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.^[1]^[2] The following reaction that synthesizes gurjunene can be catalyzed by alpha-gurjunene synthase:^[3]

(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.

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