JP2686828B2 - 2-Cyclohexylpropanol derivative and fragrance composition containing the same - Google Patents
2-Cyclohexylpropanol derivative and fragrance composition containing the sameInfo
- Publication number
- JP2686828B2 JP2686828B2 JP1202029A JP20202989A JP2686828B2 JP 2686828 B2 JP2686828 B2 JP 2686828B2 JP 1202029 A JP1202029 A JP 1202029A JP 20202989 A JP20202989 A JP 20202989A JP 2686828 B2 JP2686828 B2 JP 2686828B2
- Authority
- JP
- Japan
- Prior art keywords
- compound
- cyclohexylpropanol
- derivative
- cyclohexylpropyl
- composition containing
- 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.)
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Landscapes
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fats And Perfumes (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は新規な化合物及びこれを含有する香料組成物
に関する。TECHNICAL FIELD The present invention relates to a novel compound and a perfume composition containing the same.
２−シクロヘキシルプロパノールは純粋な状態ではバ
ルサム様、花様の香りを有することが知られている。し
かしながら、この化合物を工業的に製造した場合、副生
物が生成してしまい、純粋なもの、すなわち良好な香気
のものは得られない。従って「パーヒューム アンド
フレーバ ケミカルズ（Perfume and Flavor Chemical
s）」、S.アークテンダー著（1969年）によれば香料と
して有用なものとしては取扱われていない。更に、一般
的には、このようなアルコール系香料をエステル化、エ
ーテル化等して得られた誘導体も香料として有用なもの
が多いが、２−シクロヘキシルプロパノールの誘導体に
ついては上記副生物生成のためその報告は皆無であっ
た。2-Cyclohexyl propanol is known to have a balsam-like and flower-like aroma in a pure state. However, when this compound is industrially produced, a by-product is produced and a pure product, that is, a product having a good odor is not obtained. Therefore, "Perfume and
Flavor Chemicals (Perfume and Flavor Chemical
According to S. Arctender (1969), it is not treated as a useful fragrance. Furthermore, in general, many derivatives obtained by esterifying or etherifying such alcoholic fragrances are also useful as fragrances, but the derivative of 2-cyclohexylpropanol is used for the above by-product formation. There was no report.
上記実情に鑑み、本発明者らは前記副生物がなく香料
として価値のある２−シクロヘキシルプロパノールを工
業的に製造する方法（特願昭63-259321号）を見い出
し、更にこのようにして製造された２−シクロヘキシル
プロパノールを原料として種々の誘導体を合成し、その
香気性について検討したところ、特定の基をもつ誘導体
が、果実様、木様、バラ様、草様の香りを有し、香料と
して有用であることを見い出し本発明を完成した。In view of the above situation, the present inventors have found a method (Japanese Patent Application No. 63-259321) for industrially producing 2-cyclohexylpropanol, which is valuable as a fragrance without the by-product, and is further produced in this manner. When various derivatives were synthesized using 2-cyclohexyl propanol as a raw material and the aroma was examined, the derivative having a specific group had a fruity, tree-like, rose-like, or grass-like scent and was used as a fragrance. The present invention has been found to be useful and the present invention has been completed.
すなわち本発明は、次の一般式（Ｉ） 〔式中、Ｒは炭素数１〜３のアルキル基、アリル基、ベ
ンジル基又は−COR′（Ｒ′は炭素数２〜３のアルキル
基又はエトキシ基を示す）を示す〕 で表される２−シクロヘキシルプロパノール誘導体及び
これを含有することを特徴とする香料組成物を提供する
ものである。That is, the present invention provides the following general formula (I) [In the formula, R represents an alkyl group having 1 to 3 carbon atoms, an allyl group, a benzyl group or -COR '(R' represents an alkyl group having 2 to 3 carbon atoms or an ethoxy group)] -A cyclohexyl propanol derivative and a fragrance composition containing the same are provided.
本発明化合物（Ｉ）は、例えば次の（Ａ）又は（Ｂ）
のいずれかの方法によって製造される。The compound (I) of the present invention includes, for example, the following (A) or (B)
Manufactured by any one of the above methods.
