JPS6136821B2 - - Google Patents
Info
- Publication number
- JPS6136821B2 JPS6136821B2 JP4048081A JP4048081A JPS6136821B2 JP S6136821 B2 JPS6136821 B2 JP S6136821B2 JP 4048081 A JP4048081 A JP 4048081A JP 4048081 A JP4048081 A JP 4048081A JP S6136821 B2 JPS6136821 B2 JP S6136821B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- compound
- present
- pentenyl
- angelic acid
- 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
Links
- -1 angelic acid ester Chemical class 0.000 claims description 10
- UIERETOOQGIECD-UHFFFAOYSA-N Angelic acid Natural products CC=C(C)C(O)=O UIERETOOQGIECD-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 description 26
- 239000000203 mixture Substances 0.000 description 23
- 239000003205 fragrance Substances 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000002304 perfume Substances 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 238000005809 transesterification reaction Methods 0.000 description 4
- 125000006057 3-methyl-4-pentenyl group Chemical group 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- YYJWBYNQJLBIGS-PLNGDYQASA-N methyl (z)-2-methylbut-2-enoate Chemical compound COC(=O)C(\C)=C/C YYJWBYNQJLBIGS-PLNGDYQASA-N 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 244000028419 Styrax benzoin Species 0.000 description 2
- 235000000126 Styrax benzoin Nutrition 0.000 description 2
- 235000008411 Sumatra benzointree Nutrition 0.000 description 2
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 2
- 229960002130 benzoin Drugs 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 235000019382 gum benzoic Nutrition 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- LHTVMBMETNGEAN-UHFFFAOYSA-N pent-1-en-1-ol Chemical compound CCCC=CO LHTVMBMETNGEAN-UHFFFAOYSA-N 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001577 simple distillation Methods 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000001414 (2E)-2-(phenylmethylidene)octanal Substances 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- BTSIZIIPFNVMHF-ONEGZZNKSA-N (E)-2-penten-1-ol Chemical compound CC\C=C\CO BTSIZIIPFNVMHF-ONEGZZNKSA-N 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- 125000006050 3-methyl-2-pentenyl group Chemical group 0.000 description 1
- VTCQTYOGWYLVES-UHFFFAOYSA-N 3-methylpent-4-en-1-ol Chemical compound C=CC(C)CCO VTCQTYOGWYLVES-UHFFFAOYSA-N 0.000 description 1
- 240000002045 Guettarda speciosa Species 0.000 description 1
- 235000001287 Guettarda speciosa Nutrition 0.000 description 1
- 244000178870 Lavandula angustifolia Species 0.000 description 1
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 1
- 241000234435 Lilium Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- 229940072717 alpha-hexylcinnamaldehyde Drugs 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- UIERETOOQGIECD-ARJAWSKDSA-N angelic acid Chemical compound C\C=C(\C)C(O)=O UIERETOOQGIECD-ARJAWSKDSA-N 0.000 description 1
- 150000001445 angelic acid derivatives Chemical class 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000010628 chamomile oil Substances 0.000 description 1
- 235000019480 chamomile oil Nutrition 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000010634 clove oil Substances 0.000 description 1
- 229960000956 coumarin Drugs 0.000 description 1
- 235000001671 coumarin Nutrition 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000000457 gamma-lactone group Chemical group 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000001102 lavandula vera Substances 0.000 description 1
- 235000018219 lavender Nutrition 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- BTSIZIIPFNVMHF-UHFFFAOYSA-N nor-leaf alcohol Natural products CCC=CCO BTSIZIIPFNVMHF-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000000606 toothpaste Substances 0.000 description 1
- 239000001529 viverra civetta schreber and viverra zibeth a schreber absolute Substances 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
Description
【発明の詳細な説明】
本発明は、香料に有用な性質を有する新規な化
合物とそれを含む香料に関するものである。更に
詳しく言えば本発明は、下記一般式（）で表わ
される新規なアンゲリカ酸エステルに関するもの
である。DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel compound having properties useful in perfumes and perfumes containing the same. More specifically, the present invention relates to a novel angelic acid ester represented by the following general formula ().
（式中点線はどちらか一方の側に二重結合が存
在することを示す）
アンゲリカ酸は下記構造式（）で表わされる
不飽和カルボン酸で、
正式名称は（Ｚ）―２―メチル―２―ブデン酸
である。アンゲリカ酸エステルのうち数種のもの
は天然精油、例えばカモミル油（カミツレ油）の
中に見出されており、香料成分として重要である
ことは広く知られている。 (The dotted line in the formula indicates the presence of a double bond on either side.) Angelic acid is an unsaturated carboxylic acid represented by the following structural formula (), The official name is (Z)-2-methyl-2-butic acid. Several types of angelic acid esters are found in natural essential oils, such as chamomile oil, and are widely known to be important as fragrance ingredients.
