| Identification | More | [Name]
Equol | [CAS]
531-95-3 | [Synonyms]
4',7-DIHYDROXYISOFLAVAN
4',7-ISOFLAVANDIOL
7,4'-ISOFLAVANDIOL
R,S-EQUOL
(S)-3,4-DYHYDRO-3-(4-HYDROXYPHENYL)-2H-1-BENZOPYRAN-7-OL
(S)-4',7-DIHYDROXYISOFLAVANCE
(S)-3,4-dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol
(S)-EQUOL
(S)-3-(4-Hydroxy-phenyl)-chroman-7-ol
3-(4-Hydroxy-phenyl)-chroman-7-ol
(3S)-3-(4-hydroxyphenyl)chroman-7-ol
EQUOL, (+/-)-(SH)
EQUOL/()-4'',7-ISOFLAVANDIOL
(S)-(-)-4',7-Isoflavandiol
(3S)-3-(4-Hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol
(3S)-Equol | [EINECS(EC#)]
208-522-2 | [Molecular Formula]
C15H14O3 | [MDL Number]
MFCD00200962 | [Molecular Weight]
242.27 | [MOL File]
531-95-3.mol |
| Chemical Properties | Back Directory | [Appearance]
White to Off-White Solid | [Melting point ]
189-190°C | [alpha ]
D -21.5° | [Boiling point ]
312.25°C (rough estimate) | [density ]
1.1914 (rough estimate) | [refractive index ]
1.5557 (estimate) | [storage temp. ]
Inert atmosphere,2-8°C | [solubility ]
DMSO (Soluble), Ethanol (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
9.94±0.40(Predicted) | [color ]
White to Pale Yellow | [Usage]
A human urinary metabolite of Daidzein. It is also a natural estrogenic metabolite from soy isoflavones | [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 | [InChIKey]
ADFCQWZHKCXPAJ-GFCCVEGCSA-N | [SMILES]
C1OC2=CC(O)=CC=C2C[C@H]1C1=CC=C(O)C=C1 | [CAS DataBase Reference]
531-95-3(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
S-equol is a metabolite of dietary soy isoflavone daidzein by gut microbiome and possesses the most anti-atherogenic properties among all isoflavones.
| [Chemical Properties]
White to Off-White Solid | [Uses]
(S)-Equol and R-Equol are metabolites of the soy isoflavones Daidzein (D103500) and Genistein. Both have significant biological actions. | [Uses]
A human urinary metabolite of Daidzein. It is also a natural estrogenic metabolite from soy isoflavones | [Uses]
Receptor; binding activity | [Uses]
serine protease | [Definition]
ChEBI: Equol is a member of hydroxyisoflavans. | [Biological Activity]
equol is an isoflavan produced by intestinal bacteria in response to soy isoflavone intake in human. it shows a wide range of activities including antioxidant activity, anti-inflammation activity and anticancer activity. it is reported that equol specifically binds to 5α-dht and has a modest affinity for recombinant estrogen receptor erβ, which may be responsible for most of equol’s biological properties. [1] | [Synthesis]
Dimethoxybenzodihydropyran (S)-23 (18 g, 66.7 mmol) was dissolved in pyridine hydrochloride (192 g, 148 mL, 1.67 mol), and the reaction mixture was heated at 150 °C overnight and then cooled to room temperature. The reaction solution was neutralized with excess aqueous NaHCO3 and subsequently extracted with dichloromethane (3 x 100 mL). The organic phases were combined and the crude product was purified by column chromatography (eluent: hexane/diethyl ether mixed solvent) to afford (S)-3-(4-hydroxyphenyl)benzodihydropyran-7-ol as a white solid in 88% yield (14.2 g, 58.7 mmol). The product characterization data were as follows: [α]25D = -19.5 (c = 1.05, MeOH), literature value [α]25D = -13 (c = 0.21, ethanol); 1H NMR (400 MHz, CD3OD) δ 7.09 (d, J = 8.5 Hz, 2H), 6.88 (d, J = 8.2 Hz, 1H), 6.76 (d, J = 8.5 Hz, 2H), 6.33 (dd, J = 8.2, 2.5 Hz, 1H), 6.25 (d, J = 2.5 Hz, 1H), 4.20 (tdd, J = 10.5, 3.6, 1.8 Hz, 1H), 3.91 (t, J = 10.5 Hz, 1H), 3.05 (tdd, J = 10.2, 6.0, 3.6 Hz, 1H). 2.93-2.77 (m, 2H); 13C NMR (100 MHz, CD3OD) δ 157.6, 157.3, 156.3, 133.8, 131.2, 129.3 (2C), 116.4 (2C), 114.6, 109.1, 103.8, 72.2, 39.4, 33.0. | [Physiological effects]
(S)-Equol is a selective estrogen receptor β (ERβ) agonist with lower binding activity for ERα, the predominant estrogen receptor in the breast and uterus. ERβ is highly expressed in hippocampal neurons.
| [in vitro]
in vitro studies were conducted to measure both the binding affinity of equol for 5alpha-dihydrotestosterone (5alpha-dht) and the effects of equol treatment in human prostate cancer (lncap) cells. it was found that equol bound to 5alpha-dht with maximum and half maxim concentrations of 100 nm and 4.8 nm, respectively. in addition, equol significantly offset the increases in psa levels from lncap cells. [1] | [in vivo]
an in vivo study was performed to investigate effects of equol on rat prostate weight and circulating levels of sex steroid hormones. 1.0 mg/kg of equol was injected to long-evans rats fed with a low isoflavone diet for 25 days. findings from this study suggested that equol significantly decreased rat prostate weights and down-regulated serum levels of 5alpha-dht. however, this agent did not alter levels of lh, testosterone and estradiol. [1] | [storage]
-20°C | [References]
[1]lund td, blake c, bu l, hamaker an, lephart ed. iequol an isoflavonoid: potential for improved prostate health, in vitro and in vivo evidence. reprod biol endocrin. 2011; 9(4): doi: 10.1186/1477-7827-9-4.
[2]setchell dr and clerici c. equol: pharmacokinetics and biological actions. j nutr. 2010 jul; 140(7): 1363s–8s. |
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