1.0 2016-09-30 23:03:30 UTC 2020-06-04 20:48:12 UTC BMDB0003312 BMDB03312 Daidzein Daidzein, also known as daidzeol or isoaurostatin, belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Thus, daidzein is considered to be a flavonoid lipid molecule. Daidzein exists as a solid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. Daidzein is a potentially toxic compound. 4',7-Dihydroxyisoflavone 7,4'-Dihydroxyisoflavone 7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyrone 7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one Daidzeol Isoaurostatin Diadzein 4',7-Dihydroxy-isoflavone C15H10O4 254.241 254.057908802 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one daidzein 486-66-8 OC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H ZQSIJRDFPHDXIC-UHFFFAOYSA-N belongs to the class of organic compounds known as isoflavones. These are polycyclic compounds containing a 2-isoflavene skeleton which bears a ketone group at the C4 carbon atom. Organic compounds Phenylpropanoids and polyketides Isoflavonoids Isoflav-2-enes Isoflavones 1-hydroxy-2-unsubstituted benzenoids Benzene and substituted derivatives Chromones Heteroaromatic compounds Hydrocarbon derivatives Hydroxyisoflavonoids Organic oxides Organooxygen compounds Oxacyclic compounds Pyranones and derivatives 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromone Heteroaromatic compound Hydrocarbon derivative Hydroxyisoflavonoid Isoflavone Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Pyran Pyranone Aromatic heteropolycyclic compounds 7-hydroxyisoflavones Isoflavonoids Isoflavonoids a 4'-hydroxyisoflavone an isoflavone isoflavones Solid melting_point 323 °C logp 3.30 ALOGPS logs -3.48 ALOGPS logp 2.73 ChemAxon pka_strongest_acidic 6.48 ChemAxon pka_strongest_basic -5.3 ChemAxon iupac 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one ChemAxon average_mass 254.241 ChemAxon mono_mass 254.057908802 ChemAxon smiles OC1=CC=C(C=C1)C1=COC2=C(C=CC(O)=C2)C1=O ChemAxon formula C15H10O4 ChemAxon inchi InChI=1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H ChemAxon inchikey ZQSIJRDFPHDXIC-UHFFFAOYSA-N ChemAxon polar_surface_area 66.76 ChemAxon refractivity 69.7 ChemAxon polarizability 25.75 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon number_of_rings 3 ChemAxon bioavailability 1 ChemAxon rule_of_five Yes ChemAxon ghose_filter Yes ChemAxon veber_rule Yes ChemAxon mddr_like_rule Yes ChemAxon Specdb::NmrTwoD 1881 Specdb::NmrOneD 1947 Specdb::NmrOneD 166532 Specdb::CMs 836 Specdb::CMs 2166 Specdb::CMs 5575 Specdb::CMs 30505 Specdb::CMs 31450 Specdb::CMs 32170 Specdb::CMs 38565 Specdb::CMs 160069 Specdb::MsMs 2236 Specdb::MsMs 2237 Specdb::MsMs 2238 Specdb::MsMs 5873 Specdb::MsMs 5874 Specdb::MsMs 5875 Specdb::MsMs 5876 Specdb::MsMs 5877 Specdb::MsMs 5878 Specdb::MsMs 5880 Specdb::MsMs 5881 Specdb::MsMs 5882 Specdb::MsMs 5883 Specdb::MsMs 5884 Specdb::MsMs 5885 Specdb::MsMs 5886 Specdb::MsMs 5887 Specdb::MsMs 11678 Specdb::MsMs 11679 Specdb::MsMs 11680 Specdb::MsMs 18350 Specdb::MsMs 18351 Specdb::MsMs 18352 Specdb::MsMs 20162 Specdb::MsMs 20163 Milk 0.00118 - 0.0224 uM Raw milk, range from both high equol and low equol milk - high = diet of mainly red clover Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. 19679050 Milk 0.000393 - 0.00787 uM Raw milk Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-64. doi: 10.1002/rcm.1052. 12811748 Milk 7.159 uM Raw milk. Diet: red clover, concentrate supplement Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. 18565930 Milk 30.326 uM Raw milk. Diet: red clover, no concentrate supplement Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. 18565930 Milk 2.635 uM Raw milk. Diet: white clover, concentrate supplement Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. 18565930 Milk 0.905 uM Raw milk. Diet: white clover, no concentrate supplement Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. 18565930 C10208 FDB002608 4445025 28197 5281708 DB13182 C00009380 394 DAIDZEIN Daidzein Baker, Wilson; Robinson, Robert; Simpson, N. M. Synthetical experiments in the isoflavone group. VII. Synthesis of daidzein. Journal of the Chemical Society (1933), 274-5. Antignac JP, Cariou R, Le Bizec B, Cravedi JP, Andre F: Identification of phytoestrogens in bovine milk using liquid chromatography/electrospray tandem mass spectrometry. Rapid Commun Mass Spectrom. 2003;17(12):1256-64. doi: 10.1002/rcm.1052. 12811748 Steinshamn H, Purup S, Thuen E, Hansen-Moller J: Effects of clover-grass silages and concentrate supplementation on the content of phytoestrogens in dairy cow milk. J Dairy Sci. 2008 Jul;91(7):2715-25. doi: 10.3168/jds.2007-0857. 18565930 Nielsen TS, Norgaard JV, Purup S, Frette XC, Bonefeld-Jorgensen EC: Estrogenic activity of bovine milk high or low in equol using immature mouse uterotrophic responses and an estrogen receptor transactivation assay. Cancer Epidemiol. 2009 Jul;33(1):61-8. doi: 10.1016/j.canep.2009.04.003. Epub 2009 May 31. 19679050