1476-34-2

Usage

Uses

Used in Pharmaceutical Industry:
6-KETOESTRONE is used as a pharmaceutical compound for its involvement in the metabolism of estrogen. It is particularly relevant in the study and treatment of hormone-related conditions and disorders.
Used in Research and Development:
In the field of research and development, 6-KETOESTRONE is used as a biochemical marker for understanding the metabolic pathways of estrogen. It aids in the development of new drugs and therapies targeting hormone-related diseases.
Used in Diagnostic Applications:
6-KETOESTRONE can be used as a diagnostic marker to monitor the levels of estrogen metabolism in the body. This can help in the early detection of hormone imbalances and related health issues.
Used in Hormone Replacement Therapy:
6-KETOESTRONE may be utilized in hormone replacement therapy, particularly for conditions where estrogen levels need to be regulated or balanced.
Used in Endocrinology:
In the field of endocrinology, 6-KETOESTRONE is used to study the effects of estrogen on various physiological processes and to develop targeted treatments for hormone-related disorders.
Used in Toxicology:
6-KETOESTRONE can be employed in toxicology studies to evaluate the potential harmful effects of estrogen metabolites on human health and to develop strategies for mitigating these effects.

InChI:InChI=1/C18H20O3/c1-18-7-6-12-11-3-2-10(19)8-14(11)16(20)9-13(12)15(18)4-5-17(18)21/h2-3,8,12-13,15,19H,4-7,9H2,1H3/t12-,13-,15+,18+/m1/s1

Upstream product

• 571-92-6 6-ketoestradiol 
• 734-32-7 estra-4-ene-3,17-dione 
• 2243-06-3 androst-4-ene-3,6,17-trione 
• 67-56-1 methanol 
• 53-16-7 Estrone 
• 116282-37-2 6-Hydroxy-oestron-3,6-dibenzoat 
• 3434-45-5 6-oxo-3,17β-estradiol diacetate 
• 901-93-9 estrone acetate 
• 7323-89-9 3-acetoxyestra-1,3,5⁽¹⁰⁾-triene-6,17-dione 
• 1091-89-0 estr-5⁽¹⁰⁾-ene-3,6,17-trione 
• 19269-79-5 6-Hydroxy-oestron 

Downstream Products

• 38002-18-5 17α-ethynyl-3,17β-dihydroxyestra-1,3,5(10)-trien-6-one 
• 125363-78-2 (8R,9S,13S,14S,17R)-6,17-Diethynyl-13-methyl-7,8,9,11,12,13,14,15,16,17-decahydro-6H-cyclopenta[a]phenanthrene-3,6,17-triol 
• 69833-90-5 3-hydroxy-13-methyl-8,9,11,12,13,14,15,16-octahydro-7H-cyclopenta[a]phenanthrene-6,17-dione bis-(O-methyl-oxime) 
• 3583-03-7 6β-hydroxyestradiol 

Relevant academic research and scientific papers

Photocatalysis with Quantum Dots and Visible Light: Selective and Efficient Oxidation of Alcohols to Carbonyl Compounds through a Radical Relay Process in Water

Selective oxidation of alcohols to aldehydes/ketones has been achieved with the help of 3-mercaptopropionic acid (MPA)-capped CdSe quantum dot (MPA-CdSe QD) and visible light. Visible-light-prompted electron-transfer reaction initiates the oxidation. The thiyl radical generated from the thiolate anion adsorbed on a CdSe QD plays a key role by abstracting the hydrogen atom from the C?H bond of the alcohol (R1CH(OH)R2). The reaction shows high efficiency, good functional group tolerance, and high site-selectivity in polyhydroxy compounds. The generality and selectivity reported here offer a new opportunity for further applications of QDs in organic transformations.

Modification of estrone at the 6, 16, and 17 positions: Novel potent inhibitors of 17β-hydroxysteroid dehydrogenase type 1

The 17β-hydroxysteroid dehydrogenases (17β-HSDs) catalyze the interconversion between the oxidized and reduced forms of androgens and estrogens at the 17 position. The 17β-HSD type 1 enzyme (17β-HSD1) catalyzes the reduction of estrone to estradiol and is

C(10)-C(19) bond cleavage reaction of 19-oxygenated androst-4-ene-3,6-dione steroids under various conditions

C(10)-C(19) bond cleavage reaction of 19-hydroxy- and 19-oxoandrost-4-ene- 3,6,17-triones (5, 6) was explored under various conditions. Treatment of steroids 5 and 6 with KOH in MeOH gave the A-ring aromatized product 6-oxoestrone (11) in a fair yield, respectively, in contrast, the treatment with a weak base yielded 4-methyl steroid 17 (20%) in the case of 19-alcohol 5 or 19-nor- Δ5(10)-steroid 9 (12-67%) along with compound 11 (6-27%) in the case of 19-aldehyde 6. Reaction of compound 6 with HCl in MeOH produced 3-methyl ethers of 6-oxoestrone and Δ6-estrone, compounds 12 and 14 (ca. 20% each). Thus, 6-oxosteroids 5 and 6 showed unique C(10)-C(19) bond cleavage reactions with a base or acid.

Aromatization of 19-Oxygenated Androst-4-ene-3,6,17-triones with Human Placental Microsomes

To gain insight into the aromatization sequence of androst-4-ene-3,6,17-trione (1), a suicide substrate of aromatase, the aromatization of its 19-hydroxy and 19-oxo analogs 2 and 3 with human placental microsomes, was studied using GC-MS. Steroids 2 and 3 were separately incubated with the microsomes in the presence of NADPH in air. The GC-MS analysis of the trimethylsilyl derivative of the aromatization product indicated that both the 19-oxygenated steroids 2 and 3 were aromatized to yield 6-oxoestrogens, 6-oxoestrone (4) and 6-oxoestradiol (5), in each experiment. The aromatization rates of substrates 2 and 3 were 605+/-48 and 1794+/-75 pmol/mg protein/10 min, respectively. These relatively higher rates, compared to that of the parent steroid 1 (73.2+/-6.6 pmol/mg protein/10 min), indicates that the suicide substrate 1 is aromatized through the 19-oxygenated intermediates 2 and 3.

Biochemical studies of estr-4-ene-3,6,17-trione and 5α-androstan-17-ones with or without a carbonyl function at C-3 and/or C-6 as aromatase inhibitors

19-Nor (2) and 5α-reduced (3) derivatives of androst-4-ene-3,6,17-trione (1) as well as 5α-androstan-17-ones 4-6 were tested for their abilities to inhibit aromatase in human placental microsomes. All the steroids except 5α-6-one 4 were fair to good competitive inhibitors of the enzyme, with apparent K(i)'s ranging from 50 to 820 nM in which 5α-3-one 5 was the most potent among them. The inhibitory activities of the 19-nor and 5α-reduced derivatives (2 and 3) were less potent than that of the parent compound 1. Inhibitor 2 caused a time-dependent, pseudo-first-order inactivation of aromatase activity with a rate constant for inactivation of 0.148 min-1 in the presence of NADPH in air. The substrate androstenedione prevented the inactivation and L-cysteine did not protect aromatase from the inactivation.

A Novel Efficient Approach to the Synthesis of 6-Oxo Ethinylestradiol and its 3-Isopropanesulfonate

Ethinylestradiol (1) was converted into the corresponding 6-oxo derivative 7 by a short and simple procedure involving acetate 10 and ketone 11.Phase transfer catalyzed esterification of compound 7 with propane-2-sulfonyl chloride gave sulfonate 12.