Terpene Tuesday: Caryophyllenes
Classification of Caryophyllenes
Beta-caryophyllene, alpha-humulene, caryophyllene oxide, and iso-caryophyllene are all sesquiterpenes or sesquiterpenoids. Each of these compounds relates to one another as two are isomers of beta-caryophyllene (isomer means same type and number of atoms, but different arrangement) and the other is essentially an oxidized form of beta-caryophyllene. However, iso-caryophyllene is relatively unstable and typically found in trace amounts and caryophyllene oxide contributes only to aroma, so they will be omitted from discussion.
It is important to note that alpha-humulene was once called alpha-caryophyllene as it is essentially a ring opened form of beta-caryophyllene, i.e. humulene is monocyclic whereas beta-caryophyllene is bicyclic.
Taste & Aroma of Caryophyllenes
In nature, beta-caryophyllene and its isomers are generally always found together. Both beta-caryophyllene and its isomers are essentially “spicy” in taste. They have a very earthy, bold, almost spicy, clove aroma. They are large components of black pepper, clove, rosemary, and hop oils (in addition to cannabis oils). In pure form, they are a slightly yellow, transparent, oil/liquid.
Effects of Caryophyllene
Beta-caryophyllene and alpha-humulene act as potent agonists (activators) to the endocannabinoid system’s CB2 receptor. The CB2, when activated, reduces the inflammatory response carried out by the immune system as CB2 is rooted in most immune cells throughout the body. An interaction with the CB2 receptor results in down-regulation of the inflammatory response carried out by these immune cells.
Out of the 500+ compounds that are known to be found in cannabis, so far only 4 are known to interact with the CB2 receptor: delta9-THC, delta8-THC, CBN, and caryophyllenes. Beta-caryophyllene and humulene bind to the same active site as THC in the CB2 receptor. It is known that CB2 is not a psychoactive receptor like CB1 as it is primarily found in the peripheral CNS, even though the activation of CB2 is known to be a G-Protein interaction and additionally subjected to allosteric effects. All in all, this makes caryophyllenes a potentially useful anti-inflammatory drug.
It is said that eating beta-caryophyllene can help mitigate the feelings of an overwhelming dose of THC; however, its lack of interaction with the CB1 receptor calls for further investigation of this ‘phenomenon’.
Common Name: BETA – CARYOPHYLLENE
Boiling Point: 266 F (130 C)
= 96.0 % GC | 6753-98-6 | Sigma-Aldrich”>
Common Name: ALPHA – HUMULENE
Boiling Point: 222 F (106 C)