| Identification | Back Directory | [Name]
(+/-)-EQUOL | [CAS]
94105-90-5 | [Synonyms]
NV 07α
(+/-)Equol
(+/-)-EQUOL
Equol,99%e.e.
EQUOL(RACEMIC)
(+/-)-Equol>
(+/-)-Equol (GMP)
7,4'-HoMoisoflavane
(±)-EQUOL >= 99.0% (TLC)
4′,7-Dihydroxyisoflavane
4',7-Isoflavandiol, (+/-)-Equol
Equol,3-(4-Hydroxyphenyl)-7-chromanol
(+/-)-7-Hydroxy-3-(4-hydroxyphenyl)chroman
Nano Liposomal Equol,3-(4-Hydroxyphenyl)-7-chromanol
3,4-dihydro-3-(4-hydroxyphenyl)-2h-1-benzopyran-7-ol
2H-1-Benzopyran-7-ol, 3,4-dihydro-3-(4-hydroxyphenyl)-
Anti hair loss s equol 94105-90-5 s-equol powder 99% purity equol
(+/-)-3,4-Dihydro-3-(4-hydroxyphenyl)-2H-chromen-7-ol, (+/-)-Equol
3-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
7-Hydroxy-3-(4-hydroxyphenyl)chroman
4',7-Isoflavandiol
3,4-Dihydro-3-(4-hydroxyphenyl)-2H-chromen-7-ol, (+/-)-Equol, 4',7-Isoflavandiol, 7-Hydroxy-3-(4-hydroxyphenyl)chroman | [EINECS(EC#)]
618-999-2 | [Molecular Formula]
C15H14O3 | [MDL Number]
MFCD00016662 | [MOL File]
94105-90-5.mol | [Molecular Weight]
242.28 |
| Chemical Properties | Back Directory | [Melting point ]
158-160?C | [Boiling point ]
441.7±45.0 °C(Predicted) | [density ]
1.286±0.06 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer | [solubility ]
soluble in Ethanol | [form ]
Crystalline powder | [pka]
9.94±0.40(Predicted) | [color ]
White to Light yellow to Light red | [Water Solubility ]
Soluble in DMSO and methanol or 100% ethanol. Insoluble in water. | [Sensitive ]
Hygroscopic | [BRN ]
87752 | [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 | [InChIKey]
ADFCQWZHKCXPAJ-UHFFFAOYSA-N | [SMILES]
C1OC2=CC(O)=CC=C2CC1C1=CC=C(O)C=C1 |
| Hazard Information | Back Directory | [Description]
Equol is a nonsteroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein by human intestinal microflora. The estrogen receptor (ER) binding activity of the naturally occurring (S)-enantiomer demonstrates greater affinity toward ERβ while the (R)-enantiomer demonstrates greater affinity towards ERα. Synthesized as a racemic mixture, (±)-equol exhibits EC50 values of 200 and 74 nM for human ERα and ERβ, respectively and induces breast cancer cell proliferation in vitro at concentrations as low as 100 nM. | [Chemical Properties]
White to Off-White Solid | [Uses]
(R,S)-Equol is a human urinary metabolite of the soy isoflavones Daidzein (D103500). | [Uses]
A human urinary metabolite of Daidzein. It is also a natural estrogenic metabolite from soy isoflavones. | [Application]
(±)-Equol is a metabolite produced in vivo from the soy phytoestrogen daidzein by the action of certain gut microflora, and is a nonsteroidal estrogen of the isoflavonoid class. (±)-Equo has been reported to have estrogenic activity and affinity for estrogen receptors. (±)-Equo can exist in two enantiomeric forms, (S)-equol and (R)-equol. In binding assays, (S)-equol has a higher binding affinity for estrogen β receptors. | [Definition]
ChEBI: 3-(4-Hydroxyphenyl)chroman-7-ol is a member of hydroxyisoflavans. | [Biological Activity]
Metabolite of daidzein. Weak estrogenic agonist, and competitive inhibitor of 17β-estradiol at the estradiol receptor.
