1.0 2010-04-08 22:11:19 UTC 2019-11-26 03:10:16 UTC FDB014521 Taraxinic acid Taraxinic acid, also known as taraxinate, belongs to germacranolides and derivatives class of compounds. Those are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Taraxinic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Taraxinic acid can be found in dandelion, which makes taraxinic acid a potential biomarker for the consumption of this food product. Taraxin acid Taraxinic acid C15H18O4 262.301 262.120509064 10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid 10-methyl-3-methylidene-2-oxo-3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(O)=O InChI=1S/C15H18O4/c1-9-4-3-5-11(14(16)17)6-7-12-10(2)15(18)19-13(12)8-9/h5,8,12-13H,2-4,6-7H2,1H3,(H,16,17)/b9-8-,11-5+ KZWCOWFKXMTBRH-IMDCMVKOSA-N belongs to the class of organic compounds known as germacranolides and derivatives. These are sesquiterpene lactones with a structure based on the germacranolide skeleton, characterized by a gamma lactone fused to a 1,7-dimethylcyclodec-1-ene moiety. Germacranolides and derivatives Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aliphatic heteropolycyclic compounds Carbonyl compounds Carboxylic acids Dicarboxylic acids and derivatives Enoate esters Gamma butyrolactones Germacrane sesquiterpenoids Hydrocarbon derivatives Organic oxides Oxacyclic compounds Tetrahydrofurans Aliphatic heteropolycyclic compound Alpha,beta-unsaturated carboxylic ester Carbonyl group Carboxylic acid Carboxylic acid derivative Carboxylic acid ester Dicarboxylic acid or derivatives Enoate ester Gamma butyrolactone Germacrane sesquiterpenoid Germacranolide Hydrocarbon derivative Lactone Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Sesquiterpenoid Tetrahydrofuran logp 2.43 ALOGPS logs -2.86 ALOGPS solubility 3.65e-01 g/l ALOGPS melting_point Mp 156-157° logp 3.01 ChemAxon pka_strongest_acidic 4.57 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac 10-methyl-3-methylidene-2-oxo-2H,3H,3aH,4H,5H,8H,9H,11aH-cyclodeca[b]furan-6-carboxylic acid ChemAxon average_mass 262.301 ChemAxon mono_mass 262.120509064 ChemAxon smiles C\C1=C\C2OC(=O)C(=C)C2CC\C(=C/CC1)C(O)=O ChemAxon formula C15H18O4 ChemAxon inchi InChI=1S/C15H18O4/c1-9-4-3-5-11(14(16)17)6-7-12-10(2)15(18)19-13(12)8-9/h5,8,12-13H,2-4,6-7H2,1H3,(H,16,17)/b9-8-,11-5+ ChemAxon inchikey KZWCOWFKXMTBRH-IMDCMVKOSA-N ChemAxon polar_surface_area 63.6 ChemAxon refractivity 71.66 ChemAxon polarizability 27.11 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 63624 Specdb::MsMs 63625 Specdb::MsMs 63626 Specdb::MsMs 120594 Specdb::MsMs 120595 Specdb::MsMs 120596 Specdb::MsMs 3605695 Specdb::MsMs 3605696 Specdb::MsMs 3605697 Specdb::MsMs 3605698 Specdb::MsMs 3605699 Specdb::MsMs 3605700 Dandelion Type 1 specific Taraxacum officinale 50225