JP4473673B2 - Novel pyran derivatives and perfume compositions - Google Patents
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Description
本発明は、ハーバル系、グリーン系あるいはフローラル系の香気を有し、石鹸、シャンプーリンス、洗剤、化粧品、芳香剤などの賦香成分として有用な新規ピラン誘導体及びそれを含有する香料組成物に関する。 The present invention relates to a novel pyran derivative having a herbal, green or floral fragrance, and useful as a fragrance component for soaps, champulins, detergents, cosmetics, fragrances and the like, and a fragrance composition containing the same.
従来、ピラン誘導体にはいくつかの有用な香料化合物が知られている。例えば、ゼラニウム油などに含まれている、4−メチル−2−(2−メチル−1−プロペニル)−テトラヒドロピラン(慣用名;ローズオキシド)は、グリーン、フローラル香を有することがよく知られている。また、特許文献1には、テトラヒドロ−4−メチル−2−フェニル−2H−ピランが、特許文献2及び特許文献3の各々には、2−シクロヘキセニル−5,6−ジヒドロ−4−メチル−2H−ピランが香料化合物として用いられることが記載されている。
近年、嗜好の多様化に伴い、多様な香気を有する種々の香料が望まれている。しかしながら、香料化合物の香気は構造の僅かな相違により大きく異なるのが一般的であり、そのため多様な香気を有する新規香料を得るためには、種々の構造の化合物を合成しその香気を検討することが必要であり、重要なことであった。
Conventionally, several useful perfume compounds are known for pyran derivatives. For example, 4-methyl-2- (2-methyl-1-propenyl) -tetrahydropyran (common name; rose oxide) contained in geranium oil and the like is well known to have a green and floral fragrance. Yes. Patent Document 1 discloses tetrahydro-4-methyl-2-phenyl-2H-pyran, and Patent Document 2 and Patent Document 3 each include 2-cyclohexenyl-5,6-dihydro-4-methyl-. It is described that 2H-pyran is used as a perfume compound.
In recent years, with the diversification of tastes, various fragrances having various fragrances are desired. However, the fragrance of a fragrance compound is generally greatly different due to slight differences in structure. Therefore, in order to obtain a new fragrance having various fragrances, compounds of various structures are synthesized and the fragrance is examined. It was necessary and important.
本発明は、ハーバル系、グリーン系、フローラル系の香気を有する新規な香料化合物、及びこれを含有する香料組成物を提供することを目的とする。 An object of this invention is to provide the novel fragrance | flavor compound which has a herbal type | system | group, a green type | system | group, and a floral fragrance | flavor, and the fragrance | flavor composition containing this.
本発明者らは、トリメチルフェニル基を有する特定の新規ピラン誘導体を合成し、その香気について検討した結果、ハーバル系、グリーン系、フローラル系の香気を有し、トイレタリー製品などの賦香に有用なピラン誘導体を見いだした。
すなわち、本発明は、下記一般式(I)、(II)または(III)で表されるピラン誘導体(以下、それぞれピラン誘導体(I)、ピラン誘導体(II)、ピラン誘導体(III)と略記することがあり、これらをまとめて本発明のピラン誘導体ということがある)、およびこれを含有する香料組成物を提供する。
As a result of synthesizing a specific novel pyran derivative having a trimethylphenyl group and examining the aroma, the present inventors have herbal, green, and floral aromas, and are useful for aromatizing toiletries and the like. A pyran derivative was found.
That is, the present invention is abbreviated as a pyran derivative represented by the following general formula (I), (II) or (III) (hereinafter referred to as a pyran derivative (I), a pyran derivative (II) and a pyran derivative (III), respectively). These may be collectively referred to as the pyran derivative of the present invention), and a perfume composition containing the same is provided.
本発明によれば、ハーバル系、グリーン系又はフローラル系の香気を有する新規な香料化合物、及びこれを含有する香料組成物を提供することができる。 ADVANTAGE OF THE INVENTION According to this invention, the novel fragrance | flavor compound which has a herbal type | system | group, a green type | system | group or a floral fragrance | flavor, and the fragrance | flavor composition containing this can be provided.
