531-95-3 Usage
Description
Equol is a human urinary metabolite of Daidzein, a natural estrogenic metabolite derived from soy isoflavones. It is also a metabolite of the soy isoflavones Daidzein and Genistein, with significant biological actions. Equol is a white to off-white solid and possesses receptor binding activity and serine protease properties.
Uses
Used in Pharmaceutical Industry:
Equol is used as a pharmaceutical agent for its estrogenic properties and receptor binding activity. It has potential applications in hormone regulation and treatment of conditions related to estrogen deficiency or imbalance.
Used in Nutritional Supplements:
Equol is used as an ingredient in nutritional supplements for its potential health benefits, including hormone regulation and support for overall well-being.
Used in Research and Development:
Equol is used as a research compound for studying its biological actions and potential applications in various fields, such as endocrinology, pharmacology, and biochemistry.
Used in Food Industry:
Equol can be used as an additive in the food industry, particularly in products that aim to provide health benefits related to hormone regulation and overall well-being.
Used in Cosmetics Industry:
Equol may be used in the cosmetics industry for its potential benefits in hormone regulation and skin health, potentially leading to the development of skincare products with Equol as an active ingredient.
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]
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.
Check Digit Verification of cas no
The CAS Registry Mumber 531-95-3 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 1 respectively; the second part has 2 digits, 9 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 531-95:
(5*5)+(4*3)+(3*1)+(2*9)+(1*5)=63
63 % 10 = 3
So 531-95-3 is a valid CAS Registry Number.
InChI:InChI=1/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
531-95-3Relevant articles and documents
A Concise Enantiodivergent Synthesis of Equol
Uemura, Takahito,Saito, Yusuke,Sonoda, Motohiro,Tanimori, Shinji
, p. 693 - 696 (2020/12/23)
Equol, a nonsteroidal estrogen produced from the metabolism of the isoflavonoid phytoestrogen daidzein, has been synthesized as both enantioenriched forms based on MacMillan's α-Arylation of carbonyl compound mediated by amino acid derived indazolidinones and copper precatalysts. The natural form of (S)-equol and its enantiomer (R)-equol have been synthesized in 8 steps from 2,4-dimethoxybenzaldehyde with good enantiomeric purity (90% ee and 90% ee, respectively).
Method for preparing equol
-
, (2020/01/08)
The invention relates to a method for preparing equol. The method comprises the following steps: S1, synthesizing benzohydropyran: namely weighing daidzein raw materials, dissolving the daidzein raw materials in dimethyl formamide (DMF), adding palladium carbon into a hydrogenation kettle, carrying out reacting at a same speed under constant temperature and constant pressure, filtering out the catalyst, adding ice water into the filtrate, carrying out stirring to separate out white solid, and carrying out filtering, water washing and drying to obtain an intermediate a; S2, synthesizing a condensate: namely adding the intermediate a, dichloroethane and polyphosphoric acid into a three-mouth bottle, carrying out a reflux reaction, carrying out cooling, adding the obtained substance into icewater, taking an organic phase by layering, carrying out drying with sodium sulfate, concentrating dichloroethane to obtain a yellow oily substance, and carrying out recrystallizing with 90% ethanol water to obtain an intermediate b; and S3, synthesizing equol: namely adding the intermediate b, DMF and a catalyst into a hydrogenation kettle, filtering out the catalyst after a reaction at constanttemperature and constant pressure, adding the filtrate into ice water, carrying out stirring to separate out a gray solid, carrying out filtering, and recrystallizing the filter cake with 70% methanolwater to obtain the equol. The method has the advantages of simple steps, high total yield, environmental protection and easy operation.
Enantioselective Total Synthesis of Natural Isoflavans: Asymmetric Transfer Hydrogenation/Deoxygenation of Isoflavanones with Dynamic Kinetic Resolution
Ke?berg, Anton,Lübken, Tilo,Metz, Peter
, p. 3006 - 3009 (2018/05/28)
A concise and highly enantioselective synthesis of structurally diverse isoflavans from a single chromone is described. The key transformation is a single-step conversion of racemic isoflavanones into virtually enantiopure isoflavans by domino asymmetric transfer hydrogenation/deoxygenation with dynamic kinetic resolution.