JP2731255B2 - Fragrance composition - Google Patents
Fragrance compositionInfo
- Publication number
- JP2731255B2 JP2731255B2 JP20758189A JP20758189A JP2731255B2 JP 2731255 B2 JP2731255 B2 JP 2731255B2 JP 20758189 A JP20758189 A JP 20758189A JP 20758189 A JP20758189 A JP 20758189A JP 2731255 B2 JP2731255 B2 JP 2731255B2
- Authority
- JP
- Japan
- Prior art keywords
- fragrance
- fragrance composition
- test
- present
- odor
- 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.)
- Expired - Fee Related
Links
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、デヒドロジオイゲノールを有効成分として
含有する芳香特性及び保留性に優れた香料組成物に関す
る。Description: TECHNICAL FIELD The present invention relates to a fragrance composition containing dehydrodieugenol as an active ingredient and having excellent aroma characteristics and retention properties.
〔従来の技術および発明が解決しようとする課題〕 従来より天然あるいは合成の有香物質を用いて優れた
香料を調香するときには所望の香気を持続するために、
有香物質の揮発性及び保留性を調整する各種保留剤が香
料に有効成分として配合し利用されている。具体的には
ベンジルサリシレート，ベンジルベンゾエート，トリエ
チルシトレート，イソプロピルミリステート，ジエチル
フタレート等が利用されている。しかしながら、ベンジ
ルサリシレートは接触皮膚アレルギー（以下感作性とい
う。）を起こすことが報告されている。（皮膚第23巻・
第４号・昭和56年８月、p421〜429,同431〜441等（また
上記の保留剤は、満足のいく保留効果をもつものではな
かった。[Problems to be solved by the prior art and the invention] Conventionally, when using a natural or synthetic scented substance to perfume an excellent fragrance, in order to maintain a desired scent,
Various retention agents for adjusting the volatility and retention of scented substances have been used as perfume as active ingredients. Specifically, benzyl salicylate, benzyl benzoate, triethyl citrate, isopropyl myristate, diethyl phthalate and the like are used. However, it has been reported that benzyl salicylate causes contact skin allergy (hereinafter referred to as sensitization). (Skin Volume 23
No. 4, August 1981, pp. 421-429, 431-441, etc. (The above-mentioned preservatives did not have a satisfactory reserving effect.
本発明者等は、従来技術の難点を解消せんと鋭意研究
を行った結果、デヒドロジオイゲノールが、香料の揮発
性及び保留性を調整する効果を有することを見いだし本
発明を完成した。The present inventors have conducted intensive studies to solve the problems of the prior art, and as a result, have found that dehydrodieugenol has an effect of adjusting the volatility and retention of perfume, and completed the present invention.
即ち、本発明は、 で表されるデヒドロジオイゲノールを含有することを特
徴とする香料組成物である。That is, the present invention It is a fragrance | flavor composition characterized by containing the dehydrodieugenol represented by these.
本発明に使用されるデヒドロジオイゲノールは公知の
物質であって、磯貝やディアズ等がすでにある種の植物
に微量であるが含まれることを報告している。（アグリ
カルチャー バイオロジカル ケミストリィ，第37巻４
号889−895頁,1973年、フォトケミストリィ，第19巻,68
1−682頁,1980年）しかしながら、これらに含まれる量
はごくわずかに少量であり、一般には、藤田等の方法
（日本化学雑誌第87巻第９号,110−112頁,1966年）など
により容易に入手することが可能である。The dehydrodieugenol used in the present invention is a known substance, and it has been reported that isoshellfish, diaz and the like are already contained in a certain plant in a small amount. (Agriculture Biological Chemistry, Vol. 37, No. 4
No. 889-895, 1973, Photochemistry, Volume 19, 68
However, the amount contained in these is very small, and is generally the same as the method of Fujita et al. (Nippon Kagaku Magazine Vol. 87, No. 9, pp. 110-112, 1966). Can be obtained more easily.