（Ａ）法： 〔式中、Ｒ1は炭素数１〜３のアルキル基、アリル基、
又はベンジル基を示し、Ｘはハロゲン原子又は硫酸根を
示し、Ｙはアルカリ金属を示す〕 すなわち、アルコールを原料としたエーテルの一般的
合成法であるWilliamson反応（例えば、日本化学会編
「新実験化学講座」（丸善）、第14巻p.568〜574）に従
い、２−シクロヘキシルプロパノールをアルカリ金属、
アルカリ金属水素化物等の強アルカリと反応させてアル
カリ金属アルコラートとした後、これにアルキル硫酸エ
ステル、ハロゲン化アルキル（アルケニル）等のアルキ
ル化剤を反応させれば、本発明化合物（Ia）が製造され
る。Method (A): [In the formula, R 1 is an alkyl group having 1 to 3 carbon atoms, an allyl group,
Or a benzyl group, X represents a halogen atom or a sulfate group, and Y represents an alkali metal] That is, the Williamson reaction (for example, "New Experiment" edited by the Chemical Society of Japan Chemistry "(Maruzen), Vol. 14, p. 568-574), 2-cyclohexyl propanol as an alkali metal,
The compound (Ia) of the present invention can be produced by reacting with a strong alkali such as an alkali metal hydride to form an alkali metal alcoholate, and then reacting this with an alkylating agent such as an alkyl sulfate ester or a halogenated alkyl (alkenyl). To be done.
例えば強アルカリとしては水素化ナトリウム、アルキ
ル化剤として臭化アルキル（アルケニル）を用いた場合
の反応は次の如くして行なわれる。すなわち、反応溶媒
としてベンゼン、トルエン、キシレン等を用い、反応温
度60℃〜140℃にて２−シクロヘキシルプロパノールに
水素化ナトリウムを反応させてナトリウムアルコラート
とし、さらに反応温度60℃〜140℃にて、臭化アルキル
（アルケニル）を反応せしめれば本発明化合物（Ia）を
得ることができる。For example, when sodium hydride is used as the strong alkali and alkyl bromide (alkenyl) is used as the alkylating agent, the reaction is carried out as follows. That is, using benzene, toluene, xylene and the like as a reaction solvent, 2-cyclohexyl propanol is reacted with sodium hydride at a reaction temperature of 60 ° C to 140 ° C to give sodium alcoholate, and further at a reaction temperature of 60 ° C to 140 ° C. The compound (Ia) of the present invention can be obtained by reacting with an alkyl (alkenyl) bromide.
（Ｂ）法： 〔式中、Ｒ′は前記と同じものを示す〕 すなわち、アルコールを原料としたエステルの一般的
合成法、例えば前記「新実験化学講座」第14巻p.1000〜
1021の記載に従い、アルコールにカルボン酸又は酸ハラ
イド、酸無水物、活性エステル等のカルボン酸誘導体を
反応させることにより本発明化合物（Ib）が製造され
る。(B) method: [In the formula, R'represents the same as above] That is, a general method for synthesizing an ester using alcohol as a raw material, for example, "New Experimental Chemistry Course", Vol. 14, p.1000-
As described in 1021, the compound (Ib) of the present invention is produced by reacting an alcohol with a carboxylic acid or a carboxylic acid derivative such as an acid halide, an acid anhydride or an active ester.
具体的には、例えば反応溶媒としてヘキサン、シクロ
ヘキサン、ベンゼン、トルエン、キシレン、エーテル又
はテトラヒドロフラン等を用い、２−シクロヘキシルプ
ロパノール１当量にピリジン若しくはジメチルアニリン
等の第三級アミン1.0〜1.2当量と酸クロリド若しくは酸
無水物1.0〜1.2当量を、温度０℃〜60℃にて反応せしめ
れば本発明化合物（Ib）を得ることができる。Specifically, for example, hexane, cyclohexane, benzene, toluene, xylene, ether, tetrahydrofuran or the like is used as a reaction solvent, and 1-equivalent of 2-cyclohexylpropanol contains 1.0-1.2 equivalents of a tertiary amine such as pyridine or dimethylaniline and acid chloride. Alternatively, the compound (Ib) of the present invention can be obtained by reacting 1.0 to 1.2 equivalents of acid anhydride at a temperature of 0 to 60 ° C.
以上の如くして得られる本発明化合物（Ｉ）の代表的
化合物は、次の表１に示す如き香気を有する。Representative compounds of the compound (I) of the present invention obtained as described above have the odors shown in Table 1 below.
