Caryophyllene, or (-)-β-Caryophyllene, is a naturally occurring bicyclic sesquiterpene, a component of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves),2 hemp essential oil Cannabis sativa,34 rosemary Rosmarinus officinalis,5 and hops.6 It is generally found in admixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene ), an open ring isomer. Caryophyllene is notable for having a cyclobutane ring, a rarity in nature.
Caryophyllene is one of the chemical compounds that contribute to the pungent flavor of black pepper. In a study by Jürg Gertsch et al. from the Swiss Federal Institute of Technology (ETH Zurich), beta-caryophyllene was shown to be a selective agonist of the cannabinoid receptor type 2 (CB 2 ) and to exert significant anti-inflammatory effects in mice.3 Because the widespread plant natural product beta-caryophyllene it is an FDA approved food additive and is ingested with the daily meal which is the first cannabinoid in the diet. Whether this compound is capable of modulating inflammatory processes in humans through the endocannabinoid system is still unknown. Beta-caryophyllene does not bind to the centrally expressed cannabinoid receptor type-1 ( CB 1 ) and therefore does not exert psychomimetic effects.
The first total synthesis of caryophyllene was carried out in 1964 by EJ Corey and was considered one of the classic manifestations of the possibilities of synthetic organic chemistry at the time.