本発明のピラン誘導体の製造方法を以下に示す。
ピラン誘導体(I)及びピラン誘導体(III)は、いずれも、例えば、一般式(IV)
The manufacturing method of the pyran derivative of this invention is shown below.
The pyran derivative (I) and the pyran derivative (III) are both represented by, for example, the general formula (IV)
で表わされる化合物とを酸触媒の存在下で反応させることにより製造することができる。具体的には、以下の反応式で示す方法によって製造することができる。
In the presence of an acid catalyst. Specifically, it can be produced by the method shown by the following reaction formula.
すなわち、上記反応式においては、トリメチルベンズアルデヒド(IV)に、酸触媒存在下で、アルコール(V)を反応させることにより、ピラン誘導体(I)とピラン誘導体(III)をこれらの混合物として得ることができる。
上記反応において、トリメチルベンズアルデヒド(IV)とアルコール(V)の仕込み比率は、収率を向上させる観点から、トリメチルベンズアルデヒド(IV)を過剰に用いることが好ましく、具体的には、トリメチルベンズアルデヒド(IV)/アルコール(V)モル比で1〜10の範囲内であることが好ましく、1〜3.5の範囲であることが更に好ましい。
That is, in the above reaction formula, pyran derivative (I) and pyran derivative (III) can be obtained as a mixture of these by reacting trimethylbenzaldehyde (IV) with alcohol (V) in the presence of an acid catalyst. it can.
In the above reaction, the charging ratio of trimethylbenzaldehyde (IV) and alcohol (V) is preferably an excess of trimethylbenzaldehyde (IV) from the viewpoint of improving the yield, specifically, trimethylbenzaldehyde (IV). The molar ratio of alcohol / alcohol (V) is preferably in the range of 1 to 10, and more preferably in the range of 1 to 3.5.
上記反応に用いられる一般式(V)で表わされる化合物としては、R1が水素原子又はメチル基であるアルコール類が挙げられる。また、酸触媒としては、例えば、メタンスルホン酸、パラトルエンスルホン酸、硫酸、塩酸等が挙げられ、これらのうち、メタンスルホン酸、パラトルエンスルホン酸を好ましく用いることができる。上記酸触媒の添加量としては、トリメチルベンズアルデヒド(IV)1モルに対し0.05〜5モル%であることが好ましく、0.1〜1モル%であることが更に好ましい。
上記反応は、無溶媒で行うことも可能であるが、トルエン、シクロヘキサン、ジクロロメタン等の溶媒を用いても行うこともできる。本発明においては、生産性を向上させる観点から、無溶媒で行うことが好ましい。
反応速度を高める観点から、上記反応における反応温度は40℃以上であることが好ましく、一方、副反応を抑制する観点から、120℃以下であることが好ましい。
Examples of the compound represented by the general formula (V) used in the above reaction include alcohols in which R 1 is a hydrogen atom or a methyl group. Examples of the acid catalyst include methanesulfonic acid, paratoluenesulfonic acid, sulfuric acid, hydrochloric acid, and the like. Among these, methanesulfonic acid and paratoluenesulfonic acid can be preferably used. The addition amount of the acid catalyst is preferably 0.05 to 5 mol%, more preferably 0.1 to 1 mol%, based on 1 mol of trimethylbenzaldehyde (IV).
The above reaction can be carried out without a solvent, but can also be carried out using a solvent such as toluene, cyclohexane, or dichloromethane. In this invention, it is preferable to carry out without a solvent from a viewpoint of improving productivity.
From the viewpoint of increasing the reaction rate, the reaction temperature in the above reaction is preferably 40 ° C. or higher, and from the viewpoint of suppressing side reactions, it is preferably 120 ° C. or lower.
上記の反応により得られたピラン誘導体(I)とピラン誘導体(III)の混合物は、混合物のままの状態でも香料として有用であるが、カラムクロマト法などの精製手段により分離精製することで、ピラン誘導体(I)及びピラン誘導体(III)をそれぞれ単独で香料として得ることができる。
ピラン誘導体(II)は、下記式に示すように、上記ピラン誘導体(I)を、パラジウム/カーボンなどの遷移金属触媒存在下で水素添加することでヒドロキシピラン誘導体として製造することができる。上記水素添加は、公知の方法を用いて行うことができる。
The mixture of the pyran derivative (I) and the pyran derivative (III) obtained by the above reaction is useful as a fragrance even in the state of the mixture, but can be separated and purified by a purification means such as column chromatography. The derivative (I) and the pyran derivative (III) can each be obtained as a fragrance.
