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Gurjunene

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Gurjunene
Names
IUPAC name (1aR,4R,4aR,7bS)-1,1,4,7-Tetramethyl-1a,2,3,4,4a,5,6,7b-octahydrocyclopropaazulene
Other names (-)-α-Gurjunene
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.006.996 Edit this at Wikidata
EC Number
  • 207-695-1
KEGG
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H24/c1-9-6-8-12-14(15(12,3)4)13-10(2)5-7-11(9)13/h9,11-12,14H,5-8H2,1-4H3/t9-,11-,12-,14-/m1/s1Key: SPCXZDDGSGTVAW-XIDUGBJDSA-N
SMILES
  • C1CC2(C2(C)C)C3=C(CC13)C
Properties
Chemical formula C15H24
Molar mass 204.357 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

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. The following reaction that synthesizes gurjunene can be catalyzed by alpha-gurjunene synthase:

(2E,6E)-farnesyl diphosphate ⇌ {\displaystyle \rightleftharpoons } (–)-α-gurjunene + diphosphate

Related compounds

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

β-Gurjuneneγ-Gurjunene

References

  1. "GURJUN BALSAM (GURJUNENE) MD". www.ventos.com. Retrieved 2023-07-20.
  2. PubChem. "alpha-Gurjunene". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-07-20.
  3. Schmidt CO, Bouwmeester HJ, Bülow N, König WA (April 1999). "Isolation, characterization, and mechanistic studies of (-)-α-gurjunene synthase from Solidago canadensis". Archives of Biochemistry and Biophysics. 364 (2): 167–77. doi:10.1006/abbi.1999.1122. PMID 10190971.
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