JP3045562B2 - Fragrance composition - Google Patents
Fragrance compositionInfo
- Publication number
- JP3045562B2 JP3045562B2 JP3138215A JP13821591A JP3045562B2 JP 3045562 B2 JP3045562 B2 JP 3045562B2 JP 3138215 A JP3138215 A JP 3138215A JP 13821591 A JP13821591 A JP 13821591A JP 3045562 B2 JP3045562 B2 JP 3045562B2
- Authority
- JP
- Japan
- Prior art keywords
- fragrance
- present
- fragrance composition
- residual
- diol
- 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 - Lifetime
Links
- 239000003205 fragrance Substances 0.000 title description 43
- 239000000203 mixture Substances 0.000 title description 29
- 229930006948 p-menthane-3,8-diol Natural products 0.000 claims description 8
- LMXFTMYMHGYJEI-UHFFFAOYSA-N p-menthane-3,8-diol Chemical compound CC1CCC(C(C)(C)O)C(O)C1 LMXFTMYMHGYJEI-UHFFFAOYSA-N 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 230000014759 maintenance of location Effects 0.000 description 8
- 239000002304 perfume Substances 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
- 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
- 239000000126 substance Substances 0.000 description 4
- 229960002903 benzyl benzoate Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000001953 sensory effect Effects 0.000 description 3
- 235000007586 terpenes Nutrition 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
- 235000000983 citronellal Nutrition 0.000 description 2
- 229930003633 citronellal Natural products 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000001069 triethyl citrate Substances 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
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000002009 diols Chemical class 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
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 150000002576 ketones Chemical class 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
- 125000000374 p-menthane-3,8-diol group Chemical group 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- -1 terpene alcohols Chemical class 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Landscapes
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
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ものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a fragrance composition excellent in fragrance and lingering scent.
【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。2. Description of the Related Art Conventionally, when an excellent fragrance is flavored using a natural or synthetic scented substance, a scented substance is required to maintain a desired scent. Various retention agents for adjusting the volatility and residual scent are blended in the fragrance as an active ingredient. For example, benzyl salicylate, benzyl benzoate, triethyl citrate, isopropyl myristate, diethyl phthalate and the like are used. However, these retention agents alone are not always sufficient to adjust the volatility and residual fragrance of the fragrance composition, and development of a new retention agent has been desired.
【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。[0003] The inventors of the present invention have conducted intensive studies to solve the above-mentioned disadvantages of the prior art, and as a result, have found that ordinary perfume compositions have p-
It has been found that by containing menthane-3,8-diol, the present invention has an excellent effect in adjusting the fragrance and residual odor of the fragrance, and completed the present invention.
【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保留剤を提供す
ることにある。[0004] That is, an object of the present invention is to provide a retention agent having an excellent effect in adjusting the fragrance and residual odor.
【０００５】[0005]
【課題を解決するための手段】上記の目的を達成する本
発明の保留剤は、ｐ−メンタン−３，８−ジオールから
なるものである。The retention agent of the present invention which achieves the above object is a p-menthane-3,8-diol.
It becomes .
【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、
１９８４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）。It has already been reported that the p-menthane-3,8-diol used in the present invention is an almost odorless compound contained in a small amount in matured lemon eucalyptus (Phytochemistry, Vol. 23, No. 12). , 2777,
1984). However, p-menthan-3,8-
It has not been reported that diols have the effect of enhancing the fragrance and residual scent of a fragrance composition. Further, since only a small amount of p-menthane-3,8-diol is contained in lemon eucalyptus oil, it may be used to improve the fragrance and residual fragrance of the fragrance composition which is the object of the present invention. No (Perfumer and Flavorist, Vol. 11, August / September, p. 74, 1986)
Year).
【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．Ａｍ．Ｃ
ｈｅｍ．Ｓｏｃ），７５巻，２３６７頁、１９５３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３〜９
０重量％、好ましくは５〜３０重量％である。[0007] The p-menthane-3,8-diol used in the present invention can be easily synthesized [Journal of American Chemical Society (J. Am. C.).
hem. Soc), 75, 2367, 1953]. In addition, the substance is easily soluble in ordinary fragrance compositions,
They can be arbitrarily compounded. Amount (use amount)
Is generally 3 to 9 based on the total amount of the fragrance composition.
0% by weight, preferably 5 to 30% by weight.
【０００８】本発明に係る香料組成物としては、ｐ−メ
ンタン−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。[0008] The fragrance composition according to the present invention contains p-menthane-3,8-diol as an essential component. In addition, water-soluble alcohols, terpene alcohols, acetates, ketones, terpenes, natural essential oils , Fragrance and other perfume modifiers such as ordinary benzyl benzoate and triethyl citrate.
【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。The p-menthane-3,8-diol used in the present invention has a cyclic terpene diol structure,
It has a structure completely different from that of the compound used as a retaining agent. Therefore, p-menthane-3,
The fragrance composition containing 8-diol can provide a mild and refreshing top note and residual fragrance different from the conventionally used retention agents.
【００１０】[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。The present invention will be described below with reference to examples. The% shown in the examples means% by weight. The test method of the fragrance characteristics such as fragrance and residual scent is as follows.
【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。(1) Test method of fragrance The following sensory test was employed to compare the fragrance of the fragrance composition according to the present invention with the fragrance of a fragrance composition as a comparative example. The sample fragrance composition was made into an 80% alcohol solution, applied in the same amount to odor paper, and the comparison of the fragrance of the sample fragrance composition adhering to each odor paper was repeated five times by five panelists specialized in fragrance to judge. did.
