JPH05171179A - Perfume composition - Google Patents
Perfume compositionInfo
- Publication number
- JPH05171179A JPH05171179A JP35523091A JP35523091A JPH05171179A JP H05171179 A JPH05171179 A JP H05171179A JP 35523091 A JP35523091 A JP 35523091A JP 35523091 A JP35523091 A JP 35523091A JP H05171179 A JPH05171179 A JP H05171179A
- Authority
- JP
- Japan
- Prior art keywords
- diol
- menthane
- methylene
- methyl
- fragrance
- 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.)
- Granted
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、香り立ち及び残香性に
優れた香料組成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a fragrance composition having excellent scenting and residual aroma.
【０００２】[0002]
【従来の技術及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
質の揮発性及び残香性を調整する各種保留剤が香料に有
効成分として配合されている。例えば、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、これらの保留剤だけ
では、香料組成物の揮発性や残香性を調整するのに必ず
しも十分に満足できるものではなく、新規な保留剤の開
発が望まれていた。2. Description of the Related Art Conventionally, when a natural or synthetic fragrance substance is used to perfume an excellent fragrance, in order to maintain a desired fragrance, the volatility of the fragrance substance and Various retention agents for adjusting the residual aroma are blended in the fragrance as active ingredients. For example, benzyl salicylate, benzyl benzoate, triethyl citrate, isopropyl myristate, diethyl phthalate and the like are used. However, these holding agents alone are not always sufficiently satisfactory to adjust the volatility and residual aroma of the fragrance composition, and the development of new holding agents has been desired.
【０００３】そこで本発明の目的は、香り立ち及び残香
性に優れた香料組成物を提供することにある。Therefore, an object of the present invention is to provide a fragrance composition having excellent scenting and residual aroma.
【０００４】[0004]
【課題を解決するための手段】本発明者等は、前記従来
技術の難点を解消せんと鋭意研究を行った結果、通常の
香料組成物にｐ−メンタン−２−メチレン−３，８−ジ
オールもしくはｐ−メンタン−２−メチル−３，８−ジ
オールを３〜９０重量％、好ましくは５〜３０重量％を
配合することにより香料の香り立ち及び残香性を調整す
ることに優れた効果を有することを見いだし本発明を完
成した。Means for Solving the Problems As a result of intensive studies aimed at solving the above-mentioned problems of the prior art, the present inventors have found that p-menthane-2-methylene-3,8-diol can be added to ordinary perfume compositions. Alternatively, by blending p-menthane-2-methyl-3,8-diol in an amount of 3 to 90% by weight, preferably 5 to 30% by weight, it has an excellent effect in adjusting the scenting and residual aroma of a fragrance. The present invention has been completed and the present invention has been completed.
【０００５】即ち、本発明はｐ−メンタン−２−メチレ
ン−３，８−ジオールもしくはｐ−メンタン−２−メチ
ル−３，８−ジオールを有効成分として３〜９０重量％
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 comprises p-menthane-2-methylene-3,8-diol or p-menthane-2-methyl-3,8-diol as an active ingredient in an amount of 3 to 90% by weight.
It is a perfume composition characterized by containing.
【０００６】以下、本発明の構成の詳細について説明す
る。本発明のｐ−メンタン−２−メチレン−３，８−ジ
オールは、３，７−ジメチル−２−メチレン−６−オク
テナールを硫酸等の酸水溶液と混合撹拌することにより
得ることができる。また、本発明のｐ−メンタン−２−
メチル−３，８−ジオールは、２，３，７−トリメチル
−６−オクテナールを硫酸等の酸水溶液と混合撹拌する
ことにより得ることができる。本発明のｐ−メンタン−
２−メチレン−３，８−ジオールもしくはｐ−メンタン
−２−メチル−３，８−ジオールを得るための原料物質
である３，７−ジメチル−２−メチレン−６−オクテナ
ールもしくは２，３，７−トリメチル−６−オクテナー
ルは、シトロネラールより安易に得られる化合物である
ことが知られている（ＵＳＰ３，４６３，８１８号公
報）。The details of the configuration of the present invention will be described below. The p-menthane-2-methylene-3,8-diol of the present invention can be obtained by mixing and stirring 3,7-dimethyl-2-methylene-6-octenal with an aqueous acid solution such as sulfuric acid. In addition, p-menthane-2-of the present invention
Methyl-3,8-diol can be obtained by mixing 2,3,7-trimethyl-6-octenal with an aqueous acid solution such as sulfuric acid and stirring. P-menthane of the present invention
3,7-Dimethyl-2-methylene-6-octenal or 2,3,7 which is a starting material for obtaining 2-methylene-3,8-diol or p-menthane-2-methyl-3,8-diol -Trimethyl-6-octenal is known to be a compound that can be easily obtained from citronellal (USP 3,463,818).
