134223-97-5

Usage

InChI:InChI=1/C19H26O5S.C5H5N/c1-19-8-3-4-17(19)15-11-18(24-25(20,21)22)16-10-12(23-2)5-6-13(16)14(15)7-9-19;1-2-4-6-5-3-1/h5-6,10,14-15,17-18H,3-4,7-9,11H2,1-2H3,(H,20,21,22);1-5H/t14?,15?,17?,18?,19-;/m0./s1

Upstream product

• 26412-87-3 sulfur trioxide pyridine complex 
• 134223-94-2 6α-hydroxy-3-methoxyestra-1,3,5(10)-triene 
• 5976-59-0 estra-1,3,5⁽¹⁰⁾-trien-3-yl acetate 
• 22838-04-6 3-hydroxyestra-1,3,5⁽¹⁰⁾-trien-6-one 
• 22837-97-4 3-methoxyestra-1,3,5⁽¹⁰⁾-trien-6-one 
• 22838-01-3 3-acetoxyestra-1,3,5⁽¹⁰⁾-trien-6-one 
• 53-63-4 17-deoxyestrone 

Relevant academic research and scientific papers

Synthesis and mechanism of hydrolysis of estrogen 6-sulfates: Model compounds for demonstrating the carcinogenesis of estrogen

To investigate the carcinogenesis of estrogen with respect to the chemical behavior of estrogen 6-sulfates, two epimeric 6-sulfates, pyridinium 3-methoxyestrα-1,3,5(10)-trien-6α-yl (8) and -6β-yl (11) Sulfates, were synthesized as the model compounds, and their chemical reactivities were examined. These sulfates were shown to he highly reactive: in water, they were readily and quantitatively converted to a common product mixture, composed of 3-methoxyestra-1,3,5(10)-trien-6α-ol (6) and -6β-ol (9) in an almost constant product ratio, with a predominant yield of the latter. The hydrolysis of both sulfates 8 and 11 proceeded in first-order kinetics with half-lives of 1.1 and 1.5 minutes, respectively. When the sulfates were hydrolyzed in 18O-water, the heavy-oxygen atom was shown to he incorporated quantitatively into the C-6 position of the products. These results demonstrate that estrogen 6-sulfates generate a highly reactive benzylic (C-6) carbocation in an aqueous solution, suggesting that the sulfates can act as carcinogens.