JP2754135B2 - Novel ketone and fragrance composition containing the same - Google Patents
Novel ketone and fragrance composition containing the sameInfo
- Publication number
- JP2754135B2 JP2754135B2 JP16480693A JP16480693A JP2754135B2 JP 2754135 B2 JP2754135 B2 JP 2754135B2 JP 16480693 A JP16480693 A JP 16480693A JP 16480693 A JP16480693 A JP 16480693A JP 2754135 B2 JP2754135 B2 JP 2754135B2
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- fragrance
- fragrance composition
- composition containing
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Description
【０００１】[0001]
【産業上の利用分野】本発明は、アニマル、アンバー様
香気を有する新規なケトン、及びこれを含有する香料組
成物に関する。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel ketone having an animal and amber-like odor, and a fragrance composition containing the same.
【０００２】[0002]
【従来の技術及び発明が解決しようとする課題】従来、
ラブダナム精油は、植物由来の天然アンバー素材として
幅広い用途に使用されており（Ｓ．Ａｒｃｔａｎｄｅ
ｒ，Ｐｅｒｆｕｍｅ ａｎｄ Ｆｌａｖｏｒ Ｃｈｅｍ
ｉｃａｌｓ；奥田治、香料化学総覧）、精油に含まれて
いる成分と香りについても、かなり研究が行われてい
る。特に、ラブダナム特有のアニマル、アンバー様香気
成分を探索することは、新しい香料を得るためにも極め
て重要であるが、これらの香気成分については未だ知ら
れていなかった。2. Description of the Related Art
Rabdanum essential oil is used for a wide range of applications as a natural amber material derived from plants (S. Arctande).
r, Perfume and Flavor Chem
icals; Okuda Osamu, Perfumery Chemistry Directory), and the components and aromas contained in essential oils have also been studied considerably. In particular, it is extremely important to search for animal and amber-like fragrance components unique to Labdanum, in order to obtain a new fragrance, but these fragrance components have not been known yet.
【０００３】従って、新規な香料成分、特にアニマル、
アンバー様香気を有し、調合香料素材として有用な化合
物の開発が望まれていた。[0003] Accordingly, new perfume ingredients, especially animals,
It has been desired to develop a compound having an amber-like scent and useful as a compounded fragrance material.
【０００４】[0004]
【課題を解決するための手段】かかる実情において、本
発明者らは鋭意研究を行った結果、ラブダナム精油から
分離した後記式（１）で表わされるケトンが、アニマ
ル、アンバー様香気を有し、種々の調合香料素材として
有用であることを見出し、本発明を完成した。Under such circumstances, the present inventors have conducted intensive studies and as a result, the ketone represented by the following formula (1) separated from the essential oil of Labdanum has an animal-like, amber-like odor, The present invention was found to be useful as various compounded fragrance materials and completed the present invention.
【０００５】すなわち、本発明は、次式（１）That is, the present invention provides the following formula (1)
【０００６】[0006]
【化４】 Embedded image
【０００７】で表わされる４−（３−メチル−３−ブテ
ニル）−４α，５，６，７，８，８α−ヘキサヒドロ−
３，４α，８，８−テトラメチル−２（１Ｈ）−ナフタ
レノン、及びこれを含有する香料組成物を提供するもの
である。4- (3-methyl-3-butenyl) -4α, 5,6,7,8,8α-hexahydro-
It is intended to provide 3,4α, 8,8-tetramethyl-2 (1H) -naphthalenone and a fragrance composition containing the same.
【０００８】本発明のケトン化合物（１）は、Ｃｉｓｔ
ｕｓ種のＣｉｓｔｕｓ Ｌａｄａｎｉｆｅｒｕｓ．Ｌの
精油（ラブダナム精油）中に含有される化合物であり、
例えば、粗ラブダナム精油であるラブダナムガムから以
下の方法に従って単離することができる。[0008] The ketone compound (1) of the present invention can be obtained from Cist
Cistus Ladaniferus. L is a compound contained in the essential oil of L (Rabdanum essential oil),
For example, it can be isolated from labdanum gum, a crude labdanum essential oil, according to the following method.
【０００９】なお、ラブダナムガムは、Ｃｉｓｔｕｓ
Ｌａｄａｎｉｆｅｒｕｓ．Ｌを水中、一般的にはアルカ
リ水中で煮沸することにより分離してくる樹脂をすくい
取ることにより得られるものであり、これは市販品を用
いることもできる。[0009] Love Dunham gum is available from Cistus.