本発明で用いるデヒドロジオイゲノールは皮膚刺激や
感作性がなく安全、かつ通常の香料組成物に易溶であ
り、その配合量（使用量）は、香料組成物の総量を基準
として一般的には、大略0.5〜10重量％、好ましくは1.0
〜5.0重量％である。The dehydrodieugenol used in the present invention has no skin irritation or sensitization, is safe, and is easily soluble in ordinary perfume compositions, and its compounding amount (use amount) is generally based on the total amount of the perfume composition. Is approximately 0.5 to 10% by weight, preferably 1.0%
~ 5.0% by weight.
本発明の香料組成物としては、前述のデヒドロジオイ
ゲノールを必須成分とするが、他に水性アルコール，テ
ルペン系アルコール，アセテート類，ケトン類，天然精
油その他通常香料を調製する際に用いられるものを組合
せることができる。As the fragrance composition of the present invention, the above-mentioned dehydrodioigenol is an essential component, and in addition, aqueous alcohols, terpene-based alcohols, acetates, ketones, natural essential oils, and other ingredients commonly used for preparing fragrances are also used. Can be combined.
本発明によれば、通常の香料組成物の香り立ち及び残
香性を高めることが可能となる。すなわち所望の揮発性
及び保留性を工業的安易かつ再現性良く得られその作用
効果の特異性は著しい。ADVANTAGE OF THE INVENTION According to this invention, it becomes possible to raise the fragrance | flavor appearance and residual fragrance | flavor of a normal fragrance composition. That is, the desired volatility and retentivity are obtained industrially easily and with good reproducibility, and the specificity of the action and effect is remarkable.
以下、実施例について説明する。 Hereinafter, examples will be described.
実施例に示すwt％は、重量％を意味する。また感作
性，残香性，香り立ち（匂い）等の試験方法は下記の通
りである。The wt% shown in the examples means wt%. The test methods for sensitization, residual scent, and odor (odor) are as follows.
（１）感作性の試験方法 体重350〜400g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列に行なった。(1) Test method of sensitization A skin of 4 × 6 cm on the scapula of a Hartley guinea pig (female) weighing 350 to 400 g was shaved, and three intradermal injections were arranged in one row in the following order. Made on line.
フロイント コンプリート アジュバンド（Freunds'
complete adjuvant、以下FFCAと略記する）を左右２ケ
所に0.05mlずつ皮内注射。Freund's Complete Adjuvant (Freunds'
Complete adjuvant (hereinafter abbreviated as FFCA) was injected intradermally into each of the left and right portions at 0.05 ml each.
試験サンプル10％オリーブ油溶液を左右２ケ所に0.05
mlずつ皮内注射。Test sample 10% olive oil solution 0.05
Intradermal injection in ml.
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。The same amount of sterilized water was added to the FCA solution containing 20% of the test sample, and 0.05 ml of the emulsified solution was intradermally injected into the right and left two places.
これらの操作１週間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。塗布24時間後に同部位に試験サンプル10％含
有オリーブ油溶液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、試験
サンプル５％,10％各オリーブ油溶液を24時間閉塞貼布
した。判定は、24時間後と48時間後に第１表に示した評
価基準に従って肉眼により行なった。One week 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 an olive oil solution containing a 10% test sample was applied to the gauze at the same site, and the occlusion was stuck for 48 hours. On the 21st day after the intradermal injection, the abdomen was shaved, and a test sample of 5% or 10% olive oil solution 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 1.
（２）残香性の試験方法 本発明の方法によって得られた本発明香料組成物の残
香性と比較例香料組成物の残香性を比較するために下記
の官能テストを採用した。 (2) Test method for residual fragrance The following sensory test was employed to compare the residual odor of the fragrance composition of the present invention obtained by the method of the present invention with the residual fragrance of the comparative fragrance composition.
