1.0 2011-03-17 23:28:01 UTC 2019-11-26 03:20:48 UTC FDB021725 11b,13-Dihydrolactucin 11b,13-dihydrolactucin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 11b,13-dihydrolactucin can be found in a number of food items such as endive, chicory, dandelion, and romaine lettuce, which makes 11b,13-dihydrolactucin a potential biomarker for the consumption of these food products. 11b,13-Dihydrolactucin 8,15-Dihydroxy-2-oxo-1(10),3-guaiadien-12,6-olide 8,15-Dihydroxy-2-oxo-1(10),3,11(13)-guaiatrien-12,6-olide; (5a,6a,8a)-form, 11b,13-Dihydro C16H20O5 292.327 292.13107375 (3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione (3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-3H,3aH,4H,5H,9bH-azuleno[4,5-b]furan-2,7-dione 83117-63-9 [H][C@]12OC(=O)[C@H](C)[C@]1([H])[C@H](O)CC(C)=C1C(=O)C=C(CO)[C@]21C InChI=1S/C16H20O5/c1-7-4-10(18)12-8(2)15(20)21-14(12)16(3)9(6-17)5-11(19)13(7)16/h5,8,10,12,14,17-18H,4,6H2,1-3H3/t8-,10-,12-,14+,16+/m1/s1 AVVAXORRBBPMQM-YRRGMINMSA-N belongs to the class of organic compounds known as ambrosanolides and secoambrosanolides. These are sesquiterpene lactones from the Ambrosia family, with a backbone derivative of azuleno[6,5-b]furan-2-one (ambrosanolides) or azuleno[4,5-b]furan-2-one (secoambrosanolides). Ambrosanolides and secoambrosanolides Organic compounds Lipids and lipid-like molecules Prenol lipids Terpene lactones Aliphatic heteropolycyclic compounds Carboxylic acid esters Gamma butyrolactones Hydrocarbon derivatives Ketones Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Primary alcohols Pseudoguaianes Secondary alcohols Tetrahydrofurans Alcohol Aliphatic heteropolycyclic compound Ambrosanolide Carbonyl group Carboxylic acid derivative Carboxylic acid ester Gamma butyrolactone Hydrocarbon derivative Ketone Lactone Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Primary alcohol Pseudoguaiane sesquiterpenoid Secondary alcohol Sesquiterpenoid Tetrahydrofuran solid logp 0.38 ALOGPS logs -2.04 ALOGPS solubility 2.69e+00 g/l ALOGPS melting_point Mp 91? logp 0.22 ChemAxon pka_strongest_acidic 14.6 ChemAxon pka_strongest_basic -2.8 ChemAxon iupac (3R,3aR,4R,9aS,9bS)-4-hydroxy-9-(hydroxymethyl)-3,6,9a-trimethyl-2H,3H,3aH,4H,5H,7H,9aH,9bH-azuleno[4,5-b]furan-2,7-dione ChemAxon average_mass 292.327 ChemAxon mono_mass 292.13107375 ChemAxon smiles [H][C@]12OC(=O)[C@H](C)[C@]1([H])[C@H](O)CC(C)=C1C(=O)C=C(CO)[C@]21C ChemAxon formula C16H20O5 ChemAxon inchi InChI=1S/C16H20O5/c1-7-4-10(18)12-8(2)15(20)21-14(12)16(3)9(6-17)5-11(19)13(7)16/h5,8,10,12,14,17-18H,4,6H2,1-3H3/t8-,10-,12-,14+,16+/m1/s1 ChemAxon inchikey AVVAXORRBBPMQM-YRRGMINMSA-N ChemAxon polar_surface_area 83.83 ChemAxon refractivity 76.46 ChemAxon polarizability 30.09 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 1221538 Specdb::MsMs 1221539 Specdb::MsMs 1221540 Specdb::MsMs 1337200 Specdb::MsMs 1337201 Specdb::MsMs 1337202 Specdb::MsMs 3606835 Specdb::MsMs 3606836 Specdb::MsMs 3606837 Specdb::MsMs 3606838 Specdb::MsMs 3606839 Specdb::MsMs 3606840 Chicory Type 1 specific Cichorium intybus 13427 Dandelion Type 1 specific Taraxacum officinale 50225 Endive Type 1 specific Cichorium endivia 114280 Lettuce Type 1 specific Lactuca sativa 4236 Romaine lettuce Type 1 specific Lactuca sativa L. var. longifolia Bitter 732