1.0 2010-04-08 22:06:51 UTC 2019-11-26 03:00:46 UTC FDB005805 Longifolene Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts . (+)-longifolen (+)-longifolene (+)-longofolene α-longifolene 1,4-Methanoazulene, decahydro-4,8,8-trimethyl-9-methylene- 1,4-Methanoazulene, Junipen 4,8,8-trimethyl-9-methylidenedecahydro-1,4-methanoazulene D-longifolene Junipen Junipene Kuromatsuen Kuromatsuene Longifolen Longifolene Longifolene (=junipene) C15H24 204.357 204.187800773 3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0²,⁹]undecane longifolene 475-20-7 CC12CCCC(C)(C)C3C(CCC13)C2=C InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3 PDSNLYSELAIEBU-UHFFFAOYSA-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 homopolycyclic compounds Branched unsaturated hydrocarbons Cyclic olefins Polycyclic hydrocarbons Unsaturated aliphatic hydrocarbons Aliphatic homopolycyclic compound Branched unsaturated hydrocarbon Cyclic olefin Hydrocarbon Longifolane or isolongifolane sesquiterpenoid Olefin Polycyclic hydrocarbon Sesquiterpenoid Unsaturated aliphatic hydrocarbon Unsaturated hydrocarbon Humulenes Longifolane sesquiterpenoids a diterpenoid sesquiterpene logp 4.65 ALOGPS logs -5.21 ALOGPS solubility 1.26e-03 g/l ALOGPS logp 4.16 ChemAxon iupac 3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0²,⁹]undecane ChemAxon average_mass 204.357 ChemAxon mono_mass 204.187800773 ChemAxon smiles CC12CCCC(C)(C)C3C(CCC13)C2=C ChemAxon formula C15H24 ChemAxon inchi InChI=1S/C15H24/c1-10-11-6-7-12-13(11)14(2,3)8-5-9-15(10,12)4/h11-13H,1,5-9H2,2-4H3 ChemAxon inchikey PDSNLYSELAIEBU-UHFFFAOYSA-N ChemAxon polar_surface_area 0 ChemAxon refractivity 64.62 ChemAxon polarizability 25.42 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 0 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 5986 Specdb::EiMs 1738 Specdb::MsMs 81918 Specdb::MsMs 81919 Specdb::MsMs 81920 Specdb::MsMs 143142 Specdb::MsMs 143143 Specdb::MsMs 143144 Specdb::MsMs 3602147 Specdb::MsMs 3602148 Specdb::MsMs 3602149 Specdb::MsMs 3602150 Specdb::MsMs 3602151 Specdb::MsMs 3602152 6530 Cheese Type 2 specific Corn Type 1 specific Zea mays 4577 Mandarin orange (Clementine, Tangerine) Type 1 specific Citrus reticulata 85571 0.1 0.1 0.1 mg/100 g Rosemary Type 1 specific Rosmarinus officinalis 39367 5.75 5.75 5.75 mg/100 g Star anise Type 1 specific Illicium verum 124778 0.1 0.1 0.1 mg/100 g fir needle medical rose sweet woody