本発明化合物（Ｉ）の香料組成物への配合量は、特に
限定されないが、１〜40重量％、特に５〜30重量％が好
ましい。 The compounding amount of the compound (I) of the present invention in the perfume composition is not particularly limited, but is preferably 1 to 40% by weight, particularly preferably 5 to 30% by weight.
本発明化合物（Ｉ）は強い果実様、木様、ラクトン
様、草様の香りを有することから、例えば高級な香料組
成物、香水、石鹸、シャンプー、リンス、洗剤、化粧
品、スプレー、芳香剤等の賦香を必要とされるものに広
汎に使用できる。Since the compound (I) of the present invention has a strong fruit-like, woody, lactone-like, or grass-like fragrance, for example, high-grade fragrance compositions, perfumes, soaps, shampoos, rinses, detergents, cosmetics, sprays, aromatics, etc. Can be used extensively for those requiring perfume.
次に実施例を挙げて本発明を説明する。 Next, the present invention will be described with reference to examples.
実施例１ ２−シクロヘキシルプロピルメチルエーテル（本発明化
合物１）の合成： 300ml丸底フラスコに窒素気流下、水素化ナトリウム6
0wt％鉱油分散品6.2g及びトルエン50mlを仕込み、100℃
に加熱した。ここに２−シクロヘキシルプロパノール20
gとトルエン20mlの混合物をゆっくり滴下した。この
後、100℃で１時間撹拌し、水素の発生が止まったこと
を確認してから硫酸ジメチル19.5gをゆっくり滴下し、
さらに100℃で２時間撹拌した。得られた反応混合物を5
0℃まで冷却後10％水酸化ナトリウム水溶液を70mlゆっ
くり加え、さらに80℃で１時間撹拌した。反応混合物を
冷却後、水層を分離してから有機層を水洗し、減圧にて
蒸留を行ったところ２−シクロヘキシルプロピルメチル
エーテル19.4g（収率88％、沸点60℃/5mmHg）が得られ
た。Example 1 Synthesis of 2-cyclohexylpropyl methyl ether (Compound 1 of the invention): Sodium hydride 6 in a 300 ml round bottom flask under nitrogen stream.
Charge 6.2 g of 0 wt% mineral oil dispersion and 50 ml of toluene at 100 ° C.
Heated. 2-cyclohexyl propanol 20 here
A mixture of g and 20 ml of toluene was slowly added dropwise. After that, stir at 100 ° C for 1 hour, and after confirming that the generation of hydrogen has stopped, slowly add 19.5 g of dimethyl sulfate,
The mixture was further stirred at 100 ° C for 2 hours. The reaction mixture obtained is 5
After cooling to 0 ° C, 70 ml of 10% aqueous sodium hydroxide solution was slowly added, and the mixture was further stirred at 80 ° C for 1 hour. After cooling the reaction mixture, the aqueous layer was separated, the organic layer was washed with water, and distilled under reduced pressure to give 2-cyclohexylpropyl methyl ether (19.4 g, yield 88%, boiling point 60 ° C / 5 mmHg). It was
IR（液膜,cm-1）:2928,2856,1452,1144,1120 NMR（CDCl3，δ,TMS内部標準,ppm）:0.87（d,J＝7Hz,3
H）,0.9-2.0（m,12H）,3.20（d,J＝7Hz,1H）,3.26（d,J
＝7Hz,1H）,3.31（s,3H） GC-MS（Ｍ+）:156 実施例２ ２−シクロヘキシルプロピルエチルエーテル（本発明化
合物２）の合成： 実施例１において用いた硫酸ジメチルの替りに硫酸ジ
エチル23.7gを用い、その他は実施例１と同様な操作を
行い、２−シクロヘキシルプロピルエチルエーテル20.4
g（収率85％、沸点71℃/5mmHg）を得た。IR (liquid film, cm -1 ): 2928,2856,1452,1144,1120 NMR (CDCl 3 , δ, TMS internal standard, ppm): 0.87 (d, J = 7Hz, 3
H), 0.9-2.0 (m, 12H), 3.20 (d, J = 7Hz, 1H), 3.26 (d, J
= 7 Hz, 1H), 3.31 (s, 3H) GC-MS (M + ): 156 Example 2 Synthesis of 2-cyclohexylpropyl ethyl ether (inventive compound 2): Instead of dimethyl sulfate used in Example 1. Using 23.7 g of diethyl sulfate, the same operation as in Example 1 was carried out except that 20.4 g of cyclohexylpropyl ethyl ether was added.
g (yield 85%, boiling point 71 ° C./5 mmHg) was obtained.
