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Caryophyllene. noun. car·y·o·phyl·lene. plural -s. : a liquid sesquiterpene C15H24 obtained from various essential oils (as clove oil) as a mixture of stereoisomers distinguished as α-, β-, and γ-caryophyllene compare humulene.
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.
Caryophyllene has been given GRAS (generally regarded as safe) designation by the FDA and is approved by the FDA for use as a food additive, typically for flavoring.
Caryophyllene helps to improve cold tolerance at low ambient temperatures. Wild giant pandas frequently roll in horse manure, which contains beta-caryophyllene/caryophyllene oxide, to inhibit transient receptor potential melastatin 8 (TRPM8), an archetypical cold-activated ion channel of mammals.
There's a good chance that you've crossed paths with caryophyllene right at your table. Its found in a varienty of places other than cannabis. Here is a list.
Just as different cannabinoids have different effects, so do terpenes. These unique attributes contribute to the overall composition of a strain, adding a dimension to each one’s “personality.” Though research is still substantiating caryophyllene's effects and benefits, the following uses are currently being investigated:
Caryophyllene is sometimes used as a flavoring agent in food, given its peppery taste. It is also found in some detergents and topical skin products.
Some also use caryophyllene for medicinal reasons, either as a supplement or as part of their cannabis. While human studies on this are scarce, studies on rodents have found caryophyllene may have pain-relieving properties, reduce anxiety and depression, and could help with treating addiction. In addition, it’s been shown to be an antioxidant, anti-viral, and anti-inflammatory agent, and some studies even suggest it could increase lifespan by reducing gene stress. Preliminary research has found that beta-caryophyllene promotes healthy digestion and may enhance wound healing. Beta-caryophyllene also has a unique ability to bind directly to CB-2 receptors in the endocannabinoid system.
Cultivars (strains) with Caryophyllene Dominance
Cautions
It is important to specify normal concentrations, as some terpenes can cause irritation, allergic reaction, nausea, headache, and/or acute toxic effects at very high doses - but these doses are much higher than you would ever consume in the course of using cannabis products.
Some terpenes can be dermal irritants, so their concentration in topical products needs to be carefully controlled. Guidance from organizations such as the International Fragrance Association shows that safe limits depend both on the type of product and the individual terpene.
The pharmacological hypothesis argues that aromatic compounds such as terpenes affect mood, physiology, and behavior because they interact with the nervous and/or endocrine systems (hormones).
Caryophyllene (/ˌkærioʊˈfɪliːn/), more formally (−)-β-caryophyllene, (BCP), 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),[3] the essential oil of Cannabis sativa, rosemary,[4] and hops.[5] 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, as well as a trans-double bond in a 9-membered ring, both rarities in nature.
β-Caryophyllene acts as a full agonist of the Cannabinoid receptor type 2 (CB2 receptor) in rats.[6] β-Caryophyllene has a binding affinity of Ki = 155nM at the CB2 receptors in mice.[7] β-Caryophyllene has been shown to have anti-inflammatory action linked to its CB2 receptor activity in a study comparing the pain killing effects in mice with and without CB2 receptors with the group of mice without CB2 receptors seeing little benefit compared to the mice with functional CB2 receptors.[6] β-Caryophyllene has the highest cannabinoid activity compared to the ring opened isomer α-caryophyllene which may modulate CB2 activity.[8] To compare binding, Cannabinol (CBN) binds to the CB2 receptors as a partial agonist with an affinity of CB2 Ki = 126.4 nM[9] while Delta-9-Tetrahydrocannabinol binds to the CB2 receptors as a partial agonist with an affinity of Ki = 36nM.[10]
Formula: C15H24
Molar Mass: 204.357 g·mol−1
PubChem CID: 5281515
Density: 0.9052 g/cm3 (17 °C)
Refractive Index: n20/D 1.474(lit.)
FEMA: 2252 | BETA-CARYOPHYLLENE
Flash Point: 205 °F
Melting Point: <25℃
Boiling Point: 262–264 °C (504–507 °F; 535–537 K)[2]
Form: Neat
Optical Activity: [α]23/D 7.5°, neat