しかしながら、本発明の式（）の化合物は新
規な化合物であり、現在までに入手し得るどの文
献中にも記載されていない。 However, the compound of formula () of the present invention is a new compound and has not been described in any literature available to date.
本発明者らは、香料組成物に配合する場合に、
特に微量で香料の変調および香気の増強に効果の
ある化合物を鋭意検討した結果、前記一般式
（）で示される化合物が、この目的に効果のあ
る化合物であることを見出し、本発明に到達し
た。 The present inventors discovered that when blending into a fragrance composition,
As a result of intensive research into compounds that are effective in modulating fragrances and enhancing fragrance, particularly in minute amounts, the inventors discovered that the compound represented by the above general formula () is a compound effective for this purpose, and arrived at the present invention. .
本発明の一般式（）で示される化合物は、下
記の構造式（―ａ）を有する化合物
即ち、アンゲリカ酸３―メチル２―ペンテニ
ル、および下記の構造式（―ｂ）を有する化合
物
即ち、アンゲリカ酸３―メチル―４―ペンテニ
ルの二種の化合物である。 The compound represented by the general formula () of the present invention is a compound having the following structural formula (-a) That is, 3-methyl 2-pentenyl angelic acid and a compound having the following structural formula (-b) That is, they are two types of 3-methyl-4-pentenyl angelic acid compounds.
本発明の化合物はいずれもグリーンノートを有
し、香料素材として有用なものである。これら
は、どちらか一種でもあるいはその両方を使用し
ても良い。更に本発明化合物は他の香料組成物に
添加した場合、その香料組成物の香気を大きく改
善することが明らかとなつた。特に、香粧用香料
として使用される調合香料組成物に配合すると素
晴しい効果を発揮する化合物であることが明らか
となつた。 All of the compounds of the present invention have a green note and are useful as fragrance materials. Either one or both of these may be used. Furthermore, it has been revealed that when the compound of the present invention is added to other perfume compositions, it significantly improves the aroma of the perfume compositions. In particular, it has become clear that this compound exhibits a wonderful effect when added to a blended fragrance composition used as a fragrance for cosmetics.
本発明の化合物の香気の特性について更に詳し
く述べると、アンゲリカ酸３―メチル―２―ペン
テニル（―ａ）は、メタリツクなグリーン調で
揮発性の香りを有し、ジヤスモン調のナチユラル
感を出すのに特に有効である。特にフローラル
調、グリーン調およびシプレ調の調合香料に配合
してより一層のナチユラル感を出すのに特に有効
である。 To explain in more detail the aroma characteristics of the compounds of the present invention, 3-methyl-2-pentenyl angelic acid (-a) has a metallic greenish and volatile aroma, and gives off a diasmon-like natural feeling. It is particularly effective for It is particularly effective when blended with floral, green and chypre fragrances to create a more natural feel.
アンゲリカ酸―３―メチル―４―ペンテニル
（―ｂ）は、グリーン調の甘みおよびドライな
ウツデイー、スパイシーノートを有しフローラル
調およびグリーン調のコンパウンドに変調剤とし
て特に有効である。特にフローラル調およびグリ
ーン調の調合香料に配合することにより特に素晴
しい効果を演出する。 3-Methyl-4-pentenyl angelica acid (-b) has a greenish sweetness and a dry, nutty, spicy note and is particularly useful as a modulator in floral and greenish compounds. In particular, it produces a particularly wonderful effect when blended with floral and green fragrances.
本発明化合物は、化粧品（石けん、軟こう、パ
ウダー、練り歯みがき、脱臭剤、シヤンプー、オ
ーデコロン、ローシヨンなど）、洗剤などに添加
して芳香組成物（賦香組成物）としても使用で
き、また食品、嗜好品、飲料などに添加してフレ
ーバーとしても使用できる。 The compounds of the present invention can be added to cosmetics (soaps, ointments, powders, toothpastes, deodorants, shampoos, colognes, lotions, etc.), detergents, etc. and used as fragrance compositions (perfuming compositions). It can also be used as a flavor by adding it to luxury items and drinks.
