JPH07268384A - Method for separating oily component - Google Patents
Method for separating oily componentInfo
- Publication number
- JPH07268384A JPH07268384A JP8718494A JP8718494A JPH07268384A JP H07268384 A JPH07268384 A JP H07268384A JP 8718494 A JP8718494 A JP 8718494A JP 8718494 A JP8718494 A JP 8718494A JP H07268384 A JPH07268384 A JP H07268384A
- Authority
- JP
- Japan
- Prior art keywords
- oil
- oily component
- mixture
- tree essential
- essential oil
- 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.)
- Granted
Links
Abstract
Description
【０００１】[0001]
【産業上の利用分野】本発明は、油状成分の分離方法並
びに該油状成分を有効成分とする殺ダニ剤もしくは抗菌
剤に関する。かつて林産資源の有効利用として、漆、精
油、樹脂、ろう、油脂、色素、タンニン、配糖体、アル
カロイド等の樹木が生理的に生産した成分を抽出分離
し、これらを活用していた。しかし、近年は石油化学合
成品に代替されるようになり、天然物由来のものは殆ど
利用されなくなった。しかし、最近では、人間に対する
作用が穏やかで安全であるということから、天然物志向
が急速に高まっている。本発明は、石油化学合成品に代
わり、天然物である樹木精油または樹木精油成分である
テルペン類混合物からの特定成分の効率的な抽出方法お
よび抽出された油状成分を有効成分とする殺ダニ剤、抗
菌剤に関するものである。BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a method for separating an oily component and an acaricide or antibacterial agent containing the oily component as an active ingredient. In the past, the effective utilization of forest resources was to extract and separate the physiologically produced components of trees such as lacquer, essential oils, resins, waxes, fats and oils, pigments, tannins, glycosides and alkaloids, and utilize them. However, in recent years, it has come to be replaced by petrochemical synthetic products, and those derived from natural products are hardly used. However, recently, the tendency toward natural products has rapidly increased due to its mild and safe action on humans. The present invention provides a method for efficiently extracting a specific component from a tree essential oil which is a natural product or a terpene mixture which is a tree essential oil component instead of a petrochemical synthetic product, and an acaricide containing the extracted oil component as an active ingredient. , Regarding antibacterial agents.
【０００２】[0002]
【従来の技術】樹木精油成分の分離は、通常、極性の違
いを利用した溶媒抽出を繰り返す方法、精密蒸留法、ま
たはそれらの複合法や各種クロマトグラフィー法によっ
て行われている。しかし、溶媒抽出法、精密蒸留法では
操作の繰り返しが多く工程が煩雑となり、消費エネルギ
ーも大きい。また、クロマトグラフィー法は分析が主目
的であり、工業的に多量に扱うのには適していない。と
ころで、樹木精油には殺ダニ作用、抗菌作用等を有する
成分が含まれているが、樹木精油自体の殺ダニ作用、抗
菌作用は非常に弱いため、各種クロマトグラフィー法に
より、これら殺ダニ作用、抗菌作用等を有する成分を単
離しなければならなかった。2. Description of the Related Art Separation of tree essential oil components is usually carried out by a method of repeating solvent extraction utilizing a difference in polarity, a precision distillation method, a combination method thereof or various chromatographic methods. However, in the solvent extraction method and the precision distillation method, the operation is often repeated, the process is complicated, and the energy consumption is large. The chromatographic method is mainly used for analysis and is not suitable for handling a large amount industrially. By the way, the tree essential oil contains components having an acaricidal action, an antibacterial action, etc., but the acaricidal action of the tree essential oil itself and the antibacterial action are very weak. It was necessary to isolate a component having an antibacterial action and the like.
【０００３】[0003]
【発明が解決しようとする課題】本発明は、溶解度の改
善を意図して開発されている置換型サイクロデキストリ
ンを利用して、多成分から成る樹木精油または樹木精油
成分であるテルペン類混合物から特定成分を高選択的に
抽出し、さらに元の樹木精油よりも殺ダニ作用、抗菌作
用の高い抽出油を得るという、新規で経済的な分離方法
を提供することを目的とするものである。DISCLOSURE OF THE INVENTION The present invention utilizes a substituted cyclodextrin, which has been developed for the purpose of improving the solubility, and identifies a tree essential oil or a mixture of terpenes which is a constituent of a tree essential oil. It is an object of the present invention to provide a novel and economical separation method in which components are highly selectively extracted and an extracted oil having a higher acaricidal action and antibacterial action than the original tree essential oil is obtained.
