Phellandrene

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Phellandrenes
α-Phellandrene
β-Phellandrene
Names
IUPAC names
α: 2-Methyl-5-(1-methylethyl)-1,3-cyclohexadiene
β: 3-Methylene-6-(1-methylethyl)cyclohexene
Identifiers
99-83-2 (α) YesY
555-10-2 (β)
ChemSpider 7180 (α)
10669 (β)
Jmol 3D model (α): Interactive image
(β): Interactive image
  • (α): InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3
    Key: OGLDWXZKYODSOB-UHFFFAOYSA-N
  • (β): InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3
    Key: LFJQCDVYDGGFCH-UHFFFAOYSA-N
  • (α): CC1=CCC(C=C1)C(C)C
  • (β): CC(C)C1CCC(=C)C=C1
Properties[1]
C10H16
Molar mass 136.24 g/mol
Appearance Colorless oil (α and β)
Density α: 0.846 g/cm3
β: 0.85 g/cm3
Boiling point α: 171-172 °C
β: 171-172 °C
Insoluble (α and β)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
YesY verify (what is YesYN ?)
Infobox references

Phellandrene is the name for a pair of organic compounds that have a similar molecular structure and similar chemical properties. α-Phellandrene and β-phellandrene are cyclic monoterpenes and are double-bond isomers. In α-phellandrene, both double bonds are endocyclic and in β-phellandrene, one of them is exocyclic. Both are insoluble in water, but miscible with ether.

α-Phellandrene was named after Eucalyptus phellandra, now called Eucalyptus radiata, from which it can be isolated.[2] It is also a constituent of the essential oil of Eucalyptus dives.[3] β-Phellandrene has been isolated from the oil of water fennel and Canada balsam oil.

The phellandrenes are used in fragrances because of their pleasing aromas. The odor of β-phellandrene has been described as peppery-minty and slightly citrusy.

The α-phellandrene isomer can form hazardous and explosive peroxides on contact with air at elevated temperature.[4]

References

  1. The Merck Index, 12th Edition, 7340, 7341
  2. Jacobs, S.W.L., Pickard, J., Plants of New South Wales, 1981, ISBN 0-7240-1978-2.
  3. Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991, ISBN 0-909605-69-6.
  4. Lua error in package.lua at line 80: module 'strict' not found.