【０００７】この合成方法により、ｐ−メンタン−２−
メチレン−３，８−ジオールもしくはｐ−メンタン−２
−メチル−３，８−ジオールは無色透明の油状物で得ら
れる。 そして、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、３〜９０重量％、好ま
しくは５〜３０重量％である。By this synthetic method, p-menthane-2-
Methylene-3,8-diol or p-menthane-2
-Methyl-3,8-diol is obtained as a colorless transparent oily substance. Then, the blending amount (usage amount) thereof is generally 3 to 90% by weight, preferably 5 to 30% by weight, based on the total amount of the fragrance composition.
【０００８】本発明の香料組成物としては、ｐ−メンタ
ン−２−メチレン−３，８−ジオールもしくはｐ−メン
タン−２−メチル−３，８−ジオールを必須成分とする
が、他に水溶性アルコール、テルペン系アルコール、ア
セテート類、ケトン類、テルペン類、天然精油、調合香
料、その他例えば通常のベンジルベンゾエートやトリエ
チルシトレート等の香料調整剤と組み合わせて用いるこ
とができる。The fragrance composition of the present invention contains p-menthane-2-methylene-3,8-diol or p-menthane-2-methyl-3,8-diol as an essential component, but is also water-soluble. It can be used in combination with alcohols, terpene-based alcohols, acetates, ketones, terpenes, natural essential oils, prepared fragrances, and other fragrance modifiers such as ordinary benzyl benzoate and triethyl citrate.
【０００９】本発明で用いるｐ−メンタン−２−メチレ
ン−３，８−ジオールもしくはｐ−メンタン−２−メチ
ル−３，８−ジオールは環状テルペンジオールの構造を
有しており、これまで保留剤として用いられている化合
物とは全く異なる構造を有している。このためｐ−メン
タン−２−メチレン−３，８−ジオールもしくはｐ−メ
ンタン−２−メチル−３，８−ジオール配合した香料組
成物は、従来より用いられている保留剤とは異なったマ
イルドかつ爽やかなトップノートや残香を提供すること
が可能となる。The p-menthane-2-methylene-3,8-diol or p-menthane-2-methyl-3,8-diol used in the present invention has the structure of a cyclic terpene diol, and has been a retention agent until now. It has a completely different structure from the compound used as. Therefore, a fragrance composition containing p-menthane-2-methylene-3,8-diol or p-menthane-2-methyl-3,8-diol has a mildness different from that of a conventionally used retention agent. It is possible to provide a refreshing top note and scent.
【００１０】[0010]
【実施例】以下、実施例によって、本発明を更に詳細に
説明する。尚、実施例に示す％は、重量％を意味する。
また実施例に先立って、香り立ち及び残香性等の芳香特
性の試験方法について記載する。 （１）香り立ちの試験方法 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５名の調香専門パネラーによ
り５回繰り返して判定した。The present invention will be described in more detail with reference to the following examples. In the examples,% means% by weight.
In addition, prior to the examples, a method for testing aroma characteristics such as aroma and residual aroma will be described. (1) Test method for scenting The sample fragrance composition was made into an 80% alcohol solution, applied in the same amount on each scented paper, and a comparison of the scenting of the sample scented compositions attached to each scented paper was performed by five scents. It was judged 5 times by a professional panelist.
【００１１】（２）残香性の試験方法 試料香料組成物１５０ｍｇを５．５ｃｍ×１５ｃｍの匂
い紙に均一に塗布し、官能検査室（温度２５℃・湿度６
０％・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（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５名の調香専門パネラーにより５回繰り返して
判定した。(2) Test method for residual odor property 150 mg of the sample fragrance composition was uniformly applied to 5.5 cm × 15 cm odor paper, and the sensory test room (temperature 25 ° C., humidity 6
It was left in a vertical state in 0% wind speed of 0.1 m / sec or less). After a suitable time (2 hours, 4 hours) had elapsed after the application, the comparison of the residual scent intensity of the fragrance compositions attached to the respective odor papers was repeated 5 times by 5 expert scented panelists.