Ladaniferus. L is obtained by scooping the resin which separates by boiling in water, generally alkaline water, and a commercially available product can also be used.
【００１０】本発明のケトン化合物（１）を得るために
は、まずラブダナムガムに、エーテル、石油エーテル、
メタノール、エタノール、ヘキサン、トルエンなどの有
機溶剤を添加し、静置もしくは撹拌して抽出液を得、更
に該抽出液から有機溶剤を留去して処理ラブダナム油を
得る。次にこの処理ラブダナム油の酸性成分を、水酸化
ナトリウム、水酸化カリウムなどのアルカリ溶液で抽出
し、次いで塩酸又は硫酸を用いて中和した後、石油エー
テル、ヘキサン、トルエン等の有機溶媒を用いて再抽出
する。更に溶媒を留去し、得られた抽出物を窒素雰囲気
下、２００〜３５０℃まで加熱して、アニマル香を強く
した改質ラブダナム油を得る。To obtain the ketone compound (1) of the present invention, first, ether, petroleum ether,
An organic solvent such as methanol, ethanol, hexane, or toluene is added, and the mixture is allowed to stand or stirred to obtain an extract, and the organic solvent is distilled off from the extract to obtain a treated Rabdanum oil. Next, the acidic component of the treated Labdanum oil is extracted with an alkaline solution such as sodium hydroxide or potassium hydroxide, and then neutralized with hydrochloric acid or sulfuric acid, and then with an organic solvent such as petroleum ether, hexane, and toluene. And re-extract. Further, the solvent is distilled off, and the obtained extract is heated to 200 to 350 ° C. under a nitrogen atmosphere to obtain a modified Rabdanum oil having a stronger animal fragrance.
【００１１】このようにして得られた改質ラブダナム油
を、例えば蒸留することにより分離して揮発性成分を得
る。得られた留出液を、例えばシリカゲルカラムに吸着
させ、例えばヘキサン等の有機溶剤で展開して炭化水素
成分を溶出させ、次いで、例えばヘキサン−エーテルの
混合溶液で展開し、酢酸エチルの濃度を順次上げて溶出
させる。このようにして展開流出する液を適当量の画分
に分け、本発明化合物（１）を含む画分を集合する。次
に、溶媒を留去し、残渣を高速液体クロマトグラフィー
で、例えばヘキサン−エーテル混合溶液を用いて展開さ
せ、本発明化合物（１）を単離することができる。The modified Rabdanum oil thus obtained is separated by, for example, distillation to obtain a volatile component. The obtained distillate is adsorbed on, for example, a silica gel column, and eluted with an organic solvent such as hexane to elute hydrocarbon components, and then eluted with, for example, a mixed solution of hexane-ether to reduce the concentration of ethyl acetate. Raise and elute sequentially. In this way, the liquid that has developed and flowed out is divided into appropriate amounts of fractions, and the fractions containing the compound (1) of the present invention are collected. Next, the solvent is distilled off, and the residue is developed by high performance liquid chromatography using, for example, a mixed solution of hexane and ether, to isolate the present compound (1).
【００１２】このようにして得られる本発明のケトン化
合物（１）は、アニマル、フェノリックアンバー様香気
を有し、若干タバコ様香気も有するものであり、種々の
調合香料素材として有用である。The ketone compound (1) of the present invention thus obtained has an animal and phenolic amber-like odor, and also has a slightly tobacco-like odor, and is useful as a variety of compounded fragrance materials.
【００１３】かかる本発明化合物（１）の香料組成物へ
の配合量は、対象とする調合香料、目的とする香気等に
よって異なり、特に制限されないが、組成物中に０．１
〜１０重量％配合するのが好ましく、特に好ましくは１
〜５重量％である。The amount of the compound (1) of the present invention to be added to the fragrance composition varies depending on the target compounded fragrance, the intended fragrance and the like, and is not particularly limited.
-10% by weight, particularly preferably 1% by weight.
~ 5% by weight.
【００１４】本発明化合物（１）は、フェニルエチルア
ルコール、シトロネロール及びリナロールから選ばれる
香料化合物と共に使用すると、より自然の花様の瑞々し
さが増強される。本発明化合物（１）とフェニルエチル
アルコールとの配合割合が１：６０〜１：２０、シトロ
ネロールとの配合割合が１：５〜１：２０、リナロール
との配合割合が１：６０〜１：２０であると、瑞々しさ
がより強く感じられる。When the compound (1) of the present invention is used together with a fragrance compound selected from phenylethyl alcohol, citronellol and linalool, the freshness of natural flowers is enhanced. The compounding ratio of the present compound (1) to phenylethyl alcohol is 1:60 to 1:20, the compounding ratio to citronellol is 1: 5 to 1:20, and the compounding ratio to linalool is 1:60 to 1:20. Then, the freshness is felt more strongly.
