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Selinene

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From Wikipedia, the free encyclopedia

Selinenes

α-Selinene

β-Selinene

γ-Selinene

δ-Selinene

Names

IUPAC names

α: Eudesma-3,11-diene
β: Eudesma-4(14),11-diene
γ: Eudesma-4(14),7(11)-diene
δ: Eudesma-4,6-diene

Systematic IUPAC name

α: (2R,4aR,8aR)-2-Isopropenyl-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene
β: (4aR,7R,8aS)-7-Isopropenyl-4a-methyl-1-methylenedecahydronaphthalene
γ: (4aR,8aS)-7-Isopropylidene-4a-methyl-1-methylenedecahydronaphthalene
δ: (3R,4aS,5R,8aS)-3-Isopropyl-5,8a-dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalene

Other names

Selina-3,11-diene (α); beta-Eudesmene (β)

Identifiers

CAS Number

473-13-2 (α)^Y
17066-67-0 (β)^Y
515-17-3 (γ)^Y
473-14-3 (δ)^Y

3D model (JSmol)

ChemSpider

9031905 (α)
390838 (β)
8831174 (γ)
23254820 (δ)

PubChem CID

10856614 (α)
442393 (β)
10655819 (γ)

UNII

99ZHA8F274 (α)^Y

InChI

(α): InChI=1/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h6,13-14H,1,5,7-10H2,2-4H3/t13-,14+,15-/m1/s1
Key: OZQAPQSEYFAMCY-QLFBSQMIBC
(β): InChI=1/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h13-14H,1,3,5-10H2,2,4H3/t13-,14+,15-/m1/s1
Key: YOVSPTNQHMDJAG-QLFBSQMIBC
(γ): InChI=1/C15H24/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h14H,3,5-10H2,1-2,4H3/t14-,15+/m0/s1
Key: RMZHSBMIZBMVMN-LSDHHAIUBU
(δ): InChI=1/C15H26/c1-11(2)13-7-9-15(4)8-5-6-12(3)14(15)10-13/h5,8,11-14H,6-7,9-10H2,1-4H3/t12-,13-,14+,15-/m1/s1
Key: LISVWFDKWZILCJ-APIJFGDWBH

SMILES

(α): C\1(=C\CC[C@]2([C@H]/1C[C@H](\C(=C)C)CC2)C)C
(β): C1(=C)\CCC[C@]2([C@H]1C[C@H](\C(=C)C)CC2)C
(γ): C2(=C(/C)C)\CC[C@@]1([C@H](/C(=C)CCC1)C2)C
(δ): C[C@@H]1CC=C[C@]2([C@H]1C[C@@H](CC2)C(C)C)C

Properties

Chemical formula

C₁₅H₂₄

Molar mass

204.357 g·mol⁻¹

Density

α: 0.914 g/cm³ (20 °C)^[1]
β: 0.915 g/cm³ (20 °C)^[2]

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

Infobox references

Chemical compound

Selinenes are a group of closely relatedisomeric chemical compounds which are classified assesquiterpenes. The selinenes all have the molecular formula C₁₅H₂₄ and they have been isolated from a variety of plant sources. α-Selinene and β-selinene are the most common and are two of the principal components of the oil fromcelery seeds.^[3] γ-Selinene and δ-selinene are less common.

References

[edit]

^Ruzicka, L.; Stoll, M. (1923). "Höhere Terpenverbindungen XIV. Zur Kenntnis des Selinens und der Sesquiterpenalkohole des Selleriesamenöls".Helvetica Chimica Acta.6:846–855.doi:10.1002/hlca.19230060192.
^Tyagi, B. S.; Ghatge, B.B.; Bhattacharyya, S.C. (1963). "Terpenoids—XLIII".Tetrahedron.19 (7):1189–1193.doi:10.1016/S0040-4020(01)98579-5.
^Mathew Attokaran (Jan 13, 2011).Natural Food Flavors and Colorants. John Wiley & Sons.ISBN 9780470959114.

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