試料香料組成物150mgを5.5×15cmの匂い紙に均一に塗
布し、官能検査室（温度25℃，湿度60％，風速0.1m/秒
以下）中に垂直状態で放置した。塗布後適当時間（例え
ば０分,30分,1時間,2時間,4時間）経過した時点で、そ
れぞれの匂い紙に付着した香料組成物の残香強度の比較
を10名の調香専門パネラーにより10回繰返して判定し
た。150 mg of the sample fragrance composition was uniformly applied to a 5.5 × 15 cm odor paper, and left in a sensory test room (temperature: 25 ° C., humidity: 60%, wind speed: 0.1 m / sec or less) in a vertical state. At an appropriate time after application (eg, 0 minutes, 30 minutes, 1 hour, 2 hours, 4 hours), a comparison of the residual scent intensity of the fragrance composition adhered to each odor paper was conducted by 10 expert panelists. Judgment was repeated 10 times.
（３）香り立ち（匂い）の試験方法 本発明の方法によって得られた本発明香料組成物の香
り立ちと比較例の香料組成物の香り立ちを比較するため
に下記の官能テストを採用した。(3) Test method of fragrance (odor) The following sensory test was employed to compare the fragrance of the fragrance composition of the present invention obtained by the method of the present invention with the fragrance of the fragrance composition of the comparative example.
試料香料組成物を80％アルコール溶液とし、匂い紙に
同量ずつ塗布し、それぞれの匂い紙に付着した試料香料
組成物の香り立ちの比較を10名の調香専門パネラーによ
り10回繰返して判定した。An 80% alcohol solution of the sample fragrance composition was applied to the odor paper in the same amount, and the comparison of the fragrance of the sample fragrance composition attached to each odor paper was repeated 10 times by ten perfume expert panelists. did.
また、実施例中のデヒドロジオイゲノールは、下記の
方法によって得たものを用いた。Moreover, what was obtained by the following method was used for the dehydrodioigenol in an Example.
オイゲノール20gとピリジン20gの混合物に、放置によ
り水加した硫酸鉄（II）少量を加え、30％H2O220gを滴
下しながら60〜70℃で８時間かきまぜ、以降８時間おき
に計５回30％H2O220gを加え、合計100gの30％H2O2を加
え、計40時間反応させた。反応後、エーテルで抽出し、
５％硫酸で洗ってからエーテルを留去し、水蒸気蒸留し
オイゲノールを回収することによって、フラスコ中に粗
デヒドロジオイゲノール11.2gを得た。これをエタノー
ルから再結晶してデヒドロジオイゲノールを得た。To a mixture of 20 g of eugenol and 20 g of pyridine, a small amount of iron (II) sulfate hydrated by standing is added, and 20 g of 30% H 2 O 2 is added dropwise while stirring at 60 to 70 ° C. for 8 hours. times 30% H 2 O 2 20g was added, of 30% H 2 O 2 sum 100g added and reacted meter 40 hours. After the reaction, the mixture was extracted with ether,
After washing with 5% sulfuric acid, ether was distilled off, and eugenol was recovered by steam distillation to obtain 11.2 g of crude dehydrodieugenol in the flask. This was recrystallized from ethanol to obtain dehydrodieugenol.
試験例１ 前述の方法により得たデヒドロジオイゲノールについ
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、第２表に示すように本発明で用いるデヒ
ドロジオイゲノールには感作性は確認されなかった。Test Example 1 The safety of dehydrodieugenol obtained by the above-described method was examined in accordance with the above-described test method of sensitization. As a result, as shown in Table 2, no sensitization was confirmed for dehydrodioigenol used in the present invention.
実施例1,比較例１〜３ 下記の処方に従って、実施例及び比較例の香料組成物
を調製した。なお、ベンジルサリシレート，ベンジルベ
ンゾエート，トリエチルシトレートは従来より保留剤と
して用いられているものである。 Example 1, Comparative Examples 1 to 3 Perfume compositions of Examples and Comparative Examples were prepared according to the following formulations. Note that benzyl salicylate, benzyl benzoate, and triethyl citrate have been conventionally used as retention agents.
