Caryophyllene (Molecule of the Month for December 2020)
Cloves, (−)-β-caryophyllene,
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), the essential oil of Cannabis sativa, rosemary, black pepper, lavender, and hops. 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 one of the chemical compounds that contributes to the aroma of black pepper.
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 is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.
Formal Chemical Name (IUPAC)
(1R,9S,Z)-4,11,11-trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
References
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Caryophyllene structure
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C15 H24
Update by Karl Harrison
(Molecule of the Month for
December 2020
)
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