JPH04337395A - Perfume composition - Google Patents
Perfume compositionInfo
- Publication number
- JPH04337395A JPH04337395A JP13821591A JP13821591A JPH04337395A JP H04337395 A JPH04337395 A JP H04337395A JP 13821591 A JP13821591 A JP 13821591A JP 13821591 A JP13821591 A JP 13821591A JP H04337395 A JPH04337395 A JP H04337395A
- Authority
- JP
- Japan
- Prior art keywords
- fragrance
- diol
- menthane
- present
- perfume
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- 239000002304 perfume Substances 0.000 title abstract description 13
- LMXFTMYMHGYJEI-UHFFFAOYSA-N p-menthane-3,8-diol Chemical compound CC1CCC(C(C)(C)O)C(O)C1 LMXFTMYMHGYJEI-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229930006948 p-menthane-3,8-diol Natural products 0.000 claims abstract description 11
- 239000004480 active ingredient Substances 0.000 claims abstract description 5
- 239000003205 fragrance Substances 0.000 claims description 50
- 238000002156 mixing Methods 0.000 abstract description 5
- 235000007586 terpenes Nutrition 0.000 abstract description 4
- 150000001298 alcohols Chemical class 0.000 abstract description 3
- 150000001875 compounds Chemical class 0.000 abstract description 3
- 150000001242 acetic acid derivatives Chemical class 0.000 abstract description 2
- 150000002576 ketones Chemical class 0.000 abstract description 2
- 150000003505 terpenes Chemical class 0.000 abstract description 2
- 239000000341 volatile oil Substances 0.000 abstract description 2
- 239000004615 ingredient Substances 0.000 abstract 3
- 125000004122 cyclic group Chemical class 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 230000014759 maintenance of location Effects 0.000 description 8
- 238000012360 testing method Methods 0.000 description 7
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 6
- 239000000126 substance Substances 0.000 description 5
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 4
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 description 4
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 230000002688 persistence Effects 0.000 description 4
- 229960002903 benzyl benzoate Drugs 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003755 preservative agent Substances 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- 238000010998 test method Methods 0.000 description 3
- 235000005979 Citrus limon Nutrition 0.000 description 2
- 244000131522 Citrus pyriformis Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DOOTYTYQINUNNV-UHFFFAOYSA-N Triethyl citrate Chemical compound CCOC(=O)CC(O)(C(=O)OCC)CC(=O)OCC DOOTYTYQINUNNV-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 235000000983 citronellal Nutrition 0.000 description 2
- 229930003633 citronellal Natural products 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 2
- 235000013769 triethyl citrate Nutrition 0.000 description 2
- 239000001069 triethyl citrate Substances 0.000 description 2
- HIQIXEFWDLTDED-UHFFFAOYSA-N 4-hydroxy-1-piperidin-4-ylpyrrolidin-2-one Chemical compound O=C1CC(O)CN1C1CCNCC1 HIQIXEFWDLTDED-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 244000166124 Eucalyptus globulus Species 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000010642 eucalyptus oil Substances 0.000 description 1
- 229940044949 eucalyptus oil Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- -1 terpene alcohols Chemical class 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
Abstract
Description
【発明の詳細な説明】
【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ものである。
【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
調香する際には、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有効成分
として香料に配合されている。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
も十分でなく、新規な保留剤の開発が望まれていた。
【０００３】本発明者等は、前記従来技術の難点を解消
せんと鋭意検討を行った結果、通常の香料組成物にｐ−
メンタン−３，８−ジオールを含有することにより、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
有することを見い出し本発明を完成した。
【０００４】即ち、本発明の目的は、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香料組成物を提
供することにある。
【０００５】
【課題を解決するための手段】上記の目的を達成する本
発明の香料組成物は、ｐ−メンタン−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
するものである。
【０００６】本発明で用いるｐ−メンタンー３，８−ジ
オールは、成木したレモンユーカリ中に少量含まれるほ
とんど無臭の化合物であることは既に報告されている（
フィトケミストリィ，２３巻，１２号，２７７７頁、１
９８４年）。しかしながら、ｐ−メンタンー３，８−ジ
オールが香料組成物の香り立ち及び残香性を高める効果
を有することはなんら報告されていない。また、レモン
ユーカリ油中にはｐ−メンタン−３，８−ジオールが少