IR（液膜,cm-1）:2974,2926,2860,1452,1383,1113 NMR（CDCl3，δ,TMS内部標準,ppm）:0.87（d,J＝7Hz,3
H）,0.9-2.0（m,12H）,1.20（t,J＝7Hz,3H）,3.22（d,J
＝7Hz,1H）,3.37（d,J＝7Hz,1H）,3.43（q,J＝7Hz,2H） 実施例３ ２−シクロヘキシルプロピルアリルエーテル（本発明化
合物３）の合成： 300ml丸底フラスコに窒素気流下、水素化ナトリウム6
0wt％鉱油分散品6.2g及びトルエン50mlを仕込み、100℃
に加熱した。ここに２−シクロヘキシルプロパノール20
gとトルエン20mlの混合物をゆっくり滴下した。100℃で
１時間撹拌し、水素の発生が止まったことを確認してか
ら60℃に冷却し、次いで臭化アリル22.2gを加えてさら
に60℃で20時間撹拌した。得られた反応混合物を水洗
後、減圧で蒸留したところ２−シクロヘキシルプロピル
アリルエーテル19.0g（収率74％、沸点92℃/5mmHg）が
得られた。IR (liquid film, cm -1 ): 2974, 2926, 2860, 1452, 1383, 1113 NMR (CDCl 3 , δ, TMS internal standard, ppm): 0.87 (d, J = 7Hz, 3
H), 0.9-2.0 (m, 12H), 1.20 (t, J = 7Hz, 3H), 3.22 (d, J
= 7Hz, 1H), 3.37 (d, J = 7Hz, 1H), 3.43 (q, J = 7Hz, 2H) Example 3 Synthesis of 2-cyclohexylpropyl allyl ether (inventive compound 3): in a 300 ml round bottom flask Sodium hydride 6 under nitrogen stream
Charge 6.2 g of 0 wt% mineral oil dispersion and 50 ml of toluene at 100 ° C.
Heated. 2-cyclohexyl propanol 20 here
A mixture of g and 20 ml of toluene was slowly added dropwise. After stirring at 100 ° C. for 1 hour and confirming that the generation of hydrogen had stopped, the mixture was cooled to 60 ° C. Then, 22.2 g of allyl bromide was added and further stirred at 60 ° C. for 20 hours. The obtained reaction mixture was washed with water and distilled under reduced pressure to obtain 19.0 g of 2-cyclohexylpropyl allyl ether (yield 74%, boiling point 92 ° C / 5 mmHg).
IR（液膜,cm-1）:3088,2926,2854,1650,1452,1104,921 NMR（CDCl3，δ,TMS内部標準,ppm）:0.88（d,J＝7Hz,3
H）,0.9-2.0（m,12H）,3.26（d,J＝7Hz,1H）,3.33（d,J
＝7Hz,1H）,3.93（dd,J＝2Hz,7Hz,2H）,5.03（m,1H）,
5.1-5.4（m,1H）,5.7-6.2（m,1H） GC-MS（Ｍ+）:182 実施例４ ２−シクロヘキシルプロピルベンジルエーテル（本発明
化合物４）の合成： 実施例３において用いた臭化アリルの替りに塩化ベン
ジル23.2gを用い、その他は実施例３と同様な操作を行
い、２−シクロヘキシルプロピルベンジルエーテル25.5
g（収率78％、沸点150-155℃/5mmHg）を得た。IR (liquid film, cm -1 ): 3088,2926,2854,1650,1452,1104,921 NMR (CDCl 3 , δ, TMS internal standard, ppm): 0.88 (d, J = 7Hz, 3
H), 0.9-2.0 (m, 12H), 3.26 (d, J = 7Hz, 1H), 3.33 (d, J
= 7Hz, 1H), 3.93 (dd, J = 2Hz, 7Hz, 2H), 5.03 (m, 1H),
5.1-5.4 (m, 1H), 5.7-6.2 (m, 1H) GC-MS (M + ): 182 Example 4 Synthesis of 2-cyclohexylpropylbenzyl ether (inventive compound 4): Used in Example 3. 23.2 g of benzyl chloride was used instead of allyl bromide, and otherwise the same operation as in Example 3 was carried out to give 2-cyclohexylpropyl benzyl ether 25.5 g.
g (yield 78%, boiling point 150-155 ° C./5 mmHg) was obtained.