(R,S)-Equol is a flavonoid. Racemic mixture. This is a metabolite that is produced in vivo from soy phytoestrogen daidzein from gut microflora. (R,S)-Equol inhibits 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced neoplastic cell transformation by targeting the MEK/ERK/p90RSK/activator protein-1 signalling pathway. (R,S)-Equol shows positive effects on the incidence of prostate cancer. Functions as a DHT blocker. Preferentially activates estrogen receptor β (ERβ). | [Biochem/physiol Actions]
Metabolite of daidzein. Weak estrogenic agonist, and competitive inhibitor of 17β-estradiol at the estradiol receptor. | [Synthesis]
A mixture of compound 3a (0.20 g, 0.78 mmol), n-Bu4NI (1.01 g, 2.73 mmol) and anhydrous CH2Cl2 (5 mL) was stirred and cooled to -78 °C under nitrogen protection. Subsequently, a CH2Cl2 solution of BCl3 (1 M, 2.73 mL, 2.73 mmol) was added dropwise to the cooled mixture. The reaction mixture was stirred and slowly warmed to 0 °C over a period of 2 hours. Upon completion of the reaction, it was carefully quenched with ice water (10 mL), stirring was continued for 20 min, and then neutralized with saturated NaHCO3 solution (10 mL). After vacuum concentration, the residue was extracted with EtOAc (10 mL x 0.5). The organic layers were combined and dried with anhydrous MgSO4. After filtration, the filtrate was concentrated under vacuum and purified by silica gel column chromatography (ethyl acetate/hexane=1:3) to give colorless crystals of estragole 3b (0.18 g, 95% yield). The properties of estragole were as follows: melting point 162-164 °C (literature value 158 °C); thin-layer chromatography Rf value 0.24 (ethyl acetate/hexane=1:3); infrared spectra (KBr) νmax: 3231, 2897, 1598, 1510, 1470, 1366, 1252, 1158, 1119, 826 cm-1; 1H-NMR ( 400 MHz, DMSO-d6) δ: 2.80 (m, 2H, H-3 and H-4a), 3.01 (m, 1H, H-4b), 3.89 (t, J=10.4 Hz, 1H, H-2a), 4.14 (d, J=10.4 Hz, 1H, H-2b), 6.20 (d, J=2.4 Hz, 1H, H-8), 6.29 (dd, J=8.4, 2.4 Hz, 1H, H-6), 6.72 (d, J=8.4 Hz, 2H, H-3', H-5'), 6.86 (d, J=8.4 Hz, 1H, H-5), 7.10 (d, J=8.4 Hz, 2H, H-2', H-6'), 9.18 (s, 1H, OH), 9.29 (s, 1H, OH); 13C-NMR (100 MHz, DMSO-d6) δ: 31.3, 37.2, 70.3, 102.5, 108.0, 112.6, 115.3, 128.3, 130.1, 131.7, 154.5, 156.2, 156.5; electron bombardment mass spectrometry (70 eV) m/z (relative intensities, %): 242 (M+, 58), 135 (25), 134 (40), 123 (88), 120 (100), 107 (39), 91 (37). Calculated elemental analysis (C15H14O3): C 74.36, H 5.82; measured values: C 74.13, H 5.90. | [References]
Equol, a natural estrogenic metabolite from soy isoflavones convenient preparation and resolution of R- and S-equols and their differing binding and biological activity through estrogen receptors alpha and beta
R. S. Muthyala, Y. H. Ju, S. Sheng, L. D. Williams, D. R. Doerge, B. S. Katzenellenbogen, W. G. Helferich, J. A. Katzenellenbogen, Bioorg. Med. Chem. 2004, 12, 1559.
Isolation and identification of new bacterial stains producing equol from Pueraria lobate extract fermentation
J. E. Kwon, J. Lim, I. Kim, D. Kim, S. C. Kang, PLoS ONE 2018, 13, e0192490.
Setchell, K.D.R., Clerici, C., Lephart, E.D., et al. S-equol, a potent ligand for estrogen receptor β, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am. J. Clin. Nutr. 81(5), 1072-1079 (2005).
Liu, H., Du, J., Hu, C., et al. Delayed activation of extracellular-signal-regulated kinase ? is involved in genistein- and equol-induced cell proliferation and estrogen-receptor-α-mediated transcription in MCF-7 breast cancer cells. Journal of Nutritional Biochemistry (2009). |
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