1.0 2016-09-30 22:52:41 UTC 2020-06-04 21:10:23 UTC BMDB0002209 BMDB02209 Equol Equol, also known as aus-131(S)-equol or 3'-hydroxy-equol, belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. Equol exists as a solid, possibly soluble (in water), and an extremely weak basic (essentially neutral) compound (based on its pKa) molecule. Equol is a potentially toxic compound. (+-)-Isomer OF equol 3' Hydroxy equol 3'-Hydroxy-equol 4' O Methyl equol 4' Methoxy 7 isoflavanol 4'-O-Methyl equol 4'-Methoxy-7-isoflavanol 6' Hydroxy equol 6'-Hydroxy-equol Equol, 4'-O-methyl AUS-131(S)-equol (-)-(S)-Equol (-)-Equol (S)-(-)-4',7-Isoflavandiol (S)-3,4-dihydro-3-(4-Hydroxyphenyl)-2H-1-benzopyran-7-ol (S)-Equol 4',7-Dihydroxyisoflavan 4',7-Isoflavandiol C15H14O3 242.2699 242.094294314 (3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol (-)-equol 531-95-3 OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC=C2C1 InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1 ADFCQWZHKCXPAJ-GFCCVEGCSA-N belongs to the class of organic compounds known as isoflavanols. These are polycyclic compounds containing a hydroxylated isoflavan skeleton. Organic compounds Phenylpropanoids and polyketides Isoflavonoids Isoflavans Isoflavanols 1-benzopyrans 1-hydroxy-2-unsubstituted benzenoids Alkyl aryl ethers Benzene and substituted derivatives Hydrocarbon derivatives Hydroxyisoflavonoids Oxacyclic compounds 1-benzopyran 1-hydroxy-2-unsubstituted benzenoid Alkyl aryl ether Aromatic heteropolycyclic compound Benzenoid Benzopyran Chromane Ether Hydrocarbon derivative Hydroxyisoflavonoid Isoflavanol Monocyclic benzene moiety Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Phenol Aromatic heteropolycyclic compounds Isoflavanes hydroxyisoflavans isoflavans Solid logp 2.91 ALOGPS logs -3.74 ALOGPS logp 3.19 ChemAxon pka_strongest_acidic 9.63 ChemAxon pka_strongest_basic -4.9 ChemAxon iupac (3S)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol ChemAxon average_mass 242.2699 ChemAxon mono_mass 242.094294314 ChemAxon smiles OC1=CC=C(C=C1)[C@H]1COC2=CC(O)=CC=C2C1 ChemAxon formula C15H14O3 ChemAxon inchi InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m1/s1 ChemAxon inchikey ADFCQWZHKCXPAJ-GFCCVEGCSA-N ChemAxon polar_surface_area 49.69 ChemAxon refractivity 68.96 ChemAxon polarizability 25.81 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 3 ChemAxon donor_count 2 ChemAxon physiological_charge 0 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::CMs 11314 Specdb::CMs 38318 Specdb::CMs 152511 Specdb::MsMs 102969 Specdb::MsMs 102970 Specdb::MsMs 102971 Specdb::MsMs 168879 Specdb::MsMs 168880 Specdb::MsMs 168881 Specdb::MsMs 2260369 Specdb::MsMs 2260370 Specdb::MsMs 2260371 Specdb::MsMs 3077913 Specdb::MsMs 3077914 Specdb::MsMs 3077915 Milk 0.0206 - 0.124 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 0.194 +/- 0.0144 uM Commercial, homogenized fresh full cream (n=5) Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke Cow’s milk as a dietary source of equol and phenolic antioxidants: di erential distribution in the milk aqueous and lipid fractions. Dairy Sci. & Technol. (2014) 94:625–632. DOI 10.1007/s13594-014-0183-4 Milk 0.0778 +/- 0.0103 uM Commercial, homogenized, fresh low fat (n=4) Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke Cow’s milk as a dietary source of equol and phenolic antioxidants: di erential distribution in the milk aqueous and lipid fractions. Dairy Sci. & Technol. (2014) 94:625–632. DOI 10.1007/s13594-014-0183-4 Milk 0.00516 +/- 0.00347 uM Commercial, homogenized, fresh non-fat milk Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke Cow’s milk as a dietary source of equol and phenolic antioxidants: di erential distribution in the milk aqueous and lipid fractions. Dairy Sci. & Technol. (2014) 94:625–632. DOI 10.1007/s13594-014-0183-4 Milk 0.00239 +/- 8.255e-05 uM Whole milk Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke Cow’s milk as a dietary source of equol and phenolic antioxidants: di erential distribution in the milk aqueous and lipid fractions. Dairy Sci. & Technol. (2014) 94:625–632. DOI 10.1007/s13594-014-0183-4 Milk 0.186 - 1.209 uM Raw milk. Range in australian herds King RA, Mano MM, Head RJ: Assessment of isoflavonoid concentrations in Australian bovine milk samples. J Dairy Res. 1998 Aug;65(3):479-89. 9718497 Milk 0.256 uM Pasteurized skim milk Hoikkala A, Mustonen E, Saastamoinen I, Jokela T, Taponen J, Saloniemi H, Wahala K: High levels of equol in organic skimmed Finnish cow milk. Mol Nutr Food Res. 2007 Jul;51(7):782-6. doi: 10.1002/mnfr.200600222. 17576638 Milk 1.696 uM Pasteurized organic milk Hoikkala A, Mustonen E, Saastamoinen I, Jokela T, Taponen J, Saloniemi H, Wahala K: High levels of equol in organic skimmed Finnish cow milk. Mol Nutr Food Res. 2007 Jul;51(7):782-6. doi: 10.1002/mnfr.200600222. 17576638 Milk 1125.604 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 1502.456 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 214.637 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 400.793 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 Milk 0.237 - 4.140 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 C14131 FDB021824 DB11674 82594 91469 428126 C00009707 Equol Wang, Xiu-Ling; Hur, Hor-Gil; Lee, Je Hyeon; Kim, Ki Tae; Kim, Su-Il. Enantioselective synthesis of S-equol from dihydrodaidzein by a newly isolated anaerobic human intestinal bacterium. Applied and Environmental Microbiology (2005), 71(1), 214-219 King RA, Mano MM, Head RJ: Assessment of isoflavonoid concentrations in Australian bovine milk samples. J Dairy Res. 1998 Aug;65(3):479-89. 9718497 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 Hoikkala A, Mustonen E, Saastamoinen I, Jokela T, Taponen J, Saloniemi H, Wahala K: High levels of equol in organic skimmed Finnish cow milk. Mol Nutr Food Res. 2007 Jul;51(7):782-6. doi: 10.1002/mnfr.200600222. 17576638 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 Shin Tsen, Jinyi Siew, Eunice Lau, Farzana A qah Bte Roslee, Hui Chan, Wai Loke Cow’s milk as a dietary source of equol and phenolic antioxidants: di erential distribution in the milk aqueous and lipid fractions. Dairy Sci. & Technol. (2014) 94:625–632. DOI 10.1007/s13594-014-0183-4