【００１２】ｐ−メンタン−２−メチレン−３，８−ジ
オールの製造例 ３，７−ジメチル−２−メチレン−６−オクテナール１
００ｇを５％硫酸水溶液５００ｍｌ中に徐々に撹拌混合
した。全量の３，７−ジメチル−２−メチレン−６−オ
クテナールを混合した後、２０時間撹拌を行った。撹拌
混合終了後、有機層をジエチルエーテル２００ｍｌで抽
出した。ジエチルエーテル層を５％炭酸ナトリウム水溶
液３００ｍｌにて３回、飽和食塩水溶液３００ｍｌで３
回洗浄した後、無水硫酸ナトリウムで乾燥した。無水硫
酸ナトリウムを濾別した後、ジエチルエーテルを減圧除
去することにより、８５ｇの淡黄色油状物を得た。マス
スペクトル測定において〔親ピーク〕−１８（Ｍ−Ｈ2
Ｏ）を認めたことから、ｐ−メンタン−２−メチレン−
３，８−ジオールの生成を確認した。Production Example of p-Mentane-2-methylene-3,8-diol 3,7-Dimethyl-2-methylene-6-octenal 1
00 g was gradually mixed with stirring in 500 ml of a 5% sulfuric acid aqueous solution. After the whole amount of 3,7-dimethyl-2-methylene-6-octenal was mixed, stirring was carried out for 20 hours. After completion of stirring and mixing, the organic layer was extracted with 200 ml of diethyl ether. The diethyl ether layer was washed 3 times with 300 ml of 5% aqueous sodium carbonate solution and 3 times with 300 ml of saturated saline solution.
After washing twice, it was dried over anhydrous sodium sulfate. After filtering off anhydrous sodium sulfate, 85 g of a pale yellow oily substance was obtained by removing diethyl ether under reduced pressure. [Parent peak] -18 (M-H 2
Since O) was recognized, p-menthane-2-methylene-
Formation of 3,8-diol was confirmed.
【００１３】ｐ−メンタン−２−メチル−３，８−ジオ
ールの製造例 ２，３，７−トリメチル−６−オクテナール５０ｇを５
％硫酸水溶液２００ｍｌ中に徐々に撹拌混合した。全量
の２，３，７−トリメチル−６−オクテナールを混合し
た後、１０時間撹拌を行った。撹拌混合終了後，有機層
をジエチルエーテル１００ｍｌで抽出した。ジエチルエ
ーテル層を５％炭酸ナトリウム水溶液１００ｍｌにて３
回、飽和食塩水溶液１００ｍｌで３回洗浄した後、無水
硫酸ナトリウムで乾燥した。無水硫酸ナトリウムを濾別
した後、ジエチルエーテルを減圧除去することにより、
４３ｇの淡黄色油状物を得た。マススペクトル測定にお
いて〔親ピーク〕−１８（Ｍ−Ｈ2 Ｏ）を認めたことか
ら、ｐ−メンタン−２−メチル−３，８−ジオールの生
成を確認した。Preparation Example of p-Mentane-2-methyl-3,8-diol 2,3,7-trimethyl-6-octenal
The mixture was gradually mixed with stirring in 200 ml of a sulfuric acid aqueous solution of 100%. After the total amount of 2,3,7-trimethyl-6-octenal was mixed, the mixture was stirred for 10 hours. After completion of stirring and mixing, the organic layer was extracted with 100 ml of diethyl ether. The diethyl ether layer was mixed with 100 ml of a 5% aqueous sodium carbonate solution to 3 times.
After washing three times with 100 ml of a saturated saline solution, it was dried over anhydrous sodium sulfate. After filtering off anhydrous sodium sulfate, by removing diethyl ether under reduced pressure,
43 g of a pale yellow oil was obtained. In mass spectroscopy since it showed a [parent peak] -18 (M-H 2 O) , to confirm the formation of p- menthane-2-methyl-3,8-diol.
