thujopsene

{{Chembox

| ImageFile = Thujopsene.svg

| ImageSize =

| PIN = (1aS,4aS,8aS)-2,4a,8,8-Tetramethyl-1,1a,4,4a,5,6,7,8-octahydrocyclopropa[d]naphthalene

| OtherNames = Sesquichamene; Thujopsen; Widdrene

|Section1={{Chembox Identifiers

| CASNo = 470-40-6

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = E116U47P7N

| PubChem = 442402

| ChEBI = 9578

| ChemSpiderID = 390845

| SMILES = C\2=C(\[C@H]3[C@@]1([C@](CCCC1(C)C)(C)C/2)C3)C

| InChI = 1/C15H24/c1-11-6-9-14(4)8-5-7-13(2,3)15(14)10-12(11)15/h6,12H,5,7-10H2,1-4H3/t12-,14-,15-/m0/s1

| InChIKey = WXQGPFZDVCRBME-QEJZJMRPBP

| StdInChI = 1S/C15H24/c1-11-6-9-14(4)8-5-7-13(2,3)15(14)10-12(11)15/h6,12H,5,7-10H2,1-4H3/t12-,14-,15-/m0/s1

| StdInChIKey = WXQGPFZDVCRBME-QEJZJMRPSA-N

}}

|Section2={{Chembox Properties

| C=15 | H=24

| Appearance =

| Density = 0.936 g/mL (20 °C){{cite web | url = http://www.sigmaaldrich.com/catalog/product/aldrich/89235?lang=en | publisher = Sigma-Aldrich | title = (−)-Thujopsene}}

| MeltingPt =

| BoilingPtC = 258 to 260

| BoilingPt_ref =

| Solubility =

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|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

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Thujopsene is a natural chemical compound, classified as a sesquiterpene, with the molecular formula C15H24.

Thujopsene is found in the essential oil of a variety of conifers,{{cite journal | title = Structure of thujopsene and hinokiic acid from coniferous wood |author1=Erdtman, H. |author2=Norin, T. | journal = Chemistry and Industry | year = 1960 | issue = 22 | pages = 622–623}} in particular Juniperus cedrus and Thujopsis dolabrata in which it comprises around 2.2% of the weight of the heartwood.{{cite journal | last1=Runeburg | first1=Jarl | year=1960 | title=The Chemistry of the Natural Order Cupressales XXX. Constituents of Juniperus cedrus L. | journal=Acta Chemica Scandinavica | volume=14 | pages=1991–1994 | doi=10.3891/acta.chem.scand.14-1991 | last2=Gramstad | first2=Thor | last3=Larsson | first3=Lennart | last4=Dodson | first4=R. M. | doi-access=free }}

Biosynthesis

Thujopsene is biosynthesized from farnesyl pyrophosphate (FPP):{{cite book| author = J. Mann| title = Natural Products: their chemistry and biological significance| isbn = 978-0582060098| display-authors = etal| url-access = registration| url = https://archive.org/details/isbn_9780582060098| year = 1994| publisher = Longman Scientific & Technical}}

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References