Umbellulone

Umbellulone
Names
	IUPAC name 4-Methyl-1-(propan-2-yl)bicyclo[3.1.0]hex-3-en-2-one
	Other names Thujenone; Thujen-2-one; Umbellulon
Identifiers
CAS Number	24545-81-1 ; 546-78-1 (1R,5S) ;
3D model (JSmol)	Interactive image;
ChemSpider	82348;
PubChem CID	91195;
UNII	X5YT6KCX2U ;
CompTox Dashboard (EPA)	DTXSID40871998 ;
	InChI InChI=1S/C10H14O/c1-6(2)10-5-8(10)7(3)4-9(10)11/h4,6,8H,5H2,1-3H3 Key: LTTVJAQLCIHAFV-UHFFFAOYSA-N; InChI=1/C10H14O/c1-6(2)10-5-8(10)7(3)4-9(10)11/h4,6,8H,5H2,1-3H3 Key: LTTVJAQLCIHAFV-UHFFFAOYAU;
	SMILES O=C1\C=C(\C)C2C1(C(C)C)C2;
Properties
Chemical formula	C10H14O
Molar mass	150.221 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Umbellulone is a headache-inducing monoterpene ketone found in the leaves of the tree Umbellularia californica, sometimes known as the "headache tree".^[1]^[2]

It is hypothesized to cause headaches by influencing the trigeminovascular system via TRPA1.^[1]

^ ^a ^b Nassini, R.; Materazzi, S.; Vriens, J.; Prenen, J.; Benemei, S.; De Siena, G.; La Marca, G.; Andrè, E.; Preti, D.; Avonto, C.; Sadofsky, L.; Di Marzo, V.; De Petrocellis, L.; Dussor, G.; Porreca, F.; Taglialatela-Scafati, O.; Appendino, G.; Nilius, B.; Geppetti, P. (2011). "The 'headache tree' via umbellulone and TRPA1 activates the trigeminovascular system". Brain. 135 (Pt 2): 376–390. doi:10.1093/brain/awr272. PMID 22036959.
^ Rachel Ehrenberg (November 3, 2011). "Headache tree is a pain in the brain: Bay laurel swells cranial blood vessels". ScienceNews. Retrieved 2011-11-07.