Pinocarvone

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:
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

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

Occurrence

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

^ "Pinocarvone". pubchem.ncbi.nlm.nih.gov.
^ ^a ^b Wilhelm Treibs, Harry Schmidt (May 1949), "Über das polymere Pinocarvon", Chemische Berichte, vol. 82, no. 3, pp. 218–224, doi:10.1002/cber.19490820310
^ Jorge A. Pino, Rolando Marbot, Rolando Quert, Humberto García (January 2002), "Study of essential oils of Eucalyptus resinifera Smith, E. tereticornis Smith and Corymbia maculata (Hook.) K. D. Hill & L. A. S. Johnson, grown in Cuba", Flavour and Fragrance Journal, vol. 17, no. 1, pp. 1–4, doi:10.1002/ffj.1026{{citation}}: CS1 maint: multiple names: authors list (link)
^ Hakan Özer, Fikrettin Şahin, Hamdullah Kılıç, Medine Güllüce (January 2005), "Essential oil composition of Hyssopus ofﬁcinalis L. subsp. angustifolius (Bieb.) Arcangeli from Turkey", Flavour and Fragrance Journal, vol. 20, no. 1, pp. 42–44, doi:10.1002/ffj.1421{{citation}}: CS1 maint: multiple names: authors list (link)
^ L.M. Libbey, M.E. Morgan, T.B. Putnam, J.A. Rudinsky (August 1974), "Pheromones released during inter- and intra-sex response of the scolytid beetle Dendroctonus brevicomis", Journal of Insect Physiology, vol. 20, no. 8, pp. 1667–1671, Bibcode:1974JInsP..20.1667L, doi:10.1016/0022-1910(74)90095-X, PMID 4853618{{citation}}: CS1 maint: multiple names: authors list (link)

[1] "Pinocarvone". pubchem.ncbi.nlm.nih.gov.

[:0-2] Wilhelm Treibs, Harry Schmidt (May 1949), "Über das polymere Pinocarvon", Chemische Berichte, vol. 82, no. 3, pp. 218–224, doi:10.1002/cber.19490820310

[3] Jorge A. Pino, Rolando Marbot, Rolando Quert, Humberto García (January 2002), "Study of essential oils of Eucalyptus resinifera Smith, E. tereticornis Smith and Corymbia maculata (Hook.) K. D. Hill & L. A. S. Johnson, grown in Cuba", Flavour and Fragrance Journal, vol. 17, no. 1, pp. 1–4, doi:10.1002/ffj.1026{{citation}}: CS1 maint: multiple names: authors list (link)

[4] Hakan Özer, Fikrettin Şahin, Hamdullah Kılıç, Medine Güllüce (January 2005), "Essential oil composition of Hyssopus ofﬁcinalis L. subsp. angustifolius (Bieb.) Arcangeli from Turkey", Flavour and Fragrance Journal, vol. 20, no. 1, pp. 42–44, doi:10.1002/ffj.1421{{citation}}: CS1 maint: multiple names: authors list (link)

[5] L.M. Libbey, M.E. Morgan, T.B. Putnam, J.A. Rudinsky (August 1974), "Pheromones released during inter- and intra-sex response of the scolytid beetle Dendroctonus brevicomis", Journal of Insect Physiology, vol. 20, no. 8, pp. 1667–1671, Bibcode:1974JInsP..20.1667L, doi:10.1016/0022-1910(74)90095-X, PMID 4853618{{citation}}: CS1 maint: multiple names: authors list (link)

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