1.0 2010-04-08 22:04:29 UTC 2025-11-18 22:16:29 UTC FDB000230 Valoneic acid dilactone Valoneic acid dilactone is a member of the class of compounds known as hydrolyzable tannins. Hydrolyzable tannins are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Valoneic acid dilactone is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Valoneic acid dilactone can be found in cloves, common walnut, and japanese walnut, which makes valoneic acid dilactone a potential biomarker for the consumption of these food products. Valoneic acid dilactone is a hydrolysable tannin that can be isolated from the heartwood of Shorea laeviforia and in oaks species like the North American white oak (Quercus alba) and European red oak (Quercus robur) . C21H10O13 470.298 470.012140382 3,4,5-trihydroxy-2-({7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)benzoic acid 3,4,5-trihydroxy-2-({7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)benzoic acid OC(=O)C1=C(OC2=C(O)C3=C4C(=C2)C(=O)OC2=C(O)C(O)=CC(C(=O)O3)=C42)C(O)=C(O)C(O)=C1 InChI=1S/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29) BPAOAXAAABIQKR-UHFFFAOYSA-N belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. Hydrolyzable tannins Organic compounds Phenylpropanoids and polyketides Tannins Hydrolyzable tannins Aromatic heteropolycyclic compounds 1-benzopyrans 1-hydroxy-2-unsubstituted benzenoids 1-hydroxy-4-unsubstituted benzenoids 2-benzopyrans 7,8-dihydroxycoumarins Benzoic acids Benzoyl derivatives Carboxylic acids Diarylethers Ellagic acids and derivatives Gallic acids Heteroaromatic compounds Hydrocarbon derivatives Isocoumarins and derivatives Lactones Monocarboxylic acids and derivatives Organic oxides Oxacyclic compounds Phenol ethers Phenoxy compounds Polyols Pyranones and derivatives Pyrogallols and derivatives 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid 1-hydroxy-4-unsubstituted benzenoid 2-benzopyran 7,8-dihydroxycoumarin Aromatic heteropolycyclic compound Benzenetriol Benzenoid Benzoic acid Benzoic acid or derivatives Benzopyran Benzoyl Carboxylic acid Carboxylic acid derivative Coumarin Diaryl ether Ellagic_acid Ether Gallic acid Gallic acid or derivatives Heteroaromatic compound Hydrocarbon derivative Hydrolyzable tannin Hydroxybenzoic acid Isocoumarin Lactone Monocarboxylic acid or derivatives Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Phenol ether Phenoxy compound Polyol Pyran Pyranone Pyrogallol derivative logp 2.61 ALOGPS logs -3.59 ALOGPS solubility 1.20e-01 g/l ALOGPS logp 2.87 ChemAxon pka_strongest_acidic 3.45 ChemAxon pka_strongest_basic -3.8 ChemAxon iupac 3,4,5-trihydroxy-2-({7,13,14-trihydroxy-3,10-dioxo-2,9-dioxatetracyclo[6.6.2.0⁴,¹⁶.0¹¹,¹⁵]hexadeca-1(14),4,6,8(16),11(15),12-hexaen-6-yl}oxy)benzoic acid ChemAxon average_mass 470.298 ChemAxon mono_mass 470.012140382 ChemAxon smiles OC(=O)C1=C(OC2=C(O)C3=C4C(=C2)C(=O)OC2=C(O)C(O)=CC(C(=O)O3)=C42)C(O)=C(O)C(O)=C1 ChemAxon formula C21H10O13 ChemAxon inchi InChI=1S/C21H10O13/c22-7-2-6(19(28)29)16(15(27)12(7)24)32-9-3-5-11-10-4(20(30)34-18(11)14(9)26)1-8(23)13(25)17(10)33-21(5)31/h1-3,22-27H,(H,28,29) ChemAxon inchikey BPAOAXAAABIQKR-UHFFFAOYSA-N ChemAxon polar_surface_area 220.51 ChemAxon refractivity 108.07 ChemAxon polarizability 40.96 ChemAxon rotatable_bond_count 3 ChemAxon acceptor_count 10 ChemAxon donor_count 7 ChemAxon physiological_charge -3 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 88581 Specdb::MsMs 88582 Specdb::MsMs 88583 Specdb::MsMs 151335 Specdb::MsMs 151336 Specdb::MsMs 151337 Specdb::MsMs 3220924 Specdb::MsMs 3220925 Specdb::MsMs 3220926 Specdb::MsMs 3596860 Specdb::MsMs 3596861 Specdb::MsMs 3596862 Cloves Type 1 specific Syzygium aromaticum 219868 18.0 18.0 18.0 mg/100 g Common walnut Type 1 specific Juglans regia 51240 98.435432 196.870864868 0.0 mg/100 g Japanese walnut Type 1 specific Juglans ailanthifolia 91209 44.873067 89.74613444 0.0 mg/100 g