As shown in the following formula, the pyran derivative (II) can be produced as a hydroxypyran derivative by hydrogenating the pyran derivative (I) in the presence of a transition metal catalyst such as palladium / carbon. The hydrogenation can be performed using a known method.
以上のようにして得られるピラン誘導体(I)とピラン誘導体(II)は、いずれもハーバル、グリーン、ゼラニウム系の香気を有し、また、ピラン誘導体(III)はミューゲ系のフローラル香気を有する。これらの化合物は、単独で、あるいは他の成分と組み合わせて石鹸、シャンプーリンス、洗剤、化粧品、芳香剤などの賦香成分として使用することができる。 The pyran derivative (I) and the pyran derivative (II) obtained as described above all have herbal, green and geranium fragrances, and the pyran derivative (III) has a Mugue floral fragrance. These compounds can be used alone or in combination with other ingredients as perfuming ingredients such as soaps, champulences, detergents, cosmetics, and fragrances.
本発明の香料組成物は、所望組成の調合香料に、上記ピラン誘導体(I)、(II)及び(III)の少なくとも一種を配合して得ることができる。該香料組成物中におけるピラン誘導体(I)、(II)または(III)の配合量は、調合香料の種類、目的とする香気の種類および香気の強さにより異なるが、0.1〜90質量%が好ましく、特に0.5〜50質量%であることが好ましい。 The fragrance composition of the present invention can be obtained by blending at least one of the above pyran derivatives (I), (II) and (III) with a blended fragrance having a desired composition. The amount of the pyran derivative (I), (II) or (III) in the fragrance composition varies depending on the type of the blended fragrance, the type of the target fragrance, and the strength of the fragrance, but it is 0.1 to 90 mass. % Is preferable, and 0.5 to 50% by mass is particularly preferable.
以下、実施例により本発明をさらに具体的に説明する。
実施例1
下記4−メチル−2−(2,4,6−トリメチルフェニル)ジヒドロピラン誘導体 (本発明化合物1)および4−メチル−2−(2,4,6−トリメチルフェニル)テトラヒドロピラン−4−オール (本発明化合物3) の合成
Hereinafter, the present invention will be described more specifically with reference to examples.
Example 1
The following 4-methyl-2- (2,4,6-trimethylphenyl) dihydropyran derivative (present compound 1) and 4-methyl-2- (2,4,6-trimethylphenyl) tetrahydropyran-4-ol ( Synthesis of the present compound 3)
2,4,6−トリメチルベンズアルデヒド (148.2g, 1.0mol ) にパラトルエンスルホン酸 (0.19g, 0.001mol) を加え、100℃でイソプレノール (94.7g,1.1mol) を2時間かけて滴下した。100℃で3時間攪拌し、室温まで戻した後、水(50g )、飽和塩化ナトリウム水溶液 (50g)、0.5mol/l炭酸ナトリウム水溶液 (4.5g) 、ジエチルエーテル (50g) を加え中和し、有機層を減圧濃縮した。得られた黒色油状物を減圧蒸留することにより、ジヒドロピラン誘導体(本発明化合物1)と4−メチル−2−(2,4,6−トリメチルフェニル)−4−オール(本発明化合物3)の混合物を得た。反応収率はそれぞれ、38%、32%であった。
蒸留留分を中圧カラム液体クロマトグラフィー (溶媒:ヘキサン/酢酸エチル=39/1) により精製して下記特性を有するジヒドロピラン誘導体 (本発明化合物1)(純度 ; 99.6%) および4−メチル−2−(2,4,6−トリメチルフェニル)テトラヒドロピラン−4−オール(本発明化合物3)(純度 ; 99.7%)を得た。
得られたジヒドロピラン誘導体(本発明化合物1)は、ハーバル、ゼラニウム、グリーン系で、コスタス−レザー様の香気を有していた。また、4−メチル−2−(2,4,6−トリメチルフェニル)テトラヒドロピラン−4−オール(本発明化合物3)は、甘さのあるミューゲ様の香気を有していた。
Paratoluenesulfonic acid (0.19 g, 0.001 mol) was added to 2,4,6-trimethylbenzaldehyde (148.2 g, 1.0 mol), and isoprenol (94.7 g, 1.1 mol) was added at 100 ° C. for 2 hours. It was dripped over. After stirring at 100 ° C. for 3 hours and returning to room temperature, water (50 g), saturated aqueous sodium chloride solution (50 g), 0.5 mol / l aqueous sodium carbonate solution (4.5 g) and diethyl ether (50 g) were added to neutralize. The organic layer was concentrated under reduced pressure. The black oil obtained was distilled under reduced pressure to obtain a dihydropyran derivative (present compound 1) and 4-methyl-2- (2,4,6-trimethylphenyl) -4-ol (present compound 3). A mixture was obtained. The reaction yields were 38% and 32%, respectively.