【０００４】[0004]
【課題を解決するための手段】すなわち本発明は、樹木
精油または樹木精油成分であるテルペン類混合物と、サ
イクロデキストリンの一つ以上の水酸基の水素が、グル
コシル基、マルトシル基、メチル基、エチル基、ヒドロ
キシメチル基、ヒドロキシエチル基およびヒドロキシプ
ロピル基のうちの少なくとも一つの基で置換された置換
型サイクロデキストリンとを接触させ、樹木精油または
樹木精油成分であるテルペン類混合物から抽出された油
状成分のサイクロデキストリン包接錯体を得、次いで該
包接錯体から油状成分を分離することを特徴とする油状
成分の分離方法並びにこの方法で得られた油状成分を有
効成分とする殺ダニ剤もしくは抗菌剤に関する。Means for Solving the Problems That is, the present invention provides a tree essential oil or a mixture of terpenes which is a tree essential oil component, and hydrogen of one or more hydroxyl groups of cyclodextrin, a glucosyl group, a maltosyl group, a methyl group, an ethyl group. , A hydroxymethyl group, a hydroxyethyl group and a hydroxypropyl group, and a substituted cyclodextrin substituted with at least one group are contacted to obtain an oily component extracted from a tree essential oil or a terpene mixture which is a tree essential oil component. The present invention relates to a method for separating an oily component, which comprises obtaining a cyclodextrin inclusion complex, and then separating an oily component from the inclusion complex, and an acaricide or antibacterial agent containing the oily component obtained by this method as an active ingredient. .
【０００５】以下に本発明を詳細に説明する。サイクロ
デキストリン（以下、ＣＤと略記することがある。）は
Ｄ−グルコース６〜８個が環状にα−１，４結合してで
きた物質で、Ｄ−グルコース６個のものはα−ＣＤ、７
個のものはβーＣＤ、８個のものはγ−ＣＤと呼ばれ、
これらはそれぞれの大きさを有する疎水性空洞内に様々
な有機化合物を取り込んで、包接錯体を形成することが
できる。その際に包接される有機化合物分子の大きさ、
形状等に応じて、包接錯体の形成しやすさに差異が生じ
るので、各ＣＤ固有の疎水性空洞の大きさおよびＣＤの
置換基と包接される有機化合物分子との相互作用を利用
して、様々な成分を有する樹木精油から特定成分を分離
することに応用できる。The present invention will be described in detail below. Cyclodextrin (hereinafter sometimes abbreviated as CD) is a substance formed by 6 to 8 D-glucose cyclically bound to α-1,4, and 6 D-glucose is α-CD, 7
The ones are called β-CD, the eight are called γ-CD,
These can incorporate various organic compounds into hydrophobic cavities of their respective sizes to form inclusion complexes. The size of the organic compound molecule to be included at that time,
Since the easiness of forming an inclusion complex varies depending on the shape, etc., the size of the hydrophobic cavity peculiar to each CD and the interaction between the substituent of CD and the organic compound molecule to be included in the inclusion are utilized. Therefore, it can be applied to separate a specific component from a tree essential oil having various components.
【０００６】本発明では、多成分からなる樹木精油また
は樹木精油成分であるテルペン類混合物からの特定成分
の分離用担体として、上記ＣＤの溶解度の改善を意図し
て製造されている置換型ＣＤを用いる。ここで用いる置
換型ＣＤとは、ＣＤの一つ以上の水酸基の水素が、グル
コシル基、マルトシル基、メチル基、エチル基、ヒドロ
キシメチル基、ヒドロキシエチル基およびヒドロキシプ
ロピル基のうちの少なくとも一つで置換された置換型Ｃ
Ｄを意味する。In the present invention, as a carrier for separating a specific component from a tree essential oil consisting of multiple components or a mixture of terpenes which is a component of a tree essential oil, a substitutional CD produced for the purpose of improving the solubility of the above CD is used. To use. The substituted CD used herein means that at least one hydrogen atom of the hydroxyl group of CD is at least one of glucosyl group, maltosyl group, methyl group, ethyl group, hydroxymethyl group, hydroxyethyl group and hydroxypropyl group. Substituted substitution type C
Means D.