本発明の化合物は前述のように、他の香料組成
物に配合して新たな香料組成物として使用される
場合に、更に良好な効果を発揮する。配合される
量はその目的および配合される香料組成物によつ
て変えられるが、一般には、配合された香料組成
物総重合の0.005〜50重量％が望ましく、より好
ましくは0.05〜30重量％が望ましい。 As mentioned above, the compound of the present invention exhibits even better effects when used as a new fragrance composition by blending it with another fragrance composition. The amount to be blended varies depending on the purpose and the perfume composition to be blended, but in general, it is preferably 0.005 to 50% by weight, more preferably 0.05 to 30% by weight of the total polymerized perfume composition. desirable.
実施例に代表的な配合例を示すが、もちろん本
発明はこれに限定されるものではない。 Typical formulation examples are shown in Examples, but the present invention is of course not limited thereto.
本発明化合物は例えば、次に記すような方法で
製造される。 The compound of the present invention can be produced, for example, by the method described below.
すなわち、アンゲリカ酸メチルエステルと本発
明化合物に対応するアルコール即ち３―メチル―
２―ペンテノールもしくは３―メチル―４―ペン
テノールとの混合物をエステル交換触媒の存在下
に処理することによつて目的のアンゲリカ酸エス
テルが得られる。 That is, angelic acid methyl ester and the alcohol corresponding to the compound of the present invention, that is, 3-methyl-
The desired angelic acid ester is obtained by treating a mixture with 2-pentenol or 3-methyl-4-pentenol in the presence of a transesterification catalyst.
目的化合物の精製は通常の精製手段例えば精留
によつて実施することが出来る。精留によれば、
原料の該アルコール、アンゲリカ酸メチルおよび
副生するメタノールと目的化合物を分離すること
が容易である。エステル交換触媒は精留の際釜残
として残るが、望ましくは、精留の前に単蒸留も
しくは、段数の低い塔を用いた精留により、比較
的短時間に揮発性反応混合物を留去することよつ
て、触媒から分離した方がよい。しかる後に精留
によつて目的化合物を純粋にとり出すことが出来
る。 Purification of the target compound can be carried out by conventional purification means such as rectification. According to rectification,
It is easy to separate the target compound from the alcohol as a raw material, methyl angelicate, and methanol as a by-product. The transesterification catalyst remains as a bottom residue during rectification, but preferably, the volatile reaction mixture is distilled off in a relatively short time by simple distillation or rectification using a column with a low number of plates before rectification. It is better to separate it from the catalyst. Thereafter, the target compound can be extracted in pure form by rectification.
エステル交換触媒としては、一般に酸が用いら
れるが、有機錫化合物やチタンのアルコキサイド
などの金属化合物も好適に用いられる。溶媒は反
応に悪い影響を与えないものであれば使用しても
差し支えないが、一般には無溶媒系でよい。その
他一般に用いられるエステル交換条件に準じて本
発明の化合物は製造される。 As the transesterification catalyst, acids are generally used, but metal compounds such as organotin compounds and titanium alkoxides are also suitably used. Any solvent may be used as long as it does not adversely affect the reaction, but generally a solvent-free system may be used. The compounds of the present invention are produced according to other commonly used transesterification conditions.
上記製造法においては副生するメタノールを留
去もしくはモレキユラシーブへの吸着のような手
段によつて反応混合物から連続的に除去する手段
を用いると反応はより収率よく進行する。一つの
具体的な製造例を以下の実施例に示すが本発明は
もちろんこれにより限定されるものではない。 In the above production method, the reaction proceeds with better yield if a means is used to continuously remove by-product methanol from the reaction mixture by distillation or adsorption onto molecular sieves. One specific manufacturing example is shown in the following example, but the present invention is of course not limited thereto.
実施例 １
アンゲリカ酸３―メチル―２―ペンテニルの製
造
アンゲリカ酸メチル22.8ｇ、３―メチル―２―
ペンテノール10ｇ、トルエン80ml、ジオクチル錫
ラウレート１ｇの混合物を300mlのガラス製フラ
スコに入れ、上部にモレキユラ―シーブ4Aを詰
めたソークスレー抽出器と還流冷却器をつける。
上記混合物を加熱し、継続的に還流するようにし
て還流液がモレキユラーシーブ4Aを通じてフラ
スコ内に戻るようにする。合計17時間加熱して得
られた混合物を単蒸留して115℃（22mmＨｇ）の
留分14.2ｇを得た。この留分を更に精留すること
により115℃（22mmＨｇ）で留出する留分9.70ｇ
を得た。この化合物はガスクロマトグラフイー
（カラム；シリコンSE―52 ２％／クロモソルブ
GHP）による分析で面積比による純度は99.403％
であつた。屈折率（Ｄ線、20℃）は1.463であつ
た。赤外スペクトル（液膜）においては、2850〜
3020，1720，1670，1650，1455，1385，1350，
1255，1225，1155，1080，1040，960，845，760
cm-1に吸収を示した。プロトン核磁気共鳴スペク
トル（重水素化クロロホルム中、TMS内部標
準）においては、δ＝1.01（三重線、3H）、1.72
〜2.10（多重線、11H）4.68（二重線、2H）、5.40
（多重線、1H）、6.03（多重線、1H）に吸収を示
した。Example 1 Production of 3-methyl-2-pentenyl angelate Methyl angelate 22.8 g, 3-methyl-2-
A mixture of 10 g of pentenol, 80 ml of toluene, and 1 g of dioctyltin laurate is placed in a 300 ml glass flask, and a Soxhlet extractor packed with 4A molecular sieve and a reflux condenser are attached to the top.
