1.02010-04-08 22:04:29 UTC2019-11-26 02:54:34 UTCFDB000230Valoneic acid dilactoneValoneic 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) .C21H10O13470.298470.0121403823,4,5-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 acid3,4,5-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 acidOC(=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)=C1InChI=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 tanninsOrganic compoundsPhenylpropanoids and polyketidesTanninsHydrolyzable tanninsAromatic heteropolycyclic compounds1-benzopyrans1-hydroxy-2-unsubstituted benzenoids1-hydroxy-4-unsubstituted benzenoids2-benzopyrans7,8-dihydroxycoumarinsBenzoic acidsBenzoyl derivativesCarboxylic acidsDiarylethersEllagic acids and derivativesGallic acidsHeteroaromatic compoundsHydrocarbon derivativesIsocoumarins and derivativesLactonesMonocarboxylic acids and derivativesOrganic oxidesOxacyclic compoundsPhenol ethersPhenoxy compoundsPolyolsPyranones and derivativesPyrogallols and derivatives1-benzopyran1-hydroxy-2-unsubstituted benzenoid1-hydroxy-4-unsubstituted benzenoid2-benzopyran7,8-dihydroxycoumarinAromatic heteropolycyclic compoundBenzenetriolBenzenoidBenzoic acidBenzoic acid or derivativesBenzopyranBenzoylCarboxylic acidCarboxylic acid derivativeCoumarinDiaryl etherEllagic_acidEtherGallic acidGallic acid or derivativesHeteroaromatic compoundHydrocarbon derivativeHydrolyzable tanninHydroxybenzoic acidIsocoumarinLactoneMonocarboxylic acid or derivativesMonocyclic benzene moietyOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacyclePhenolPhenol etherPhenoxy compoundPolyolPyranPyranonePyrogallol derivativelogp2.61logs-3.59solubility1.20e-01 g/llogp2.87pka_strongest_acidic3.45pka_strongest_basic-3.8iupac3,4,5-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 acidaverage_mass470.298mono_mass470.012140382smilesOC(=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)=C1formulaC21H10O13inchiInChI=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)inchikeyBPAOAXAAABIQKR-UHFFFAOYSA-Npolar_surface_area220.51refractivity108.07polarizability40.96rotatable_bond_count3acceptor_count10donor_count7physiological_charge-3formal_charge0Specdb::MsMs88581Specdb::MsMs88582Specdb::MsMs88583Specdb::MsMs151335Specdb::MsMs151336Specdb::MsMs151337Specdb::MsMs3220924Specdb::MsMs3220925Specdb::MsMs3220926Specdb::MsMs3596860Specdb::MsMs3596861Specdb::MsMs3596862ClovesType 1specificSyzygium aromaticum21986818.018.018.0mg/100 gCommon walnutType 1specificJuglans regia5124098.435432196.8708648680.0mg/100 gJapanese walnutType 1specificJuglans ailanthifolia9120944.87306789.746134440.0mg/100 g