量しか含有されていないため、本発明の目的である香料
組成物の香り立ちや残香性を改善するためには用いるこ
とができなかった（パーフューマー アンド フレ
イバリスト１１巻、８月／９月号、７４頁、１９８６年
）。
【０００７】本発明で用いるｐ−メンタン−３，８−ジ
オールは容易に合成することができる［ジャーナル
オブ アメリカンケミカル ソサイエティ（Ｊ．Ａ
ｍ．Ｃｈｅｍ．Ｓｏｃ），７５巻，２３６７頁、１９５
３年参照］。また、本物質は通常の香料組成物に易溶で
あり、任意に配合することができる。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。
【０００８】本発明の香料組成物としては、ｐ−メンタ
ンー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。
【０００９】本発明で用いるｐ−メンタンー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−３，
８−ジオールを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且つ爽やかなトッ
プノートや残香を提供することが可能となる。
【００１０】
【実施例】以下、実施例により、本発明を説明する。実
施例に示す％は、重量％を意味する。また、香り立ち及
び残香性等の芳香特性の試験方法は下記の通りである。
【００１１】（１）香り立ちの試験方法本発明による香
料組成物の香り立ちと、比較例としての香料組成物の香
り立ちとを比較するために下記の官能テストを採用した
。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。
【００１２】（２）残香性の試験方法
本発明による香料組成物の残香性と、比較例としての香
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。試料香料組成物１５０ｍｇを５．５ｃｍ×１
５ｃｍ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（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。
【００１３】製造例
シトロネラール１００ｇを５％硫酸水溶液５０ｍｌ中に
徐々に撹拌混合した。全量のシトロネラールを混合した
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、９
７ｇのｐ−メンタン−３，８−ジオール（シス、トラン
スの異性体混合）を得た。
【００１４】実施例１，比較例１〜３
下記表１の処方に従って、実施例及び比較例の香料組成
物を調整した。なお、ベンジルサリシレート、ベンジル
ベンゾエート、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−メンタンー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。
【００１５】
【表１】
【００１６】次に香り立ちの試験を行い、実施
例１と比較例１〜３とを比較した。その結果を表２に示
した。表２から明らかなごとく、本発明の香料組成物は
優れた香り立ちを有していた。
【００１７】
【表２】
（延べ人数２５人）
【００１８】次に残香性試験を行い、実施例１と比較例
１〜３とを比較した。その結果を表３に示した。表３か
ら明らかなごとく、本発明の香料組成物は優れた残香性
を有していた。
【００１９】
【表３】
（延べ人数２５人）
【００２０】実施例２〜４、比較例４
下記表４の処方に従って、実施例及び比較例の香料組成
物を調整した。香り立ちの試験及び残香性試験を行った
結果を表５に示した。表５から明らかなごとく、本発明
の香料組成物は何れも比較例の香料組成物に比べ優れた
香り立ちと残香性を示した。
【００２１】
【表４】
【００２２】
【表５】
（延べ
人数２５人）【００２３】
【発明の効果】以上述べた通り、本発明は、香り立ち及
び残香性に極めて優れた有用なる香料組成物を提供する
ものである。DETAILED DESCRIPTION OF THE INVENTION [0001] The present invention relates to a fragrance composition that is excellent in fragrance onset and fragrance retention. [Prior Art and Problems to be Solved by the Invention] Conventionally, when creating a superior fragrance using a natural or synthetic aromatic substance, it has been necessary to use a natural or synthetic aromatic substance to maintain the desired aroma. Various preservatives that adjust the volatility and residual odor of fragrance substances are incorporated into fragrances as active ingredients. For example, benzyl salicylate, benzyl benzoate, triethyl citrate, isopropyl myristate, diethyl phthalate, etc. are used. However, these preservatives alone are not necessarily sufficient to adjust the volatility and odor persistence of perfume compositions, and the development of new preservatives has been desired. [0003] The inventors of the present invention have made extensive studies to resolve the drawbacks of the prior art, and as a result, the present inventors have added p-
The present invention has been completed based on the discovery that the inclusion of menthane-3,8-diol has an excellent effect on controlling the fragrance and lingering properties of fragrances. [0004] That is, an object of the present invention is to provide a fragrance composition that has an excellent effect on controlling fragrance onset and fragrance persistence. [Means for Solving the Problems] The fragrance composition of the present invention which achieves the above object is characterized by containing 3 to 90% by weight of p-menthane-3,8-diol as an active ingredient. It is something to do. It has already been reported that p-menthane-3,8-diol used in the present invention is an almost odorless compound contained in small amounts in mature lemon eucalyptus trees (
Phytochemistry, Volume 23, No. 12, Page 2777, 1
984). However, there has been no report that p-menthane-3,8-diol has the effect of enhancing the fragrance and persistence of fragrance compositions. In addition, since lemon eucalyptus oil contains only a small amount of p-menthane-3,8-diol, it cannot be used to improve the fragrance and lingering properties of fragrance compositions, which is the objective of the present invention. I couldn't do it (Perfumer and Flavorist Vol. 11, August/September issue, p. 74, 1986). p-menthane-3,8-diol used in the present invention can be easily synthesized [Journal
of American Chemical Society (J.A.
