β‐caryophyllene oxide (BCPO) is an oxidation derivate of the more known sesquiterpene called β‐caryophyllene (BCP). both compounds are notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature. BCPO has a strong wooden odor and is used as cosmetic and food additive.

BCP is a phytocannabinoid with strong affinity to cannabinoid receptor type 2 (CB 2), but not cannabinoid receptor type 1 (CB 1). In opposite, BCP oxidation derivative, BCPO, does not exhibit CB 1/2 binding, thus the mechanism of its action is not related to endocannabinoid system (ECS) machinery. It is known that BCPO alters several key pathways for cancer development, such as mitogen‐activated protein kinase (MAPK), PI3K/AKT/mTOR/S6K1 and STAT3 pathways

BCPO, in which the alkene group of caryophyllene has become an epoxide, is the component responsible for cannabis identification by drug-sniffing dogs.

Caryophyllene oxide