カリオフィレン

Caryophyllene
	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
PubChem	5281515
ChemSpider	4444848
UNII	BHW853AU9H
ChEBI	CHEBI:10357 ;
ChEMBL	CHEMBL445740
	SMILES C1(=C)\CC/C=C(/CC[C@@H]2[C@@H]1CC2(C)C)C;
	InChI InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1 Key: NPNUFJAVOOONJE-GFUGXAQUSA-N ; InChI=1/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1 Key: NPNUFJAVOOONJE-GFUGXAQUBC;
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。

アサ、ヘンプ、大麻 (Cannabis sativa)[4] [大麻花精油の3.8–37.5%][11]
黒キャラウェイ (Carum nigrum) [7.8%][12]
チョウジノキ (Syzygium aromaticum)[3] [クローブ花精油1.7–19,5%][13][14]
ホップ (Humulus lupulus)[15] [5.1–14.5%][16]
バジル (Ocimum spp.)[17] [5.3–10.5% O. gratissimum; 4.0–19.8% O. micranthum][18]
オレガノ (Origanum vulgare)[19] [4.9–15.7%][20][21]
黒胡椒 (Piper nigrum) [7.29%][22]
ラベンダー (Lavandula angustifolia) [ラベンダーオイルの4.62–7.55%][23][24]
ローズマリー (Rosmarinus officinalis)[5] [0.1–8.3%][25]
セイロンニッケイ (Cinnamomum zeylanicum) [6.9–11.1%][26]
マラバトラム (Cinnamomum tamala) [25.3%][27]
イランイラン (Cananga odorata) [3.1–10.7%]
コパイバ油 (Copaifera spp.)[28][29][30][31]

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

SciFinder Record, CAS Registry Number 87-44-5
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.
“Local anaesthetic activity of beta-caryophyllene”. Farmaco 56 (5–7): 387–9. (2001). doi:10.1016/S0014-827X(01)01092-8. PMID 11482764.
“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.
“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.
Glenn Tinseth, "Hop Aroma and Flavor", January/February 1993, Brewing Techniques. <http://realbeer.com/hops/aroma.html> Accessed July 21, 2010.
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.
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.
Stahl, E; Kunde, R (1973). “Die Leitsubstanzen der Haschisch-Suchhunde”. Kriminalistik: Z Gesamte Kriminal Wiss Prax. 27: 385–389.
http://www.thegoodscentscompany.com/data/rw1023631.html
Mediavilla, Vito. “Essential oil of Cannabis sativa L. strains”. International Hemp Association. 2008年7月11日閲覧。
“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.
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 2010年9月6日閲覧. "The results showed that the essential oils mainly contained about [...] 3.56% β-Caryophyllene"
Clove Essential Oil
“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.
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 2010年9月6日閲覧。.
“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.
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 2010年9月6日閲覧。.
“Essential Oil from Origanum dictamnus”. Planta Med. 53 (1): 107–9. (February 1987). doi:10.1055/s-2006-962640. PMID 17268981.
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.
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.
“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.
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.
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 2017年2月21日閲覧。.
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 2010年9月6日閲覧。.
“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.
“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.
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.
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.
http://staff.najah.edu/sites/default/files/Within_plant_distribution_and_emission_of_sesquiterpenes_from_Copaifera_officinalis.pdf
http://www.rain-tree.com/copaiba.htm

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[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.

[pmid11482764-3] “Local anaesthetic activity of beta-caryophyllene”. Farmaco 56 (5–7): 387–9. (2001). doi:10.1016/S0014-827X(01)01092-8. PMID 11482764.

[pmid18574142-4] “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.

[pmid18670820-5] “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.

[9] Stahl, E; Kunde, R (1973). “Die Leitsubstanzen der Haschisch-Suchhunde”. Kriminalistik: Z Gesamte Kriminal Wiss Prax. 27: 385–389.

[10] ttp://www.thegoodscentscompany.com/data/rw1023631.html

[11] Mediavilla, Vito. “Essential oil of Cannabis sativa L. strains”. International Hemp Association. 2008年7月11日閲覧。

[pmid16390196-12] “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.

[issn19302126-13] 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 2010年9月6日閲覧. "The results showed that the essential oils mainly contained about [...] 3.56% β-Caryophyllene"

[14] Clove Essential Oil

[pmid18775972-15] “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.

[issn02357216-16] 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 2010年9月6日閲覧。.

[pmid18095647-17] “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.

[issn14246376-18] 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 2010年9月6日閲覧。.

[pmid17268981-19] “Essential Oil from Origanum dictamnus”. Planta Med. 53 (1): 107–9. (February 1987). doi:10.1055/s-2006-962640. PMID 17268981.

[issn15403580-20] 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.

[pmid12462618-22] “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 2017年2月21日閲覧。.

[issn19904053-25] 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 2010年9月6日閲覧。.

[Cinnamomum_zeylanicum-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.

[eocs-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] ttp://staff.najah.edu/sites/default/files/Within_plant_distribution_and_emission_of_sesquiterpenes_from_Copaifera_officinalis.pdf

[31] ttp://www.rain-tree.com/copaiba.htm