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Phellandrene

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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 diethyl ether.

Phellandrenes

α-Phellandrene

α-Phellandrene

β-Phellandrene

β-Phellandrene

Names

(α): 2-Methyl-5-(propan-2-yl)cyclohexa-1,3-diene
(β): 3-Methylidene-6-(propan-2-yl)cyclohex-1-ene

Identifiers

(α): 99-83-2^Y

(β): 555-10-2^Y

(−)-(α): 4221-98-1^Y

(+)-(α): 2243-33-6^Y

3D model (JSmol)

(α): Interactive image

(β): Interactive image

(−)-(α): Interactive image

(+)-(α): Interactive image

(β): CHEBI:48741

(−)-(α): CHEBI:301

(+)-(α): CHEBI:367

(−)-(β): CHEBI:129

(+)-(β): CHEBI:53

(α): 7180^N

(β): 10669^N

(α): 202-792-5

(β): 209-081-9

(−)-(α): 224-167-6

(−)-(α): C09875

(+)-(α): C11391

(−)-(β): C11392

(+)-(β): C09877

(α): 7460

(β): 11142

(−)-(α): 442482

(+)-(α): 443160

(−)-(β): 443161

(α): 49JV13XE39^Y

(β): 2KK225M001^Y

(−)-(α): 56UV8X65K0^Y

(+)-(α): E45FS72C5K^Y

CompTox Dashboard (EPA)

(α): DTXSID8051673

(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

(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

136.24 g/mol

Appearance

Colorless oil (α and β)

α: 0.846 g/cm³
β: 0.85 g/cm³

α: 171-172 °C
β: 171-172 °C

Solubility in water

Insoluble (α and β)

Hazards

GHS labelling:

Danger

Hazard statements

H226, H304

Precautionary statements

P210, P233, P240, P241, P242, P243, P280, P301+P310, P303+P361+P353, P331, P370+P378, P403+P235, P405, P501

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is ^YN ?)

Infobox references

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 oilofEucalyptus 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]

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. Vol. 1 (7 ed.). Butterworth-Heinemann. p. 1154.

^ Dewick, Paul M. (9 March 2009). Medicinal natural products : a biosynthetic approach (3rd ed.). Chichester, West Sussex, United Kingdom. ISBN 9780470741689. OCLC 259265604.{{cite book}}: CS1 maint: location missing publisher (link)

Retrieved from "https://en.wikipedia.org/w/index.php?title=Phellandrene&oldid=1181362557" Last edited on 22 October 2023, at 16:10

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