cubebene

{{Chembox

| Name = Cubebenes

| ImageFileL1 = α-Cubebene.svg

| ImageSizeL1 = 120px

| ImageCaptionL1 = α-Cubebene

| ImageFileR1 = β-Cubebene.svg

| ImageSizeR1 = 120px

| ImageCaptionR1 = β-Cubebene

| IUPACName = {{bulletedlist|(α): (1R,5S,6R,7S,10R)-4,10-Dimethyl-7-propan-2-yltricyclo[4.4.0.0^1,5]dec-3-ene | (β): (1R,5S,6R,7S,10R)-10-Methyl-4-methylidene-7-propan-2-yltricyclo[4.4.0.0^1,5]decane }}

| OtherNames =

| Section1 = {{Chembox Identifiers

| index1_label = (α)

| index2_label = (β)

| CASNo1 = 17699-14-8

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo2 = 13744-15-5

| ChEBI2 = 10363

| ChemSpiderID1 = 24846711

| ChemSpiderID2 = 84031

| KEGG1 = C09647

| KEGG2 = C09648

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII1 = 438H9S5RG9

| PubChem1 = 42608159

| PubChem2 = 93081

| EC_number1 = 605-792-7

| EC_number2 = 604-019-0

| SMILES1 = C[C@@H]1CC[C@H]([C@H]2C13[C@@H]2C(=CC3)C)C(C)C

| SMILES2 = C[C@@H]1CC[C@H]([C@H]2[C@]13[C@@H]2C(=C)CC3)C(C)C

| InChI1=1S/C15H24/c1-9(2)12-6-5-11(4)15-8-7-10(3)13(15)14(12)15/h7,9,11-14H,5-6,8H2,1-4H3/t11-,12+,13-,14-,15?/m1/s1

| InChIKey1 = XUEHVOLRMXNRKQ-PFNKYVCDSA-N

}}

| Section2 = {{Chembox Properties

| C=15|H=24

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

Cubebenes are a pair of chemical compounds, classified as sesquiterpenes, first isolated from Piper cubeba berries, known as cubebs.

The volatile oil from the distillation of cubebs is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor {{Citation | last=Lawless | first=Julia | title=The Illustrated Encyclopedia of Essential Oils: The Complete Guide to the Use of Oils in Aromatherapy and Herbalism | publisher=Element Books | year=1995 | isbn=978-1-85230-721-9 }} consisting of cubebene which comes in two forms, α- and β-cubebene, both with the molecular formula C₁₅H₂₄.{{EB1911 |wstitle=Cubebs |volume=7 |page=607 }} They differ only in the position of a double bond which is endocyclic (part of the five-membered ring) in α-cubebene, but exocyclic in β-cubeαbene.{{cite journal | doi = 10.1016/S0040-4039(00)70179-1 | title = Sesquiterpene hydrocarbons from the oil of cubeb α-cubebene and β-cubebene | journal = Tetrahedron Letters | volume = 7 | issue = 51 | pages = 6365–6370 | year = 1966 | last1 = Ohta | first1 = Yoshimoto | last2 = Sakai | first2 = Tsutomu | last3 = Hirose | first3 = Toshio }}