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カリオフィレン

出典: フリー百科事典『ウィキペディア（Wikipedia）』
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

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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

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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

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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. 
  10. ^ http://www.thegoodscentscompany.com/data/rw1023631.html
  11. ^ Mediavilla, Vito. “Essential oil of Cannabis sativa L. strains”. International Hemp Association. 11 July 2008閲覧。
  12. ^ “Antioxidant and biocidal activities of Carum nigrum (seed) essential oil, oleoresin, and their selected components”. J. Agric. Food Chem. 54 (1): 174–81. (January 2006). doi:10.1021/jf0518610. PMID 16390196. 
  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 September 6, 2010閲覧. "The results showed that the essential oils mainly contained about [...] 3.56% β-Caryophyllene" 
  14. ^ Clove Essential Oil
  15. ^ “Terpene Biosynthesis in Glandular Trichomes of Hop”. Plant Physiol. 148 (3): 1254–66. (November 2008). doi:10.1104/pp.108.125187. PMC 2577278. PMID 18775972. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2577278/. 
  16. ^ Bernotienë, Genovaitë; Nivinskienë, Ona; Butkienë, Rita; Mockutë, Danutë (2004). “Chemical composition of essential oils of hops (Humulus lupulus L.) growing wild in Auktaitija”. Chemija. 2 (Vilnius, Lithuania: Lithuanian Academy of Sciences) 4: 31–36. ISSN 0235-7216. http://www.elibrary.lt/resursai/LMA/Chemija/C-31.pdf September 6, 2010閲覧。. 
  17. ^ “Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting”. J. Agric. Food Chem. 56 (2): 380–5. (January 2008). doi:10.1021/jf0725629. PMID 18095647. 
  18. ^ Silva, Maria Goretti de Vasconcelos; Matos, Francisco José de Abreu; Lopes, Paulo Roberto Oliveira; Silva, Fábio Oliveira; Holanda, Márcio Tavares (August 2, 2004). Cragg, Gordon M.; Bolzani, Vanderlan S.; Rao, G. S. R. Subba. eds. “Composition of essential oils from three Ocimum species obtained by steam and microwave distillation and supercritical CO2 extraction” (PDF). Arkivoc (ARKAT USA, Inc.) 2004 (vi): 66–71. doi:10.3998/ark.5550190.0005.609. ISSN 1424-6376. http://www.arkat-usa.org/get-file/19788/ September 6, 2010閲覧。. 
  19. ^ “Essential Oil from Origanum dictamnus”. Planta Med. 53 (1): 107–9. (February 1987). doi:10.1055/s-2006-962640. PMID 17268981. 
  20. ^ Calvo-Irabien, L. M.; Yam-Puc, J. A.; Dzib, G.; Escalante-Erosa, F.; Peña-Rodriguez, L. M. (July 2009). “Effect of Postharvest Drying on the Composition of Mexican Oregano (Lippia graveolens) Essential Oil”. Journal of Herbs, Spices & Medicinal Plants (London, UK: Taylor & Francis) 15 (3): 281–287. doi:10.1080/10496470903379001. ISSN 1540-3580. 
  21. ^ Mockute, D; Bernotiene, G; Judzentiene, A (May 2001). “The essential oil of Origanum vulgare L. ssp. vulgare growing wild in vilnius district (Lithuania)”. Phytochemistry 57 (1): 65–9. doi:10.1016/s0031-9422(00)00474-x. PMID 11336262. 
  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. 
  23. ^ Prashar, A.; Locke, I. C.; Evans, C. S. (2004). “Cytotoxicity of lavender oil and its major components to human skin cells”. Cell Proliferation 37 (3): 221–229. doi:10.1111/j.1365-2184.2004.00307.x. PMID 15144499. 
  24. ^ Umezu, Toyoshi; Nagano, Kimiyo; Ito, Hiroyasu; Kosakai, Kiyomi; Sakaniwa, Misao; Morita, Masatoshi (1 December 2006). “Anticonflict effects of lavender oil and identification of its active constituents”. Pharmacology Biochemistry and Behavior 85 (4): 713–721. doi:10.1016/j.pbb.2006.10.026. http://www.sciencedirect.com/science/article/pii/S0091305706003686 21 February 2017閲覧。. 
  25. ^ Jamshidi, R.; Afzali, Z.; Afzali, D. (February 2009). “Chemical Composition of Hydrodistillation Essential Oil of Rosemary in Different Origins in Iran and Comparison with Other Countries” (PDF). American-Eurasian Journal of Agricultural & Environmental Sciences (Pakistan: IDOSI Publications) 5 (1): 78–81. ISSN 1990-4053. http://www.idosi.org/aejaes/jaes5(1)/13.pdf September 6, 2010閲覧。. 
  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. 
  27. ^ “Essential oil constituents of the spice Cinnamomum tamala (Ham.) Nees & Eberm.”. Flavour and Fragrance Journal 15 (6): 388–390. (2000). doi:10.1002/1099-1026(200011/12)15:6<388::AID-FFJ928>3.0.CO;2-F. 
  28. ^ Leandro, L. M.; Vargas Fde, S; Barbosa, P. C.; Neves, J. K.; Da Silva, J. A.; Da Veiga-Junior, V. F. (2012). “Chemistry and biological activities of terpenoids from copaiba (Copaifera spp.) oleoresins”. Molecules 17 (4): 3866–89. doi:10.3390/molecules17043866. PMID 22466849. 
  29. ^ Sousa, J. P.; Brancalion, A. P.; Souza, A. B.; Turatti, I. C.; Ambrósio, S. R.; Furtado, N. A.; Lopes, N. P.; Bastos, J. K. (Mar 2011). “Validation of a gas chromatographic method to quantify sesquiterpenes in copaiba oils”. J Pharm Biomed Anal 54 (4): 653–9. doi:10.1016/j.jpba.2010.10.006. PMID 21095089. 
  30. ^ http://staff.najah.edu/sites/default/files/Within_plant_distribution_and_emission_of_sesquiterpenes_from_Copaifera_officinalis.pdf
  31. ^ http://www.rain-tree.com/copaiba.htm
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