JP2774063B2 - Antioxidant composition - Google Patents
Antioxidant compositionInfo
- Publication number
- JP2774063B2 JP2774063B2 JP5347851A JP34785193A JP2774063B2 JP 2774063 B2 JP2774063 B2 JP 2774063B2 JP 5347851 A JP5347851 A JP 5347851A JP 34785193 A JP34785193 A JP 34785193A JP 2774063 B2 JP2774063 B2 JP 2774063B2
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- JP
- Japan
- Prior art keywords
- antioxidant
- present
- biphenyl compound
- biphenyl
- test
- 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.)
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- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Anti-Oxidant Or Stabilizer Compositions (AREA)
- Fats And Perfumes (AREA)
Description
【発明の詳細な説明】DETAILED DESCRIPTION OF THE INVENTION
【０００１】[0001]
【産業上の利用分野】本発明は、下記一般式化２The present invention relates to the following general formula 2:
【０００２】[0002]
【化２】 Embedded image
【０００３】（但しＲは炭素数１から８の直鎖および分
岐鎖状の飽和炭化水素基もしくはＣＨ2 ＯＨ、Ｃ3 Ｈ6
ＯＨ、ＣＨＯ、ＣＯＣＨ3 基）(Where R is a linear or branched saturated hydrocarbon group having 1 to 8 carbon atoms, CH 2 OH, C 3 H 6
OH, CHO, COCH 3 groups)
【０００４】で表されるビフェニル化合物の一種以上を
有効成分として含有する抗酸化組成物に関する。[0004] The present invention relates to an antioxidant composition containing one or more of the biphenyl compounds represented by the formula (1) as an active ingredient.
【０００５】[0005]
【従来の技術及び発明が解決しようとする課題】従来よ
り、食品、皮膚化粧料や医薬品にＢＨＴやＢＨＡ等の合
成抗酸化剤、α−トコフェロールやアスコルビン酸等の
抗酸化剤が用いられている。しかしながら、ＢＨＴやＢ
ＨＡ等の合成抗酸化剤は、安全性の点において問題にな
りつつある。また、α−トコフェロールやアスコルビン
酸等は安定性の面で問題を有している。これらのことか
ら、新規な抗酸化剤を探索する目的で、種々の植物抽出
物の抗酸化能について検討がされているが、その効果成
分の構造は不明である場合が多い（特開平５−１７０６
５８号公報）。また、その有効成分について検討がなさ
れている香辛料からの抽出物は特有の香り、色、味を有
しているものが多いことから食品や医薬品等への利用範
囲が制約されている（食品工業、４月号、２０頁、１９
９２年）。2. Description of the Related Art Conventionally, synthetic antioxidants such as BHT and BHA and antioxidants such as α-tocopherol and ascorbic acid have been used in foods, skin cosmetics and pharmaceuticals. . However, BHT and B
Synthetic antioxidants such as HA are becoming problematic in terms of safety. Further, α-tocopherol, ascorbic acid and the like have a problem in stability. In view of the above, the antioxidant ability of various plant extracts has been studied for the purpose of searching for a novel antioxidant, but the structure of the effect component is often unknown (Japanese Unexamined Patent Application Publication No. Hei. 1706
No. 58). In addition, the extracts from spices whose active ingredients are being studied are often those having unique scents, colors, and tastes, which limits the range of use for foods and pharmaceuticals (food industry). April issue, page 20, 19
1992).
【０００６】また、皮膚化粧料等への利用に於いては有
効成分の多くがフェノール構造を有し、アレルギー性皮
膚炎（感作性）を誘発する可能性が高いことや安定性に
問題があることから、ほとんど利用されていない。[0006] Further, when used in skin cosmetics and the like, many of the active ingredients have a phenolic structure, and have a high possibility of inducing allergic dermatitis (sensitization) and have a problem in stability. For some reason, it is hardly used.
