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Best known for its spicy and peppery note, caryophyllene is also found in black pepper, cinnamon, cloves, and spices like oregano, basil, and rosemary. Beta-caryophyllene binds to Cannabinoid Type-2 (CB2) receptors, which makes it an ingredient in anti-inflammatory topicals and creams. Caryophyllene is the only terpene that binds to cannabinoid receptors. Besides its analgesic and anti-anxiety properties, some studies have found that caryophyllene has some very promising properties when it comes to alcoholism rehabilitation. A group of scientists performed research on mice and found that this terpene reduces voluntary intake of alcohol. They even recommended caryophyllene for treating alcohol withdrawal symptoms.
Caryophyllene (/ˌkærioʊˈfɪliːn/), more formally (−)-β-caryophyllene (BCP), is a natural bicyclic sesquiterpene that occurs widely in nature. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.
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Names | |
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Preferred IUPAC name
(1R,4E,9S)-4,11,11-Trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene | |
Other names
β-Caryophyllene
trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene | |
Identifiers | |
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3D model (JSmol)
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ChEBI | |
ChEMBL | |
ChemSpider |
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DrugBank | |
ECHA InfoCard | 100.001.588 ![]() |
EC Number |
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KEGG | |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C15H24 | |
Molar mass | 204.357 g·mol−1 |
Density | 0.9052 g/cm3 (17 °C) |
Boiling point | 262–264 °C (504–507 °F; 535–537 K) |
Hazards | |
GHS labelling:[1] | |
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Warning | |
H304, H317 | |
P261, P272, P280, P301+P316, P302+P352, P321, P331, P333+P317, P362+P364, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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English
Noun
caryophyllene (plural caryophyllenes)
- (organic chemistry) A sesquiterpene (containing a cyclobutane ring) found in the essential oils of several plants such as clove and pepper