m. Chem. Soc), vol. 75, p. 2367, 195
3rd year reference]. Moreover, this substance is easily soluble in ordinary fragrance compositions and can be blended as desired. The blending amount (amount used) is generally 3% based on the total amount of the fragrance composition.
-90% by weight, preferably 5-30% by weight. The fragrance composition of the present invention contains p-menthane-3,8-diol as an essential component, but also contains water-soluble alcohols, terpene alcohols, acetates, ketones, terpenes, natural essential oils, and blends. It can be used in combination with perfumes and other perfume modifiers such as the usual benzyl benzoate and triethyl citrate. p-menthane-3,8-diol used in the present invention has a cyclic terpene diol structure,
It has a completely different structure from the compounds used as retention agents to date. Therefore, p-menthane-3,
A perfume composition containing 8-diol can provide a mild and refreshing top note and lingering fragrance that are different from conventionally used retention agents. [Examples] The present invention will be explained below with reference to Examples. The % shown in the examples means % by weight. In addition, the test methods for aroma characteristics such as fragrance development and lingering fragrance are as follows. (1) Test method for fragrance release The following sensory test was adopted to compare the fragrance release of the fragrance composition according to the present invention and the fragrance release of a fragrance composition as a comparative example. A sample fragrance composition is made into an 80% alcohol solution, and the same amount is applied to a scented paper, and the fragrance of the sample fragrance composition attached to each scented paper is compared 5 times and judged by 5 perfume expert panelists. did. (2) Test method for fragrance lingering The following sensory test was employed to compare the fragrance lingering properties of the perfume composition according to the present invention and the fragrance composition as a comparative example. 150mg of sample fragrance composition in 5.5cm x 1
Apply it evenly on a 5 cm scented paper and place it in the sensory testing room (temperature 25
℃, humidity 60%, wind speed 0.1 m/sec or less). After an appropriate period of time (2 hours, 4 hours) had passed after application, the residual fragrance strength of the fragrance compositions adhered to each scented paper was compared 5 times and judged by 5 perfume expert panelists. Production Example 100 g of citronellal was gradually stirred and mixed into 50 ml of a 5% aqueous sulfuric acid solution. After mixing the entire amount of citronellal, stirring was performed for 20 hours. After stirring and mixing, the organic layer was extracted with 200 ml of diethyl ether. The diethyl ether layer was washed three times with 300 ml of 5% aqueous sodium carbonate solution and three times with 300 ml of saturated saline solution, and then dried over anhydrous sodium sulfate. After filtering off anhydrous sodium sulfate, diethyl ether was removed under reduced pressure to obtain 9.
7 g of p-menthane-3,8-diol (mixture of cis and trans isomers) was obtained. Example 1, Comparative Examples 1 to 3 Perfume compositions of Examples and Comparative Examples were prepared according to the formulations shown in Table 1 below. Note that benzyl salicylate, benzyl benzoate, and diethyl phthalate have been conventionally used as retention agents. Moreover, p-menthane-3,8-diol used in the examples was synthesized according to the above production example. [0015] [Table 1] [0016] Next, a fragrance test was conducted to compare Example 1 and Comparative Examples 1 to 3. The results are shown in Table 2. As is clear from Table 2, the fragrance composition of the present invention had excellent fragrance. [Table 2]
(Total number of people: 25) Next, a fragrance retention test was conducted to compare Example 1 and Comparative Examples 1 to 3. The results are shown in Table 3. As is clear from Table 3, the fragrance composition of the present invention had excellent fragrance retention. [Table 3]
(25 people in total) Examples 2 to 4, Comparative Example 4 Perfume compositions of Examples and Comparative Examples were prepared according to the formulations shown in Table 4 below. Table 5 shows the results of the scent emitting test and scent persistence test. As is clear from Table 5, all of the fragrance compositions of the present invention exhibited superior fragrance development and fragrance retention compared to the fragrance compositions of comparative examples. [Table 4] [Table 5]
(Total number of participants: 25) [Effects of the Invention] As described above, the present invention provides a useful fragrance composition that is extremely excellent in fragrance development and fragrance retention.