【００１５】また、本発明の香料組成物は、前記の本発
明化合物を含有するものであるが、他に任意成分とし
て、通常の香料組成物に用いられる基剤成分や他の香料
成分、例えばフタル酸ジエチル、ジプロピレングリコー
ル、エチルジグリコール、ヘルコリンＤ（ジヒドロアビ
エチン酸メチル）、また、天然香料としては、例えばサ
ンダルウッド油、パチュリ油等を、本発明の効果を損わ
ない範囲で配合することができる。The fragrance composition of the present invention contains the above-mentioned compound of the present invention. In addition, as an optional component, a base component or another fragrance component used in a general fragrance composition, for example, Diethyl phthalate, dipropylene glycol, ethyl diglycol, hercholine D (methyl dihydroabietic acid), and natural fragrances such as sandalwood oil and patchouli oil are blended within a range that does not impair the effects of the present invention. be able to.
【００１６】本発明の香料組成物は、本発明化合物
（１）と任意成分とを、常法により混合、撹拌すること
により製造することができる。The fragrance composition of the present invention can be produced by mixing and stirring the compound (1) of the present invention and optional components in a conventional manner.
【００１７】本発明の香料組成物は、香水、コロン、石
ケン、シャンプー、リンス、身体洗浄剤、洗剤、化粧
品、スプレー、浴用剤、芳香剤等の賦香を必要とされる
ものに広汎に使用することができる。The fragrance composition of the present invention is widely used for perfumes, colons, soaps, shampoos, rinses, body cleansers, detergents, cosmetics, sprays, bath agents, fragrances and other substances requiring fragrance. Can be used.
【００１８】[0018]
【発明の効果】本発明化合物（１）は、アニマル、アン
バー様香気を有し、種々の調合香料素材として有用であ
り、これを含有する香料組成物は香水、石ケン等に好適
に使用することができる。The compound (1) of the present invention has an animal and amber-like odor and is useful as a variety of compounded fragrance materials, and the fragrance composition containing it is suitably used for perfumes, soaps and the like. be able to.
【００１９】[0019]
【実施例】次に、実施例を挙げて本発明を更に説明する
が、本発明はこれら実施例に限定されるものではない。EXAMPLES Next, the present invention will be further described with reference to examples, but the present invention is not limited to these examples.
【００２０】実施例１ 撹拌器、温度計及びジムロートのついた５００ccの４つ
口フラスコに、ラブダナムガムのエタノール抽出物であ
るラブダナムレジノイド（ＢＩＯ）２００ｇ、１０％水
酸化ナトリウム水溶液２００ｇ及びトルエン４００ｇを
加え、窒素ガス雰囲気下、９０℃で３０分撹拌した。そ
の後、静置分液してトルエン層を除去した。水層に更に
トルエン４００ｇを加え、同様に撹拌し静置分液してト
ルエン層を除去した。得られた水層にトルエン４００ｇ
を加えて撹拌し、濃硫酸２５ｇを槽内温度に注意しなが
らゆっくり滴下した。滴下後、窒素ガス雰囲気下、９０
℃まで昇温した。次いで、静置分液して水層を除去し
た。得られた油層に１０％芒硝水を加えて撹拌し、静置
分層し、油層からトルエンを留去し、残留物としてラブ
ダナム油酸性部７１ｇを得た。得られた酸性部５０ｇを
窒素ガス雰囲気下、２６０℃で３０分加熱撹拌した。槽
内温度を１００℃まで冷却し、流動パラフィン＃６０ｓ
（中央化成、ｂｐ２７８〜４２２℃）５０ｇを滴下し、
減圧下初留（〜１５０℃／２Ｔｏｒｒ）を除去し、更に
温度を上げ、蒸留留分（１８５〜２４０℃／２Ｔｏｒ
ｒ）５９ｇを得た。得られた蒸留留分３．０ｇについ
て、シリカゲル（ＷＡＫＯＧＥＬ Ｃ−３００）のカラ
ムクロマトを行った。まずヘキサン３００ml、次にヘキ
サン：エーテル＝９０：１０の溶媒１００mlを流した。
その後、ヘキサン：エーテル＝９０：１０の溶媒１００
mlを流し、留分１（０．５ｇ）を得た。留分１について
ＨＰＬＣ（ヘキサン／エーテル＝９０／１０）にて分取
し、本発明化合物（１）が５８％純度まで濃縮された留
分（１６０mg）を得、これを更にＨＰＬＣ分取（ヘキサ
ン／エーテル＝９５／５）し、本発明の４−（３−メチ
ル−３−ブテニル）−４α，５，６，７，８，８α−ヘ
キサヒドロ−３，４α，８，８−テトラメチル−２（１
Ｈ）−ナフタレノンを８０mg得た。Example 1 In a 500 cc four-necked flask equipped with a stirrer, a thermometer and a Dimroth, 200 g of Rabdanum resinoid (BIO), an ethanol extract of Rabdanum gum, 200 g of a 10% aqueous sodium hydroxide solution and 400 g of toluene were placed. In addition, the mixture was stirred at 90 ° C. for 30 minutes in a nitrogen gas atmosphere. Thereafter, the mixture was allowed to stand still to remove the toluene layer. 400 g of toluene was further added to the aqueous layer, and the mixture was similarly stirred and allowed to stand still for liquid separation to remove the toluene layer. 400 g of toluene was added to the obtained aqueous layer.
