| Revision as of 13:04, 15 November 2010 editEdgar181 (talk | contribs)Extended confirmed users196,325 edits removed incorrect MP - it is an oil at room temp - added reference for data← Previous edit |
Latest revision as of 01:05, 18 November 2024 edit undoSmokefoot (talk | contribs)Autopatrolled, Extended confirmed users, Pending changes reviewers, Rollbackers74,617 edits →Reactions and uses: link repair |
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{{chembox |
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{{chembox |
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|Verifiedfields = changed |
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|Watchedfields = changed |
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| verifiedrevid = 284371473 |
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|verifiedrevid = 396900661 |
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| Name = α-Phellandrene <small>(left)</small> and β-Phellandrene <small>(right)</small> |
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|Name = Phellandrenes |
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| ImageFileL1 = Phellandrene alpha.svg |
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|ImageFileL1 = Phellandrene alpha.svg |
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| ImageSizeL1 = 80px |
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| ImageNameL1 = α-Phellandrene |
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|ImageSizeL1 = 80px |
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|ImageNameL1 = α-Phellandrene |
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| ImageFileR1 = Phellandrene beta.svg |
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|ImageCaptionL1 = α-Phellandrene |
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|ImageFileR1 = Phellandrene beta.svg |
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| ImageSizeR1 = 80px |
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| ImageNameR1 = β-Phellandrene |
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|ImageSizeR1 = 80px |
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|ImageNameR1 = β-Phellandrene |
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|ImageCaptionR1 = β-Phellandrene |
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| IUPACName = α: 2-Methyl-5-(1-methylethyl)-1,3-cyclohexadiene<br />β: 3-Methylene-6-(1-methylethyl)cyclohexene |
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|IUPACNames = (α): 2-Methyl-5-(propan-2-yl)cyclohexa-1,3-diene<br />(β): 3-Methylidene-6-(propan-2-yl)cyclohex-1-ene |
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| Section1 = {{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite}} |
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|index_label = (α) |
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| CASNo = 99-83-2 |
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| CASOther = (α)<br />555-10-2 (β) |
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|index1_label = (β) |
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|index2_label = (−)-(α) |
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| SMILES = α: CC(C)C1CC=C(C)C=C1<br />β: CC(C)C1CCC(=C)C=C1 |
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|index3_label = (+)-(α) |
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}} |
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|index4_label = (−)-(β) |
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| Section2 = {{Chembox Properties |
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|index5_label = (+)-(β) |
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| Reference = <ref>'']'', 12th Edition, '''7340''', '''7341'''</ref> |
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|CASNo_Ref = {{cascite|correct|CAS}} |
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| Appearance = Colorless oil (α and β) |
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|CASNo = 99-83-2 |
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| Formula = C<sub>10</sub>H<sub>16</sub> |
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|CASNo1_Ref = {{cascite|correct|CAS}} |
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| MolarMass = 136.24 g/mol |
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|CASNo1 = 555-10-2 |
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| Density = α: 0.846 g/cm<sup>3</sup><br />β: 0.85 g/cm<sup>3</sup> |
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|CASNo2_Ref = {{cascite|correct|CAS}} |
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| MeltingPt = |
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|CASNo2 = 4221-98-1 |
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| BoilingPt = α: 171-172 °C<br />β: 171-172 °C |
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|CASNo3_Ref = {{cascite|correct|CAS}} |
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| Solubility = Insoluble (α and β) |
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|CASNo3 = 2243-33-6 |
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}} |
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|UNII_Ref = {{fdacite|correct|FDA}} |
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|UNII = 49JV13XE39 |
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|UNII1_Ref = {{fdacite|correct|FDA}} |
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|UNII1 = 2KK225M001 |
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|UNII2_Ref = {{fdacite|correct|FDA}} |
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|UNII2 = 56UV8X65K0 |
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|UNII3_Ref = {{fdacite|correct|FDA}} |
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|UNII3 = E45FS72C5K |
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|PubChem = 7460 |
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|PubChem1 = 11142 |
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|PubChem4 = 443161 |
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|PubChem2 = 442482 |
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|PubChem3 = 443160 |
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|EC_number = 202-792-5 |
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|EC_number1 = 209-081-9 |
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|EC_number2 = 224-167-6 |
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|ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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|ChemSpiderID = 7180 |
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|ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}} |
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|ChemSpiderID1 = 10669 |
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|ChEBI1 = 48741 |
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|ChEBI2 = 301 |
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|ChEBI3 = 367 |
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|ChEBI4 = 129 |
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|ChEBI5 = 53 |
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|KEGG2 = C09875 |
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|KEGG3 = C11391 |