The mixture is heated and continuously refluxed so that the reflux liquid returns to the flask through the molecular sieve 4A. The mixture obtained by heating for a total of 17 hours was subjected to simple distillation to obtain 14.2 g of a fraction at 115°C (22 mmHg). By further rectifying this fraction, 9.70g of distillate is distilled at 115℃ (22mmHg)
I got it. This compound was analyzed by gas chromatography (column; silicone SE-52 2%/Chromosolve).
Purity by area ratio is 99.403% as analyzed by GHP)
It was hot. The refractive index (D line, 20°C) was 1.463. In the infrared spectrum (liquid film), 2850~
3020, 1720, 1670, 1650, 1455, 1385, 1350,
1255, 1225, 1155, 1080, 1040, 960, 845, 760
It showed absorption at cm -1 . In the proton nuclear magnetic resonance spectrum (in deuterated chloroform, TMS internal standard), δ = 1.01 (triplet, 3H), 1.72
~2.10 (multiplet, 11H) 4.68 (doublet, 2H), 5.40
(multiplet, 1H), showed absorption at 6.03 (multiplet, 1H).
実施例 ２
アンゲリカ酸３―メチル―４―ペンテニルの製
造
アンゲリカ酸メチル22.8ｇ、３―メチル―４―
ペンテノール10.0ｇ、トルエン100mlジオクチル
錫ラウレート0.9ｇの混合物を実施例１と同じ条
件で反応させて得た混合物を単蒸留して109℃
（21mmＨｇ）の留分16.91ｇを得た。このものを更
に精留にかけて109℃（21mmＨｇ）の留分12.54ｇ
を得た。この化合物を実施例１と同じ条件でガス
クロマトグラフイーで分析すると、面積比による
純度は99.653％であつた。屈折率は1.443であつ
た。Example 2 Production of 3-methyl-4-pentenyl angelate Methyl angelate 22.8g, 3-methyl-4-
A mixture of 10.0 g of pentenol, 100 ml of toluene, and 0.9 g of dioctyltin laurate was reacted under the same conditions as in Example 1. The mixture obtained was simply distilled at 109°C.
16.91 g of a fraction (21 mmHg) was obtained. This product is further rectified to yield 12.54g of distillate at 109℃ (21mmHg).
I got it. When this compound was analyzed by gas chromatography under the same conditions as in Example 1, the purity by area ratio was 99.653%. The refractive index was 1.443.
赤外スペクトル（液膜）においては、3075，
2850〜3000，1720，1650，1455，1435，1420，
1390，1380，1350，1260，1230，1160，1080，
1045，990，910，845，760cm-1に吸収を示した。 In the infrared spectrum (liquid film), 3075,
2850〜3000, 1720, 1650, 1455, 1435, 1420,
1390, 1380, 1350, 1260, 1230, 1160, 1080,
It showed absorption at 1045, 990, 910, 845, and 760 cm -1 .
プロトン核磁気共鳴スペクトル（重水素化クロ
ロホルム中、TMS内部標準）においては、δ＝
1.7〜2.04（多重線、9H）、2.41（三重線、2H）、
4.29（三重線、2H）、4.91（多重線、2H）6.06
（多重線、1H）に吸収を示した。 In proton nuclear magnetic resonance spectra (in deuterated chloroform, TMS internal standard), δ=
1.7~2.04 (multiplet, 9H), 2.41 (triplet, 2H),
4.29 (triplet, 2H), 4.91 (multiplet, 2H) 6.06
(multiplet, 1H) showed absorption.
実施例 ３
下記の組成で石けん用ラベンダー香料組成物を
調整した。Example 3 A lavender fragrance composition for soap was prepared with the following composition.
