| Caryophyllene |  | | | | | IUPAC name | 4,11,11-trimethyl-8-methylene-
bicyclo[7.2.0]undec-4-ene | | Other names | β-Caryophyllene;
trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene | | Identifiers | | CAS number | 87-44-5  Y | | PubChem | 5281515 | | SMILES | C1(=C)\CC/C=C(/CC[C@@H]2[C@@H]1CC2(C)C)C | | 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 | | InChI key | NPNUFJAVOOONJE-GFUGXAQUBC | | ChemSpider ID | 4444848 | | Properties | | Molecular formula | C15H24 | | Molar mass | 204.36 g/mol | | Density | 0.9052 g/cm3 | | Boiling point | 262-264 °C; 129-130 °C (14 mm Hg) |  Y (what is this?) (verify)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | | Infobox references | Caryophyllene (pronounced /ˌkæri.ɵfɪˈliːn/), or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves)[1], the essential oil of hemp Cannabis sativa[2], and rosemary Rosmarinus oficinalis.[3] It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, a rarity in nature. Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. Recently, in a study conducted by Jürg Gertsch et al. from the Swiss Federal Institute of Technology (ETH Zurich), beta-caryophyllene was shown to selectively bind to the cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.[2] Since the widespread plant natural product beta-caryophyllene is an FDA approved food additive and ingested daily with food it is the first dietary cannabinoid. Whether this compound is able to modulate inflammatory processes in humans via the endocannabinoid system is yet unknown. Beta-caryophyllene does not bind to the centrally expressed cannabinoid receptor type-1 (CB1) and therefore does not exert psychomimetic effects. The first total synthesis of caryophyllene in 1964 by E.J. Corey was considered one of the classic demonstrations of the possibilities of synthetic organic chemistry at the time.[4] [edit] Natural sources trans-Caryophyllene constitutes about 3.8–37.5% of cannabis flower essential oil.[12] Essential oil of cinnamon (Cinnamomum zeylanicum) contains about 6.9–11.1% beta-caryophyllene.[10] [edit] Compendial status [edit] Toxicology [edit] Notes & References - ^ a b Ghelardini C, Galeotti N, Di Cesare Mannelli L, Mazzanti G, Bartolini A (2001). "Local anaesthetic activity of beta-caryophyllene". Farmaco 56 (5-7): 387–9. PMID 11482764.
- ^ a b c Gertsch J, Leonti M, Raduner S, et al. (July 2008). "Beta-caryophyllene is a dietary cannabinoid". Proceedings of the National Academy of Sciences of the United States of America 105 (26): 9099–104. doi:10.1073/pnas.0803601105. PMID 18574142.
- ^ a b Ormeño E, Baldy V, Ballini C, Fernandez C (September 2008). "Production and diversity of volatile terpenes from plants on calcareous and siliceous soils: effect of soil nutrients". J. Chem. Ecol. 34 (9): 1219–29. doi:10.1007/s10886-008-9515-2. PMID 18670820.
- ^ Corey EJ, Mitra RB, Uda H (1964). "Total Synthesis of d,l-Caryophyllene and d,l-Isocaryophyllene". Journal of the American Chemical Society 86 (3): 485–492. doi:10.1021/ja01057a040.
- ^ Singh G, Marimuthu P, de Heluani CS, Catalan CA (January 2006). "Antioxidant and biocidal activities of Carum nigrum (seed) essential oil, oleoresin, and their selected components". J. Agric. Food Chem. 54 (1): 174–81. doi:10.1021/jf0518610. PMID 16390196.
- ^ Wang G, Tian L, Aziz N, et al. (November 2008). "Terpene biosynthesis in glandular trichomes of hop". Plant Physiol. 148 (3): 1254–66. doi:10.1104/pp.108.125187. PMID 18775972.
- ^ Zheljazkov VD, Cantrell CL, Tekwani B, Khan SI (January 2008). "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. doi:10.1021/jf0725629. PMID 18095647.
- ^ Harvala C, Menounos P, Argyriadou N (February 1987). "Essential Oil from Origanum dictamnus". Planta Med. 53 (1): 107–9. doi:10.1055/s-2006-962640. PMID 17268981.
- ^ Jirovetz L, Buchbauer G, Ngassoum MB, Geissler M (November 2002). "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. PMID 12462618.
- ^ a b Kaul PN, Bhattacharya AK, Rao BRR, et al. (2003). "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. doi:10.1002/jsfa.1277.
- ^ Ahmed A, Choudhary MI, Farooq A, et al. (2000). "Essential oil constituents of the spice Cinnamomum tamala (Ham.) Nees & Eberm.". Flavour and Fragrance Journal 15 (6): 388–390. doi:10.1002/1099-1026(200011/12)15:6<388::AID-FFJ928>3.0.CO;2-F.
- ^ Mediavilla, Vito; Simon Steinemann. "Essential oil of Cannabis sativa L. strains". International Hemp Association. http://www.internationalhempassociation.org/jiha/jiha4208.html. Retrieved 11 July 2008.
- ^ The United States Pharmacopeial Convention. "Revisions to FCC, First Supplement". http://www.usp.org/fcc/FCC61SBallotResultsWebPostingReport01.html. Retrieved 29 June 2009.
- ^ Therapeutic Goods Administration. "Chemical substances". http://www.tga.gov.au/docs/pdf/aan/aanchem.pdf. Retrieved 29 June 2009.
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