IR（液膜,cm-1）:3068,3032,2928,2852,1454,1100 NMR（CDCl3，δ,TMS内部標準,ppm）:0.90（d,J＝7Hz,3
H）,0.9-2.0（m,12H）,3.33（d,J＝7Hz,1H）,3.40（d,J
＝7Hz,1H）,4.45（s,2H）,7.30（s,5H） GC-MS（Ｍ+）:231 実施例５ ２−シクロヘキシルプロピルプロピオネート（本発明化
合物５）の合成： 300ml丸底フラスコに２−シクロヘキシルプロパノー
ル30g、ピリジン16.7g及びヘキサン150mlを仕込んだ。
この混合物を０℃に冷却し、塩化プロピオニル19.6gを
ゆっくり滴下し、更に０℃にて５時間撹拌した。反応混
合物から生成した沈殿をろ過した後、有機層を水洗し、
減圧にて蒸留を行ったところ２−シクロヘキシルプロピ
ルプロピオネート37.6g（収率90％、沸点100℃/4.5mmH
g）が得られた。IR (liquid film, cm -1 ): 3068,3032,2928,2852,1454,1100 NMR (CDCl 3 , δ, TMS internal standard, ppm): 0.90 (d, J = 7Hz, 3
H), 0.9-2.0 (m, 12H), 3.33 (d, J = 7Hz, 1H), 3.40 (d, J
= 7Hz, 1H), 4.45 (s, 2H), 7.30 (s, 5H) GC-MS (M + ): 231 Example 5 Synthesis of 2-cyclohexylpropyl propionate (inventive compound 5): 300 ml round bottom A flask was charged with 30 g of 2-cyclohexylpropanol, 16.7 g of pyridine and 150 ml of hexane.
This mixture was cooled to 0 ° C., 19.6 g of propionyl chloride was slowly added dropwise, and the mixture was further stirred at 0 ° C. for 5 hours. After filtering the precipitate generated from the reaction mixture, the organic layer was washed with water,
Distillation under reduced pressure gave 2-cyclohexylpropyl propionate 37.6 g (yield 90%, boiling point 100 ° C / 4.5 mmH
g) was obtained.
IR（液膜,cm-1）:2926,2860,1746,1452,1353,1191,108
3,1017 NMR（CDCl3，δ,TMS内部標準,ppm）:0.90（d,J＝7Hz,3
H）,0.9-2.0（m,12H）,1.17（t,J＝7Hz,3H）,2.33（q,J
＝7Hz,2H）,3.93（d,J＝7Hz,1H）,4.00（d,J＝7Hz,1H） 実施例６ ２−シクロヘキシルプロピルイソブチレート（本発明化
合物６）の合成： 実施例５において用いた塩化プロピオニルの替りに塩
化イソブチル22.6gを用い、その他は実施例５と同様な
操作を行い２−シクロヘキシルプロピルイソブチレート
41.6g（収率93％、沸点113℃/5mmHg）を得た。IR (liquid film, cm -1 ): 2926,2860,1746,1452,1353,1191,108
3,1017 NMR (CDCl 3 , δ, TMS internal standard, ppm): 0.90 (d, J = 7Hz, 3
H), 0.9-2.0 (m, 12H), 1.17 (t, J = 7Hz, 3H), 2.33 (q, J
= 7Hz, 2H), 3.93 (d, J = 7Hz, 1H), 4.00 (d, J = 7Hz, 1H) Example 6 Synthesis of 2-cyclohexylpropylisobutyrate (inventive compound 6): In Example 5 22.6 g of isobutyl chloride was used in place of the propionyl chloride used, and the same operation as in Example 5 was repeated except that 2-cyclohexylpropyl isobutyrate was used.
41.6 g (yield 93%, boiling point 113 ° C./5 mmHg) were obtained.