【０００７】本発明においては、これらの置換型ＣＤを
水に溶解させ、これに樹木精油または樹木精油成分であ
るテルペン類混合物を加え、激しく攪拌または振盪す
る。置換型ＣＤの濃度は水に対し５〜１００重量％であ
るが、好ましくは１０〜３０重量％が適当である。In the present invention, these substitutional CDs are dissolved in water, and a tree essential oil or a mixture of terpenes which is a component of the tree essential oil is added and vigorously stirred or shaken. The concentration of substitutional CD is 5 to 100% by weight with respect to water, preferably 10 to 30% by weight.
【０００８】置換型ＣＤと樹木精油または樹木精油成分
であるテルペン類混合物の混合割合は、置換型ＣＤに対
する樹木精油または樹木精油成分であるテルペン類混合
物の重量比として通常0.０１〜５０倍、好ましくは0.１
〜１０倍になるようにする。両者の接触反応は、攪拌ま
たは振盪することにより行い、攪拌または振盪はできる
だけ激しく、通常は数秒から数時間、好ましくは１０〜
６０分間行う。なお、接触反応温度は、通常０〜４０
℃、好ましくは１５〜３０℃とする。この反応により、
樹木精油または樹木精油成分であるテルペン類混合物中
の特定成分を疎水性空洞に包接したＣＤ包接錯体が形成
される。The mixing ratio of the substitutional CD and the tree essential oil or the terpene mixture which is the tree essential oil component is usually 0.01 to 50 times as the weight ratio of the tree essential oil or the terpene mixture which is the tree essential oil component to the substitutional CD. Preferably 0.1
-10 times. The contact reaction between the two is performed by stirring or shaking, and stirring or shaking is as vigorous as possible, usually for several seconds to several hours, preferably 10 to
Do it for 60 minutes. The contact reaction temperature is usually 0 to 40.
C., preferably 15 to 30.degree. By this reaction,
A CD inclusion complex in which a specific component in a tree essential oil or a mixture of terpenes which is a tree essential oil component is included in a hydrophobic cavity is formed.
【０００９】攪拌または振盪による接触反応が終了した
後、適当な方法で油水分離を行う。例えば５〜１０分間
の遠心分離、濾過あるいは適当な塩を加える等の液−液
抽出において、油層と水層との分離性の向上に用いられ
る公知の手段を用いることができる。この操作により、
ＣＤに包接されなかった樹木精油または樹木精油成分で
あるテルペン類混合物と、その特定成分を包接したＣＤ
包接錯体とを分離できる。After completion of the contact reaction by stirring or shaking, oil-water separation is carried out by an appropriate method. For example, in liquid-liquid extraction such as centrifugation, filtration or addition of an appropriate salt for 5 to 10 minutes, known means used for improving the separability between the oil layer and the water layer can be used. By this operation,
Tree essential oil which is not included in CD or terpene mixture which is a component of tree essential oil, and CD in which the specific component is included
It can be separated from the inclusion complex.
【００１０】次に、水層に溶解しているＣＤ包接錯体か
ら樹木精油または樹木精油成分であるテルペン類混合物
より抽出された特定の油状成分を分離する。一般に、Ｃ
Ｄ包接錯体は６０〜７０℃以上の水溶液中で解離すると
いう公知の事実に基づき、水層を６０℃以上に加熱する
ことにより、包接された特定の油状成分を解離させ、水
層から分離させるか、あるいは置換型ＣＤに包接され難
く、水に溶解しにくい低沸点の揮発性有機溶媒、例えば
ジエチルエーテル、ｎ−ヘキサン等を用い、常温あるい
は６０〜７０℃の加温下で、特定の油状成分を有機層に
抽出する。この有機層から有機溶媒を揮発させると、目
的とする特定の油状成分が得られる。一方、水層は透明
な置換型ＣＤ水溶液となる。Next, a specific oily component extracted from the tree essential oil or a mixture of terpenes which is a tree essential oil component is separated from the CD inclusion complex dissolved in the aqueous layer. Generally, C
Based on the known fact that the D inclusion complex dissociates in an aqueous solution of 60 to 70 ° C. or higher, the water layer is heated to 60 ° C. or higher to dissociate a specific oily component included in the inclusion complex, and the inclusion complex is separated from the aqueous layer. Using a low boiling volatile organic solvent such as diethyl ether, n-hexane, etc., which is difficult to be separated or included in the substitutional CD and hardly soluble in water, at room temperature or under heating at 60 to 70 ° C., A specific oily component is extracted into the organic layer. When the organic solvent is volatilized from this organic layer, the desired specific oily component is obtained. On the other hand, the aqueous layer becomes a transparent substitution-type CD aqueous solution.
