(S)-Equol CAS 531-95-3
(S)-Equol Basic information
| Product Name: | (S)-Equol |
| Synonyms: | (S)-3,4-DYHYDRO-3-(4-HYDROXYPHENYL)-2H-1-BENZOPYRAN-7-OL;(S)-4',7-DIHYDROXYISOFLAVANCE;R,S-EQUOL;(-)-(S)-EQUOL;S,R-equol;3-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-7-ol;4',7-ISOFLAVANDIOL;4',7-DIHYDROXYISOFLAVAN |
| CAS: | 531-95-3 |
| MF: | C15H14O3 |
| MW: | 242.27 |
| EINECS: | 208-522-2 |
| Product Categories: | Inhibitors;Iso-Flavones;Chiral Reagents;Heterocycles;Metabolites & Impurities;Metabolites |
| Mol File: | 531-95-3.mol |
(S)-Equol Chemical Properties
| 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) |
| pka | 9.94±0.40(Predicted) |
| form | Solid |
| color | White to Pale Yellow |
| Cosmetics Ingredients Functions | HAIR CONDITIONING SKIN CONDITIONING ANTIOXIDANT |
| 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) |
Safety Information
| WGK Germany | 3 |
| F | 3-10 |
| Storage Class | 11 - Combustible Solids |
| 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 | Receptor; binding activity |
| Uses | A human urinary metabolite of Daidzein. It is also a natural estrogenic metabolite from soy isoflavones |
| Uses | (S)-Equol and R-Equol are metabolites of the soy isoflavones Daidzein (D103500) and Genistein. Both have significant biological actions. |
| Definition | ChEBI: Equol is a member of hydroxyisoflavans. |
| benefits | S-equol(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 . The hippocampus plays a major role in the brain for memory and spatial orientation. Thus, a selective ERβ agonist, such as S-equol, could offer a safe therapeutic or dietary supplement for cognitive improvement. |
| Biological Activity | (S)-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] |
| Side effects | (S)-Equol(EQUOL) can cause some mild side effects such as constipation and bloating. |
| Synthesis | 3722-56-3 531-95-3 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] |
| 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. |
(S)-Equol Preparation Products And Raw materials
| Raw materials | 2H-1-Benzopyran, 3,4-dihydro-7-(methoxymethoxy)-3-[4-(methoxymethoxy)phenyl]-, (3S)--->(3S)-3,4-Dihydro-7-methoxy-3-(4-methoxyphenyl)-2H-1-benzopyran-->1383121-33-2 |
