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Caryophyllene
IUPAC name	4,11,11-trimethyl-8-methylene- bicyclo[7.2.0]undec-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

1. ^ 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. 
2. ^ 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. 
3. ^ "Essential oil of Cannabis sativa L. strains". www.internationalhempassociation.org. Retrieved on 2008-07-11.
4. ^ "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

Wikipedia content modification information:

• This page was last modified on 22 August 2008, at 20:26.

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