{{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<br>(β): (''S'')-1-Methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene<br>(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<br/>β: 2044625<br/>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)<ref>{{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}}</ref> 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<ref>{{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 }}</ref> and fruit flies.<ref>{{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 }}</ref> Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear.<ref>{{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}}</ref>
Three isomers are known, α-, β-, and γ-bisabolene,<ref name=pubchem>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/_Z_-alpha-Bisabolene#section=Top|archive-url=https://web.archive.org/web/20190203143713/https://pubchem.ncbi.nlm.nih.gov/compound/_Z_-alpha-Bisabolene#section=Top|url-status=dead|archive-date=February 3, 2019|title=pubchem/alpha-Bisabolene}}</ref><ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/beta-Bisabolene|title=pubchem/beta-Bisabolene}}</ref> which differ by the positions of the double bonds.
== Uses == Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds,<ref>[http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/terp/bisabo.html Bisabolene derived sesquiterpenoid biosynthesis] {{webarchive |url=https://web.archive.org/web/20101102132046/http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/terp/bisabo.html |date=November 2, 2010 }}</ref> including hernandulcin, a natural sweetener. β-Bisabolene has a balsamic odor<ref>[http://www.flavornet.org/info/495-61-4.html (−)-β-bisabolene], flavornet.org</ref> and is approved in Europe as a food additive.
Bisabolene has been identified as a biologically producible precursor to a diesel fuel alternative and/or cold weather additive bisabol''ane''. <ref>{{Cite web |url=https://ipo.lbl.gov/lbnl2837/ |title=Alternative Diesel Fuel from Biosynthetic Bisabolene |work=Intellectual Property Office |date=13 August 2014 |author1=Erik |access-date=18 June 2020 |archive-date=19 July 2024 |archive-url=https://web.archive.org/web/20240719192154/https://ipo.lbl.gov/lbnl2837/ |url-status=dead }}</ref>
== See also == * Alpha-bisabolene synthase * (S)-beta-bisabolene synthase * (E)-gamma-bisabolene synthase * (Z)-gamma-bisabolene synthase
==References== {{reflist}}
==External links== * [http://webbook.nist.gov/cgi/cbook.cgi?ID=495-61-4 Beta-bisabolene], NIST Chemistry WebBook listing
Category:Sesquiterpenes Category:Hydrocarbons Category:Cyclohexenes