And stirred, and 25 g of concentrated sulfuric acid was slowly added dropwise while paying attention to the temperature in the tank. After dropping, under a nitrogen gas atmosphere, 90
The temperature was raised to ° C. Next, the aqueous layer was removed by standing liquid separation. 10% Glauber's salt water was added to the obtained oil layer, and the mixture was stirred and allowed to stand. The layers were separated, and toluene was distilled off from the oil layer to obtain 71 g of an acidic part of Rabdanum oil as a residue. 50 g of the obtained acidic part was heated and stirred at 260 ° C. for 30 minutes in a nitrogen gas atmosphere. Cool the temperature in the tank to 100 ° C, liquid paraffin # 60s
(Chuo Kasei, bp 278-422 ° C) 50 g was added dropwise,
The initial distillate (〜150 ° C./2 Torr) was removed under reduced pressure, the temperature was further raised, and the distillate fraction (185-240 ° C./2 Torr) was removed.
r) 59 g were obtained. Column chromatography of silica gel (WAKOGEL C-300) was performed on 3.0 g of the obtained distillation fraction. First, 300 ml of hexane and then 100 ml of a 90:10 hexane: ether solvent were passed.
Then, hexane: ether = 90: 10 solvent 100
Then, ml was flown to obtain a fraction 1 (0.5 g). The fraction 1 was fractionated by HPLC (hexane / ether = 90/10) to obtain a fraction (160 mg) in which the present compound (1) was concentrated to a purity of 58%, which was further fractionated by HPLC (hexane / Ether = 95/5) to give 4- (3-methyl-3-butenyl) -4α, 5,6,7,8,8α-hexahydro-3,4α, 8,8-tetramethyl-2 of the present invention. (1
80 mg of H) -naphthalenone were obtained.
【００２１】1H-NMR(CDCl3)δ：0.89(s,3H), 0.92(s,3
H), 1.10(s,3H),1.21〜1.74(m,5H), 1.77(s,3H), 1.78
(s,3H),2.10〜2.58(m,8H), 4.75(s,2H)ppm13 C-NMR(CDCl3)δ：11.3, 18.1, 18.6, 21.3, 22.4, 2
8.1, 32.5, 33.2,35.3, 35.8, 36.7, 41.2, 41.3, 50.
3, 110.1, 130.1,145.3, 167.9, 200.3ppm MS(70eV)：274(M), 259(M-15), 205(M-69) IR；1695cm-1(C=0) 1 H-NMR (CDCl 3 ) δ: 0.89 (s, 3H), 0.92 (s, 3
H), 1.10 (s, 3H), 1.21 ~ 1.74 (m, 5H), 1.77 (s, 3H), 1.78
(s, 3H), 2.10 to 2.58 (m, 8H), 4.75 (s, 2H) 13 C-NMR (CDCl 3 ) δ: 11.3, 18.1, 18.6, 21.3, 22.4, 2
8.1, 32.5, 33.2, 35.3, 35.8, 36.7, 41.2, 41.3, 50.
