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Removed URL that duplicated identifier. Removed access-date with no URL. Removed parameters. | Use this bot. Report bugs. | Suggested by Spinixster | Category:Chemicals using indexlabels | #UCB_Category 16/831
 
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| index2_label = β
| index2_label = β
| index3_label = γ
| index3_label = γ
| CASNo1_Ref = {{cascite|correct|CAS}}
| CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo3_Ref = {{cascite|correct|CAS}}
| CASNo1 = 17627-44-0
| CASNo1 = 17627-44-0
| CASNo2 = 495-61-4
| CASNo2 = 495-61-4
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| ChemSpiderID2 = 8279897
| ChemSpiderID2 = 8279897
| ChemSpiderID3 = 2298446
| ChemSpiderID3 = 2298446
| UNII1_Ref = {{fdacite|correct|FDA}}
⚫
| UNII1 = 2I1R0087H8
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII3_Ref = {{fdacite|correct|FDA}}
⚫
| UNII1 = SUQ209P6FX
| UNII2 = S19BRC22QA
| UNII2 = S19BRC22QA
| UNII3 = E452K502K0
| 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-
| 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
| 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
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'''Bisabolenes''' are a group of closely related natural chemical compounds which are classified as [[sesquiterpene]]s. 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 oil]]s of a wide variety of plants including [[cubeb]], [[lemon]] and [[oregano]]. Various derivates also function as [[pheromone]]s in different [[insect]]s, such as [[Pentatomidae|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) |url=http://naldc.nal.usda.gov/download/37736/PDF |journal=Zeitschrift für Naturforschung |volume=48C |pages=73–79}}</ref> and [[Tephritidae|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=Arch Insect Biochem Physiol |volume=48 |issue=3 |pages=144–154 |doi=10.1002/arch.1067}}</ref> It has also been observed to be produced by several fungi, though it's 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| accessdate = 2016-02-22| date = 2015| url = https://link.springer.com/article/10.1007/s00253-015-6641-y}}</ref>
'''Bisabolenes''' are a group of closely related natural chemical compounds which are classified as [[sesquiterpene]]s. 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 oil]]s of [[bisabol]], and of a wide variety of other plants including [[cubeb]], [[lemon]], and [[oregano]]. Various derivates also function as [[pheromone]]s in different [[insect]]s, such as [[Pentatomidae|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 [[Tephritidae|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 [[isomer]]s 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|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 bond]]s.


== Uses ==
== 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.
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|date=13 August 2014}}</ref>

== See also ==
* [[Alpha-bisabolene synthase]]
* [[(S)-beta-bisabolene synthase]]
* [[(E)-gamma-bisabolene synthase]]
* [[(Z)-gamma-bisabolene synthase]]


==References==
==References==

Latest revision as of 15:29, 18 October 2024

Bisabolenes

α-Bisabolene

β-Bisabolene

γ-Bisabolene
Names
IUPAC names
(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
Identifiers
3D model (JSmol)
α: 2414203
β: 2044625
γ: 2501191
ChEBI
ChemSpider
KEGG
UNII
  • α: InChI=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-
  • β: InChI=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
  • γ: InChI=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+
  • α: CC1=CCC(/C(C)=C/C/C=C(C)/C)CC1
  • β: CC1=CC[C@@H](C(CC/C=C(C)/C)=C)CC1
  • γ: CC(CC/1)=CCC1=C(C)/CC/C=C(C)/C
Properties
C15H24
Molar mass 204.357 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from farnesyl pyrophosphate (FPP)[1] 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[2] and fruit flies.[3] Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear.[4]

Three isomers are known, α-, β-, and γ-bisabolene,[5][6] which differ by the positions of the double bonds.

Uses

[edit]

Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds,[7] including hernandulcin, a natural sweetener. β-Bisabolene has a balsamic odor[8] 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 bisabolane. [9]

See also

[edit]

References

[edit]
  1. ^ "MetaCyc bisabolene biosynthesis (engineered)". biocyc.org. Retrieved 2018-05-28.
  2. ^ Aldrich, J.R.; Numata, H.; Borges, M.; Bin, F.; Waite, G.K.; Lusby, W.R. (1993). "Artifacts and pheromone blends from Nezara spp. and other stink bug (Heteroptera: Pentatomidae)". Zeitschrift für Naturforschung. 48C (1–2): 73–79. doi:10.1515/znc-1993-1-214. S2CID 40523228.
  3. ^ Lu, F.; Teal, P.E. (2001). "Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew)". Archives of Insect Biochemistry and Physiology. 48 (3): 144–154. doi:10.1002/arch.1067. PMID 11673844.
  4. ^ Spakowicz, Daniel J.; Strobel, Scott A. (2015). "Biosynthesis of hydrocarbons and volatile organic compounds by fungi: bioengineering potential". Applied Microbiology and Biotechnology. 99 (12): 4943–4951. doi:10.1007/s00253-015-6641-y. PMC 4677055. PMID 25957494.
  5. ^ "pubchem/alpha-Bisabolene".
  6. ^ "pubchem/beta-Bisabolene".
  7. ^ Bisabolene derived sesquiterpenoid biosynthesis Archived November 2, 2010, at the Wayback Machine
  8. ^ (−)-β-bisabolene, flavornet.org
  9. ^ "Alternative Diesel Fuel from Biosynthetic Bisabolene". 13 August 2014.
[edit]
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