JP5745805B2 - Use of sedative effect imparting agent and sedative and 2R-teaspirane - Google Patents
Use of sedative effect imparting agent and sedative and 2R-teaspirane Download PDFInfo
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Description
本発明は、鎮静効果付与剤及び鎮静剤並びに２Ｒ−テアスピランの使用に関する。 The present invention relates to a sedative effect-imparting agent and a sedative and use of 2R-teaspirane .
古来より、香りは心理的及び生理的作用を有することが知られている。花や木など植物に由来する芳香成分（精油）を用いて、心身の健康や美容を増進し、ストレスを解消し心身をリラックスさせる技術としては、「アロマテラピー」が知られている。
特に、ストレス社会といわれる現代では、主に精神安定、ストレス解消及び不眠症の治療に対してアロマテラピー療法が注目されている。例えば、ラベンダーやカモミールなどの精油エキスには鎮静及び催眠効果があることが知られている（特許文献１及び非特許文献１参照）。また、バラの香気成分であるジメトキシメチルベンゼンには鎮静効果があることが知られている（特許文献２参照）。
Since ancient times, fragrances have been known to have psychological and physiological effects. "Aromatherapy" is known as a technology that uses aromatic components (essential oils) derived from plants such as flowers and trees to promote mental and physical health and beauty, relieve stress and relax mind and body.
In particular, in the present day referred to as a stress society, aromatherapy therapy has attracted attention mainly for the treatment of mental stability, stress relief and insomnia. For example, it is known that essential oil extracts such as lavender and chamomile have sedative and hypnotic effects (see Patent Document 1 and Non-Patent Document 1). In addition, it is known that dimethoxymethylbenzene, which is an aromatic component of roses, has a sedative effect (see Patent Document 2).
しかしながら、現代人は常にストレスに曝されているので、より優れた鎮静効果を有する芳香成分の開発が望まれている。
本発明は、上記のような事情に鑑み、鎮静効果を付与したい対象物に優れた鎮静効果を付与する鎮静効果付与剤及び鎮静効果を有する鎮静剤を提供することを目的とする。
However, since modern people are constantly exposed to stress, it is desired to develop an aromatic component having a more excellent sedative effect.
In view of the circumstances as described above, an object of the present invention is to provide a sedative effect imparting agent that imparts an excellent sedative effect to an object to which a sedative effect is desired and a sedative agent that has a sedative effect.
本発明の鎮静効果付与剤は、
下記化学式で示される２Ｒ−テアスピランを含有することを特徴とする。
The sedative effect-imparting agent of the present invention is
It contains 2R-teaspirane represented by the following chemical formula.
本発明の鎮静剤は、
下記化学式で示される２Ｒ−テアスピランを含有することを特徴とする。
The sedative of the present invention is
It contains 2R-teaspirane represented by the following chemical formula.
本発明の鎮静効果付与剤及び鎮静剤は、前記化学式で示される２Ｒ−テアスピランを有効成分として含有する。この鎮静効果付与剤及び鎮静剤に含有される２Ｒ−テアスピランは、意識水準を鎮静化する。よって、本発明の鎮静効果付与剤は、鎮静効果を付与したい対象物に優れた鎮静効果を付与することができる。また、本発明の鎮静剤は優れた鎮静効果を有する。 The sedative effect imparting agent and sedative of the present invention contain 2R-teaspirane represented by the above chemical formula as an active ingredient. This sedative effect-imparting agent and 2R-teaspirane contained in the sedative soothe consciousness level. Therefore, the sedative effect imparting agent of the present invention can impart an excellent sedative effect to an object to which a sedative effect is desired. Moreover, the sedative of the present invention has an excellent sedative effect.
本実施形態の鎮静効果付与剤及び鎮静剤は、２Ｒ−テアスピランを有効成分として含有する。この鎮静効果付与剤及び鎮静剤に含有される２Ｒ−テアスピランの香りは、吸入されることにより意識水準を鎮静化する。本実施形態の鎮静効果付与剤は、鎮静効果を付与したい組成物等に優れた鎮静効果を付与することができる。また、本実施形態の鎮静剤は優れた鎮静効果を有する。
２Ｒ−テアスピランは、以下の化学式で示される。
The sedative effect imparting agent and sedative of the present embodiment contain 2R-teaspirane as an active ingredient. The scent of 2R-teaspiran contained in the sedative effect imparting agent and the sedative calms the level of consciousness when inhaled. The sedative effect imparting agent of the present embodiment can impart an excellent sedative effect to a composition or the like for which a sedative effect is desired to be imparted. Moreover, the sedative of this embodiment has an excellent sedative effect.
