Pinocarvone

Pinocarvone is a terpenoid. Structurally, it is a bicyclic ketone.

Pinocarvone

Names
IUPAC name 6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-one
Identifiers
CAS Number	30460-92-5
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28996
ChemSpider	108603
ECHA InfoCard	100.045.632
EC Number	250-211-9
KEGG	C09884
PubChem CID	121719
CompTox Dashboard (EPA)	DTXSID90865544
InChI InChI=1S/C10H14O/c1-6-8-4-7(5-9(6)11)10(8,2)3/h7-8H,1,4-5H2,2-3H3 Key: TZDMGBLPGZXHJI-UHFFFAOYSA-N
SMILES CC1(C2CC1C(=C)C(=O)C2)C
Properties
Chemical formula	C10H14O
Molar mass	150.22 g·mol−1
Hazards
GHS labelling:[1]
Pictograms
Signal word	Danger
Hazard statements	H315, H317, H318, H341
Precautionary statements	P203, P261, P264, P264+P265, P272, P280, P302+P352, P305+P354+P338, P317, P318, P321, P332+P317, 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). Infobox references

Occurrence

hyssop plant

Pinocarvone is an important component in the essential oils of Eucalyptus globulus.^[2] It is also found at a few percent in essential oils of other eucalyptus species.^[3] In several studies, it has been detected as a component of 25% or even 36% in hyssop oil.^[4]

Pinocarvone is also present in the pheromone of the Western Pine Beetle (Dendroctonus brevicomis) along with frontalin, verbenone, and myrtenol.^[5]

Properties and reactions

Under the influence of light or heat, pinocarvone polymerizes by reaction of its double bond to form a resin. Polymerization can also be carried out deliberately, for example by heating the compound in anisole.^[2]