20823-11-4

Basic information

• Product Name: (17beta)-2,4-dinitroestra-1(10),2,4-triene-3,17-diol
• CAS NO: 20823-11-4
• Molecular Formula: C₁₈H₂₂N₂O₆
• Molecular Weight: 362.3771
• Mol File: 20823-11-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 466.2°C at 760 mmHg
• Flash Point: 184.8°C
• Density: 1.413g/cm³
• Vapor Pressure: 1.71E-09mmHg at 25°C
• Refractive Index: 1.642
• CAS DataBase Reference: (17beta)-2,4-dinitroestra-1(10),2,4-triene-3,17-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (17beta)-2,4-dinitroestra-1(10),2,4-triene-3,17-diol(20823-11-4)
• EPA Substance Registry System: (17beta)-2,4-dinitroestra-1(10),2,4-triene-3,17-diol(20823-11-4)

Safety Data

• Hazardous Substances Data: 20823-11-4(Hazardous Substances Data)

Usage

General Description

(17beta)-2,4-dinitroestra-1(10),2,4-triene-3,17-diol is a synthetic compound with a chemical structure and properties similar to natural estrogen hormones. It is specifically a form of estradiol, a hormone that plays a key role in the regulation of the female reproductive system and secondary sexual characteristics. (17beta)-2,4-dinitroestra-1(10),2,4-triene-3,17-diol is often used in scientific research and medical applications to study the effects of estrogen on the body, such as its role in breast development, menstrual cycles, and bone density. It can also be utilized in hormone replacement therapy to alleviate symptoms associated with menopause and other hormonal imbalances. Additionally, its chemical structure makes it useful in the development of new pharmaceuticals and treatments for hormone-related disorders.

Upstream product

• 50-28-2 estradiol 
• 42979-83-9 2,4-dinitro-3-hydroxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 6936-94-3 4-Nitroestratriene-3,17beta-diol 
• 6298-51-7 2-Nitroestratriene-3,17beta-diol 

Relevant articles and documents

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17beta-Estradiol nitration by peroxidase/H2O2/NO2-: a chemical assessment.

Nitration of 17beta-estradiol by H(2)O(2) and nitrite in the presence of various peroxidases, viz. horseradish peroxidase, lactoperoxidase, and peroxidase-containing homogenates from bovine uteri, was systematically investigated to assess on a chemical basis its potential relevance to the mechanisms of impairment of estrogen functions under oxidative/nitrosative stress conditions. In the presence of excess nitrite 17beta-estradiol reacted smoothly to give 2-nitroestradiol (1), 4-nitroestradiol (2), and 2,4-dinitroestradiol (3). With 10-300 microM estradiol, formation yields of 1-3 were 12-55%, but dropped to 1% or less at lower estrogen concentration, for example, 1 microM, or in plasma as the reaction medium. Time course analysis showed that 2 is the prevalent nitration product under conditions of slow generation of nitrating species, suggesting some regioselectivity for estradiol nitration at C-4, whereas 1 prevails with bolus addition of reagents, due to faster degradation of 2. Competition experiments carried out with (15)NO(2)- showed that 2 is about twice more susceptible to nitration than 1 as determined by (15)N NMR analysis of the resulting 3. The biological effects of 1 and 2 were preliminarily tested on in vitro bovine embryo cultures. When 1 and 2 were substituted to the standard 17beta-estradiol in the oocyte maturation, a significant decrease in both cleavage and blastocyst efficiency was observed in the case of 1 but not 2. Overall, these results suggest that estradiol nitration is a potential pathway of hormonal dysfunction and toxicity but would require elevated estrogen levels of questionable physiological relevance.

Reductive N -alkylation of nitroarenes: A green approach for the N-alkylation of natural products

A simple, mild, cost-effective, and green approach for the reductive mono-N-alkylation of nitroarenes has been developed. HOAc/Zn are utilized as the reducing system together with a carbonyl compound as an alkyl source in methanol. Excellent yields were obtained with stoichiometric control of mono- over dialkylated products. Application to five complex natural products demonstrated the practical utility of the method.