The distillate fraction was purified by medium pressure column liquid chromatography (solvent: hexane / ethyl acetate = 39/1) to give a dihydropyran derivative (present compound 1) having the following characteristics (purity: 99.6%) and 4- Methyl-2- (2,4,6-trimethylphenyl) tetrahydropyran-4-ol (present compound 3) (purity: 99.7%) was obtained.
The obtained dihydropyran derivative (present compound 1) was herbal, geranium, green, and had a Costas-leather-like fragrance. Further, 4-methyl-2- (2,4,6-trimethylphenyl) tetrahydropyran-4-ol (present compound 3) had a sweet Mugue-like fragrance.
ジヒドロピラン誘導体(本発明化合物1)の帰属
・4-メチル-2-(2,4,6-トリメチルフェニル)-3,6-ジヒドロ-2H-ピラン(1a)、
4-メチル-6-(2,4,6-トリメチルフェニル)-3,6-ジヒドロ-2H-ピラン(1b)及び4-メチレン-2-(2,4,6-トリメチルフェニル)テトラヒドロピラン(1c)の混合物
・1H−NMR(CDCl3): 異性体が存在するために帰属はできなかった。
・13C−NMR (CDCl3) δ=145.3(-C=CH-), 136.8, 136.3, 136.1, 135.1, 134.8, 132.4, 130.3, 130.2(aromC), 120.5(-C=CH-), 108.9(-CH2-), 79.0, 73.9(aromC-CH-), 69.7, 66.6(-O-CH2-), 39.4, 35.5, 34.5(-CH2-), 23.2(-CH3), 21.1, 21.0(aromC-CH3)
Assignment of dihydropyran derivative (compound 1 of the present invention) 4-methyl-2- (2,4,6-trimethylphenyl) -3,6-dihydro-2H-pyran (1a)
4-methyl-6- (2,4,6-trimethylphenyl) -3,6-dihydro-2H-pyran (1b) and 4-methylene-2- (2,4,6-trimethylphenyl) tetrahydropyran (1c) ) 1 H-NMR (CDCl 3 ): Assignment was not possible due to the presence of isomers.