2R-teaspirane is represented by the following chemical formula.
以下、本実施形態に係る鎮静効果付与剤及び鎮静剤について詳細に説明する。
(２Ｒ−テアスピランについて)
テアスピランは、紅茶、及び、木イチゴ、ラズベリー、パッションフルーツなどの果皮や果肉に含まれる、無色の液体の香気成分である。テアスピランは、イチゴ様で青臭さと甘みのある香りを呈し、含有する濃度が高いとショウノウ様でウッディな香りを呈する。テアスピランは、例えばパッションフルーツの果皮をそのままあるいは乾燥した後に適当な大きさに切断したり、粉砕加工したりしたもの等から抽出して得られる抽出エキスに含まれている。また、この抽出エキスを分離精製して得られる画分を使用してもよい。抽出方法は、特に限定されないが、水蒸気蒸留法、熱水蒸留法等の蒸留法、有機溶媒抽出法、油脂吸着抽出法、圧搾法等一般的な精油の抽出方法を用いることができ、特に、水蒸気蒸留法を用いることが好ましい。
Hereinafter, the sedative effect imparting agent and the sedative according to this embodiment will be described in detail.
(About 2R-teaspiran)
Theaspiran is a colorless liquid aroma component contained in black tea and pericarp and flesh such as wood strawberry, raspberry and passion fruit. Theaspiran has a strawberry-like blue odor and a sweet scent, and a high concentration of it shows a camphor-like, woody scent. Theaspirane is contained, for example, in an extract obtained by extracting the fruit skin of passion fruit as it is or after being dried and then cut into a suitable size or pulverized. Further, a fraction obtained by separating and purifying this extract may be used. The extraction method is not particularly limited, but a general essential oil extraction method such as a distillation method such as a steam distillation method or a hot water distillation method, an organic solvent extraction method, a fat adsorption extraction method, or a compression method can be used. It is preferable to use a steam distillation method.
また、テアスピランは、化学合成により合成されたものが市販されているが、一般的には鏡像異性体の混合物であるラセミ体のみ入手可能である。
さらに、テアスピランは、化学構造的に２位と５位に不斉炭素を有し、理論上は４つの立体異性体が考えられ、そのうち２位に不斉炭素を有する鏡像異性体の合成方法は、高砂香料工業株式会社により確立されている（国際公開第０７／０３２２７９号パンフレット）。
In addition, theaspirane synthesized by chemical synthesis is commercially available, but generally only a racemate that is a mixture of enantiomers is available.
Furthermore, theaspirane has an asymmetric carbon in the 2nd and 5th positions in terms of chemical structure, and theoretically there are four stereoisomers. Of these, the method for synthesizing an enantiomer having an asymmetric carbon in the 2nd position is Established by Takasago International Corporation (International Publication No. 07/032279 pamphlet).
２Ｒ−テアスピランは、メントール、ショウノウ様のさわやかな香りを呈し、２Ｓ−テアスピランは、テルペン炭化水素のようなフレッシュな香りとウッディな香りを有するとされる。
本実施形態の鎮静効果付与剤は、２Ｒ−テアスピランを有効成分として含有する。鎮静効果付与剤により鎮静効果を付与された組成物等から、前記有効成分が揮発して、その香りを使用者が吸入すると、前述の鎮静効果が奏される。鎮静効果付与剤は、有効成分のみで構成されていてもよいが、効果を妨げない範囲の量であれば、希釈剤、助剤、添加剤等の任意の他の成分を含有していてもよい。
2R-teaspiran has a refreshing scent of menthol and camphor, and 2S-teaspiran is said to have a fresh scent such as terpene hydrocarbon and a woody scent.
The sedative effect imparting agent of this embodiment contains 2R-teaspirane as an active ingredient. When the active ingredient is volatilized from a composition or the like having a sedative effect imparted by a sedative effect imparting agent and the user inhales the scent, the aforementioned sedative effect is exhibited. The sedative effect-imparting agent may be composed of only active ingredients, but may contain any other components such as diluents, auxiliaries, additives, etc., as long as the amount does not interfere with the effect. Good.
