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Caryophyllene



Caryophyllene
IUPAC name 4,11,11-trimethyl-8-methylene-
bicyclo[7.2.0]undec-4-ene
Identifiers
CAS number 87-44-5
Properties
Molecular formula C15H24
Molar mass 204.36 g/mol
Density 0.9052 g/cm3
Boiling point

262-264 °C; 129-130 °C (14 mm Hg)

Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Caryophyllene, or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of some essential oils, especially clove oil and the oil from the stems and flowers of Syzygium aromaticum. 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.

Additional recommended knowledge

Caryophyllene is one of the chemical compounds that contributes to the spiciness 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.[1]

References

  1. ^ E. J. Corey, Rajat B. Mitra, and Hisashi Uda (1964). "Total Synthesis of d,l-Caryophyllene and d,l-Isocaryophyllene". J. Am. Chem. Soc. 86 (3): 485-492.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Caryophyllene". A list of authors is available in Wikipedia.
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