is also a method of mixing phytic acid and sorbitan fatty acid ester or glycerin fatty acid ester (Japanese Patent Publication No. 56-15839), but this mixture causes a separation phenomenon several days after preparation and is not suitable for practical use. That is, as shown in Table 1, it will irreversibly separate within 1 to 4 days after preparation.

表1 フィチン酸と各種乳化剤混合物 の安定性。Table 1 Phytic acid and various emulsifier mixtures stability.

後述のごとく、本発明者らは上記のよう々欠点を克服−
1すべく鋭意研究の結果フィチン酸と併用する乳化剤(
界面活性剤)を厳選しさらに油脂類を前もって混合乳化
せしめる事により極めめて安定で効果の強い酸化防止剤
の開発に成功した。
As will be described later, the present inventors have overcome the above-mentioned drawbacks.
1. As a result of intensive research, an emulsifier used in combination with phytic acid (
By carefully selecting surfactants and pre-mixing and emulsifying oils and fats, we succeeded in developing an extremely stable and highly effective antioxidant.

フィチン酸を用いた場合フィチン酸自体が油に溶解しな
いため、いかに均一に速くフィチン酸を油中に分酸溶解
せしめるかが酸化防止効力発現のだめのかなめである。
When phytic acid is used, phytic acid itself does not dissolve in oil, so the key to achieving antioxidant efficacy is how uniformly and quickly phytic acid can be dissolved in oil.

本発明のフィチン酸をあらかじめ油脂類と混合乳化せし
めた酸化防止剤は極めて安定かつ良好な状態で使用時に
分散乳化し長期にわたり分離を生じない。又本混合物に
ビタミンE、ビタミンC、アミノ酸等を加えても容易に
安定かつノ句−な乳化混合物を得る事が出来る。
The antioxidant of the present invention, which is prepared by mixing and emulsifying phytic acid with fats and oils in advance, is extremely stable and in a good condition, disperses and emulsifies during use, and does not separate over a long period of time. Furthermore, even if vitamin E, vitamin C, amino acids, etc. are added to this mixture, a stable and stable emulsified mixture can be easily obtained.

本発明においてフィチン酸とはフィチン酸自体及びその
金属塩類をいう。フィチン酸は自然界特に植物中に広く
存在する天然物でミオイノシトールへキザリン酸エステ
ルとなっている。
In the present invention, phytic acid refers to phytic acid itself and its metal salts. Phytic acid is a natural product that is widely present in nature, especially in plants, and is a myo-inositol to xalate ester.

本発明において油脂とはオレイン酸、リノール酸、リノ
ンイン酸等の不飽和脂肪酸類と綿実油、紅花油、ココナ
ツツ油、コーン油、大豆油。
In the present invention, fats and oils include unsaturated fatty acids such as oleic acid, linoleic acid, and linoneic acid, cottonseed oil, safflower oil, coconut oil, corn oil, and soybean oil.

ゴマ油、オリーブ油、落花生油、パーム油、牛脂、豚脂
、魚油、鯨油等の天然油脂を言う。
Refers to natural oils and fats such as sesame oil, olive oil, peanut oil, palm oil, beef tallow, lard, fish oil, and whale oil.

本発明において界面活性剤とはショ糖脂肪酸エステル、
フロピレンゲリコール、フロピレンゲリコールモノステ
アレート、レシチン、ソルビタントリオレエート、ソル
ビタンモノオレエート、グリセリンモノオレエート、ポ
リグリセリン縮合リシルイン酸エステル等を言う。
In the present invention, surfactants include sucrose fatty acid ester,
It refers to phlopylene gelicol, phlopylene gellicol monostearate, lecithin, sorbitan trioleate, sorbitan monooleate, glycerin monooleate, polyglycerin condensed lysyl inate, and the like.

以下実施例により説明する。This will be explained below using examples.

実施例1 酸化防止剤の乳化安定性 表2に示す種々の配合率に従い50%フィチン酸水溶液
に乳化剤としてポリグリセリン酸縮合リシルイン酸エス
テルを加え混合しさらに市販のザラダ油を加えて乳化せ
しめて酸化防止剤を調製しこれを常温にて30日間放置
しその安定性をみた。
Example 1 Emulsion stability of antioxidants Polyglyceric acid condensed lysyl phosphate was added as an emulsifier to a 50% phytic acid aqueous solution according to the various compounding ratios shown in Table 2, mixed, and commercially available salada oil was added to emulsify and oxidize. An inhibitor was prepared and left at room temperature for 30 days to examine its stability.

表2 酸化防止剤配合率と乳化安定性 表2に示し7たととく本酸化防止剤の乳化安定性は極め
て良好であった。
Table 2: Antioxidant blend ratio and emulsion stability As shown in Table 2, the emulsion stability of the present antioxidant was extremely good.