【０００７】本発明に使用されるビフェニル化合物には
公知の物質も含まれているが、Ｊ．Ｃ．Ｐｅｗらの方法
により容易に合成することが可能である（ジャーナル
オブオーガニック ケミストリィ、第２８巻、１０４８
頁、１９６３年）。The biphenyl compound used in the present invention includes known substances. C. It can be easily synthesized by the method of Pew et al. (Journal
Of Organic Chemistry, Vol. 28, 1048
P. 1963).
【０００８】本発明に使用されるビフェニル化合物には
香料用保留剤、メラニン生成抑制剤としての用途に用い
られている化合物も含まれている（特願平３−３８０９
８号、特願平４−３２２７６１号）が、それらの化合物
が抗酸化効果を有していることは特に記載されていな
い。The biphenyl compounds used in the present invention also include compounds used for use as flavor retention agents and melanin production inhibitors (Japanese Patent Application No. 3-3809).
No. 8, Japanese Patent Application No. 4-322762) does not specifically disclose that these compounds have an antioxidant effect.
【０００９】本発明者等は、従来技術の難点を解消せん
として鋭意検討を行った結果、後記特定のビフェニル化
合物はほとんど無味無臭であり、安全性が極めて高くか
つ優れた抗酸化力を有することを見いだし本発明を完成
した。The inventors of the present invention have conducted intensive studies to solve the problems of the prior art. As a result, the specific biphenyl compound described below is almost tasteless and odorless, has extremely high safety, and has excellent antioxidant power. And completed the present invention.
【００１０】[0010]
【課題を解決するための手段】即ち、本発明は、下記一
般式化３That is, the present invention provides the following general formula 3
【００１１】[0011]
【化３】 Embedded image
【００１２】（但しＲは炭素数１から８の直鎖および分
岐鎖状の飽和炭化水素基もしくはＣＨ2 ＯＨ、Ｃ3 Ｈ6
ＯＨ、ＣＨＯ、ＣＯＣＨ3 基）(Where R is a linear or branched saturated hydrocarbon group having 1 to 8 carbon atoms, CH 2 OH, C 3 H 6
OH, CHO, COCH 3 groups)
【００１３】で表されるビフェニル化合物の一種以上を
有効成分として含有する抗酸化組成物に関する。[0013] The present invention relates to an antioxidant composition containing at least one of the biphenyl compounds represented by the formula (1) as an active ingredient.
【００１４】本発明の抗酸化組成物は、上記記載のビフ
ェニル化合物の一種以上を油脂やエタノール等に溶解分
散して用いることができる。また、必要に応じてクエン
酸などの相乗効果成分等を含有してもよい。本発明の抗
酸化組成物は、魚油、ラード、大豆油、あまに油、コー
ン油、綿実油、パーム油などの動植物を原料とする油
脂、バター、マーガリン、マヨネーズ、ハム、ポテトチ
ップ、揚げせんべい、魚肉等の食品組成物や口紅、乳
液、クリーム等の皮膚化粧料や医薬品組成物等に添加し
て用いられる。その配合量（使用量）は、組成物の総量
を基準として一般的には大略０．００１〜５重量％が好
ましく、更に好ましくは０．０１〜１重量％である。The antioxidant composition of the present invention can be used by dissolving and dispersing at least one of the above-mentioned biphenyl compounds in fats and oils, ethanol and the like. Further, if necessary, a synergistic effect component such as citric acid may be contained. The antioxidant composition of the present invention, fish oil, lard, soybean oil, linseed oil, corn oil, cottonseed oil, fats and oils based on animals and plants such as palm oil, butter, margarine, mayonnaise, ham, potato chips, fried rice crackers, It is used by being added to food compositions such as fish meat, skin cosmetics such as lipstick, milky lotion and cream and pharmaceutical compositions. The compounding amount (use amount) is generally preferably about 0.001 to 5% by weight, more preferably 0.01 to 1% by weight, based on the total amount of the composition.
【００１５】本発明によれば、食品の味や香りを損なう
ことなく、食品組成物の安定性を高めることが可能とな
る。また、安全性に問題がないことから（感作性を有し
ない）皮膚化粧料や医薬品組成物等へも容易に配合で
き、その組成物の安定性を高めることが可能となる。以
上記載のごとく、その作用効果の特性は著しい。According to the present invention, it is possible to enhance the stability of a food composition without impairing the taste and aroma of the food. Further, since there is no problem in safety, it can be easily blended into a skin cosmetic or a pharmaceutical composition or the like (having no sensitization), and the stability of the composition can be enhanced. As described above, the characteristics of the operation and effect are remarkable.
