Longifolene

(+)-Longifolene
Names
	IUPAC name (1R,2S,7S,9S)- 3,3,7-trimethyl- 8-methylenetricyclo- [5.4.0.02,9]undecane
Identifiers
CAS Number	(+): 475-20-7 ; (−): 16846-09-6;
3D model (JSmol)	(+): Interactive image; (−): Interactive image;
Beilstein Reference	5731712 2044263 4663756
ChEBI	(+): CHEBI:49282 ; (−): CHEBI:49286;
ChemSpider	(+): 16739255 ; (−): 1013315;
ECHA InfoCard	100.006.812
EC Number	(+): 207-491-2;
PubChem CID	(+): 1796220; (−): 1201520;
UNII	(+): 3YXH7YY8WM;
CompTox Dashboard (EPA)	(+): DTXSID9047045 ;
	InChI InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,15-/m1/s1 Key: PDSNLYSELAIEBU-GUIRCDHDSA-N ;
	SMILES (+): C[C@]12CCCC([C@@H]3[C@H]1CC[C@@H]3C2=C)(C)C; (−): C[C@@]12CCCC([C@H]3[C@@H]1CC[C@H]3C2=C)(C)C;
Properties
Chemical formula	C15H24
Molar mass	204.36 g/mol
Density	0.928 g/cm3
Boiling point	254 °C (489 °F; 527 K) (706 mm Hg)
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H304, H317, H410
Precautionary statements	P261, P272, P273, P280, P301+P310, P302+P352, P321, P331, P333+P313, P363, P391, 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

Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated,^[1] Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts.

Longifolene is also one of two most abundant aroma constituents of lapsang souchong tea, because the tea is smoked over pinewood fires.^[2]

^ Naffa, P.; Ourisson, G. Bulletin de la Société chimique de France, 1954, 1410.
^ Shan-Shan Yao； Wen-Fei Guo； YI Lu； Yuan-Xun Jiang, "Flavor Characteristics of Lapsang Souchong and Smoked Lapsang Souchong,a Special Chinese Black Tea with Pine Smoking Process", Journal of Agricultural and Food Chemistry, Vol. 53, No.22, (2005)^{[permanent dead link]}

[1] Naffa, P.; Ourisson, G. Bulletin de la Société chimique de France, 1954, 1410.

[2] Shan-Shan Yao； Wen-Fei Guo； YI Lu； Yuan-Xun Jiang, "Flavor Characteristics of Lapsang Souchong and Smoked Lapsang Souchong,a Special Chinese Black Tea with Pine Smoking Process", Journal of Agricultural and Food Chemistry, Vol. 53, No.22, (2005)^{[permanent dead link]}

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