53866-34-5

Usage

Chemical Properties

White Solid

Uses

Isotope labelled Estrone (E889050), which is a metabolite of 17β-Estradiol (E888000). During the metabolism, it is in rapid equilibrium with Estriol (E888960) and 17β-Estradiol (E888000) (1). Causes the feminization of male fish at human and animal waste sites (2).Drinking water contaminant candidate list 3 (CCL 3) compound as per United States Environmental Protection Agency (EPA), environmental, and food contaminants.

InChI:InChI=1/C18H22O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-16,19H,2,4,6-9H2,1H3/t14-,15-,16+,18+/m1/s1/i3D,7D2,10D

Upstream product

• 56588-58-0 16,16-di-deuterium-estra-1,3,5⁽¹⁰⁾-triene-17-one 
• 53-16-7 Estrone 

Downstream Products

• 443791-75-1 2,4,16,16-D₄-estrone-3-oleate 
• 221093-45-4 2,4,16,16,17-²H-estradiol-17β 
• 916818-36-5 2,4,16,16,17α-D5-estradiol-3,17-distearate 
• 916818-37-6 2,4,16,16,17α-D5-estradiol-3,17-dioleate 
• 916818-38-7 2,4,16,16,17α-D5-estradiol-3,17-dilinoleate 
• 916818-35-4 2,4,16,16,17α-D5-estradiol-3,17-dipalmitate 
• 66789-03-5 17-β-estradiol-2,4,16,16-d₄ 

Relevant academic research and scientific papers

Expedient microwave deuteration of estrone in CF3COOD

A rapid and efficient deuteration procedure was developed for estrone. Irradiation of estrone in CF3COOD in a microwave oven gave [2,4,16,16-2H4]-estrone in 95% yield. Ultrasound and CF3COOD reflux deuterations of estrone were also studied.

Estrone and estradiol metabolism in vivo in human breast cysts

Fibrocystic disease of the breast manifesting palpable cysts express breast cyst fluids frequently containing estrogen sulfates at concentrations far exceeding those found in sera of the patient. The study explored the potential of the breast cyst to synthesize some of these estrogen sulfates. Deuterated estrone and estradiol were synthesized and either (estradiol, 4 cases or estrone, 2 cases) was injected into a cyst. The cyst was aspirated at approximately 0, 4 and 8 h, the target being 1 ml, 50% and complete aspiration respectively. Metabolites were purified sequentially by ether extraction, enzymatic hydrolysis of estrogen conjugates, chromatography on Sephadex LH 20 and identified by gas chromatography linked to mass spectrometry. The unconjugated fraction isolated from the ether extract was subjected to the same purification and detection scheme. Among the conjugates, deuterated estrone sulfate was the major metabolite of either precursor in all studies, while estradiol sulfate was not detected in any of the 6 experiments. The sulfate fractions also yielded traces of 16α-hydroxyestrone (2 studies), 4-hydroxyestrone (4 studies) and 2-hydroxyestrone (1 study). In the unconjugated fraction, one study with deuterated estradiol, 4- hydroxyestrone was obtained. In one study with deuterated estrone, traces of 2-hydroxyestrone and 16α- hydroxyestrone were obtained. These novel data are significant because patients with fibrocystic disease are at slightly elevated risk for developing breast cancer and 16α-hydroxyestrone and 4- hydroxyestrone are reported carcinogens. (C) 2000 Elsevier Science Inc.