【００１６】[0016]
【実施例】以下、実施例について説明する。実施例にお
けるビフェニル化合物の略称を表１に示す。なお、これ
らの化合物はほとんど無味無臭であった。Embodiments will be described below. Table 1 shows abbreviations of the biphenyl compounds in the examples. These compounds were almost tasteless and odorless.
【００１７】[0017]
【表１】 [Table 1]
【００１８】また、実施例に示す％は重量％を意味す
る。なお、安全性（感作性および急性毒性）、抗酸化力
等の試験方法は下記の通りである。Further,% shown in the examples means% by weight. Test methods for safety (sensitization and acute toxicity), antioxidant power, etc. are as follows.
【００１９】（１）感作性試験法 マキシミゼイションテストによりを試験した。体重３５
０〜４００g のハートレイ系モルモット（メス）の肩甲
骨上の４×６cmの皮膚を刈毛し、１列に３つの皮内注射
を次の順序にしたがって２列に行った。 フロイント コンプリート アジュバンド（Freund's
complete ajuvant ：以下ＦＣＡ溶液と略記する）を左
右２ケ所に０．０５mlずつ皮内注射した。 ビフェニル化合物等の試験サンプル１０％オリーブ油
溶液を左右２ケ所に０．０５mlずつ皮内注射した。 ビフェニル化合物等の試験サンプル２０％含有ＦＣＡ
溶液に同量の滅菌水を加え乳化した溶液を左右２ケ所に
０．０５ｍｌ皮内注射した。 これらの操作６日後に同じ部位を刈毛し、１０％ラウリ
ル硫酸ソーダ含有ワセリンを塗擦し、軽度の炎症を起こ
させた。塗擦２４時間後に同部位にビフェニル化合物等
の試験サンプル１０％オリーブ油溶液０．２mlをガーゼ
に塗布して、４８時間閉塞貼付した。皮内注射後２１日
目に腹側部を刈毛し、ビフェニル化合物等の試験サンプ
ル５％、１０％各オリーブ油溶液を２４時間閉塞貼付し
た。判定は、２４時間後と４８時間後に表２に示した評
価基準にしたがって肉眼により行った。(1) Sensitization test method The test was carried out by a maximization test. Weight 35
A 4 × 6 cm skin on the scapula of a 0-400 g Hartley guinea pig (female) was shaved and three intradermal injections were made in one row in two rows according to the following sequence. Freund's Complete Adjuvant (Freund's
complete ajuvant: hereinafter, abbreviated as FCA solution) was injected intradermally into each of the right and left two places in an amount of 0.05 ml. A 10% olive oil solution of a test sample, such as a biphenyl compound, was injected intradermally into 0.05 ml of the left and right two portions. FCA containing 20% of test sample such as biphenyl compound
The same amount of sterile water was added to the solution and 0.05 ml of the emulsified solution was injected intradermally into two places on the left and right. Six days after these operations, the same site was shaved and rubbed with petrolatum containing 10% sodium lauryl sulfate to cause slight inflammation. Twenty-four hours after the application, 0.2 ml of a 10% olive oil solution of a test sample such as a biphenyl compound was applied to the gauze at the same site, and the occlusion was applied for 48 hours. On the 21st day after the intradermal injection, the abdomen was shaved, and a 5% and 10% olive oil solution of a test sample such as a biphenyl compound was occluded and applied for 24 hours. The judgment was made visually after 24 hours and 48 hours according to the evaluation criteria shown in Table 2.
【００２０】[0020]
【表２】 [Table 2]
【００２１】（２）急性毒性試験法 経口投与による限度試験を実施した。ＩＣＲ系マウス
（オス、６週齢、体重２８〜３４g ）１群１０匹に対
し、本発明品の１０％オリーブ油溶液を２g/kg経口投与
し、２週間、毎日症状および死亡例を観察した。(2) Acute toxicity test method A limit test by oral administration was carried out. To a group of 10 ICR mice (male, 6 weeks old, body weight 28-34 g), a 10% olive oil solution of the present invention was orally administered at 2 g / kg, and symptoms and deaths were observed daily for 2 weeks.
