1.0 2010-04-08 22:06:26 UTC 2025-11-18 22:57:48 UTC FDB004902 Sesquiterpenes Sesquiterpenes belongs to eudesmanolides, secoeudesmanolides, and derivatives class of compounds. Those are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Sesquiterpenes is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Sesquiterpenes is a bitter tasting compound found in ceylon cinnamon, pepper (spice), and potato, which makes sesquiterpenes a potential biomarker for the consumption of these food products. Sesquiterpenes are a class of terpenes that consist of three isoprene units and have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids . Santonin C15H18O3 246.3016 246.125594442 (3R,3aS,5aR,9bR)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione (3R,3aS,5aR,9bR)-3,5a,9-trimethyl-3H,3aH,4H,5H,9bH-naphtho[1,2-b]furan-2,8-dione 481-06-1 C[C@@H]1[C@@H]2CC[C@]3(C)C=CC(=O)C(C)=C3[C@@H]2OC1=O InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10+,13-,15-/m1/s1 XJHDMGJURBVLLE-FMBSFYNOSA-N belongs to the class of organic compounds known as eudesmanolides, secoeudesmanolides, and derivatives. These are terpenoids with a structure based on the eudesmanolide (a 3,5a,9-trimethyl-naphtho[1,2-b]furan-2-one derivative) or secoeudesmanolide (a 3,6-dimethyl-5-(pentan-2-yl)-1-benzofuran-2-one derivative) skeleton. Eudesmanolides, secoeudesmanolides, and derivatives Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aliphatic heteropolycyclic compounds Carboxylic acid esters Cyclic ketones Gamma butyrolactones Hydrocarbon derivatives Monocarboxylic acids and derivatives Naphthofurans Organic oxides Oxacyclic compounds Sesquiterpenoids Tetrahydrofurans Aliphatic heteropolycyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cyclic ketone Eudesmanolide Gamma butyrolactone Hydrocarbon derivative Ketone Lactone Monocarboxylic acid or derivatives Naphthofuran Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Sesquiterpenoid Tetrahydrofuran logp 1.98 ALOGPS logs -2.92 ALOGPS solubility 2.95e-01 g/l ALOGPS logp 2.6 ChemAxon pka_strongest_basic -6.1 ChemAxon iupac (3R,3aS,5aR,9bR)-3,5a,9-trimethyl-2H,3H,3aH,4H,5H,5aH,8H,9bH-naphtho[1,2-b]furan-2,8-dione ChemAxon average_mass 246.3016 ChemAxon mono_mass 246.125594442 ChemAxon smiles C[C@@H]1[C@@H]2CC[C@]3(C)C=CC(=O)C(C)=C3[C@@H]2OC1=O ChemAxon formula C15H18O3 ChemAxon inchi InChI=1S/C15H18O3/c1-8-10-4-6-15(3)7-5-11(16)9(2)12(15)13(10)18-14(8)17/h5,7-8,10,13H,4,6H2,1-3H3/t8-,10+,13-,15-/m1/s1 ChemAxon inchikey XJHDMGJURBVLLE-FMBSFYNOSA-N ChemAxon polar_surface_area 43.37 ChemAxon refractivity 68.83 ChemAxon polarizability 25.97 ChemAxon rotatable_bond_count 0 ChemAxon acceptor_count 2 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 62265 Specdb::MsMs 62266 Specdb::MsMs 62267 Specdb::MsMs 118950 Specdb::MsMs 118951 Specdb::MsMs 118952 Specdb::MsMs 3601187 Specdb::MsMs 3601188 Specdb::MsMs 3601189 Specdb::MsMs 3601190 Specdb::MsMs 3601191 Specdb::MsMs 3601192 35189 Asian pear Type 1 specific Pyrus pyrifolia 3767 Celery stalks Type 1 specific Apium graveolens var. dulce 117781 Ceylon cinnamon Type 1 specific Cinnamomum verum 128608 Pepper (Spice) Type 1 specific Piper nigrum 13216 Potato Type 1 specific Solanum tuberosum 4113 bitter