Claims (1)
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。1. A fragrance composition containing 3 to 90% by weight of p-menthane-3,8-diol as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3138215A JP3045562B2 (en) | 1991-05-13 | 1991-05-13 | Fragrance composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3138215A JP3045562B2 (en) | 1991-05-13 | 1991-05-13 | Fragrance composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH04337395A true JPH04337395A (en) | 1992-11-25 |
| JP3045562B2 JP3045562B2 (en) | 2000-05-29 |
Family
ID=15216778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3138215A Expired - Lifetime JP3045562B2 (en) | 1991-05-13 | 1991-05-13 | Fragrance composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3045562B2 (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1250914A1 (en) * | 2001-04-17 | 2002-10-23 | The Procter & Gamble Company | Cooling compositions |
| US7196052B2 (en) | 2002-02-22 | 2007-03-27 | Takasago International Corporation | Fragrance composition |
| US8273367B2 (en) | 2001-04-17 | 2012-09-25 | The Procter And Gamble Company | Articles comprising a mint odor-free cooling agent |
| WO2018025882A1 (en) | 2016-08-01 | 2018-02-08 | 高砂香料工業株式会社 | Method for releasing unsaturated aldehyde or ketone |
| WO2018135647A1 (en) | 2017-01-19 | 2018-07-26 | 高砂香料工業株式会社 | Method for releasing aldehyde or ketone |
| WO2019059375A1 (en) | 2017-09-25 | 2019-03-28 | 高砂香料工業株式会社 | Perfume precursor |
| WO2021005204A1 (en) * | 2019-07-10 | 2021-01-14 | Centre National De La Recherche Scientifique | Mosquito repellent composition and method for the preparation thereof |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5025845B2 (en) | 2000-09-12 | 2012-09-12 | 高砂香料工業株式会社 | Method and agent for enhancing perfume fragrance and sustainability |
| BRPI0510828A (en) * | 2004-05-20 | 2007-11-27 | Nelson Mandela Metropolitan Un | insect repellent composition |
-
1991
- 1991-05-13 JP JP3138215A patent/JP3045562B2/en not_active Expired - Lifetime
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1250914A1 (en) * | 2001-04-17 | 2002-10-23 | The Procter & Gamble Company | Cooling compositions |
| WO2002083095A1 (en) * | 2001-04-17 | 2002-10-24 | The Procter & Gamble Company | Cooling compositions |
| CN100441158C (en) * | 2001-04-17 | 2008-12-10 | 宝洁公司 | Cooling compositons |
| US8273367B2 (en) | 2001-04-17 | 2012-09-25 | The Procter And Gamble Company | Articles comprising a mint odor-free cooling agent |
| EP1250914B2 (en) † | 2001-04-17 | 2015-11-25 | The Procter & Gamble Company | Cooling compositions |
| US7196052B2 (en) | 2002-02-22 | 2007-03-27 | Takasago International Corporation | Fragrance composition |
| WO2018025882A1 (en) | 2016-08-01 | 2018-02-08 | 高砂香料工業株式会社 | Method for releasing unsaturated aldehyde or ketone |
| US10442821B2 (en) | 2016-08-01 | 2019-10-15 | Takasago International Corporation | Method for releasing unsaturated aldehyde or ketone |
| WO2018135647A1 (en) | 2017-01-19 | 2018-07-26 | 高砂香料工業株式会社 | Method for releasing aldehyde or ketone |
| WO2019059375A1 (en) | 2017-09-25 | 2019-03-28 | 高砂香料工業株式会社 | Perfume precursor |
| US11802258B2 (en) | 2017-09-25 | 2023-10-31 | Takasago International Corporation | Perfume precursor |
| WO2021005204A1 (en) * | 2019-07-10 | 2021-01-14 | Centre National De La Recherche Scientifique | Mosquito repellent composition and method for the preparation thereof |
| FR3098373A1 (en) * | 2019-07-10 | 2021-01-15 | Centre National De La Recherche Scientifique | Mosquito repellent composition and method of preparation |
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| Publication number | Publication date |
|---|---|
| JP3045562B2 (en) | 2000-05-29 |
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