1.0 2010-04-08 22:06:24 UTC 2025-11-18 22:57:29 UTC FDB004787 gamma-Elemene Gamma-Elemene, also known as g-elemene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids 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. More formally, gamma-elemene is a cyclohexane substituted at positions 1, 1, 2, and 4 by methyl, vinyl, isopropenyl and isopropylidene groups, respectively. There are four known elemene isomers including α-, β-, γ-, and δ-elemene. The elemenes contribute to the floral aromas of some plants and are used as pheromones by some insects. Gamma-elemene is found in many essential plant oils including wormwood leaf oil, peppermint oil, pepper tree leaf oil, parsley leaf oil, orange peel oil, lime oil, juniper berry oil, hinoki leaf oil, angelica root oil, and angelica seed oil. Gamma-elemene has been shown to exhibit good insecticidal activity against the crop pest Spodoptera litura (tobacco cutworm or cotton leafworm) and could be useful as an eco-friendly biopesticide (PMID:28634795). 1-naphthalenepropionic Acid gamma-Elemene C15H24 204.357 204.187800773 (1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane (1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane CC(C)=C1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,14H,1,4,8-10H2,2-3,5-6H3/t14-,15+/m0/s1 BQSLMQNYHVFRDT-LSDHHAIUSA-N belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Sesquiterpenoids Organic compounds Lipids and lipid-like molecules Prenol lipids Sesquiterpenoids Aliphatic homomonocyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Unsaturated aliphatic hydrocarbons Aliphatic homomonocyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Olefin Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon logp 5.09 ALOGPS logs -4.35 ALOGPS solubility 9.10e-03 g/l ALOGPS logp 4.64 ChemAxon iupac (1S,2S)-1-ethenyl-1-methyl-2-(prop-1-en-2-yl)-4-(propan-2-ylidene)cyclohexane ChemAxon average_mass 204.357 ChemAxon mono_mass 204.187800773 ChemAxon smiles CC(C)=C1CC[C@@](C)(C=C)[C@@H](C1)C(C)=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-7-15(6)9-8-13(11(2)3)10-14(15)12(4)5/h7,14H,1,4,8-10H2,2-3,5-6H3/t14-,15+/m0/s1 ChemAxon inchikey BQSLMQNYHVFRDT-LSDHHAIUSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 69.03 ChemAxon polarizability 25.8 ChemAxon rotatable_bond_count 2 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 103761 Specdb::MsMs 103762 Specdb::MsMs 103763 Specdb::MsMs 169884 Specdb::MsMs 169885 Specdb::MsMs 169886 Specdb::MsMs 3600965 Specdb::MsMs 3600966 Specdb::MsMs 3600967 Specdb::MsMs 3600968 Specdb::MsMs 3600969 Specdb::MsMs 3600970 Specdb::CMs 5803 Caraway Type 1 specific Carum carvi 48032 Cheese Type 2 specific Common oregano Type 1 specific Origanum vulgare 39352 0.0 0.0 0.0 mg/100 g Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 1.75 1.75 1.75 mg/100 g Parsley Type 1 specific Petroselinum crispum 4043 Pot marjoram Type 1 specific Origanum onites 452416 0.01 0.01 0.01 mg/100 g Sweet basil Type 1 specific Ocimum basilicum 39350 1.5 1.5 1.5 mg/100 g Sweet bay Type 1 specific Laurus nobilis 85223 Sweet marjoram Type 1 specific Origanum majorana 268884