カリオフィレン

出典: フリー百科事典『ウィキペディア(Wikipedia)』
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Caryophyllene
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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, [ˌkærifɪˈln])、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[編集]

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s[編集]

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[編集]

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英語版(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[編集]

  1. ^ SciFinder Record, CAS Registry Number 87-44-5
  2. ^ Baker, Richard R. (2004). “The pyrolysis of tobacco ingredients”. Journal of Analytical and Applied Pyrolysis 71 (1): 223–311. doi:10.1016/s0165-2370(03)00090-1. 
  3. ^ a b “Local anaesthetic activity of beta-caryophyllene”. Farmaco 56 (5–7): 387–9. (2001). doi:10.1016/S0014-827X(01)01092-8. PMID 11482764. 
  4. ^ a b c “Beta-caryophyllene is a dietary cannabinoid”. Proceedings of the National Academy of Sciences of the United States of America 105 (26): 9099–104. (July 2008). doi:10.1073/pnas.0803601105. PMC: 2449371. PMID 18574142. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2449371/. 
  5. ^ a b “Production and diversity of volatile terpenes from plants on calcareous and siliceous soils: effect of soil nutrients”. J. Chem. Ecol. 34 (9): 1219–29. (September 2008). doi:10.1007/s10886-008-9515-2. PMID 18670820. 
  6. ^ Glenn Tinseth, "Hop Aroma and Flavor", January/February 1993, Brewing Techniques. <http://realbeer.com/hops/aroma.html> Accessed July 21, 2010.
  7. ^ Yang, D.; Michel, L.; Chaumont, J. P.; Millet-Clerc, J. (1999-11-01). “Use of caryophyllene oxide as an antifungal agent in an in vitro experimental model of onychomycosis”. Mycopathologia 148 (2): 79–82. ISSN 0301-486X. PMID 11189747. 
  8. ^ Ethan (2011). “Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects”. Br J Pharmacol 163 (7): 1344–1364. doi:10.1111/j.1476-5381.2011.01238.x. PMC: 3165946. PMID 21749363. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3165946/. 
  9. ^ Stahl, E; Kunde, R (1973). “Die Leitsubstanzen der Haschisch-Suchhunde”. Kriminalistik: Z Gesamte Kriminal Wiss Prax. 27: 385–389. 
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  13. ^ Alma, M. Hakkı; Ertaş, Murat; Nitz, Siegfrie; Kollmannsberger, Hubert (May 2007). Lucia, Lucian A.; Hubbe, Martin A.. eds. “Chemical composition and content of essential oil from the bud of cultivated Turkish clove” (PDF). BioResources (Raleigh, North Carolina, USA: North Carolina State University) 2 (2): 265–269. ISSN 1930-2126. http://www.ncsu.edu/bioresources/BioRes_02/BioRes_02_2_265_269_Alma_ENK_CloveOil_Turkish.pdf 2010年9月6日閲覧. "The results showed that the essential oils mainly contained about [...] 3.56% β-Caryophyllene" 
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  22. ^ “Aroma compound analysis of Piper nigrum and Piper guineense essential oils from Cameroon using solid-phase microextraction-gas chromatography, solid-phase microextraction-gas chromatography-mass spectrometry and olfactometry”. J Chromatogr A 976 (1–2): 265–75. (November 2002). doi:10.1016/S0021-9673(02)00376-X. PMID 12462618. 
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  26. ^ “Volatile constituents of essential oils isolated from different parts of cinnamon (Cinnamomum zeylanicum Blume)”. Journal of the Science of Food and Agriculture 83 (1): 53–55. (2003). doi:10.1002/jsfa.1277. 
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  31. ^ http://www.rain-tree.com/copaiba.htm