重量％
ラベンダー油モンブラン 50.0
ベルガモツト油 8.0
ボア・ド・ローズ 10.0
ゼラニウム油 5.0
ローズマリー油 5.0
クローブ油 2.5
パチユーリ油 5.0
ベンゾイン・シヤム 2.5
クマリン 4.0
ヘリオトロピン 5.0
アンゲリカ酸３―メチル―２―ペンテニル 3.0
合 計 100.0
上記組成物は３人の熟練した調香員により、ア
ンゲリカ酸３―メチル―２―ペンテニルを配合し
ない比較組成物に比して、より一層のナチユラル
感を有し、著しく優れていると判定された。 Weight% Lavender oil Mont Blanc 50.0 Bergamot oil 8.0 Bois de Rose 10.0 Geranium oil 5.0 Rosemary oil 5.0 Clove oil 2.5 Pachu lily oil 5.0 Benzoin Syam 2.5 Coumarin 4.0 Heliotropin 5.0 3-Methyl-2- pentenyl angelic acid 3.0 Total 100.0 The above composition was judged by three experienced perfumers to be significantly superior to a comparative composition that does not contain 3-methyl-2-pentenyl angelic acid, having a more natural feel. Ta.
実施例 ４
ジヤスミンコンパウンド
重量％
α―ヘキシルシンナムアルデヒド 75.0
ベンゾイン・シヤム 1.0
ジヤスミン・アブソリユート 5.0
ベンジルベンゾエート 3.0
ベンジルアセテート 8.0
リナロール 2.5
シベツト・アブソリユート10％（アルコール）
0.5
インドール10％ 3.0
シス―ジヤスモン 0.5
γ―ラクトンＣ―11 0.5
アンゲリカ酸３―メチル―４―ペンテニル 1.0
合 計 100.0
上記香料組成物は３人の熟練した調査員によ
り、アンゲリカ酸３―メチル―４―ペンテニルを
配合しない比較組成物に比して、より一層のナチ
ユラル感を有し、その調子が著しく優れていると
判定された。Example 4 Diasmine compound Weight % α-Hexylcinnamaldehyde 75.0 Benzoin Syam 1.0 Diasmine absolute 5.0 Benzyl benzoate 3.0 Benzyl acetate 8.0 Linalool 2.5 Civet absolute 10% (alcohol)
0.5 Indole 10% 3.0 Cis-Diasmone 0.5 γ-Lactone C-11 0.5 3-Methyl-4- Pentenyl Angelicate 1.0 Total 100.0 The above fragrance composition was determined by three experienced investigators to contain 3-methyl-4 Angelicate. -Compared to a comparative composition that does not contain pentenyl, it was judged to have a more natural feel and a significantly better tone.
Claims (1)
在することを示す）で表わされるアンゲリカ酸エ
ステル誘導体。 ２ 一般式（） （式中点線はどちらか一方の側に二重結合が存
在することを示す）で表わされる化合物を含有す
る香料組成物。[Claims] 1 General formula () An angelic acid ester derivative represented by (the dotted line in the formula indicates the presence of a double bond on either side). 2 General formula () (A dotted line in the formula indicates that a double bond is present on either side).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4048081A JPS57156436A (en) | 1981-03-23 | 1981-03-23 | Angelic ester derivative and perfume composition comprising it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4048081A JPS57156436A (en) | 1981-03-23 | 1981-03-23 | Angelic ester derivative and perfume composition comprising it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS57156436A JPS57156436A (en) | 1982-09-27 |
| JPS6136821B2 true JPS6136821B2 (en) | 1986-08-20 |
Family
ID=12581767
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4048081A Granted JPS57156436A (en) | 1981-03-23 | 1981-03-23 | Angelic ester derivative and perfume composition comprising it |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS57156436A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6461720A (en) * | 1987-09-02 | 1989-03-08 | Mitsubishi Electric Corp | Laser beam condensing device |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19939566C1 (en) * | 1999-08-20 | 2001-04-05 | Cognis Deutschland Gmbh | Branched, largely unsaturated ester oils, process for their preparation and their use for the production of cosmetic and / or pharmaceutical preparations |
| JP4896680B2 (en) * | 2006-11-27 | 2012-03-14 | 高砂香料工業株式会社 | Perfume composition, product containing the perfume composition, and novel ester compound |
-
1981
- 1981-03-23 JP JP4048081A patent/JPS57156436A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6461720A (en) * | 1987-09-02 | 1989-03-08 | Mitsubishi Electric Corp | Laser beam condensing device |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS57156436A (en) | 1982-09-27 |
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