【００２２】（３）抗酸化力試験法 食品分析試験法に記載の過酸化物価（ＰＯＶ値）を用い
て、本発明のビフェニル化合物の抗酸化能を評価した。
不飽和脂肪酸としてオレイン酸メチル、リノール酸メチ
ルおよび紅花油を試験試料に用い、太陽光照射および１
００℃での加熱を過酸化条件とした。また、一般的に抗
酸化剤として用いられているＢＨＴ（ブチルヒドロキシ
トルエン）、ビタミン−Ｅ（α−トコフェロール）を比
較試料として用いた。(3) Antioxidant power test method The antioxidant ability of the biphenyl compound of the present invention was evaluated using the peroxide value (POV value) described in the food analysis test method.
Methyl oleate, methyl linoleate and safflower oil were used as the unsaturated fatty acids in the test samples,
Heating at 00 ° C. was made the peroxidation condition. In addition, BHT (butylhydroxytoluene) and vitamin-E (α-tocopherol), which are generally used as antioxidants, were used as comparative samples.
【００２３】実施例１ 本発明で用いるビフェニル化合物について前記感作性の
試験方法に従い、安全性について検討した。その結果を
表３に示す。Example 1 The safety of the biphenyl compound used in the present invention was examined in accordance with the test method for sensitization described above. Table 3 shows the results.
【００２４】[0024]
【表３】 注）ＰＲ；感作率（陽性動物数／使用動物数） ＭＲ；反応評点の平均値[Table 3] Note) PR; sensitization rate (number of positive animals / number of animals used) MR; average value of response scores
【００２５】表３に示す如く、本発明で用いるビフェニ
ル化合物には感作性は認められなかった。As shown in Table 3, no sensitization was observed in the biphenyl compound used in the present invention.
【００２６】実施例２ 本発明で用いるビフェニル化合物について前記急性毒性
試験を実施した。その結果を表４に示す。Example 2 The acute toxicity test was performed on the biphenyl compound used in the present invention. Table 4 shows the results.
【００２７】[0027]
【表４】 [Table 4]
【００２８】表４に示す如く、本発明品に異常および死
亡例は認められなかった。As shown in Table 4, no abnormalities or deaths were found in the product of the present invention.
【００２９】実施例３ リノール酸メチルに抗酸化試験試料をそれぞれ０．３重
量％添加し、１００℃にて加熱による脂質過酸化度を前
記抗酸化試験方法を用いて検討した。その結果、図１に
示すように本発明で用いるビフェニル化合物３は優れた
抗酸化力を有していることが確認された。Example 3 An antioxidant test sample was added to methyl linoleate in an amount of 0.3% by weight, and the degree of lipid peroxidation by heating at 100 ° C. was examined using the above-described antioxidant test method. As a result, as shown in FIG. 1, it was confirmed that the biphenyl compound 3 used in the present invention had excellent antioxidant power.
【００３０】実施例４ オレイン酸メチルに抗酸化試験試料をそれぞれ０．１及
び０．５重量％添加し、太陽光照射による脂質過酸化度
を前記抗酸化試験方法を用いて検討した。その結果、図
２に示すように本発明で用いるビフェニル化合物１は優
れた抗酸化力を有していることが確認された。Example 4 Antioxidant test samples were added to methyl oleate in amounts of 0.1 and 0.5% by weight, respectively, and the degree of lipid peroxidation by irradiation with sunlight was examined using the above-described antioxidant test method. As a result, as shown in FIG. 2, it was confirmed that the biphenyl compound 1 used in the present invention had an excellent antioxidant power.
【００３１】実施例５ 紅花油に抗酸化試験試料をそれぞれ０．３重量％添加
し、太陽光照射による脂質過酸化度を前記抗酸化試験方
法を用いて検討した。その結果、図３に示すように本発
明で用いるビフェニル化合物２及び５は優れた抗酸化力
を有していることが確認された。Example 5 Each antioxidant test sample was added to safflower oil in an amount of 0.3% by weight, and the degree of lipid peroxidation due to sunlight irradiation was examined using the above-described antioxidant test method. As a result, as shown in FIG. 3, it was confirmed that the biphenyl compounds 2 and 5 used in the present invention had excellent antioxidant power.
