Caryophyllene

Caryophyllene
Names
	Preferred IUPAC name (1R,4E,9S)-4,11,11-Trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
	Other names β-Caryophyllene; trans-(1R,9S)-8-Methylene-4,11,11-trimethylbicyclo[7.2.0]undec-4-ene
Identifiers
CAS Number	87-44-5 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:10357 ;
ChEMBL	ChEMBL445740 ;
ChemSpider	4444848 ;
DrugBank	DB16854;
ECHA InfoCard	100.001.588
EC Number	201-746-1;
KEGG	C09629;
PubChem CID	5281515;
UNII	BHW853AU9H ;
CompTox Dashboard (EPA)	DTXSID8024739 ;
	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 Key: NPNUFJAVOOONJE-GFUGXAQUSA-N ; 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	204.357 g·mol−1
Density	0.9052 g/cm3 (17 °C)
Boiling point	262–264 °C (504–507 °F; 535–537 K)
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H304, H317
Precautionary statements	P261, P272, P280, P301+P316, P302+P352, P321, P331, P333+P317, P362+P364, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Caryophyllene (/ˌkærioʊˈfɪliːn/), more formally (−)-β-caryophyllene (BCP), is a natural bicyclic sesquiterpene that occurs widely in nature. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

Names

Preferred IUPAC name (1R,4E,9S)-4,11,11-Trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene
Other names 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 (JSmol)	Interactive image
ChEBI	CHEBI:10357^Y
ChEMBL	ChEMBL445740^Y
ChemSpider	4444848^Y
DrugBank	DB16854
ECHA InfoCard	100.001.588
EC Number	201-746-1
KEGG	C09629
PubChem CID	5281515
UNII	BHW853AU9H^Y
CompTox Dashboard (EPA)	DTXSID8024739
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	204.357 g·mol⁻¹
Density	0.9052 g/cm³ (17 °C)
Boiling point	262–264 °C (504–507 °F; 535–537 K)
Hazards
GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H304, H317
Precautionary statements	P261, P272, P280, P301+P316, P302+P352, P321, P331, P333+P317, P362+P364, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is ^YN ?) Infobox references