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|KEGG4 = C11392 |
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|KEGG5 = C09877 |
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|SMILES = CC1=CCC(C=C1)C(C)C |
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|SMILES1 = CC(C)C1CCC(=C)C=C1 |
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|SMILES2 = CC1=CC(C=C1)C(C)C |
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|SMILES3 = CC1=CC(C=C1)C(C)C |
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|InChI = 1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3 |
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|InChIKey = OGLDWXZKYODSOB-UHFFFAOYSA-N |
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|InChI1 = 1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,6,8,10H,3,5,7H2,1-2H3 |
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|InChIKey1 = LFJQCDVYDGGFCH-UHFFFAOYSA-N |
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|InChI2=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m1/s1 |
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|InChIKey2 = OGLDWXZKYODSOB-SNVBAGLBSA-N |
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|InChI3 = 1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m0/s1 |
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|InChIKey3 = OGLDWXZKYODSOB-JTQLQIEISA-N |
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}} |
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|Section2={{Chembox Properties |
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|Properties_ref = <ref>'']'', 12th Edition, '''7340''', '''7341'''</ref> |
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|Appearance = Colorless oil (α and β) |
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|Formula = C<sub>10</sub>H<sub>16</sub> |
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|MolarMass = 136.24 g/mol |
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|Density = α: 0.846 g/cm<sup>3</sup><br />β: 0.85 g/cm<sup>3</sup> |
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|BoilingPt = α: 171-172 °C<br />β: 171-172 °C |
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|Solubility = Insoluble (α and β) |
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}} |
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|Section3 = {{Chembox Hazards |
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|GHSPictograms = {{GHS02}}{{GHS08}} |
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|GHSSignalWord = Danger |
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|HPhrases = {{H-phrases|226|304}} |
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|PPhrases = {{P-phrases|210|233|240|241|242|243|280|301+310|303+361+353|331|370+378|403+235|405|501}} |
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}} |
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'''Phellandrene''' is the name for a pair of ]s that have a similar molecular structure and similar chemical properties. α-Phellandrene and β-phellandrene are cyclic ] and are double-bond ]s. 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 ]. |
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'''Phellandrenes''' are ]s with the formula {{chem2|C10H20}}. have a similar molecular structure and similar chemical properties. α-Phellandrene and β-phellandrene are cyclic ] and are double-bond ]s. In α-phellandrene, both double bonds are endocyclic, and in β-phellandrene, one of them is exocyclic. Both are insoluble in water, but ] with ]. |
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==Etymology and occurrence== |
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α-Phellandrene was named after ''Eucalyptus phellandra'', now called '']'', from which it can be isolated.<ref>Jacobs, S.W.L., Pickard, J., ''Plants of New South Wales'', 1981, ISBN 0-7240-1978-2.</ref> It is also a constituent of the ] of '']''.<ref>Boland, D.J., Brophy, J.J., and A.P.N. House, ''Eucalyptus Leaf Oils'', 1991, ISBN 0-909605-69-6.</ref> β-Phellandrene has been isolated from the oil of ] and ] oil. |
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α-Phellandrene was named after ''Eucalyptus phellandra'', now called '']'', from which it can be isolated.<ref>Jacobs, S.W.L., Pickard, J., ''Plants of New South Wales'', 1981, {{ISBN|0-7240-1978-2}}.</ref> It is also a constituent of the ] of '']''.<ref>Boland, D. J., Brophy, J. J., and A. P. N. House, ''Eucalyptus Leaf Oils'', 1991, {{ISBN|0-909605-69-6}}.</ref> β-Phellandrene has been isolated from the oil of ] and ] oil. The main source of β-phellandrene is ].<ref name=KO>{{cite book |doi=10.1002/0471238961.2005181602120504.a01.pub2|chapter=Terpenoids |title=Kirk-Othmer Encyclopedia of Chemical Technology |year=2006 |last1=Sell |first1=Charles S. |isbn=0471238961 }}</ref> |
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β-] is a source of β-phellandrene.<ref name=KO/> |
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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. |
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The alpha phellandrene isomer can form hazardous and explosive peroxides on contact with air at elevated temperature<ref>{{cite book | author= Urben, Peter | title= Bretherick's Handobook of Reactive Chemical Hazards | publisher= Butterworth-Heinemann | year= 2007 | volume= 1 | edition= 7 | page= 1154 }}</ref>. |
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==Reactions and uses== |
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α-Phellandrene undergoes ] to give phellandrene hydrochloride (a cyclohexenyl chloride). Base hydrolysis of this hydrochloride gives ].<ref name=KO/> |
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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. |
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Like other cyclohexadienes, α-phellandrene reacts with ] to give ]. |
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== Biosynthesis == |
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The biosynthesis of phellandrene begins with ] and ] condensing in an ] to form ]. The resultant monoterpene undergoes cyclization to form a menthyl cationic species. A hydride shift then forms an ]ic carbocation. Finally, an ] occurs at one of two positions, yielding either α-phellandrene or β-phellandrene.<ref>{{Cite book |title=Medicinal natural products : a biosynthetic approach|author=Dewick, Paul M. |date=9 March 2009 |isbn=9780470741689 |edition=3rd |location=Chichester, West Sussex, United Kingdom |oclc=259265604}}</ref> |
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] |
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==Safety== |
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The α-phellandrene isomer can form hazardous and explosive peroxides on contact with air at elevated temperatures.<ref>{{cite book | author= Urben, Peter | title= Bretherick's Handobook of Reactive Chemical Hazards | publisher= Butterworth-Heinemann | year= 2007 | volume= 1 | edition= 7 | page= 1154}}</ref> |
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==References== |
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==References== |
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