β-カリオフィレン

解説(1R-4E-9S)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene．C15H24(204.34)．β-カリオフィレンともいう．二環性セスキテルペン．フトモモ科Eugenis caryophyllaのクローブ油のなかにα-カリオフィレンとともに含まれているが，アカマツPinns densifloraやヤマジソMosla japonicaなど，植物界に広く存在している．"沸点129～130 ℃(1.9 kPa)．[α]D"－9.9°(ベンゼン)．2分子の塩化水素を付加して融点69～70 ℃ の結晶になる．芳香性材料として使われる．α-カリオフィレンはα-フムレンと同じ．森北出版「化学辞典（第2版）

用途有機合成原料。

天然物の起源Three isomers (α-, β-, and γ-caryophyllene) are found in nature. The β-isomer is the most frequently encountered and most abundant. This sesquiterpene hydrocarbon occurs naturally in approximately 60 essential oils, mainly in that of cloves, from which it was originally isolated. The chemical structure has been thoroughly studied; other studies have been conducted on the isolation and the dipolar moment, as well as on its oxide. Reported found in lime peel oil, lemon, grapefruit, guava fruit, raspberry, black currant, carrot, celery seed, cinnamon bark, anise, nutmeg, cumin seed, ginger, pepper, peppermint oil, mace, laurel and caraway herb.

使用β-Caryophyllene is notable for having a cyclobutane ring, a rarity in nature. β-Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. β-Caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.