Phellandrene
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IUPAC names α: 2-Methyl-5-(1-methylethyl)-1,3-cyclohexadiene β: 3-Methylene-6-(1-methylethyl)cyclohexene | |||
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3D model (JSmol) |
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ChemSpider |
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ECHA InfoCard | 100.014.121 | ||
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| Properties[1] | |||
Chemical formula | 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 | ||
Solubility in water | Insoluble (α and β) | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |||
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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 temperatures.[4]
References
^ The Merck Index, 12th Edition, 7340, 7341
^ Jacobs, S.W.L., Pickard, J., Plants of New South Wales, 1981, .mw-parser-output cite.citationfont-style:inherit.mw-parser-output .citation qquotes:"""""""'""'".mw-parser-output .citation .cs1-lock-free abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-limited a,.mw-parser-output .citation .cs1-lock-registration abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .citation .cs1-lock-subscription abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registrationcolor:#555.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration spanborder-bottom:1px dotted;cursor:help.mw-parser-output .cs1-ws-icon abackground:url("//upload.wikimedia.org/wikipedia/commons/thumb/4/4c/Wikisource-logo.svg/12px-Wikisource-logo.svg.png")no-repeat;background-position:right .1em center.mw-parser-output code.cs1-codecolor:inherit;background:inherit;border:inherit;padding:inherit.mw-parser-output .cs1-hidden-errordisplay:none;font-size:100%.mw-parser-output .cs1-visible-errorfont-size:100%.mw-parser-output .cs1-maintdisplay:none;color:#33aa33;margin-left:0.3em.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-formatfont-size:95%.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-leftpadding-left:0.2em.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-rightpadding-right:0.2em
ISBN 0-7240-1978-2.
^ Boland, D.J., Brophy, J.J., and A.P.N. House, Eucalyptus Leaf Oils, 1991,
ISBN 0-909605-69-6.
^ Urben, Peter (2007). Bretherick's Handobook of Reactive Chemical Hazards. 1 (7 ed.). Butterworth-Heinemann. p. 1154.