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)
沸点	254-257 °C, 270 K, -177 °F
	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（英語版）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] [[[クローブオイル|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（英語版）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（英語版） (Cinnamomum tamala) [25.3%]^[27]
イランイラン (Cananga odorata) [3.1–10.7%]
コパイバ（英語版）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（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

^ 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.
^ ^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.
^ ^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.
^ ^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.
^ 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. 11 July 2008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 September 6, 2010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 September 6, 2010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 September 6, 2010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 21 February 2017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 September 6, 2010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

[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. 11 July 2008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 September 6, 2010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 September 6, 2010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 September 6, 2010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 21 February 2017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 September 6, 2010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

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[16]

[17]

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[23]

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[31]

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。