【００１１】１回の包接化では特定成分の抽出、分離が
不十分な場合、１度包接された特定の油状成分を原料と
して包接、分離の操作を繰り返すことにより、特定の油
状成分の純度を高めることができる。When the extraction and separation of the specific component is insufficient by one-time inclusion, the specific oily component can be obtained by repeating the operation of inclusion and separation with the specific oily component once included as a raw material. The purity of can be increased.
【００１２】以上の全過程において、本発明に用いる置
換型ＣＤ自体は分解しないので、回収して再利用するこ
とが可能である。In all of the above steps, the substitutional CD itself used in the present invention is not decomposed, so that it can be recovered and reused.
【００１３】[0013]
【実施例】次に、実施例によって本発明をさらに具体的
に説明するが、本発明はこれらの実施例に限定されるも
のではない。実施例１ モノマルトシル−α−ＣＤ（以下、Ｇ2 −α−ＣＤと略
す。）0.６４８ｇまたはモノマルトシル−β−ＣＤ（以
下、Ｇ2 −β−ＣＤと略す。）0.７２９ｇまたはモノマ
ルトシル−γ−ＣＤ（以下、Ｇ2 −γ−ＣＤと略す。）
0.８１０ｇを水5.０ｇに溶解し、ヒノキ葉油1.０ｇを加
えた。対照として水5.０ｇにヒノキ葉油1.０ｇを加え
た。２５℃で１0,０００ｒｐｍ、３０分間攪拌した後、
その溶液を3,０００ｒｐｍで５分間遠心分離して油水分
離を行ってから水層を分取し、これにジエチルエーテル
および水を加えて振盪し、エーテル層からエーテルを揮
発させて抽出油状成分を得た。本実施例におけるヒノキ
葉油と油状成分の組成を第１表に示した。これはキャピ
ラリーガスクロマトグラフ法で分析したもので、表中の
数字はヒノキ葉油または抽出した油状成分中の各成分の
面積百分率を示す。EXAMPLES Next, the present invention will be described more specifically by way of examples, but the present invention is not limited to these examples. Example 1 0.648 g of monomaltosyl-α-CD (hereinafter abbreviated as G 2 -α-CD) or 0.729 g of monomaltosyl-β-CD (hereinafter abbreviated as G 2 -β-CD) or monomaltosyl-γ. -CD (hereinafter referred to as G 2 -γ-CD.)
0.810 g was dissolved in 5.0 g of water, and 1.0 g of cypress leaf oil was added. As a control, 1.0 g of cypress leaf oil was added to 5.0 g of water. After stirring for 30 minutes at 25 ° C. at 10,000 rpm,
The solution was centrifuged at 3,000 rpm for 5 minutes to separate oil and water, and then the aqueous layer was separated. Diethyl ether and water were added to the aqueous layer and the mixture was shaken to evaporate ether from the ether layer to extract an oily component. Obtained. The compositions of cypress leaf oil and oily components in this example are shown in Table 1. This was analyzed by capillary gas chromatography, and the numbers in the table indicate the area percentage of each component in the cypress leaf oil or the extracted oil component.
【００１４】[0014]
【表１】 [Table 1]
【００１５】実施例２ 樹木精油としてスギ葉油を用いたこと以外は、実施例１
と同様に行った。結果を第２表に示す。Example 2 Example 1 except that cedar leaf oil was used as the tree essential oil.
I went the same way. The results are shown in Table 2.
【００１６】[0016]
【表２】 [Table 2]
【００１７】実施例３ 樹木精油としてヒバ材油を用いたこと以外は、実施例１
と同様に行った。結果を第３表に示す。Example 3 Example 1 was repeated, except that as an essential oil for tree, Hiba wood oil was used.
I went the same way. The results are shown in Table 3.