13 C-NMR (CDCl 3 ) δ = 145.3 (-C = CH-), 136.8, 136.3, 136.1, 135.1, 134.8, 132.4, 130.3, 130.2 (aromC), 120.5 (-C = CH-), 108.9 ( -CH 2- ), 79.0, 73.9 (aromC-CH-), 69.7, 66.6 (-O-CH 2- ), 39.4, 35.5, 34.5 (-CH 2- ), 23.2 (-CH 3 ), 21.1, 21.0 (aromC-CH 3 )
4-メチル-2-(2,4,6-トリメチルフェニル)テトラヒドロピラン-4-オール(本発明化合物3)の帰属
・1H−NMR(CDCl3) δ=6.80(2H, s, aromH), 4.74-4.71(1H, dd, Ar-CH-), 4.15-4.10, 3.59-3.52,(2H, ddd, td, -O-CH2-), 2.38(6H, s, CH3-Ar-), 2.23(3H, s, CH3-Ar-)・,2.05-1.99, 1.91-1.83, 1.70-1.61(4H, t, dd, m, -CH2-), 1.45(3H, s, -CH3)
・13C−NMR (CDCl3) δ=136.8, 135.9, 134.4, 130.3(aromC), 75.7(Ar-C-), 69.4(-C-OH), 66.3(-O-CH2-), 44.4(-CH2-), 40.5(-CH2-), 25.3(-CH3), 21.0, 20.9(aromC-CH3)
実施例2
下記4−メチル−2−(2,4,6−トリメチルフェニル)テトラヒドロピラン(本発明化合物2)の合成 Assignment of 4-methyl-2- (2,4,6-trimethylphenyl) tetrahydropyran-4-ol (present compound 3) 1 H-NMR (CDCl 3 ) δ = 6.80 (2H, s, aromH), 4.74-4.71 (1H, dd, Ar-CH-), 4.15-4.10, 3.59-3.52, (2H, ddd, td, -O-CH 2- ), 2.38 (6H, s, CH 3 -Ar-), 2.23 (3H, s, CH 3 -Ar-) ・, 2.05-1.99, 1.91-1.83, 1.70-1.61 (4H, t, dd, m, -CH 2- ), 1.45 (3H, s, -CH 3 )
13 C-NMR (CDCl 3 ) δ = 136.8, 135.9, 134.4, 130.3 (aromC), 75.7 (Ar-C-), 69.4 (-C-OH), 66.3 (-O-CH 2- ), 44.4 ( -CH 2- ), 40.5 (-CH 2- ), 25.3 (-CH 3 ), 21.0, 20.9 (aromC-CH 3 )
Example 2
Synthesis of the following 4-methyl-2- (2,4,6-trimethylphenyl) tetrahydropyran (present compound 2)
実施例1で合成した、ジヒドロピラン誘導体(本発明化合物1)(7.03g,32.5mmol) をイソプロパノール (70g) に溶かし、この中に5%Pd/C (H2O: 54.29%) (0.07g) を加え、0.3MPaの水素加圧下、60℃で5時間激しく撹拌した。反応液を濾過した後、減圧濃縮した。反応収率は75%であった。得られた無色油状物を中圧カラム液体クロマトグラフィー ( 溶媒:ヘキサン/酢酸エチル=39/1) により精製して下記特性を有する4−メチル−2−(2,4,6−トリメチルフェニル)テトラヒドロピラン(本発明化合物2)を3.3g(純度 ; 99.6%) 得た。得られた化合物2は、ハーバル、グリーン、ゼラニウム様の香気を有していた。 The dihydropyran derivative (Compound 1 of the present invention) (7.03 g, 32.5 mmol) synthesized in Example 1 was dissolved in isopropanol (70 g), and 5% Pd / C (H 2 O: 54.29%) was dissolved therein. (0.07 g) was added, and the mixture was vigorously stirred at 60 ° C. for 5 hours under a hydrogen pressure of 0.3 MPa. The reaction mixture was filtered and concentrated under reduced pressure. The reaction yield was 75%. The obtained colorless oil was purified by medium pressure column liquid chromatography (solvent: hexane / ethyl acetate = 39/1) to give 4-methyl-2- (2,4,6-trimethylphenyl) tetrahydro having the following characteristics. 3.3 g (purity: 99.6%) of pyran (present compound 2) was obtained. The obtained compound 2 had herbal, green, and geranium-like fragrances.
