Cedrene

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(−)-α-cedrene
Names
IUPAC name
Cedr-8-ene
Systematic IUPAC name
(3R,3aS,7S,8aS)-3,6,8,8-Tetramethyl-2,3,4,7,8,8a-hexahydro-1H-3a,7-methanoazulene
Identifiers
3D model (JSmol)
2207578
ChEBI
ChemSpider
ECHA InfoCard 100.031.131 Edit this at Wikidata
EC Number
  • 234-257-7
KEGG
UNII
  • InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1
    Key: IRAQOCYXUMOFCW-OSFYFWSMSA-N
  • InChI=1/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h7,11-13H,5-6,8-9H2,1-4H3/t11-,12+,13+,15+/m1/s1
    Key: IRAQOCYXUMOFCW-OSFYFWSMBF
  • C[C@@H]1CC[C@@H]2[C@]13CC=C([C@H](C3)C2(C)C)C
Properties
C15H24
Molar mass 204.357 g·mol−1
Density 0.932 g/mL at 20 °C[1]
Boiling point 261–262 °C[1]
Hazards
GHS labelling:
GHS02: FlammableGHS08: Health hazardGHS09: Environmental hazard
Danger
H226, H304, H410
P210, P233, P240, P241, P242, P243, P273, P280, P301+P310, P303+P361+P353, P331, P370+P378, P391, P403+P235, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
(+)-β-cedrene
Names
IUPAC name
Cedr-8(15)-ene
Systematic IUPAC name
(3R,3aS,7S,8aS)-3,6,8,8-Tetramethyl-6-methylideneoctahydro-1H-3a,7-methanoazulene
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.031.131 Edit this at Wikidata
UNII
  • InChI=1S/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h11-13H,1,5-9H2,2-4H3/t11-,12+,13+,15+/m1/s1
    Key: DYLPEFGBWGEFBB-OSFYFWSMSA-N
  • InChI=1/C15H24/c1-10-7-8-15-9-12(10)14(3,4)13(15)6-5-11(15)2/h11-13H,1,5-9H2,2-4H3/t11-,12+,13+,15+/m1/s1
    Key: DYLPEFGBWGEFBB-OSFYFWSMBA
  • C[C@@H]1CC[C@@H]2[C@]13CCC(=C)[C@H](C3)C2(C)C
Properties
C15H24
Molar mass 204.357 g·mol−1
Density 0.932 g/mL at 20 °C[2]
Boiling point 263–264 °C[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Cedrene is a sesquiterpene found in the essential oil of cedar. The two isomers present in the oil are (−)-α-cedrene[3][4] and (+)-β-cedrene,[5] which differ in the position of a double bond.

See also

  • Cedrol, another component of cedar oil

References

  1. ^ a b Sigma-Aldrich Co., (−)-α-Cedrene. Retrieved on 8 July 2012.
  2. ^ a b Sigma-Aldrich Co., (+)-β-Cedrene. Retrieved on 8 July 2012.
  3. ^ Lee, H. Y.; Lee, S.; Kim, D.; Kim, B. K.; Bahn, J. S.; Kim, S. (1998). "Total synthesis of α-cedrene: A new strategy utilizing N-aziridinylimine radical chemistry". Tetrahedron Letters. 39 (42): 7713–7716. doi:10.1016/S0040-4039(98)01680-3.
  4. ^ Takigawa, H.; Kubota, H.; Sonohara, H.; Okuda, M.; Tanaka, S.; Fujikura, Y.; Ito, S. (1993). "Novel allylic oxidation of α-cedrene to sec-cedrenol by a Rhodococcus strain". Applied and Environmental Microbiology. 59 (5): 1336–1341. Bibcode:1993ApEnM..59.1336T. doi:10.1128/aem.59.5.1336-1341.1993. PMC 182086. PMID 16348930.
  5. ^ Kerr, W. J.; McLaughlin, M.; Morrison, A. J.; Pauson, P. L. (2001). "Formal total synthesis of (±)-α- and β-cedrene by preparation of cedrone. Construction of the tricyclic carbon skeleton by the use of a highly efficient intramolecular Khand annulation". Organic Letters. 3 (19): 2945–2948. doi:10.1021/ol016054a. PMID 11554814.
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