{{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. The two isomers 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.

== Uses == Used in various perfumes and fragrances to produce a woody scent.<ref>{{Cite web |last=PubChem |title=Cedrene |url=https://pubchem.ncbi.nlm.nih.gov/compound/Cedrene#section=Use-and-Manufacturing |access-date=2025-03-13 |website=pubchem.ncbi.nlm.nih.gov |language=en}}</ref>

==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}}

{{Terpenoids}}

Category:Sesquiterpenes B

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