【００３２】実施例６ 紅花油に抗酸化試験試料をそれぞれ０．３重量％添加
し、１００℃にて加熱による脂質過酸化度を前記抗酸化
試験方法を用いて検討した。その結果、図４に示すよう
に本発明で用いるビフェニル化合物１は優れた抗酸化力
を有していることが確認された。Example 6 An antioxidant test sample was added to safflower oil in an amount of 0.3% by weight, and the degree of lipid peroxidation by heating at 100 ° C. was examined using the antioxidant test method. As a result, as shown in FIG. 4, it was confirmed that the biphenyl compound 1 used in the present invention had an excellent antioxidant power.
【００３３】[0033]
【発明の効果】本発明で用いるビフェニル化合物は、ほ
とんど無味無臭であり安全性が極めて高いことから食
品、皮膚化粧料および医薬品組成物に対して汎用性が高
く、かつ優れた抗酸化能を有する。The biphenyl compound used in the present invention is almost tasteless and odorless and has extremely high safety, so that it is highly versatile for foods, skin cosmetics and pharmaceutical compositions and has excellent antioxidant ability. .
【図１】リノール酸メチルに対するビフェニル化合物３
の抗酸化力を示す。FIG. 1: Biphenyl compound 3 for methyl linoleate
Shows the antioxidant power of
【図２】オレイン酸メチルに対するビフェニル化合物１
の抗酸化力を示す。FIG. 2 Biphenyl compound 1 for methyl oleate
Shows the antioxidant power of
【図３】紅花油に対するビフェニル化合物２および５の
抗酸化力を示す。FIG. 3 shows the antioxidant power of biphenyl compounds 2 and 5 against safflower oil.
【図４】紅花油に対するビフェニル化合物１の抗酸化力
を示す。FIG. 4 shows the antioxidant power of biphenyl compound 1 against safflower oil.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.6，ＤＢ名) C09K 15/08 A61K 7/00 A61K 47/06 C11B 5/00 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)──────────────────────────────────────────────────続 き Continued on the front page (58) Field surveyed (Int. Cl. 6 , DB name) C09K 15/08 A61K 7/00 A61K 47/06 C11B 5/00 CA (STN) REGISTRY (STN)
Claims (1)
炭化水素基もしくはＣＨ2 ＯＨ、Ｃ3 Ｈ6 ＯＨ、ＣＨ
Ｏ、ＣＯＣＨ3 基）で表されるビフェニル化合物の一種
以上を有効成分として含有することを特徴とする抗酸化
組成物。[Claim 1] The following general formula: (Where R is a linear or branched saturated hydrocarbon group having 1 to 8 carbon atoms or CH 2 OH, C 3 H 6 OH, CH
An antioxidant composition comprising, as an active ingredient, at least one of biphenyl compounds represented by O, COCH 3 groups).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5347851A JP2774063B2 (en) | 1993-12-24 | 1993-12-24 | Antioxidant composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5347851A JP2774063B2 (en) | 1993-12-24 | 1993-12-24 | Antioxidant composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07179853A JPH07179853A (en) | 1995-07-18 |
| JP2774063B2 true JP2774063B2 (en) | 1998-07-09 |
Family
ID=18393035
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5347851A Expired - Fee Related JP2774063B2 (en) | 1993-12-24 | 1993-12-24 | Antioxidant composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2774063B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5763496A (en) * | 1995-11-27 | 1998-06-09 | The Research Foundation Of State University Of New York | Prevention of atherosclerosis using NADPH oxidase inhibitors |
| JP3632162B2 (en) * | 1997-01-14 | 2005-03-23 | 株式会社カネボウ化粧品 | Skin cosmetics |
| DE10310204A1 (en) * | 2003-03-08 | 2004-09-16 | Symrise Gmbh & Co. Kg | Use of divanillin as a flavoring |
-
1993
- 1993-12-24 JP JP5347851A patent/JP2774063B2/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| JPH07179853A (en) | 1995-07-18 |
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