4-メチル-2-(2,4,6-トリメチルフェニル)テトラヒドロピラン(本発明化合物2)の帰属
・1H−NMR(CDCl3) δ=6.70(2H, s, aromH), 4.98-4.95, 4.70-4.66(1H, dd×2, Ar-CH-), 4.16-4.12, 3.94-3.90, 3.83-3.77, 3.55-3.49(2H, dd×2, td×2, -O-CH2-), 2.39(6H, s, CH3-Ar-), 2.23(3H, s, CH3-Ar-)・, 2.02-1.26(1H, m, -CH-, 4H, m, -CH2-), 1.24-1.23, 0.98-0.97(3H, d×2, -CH3)
・13C−NMR (CDCl3) δ=136.4, 135.9, 135.6, 130.2(aromC), 77.8, 72.3(Ar-C-), 68.9, 63.9(-O-CH2-), 38.6, 35.5(-CH2-), 34.8, 31.5(-CH2-), 31.4, 25.7(-C-CH3), 22.5, 17.5(-CH3), 21.1, 21.0(aromC-CH3)
Assignment of 4-methyl-2- (2,4,6-trimethylphenyl) tetrahydropyran (present compound 2) 1 H-NMR (CDCl 3 ) δ = 6.70 (2H, s, aromH), 4.98-4.95, 4.70-4.66 (1H, dd × 2, Ar-CH-), 4.16-4.12, 3.94-3.90, 3.83-3.77, 3.55-3.49 (2H, dd × 2, td × 2, -O-CH 2- ), 2.39 (6H, s, CH 3 -Ar-), 2.23 (3H, s, CH 3 -Ar-) ・, 2.02-1.26 (1H, m, -CH-, 4H, m, -CH 2- ), 1.24 -1.23, 0.98-0.97 (3H, d × 2, -CH 3 )
・13 C-NMR (CDCl 3 ) δ = 136.4, 135.9, 135.6, 130.2 (aromC), 77.8, 72.3 (Ar-C-), 68.9, 63.9 (-O-CH 2- ), 38.6, 35.5 (-CH 2- ), 34.8, 31.5 (-CH 2- ), 31.4, 25.7 (-C-CH 3 ), 22.5, 17.5 (-CH 3 ), 21.1, 21.0 (aromC-CH 3 )
実施例3
ローズ油タイプの香料 質量部
ゲラニオール 250
シトロネロール 200
ロジノール 100
フェニルエチルアルコール エクストラ 310
ネロール 30
ゼラニウムオイル アフリカ 10
900
上記ローズ油900質量部に、実施例2で得られた4−メチル−2−(2,4,6−トリメチルフェニル)テトラヒドロピラン(本発明化合物2)を100質量部加えることにより、フレッシュなハーバル、グリーン、ゼラニウム様の香気が強調された新しいローズ油が得られた。
Example 3
Rose oil type fragrance Mass parts Geraniol 250
Citronellol 200
Rosinol 100
Phenylethyl alcohol extra 310
Nellore 30
Geranium oil Africa 10
900
By adding 100 parts by mass of 4-methyl-2- (2,4,6-trimethylphenyl) tetrahydropyran (present compound 2) obtained in Example 2 to 900 parts by mass of the rose oil, a fresh herbal is obtained. A new rose oil with a green, geranium-like aroma was emphasized.
本発明のピラン誘導体は、ハーバル系、グリーン系、フローラル系の香気を有し、香料用賦香成分として有用であり、石鹸、シャンプーリンス、洗剤、化粧品、芳香剤等への賦香成分として用いることができる。
The pyran derivative of the present invention has herbal, green, and floral fragrances and is useful as a fragrance component for fragrances, and is used as a fragrance component for soaps, champulins, detergents, cosmetics, fragrances, and the like. be able to.
Claims (5)
で表されるピラン誘導体。 General formula (I)
A pyran derivative represented by:
で表されるピラン誘導体。 General formula (II)
A pyran derivative represented by:
で表されるピラン誘導体。 General formula (III)
A pyran derivative represented by:
で表わされる化合物とを酸触媒の存在下で反応させる、一般式(I)
で表わされるピラン誘導体及び一般式 (III)
で表わされるピラン誘導体の製造方法。 Formula (IV)
The compound represented by formula (I) is reacted in the presence of an acid catalyst.
A pyran derivative represented by the general formula (III)
The manufacturing method of the pyran derivative represented by these.
A fragrance composition containing at least one pyran derivative according to any one of claims 1 to 3.
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PL3131888T3 (en) * | 2014-04-14 | 2022-12-12 | Basf Se | Production of starting materials containing 2-substituted 4-hydroxy-4-methyl-tetrahydropyranes from 2-alkyl-4,4-dimethyl-1,3-dioxane |
CN109195959B (en) * | 2016-05-31 | 2023-08-18 | 巴斯夫欧洲公司 | Tetrahydropyranyl lower alkyl esters and preparation using ketene compounds |
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