Caryophyllene

Chembox new
Name = Caryophyllene
ImageFile = Beta-Caryophyllen.svg
ImageName = beta-caryophyllene
IUPACName = 4,11,11-trimethyl-8-methylene-
bicyclo [7.2.0] undec-4-ene
Section1 = Chembox Identifiers
CASNo = 87-44-5
SMILES =
Section2 = Chembox Properties
Formula = C₁₅H₂₄
MolarMass = 204.36 g/mol
Density = 0.9052 g/cm³
MeltingPt =
BoilingPt = 262-264 °C; 129-130 °C (14 mm Hg)

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.cite journal |author=Gertsch J, Leonti M, Raduner S, "et al" |title=Beta-caryophyllene is a dietary cannabinoid |journal=Proc. Natl. Acad. Sci. U.S.A. |volume= |issue= |pages= |year=2008 |month=June |pmid=18574142 |doi=10.1073/pnas.0803601105 |url=] 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. [cite journal |author=E. J. Corey, Rajat B. Mitra, and Hisashi Uda |title=Total Synthesis of "d","l"-Caryophyllene and "d","l"-Isocaryophyllene |journal=J. Am. Chem. Soc. |year=1964 |volume=86 |issue=3 |pages=485–492 |doi=10.1021/ja01057a040 ]

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. [cite web
url=http://www.internationalhempassociation.org/jiha/jiha4208.html
title=Essential oil of Cannabis sativa L. strains
publisher=www.internationalhempassociation.org
accessdate=2008-07-11
last=
first=]

Essential oil of cinnamon ("Cinnamomum zeylanicum") contains about 6.9–11.1% beta-caryophyllene. [cite web
url=http://cat.inist.fr/?aModele=afficheN&cpsidt=14409152
title=Volatile constituents of essential oils isolated from different parts of cinnamon (Cinnamomum zeylanicum Blume)
publisher=cat.inist.fr
accessdate=2008-08-20
last=
first=]

References

External links

* [http://blog.wired.com/wiredscience/2008/06/proof-that-mari.html "Some Proof that Marijuana is a Powerful Medicine"] , Aaron Rowe, "Wired Magazine", June 29, 2008