Gurjunene

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
CAS Number	489-40-7;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:61699;
ChemSpider	10219452 ;
ECHA InfoCard	100.006.996
EC Number	207-695-1;
KEGG	C19734;
PubChem CID	15560276;
CompTox Dashboard (EPA)	DTXSID0052126 ;
	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/s1 Key: SPCXZDDGSGTVAW-XIDUGBJDSA-N;
	SMILES C[C@@H]1CC[C@@H]2[C@@H](C2(C)C)C3=C(CC[C@H]13)C;
Properties
Chemical formula	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

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 $\rightleftharpoons$ (–)-α-gurjunene + diphosphate

Related compounds

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

β-Gurjunene

γ-Gurjunene

References

↑ "GURJUN BALSAM (GURJUNENE) MD". www.ventos.com. Retrieved 2023-07-20.
↑ PubChem. "alpha-Gurjunene". pubchem.ncbi.nlm.nih.gov. Retrieved 2023-07-20.
↑ 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.

[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.