【００１４】実施例１，２及び比較例１，２（香料組成
物） 下記表１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。尚、ベンジルサリシレート、ジエチルフ
タ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。また、実施例に用いたｐ−メンタン−２−メチレ
ン−３，８−ジオール及びｐ−メンタン−２−メチル−
３，８−ジオールは、前記製造例により合成したものを
用いた。Examples 1 and 2 and Comparative Examples 1 and 2 (Perfume Compositions) Perfume compositions of Examples and Comparative Examples were prepared according to the formulations shown in Table 1 below. In addition, benzyl salicylate and diethyl phthalate have been conventionally used as a retaining agent. Also, p-menthane-2-methylene-3,8-diol and p-menthane-2-methyl-used in the examples.
As the 3,8-diol, the one synthesized according to the above Production Example was used.
【００１５】[0015]
【表１】 [Table 1]
【００１６】（１）次に香り立ちの試験を行い、実施例
１もしくは実施例２と比較例１，２を比較した。その結
果を表２、３に示した。 表２、３から明らかなごと
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。(1) Next, a fragrance test was conducted to compare Example 1 or Example 2 with Comparative Examples 1 and 2. The results are shown in Tables 2 and 3. As is clear from Tables 2 and 3, the fragrance composition of the present invention had an excellent fragrance.
【００１７】[0017]
【表２】 [Table 2]
【００１８】[0018]
【表３】 [Table 3]
【００１９】（２）次に残香性試験を行い、実施例１も
しくは実施例２と比較例１，２を比較した。その結果を
表４に示した。表４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, a residual odor test was conducted to compare Example 1 or Example 2 with Comparative Examples 1 and 2. The results are shown in Table 4. As is clear from Table 4, the fragrance composition of the present invention had an excellent residual aroma.
【００２０】[0020]
【表４】 [Table 4]
【００２１】[0021]
【発明の効果】以上記載の如く、通常の香料組成物に、
ｐ−メンタン−２−メチレン−３，８−ジオールもしく
はｐ−メンタン−２−メチル−３，８−ジオールを３〜
９０重量％、好ましくは５〜３０重量％を配合すること
により、香り立ち及び残香性に優れた香料組成物が得ら
れることは明らかである。As described above, in the usual fragrance composition,
p-menthane-2-methylene-3,8-diol or p-menthane-2-methyl-3,8-diol is added to 3 to
It is clear that by blending 90% by weight, preferably 5 to 30% by weight, a fragrance composition excellent in scenting and residual aroma can be obtained.
Claims (2)
ジオールを有効成分として３〜９０重量％配合すること
を特徴とする香料組成物。1. p-Mentane-2-methylene-3,8-
A fragrance composition comprising 3 to 90% by weight of a diol as an active ingredient.
オールを有効成分として３〜９０重量％配合することを
特徴とする香料組成物。2. A fragrance composition comprising p-menthane-2-methyl-3,8-diol as an active ingredient in an amount of 3 to 90% by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35523091A JP2927590B2 (en) | 1991-12-19 | 1991-12-19 | Fragrance composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP35523091A JP2927590B2 (en) | 1991-12-19 | 1991-12-19 | Fragrance composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH05171179A true JPH05171179A (en) | 1993-07-09 |
| JP2927590B2 JP2927590B2 (en) | 1999-07-28 |
Family
ID=18442716
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP35523091A Expired - Lifetime JP2927590B2 (en) | 1991-12-19 | 1991-12-19 | Fragrance composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2927590B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6130255A (en) * | 1993-10-22 | 2000-10-10 | Ikemoto; Takeshi | Noxious-insect repellent |
| CN114384161A (en) * | 2020-10-22 | 2022-04-22 | 小川香料株式会社 | Method for evaluating residual fragrance property of perfume, residual fragrance imparting agent, and residual fragrance property improving method |
-
1991
- 1991-12-19 JP JP35523091A patent/JP2927590B2/en not_active Expired - Lifetime
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6130255A (en) * | 1993-10-22 | 2000-10-10 | Ikemoto; Takeshi | Noxious-insect repellent |
| CN114384161A (en) * | 2020-10-22 | 2022-04-22 | 小川香料株式会社 | Method for evaluating residual fragrance property of perfume, residual fragrance imparting agent, and residual fragrance property improving method |
| CN114384161B (en) * | 2020-10-22 | 2024-01-02 | 小川香料株式会社 | Method for evaluating residual fragrance of perfume, residual fragrance imparting agent, and method for improving residual fragrance |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2927590B2 (en) | 1999-07-28 |
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