実施例2 酸化防止剤の酸化防止効果 実施例1に示した安定なフィチン酸乳化物の酸化防止効
果を調べた。
Example 2 Antioxidant effect of antioxidant The antioxidant effect of the stable phytic acid emulsion shown in Example 1 was investigated.

50%フィチン酸水溶液にポリグリセリン酸縮合すンル
イン酸エステルと市販のサラダ油を2:1:2の割合で
混合乳化せしめ酸化防止剤を調製した。
An antioxidant was prepared by mixing and emulsifying a 50% aqueous phytic acid solution with a polyglyceric acid condensation ester and a commercially available salad oil in a ratio of 2:1:2.

この酸化防止剤を精製ラード油に対しフィチン酸純品換
算として各0.01.0.02.0.05.0.10の
各重量係になるように均一に溶解しAOM法(Acti
ve Oxygen Method法)に準じて酸化防
止効果を調らべだ。
This antioxidant was uniformly dissolved in refined lard oil to a weight ratio of 0.01, 0.02, 0.05, 0.10 in terms of pure phytic acid.
ve Oxygen Method) to investigate the antioxidant effect.

2.33mj!/分の割合で乾燥空気を通気しながら9
7.8℃に加熱し酸化安定性試験を行いpovが100
に達するまでの時間を測定した。比較のため抗酸化剤で
あるdt−α−トコフエロールヲ精製ラうド油に対し単
独で0.05重重量部加した場合についても同様に試験
をした。
2.33mj! 9 while venting dry air at a rate of /min.
The oxidation stability test was performed by heating to 7.8℃ and the pov was 100.
The time taken to reach this point was measured. For comparison, a similar test was also conducted in which 0.05 parts by weight of dt-α-tocopherol, an antioxidant, was added alone to purified radish oil.

その結果を表3に示す。The results are shown in Table 3.

表3 酸化防止効果 0、1           24 無添加      8 dt−α−トコフェロール     o、o  5  
        20以上表3の結果よシ、フィチン酸
配合の本酸化防止剤はdt−α−トコフェロールと同等
又はそれ以上の酸化防止効果が認められた。
Table 3 Antioxidant effect 0, 1 24 No additive 8 dt-α-tocopherol o, o 5
According to the results in Table 3, this antioxidant containing phytic acid was found to have an antioxidant effect equal to or greater than that of dt-α-tocopherol.

実施例3 天然物系抗酸化剤との併用 50チフイテン酸水溶液にポリグリセリン酸縮合リシル
イン酸エステルと市販のサラダオイルとdt−α−トコ
フェロールとアスコルビン酸ヲそれぞれ==≠、30チ
、10係、#I、15%、10係の割合で混合し酸化防
止剤を調製した。この酸化防止剤を精製ラード油に重量
比でそれぞれ0.025.0.05係、0.1チ、0.
25%、添加し均一に溶解せしめAOM法にてPOVが
100に達する壕での時間を測定した。
Example 3 Combination with natural product antioxidants: 50% typhithenic acid aqueous solution, polyglyceric acid condensed lysyl phosphate, commercially available salad oil, dt-α-tocopherol, and ascorbic acid ==≠, 30%, 10%, respectively. An antioxidant was prepared by mixing #I, 15%, and 10 parts. The weight ratio of this antioxidant to refined lard oil is 0.025, 0.05, 0.1, and 0.0, respectively.
25% was added and dissolved uniformly, and the time required for the POV to reach 100 was measured using the AOM method.

比較のためdt−α−トコフェロールを0.05%添加
した場合も試験をした。
For comparison, a test was also conducted in which 0.05% of dt-α-tocopherol was added.

表4 酸化防止効果 0.025            24本発明の  
0.05    24 酸化防止剤   0.1       340.25 
            36無添加      8 dA−α−トコフェロール     0.05    
       20表4の結果より、本酸化防止剤の酸
化防止力はd/L−α−トコフェロール単独の場合やフ
ィチン酸単独よりさらに強い酸化防止効果が認められた
Table 4 Antioxidant effect 0.025 24 of the present invention
0.05 24 Antioxidant 0.1 340.25
36 No additive 8 dA-α-tocopherol 0.05
20 From the results in Table 4, the antioxidant effect of the present antioxidant was found to be stronger than that of d/L-α-tocopherol alone or phytic acid alone.

特許出願人  三井製薬工業株式会社Patent applicant: Mitsui Pharmaceutical Industries, Ltd.

