Phellandrene

Phellandrenes
α-Phellandrene α-Phellandrene	β-Phellandrene β-Phellandrene
Names
	IUPAC names α: 2-Methyl-5-(1-methylethyl)-1,3-cyclohexadiene; β: 3-Methylene-6-(1-methylethyl)cyclohexene
Identifiers
CAS Number	(α): 99-83-2 ; (β): 555-10-2 ; (−)-(α): 4221-98-1; (+)-(α): 2243-33-6;
3D model (JSmol)	(α): Interactive image; (β): Interactive image; (−)-(α): Interactive image; (+)-(α): Interactive image;
ChEBI	(β): CHEBI:48741; (−)-(α): CHEBI:301; (+)-(α): CHEBI:367; (−)-(β): CHEBI:129; (+)-(β): CHEBI:53;
ChemSpider	(α): 7180 ; (β): 10669 ;
ECHA InfoCard	100.014.121
EC Number	(α): 202-792-5; (β): 209-081-9; (−)-(α): 224-167-6;
KEGG	(−)-(α): C09875; (+)-(α): C11391; (−)-(β): C11392; (+)-(β): C09877;
PubChem CID	(α): 7460; (β): 11142; (−)-(α): 442482; (+)-(α): 443160; (−)-(β): 443161;
UNII	(α): 49JV13XE39 ; (β): 2KK225M001 ; (−)-(α): 56UV8X65K0; (+)-(α): E45FS72C5K;
CompTox Dashboard (EPA)	(α): DTXSID8051673 ;
	InChI (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): InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m1/s1 Key: OGLDWXZKYODSOB-SNVBAGLBSA-N; (+)-(α): InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3/t10-/m0/s1 Key: OGLDWXZKYODSOB-JTQLQIEISA-N;
	SMILES (α): CC1=CCC(C=C1)C(C)C; (β): CC(C)C1CCC(=C)C=C1; (−)-(α): CC1=CC[C@@H](C=C1)C(C)C; (+)-(α): CC1=CC[C@H](C=C1)C(C)C;
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)
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H226, H304
GHS precautionary statements	P210, P233, P240, P241, P242, P243, P280, P301+310, P303+361+353, P331, P370+378, P403+235, P405, P501
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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	Infobox references

Phellandrenes are 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]

Biosynthesis

The biosynthesis of phellandrene begins with dimethylallyl pyrophosphate and isopentenyl pyrophosphate condensing in an S_N1 reaction to form geranyl pyrophosphate. The resultant monoterpene undergoes cyclization to form a menthyl cationic species. A hydride shift then forms an allylic carbocation. Finally, an elimination reaction occurs at one of two positions, yielding either α-phellandrene or β-phellandrene.[5]

gollark: I CLEARLY said `= (maybe)`.

gollark: However, apiohax = P = (maybe) NP = 0 (mod N). Therefore, as rings may be noncommutative, it is the case that the left ideal, 7, is an eigenvalue of the matrix expansion of the general bee formula. By basic applications of previously proven lemmas, it can be shown that this makes apiohax isomorphic to the group (ℤ, +). The implications are obvious.

gollark: If you mean the history, this is now classified.

gollark: ?urban apioform

gollark: As apiohax exists and is known to, you exist.

References

The Merck Index, 12th Edition, 7340, 7341
Jacobs, S.W.L., Pickard, J., Plants of New South Wales, 1981, 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.
Dewick, Paul M. Medicinal natural products : a biosynthetic approach (3rd ed.). Chichester, West Sussex, United Kingdom. ISBN 9780470741689. OCLC 259265604.

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[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] Urben, Peter (2007). Bretherick's Handobook of Reactive Chemical Hazards. 1 (7 ed.). Butterworth-Heinemann. p. 1154.

[5] Dewick, Paul M. Medicinal natural products : a biosynthetic approach (3rd ed.). Chichester, West Sussex, United Kingdom. ISBN 9780470741689. OCLC 259265604.