（１）実施例１に関して前記感作性試験を行った結果、
感作性は確認されず、安全性の高い香料組成物であるこ
とが確認された。 (1) As a result of performing the sensitization test on Example 1,
No sensitization was confirmed, and it was confirmed that the composition was a highly safe fragrance composition.
（２）次に前記残香性試験を行い、実施例１と比較例１
〜３を比較した。その結果を第３表に示した。第３表か
ら明らかなごとく、本発明の香料組成物はすぐれた残香
性を有していた。(2) Next, the above-mentioned residual fragrance test was performed, and Example 1 and Comparative Example 1 were used.
Were compared. The results are shown in Table 3. As is evident from Table 3, the fragrance composition of the present invention had excellent residual odor.
（３）次に前記香り立ち（匂い）試験を行い、実施例１
と比較例１〜３を比較した。その結果を第４表に示し
た。 (3) Next, the above-mentioned scenting (smell) test was conducted.
And Comparative Examples 1 to 3 were compared. The results are shown in Table 4.
第４表から明らかな如く、本発明の香料組成物はすぐ
れた香り立ちを有していた。As is apparent from Table 4, the fragrance composition of the present invention had an excellent fragrance.
実施例２〜4,比較例２ 下記の処方に従って、実施例及び比較例の香料組成物
を調製した。 Examples 2 to 4, Comparative Example 2 Perfume compositions of Examples and Comparative Examples were prepared according to the following formulation.
前記残香性試験および香り立ち（匂い）の試験を行
い、比較例と比較した結果を第５表に示した。Table 5 shows the results of the above-mentioned residual odor test and odor test (odor).
第５表から明らかな如く、本発明の香料組成物はいず
れも比較例の香料組成物に比べ高い残香性，優れた香気
性を示した。As is clear from Table 5, all of the fragrance compositions of the present invention exhibited higher residual odor and excellent fragrance as compared with the fragrance compositions of Comparative Examples.
〔発明の効果〕 本発明で用いるデヒドロジオイゲノールを保留剤とし
て一般の香料組成物に用いることにより、香料の安全性
に障害を与える事なく香気持性を調整でき保留性を高め
ることが出来る。即ち、デヒドロジオイゲノールを配合
することにより香料組成物のマイルドかつ爽やかなトッ
プノートを強調し、また所望の香気の持続性を高めるこ
とが可能となる。したがって、その香料組成物の商品的
価値を著しく高めることが可能となり、その作用効果の
特異性は著しい。 [Effects of the Invention] By using the dehydrodioigenol used in the present invention as a retaining agent in a general fragrance composition, the fragrance retention can be adjusted without impairing the safety of the fragrance, and the retention can be enhanced. In other words, the addition of dehydrodioigenol enhances the mild and refreshing top note of the fragrance composition, and makes it possible to enhance the desired fragrance persistence. Therefore, the commercial value of the fragrance composition can be significantly increased, and the specificity of the effect is remarkable.
Claims (1)
徴とする香料組成物。(1) A fragrance composition comprising dehydrodieugenol represented by the formula:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20758189A JP2731255B2 (en) | 1989-08-09 | 1989-08-09 | Fragrance composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP20758189A JP2731255B2 (en) | 1989-08-09 | 1989-08-09 | Fragrance composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0368510A JPH0368510A (en) | 1991-03-25 |
| JP2731255B2 true JP2731255B2 (en) | 1998-03-25 |
Family
ID=16542127
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP20758189A Expired - Fee Related JP2731255B2 (en) | 1989-08-09 | 1989-08-09 | Fragrance composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2731255B2 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100535456B1 (en) * | 2003-04-04 | 2005-12-07 | 현대자동차주식회사 | Oil drain apparatus of oil pan |
-
1989
- 1989-08-09 JP JP20758189A patent/JP2731255B2/en not_active Expired - Fee Related
Non-Patent Citations (1)
| Title |
|---|
| Ａｇｒ．Ｂｉｏｌ．Ｃｈｅｍ．，Ｖｏｌ．３７，Ｎｏ．４（１９７３）ｐ．８８９−８９５ |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0368510A (en) | 1991-03-25 |
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