Chemistry:Gurjunene

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Gurjunene
Alpha-gurjunene.svg
Names
IUPAC name
(1aR,4R,4aR,7bS)-1,1,4,7-Tetramethyl-1a,2,3,4,4a,5,6,7b-octahydrocyclopropa[e]azulene
Other names
(-)-α-Gurjunene
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
EC Number
  • 207-695-1
KEGG
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).
Infobox references
Tracking categories (test):

Gurjunene, also known as (-)-α-gurjunene, is a natural carbotricyclic sesquiterpene that is most commonly found in gurjun balsam, an essential oil compound extracted from plants of the genus Dipterocarpus.[1][2] The following reaction that synthesizes gurjunene can be catalyzed by alpha-gurjunene synthase:[3]

(2E,6E)-farnesyl diphosphate [math]\displaystyle{ \rightleftharpoons }[/math] (–)-α-gurjunene + diphosphate

Related compounds

Several related compounds are known, including β-gurjunene and γ-gurjunene.

β-Gurjunene
γ-Gurjunene

References

  1. "GURJUN BALSAM (GURJUNENE) MD". https://www.ventos.com/index.php/en/producto/8587. 
  2. PubChem. "alpha-Gurjunene" (in en). https://pubchem.ncbi.nlm.nih.gov/compound/15560276. 
  3. "Isolation, characterization, and mechanistic studies of (-)-α-gurjunene synthase from Solidago canadensis". Archives of Biochemistry and Biophysics 364 (2): 167–77. April 1999. doi:10.1006/abbi.1999.1122. PMID 10190971.