(-)-フェンコン

危険有害性情報のコード(GHS)

• 絵表示(GHS)

  

• 注意喚起語

  Warning

• 危険有害性情報

  H411：長期的影響により水生生物に毒性

• 注意書き

  P273：環境への放出を避けること。

  P391：漏出物を回収すること。

  P501：内容物/容器を．．．に廃棄すること。

(-)-フェンコン 価格

(-)-フェンコン 化学特性,用途語,生産方法

• 外観

  無色～うすい黄色, 澄明の液体

• 溶解性

  エタノール及びアセトンに極めて溶けやすく、水にほとんど溶けない。

• 用途

  香料に配合する。

• 化学的特性

  CLEAR COLOURLESS TO SLIGHTLY YELLOW LIQUID

• 天然物の起源

  Reported to be found in many essential oils, including those of Thuja plicata, T.occiden-talis, T.standi shii, Russian anise, fennel, a few Artemisia varieties (A. frigida, A . verlotorum and A . santolinaefolia), Lavandula stoechas and L. burmannii. The highest levels (12-19%) are found in fennel oil (Fenarolis Handbook of Flavor Ingredients, 1975; Gildemeister & Hoffman, 1963).

• 使用

  (1R,?4S)?-1,?3,?3-?Trimethylbicyclo[2.2.1]?heptan-?2-?one also known more commonly as (-)-Fenchone is a chiral intermediate of Fenchone and is currently being used for studies ranging from inhibitory effects of monoterpenes on human TRPA1 and odorant receptor of the malaria vector Anopheles gambiae.

• 製造方法

  By isolation from cedar leaf oil (Thuja oil) or by various synthetic methods (Arctander, 1969).

• 定義

  ChEBI: A fenchone that has (1R,4S)-stereochemistry. It is a constituent of the essential oils obtained from fennel.

• 一般的な説明

  (1R)-(-)-Fenchone is a bridged bicyclic ketone found in fennel oil and thuja oil.

• 薬理学

  In mice, fenchone injected sc in sesame oil produced clonic convulsions at non-lethal doses, with a median convulsive dose (CD₅₀) of 1133 mg/kg, and a dose of 500 mg/kg given sc was an effective arousal agent, reducing the hexobarbitone sleep time (Wenzel & Ross, 1957). In rats, an ip dose of 500 mg/kg had no effect on pentobarbitone-depressed respiration, while ip doses of 50-400 mg/kg increased running activity but did not affect total activity (Wenzel & Ross, 1957). Fenchone showed some antispasmodic action on excised mouse intestine (Haginiwa, Harada & Morishita, 1963), and at 260 mmol/kg showed good choleretic properties of moderately long duration when given orally in olive oil to rats (M?rsdorf, 1966). Thomas (1958) reported that it acted as a central nervous system stimulant. Fenchone has been used medically as a counter-irritant (Merck Index, 1968).

• 代謝

  Rimini (1901 & 1909) showed that, in the dog, fenchone was probably oxidized to 4-hydroxyfenchone. Reinartz & Zanke (1936) showed that there were other products. They separated, as lead salts, the glucuronides from the urine of dogs receiving d-fenchone. The lead was removed with sulphuric acid and the resulting solution was hydrolysed. In the resulting mixture of hydroxyfen chones, the presence of 4- and 5-hydroxyfenchones and 7r-apofenchone-3-carboxylic acid was demon strated (Williams, 1959).

• 純化方法

  Purification is as for the (+)-enantiomer above and should have the same physical properties except for opposite optical rotations. UV has max 285nm ( 12.29). [Braun & Jacob Chem Ber 66 1461 1933, UV: Ohloff et al. Chem Ber 90 106 1957.] [Beilstein 7 III 392, 7 IV 212.]

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(-)-フェンコン スペクトルデータ(¹HNMR、IR1、MS、Raman)

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