1.02010-04-08 22:05:30 UTC2019-11-26 02:57:55 UTCFDB002752Gardenin BGardenin b, also known as demethyltangeretin or 5-hydroxy-4',6,7,8-tetramethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, gardenin b is considered to be a flavonoid lipid molecule. Gardenin b is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Gardenin b can be found in mandarin orange (clementine, tangerine), peppermint, sweet basil, and winter savory, which makes gardenin b a potential biomarker for the consumption of these food products. 5-Desmethyltangeretin5-Hydroxy-4',6,7,8-tetramethoxyflavone5-Hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one5-hydroxy-6,7,8,4'-tetramethoxyflavone5-O-DemethyltangeretinDemethyltangeretinFlavone, 5-hydroxy-4',6,7,8-tetramethoxy-Gardenin BC19H18O7358.342358.105252935-hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-onegardenin B2798-20-1COC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OInChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3LXEVSYZNYDZSOB-UHFFFAOYSA-N belongs to the class of organic compounds known as 8-o-methylated flavonoids. These are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone.8-O-methylated flavonoidsOrganic compoundsPhenylpropanoids and polyketidesFlavonoidsO-methylated flavonoidsAromatic heteropolycyclic compounds4'-O-methylated flavonoids5-hydroxyflavonoids6-O-methylated flavonoids7-O-methylated flavonoidsAlkyl aryl ethersAnisolesChromonesFlavonesHeteroaromatic compoundsHydrocarbon derivativesMethoxybenzenesOrganic oxidesOxacyclic compoundsPhenoxy compoundsPyranones and derivativesVinylogous acids1-benzopyran4p-methoxyflavonoid-skeleton5-hydroxyflavonoid6-methoxyflavonoid-skeleton7-methoxyflavonoid-skeleton8-methoxyflavonoid-skeletonAlkyl aryl etherAnisoleAromatic heteropolycyclic compoundBenzenoidBenzopyranChromoneEtherFlavoneHeteroaromatic compoundHydrocarbon derivativeHydroxyflavonoidMethoxybenzeneMonocyclic benzene moietyOrganic oxideOrganic oxygen compoundOrganoheterocyclic compoundOrganooxygen compoundOxacyclePhenol etherPhenoxy compoundPyranPyranoneVinylogous acidFlavones and FlavonolsFlavones and Flavonolsflavonesmonohydroxyflavonetetramethoxyflavonelogp3.07logs-4.19solubility2.30e-02 g/lmelting_pointMp 180-181° (176-177°)logp2.68pka_strongest_acidic9.66pka_strongest_basic-4.3iupac5-hydroxy-6,7,8-trimethoxy-2-(4-methoxyphenyl)-4H-chromen-4-oneaverage_mass358.342mono_mass358.10525293smilesCOC1=CC=C(C=C1)C1=CC(=O)C2=C(O1)C(OC)=C(OC)C(OC)=C2OformulaC19H18O7inchiInChI=1S/C19H18O7/c1-22-11-7-5-10(6-8-11)13-9-12(20)14-15(21)17(23-2)19(25-4)18(24-3)16(14)26-13/h5-9,21H,1-4H3inchikeyLXEVSYZNYDZSOB-UHFFFAOYSA-Npolar_surface_area83.45refractivity94.8polarizability36.75rotatable_bond_count5acceptor_count7donor_count1physiological_charge0formal_charge0Specdb::MsMs71388Specdb::MsMs71389Specdb::MsMs71390Specdb::MsMs130038Specdb::MsMs130039Specdb::MsMs130040Specdb::MsMs3599116Specdb::MsMs3599117Specdb::MsMs3599118Specdb::MsMs3599119Specdb::MsMs3599120Mandarin orange (Clementine, Tangerine)Type 1specificCitrus reticulata85571PeppermintType 1specificMentha X piperita3425618.72214318.72214259418.722142594mg/100 gSweet basilType 1specificOcimum basilicum39350Winter savoryType 1specificSatureja montana49988