カリオフィレン

Caryophyllene
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優先IUPAC名
(1R,4E,9S)-4,11,11-Trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
別称
(1R,9S,E)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
β-Caryophyllene
trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
識別情報
CAS登録番号 87-44-5 チェック
PubChem 5281515
ChemSpider 4444848 チェック
UNII BHW853AU9H チェック
ChEBI
ChEMBL CHEMBL445740 チェック
特性
化学式 C15H24
モル質量 204.35 g mol−1
密度 0.9052 g/cm3 (17 °C)[1]
沸点

254-257 °C, 270 K, -177 °F [2]

特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

カリオフィレン (Caryophyllene, [ˌkærioʊfɪˈliːn])、あるいは (−)-β-caryophylleneは、多くの精油の成分の天然の二環式のセスキテルペンで、特にチョウジノキ（Syzygium aromaticum、クローブ）の茎や花から採れるクローブオイル[3]、アサ (Cannabis sativa)[4]、ローズマリー[5]、ホップに含まれる[6]。通常、イソカリオフィレン（シス型二重結合異性体）やα-フムレン（別名α-カリオフィレン）と混合して含まれる。

代謝および誘導体

カリオフィレンオキシドという[7]、カリオフィレンのオレフィンがエポキシドとなったものは、探知犬が大麻を特定する原因となる成分であり[8][9]、承認された食品香料でもある[10]。

天然源

精油中のカリオフィレンのおよその量は括弧内に示す。

薬理

カリオフィレンは、ラットでカンナビノイド受容体タイプ2（CB2受容体）の選択的作動薬であり大麻類似の抗炎症作用がある[4]。

出典

  1. ^ SciFinder Record, CAS Registry Number 87-44-5
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