化粧料等の所定の組成物に鎮静効果付与剤を添加すれば、該組成物に鎮静効果を付与することができる。すなわち、化粧料等に鎮静効果付与剤を添加して、鎮静効果を有する化粧料等とすることができる。さらに、衣類、雑貨類等に鎮静効果付与剤を浸透または付着させれば、浸透または付着した鎮静効果付与剤から前記有効成分が揮発するので、衣類、雑貨等に鎮静効果を付与することができる。 If a sedative effect imparting agent is added to a predetermined composition such as a cosmetic, a sedative effect can be imparted to the composition. That is, a sedative effect-imparting agent can be added to cosmetics and the like to make cosmetics having a sedative effect. Furthermore, if the sedative effect-imparting agent permeates or adheres to clothing, sundries, etc., the active ingredient volatilizes from the permeated or adhered sedative effect-imparting agent, so that a sedative effect can be imparted to clothing, miscellaneous goods, etc. .
鎮静効果付与剤を化粧料、医薬品等の組成物に添加して鎮静効果を付与する場合には、組成物中の鎮静効果付与剤の配合量は０．０００１質量％以上１００質量％以下が好ましく、０．００１質量％以上５０質量％以下がより好ましく、０．０１質量％以上３０質量％以下がさらに好ましい。
本実施形態の鎮静剤は、２Ｒ−テアスピランを有効成分として含有する。鎮静剤から、前記有効成分が揮発して、その香りを使用者が吸入すると、前述の鎮静効果が奏される。
When a sedative effect imparting agent is added to a composition such as cosmetics or pharmaceuticals to impart a sedative effect, the blending amount of the sedative effect imparting agent in the composition is preferably 0.0001 mass% or more and 100 mass% or less. 0.001% by mass to 50% by mass is more preferable, and 0.01% by mass to 30% by mass is more preferable.
The sedative of this embodiment contains 2R-teaspirane as an active ingredient. When the active ingredient volatilizes from the sedative and the user inhales the scent, the sedative effect described above is exhibited.
鎮静剤中の有効成分の含有量は特に限定されるものでないが、その鎮静剤全体の中の有効成分の含有量は０．００１ｐｐｍ以上１００質量％以下が好ましく、０．０１ｐｐｍ以上１０質量％以下がさらに好ましく、０．１ｐｐｍ以上１質量％以下が特に好ましい。
本実施形態の鎮静効果付与剤及び鎮静剤は、本発明の効果を達成できる限り、その形態については特に制限はなく、液状、ペースト状、ゲル状、固形状等任意の形態で使用できる。
The content of the active ingredient in the sedative is not particularly limited, but the content of the active ingredient in the whole sedative is preferably 0.001 ppm or more and 100% by mass or less, and 0.01 ppm or more and 10% by mass or less. Is more preferable, and 0.1 ppm or more and 1% by mass or less is particularly preferable.
The sedative effect-imparting agent and sedative of this embodiment are not particularly limited as long as the effects of the present invention can be achieved, and can be used in any form such as liquid, paste, gel, and solid.
また、本実施形態の鎮静効果付与剤及び鎮静剤は、本発明の効果を達成できる限り、その剤形については特に制限はなく、例えば、液剤、粉末剤、顆粒剤、エアゾール剤、固形剤、ジェル剤等が挙げられるが、特にこれらに限定されない。
鎮静効果を付与する対象物として、限定はされないが、例えば、香水、オードトワレ、オーデコロンなどのフレグランス、クリーム、乳液類、化粧水、マッサージ用ジェル、マッサージ用クリーム、ファンデーション類、粉白粉、口紅、石鹸、シャンプー・リンス類、ボディーシャンプー、ボディーリンス、ボディーパウダー類、エアゾール、浴剤類等が挙げられる。
In addition, the sedative effect imparting agent and sedative of the present embodiment are not particularly limited as long as the effect of the present invention can be achieved. For example, liquids, powders, granules, aerosols, solids, Gel agents and the like can be mentioned, but not limited to these.
The object to which the sedative effect is imparted is not limited, but for example, fragrances such as perfume, eau de toilette, eau de cologne, cream, milky lotion, lotion, massage gel, massage cream, foundations, powdered white powder, lipstick, soap Shampoos and rinses, body shampoos, body rinses, body powders, aerosols, bath preparations and the like.
また、鎮静剤として、限定はされないが、例えば、香水、オードトワレ、オーデコロンなどのフレグランス、クリーム、乳液類、化粧水、マッサージ用ジェル、マッサージ用クリーム、ファンデーション類、粉白粉、口紅、石鹸、シャンプー・リンス類、ボディーシャンプー、ボディーリンス、ボディーパウダー類、エアゾール、浴剤類等が挙げられる。 In addition, as a sedative, although not limited, for example, fragrances such as perfume, eau de toilette, eau de cologne, cream, milky lotion, lotion, massage gel, massage cream, foundations, white powder, lipstick, soap, shampoo Examples include rinses, body shampoos, body rinses, body powders, aerosols, bath preparations, and the like.
