Selinene

from Wikipedia, the free encyclopedia

The Selinene (stress on the third syllable: Selin e ne ) form a group of natural substances . They are isomeric unsaturated bicyclic sesquiterpenes .

Representative

The isomeric representatives of the selinenes differ in the positioning of the double bonds in the molecule ( regioisomerism ).

Selinene
Surname α-selinene β-selinene γ-selinene δ-selines
Structural formula α-selinene β-selinene γ-selinene
other names
  • (2 R , 4a R , 8a R ) -2-isopropenyl-4a, 8-dimethyl-1,2,3,4,4a, 5,6,8a-octahydronaphthalene
  • Eudesma 3.11 diene
  • Selina-3,11-diene
  • (4a R , 7 R , 8a S ) -7-isopropenyl-4a-methyl-1-methylenedecahydronaphthalene [(+) - β-selinen]
  • Eudesma-4 (14), 11-dien
  • β-eudesms
 (4a R , 8a S ) -7-Isopropylidene-4a-methyl-1-methylenedecahydronaphthalene (8a R ) -6-isopropyl-4,8a-dimethyl-1,2,3,7,8,8a-hexahydronaphthalene [(+) - δ-selinen]
CAS number 473-13-2 17066-67-0 [(+) - β-selinene] 515-17-3
  • 473-14-3 (unspec.)
  • 28624-28-4 [(+) - δ-selinen]
  • 28624-23-9 [(-) - δ-selinen]
PubChem 10856614 442393 10655819 520383
Molecular formula C 15 H 24
Molar mass 204.36 g mol −1
Physical state liquid
Brief description oil
boiling point 268-272 ° C 121–122 ° C (8 hPa)
density 0.914 g cm −1 0.915 g cm −1
GHS
labeling
no classification available
no classification available
no classification available
no classification available
H and P phrases see above see above see above see above
see above see above see above see above
see above see above see above see above

Occurrence

α-Selinen is part of the essential oil from Indian hemp ( Cannabis sativa , essential hemp oil ). α- and β-selines (along with D - (+) - limonene ) are a main component of celery seed oil . (+) - β-Selinen is found in essential oils of Sedge grass , (-) - β-Selinen in the essential oils of Libanotis transcaucasica and Seseli indicum . γ-selines are found in hops ( Humulus lupulus , hop oil ) alongside α-selines .

Individual evidence

  1. ↑ a b c d e f Entry on Selinene. In: Römpp Online . Georg Thieme Verlag, accessed on January 6, 2017.
  2. ↑ a b L. Ruzicka, M. Stoll: Higher terpene compounds XIV. On the knowledge of selinene and the sesquiterpene alcohols in celery seed oil. In: Helvetica Chimica Acta. 6, 1923, p. 846, doi : 10.1002 / hlca.19230060192 .
  3. ↑ Mathew Attokaran: Natural Food Flavors and Colorants . John Wiley & Sons, 2011, ISBN 978-0-470-95911-4 ( limited preview in Google Book Search).