【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。(2) Test method for residual fragrance The following sensory test was employed to compare the residual fragrance of the fragrance composition according to the present invention with the residual fragrance of the fragrance composition as a comparative example. 5.5 cm × 1 of 150 mg of sample flavor composition
Apply evenly to 5cm scented paper and make a sensory test room (temperature 25
(° C., humidity 60%, wind speed 0.1 m / sec or less). At an appropriate time (2 hours, 4 hours) after the application, the comparison of the residual scent strength of the fragrance composition adhered to each odor paper was repeated five times by five perfume expert panelists and judged.
【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した。残渣部をシリカゲル
カラムクロマトにて精製することにより、６７ｇ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。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, the mixture was stirred for 20 hours. After the completion of the 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 a 5% aqueous sodium carbonate solution and three times with 300 ml of a saturated saline solution, and then dried over anhydrous sodium sulfate. After filtering off the anhydrous sodium sulfate,
Diethyl ether was removed under reduced pressure . Silica gel residue
Purification by column chromatography gave 67 g of p-
Mentane-3,8-diol (mixture of cis and trans isomers) was obtained.
【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。Example 1, Comparative Examples 1 to 3 Perfume compositions of Examples and Comparative Examples were prepared according to the formulation shown in Table 1 below. In addition, benzyl salicylate, benzyl benzoate, and diethyl phthalate have been conventionally used as retention agents. The p-menthane-3,8-diol used in the examples used was the one synthesized according to the above production example.
【００１５】[0015]
【表１】 [Table 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、本発明に係る香料組成物は優れ
た香り立ちを有していた。Next, a scent test was conducted to compare Example 1 with Comparative Examples 1 to 3. The results are shown in Table 2. As is clear from Table 2, the fragrance composition according to the present invention had an excellent fragrance.
【００１７】[0017]
【表２】 （延べ人数２５
人）[Table 2] (Total number of people 25
Man)
【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、本発明に係る香料組成物は優れた残
香性を有していた。Next, a residual scent test was conducted to compare Example 1 with Comparative Examples 1 to 3. Table 3 shows the results. As is evident from Table 3, the fragrance composition according to the present invention had excellent residual scent properties.
【００１９】[0019]
【表３】 （延べ人数２
５人）[Table 3] (Total number of people 2
5 people)
【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
に係る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。Examples 2 to 4, Comparative Example 4 Perfume compositions of Examples and Comparative Examples were prepared in accordance with the formulation shown in Table 4 below. Table 5 shows the results of the scent standing test and the residual scent test. As is clear from Table 5, the present invention
The perfume composition according to the both exhibited excellent aroma and substantivity compared with the perfume composition of Comparative Example.
【００２１】[0021]
【表４】 [Table 4]
【００２２】[0022]
【表５】
（延べ人数２５人）[Table 5]
(25 people in total)
【００２３】[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及び保留剤
を提供するものである。As described above, the present invention provides a useful fragrance composition and a retention agent which are extremely excellent in fragrance and residual odor.
───────────────────────────────────────────────────── フロントページの続き (58)調査した分野(Int.Cl.7，ＤＢ名) C11B 9/00 A61K 7/46 A61K 7/46 355 ＣＡ（ＳＴＮ) ＪＩＣＳＴファイル（ＪＯＩＳ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)────────────────────────────────────────────────── ─── Continued on the front page (58) Fields investigated (Int. Cl. 7 , DB name) C11B 9/00 A61K 7/46 A61K 7/46 355 CA (STN) JICST file (JOIS) REGISTRY (STN)
Claims (1)
る保留剤。1. A retaining agent comprising p-menthane-3,8-diol.
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 JPH04337395A (en) | 1992-11-25 |
| JP3045562B2 true 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 (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005112632A1 (en) * | 2004-05-20 | 2005-12-01 | Nelson Mandela Metropolitan University | Insect repellent compositions |
| US7538081B2 (en) | 2000-09-12 | 2009-05-26 | Takasago International Corporation | Method and agent for enhancing diffusivity and long-lasting property of fragrance |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8273367B2 (en) | 2001-04-17 | 2012-09-25 | The Procter And Gamble Company | Articles comprising a mint odor-free cooling agent |
| DE60120113T3 (en) * | 2001-04-17 | 2016-04-14 | The Procter & Gamble Company | Refreshing compositions |
| JP4177002B2 (en) | 2002-02-22 | 2008-11-05 | 高砂香料工業株式会社 | Fragrance composition |
| JP6929849B2 (en) | 2016-08-01 | 2021-09-01 | 高砂香料工業株式会社 | How to release unsaturated aldehydes or ketones |
| WO2018135647A1 (en) | 2017-01-19 | 2018-07-26 | 高砂香料工業株式会社 | Method for releasing aldehyde or ketone |
| CN111108090A (en) | 2017-09-25 | 2020-05-05 | 高砂香料工业株式会社 | Fragrance precursor |
| FR3098373B1 (en) * | 2019-07-10 | 2022-12-16 | Centre Nat Rech Scient | Mosquito repellent composition and method of preparation |
-
1991
- 1991-05-13 JP JP3138215A patent/JP3045562B2/en not_active Expired - Lifetime
Non-Patent Citations (1)
| Title |
|---|
| 化学と生物 Ｖｏｌ．２７，ＮＯ．８ １９８９年８月２５日 株式会社 学会出版センター発行 ４８６頁−４８８頁 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7538081B2 (en) | 2000-09-12 | 2009-05-26 | Takasago International Corporation | Method and agent for enhancing diffusivity and long-lasting property of fragrance |
| WO2005112632A1 (en) * | 2004-05-20 | 2005-12-01 | Nelson Mandela Metropolitan University | Insect repellent compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH04337395A (en) | 1992-11-25 |
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