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Title: Caryophyllene  
Author: World Heritage Encyclopedia
Language: English
Subject: Cannabis flower essential oil, CP 55,940, SR-144,528, N-Arachidonoyl dopamine, JWH-133
Collection: Alkenes, Cannabinoids, Cb2 Receptor Agonists, Flavors, Hydrocarbons, Sesquiterpenes
Publisher: World Heritage Encyclopedia


IUPAC names
Other names
ChemSpider  Y
Jmol-3D images Image
Molar mass 204.36 g·mol−1
Density 0.9052 g/cm3 (17 °C)[1]
Boiling point 254–257 °C (489–495 °F; 527–530 K)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
 Y  (: Y/N?)

Caryophyllene , or (−)-β-caryophyllene, 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 hemp Cannabis sativa,[4] rosemary Rosmarinus oficinalis,[5] and hops.[6] 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, a rarity in nature.

Caryophyllene is one of the chemical compounds that contributes to the spiciness of black pepper. Beta-caryophyllene was shown to be selective agonist of cannabinoid receptor type-2 (CB2) and to exert significant cannabimimetic antiinflammatory effects in mice.[4] Antinociceptive,[7] neuroprotective,[8] anxiolytic and antidepressant [9] and anti-alcoholism [10] activity have been uncovered. Because the widespread plant natural product beta-caryophyllene is an FDA approved food additive and ingested daily with food it is the first dietary cannabinoid. Whether this compound is able to modulate inflammatory processes in humans via the endocannabinoid system is yet unknown. Beta-caryophyllene does not bind to the centrally expressed cannabinoid receptor type-1 (CB1) and therefore does not exert psychotomimetic effects.

The first total synthesis of caryophyllene in 1964 by

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Notes and references

  • Food Chemical Codex[36][37]

Compendial status

The approximate quantity of caryophyllene in the essential oil of each source is given in square brackets ([ ]):

Natural sources

Caryophyllene oxide, in which the olefin of caryophyllene has become an epoxide, is the component responsible for cannabis identification by drug-sniffing dogs[12][13] and is also an approved food flavoring.[14]


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