3, 110.1, 130.1, 145.3, 167.9, 200.3 ppm MS (70 eV): 274 (M), 259 (M-15), 205 (M-69) IR; 1695 cm -1 (C = 0)
【００２２】実施例２ 表１に示す組成のミューゲ様香料組成物を常法により製
造した。Example 2 A mug-like fragrance composition having the composition shown in Table 1 was produced by a conventional method.
【００２３】[0023]
【表１】 [Table 1]
【００２４】本発明の香料組成物は、比較品に比べ、水
々しさ、甘さ、柔らかさが強調されたミューゲ様香気を
有するものであった。The fragrance composition of the present invention had a mugue-like fragrance in which the freshness, sweetness and softness were emphasized as compared with the comparative product.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 藤倉 芳明 栃木県宇都宮市山本町271−６ (58)調査した分野(Int.Cl.6，ＤＢ名) C07C 49/587 - 49/757 A61K 7/46 C11B 9/00 - 9/02 ＣＡ（ＳＴＮ) ＲＥＧＩＳＴＲＹ（ＳＴＮ)────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Yoshiaki Fujikura 271-6 Yamamotocho, Utsunomiya City, Tochigi Prefecture (58) Field surveyed (Int. Cl. 6 , DB name) C07C 49/587-49/757 A61K 7 / 46 C11B 9/00-9/02 CA (STN) REGISTRY (STN)
Claims (3)
α，５，６，７，８，８α−ヘキサヒドロ−３，４α，
８，８−テトラメチル−２（１Ｈ）−ナフタレノン。1. The following formula (1) 4- (3-methyl-3-butenyl) -4 represented by
α, 5,6,7,8,8α-hexahydro-3,4α,
8,8-Tetramethyl-2 (1H) -naphthalenone.
α，５，６，７，８，８α−ヘキサヒドロ−３，４α，
８，８−テトラメチル−２（１Ｈ）−ナフタレノンを含
有する香料組成物。2. The following formula (1): 4- (3-methyl-3-butenyl) -4 represented by
α, 5,6,7,8,8α-hexahydro-3,4α,
A fragrance composition containing 8,8-tetramethyl-2 (1H) -naphthalenone.
α，５，６，７，８，８α−ヘキサヒドロ−３，４α，
８，８−テトラメチル−２（１Ｈ）−ナフタレノン並び
にフェニルエチルアルコール、シトロネロール及びリナ
ロールから選ばれる香料化合物を含有する香料組成物。3. The following formula (1): 4- (3-methyl-3-butenyl) -4 represented by
α, 5,6,7,8,8α-hexahydro-3,4α,
A perfume composition comprising 8,8-tetramethyl-2 (1H) -naphthalenone and a perfume compound selected from phenylethyl alcohol, citronellol and linalool.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16480693A JP2754135B2 (en) | 1993-07-02 | 1993-07-02 | Novel ketone and fragrance composition containing the same |
| ES94110263T ES2126678T3 (en) | 1993-07-01 | 1994-07-01 | TREATED LADANO OIL, PROCEDURE TO PREPARE IT, NEW KETOMIC COMPOUND, PERFUME COMPOSITION THAT UNDERSTANDS IT. |
| DE1994615424 DE69415424T2 (en) | 1993-07-01 | 1994-07-01 | Treated labdanum oil, process for making the same, new ketone compound and perfume composition containing it |
| EP19940110263 EP0634474B1 (en) | 1993-07-01 | 1994-07-01 | Treated labdanum oil, process for preparing the same, novel ketone compound, and perfume composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16480693A JP2754135B2 (en) | 1993-07-02 | 1993-07-02 | Novel ketone and fragrance composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0717893A JPH0717893A (en) | 1995-01-20 |
| JP2754135B2 true JP2754135B2 (en) | 1998-05-20 |
Family
ID=15800277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16480693A Expired - Lifetime JP2754135B2 (en) | 1993-07-01 | 1993-07-02 | Novel ketone and fragrance composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2754135B2 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113989A (en) * | 2013-03-07 | 2013-05-22 | 华宝食用香精香料（上海）有限公司 | Tobacco essence capable of improving cigarette taste and aroma |
-
1993
- 1993-07-02 JP JP16480693A patent/JP2754135B2/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103113989A (en) * | 2013-03-07 | 2013-05-22 | 华宝食用香精香料（上海）有限公司 | Tobacco essence capable of improving cigarette taste and aroma |
| CN103113989B (en) * | 2013-03-07 | 2014-02-26 | 华宝食用香精香料（上海）有限公司 | Tobacco essence capable of improving cigarette taste and aroma |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0717893A (en) | 1995-01-20 |
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