Claims (1)

【特許請求の範囲】[Claims] フィチン酸及び/又はその塩を油脂中に乳化せしめた事
を特徴とする油脂類酸化防止剤。
An antioxidant for fats and oils characterized by emulsifying phytic acid and/or its salt in fats and oils.
JP7836383A 1983-05-06 1983-05-06 Antioxidant Pending JPS59204696A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP7836383A JPS59204696A (en) 1983-05-06 1983-05-06 Antioxidant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP7836383A JPS59204696A (en) 1983-05-06 1983-05-06 Antioxidant

Publications (1)

Publication Number Publication Date
JPS59204696A true JPS59204696A (en) 1984-11-20

Family

ID=13659913

Family Applications (1)

Application Number Title Priority Date Filing Date
JP7836383A Pending JPS59204696A (en) 1983-05-06 1983-05-06 Antioxidant

Country Status (1)

Country Link
JP (1) JPS59204696A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62153385A (en) * 1985-12-27 1987-07-08 Riken Vitamin Co Ltd Antioxidant
EP0326026A2 (en) * 1988-01-29 1989-08-02 BASF Aktiengesellschaft Stable mixture containing oxidation-sensitive compounds, process to obtain it and use of a combination of products to stabilize oxidation-sensitive compounds
EP0659347A1 (en) * 1993-12-20 1995-06-28 San-Ei Gen F.F.I., Inc. Stable emulsified compositions and foods containing the same
EP0841058A3 (en) * 1996-11-06 1999-09-01 Rhone-Poulenc Rorer Gmbh Phospholipid composition, method of making it and its use
US6278004B1 (en) 1996-11-06 2001-08-21 Aventis Pharma Deutschland Gmbh Stabilized phospholipidic composition
WO2005046349A3 (en) * 2003-11-14 2005-11-10 Aquanova Ger Solubilisate Tech Oleaginous composition containing a flowable active ingredient
CN109481725A (en) * 2018-12-12 2019-03-19 徐子寒 A kind of instant Glycyrrhiza Oil Compound dressing and preparation method thereof

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS62153385A (en) * 1985-12-27 1987-07-08 Riken Vitamin Co Ltd Antioxidant
JPH0464638B2 (en) * 1985-12-27 1992-10-15 Riken Vitamin Co
EP0326026A2 (en) * 1988-01-29 1989-08-02 BASF Aktiengesellschaft Stable mixture containing oxidation-sensitive compounds, process to obtain it and use of a combination of products to stabilize oxidation-sensitive compounds
EP0659347A1 (en) * 1993-12-20 1995-06-28 San-Ei Gen F.F.I., Inc. Stable emulsified compositions and foods containing the same
EP0841058A3 (en) * 1996-11-06 1999-09-01 Rhone-Poulenc Rorer Gmbh Phospholipid composition, method of making it and its use
US6100413A (en) * 1996-11-06 2000-08-08 Rhone-Poulenc Rorer Gmbh & Co. Method for the stabilization of a phospholipidic composition, method for the production of such a stabilized composition and its use
US6278004B1 (en) 1996-11-06 2001-08-21 Aventis Pharma Deutschland Gmbh Stabilized phospholipidic composition
WO2005046349A3 (en) * 2003-11-14 2005-11-10 Aquanova Ger Solubilisate Tech Oleaginous composition containing a flowable active ingredient
JP2007511213A (en) * 2003-11-14 2007-05-10 アクヴァノヴァ・ジャーマン・ソリュービリセイト・テクノロジーズ・(アーゲーテー)・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング Oily composition containing fluid active ingredients
CN109481725A (en) * 2018-12-12 2019-03-19 徐子寒 A kind of instant Glycyrrhiza Oil Compound dressing and preparation method thereof

Similar Documents

Publication Publication Date Title
JP3005226B2 (en) Method for producing antioxidant mixture
Judde et al. Antioxidant effect of soy lecithins on vegetable oil stability and their synergism with tocopherols
US3966632A (en) Vegetable oil emulsion
CA2128899C (en) Antioxidant system for powdered nutritional products
JP3113319B2 (en) Natural antioxidant composition
US9725675B2 (en) Lipid-soluble formulations containing mixtures of antioxidants
JPS59204696A (en) Antioxidant
JPS5944344B2 (en) antioxidant
CA2026448C (en) Spreads containing chlorophyll
JPS61127786A (en) Oil solubilizer
JPS62153385A (en) Antioxidant
JPS6231902B2 (en)
JP2905275B2 (en) Antioxidant composition
CA3180963A1 (en) Unsaturated fatty acid-containing water-in-oil type composition and method for producing same
WO1995005747A1 (en) Natural antioxidant system
JPS63309585A (en) Antioxidizing agent
JPS6312697A (en) Modification inhibitor of tocoherol
US2104242A (en) Composition of fatty matter and process of stabilizing same
Bickoff et al. Stabilization of carotene with nordihydroguaiaretic acid and other antioxidants
JPH0586368A (en) Antioxidant
JPS6012B2 (en) Mold release agent for confectionery and bread products
WO1996016140A1 (en) A natural antioxidant solution
JP2624694B2 (en) Edible water-in-oil type emulsified fat composition
JPH01202278A (en) Quality-retaining agent for food
JPS6178368A (en) Antioxidant for food