【００１８】[0018]
【表３】 [Table 3]
【００１９】実施例４ 置換型ＣＤとしてメチル−β−ＣＤ（以下、Ｍｅ−β−
ＣＤと略す：β−ＣＤ１分子の水酸基の水素２１個のう
ち平均１2.６個がメチル基に置換されたもの）0.６５７
ｇ、ヒドロキシエチル−β−ＣＤ（以下、ＨＥ−β−Ｃ
Ｄと略す：β−ＣＤ１分子の水酸基の水素２１個のうち
平均１1.２個がヒドロキシエチル基に置換されたもの）
0.８１５ｇ、ヒドロキシプロピル−β−ＣＤ（以下、Ｈ
Ｐ−β−ＣＤと略す：β−ＣＤ１分子の水酸基の水素２
１個のうち平均6.３個がヒドロキシプロピル基に置換さ
れたもの）0.７５１ｇを用いたこと以外は、実施例２と
同様に行った。結果を第４表に示す。Example 4 Methyl-β-CD (hereinafter referred to as Me-β-CD as substitutional CD
Abbreviated as CD: one having an average of 12.6 out of 21 hydrogen atoms of the hydroxyl group of β-CD1 molecule replaced by a methyl group) 0.657.
g, hydroxyethyl-β-CD (hereinafter, HE-β-C
Abbreviated as D: average of 11.2 out of 21 hydrogen atoms of the hydroxyl group of β-CD1 molecule is substituted with hydroxyethyl group)
0.815 g, hydroxypropyl-β-CD (hereinafter, H
Abbreviated as P-β-CD: hydrogen 2 of the hydroxyl group of β-CD1 molecule
The same procedure as in Example 2 was repeated except that 0.751 g of one of which 6.3 on average was substituted with a hydroxypropyl group was used. The results are shown in Table 4.
【００２０】[0020]
【表４】 [Table 4]
【００２１】実施例５ 樹木精油としてクロモジ油を用いたこと以外は、実施例
１と同様に行った。結果を第５表に示す。Example 5 The same procedure as in Example 1 was carried out except that Chromody oil was used as the tree essential oil. The results are shown in Table 5.
【００２２】[0022]
【表５】 [Table 5]
【００２３】実施例６ マルトシル−β−ＣＤ混合物（モノマルトシル−β−Ｃ
Ｄ約４０％、ジマルトシル−β−ＣＤ約４０％、マルト
シル基が３個以上置換したβ−ＣＤ約２０％の混合物）
７３ｇを水５００ｍｌに溶解し、スギ葉油２５ｇを加え
た。室温で１0,０００ｒｐｍ、３０分間攪拌した後、そ
れを濾紙を用いた濾過で油水分離を行ってから水層を取
り出し、これにジエチルエーテルおよび水を加えて振盪
し、ジエチルエーテル層からジエチルエーテルを揮発さ
せて抽出油分を得た。次に、マルトシル−β−ＣＤ混
合物0.７２９ｇを水５ｇに溶解し、抽出油分0.７２ｇ
を加え、２５℃で１0,０００ｒｐｍ、３０分間攪拌した
後、その溶液を3,０００ｒｐｍで５分間遠心分離にかけ
て油水分離を行ってから水層を分取した。次に、これに
ジエチルエーテルおよび水を加えて振盪し、ジエチルエ
ーテル層からジエチルエーテルを揮発させて抽出油分
を得た。結果を第６表に示す。Example 6 Maltosyl-β-CD mixture (monomaltosyl-β-C
D about 40%, dimaltosyl-β-CD about 40%, β-CD about 20% with 3 or more maltosyl groups substituted)
73 g was dissolved in 500 ml of water, and 25 g of cedar leaf oil was added. After stirring at room temperature at 10,000 rpm for 30 minutes, oil-water separation was performed by filtration using filter paper, and then an aqueous layer was taken out. Diethyl ether and water were added to this and the mixture was shaken to remove diethyl ether from the diethyl ether layer. The oil was extracted by evaporation. Next, 0.729 g of maltosyl-β-CD mixture was dissolved in 5 g of water, and 0.72 g of extracted oil was dissolved.
Was added, and the mixture was stirred at 25 ° C. at 10,000 rpm for 30 minutes, and the solution was centrifuged at 3,000 rpm for 5 minutes to separate oil and water, and then the aqueous layer was separated. Next, diethyl ether and water were added to this and shaken, and the diethyl ether was volatilized from the diethyl ether layer to obtain an extracted oil component. The results are shown in Table 6.
