40822-17-1

Basic information

• Product Name: (16E)-16-(hydroxyimino)-3-methoxyestra-1,3,5(10)-trien-17-one
• Synonyms: 3-Methoxyestra-1,3,5(10)-triene-16,17-dione 16-oxime
• CAS NO: 40822-17-1
• Molecular Formula: C₁₉H₂₃NO₃
• Molecular Weight: 313.3908
• Mol File: 40822-17-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 492.104°C at 760 mmHg
• Flash Point: 251.416°C
• Density: 1.341g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.659
• CAS DataBase Reference: (16E)-16-(hydroxyimino)-3-methoxyestra-1,3,5(10)-trien-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: (16E)-16-(hydroxyimino)-3-methoxyestra-1,3,5(10)-trien-17-one(40822-17-1)
• EPA Substance Registry System: (16E)-16-(hydroxyimino)-3-methoxyestra-1,3,5(10)-trien-17-one(40822-17-1)

Safety Data

• Hazardous Substances Data: 40822-17-1(Hazardous Substances Data)

Usage

Description

(16E)-16-(hydroxyimino)-3-methoxyestra-1,3,5(10)-trien-17-one is a synthetic derivative of estrone, a naturally occurring estrogen hormone. It features a hydroxyimino group at the 16th carbon position and a methoxy group at the 3rd carbon position of the estrane skeleton.
Used in Scientific Research:
(16E)-16-(hydroxyimino)-3-methoxyestra-1,3,5(10)-trien-17-one is used as a research tool for studying estrogen receptor binding and activity.
Used in Pharmaceutical Development:
(16E)-16-(hydroxyimino)-3-methoxyestra-1,3,5(10)-trien-17-one is used as a potential candidate in the development of novel pharmaceuticals for the treatment of hormone-related conditions, such as menopausal symptoms and certain types of cancer.
Used in Synthesis of Estrogen Derivatives:
(16E)-16-(hydroxyimino)-3-methoxyestra-1,3,5(10)-trien-17-one is used as a starting material for the synthesis of other estrogen derivatives with desired pharmacological properties.

Upstream product

• 1624-62-0 estrone 3-methyl ether 
• 110-46-3 isopentyl nitrite 

Downstream Products

• 24721-15-1 3-methoxy-17β-hydroxy-estra-1,3,5(10)-trien-16-one 
• 1417413-84-3 C₂₇H₂₈N₂O₃ 

Relevant articles and documents

Enolate-Based Regioselective Anti-Beckmann C-C Bond Cleavage of Ketones

The Baeyer-Villiger or Beckmann rearrangements are established methods for the cleavage of ketone derivatives under acidic conditions, proceeding for unsymmetrical precursors selectively at the more substituted site. However, the fragmentation regioselectivity cannot be switched and fragmentation at the less-substituted terminus is so far not possible. We report here that the reaction of ketone enolates with commercial alkyl nitrites provides a direct and regioselective way of fragmenting ketones into esters and oximes or ω-hydroxyimino esters, respectively. A comprehensive study of the scope of this reaction with respect to ketone classes and alkyl nitrites is presented. Control over the site of cleavage is gained through regioselective enolate formation by various bases. Oxidation of kinetic enolates of unsymmetrical ketones leads to the otherwise unavailable "anti-Beckmann"cleavage at the less-substituted side chain, while cleavage of thermodynamic enolates of the same ketones represents an alternative to the Baeyer-Villiger oxidation or the Beckmann rearrangement under basic conditions. The method is suited for the transformation of natural products and enables access to orthogonally reactive dicarbonyl compounds.

Synthesis of 16,17-seco-steroids with iminomethyl-2-pyridine and aminomethylene-2-pyridine structures as chiral ligands for copper ions and molecular oxygen activation

Starting from 16-oximino-3-methoxy-estra-1.3.5(10)-trien-17-one, the 16,17-seco-13α-carbaldehyde with a 16-nitrile function and its corresponding carboxylic acid have been synthesized via a Beckmann fragmentation. The corresponding 13α-amine is available by Curtius degradation of the carboxylic acid. Condensation of the carboxaldehyde with 2-(aminomethyl)pyridine and the primary amine with pyridine-2-carboxaldehyde gave the corresponding iminomethyl-2-pyridine and the aminomethylene-2-pyridine compounds. Copper-mediated ligand hydroxylations with molecular oxygen were not successful. Reasons for this are discussed.