3131-23-5 Usage
Description
4-HYDROXYESTRONE, also known as a metabolite of Estradiol, is a 4-hydroxy steroid that is estrone substituted by a hydroxy group at position 4. It is characterized by its pale yellow solid appearance and plays a significant role in various biological processes.
Uses
Used in Pharmaceutical Industry:
4-HYDROXYESTRONE is used as a pharmaceutical compound for its potential role in hormone regulation and treatment of hormone-related conditions. Its ability to modulate hormone levels makes it a promising candidate for therapeutic applications.
Used in Research and Development:
As a metabolite of Estradiol, 4-HYDROXYESTRONE is used as a research compound to study the effects of hormones on various physiological processes. This helps in understanding the underlying mechanisms of hormone action and developing targeted therapies for related conditions.
Used in Hormone Replacement Therapy:
4-HYDROXYESTRONE is used as a hormone replacement agent for conditions where there is an imbalance in hormone levels, such as menopause or andropause. Its ability to regulate hormone levels can help alleviate symptoms and improve overall health.
Used in Endocrine Disruption Studies:
Due to its structural similarity to natural hormones, 4-HYDROXYESTRONE is used as a model compound in endocrine disruption studies. This helps researchers understand the potential effects of environmental chemicals on hormone regulation and develop strategies to mitigate their impact.
Used in Drug Development:
4-HYDROXYESTRONE serves as a key intermediate in the synthesis of various steroidal drugs. Its unique chemical properties make it a valuable starting material for the development of new pharmaceuticals with potential applications in treating hormone-related disorders.
Hazard
A reproductive hazard.
Biochem/physiol Actions
4-Hydroxyestrone is an endogenous estrogen metabolite, which exhibits a strong neuroprotective effect against oxidative damage. It also provides effective protection against kanic acid-induced hippocampal oxidative damage in rats when compared to 17β-estradiol. 4-Hydroxyestrone regulates the angiogenic process during corpus luteum formation. It might be involved in an increased risk of cancer. 4-Hydroxyestrone is found in the early and mid-luteal phases.
Check Digit Verification of cas no
The CAS Registry Mumber 3131-23-5 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,1,3 and 1 respectively; the second part has 2 digits, 2 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 3131-23:
(6*3)+(5*1)+(4*3)+(3*1)+(2*2)+(1*3)=45
45 % 10 = 5
So 3131-23-5 is a valid CAS Registry Number.
InChI:InChI=1/C18H22O3/c1-18-9-8-11-10-4-6-15(19)17(21)13(10)3-2-12(11)14(18)5-7-16(18)20/h4,6,11-12,14,19,21H,2-3,5,7-9H2,1H3/t11-,12-,14+,18+/m1/s1
3131-23-5Relevant articles and documents
Reactions of 3,4-estrone quinone with mimics of amino acid side chains
Abul-Hajj, Yusuf J.,Tabakovic, Katmerka,Gleason, William B.,Ojala, William H.
, p. 434 - 438 (1996)
Reaction of 3,4-estrone o-quinone (3,4-EQ) with several amino acid side chain mimics, including 4-ethylphenol, 4-methylimidazole, acetic acid, and propanethiol, gave a mixture of several products including the catechol, Michael addition products, and dime
Synthesis of the catechols of natural and synthetic estrogens by using 2-iodoxybenzoic acid (IBX) as the oxidizing agent
Saeed, Muhammad,Zahid, Muhammad,Rogan, Eleanor,Cavalieri, Ercole
, p. 173 - 178 (2007/10/03)
A method for the synthesis of 2-hydroxyestrone/estradiol, 4-hydroxyestrone/estradiol, 3′-hydroxydiethylstilbestrol, 3′-hydroxyhexestrol, and 3′-hydroxydienestrol is reported, in which 2-iodoxybenzoic acid (IBX) and the corresponding phenolic estrogen are reacted. Treatment of the natural estrogens, estrone/estradiol, with stoichiometric amounts of IBX in dimethylformamide initially yielded a mixture of estrone/estradiol-2,3- and -3,4-quinones, which were reduced in situ to the corresponding catechols by treatment with a 1 M aqueous solution of ascorbic acid. Chromatographic separation of the reaction products afforded 2- and 4-hydroxyestrone/estradiol in good overall yields (79%). In the case of the synthetic estrogens containing two identical phenolic rings, protection of one ring is a prerequisite for the synthesis of the monocatechol. Thus, diethylstilbestrol and dienestrol were protected at one phenol ring as their methyl ethers. The resulting monophenols were treated with stoichiometric amounts of IBX for 1 h, followed by treatment with 1 M aqueous ascorbic acid to obtain the corresponding catechols in more than 70% yield. Furthermore, the catechol of diethylstilbestrol, protected at one ring, was reduced by catalytic hydrogenation at the C3-C4 double bond to obtain 3′-hydroxyhexestrol in 90% yield. Removal of the protected methoxy groups of the synthetic estrogen catechols was carried out by treatment with a 1 M solution of boron tribromide in dichloromethane. This method is highly efficient for the preparative scale synthesis of catechols of both natural and synthetic estrogens.