さらに、例えば、本実施形態の鎮静効果付与剤及び鎮静剤を、芳香剤、消臭剤、アロマキャンドル、インセンス、文房具、財布、バッグ、靴等の任意の雑貨類や、例えば下着、洋服、帽子、ストッキング、靴下等の任意の衣類に浸透または付着させれば、浸透または付着した鎮静効果付与剤及び鎮静剤から前記有効成分が揮発するので、雑貨、衣類等に鎮静効果を付与することができる。雑貨、衣服等の素材に本実施形態の鎮静効果付与剤及び鎮静剤を浸透または付着させ、その素材から製品を作製してもよいし、完成した製品に本実施形態の鎮静効果付与剤及び鎮静剤を浸透または付着させてもよい。その他食用として錠剤、タブレット、キャンディー、ガムなどに添加することなども考えられる。
なお、本実施形態の鎮静効果付与剤及び鎮静剤の様々な使用態様を例示したが、それらに限定されるものではなく、本発明の効果を達成できる限り、任意の態様で用いることができる。
Furthermore, for example, the sedative effect-imparting agent and sedative of the present embodiment may be selected from any miscellaneous goods such as fragrance, deodorant, aroma candle, incense, stationery, wallet, bag, shoes, etc., for example, underwear, clothes, If it penetrates or adheres to any clothing such as hats, stockings, socks, etc., the active ingredient volatilizes from the soaking or adhering sedative effect imparting agent and sedative agent, so that it can impart a sedative effect to miscellaneous goods, clothing, etc. it can. The sedative effect imparting agent and sedative of the present embodiment may be permeated or adhered to materials such as sundries and clothes, and a product may be produced from the material, or the sedative effect imparting agent and sedative of the present embodiment may be applied to a finished product. The agent may be infiltrated or adhered. In addition, it may be added to tablets, tablets, candies, gums and the like for food.
In addition, although various usage modes of the sedative effect imparting agent and the sedative agent of the present embodiment have been exemplified, the present invention is not limited thereto, and can be used in any mode as long as the effects of the present invention can be achieved.
以下に実施例を示してさらに詳細に説明する。
テアスピランのラセミ体、２Ｓ−テアスピラン、及び、２Ｒ−テアスピランを、濃度が０．１質量％となるよう、エタノールで希釈したものを試験試料として用いて、試験試料の香りが意識水準に及ぼす影響を検討した。
テアスピランのラセミ体、２Ｓ−テアスピラン、及び、２Ｒ−テアスピランは、高砂香料工業株式会社製のものを用いた。
Examples will be described below in more detail.
The effect of the scent of the test sample on the level of consciousness using a racemate of theaspirane, 2S-theaspirane, and 2R-theaspirane diluted with ethanol to a concentration of 0.1% by mass as the test sample investigated.
As the racemic body of theaspirane, 2S-teaspiran, and 2R-teaspirane, those manufactured by Takasago International Corporation were used.
まず、本実施例において鎮静効果の確認のために採用した試験方法について説明する。
（ＣＮＶ測定による意識水準評価試験の方法について）
事象関連電位のひとつである随伴陰性変動（ＣＮＶ：Contingent Negative Variation（以下、「ＣＮＶ」と称する。））を測定することにより被験者の意識水準を評価し、鎮静効果の検討を行った。ＣＮＶは、その早期成分の変動の大きさが意識の覚醒水準と正の相関を示し、香りが意識水準に及ぼす効果（精神鎮静/高揚効果）を定量評価できることが報告されている。
First, the test method employed for confirming the sedative effect in this example will be described.
(About method of consciousness level evaluation test by CNV measurement)
The level of consciousness of the subject was evaluated by measuring contingent negative variation (CNV), which is one of event-related potentials, and the sedative effect was examined. CNV has been reported to be able to quantitatively evaluate the effect of a scent on the level of consciousness (mental sedation / uplifting effect), with the magnitude of fluctuation of its early component showing a positive correlation with the level of consciousness.