IR（液膜,cm-1）:2976,2928,2856,1738,1194,1158 NMR（CDCl3，δ,TMS内部標準,ppm）:0.89（d,J＝7Hz,3
H）,1.17（d,J＝7Hz,6H）,0.9-1.9（m,12H）,2.56（m,1
H）,3.93（d,J＝7Hz,1H）,4.01（d,J＝7Hz,1H） GC-MS（Ｍ+）:212 実施例７ ２−シクロヘキシルプロピル炭酸エチル（本発明化合物
７）の合成： 実施例５において用いた塩化プロピオニルの替りにク
ロロ炭酸エチル23.0gを用い、その他は実施例５と同様
な操作を行い２−シクロヘキシルプロピル炭酸エチル3
7.9g（収率84％、沸点116℃/5mmHg）を得た。IR (liquid film, cm -1 ): 2976,2928,2856,1738,1194,1158 NMR (CDCl 3 , δ, TMS internal standard, ppm): 0.89 (d, J = 7Hz, 3
H), 1.17 (d, J = 7Hz, 6H), 0.9-1.9 (m, 12H), 2.56 (m, 1
H), 3.93 (d, J = 7Hz, 1H), 4.01 (d, J = 7Hz, 1H) GC-MS (M + ): 212 Example 7 Synthesis of 2-cyclohexylpropyl ethyl carbonate (Compound 7 of the present invention) : 23.0 g of ethyl chlorocarbonate was used in place of the propionyl chloride used in Example 5, and the same operation as in Example 5 was carried out otherwise, and 2-cyclohexylpropyl ethyl carbonate 3
7.9 g (84% yield, boiling point 116 ° C / 5 mmHg) were obtained.
IR（液膜,cm-1）:2926,2860,1746,1452,1404,1374,125
4,1011,792 NMR（CDCl3，δ,TMS内部標準,ppm）:0.90（d,J＝7Hz,3
H）,0.9-2.0（m,12H）,1.33（t,J＝7Hz,3H）,4.00（d,J
＝7Hz,1H）,4.03（d,J＝7Hz,1H）,4.18（q,J＝7Hz,2H） 実施例８ ラベンダー調調合香料： ユーカリプトール 50（重量部） ボルネオール 20 カンファー 30 ジメトール1) 10 テトラヒドロリナロール 40 リナロール 300 リナリルアセテート 300 ターピニルアセテート 100 メチルアミルケトン 10 チンチロール2) ５ ゲラニルアセテート 20 クマリン 10 サンダルマイソールコア3) ５ 900 上記調合香料900重量部に２−シクロヘキシルプロピ
ルメチルエーテル（本発明化合物１）を100重量部加え
ることにより、よりフレッシュでナチュラル感の向上し
たラベンダー調調合香料が得られた。IR (liquid film, cm -1 ): 2926,2860,1746,1452,1404,1374,125
4,1011,792 NMR (CDCl 3 , δ, TMS internal standard, ppm): 0.90 (d, J = 7Hz, 3
H), 0.9-2.0 (m, 12H), 1.33 (t, J = 7Hz, 3H), 4.00 (d, J
= 7Hz, 1H), 4.03 (d, J = 7Hz, 1H), 4.18 (q, J = 7Hz, 2H ) 10 tetrahydrolinalool 40 linalool 300 linalyl acetate 300 terpinyl acetate 100 methyl amyl ketone 10 chinchylol 2) 5 geranyl acetate 20 coumarin 10 sandal mysole core 3) 5 900 By adding 100 parts by weight of the compound 1), a lavender-like mixed fragrance having a fresher and improved natural feeling was obtained.