【００２４】[0024]
【表６】 [Table 6]
【００２５】実施例７ マルトシル−β−ＣＤ混合物（以下、Ｇ2 −β−ＣＤ混
合物と略す。）２９０ｇを水２Ｌに溶解し、ヒノキ葉油
１２０ｇを加えた。同様に、Ｇ2 −β−ＣＤ混合物２９
０ｇを水２Ｌに溶解し、スギ葉油１２０ｇを加えた。ま
た、グルコシル−α−ＣＤ混合物（モノグルコシル−α
−ＣＤ約４０％、ジグルコシル−α−ＣＤ約４０％、グ
ルコシル基が３個以上置換したα−ＣＤ約２０％の混合
物）２３０ｇを水２Ｌに溶解し、スギ葉油１２０ｇを加
えた。さらに、Ｍｅ−β−ＣＤ２６０ｇを水２Ｌに溶解
し、ヒバ材油１２０ｇを加えた。同様に、Ｍｅ−β−Ｃ
Ｄ２６０ｇを水２Ｌに溶解し、ツェーデル油１２０ｇを
加えた。これら５種類の混合液を、それぞれ室温で5,０
００ｒｐｍ、６０分間攪拌した後、それを濾紙を用いた
濾過で油水分離を行ってから水層を取り出し、これにジ
エチルエーテルおよび水を加えて振盪し、ジエチルエー
テル層からジエチルエーテルを揮発させて各抽出油分を
得た。Example 7 290 g of maltosyl-β-CD mixture (hereinafter abbreviated as G 2 -β-CD mixture) was dissolved in 2 L of water, and 120 g of cypress leaf oil was added. Similarly, G 2 -β-CD mixture 29
0 g was dissolved in 2 L of water, and 120 g of cedar leaf oil was added. Also, glucosyl-α-CD mixture (monoglucosyl-α
-CD about 40%, diglucosyl-α-CD about 40%, a mixture of about 20% α-CD in which 3 or more glucosyl groups have been substituted) (230 g) was dissolved in 2 L of water, and 120 g of cedar leaf oil was added. Further, 260 g of Me-β-CD was dissolved in 2 L of water, and 120 g of hiba wood oil was added. Similarly, Me-β-C
D260 g was dissolved in 2 L of water, and 120 g of Zedel oil was added. Each of these five types of mixed solutions was heated to room temperature at 5.0
After stirring at 00 rpm for 60 minutes, oil-water separation was performed by filtration using filter paper, and then an aqueous layer was taken out. Diethyl ether and water were added thereto and shaken, and diethyl ether was volatilized from the diethyl ether layer. Extracted oil was obtained.
【００２６】実施例８ ヒノキ葉油、スギ葉油、ヒバ材油または実施例７で得た
各抽出油分をテトラヒドロフランで５Ｗ／Ｖ％および１
Ｗ／Ｖ％に希釈した溶液0.５ｍｌを均一に滴下し、１時
間風乾した１０×５ｃｍの濾紙（東洋Ｎｏ．５Ａ）を作
製した。この濾紙を２つ折にして、ヤケヒョウヒダニ
（♀、成虫）２０個体を放ち、折った濾紙の３方をクリ
ップで止めて中に封じ、２４時間室内に放置した後、ダ
ニのノックダウン数を計数した。その後、ノックダウン
したダニを新しい濾紙の袋に移して２５℃、相対湿度
（ＲＨ）７５％下で、さらに２４時間放置し、蘇生しな
いダニ数を計数し、殺ダニ数とした。供試ダニ２０個体
のうちの殺ダニ数の割合を殺ダニ率とし、同じ試験を３
回行い、その平均値から殺ダニ率を求めた。なお、ブラ
ンクとして、無処理の濾紙にテトラヒドロフラン0.５ｍ
ｌを滴下して風乾した濾紙について同様の操作を行っ
た。結果を第７表に示す。Example 8 Hinoki cypress leaf oil, cedar leaf oil, hiba wood oil or each extracted oil obtained in Example 7 was dissolved in tetrahydrofuran at 5 W / V% and 1%.
