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).
Rhodium-catalyzed asymmetric addition of arylboronic acids to 2: H-chromenes leading to 3-arylchromane derivatives
Umeda, Moeko,Sakamoto, Kana,Nagai, Tomotaka,Nagamoto, Midori,Ebe, Yusuke,Nishimura, Takahiro
supporting information, p. 11876 - 11879 (2019/10/11)
Asymmetric addition of arylboronic acids to 2H-chromenes proceeded in the presence of a hydroxorhodium/chiral diene catalyst to give 3-arylchromanes in high yields with high enantioselectivity. The reaction involves 1,4-Rh shift before protonation to release the addition product and to regenerate the hydroxorhodium species.
A chiral pool approach for asymmetric syntheses of both antipodes of equol and sativan
Yalamanchili, Chinni,Chittiboyina, Amar G.,Chandra Kumar Rotte, Sateesh,Katzenellenbogen, John A.,Helferich, William G.,Khan, Ikhlas A.
, p. 2020 - 2029 (2018/03/21)
For the first time, both antipodes of the isoflavans, equol and sativan were synthesized in >98% ee with good overall yields starting from readily available starting materials. The chiral isoflavan, (?)-equol is produced from soy isoflavones, formonentin and daidzein by the action of intestinal bacteria in certain groups of population and other chiral isoflavans are reported from various phytochemical sources. To produce these chiral isoflavans in gram quantities, Evans’ enantioselective aldol condensation was used as a chiral-inducing step to introduce the required chirality at the C-3 position. Addition of chiral boron-enolate to substituted benzaldehyde resulted in functionalized syn-aldol products with >90% yield and excellent diastereoselectivity. Functional group transformations followed by intramolecular Mitsunobu reaction and deprotection steps resulted the target compounds, S-(?)-equol and S-(+)-sativan, with high degree of enantiopurity. By simply switching the chiral auxiliary to (S)-4-benzyloxazolidin-2-one and following the same synthetic sequence the antipodes, R-(+)-equol and R-(?)-sativan were achieved. Both enantiomers are of interest from a clinical and pharmacological perspective and are currently being developed as nutraceutical and pharmacological agents. This flexible synthetic process lends itself quite readily to the enantioselective syntheses of other biologically active C-3 chiral isoflavans.