(-)-α-Gurjunene

Alpha-Gurjunene or (-)-Alpha-Gurjunene, belongs to the class of organic compounds known as 5,10-cycloaromadendrane sesquiterpenoids. These are aromadendrane sesquiterpenoids that arise from the C5-C10 cyclization of the aromadendrane skeleton. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpenoid as it synthesized via isoprene units. Sesquiterpenes are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Alpha-Gurjunene is a neutral, hydrophobic molecule that is insoluble in water. It exists as a colorless clear Liquid and has a woody, balsamic odor. It is used as a perfuming agent. Alpha-gurjunene is found in many plants, essential oils and foods including allspice, bay leaf, carrot seeds, eucalyptus, guava, parsley, black papper, sage and tea tree oil.

ID EC Number Name
KEGG:R09606 4.2.3.72 (2E,6E)-farnesyl-diphosphate diphosphate-lyase [(-)-alpha-gurjunene-forming]
Rhea:RHEA:29508 4.2.3.72 (2E,6E)-farnesyl diphosphate => (−)-α-gurjunene + diphosphate
Rhea:RHEA:29509 4.2.3.72 (−)-α-gurjunene + diphosphate => (2E,6E)-farnesyl diphosphate
Rhea:RHEA:29510 4.2.3.72 (2E,6E)-farnesyl diphosphate <=> (−)-α-gurjunene + diphosphate
BioCyc:RXN-11910 4.2.3.72 FARNESYL-PP --> CPD-12891 + PPI
Rhea:RHEA:29507 [29507] (2E,6E)-farnesyl diphosphate = (-)-alpha-gurjunene + diphosphate