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14-September-2008 18:38:43 - Caryophyllene Caryophyllene beta-caryophyllene IUPAC name 4,11,11-trimethyl-8-methylene- bicyclo7.2.0undec-4-ene Identifiers CAS number 87-44-5 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 Except where noted otherwise, data are given for materials in their standard state at 25 °C, 100 kPa Infobox references Caryophyllene, 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, the essential oil of hemp Cannabis sativa, and rosemary Rosmarinus oficinalis. 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.1 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.2 Natural sources Cannabis, hemp, marijuana Cannabis sativa Caraway Carum carvi Cloves Syzygium aromaticum Many Ocimum Basil species Oregano Origanum vulgare Pepper Piper nigrum Rosemary Rosmarinus oficinalis True cinnamon Cinnamomum zeylanicum trans-Caryophyllene constitutes about 3.8-37.5% of cannabis flower essential oil.3 Essential oil of cinnamon Cinnamomum zeylanicum contains about 6.9-11.1% beta-caryophyllene.4 References ^ Gertsch J, Leonti M, Raduner S, et al June 2008. Beta-caryophyllene is a dietary cannabinoid. Proc. Natl. Acad. Sci. U.S.A.. doi:10.1073/pnas.0803601105. PMID 18574142. ^ E. J. Corey, Rajat B. Mitra, and Hisashi Uda 1964. Total Synthesis of d,l-Caryophyllene and d,l-Isocaryophyllene. J. Am. Chem. Soc. 86 3: 485-492. doi:10.1021/ja01057a040. ^ Essential oil of Cannabis sativa L. strains. www.internationalhempassociation.org. Retrieved on 2008-07-11. ^ Volatile constituents of essential oils isolated from different parts of cinnamon Cinnamomum zeylanicum Blume. cat.inist.fr. Retrieved on 2008-08-20. External links Some Proof that Marijuana is a Powerful Medicine, Aaron Rowe, Wired Magazine, June 29, 2008 Retrieved from http://en..org/wiki/Caryophyllene Categories: Flavors | Terpenes and terpenoids | Alkenes | Hydrocarbons | Cannabinoids Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch This page was last modified on 22 August 2008, at 20:26
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