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'''Bisabolenes''' are a group of closely related natural chemical compounds which are classified as [[sesquiterpene]]s. Bisabolenes 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 |author=Aldrich, J.R.; Numata, H.; Borges, M.; Bin, F.; Waite, G.K.; 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 this 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 = http://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 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 |author=Aldrich, J.R.; Numata, H.; Borges, M.; Bin, F.; Waite, G.K.; 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 = http://link.springer.com/article/10.1007/s00253-015-6641-y}}</ref>


== Uses ==
== Uses ==

Revision as of 01:28, 18 May 2016

Bisabolenes

α-Bisabolene

β-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)
ChemSpider
  • (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 present in the essential oils of a wide variety of plants including cubeb, lemon and oregano. Various derivates also function as pheromones in different insects, such as stink bugs[1] and fruit flies.[2]. It has also been observed to be produced by several fungi, though it's biological role in that group of organisms remains unclear.[3]

Uses

Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds,[4] including hernandulcin, a natural sweetener. β-Bisabolene has a balsamic odor[5] and is approved in Europe as a food additive.

References

  1. ^ 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: 73–79.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ^ Lu, F.; Teal, P.E. (2001). "Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew)". Arch Insect Biochem Physiol. 48 (3): 144–154. doi:10.1002/arch.1067.
  3. ^ 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. Retrieved 2016-02-22.
  4. ^ Bisabolene derived sesquiterpenoid biosynthesis
  5. ^ (−)-β-bisabolene, flavornet.org
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