(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

CAS DataBase Reference

531-95-3(CAS DataBase Reference)

Safety Information

WGK Germany 

3

F 

3-10

MSDS

• Language:English Provider:(S)-3,4-Dihydro-3-(4-hydroxyphenyl)-2H-1-benzopyran-7-ol
• Language:English Provider:SigmaAldrich

(S)-Equol Usage And Synthesis

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

serine protease

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.

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.

(S)-Equol(531-95-3)Related Product Information

• Dihydromyrcenol
• Hydroxy silicone oil
• Triphenylphosphine
• Tetrahydro-4H-pyran-4-one
• Centchroman
• 2-Phenylphenol
• Aspartame
• TRIFOLIRHIZIN
• Rotenone
• MEDICARPIN
• morelloflavone
• Phenylacetone
• Phenoxodiol
• pisatin
• 4',7-DIMETHOXYISOFLAVANONE
• Dihydrodaidzein
• Phaseollin
• (-)-TEPHROSIN