0.5 ml of a solution diluted to W / V% was uniformly added dropwise and air-dried for 1 hour to prepare a 10 × 5 cm filter paper (Toyo No. 5A). This filter paper was folded in two and 20 bleached mite mites (♀, adults) were released, three of the folded filter papers were clipped and sealed inside and left for 24 hours in the room, after which the number of knockdown mites was counted. . Then, the knocked-down mites were transferred to a new filter paper bag and left at 25 ° C. and 75% relative humidity (RH) for another 24 hours, and the number of mites that did not reanimate was counted to obtain the number of killed mites. The acaricidal rate is defined as the ratio of the acaricidal number of the 20 mites to be tested, and the same test is performed.
The miticide rate was calculated from the average value of the repeated times. As a blank, 0.5 m of tetrahydrofuran on untreated filter paper
The same operation was performed on the filter paper in which 1 was dropped and dried in air. The results are shown in Table 7.
【００２７】[0027]
【表７】 [Table 7]
【００２８】実施例９ 試験菌として下記の７菌株を用い、ヒノキ葉油、スギ葉
油、ヒバ材油、ツェーデル油または実施例７で得た各抽
出油分のエタノールによる２倍希釈系列溶液を５０μｌ
浸み込ませた直径８ｍｍのペーパーディスクを、菌数が
１０5 〜１０6／ｍｌとなるように調整した菌液を添加
した平板培地の表面に置き、細菌は３５℃で２４時間、
カビは２５℃で７日間培養後、発育阻止円を観察した。Example 9 Using the following 7 strains as test strains, 50 μl of a 2-fold dilution series solution of cypress leaf oil, cedar leaf oil, hiba wood oil, ceder oil or each extracted oil obtained in Example 7 with ethanol was used.
An impregnated paper disk having a diameter of 8 mm was placed on the surface of a plate medium to which a bacterial solution adjusted to have a bacterial count of 10 5 to 10 6 / ml was added, and bacteria were kept at 35 ° C. for 24 hours.
After culturing the mold for 7 days at 25 ° C., a growth inhibition circle was observed.
【００２９】試験菌 細菌Enterococcus faecalis IFO 12964 （腸球菌）Escherichi a coli IFO 3301 （大腸菌）Salmonella enteritidis IFO 3313 （サルモネラ菌）Staphylococcus aureus IFO 12732 （黄色ブドウ球菌） カビAspergillu s niger IFO 4407（黒コウジカビ）Fusarium oxysporum IFO 7155 （フザリウム）Penicilliu m citrinum IFO 7784 （ペニシリウム） 使用培地 細菌：Mueller Hinton Medium （Difco) カビ：ポテトデキストロース寒天培地（栄研化学）Test bacteria Bacteria Enterococcus f aecalis IFO 12964 (Enterococcus) Escherichi a coli IFO 3301 (E. coli) Salmonella enteritidis IFO 3313 (Salmonella) Staphylococcus a ureu s IFO 12732 (Staphylococcus aureus) Mold Aspergillu s nige r IFO 4407 Fusarium o xysporum IFO 7155 (Fusarium) Penicilliu m citrinum IFO 7784 (Penicillium) Medium used Bacteria: Mueller Hinton Medium (Difco) Mold: Potato dextrose agar (Eiken Chemical)
【００３０】結果を第８表（１），第８表（２）および
第８表（３）に示す。なお、これら第８表において、
はヒノキ葉油、はヒノキ葉油からのマルトシル−β−
ＣＤ混合物による抽出油、はスギ葉油、はスギ葉油
からのグルコシル−α−ＣＤ混合物による抽出油、は
スギ葉油からのマルトシル−β−ＣＤ混合物による抽出
油、はヒバ材油、はヒバ材油からのメチル−β−Ｃ
Ｄによる抽出油、はツェーデル油、はツェーデル油
からのメチル−β−ＣＤによる抽出油を指す。また、発
育阻止円については、＋は直径１０ｍｍ以上の阻止円の
形成、±は直径１０ｍｍ以下の阻止円の形成を示し、−
は阻止円の形成が見られなかったことを示す。The results are shown in Table 8 (1), Table 8 (2) and Table 8 (3). In addition, in these Table 8,
Is cypress leaf oil, is maltosyl-β- from cypress leaf oil
Extracted oil with CD mixture, is cedar leaf oil, is extracted oil with glucosyl-α-CD mixture from cedar leaf oil, is extracted oil with maltosyl-β-CD mixture from cedar leaf oil, is hiba oil, Methyl-β-C from lumber oil
Oil extracted with D, Zedel oil, refers to oil extracted with methyl-β-CD from Zedel oil. Regarding the growth inhibition circle, + indicates the formation of an inhibition circle having a diameter of 10 mm or more, ± indicates the formation of an inhibition circle having a diameter of 10 mm or less, −
Indicates that no formation of a blocking circle was observed.
