1.0 2010-04-08 22:06:00 UTC 2025-11-18 22:54:15 UTC FDB003887 (E)-alpha-Bergamotene α-cis-bergamotene belongs to the class of organic compounds known as bicyclic sesquiterpenoids. These are sesquiterpenoids containing exactly two rings, which are fused together. It is formally classified as a polycyclic hydrocarbon although it is biochemically a sesquiterpene as it is 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-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496, 17710406). 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. There are four known Bergamotene isomers including α-cis-, α-trans-, β-cis- and β-trans-bergamotene. α-cis-Bergamotene is found in the oils of carrot, bergamot, lime, citron, cottonseed, and kumquat. Isomers of bergamotene have a function as pheromones for some insect species. Evidence suggests that plants under attack by herbivore insects are able to release specific amounts of bergamotene to attract natural enemies of the herbivores, using these sesquiterpenes as a defense mechanism (PMID: 16418295). C15H24 204.3511 204.187800768 (1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene (1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene CC(C)=CCC[C@@]1(C)[C@H]2C[C@@H]1C(C)=CC2 InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m1/s1 YMBFCQPIMVLNIU-KFWWJZLASA-N belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Bicyclic monoterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Monoterpenoids Aliphatic homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Bicyclic monoterpenoid Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Pinane monoterpenoid Polycyclic hydrocarbon Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 5.91 ALOGPS logs -4.48 ALOGPS solubility 6.82e-03 g/l ALOGPS logp 4.46 ChemAxon iupac (1R,5R,6S)-2,6-dimethyl-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]hept-2-ene ChemAxon average_mass 204.3511 ChemAxon mono_mass 204.187800768 ChemAxon smiles CC(C)=CCC[C@@]1(C)[C@H]2C[C@@H]1C(C)=CC2 ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-11(2)6-5-9-15(4)13-8-7-12(3)14(15)10-13/h6-7,13-14H,5,8-10H2,1-4H3/t13-,14-,15+/m1/s1 ChemAxon inchikey YMBFCQPIMVLNIU-KFWWJZLASA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 68.52 ChemAxon polarizability 26.58 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 104874 Specdb::MsMs 104875 Specdb::MsMs 104876 Specdb::MsMs 171237 Specdb::MsMs 171238 Specdb::MsMs 171239 Specdb::MsMs 3599579 Specdb::MsMs 3599580 Specdb::MsMs 3599581 Specdb::MsMs 3600416 Specdb::MsMs 3600417 Specdb::MsMs 3600418 Anise Type 1 specific Pimpinella anisum 271192 Cumin Type 1 specific Cuminum cyminum 52462 Lime Type 1 specific Citrus aurantiifolia 159033 Lovage Type 1 specific Levisticum officinale 48042 6.85 6.85 6.85 mg/100 g Pepper (Spice) Type 1 specific Piper nigrum 13216 Star anise Type 1 specific Illicium verum 124778 8.05 8.05 8.05 mg/100 g Sweet basil Type 1 specific Ocimum basilicum 39350 7.5 7.5 7.5 mg/100 g Wild celery Type 1 specific Apium graveolens 4045