そこで、２Ｒ−テアスピランの鎮静効果を確認するために、ＣＮＶ測定による意識水準評価試験により検討を行った。
本実施例においては２０歳代女性６名を被験者とした。被験者には予め試験内容を説明し、文書にて試験参加への同意を得た。
本実施例においては、被験者の頭頂部、前頭極部中央、左耳及び右耳に脳波計の白金電極を装着し、被験者の頭頂部の電位Ｃｚ、前頭極部中央の電位Ｆｐｚ、左耳の電位Ａ１、及び、右耳の電位Ａ２を計測した。そして、Ｆｐｚを基準として、Ｃｚ−（Ａ１＋Ａ２）の電位差を算出した。脳波計は、日本光電株式会社製、誘発電位検査装置ＭＥＢ−２２１６を用いた。
Therefore, in order to confirm the sedative effect of 2R-teaspiran, examination was conducted by a consciousness level evaluation test by CNV measurement.
In this example, six women in their twenties were subjects. The test contents were explained to the subjects in advance, and written consent was obtained.
In this example, a platinum electrode of an electroencephalograph is attached to the subject's parietal region, frontal pole center, left ear and right ear, and the subject's parietal potential Cz, frontal pole center potential Fpz, left ear's The potential A1 and the right ear potential A2 were measured. Then, the potential difference of Cz− (A1 + A2) was calculated using Fpz as a reference. As the electroencephalograph, an evoked potential inspection device MEB-2216 manufactured by Nihon Kohden Co., Ltd. was used.
被験者にヘッドフォンでクリック音を聞かせ、クリック音がしてから数秒後に点滅する発光ダイオードの点灯に合わせて手元のスイッチを押すという課題を行なわせ、課題の実行時に発生するＣＮＶを計測した。（Ａ）試験試料の香りを嗅がせる場合は、コットン片に５μｌの試験試料をしみこませ、鼻下に貼付して自然呼吸とともに香りを嗅がせた。（Ｂ）試験試料の香りを嗅がせない場合は、コットン片に５μlのエタノールをしみこませ、十分に揮発させた後にコットン片を鼻下に貼付し、上記課題の一連の動作の間、常に呼吸と共に香りを嗅がせた。試験試料の香りを嗅がせた場合（Ａ）と試験試料の香りを嗅がせない場合（Ｂ）のそれぞれについて、３０回繰り返して各ＣＮＶを計測し、積算したＣＮＶの波形の早期成分（４５０ｍｓ〜１０００ｍｓ）の面積（ＣＮＶ面積値）を取得した。そして試験試料の香りを嗅がせた場合（Ａ）のＣＮＶ面積値と、試験試料の香りを嗅がせない場合（Ｂ）のＣＮＶ面積値とを比較し、テアスピランのラセミ体、２Ｓ−テアスピラン、及び、２Ｒ−テアスピランの意識水準に及ぼす効果を評価した。試験試料の香りを嗅がせた場合（Ａ）のＣＮＶ面積値が、試験試料の香りを嗅がせない場合（Ｂ）のＣＮＶ面積値より減少している場合は、試験試料が意識水準を鎮静化したことを意味し、増加した場合は、意識水準を活性化させたことを意味する。 The subject was asked to listen to the click sound with headphones, and the task of pressing the switch at hand in response to the lighting of the light emitting diode flashing several seconds after the click sound was made, and the CNV generated when the task was executed was measured. (A) In order to smell the scent of the test sample, 5 μl of the test sample was soaked in a piece of cotton and applied under the nose to smell the scent along with natural breathing. (B) If the scent of the test sample cannot be sniffed, soak the cotton piece with 5 μl of ethanol, volatilize it sufficiently, and then apply the cotton piece under the nose. And smelled. For each of the cases where the scent of the test sample was sniffed (A) and the case where the scent of the test sample was not sniffed (B), each CNV was repeatedly measured 30 times, and the CNV waveform early component (450 ms to 1000 ms) area (CNV area value) was obtained. Then, the CNV area value in the case where the scent of the test sample is sniffed (A) and the CNV area value in the case where the scent of the test sample cannot be sniffed are compared, and a racemic body of 2 spirane, 2S-theaspirane, and The effect of 2R-teaspiran on the level of consciousness was evaluated. When the scent of the test sample is sniffed (A), the CNV area value is less than the CNV area value of (B) when the scent of the test sample is not sniffed. If it increases, it means that the level of consciousness has been activated.
