bisabolene

{{Chembox

| Name= Bisabolenes

| ImageFile = bisabolene-alpha.svg

| ImageSize =

| ImageCaption = α-Bisabolene

| ImageFile1 = bisabolene-beta.svg

| ImageSize1 =

| ImageCaption1 = β-Bisabolene

| ImageFile3 = bisabolene-gamma.svg

| ImageSize3 =

| ImageCaption3 = γ-Bisabolene

| IUPACName = (α): (E)-1-Methyl-4-(6-methylhepta-2,5-dien-2-yl)cyclohex-1-ene
(β): (S)-1-Methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene
(γ): (Z)-1-Methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene

| PIN =

| OtherNames =

|Section1={{Chembox Identifiers

| index1_label = α

| index2_label = β

| index3_label = γ

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

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo3_Ref = {{cascite|correct|CAS}}

| CASNo1 = 17627-44-0

| CASNo2 = 495-61-4

| CASNo3 = 495-62-5

| PubChem1 = 5352653

| PubChem2 = 10104370

| PubChem3 = 3033866

| ChemSpiderID1 = 4509521

| ChemSpiderID2 = 8279897

| ChemSpiderID3 = 2298446

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

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII3_Ref = {{fdacite|correct|FDA}}

| UNII1 = SUQ209P6FX

| UNII2 = S19BRC22QA

| UNII3 = E6941S3U3Q

| InChI1 = 1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6-8,15H,5,9-11H2,1-4H3/b14-7-

| InChI2 = 1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m1/s1

| InChI3 = 1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14+

| SMILES1 = CC1=CCC(/C(C)=C/C/C=C(C)/C)CC1

| SMILES2 = CC1=CC[C@@H](C(CC/C=C(C)/C)=C)CC1

| SMILES3 = CC(CC/1)=CCC1=C(C)/CC/C=C(C)/C

| ChEBI1 = 49244

| ChEBI2 = 49263

| ChEBI3 = 49237

| KEGG2 = C16775

| Beilstein = α: 2414203
β: 2044625
γ: 2501191

}}

|Section2={{Chembox Properties

| C=15 | H=24

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility = }}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt = }}

}}

Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from farnesyl pyrophosphate (FPP){{Cite web|url=https://biocyc.org/META/NEW-IMAGE?type=PATHWAY&object=PWY-7102|title=MetaCyc bisabolene biosynthesis (engineered)|website=biocyc.org|access-date=2018-05-28}} and are present in the essential oils of bisabol, and of a wide variety of other plants including cubeb, lemon, and oregano. Various derivates also function as pheromones in different insects, such as stink bugs{{cite journal |author1=Aldrich, J.R. |author2=Numata, H. |author3=Borges, M. |author4=Bin, F. |author5=Waite, G.K. |author6=Lusby, W.R. |year=1993 |title=Artifacts and pheromone blends from Nezara spp. and other stink bug (Heteroptera: Pentatomidae) |journal=Zeitschrift für Naturforschung |volume=48C |issue=1–2 |pages=73–79 |doi=10.1515/znc-1993-1-214 |s2cid=40523228 |doi-access=free }} and fruit flies.{{cite journal |last1=Lu |first1=F. |last2=Teal |first2=P.E. |year=2001 |title=Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew) |journal=Archives of Insect Biochemistry and Physiology |volume=48 |issue=3 |pages=144–154 |doi=10.1002/arch.1067|pmid=11673844 }} Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear.{{Cite journal| volume = 99| issue = 12| pages = 4943–4951| last1 = Spakowicz| first1 = Daniel J.| last2 = Strobel| first2 = Scott A.| title = Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential| journal = Applied Microbiology and Biotechnology| date = 2015| doi = 10.1007/s00253-015-6641-y| pmid = 25957494| pmc = 4677055}}

Three isomers are known, α-, β-, and γ-bisabolene,{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/_Z_-alpha-Bisabolene#section=Top|title=pubchem/alpha-Bisabolene}}{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/beta-Bisabolene|title=pubchem/beta-Bisabolene}} which differ by the positions of the double bonds.