Selinene

Selinenes are a group of closely related isomeric chemical compounds which are classified as sesquiterpenes. 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 from celery seeds.[3] γ-Selinene and δ-selinene are less common.

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
3D model (JSmol)
ChemSpider
UNII
  • (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
  • (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
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 their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

References
  1. 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.
  2. 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.
  3. Mathew Attokaran (Jan 13, 2011). Natural Food Flavors and Colorants. John Wiley & Sons. ISBN 9780470959114.
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