１） ジメトール：ジボダン社スペシャリティケミカル 2,6−ジメチル−ヘプタン−２−オール ２） チンチロール：花王スペシャリティケミカル １−アリル−2,2,7,7−テトラメチルシクロヘプタン
−１−オール ３） サンダルマイソールコア：花王株式会社 ２−メチル−４−（2,2,3−トリメチル−３−シクロ
ペンテン−１−イル）−２−ブテン−１−オール 実施例９ ローズ調調合香料： β−ダマスコン ５（重量部） （10％ジエチルフタレート溶液） ローズオキシド ５ フェニルアセトアルデヒドジメチルセタール10 ｌ−メントン ５ ノナナール（10％ジエチルフタレート溶液）５ 10−ウンデセナール ５ リナロール 20 シトロネリルフォーメート 10 ゲラニルアセテート 50 ジメチルベンジルカルビニルアセテート 50 ゲラニオール 200 シトロネロール 350 フェニルエチルアルコール 130 ローズフェノン 30 フェニルエチルフェニルアセテート 50 オイゲノール ５ シンナミックアルコール 20 950 上記調合香料950重量部に２−シクロヘキシルプロピ
ルイソブチレート（本発明化合物６）50重量部を加える
ことによりトップにカモミル的なフルーティな甘さの付
与されたローズ調調合香料が得られた。1) Dimethol: Givaudan Specialty Chemicals 2,6-Dimethyl-heptan-2-ol 2) Chinchylol: Kao Specialty Chemicals 1-allyl-2,2,7,7-tetramethylcycloheptane-1-ol 3) Sandal mysole Core: Kao Co., Ltd. 2-Methyl-4- (2,2,3-trimethyl-3-cyclopenten-1-yl) -2-buten-1-ol Example 9 Rose-like compounded fragrance: β-Damascon 5 (weight Part) (10% diethyl phthalate solution) Rose oxide 5 Phenylacetaldehyde dimethyl cetal 10 l-Mentone 5 Nonanal (10% diethyl phthalate solution) 5 10-Undecenal 5 Linalool 20 Citronellyl formate 10 Geranyl acetate 50 Dimethylbenzylcarbinyl acetate 50 Geraniol 200 Citronello 350 phenylethyl alcohol 130 Rose phenone 30 phenylethyl phenylacetate 50 Eugenol 5 cinnamic alcohol 20 950 above mixed perfumes 950 parts by weight of 2-cyclohexyl-propyl isobutyrate (present compound 6) chamomile on top by adding 50 parts by weight A rose-like compounded perfume having a typical fruity sweetness was obtained.
───────────────────────────────────────────────────── フロントページの続き (51)Int.Cl.6 識別記号 庁内整理番号 ＦＩ 技術表示箇所 Ｃ０７Ｃ 69/24 Ｃ０７Ｃ 69/24 Ｃ１１Ｂ 9/00 Ｃ１１Ｂ 9/00 Ｇ ─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. 6 Identification code Internal reference number FI Technical display location C07C 69/24 C07C 69/24 C11B 9/00 C11B 9/00 G
Claims (2)
ンジル基又は−COR′（Ｒ′は炭素数２〜３のアルキル
基又はエトキシ基を示す）を示す〕 で表される２−シクロヘキシルプロパノール誘導体。1. The following general formula (I) [In the formula, R represents an alkyl group having 1 to 3 carbon atoms, an allyl group, a benzyl group or -COR '(R' represents an alkyl group having 2 to 3 carbon atoms or an ethoxy group)] -Cyclohexyl propanol derivative.
ノール誘導体を含有することを特徴とする香料組成物。2. A fragrance composition comprising the 2-cyclohexyl propanol derivative according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1202029A JP2686828B2 (en) | 1989-08-03 | 1989-08-03 | 2-Cyclohexylpropanol derivative and fragrance composition containing the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1202029A JP2686828B2 (en) | 1989-08-03 | 1989-08-03 | 2-Cyclohexylpropanol derivative and fragrance composition containing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH0366637A JPH0366637A (en) | 1991-03-22 |
| JP2686828B2 true JP2686828B2 (en) | 1997-12-08 |
Family
ID=16450745
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1202029A Expired - Fee Related JP2686828B2 (en) | 1989-08-03 | 1989-08-03 | 2-Cyclohexylpropanol derivative and fragrance composition containing the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP2686828B2 (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6172016B1 (en) * | 1999-07-12 | 2001-01-09 | Bush Boakes Allen Inc. | Fragrance materials |
| US6187727B1 (en) * | 1999-07-12 | 2001-02-13 | Bush Boake Allen, Inc. | Fragrance materials |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3323330A1 (en) | 1982-07-01 | 1984-01-05 | Basf Ag, 6700 Ludwigshafen | O-Substituted 2-hydroxypropanals and their preparation, as well as odoriferous compositions containing this compound |
-
1989
- 1989-08-03 JP JP1202029A patent/JP2686828B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3323330A1 (en) | 1982-07-01 | 1984-01-05 | Basf Ag, 6700 Ludwigshafen | O-Substituted 2-hydroxypropanals and their preparation, as well as odoriferous compositions containing this compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0366637A (en) | 1991-03-22 |
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