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Gurjunene

From Wikipedia, the free encyclopedia
Gurjunene
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
ECHA InfoCard 100.006.996 Edit this at Wikidata
EC Number
  • 207-695-1
KEGG
  • 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/s1
    Key: SPCXZDDGSGTVAW-XIDUGBJDSA-N
  • C[C@@H]1CC[C@@H]2[C@@H](C2(C)C)C3=C(CC[C@H]13)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).

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 (–)-α-gurjunene + diphosphate

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

β-Gurjunene
γ-Gurjunene

References

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  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.