（ＣＮＶ測定による意識水準評価試験の結果について）
結果を図１に示した。結果は、試験試料の香りを嗅がせた場合（Ａ）の被験者６名のＣＮＶ面積の平均値と、試験試料の香りを嗅がせない場合（Ｂ）の被験者６名のＣＮＶ面積の平均値とを比較して示した。図１において、白色のバーが試験試料の香りを嗅がせない場合（Ｂ）、黒色のバーが試験試料の香りを嗅がせた場合（Ａ）のＣＮＶ面積値を示している。また、一対の標本によるt検定を実施し有意差検定を実施した。
(About the result of the consciousness level evaluation test by CNV measurement)
The results are shown in FIG. The results are: the average value of CNV area of 6 subjects when smelling the test sample (A), and the average value of CNV area of 6 subjects when not smelling the test sample (B) Are shown in comparison. In FIG. 1, the CNV area value is shown when the white bar cannot smell the test sample (B) and when the black bar smells the test sample (A). In addition, a t-test with a pair of specimens was performed, and a significant difference test was performed.
図１から明らかな様に、２Ｒ−テアスピランの香りを嗅がせた場合には、香りを嗅がせない場合に比べて、統計的に有意にＣＮＶ面積値を減少させており（＊ｐ＜０．０５）、意識水準は鎮静化していることがわかる。一方、テアスピランのラセミ体の香り、及び、２Ｓ−テアスピランの香りを嗅がせた場合には、いずれも有意な影響を及ぼさないことがわかる。
このことから、２Ｒ−テアスピランは、テアスピランのラセミ体、及び、２Ｓ−テアスピランに比して、顕著に意識水準を鎮静化することがわかった。
以下、本発明の鎮静効果付与剤の好適な実施例について詳しく説明するが、本発明はこれらに限定されるものではない。
As can be seen from FIG. 1, when the scent of 2R-teaspiran was allowed to smell, the CNV area value was statistically significantly decreased (* p <0. 05), it can be seen that the level of consciousness has subsided. On the other hand, it can be seen that when the scent of the racemic form of theaspiran and the scent of 2S-theaspiran are made to smell, neither has a significant effect.
From this, it was found that 2R-teaspirane markedly calms the level of consciousness compared to the racemic form of theaspirane and 2S-teaspirane.
Hereinafter, preferred examples of the sedative effect imparting agent of the present invention will be described in detail, but the present invention is not limited thereto.
芳香性繊維
キュプロアンモニウムセルロース溶液（セルロース濃度１０質量％、アンモニウム濃度７質量％、銅濃度３．６質量％）に、本発明の鎮静効果付与剤を内包したマイクロカプセル（粒子径５０μｍ以下、マイクロカプセルに占める鎮静効果付与剤の割合は５０質量％）をセルロース質量に対して０．１〜２０質量％の範囲内で添加、混和した後、通常の湿式紡糸方法に従って紡糸し、精錬工程、乾燥工程を経て、芳香性繊維を得た。
Aromatic fiber A microcapsule (particle size of 50 μm or less, microcapsule containing a sedative effect-imparting agent of the present invention in a cupro ammonium cellulose solution (cellulose concentration 10 mass%, ammonium concentration 7 mass%, copper concentration 3.6 mass%) The ratio of the sedative effect imparting agent is 50% by mass) in the range of 0.1 to 20% by mass with respect to the cellulose mass, and after mixing, spinning according to a normal wet spinning method, refining step, drying step After that, an aromatic fiber was obtained.
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| CH613379A5 (en) * | 1975-03-11 | 1979-09-28 | Givaudan & Cie Sa | Perfuming and/or flavouring compositions |
| US4277618A (en) * | 1977-12-12 | 1981-07-07 | Givaudan Corporation | 2-Substituted-1-acetoxy and hydroxy-1-methyl-cyclohexanes |
| JPS61134386A (en) * | 1984-12-06 | 1986-06-21 | Ogawa Koryo Kk | Production of theaspirone |
| JP2003137758A (en) * | 2001-10-29 | 2003-05-14 | Kiyomitsu Kawasaki | Masking composition for hair cosmetic and hair cosmetic containing the same and method for masking hair cosmetic |
| JP2004018431A (en) * | 2002-06-14 | 2004-01-22 | Kiyomitsu Kawasaki | Perfume composition for oral cavity and oral cavity composition containing the same |
| JP2005015686A (en) * | 2003-06-27 | 2005-01-20 | Kiyomitsu Kawasaki | Fruit-like flavor composition |
| DE112006002442T5 (en) * | 2005-09-13 | 2008-07-17 | Takasago International Corp. | Process for the preparation of optically active theaspirane |
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