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Caryophyllene

Caryophyllene
Beta-Caryophyllen.svg
Names
Preferred IUPAC name
(1R,4E,9S)-4,11,11-Trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Other names
(1R,9S,E)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene
β-Caryophyllene
trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
Identifiers
87-44-5 YesY
3D model (Jmol) Interactive image
ChEBI CHEBI:10357 YesY
ChEMBL ChEMBL445740 YesY
ChemSpider 4444848 YesY
ECHA InfoCard 100.001.588
PubChem 5281515
UNII BHW853AU9H YesY
Properties
C15H24
Molar mass 204.36 g·mol−1
Density 0.9052 g/cm3 (17 °C)
Boiling point 254–257 °C (489–495 °F; 527–530 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY  (what is YesYN ?)
Infobox references

Caryophyllene /ˌkærifɪˈln/, 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), the essential oil of Cannabis sativa,rosemary, 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 notable for having a cyclobutane ring, as well as a trans-double bond in an 8-membered ring, both rarities in nature.

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 one of the chemical compounds that contributes to the spiciness of black pepper.

14-Hydroxycaryophyllene oxide (C15H24O2) was isolated from the urine of rabbits treated with (-)-caryophyllene (C15H24). The x-ray crystal structure of 14-hydroxycaryophyllene (as its acetate derivative) has been reported.

The metabolism of caryophyllen progresses through (-)-caryophyllene oxide (C15H24O) since the latter compound also afforded 14-hydroxycaryophyllene (C15H24O) as a metabolite.


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Wikipedia

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