Caryophyllene

Caryophyllene

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
CAS Number	87-44-5 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:10357 Y
ChEMBL	ChEMBL445740 Y
ChemSpider	4444848 Y
ECHA InfoCard	100.001.588
PubChem	5281515
UNII	BHW853AU9H Y
InChI InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1 Y Key: NPNUFJAVOOONJE-GFUGXAQUSA-N Y InChI=1/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1 Key: NPNUFJAVOOONJE-GFUGXAQUBC
SMILES C1(=C)\CC/C=C(/CC[C@@H]2[C@@H]1CC2(C)C)C
Properties
Chemical formula	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).
Y  (what is YN ?)
Infobox references

Caryophyllene /ˌkærioʊfɪˈliːn/, 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.