Pinocarvone

Chemical compound From Wikipedia, the free encyclopedia

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

Quick facts Names, Identifiers ...
Pinocarvone
Names
IUPAC name
6,6-dimethyl-2-methylidenebicyclo[3.1.1]heptan-3-one
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.045.632 Edit this at Wikidata
EC Number
  • 250-211-9
KEGG
  • 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
  • CC1(C2CC1C(=C)C(=O)C2)C
Properties
C10H14O
Molar mass 150.22 g·mol−1
Hazards
GHS labelling:[1]
GHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazard
Danger
H315, H317, H318, H341
P203, P261, P264, P264+P265, P272, P280, P302+P352, P305+P354+P338, P317, P318, P321, 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).
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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]

References

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