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Ocimene

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Ocimene

α-Ocimene

cis-β-Ocimene

trans-β-Ocimene
Names
IUPAC names α: (3E)-3,7-Dimethylocta-1,3,7-triene
cis-β: (3Z)-3,7-Dimethylocta-1,3,6-triene
trans-β: (3E)-3,7-Dimethylocta-1,3,6-triene
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.034.205 Edit this at Wikidata
PubChem CID
UNII
InChI
  • InChI=1S/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,8H,1-2,6-7H2,3-4H3/b10-8+Key: XJPBRODHZKDRCB-CSKARUKUSA-N
  • InChI=1/C10H16/c1-5-10(4)8-6-7-9(2)3/h5,8H,1-2,6-7H2,3-4H3/b10-8+Key: XJPBRODHZKDRCB-CSKARUKUBE
SMILES
  • C=C\C(=C\CCC(=C)C)C
Properties
Chemical formula C10H16
Molar mass 136.24 g/mol
Density 0.800 g/cm
Melting point 50 °C (122 °F; 323 K)
Boiling point mix of isomers: 100 °C at 70 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Ocimenes are a group of isomeric hydrocarbons. The ocimenes are monoterpenes found within a variety of plants and fruits. α-Ocimene and the two β-ocimenes differ in the position of the isolated double bond: it is terminal in the alpha isomer. α-Ocimene is cis-3,7-dimethyl-1,3,7-octatriene. β-Ocimene is trans-3,7-dimethyl-1,3,6-octatriene. β-Ocimene exists in two stereoisomeric forms, cis and trans, with respect to the central double bond. The ocimenes are often found naturally as mixtures of the various forms. The mixture, as well as the pure compounds, are oils with a pleasant odor. They are used in perfumery for their sweet herbal scent, and are believed to act as plant defense and have anti-fungal properties. Like the related acyclic terpene myrcene, ocimenes are unstable in air. Like other terpenes, the ocimenes are nearly insoluble in water, but soluble in common organic solvents.

The name is derived from the plant genus name Ocimum from the Ancient Greek word for basil, ὤκιμον (ṓkimon).

References

  1. "CID 5281553 -- PubChem Compound Summary". Retrieved 2008-02-17.
  2. SCLabs, Beyond Aroma: Terpenes in cannabis Archived 2016-06-15 at the Wayback Machine
  3. Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim. doi:10.1002/14356007.a11_141
  4. Eberhard Breitmaier (22 September 2006). Terpenes: Flavors, Fragrances, Pharmaca, Pheromones. John Wiley & Sons. pp. 11–. ISBN 978-3-527-31786-8. Retrieved 2 August 2013. Acyclic monoterpenoid trienes such as p-myrcene and configurational isomers of p-ocimene are found in the oils of basil (leaves of Ocimum basilicum, Labiatae), bay (leaves of Fimenta acris, Myrtaceae), hops (strobiles of Humulus lupulus, ...
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