【００３１】[0031]
【表８】 [Table 8]
【００３２】[0032]
【表９】 [Table 9]
【００３３】[0033]
【表１０】 [Table 10]
【００３４】[0034]
【発明の効果】本発明によれば、多成分から成る樹木精
油または樹木精油成分であるテルペン類混合物から特定
の油状成分を高選択的、省エネルギー的な方法で分離す
ることができる。また、この方法によりヒノキ精油、ス
ギ精油、ヒバ精油、ツェーデル油等から分離された油状
成分は高い殺ダニ作用や抗菌作用を有している。EFFECTS OF THE INVENTION According to the present invention, a specific oily component can be separated from a multi-component tree essential oil or a terpene mixture which is a tree essential oil component by a highly selective and energy-saving method. Further, oily components separated from hinoki cypress essential oil, cedar essential oil, hiba essential oil, zedel oil and the like by this method have high acaricidal action and antibacterial action.
Claims (3)
ペン類混合物と、サイクロデキストリンの一つ以上の水
酸基の水素が、グルコシル基、マルトシル基、メチル
基、エチル基、ヒドロキシメチル基、ヒドロキシエチル
基およびヒドロキシプロピル基のうちの少なくとも一つ
の基で置換された置換型サイクロデキストリンとを接触
させ、樹木精油または樹木精油成分であるテルペン類混
合物から抽出された油状成分のサイクロデキストリン包
接錯体を得、次いで該包接錯体から油状成分を分離する
ことを特徴とする油状成分の分離方法。1. A tree essential oil or a mixture of terpenes which is a component of a tree essential oil, and hydrogen of one or more hydroxyl groups of cyclodextrin, a glucosyl group, a maltosyl group, a methyl group, an ethyl group, a hydroxymethyl group, a hydroxyethyl group and A cyclodextrin inclusion complex of an oily component extracted from a tree essential oil or a mixture of terpenes which is a tree essential oil component is obtained by contacting with a substituted cyclodextrin substituted with at least one of hydroxypropyl groups, and then A method for separating an oily component, which comprises separating an oily component from the inclusion complex.
を有効成分とする殺ダニ剤。2. A miticide containing the oily component obtained by the method according to claim 1 as an active ingredient.
を有効成分とする抗菌剤。3. An antibacterial agent containing an oily component obtained by the method according to claim 1 as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP08718494A JP3497555B2 (en) | 1994-04-04 | 1994-04-04 | Oil component separation method |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP08718494A JP3497555B2 (en) | 1994-04-04 | 1994-04-04 | Oil component separation method |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH07268384A true JPH07268384A (en) | 1995-10-17 |
| JP3497555B2 JP3497555B2 (en) | 2004-02-16 |
Family
ID=13907909
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP08718494A Expired - Fee Related JP3497555B2 (en) | 1994-04-04 | 1994-04-04 | Oil component separation method |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JP3497555B2 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09157115A (en) * | 1995-12-12 | 1997-06-17 | Kao Corp | Miticidal agent |
| JPH09157116A (en) * | 1995-12-12 | 1997-06-17 | Kao Corp | Miticidal agent |
| JP2008036343A (en) * | 2006-08-10 | 2008-02-21 | Norio Hosoi | Oral wetting agent, and denture adhesive |
-
1994
- 1994-04-04 JP JP08718494A patent/JP3497555B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09157115A (en) * | 1995-12-12 | 1997-06-17 | Kao Corp | Miticidal agent |
| JPH09157116A (en) * | 1995-12-12 | 1997-06-17 | Kao Corp | Miticidal agent |
| JP2008036343A (en) * | 2006-08-10 | 2008-02-21 | Norio Hosoi | Oral wetting agent, and denture adhesive |
Also Published As
| Publication number | Publication date |
|---|---|
| JP3497555B2 (en) | 2004-02-16 |
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