View source for Cedrene

{{Chembox
| Name = (−)-α-cedrene
| ImageFile = alpha-cedrene skeletal.svg
| ImageSize =
| ImageAlt =
| IUPACName = Cedr-8-ene
| SystematicName = (3''R'',3a''S'',7''S'',8a''S'')-3,6,8,8-Tetramethyl-2,3,4,7,8,8a-hexahydro-1''H''-3a,7-methanoazulene
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 11028-42-5
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo1 = 469-61-4
| CASNo1_Comment = (α)
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 546-28-1
| CASNo2_Comment = (β)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 1M4BF4O9SA
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = 50D4A81G8T
| UNII1_Comment = (α)
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 6QL7ERD5Q1
| UNII2_Comment = (β)
| PubChem = 6431015
| ChemSpiderID = 4936353
| ChEBI = 10216
| KEGG = C09630
| EC_number = 234-257-7
| Beilstein = 2207578
| SMILES = C[C@@H]1CC[C@@H]2[C@]13CC=C([C@H](C3)C2(C)C)C
| 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
| InChIKey = IRAQOCYXUMOFCW-OSFYFWSMBF
| StdInChI = 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
| StdInChIKey = IRAQOCYXUMOFCW-OSFYFWSMSA-N
}}
|Section2={{Chembox Properties
| C=15 | H=24
| Appearance =
| Density = 0.932&nbsp;g/mL at 20&nbsp;°C<ref name="SiAlalpha">{{Aldrich|id=22133|name=(−)-α-Cedrene|accessdate=8 July 2012}}</ref>
| MeltingPt =
| BoilingPt = 261–262&nbsp;°C<ref name="SiAlalpha" />
| Solubility = }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS02}}{{GHS08}}{{GHS09}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|226|304|410}}
| PPhrases = {{P-phrases|210|233|240|241|242|243|273|280|301+310|303+361+353|331|370+378|391|403+235|405|501}}
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
{{Chembox
| Name = (+)-β-cedrene
| ImageFile = beta-cedrene skeletal.svg
| ImageSize =
| ImageAlt =
| IUPACName = Cedr-8(15)-ene
| SystematicName = (3''R'',3a''S'',7''S'',8a''S'')-3,6,8,8-Tetramethyl-6-methylideneoctahydro-1''H''-3a,7-methanoazulene
| OtherNames =
|Section1={{Chembox Identifiers
| CASNo = 546-28-1
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 6QL7ERD5Q1
| PubChem = 11106485
| ChemSpiderID = 9281621
| SMILES = C[C@@H]1CC[C@@H]2[C@]13CCC(=C)[C@H](C3)C2(C)C
| 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
| InChIKey = DYLPEFGBWGEFBB-OSFYFWSMBA
| StdInChI = 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
| StdInChIKey = DYLPEFGBWGEFBB-OSFYFWSMSA-N
}}
|Section2={{Chembox Properties
| C=15 | H=24
| Appearance =
| Density = 0.932 g/mL at 20&nbsp;°C<ref name="SiAlbeta">{{Aldrich|id=22134|name=(+)-β-Cedrene|accessdate=8 July 2012}}</ref>
| MeltingPt =
| BoilingPt = 263–264&nbsp;°C<ref name="SiAlbeta" />
| Solubility = }}
|Section3={{Chembox Hazards
| MainHazards =
| FlashPt =
| AutoignitionPt = }}
}}
'''Cedrene''' is a [[sesquiterpene]] found in the [[essential oil]] of [[Cedar oil|cedar]]. The two [[isomer]]s present in the oil are (−)-α-cedrene<ref>{{Cite journal | last1 = Lee | first1 = H. Y. | last2 = Lee | first2 = S. | last3 = Kim | first3 = D. | last4 = Kim | first4 = B. K. | last5 = Bahn | first5 = J. S. | last6 = Kim | first6 = S. | doi = 10.1016/S0040-4039(98)01680-3 | title = Total synthesis of α-cedrene: A new strategy utilizing ''N''-aziridinylimine radical chemistry | journal = Tetrahedron Letters | volume = 39 | issue = 42 | pages = 7713–7716 | year = 1998 }}</ref><ref>{{Cite journal
| last1 = Takigawa | first1 = H.
| last2 = Kubota | first2 = H.
| last3 = Sonohara | first3 = H.
| last4 = Okuda | first4 = M.
| last5 = Tanaka | first5 = S.
| last6 = Fujikura | first6 = Y.
| last7 = Ito | first7 = S.
| title = Novel allylic oxidation of α-cedrene to ''sec''-cedrenol by a ''Rhodococcus'' strain
| journal = Applied and Environmental Microbiology
| volume = 59
| issue = 5
| pages = 1336–1341
| year = 1993
| doi = 10.1128/aem.59.5.1336-1341.1993
| pmid = 16348930
| pmc = 182086
| bibcode = 1993ApEnM..59.1336T
}}</ref> and (+)-β-cedrene,<ref>{{Cite journal
| last1 = Kerr | first1 = W. J.
| last2 = McLaughlin | first2 = M.
| last3 = Morrison | first3 = A. J.
| last4 = Pauson | first4 = P. L.
| title = 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
| journal = Organic Letters
| volume = 3
| issue = 19
| pages = 2945–2948
| year = 2001
| pmid = 11554814 | doi=10.1021/ol016054a
}}</ref> which differ in the position of a double bond.
==See also==
* [[Cedrol]], another component of cedar oil
* [https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Logic_of_Organic_Synthesis_(Rao)/08%3A_Strategies_in_Cedrene_Synthesis Logic of Organic Synthesis (Rao)]
==References==
{{reflist}}
[[Category:Sesquiterpenes]]
[[Category:Multiple Chemboxes|B]]
{{hydrocarbon-stub}}