17503-05-8

Basic information

• Product Name: (4alpha,5alpha)-4,5-epoxypregnane-3,20-dione
• CAS NO: 17503-05-8
• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.4611
• Mol File: 17503-05-8.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 458.4°C at 760 mmHg
• Flash Point: 200°C
• Density: 1.16g/cm³
• Vapor Pressure: 1.38E-08mmHg at 25°C
• Refractive Index: 1.553
• CAS DataBase Reference: (4alpha,5alpha)-4,5-epoxypregnane-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (4alpha,5alpha)-4,5-epoxypregnane-3,20-dione(17503-05-8)
• EPA Substance Registry System: (4alpha,5alpha)-4,5-epoxypregnane-3,20-dione(17503-05-8)

Safety Data

• Hazardous Substances Data: 17503-05-8(Hazardous Substances Data)

Usage

General Description

(4alpha,5alpha)-4,5-epoxypregnane-3,20-dione is a steroid compound that belongs to the class of pregnane derivatives. It is a precursor to the synthesis of various hormones in the body, including progesterone and corticosteroids. (4alpha,5alpha)-4,5-epoxypregnane-3,20-dione has been studied for its potential therapeutic applications in the treatment of inflammation, autoimmune diseases, and certain types of cancer. Its chemical structure contains a four-ring system, with a five-membered lactone ring and three ketone groups. The epoxide moiety adds reactivity to the molecule, which can be utilized for further chemical modifications and drug design. The compound's biological activity and potential medicinal uses make it an important target for further research and development in the field of steroid chemistry and drug discovery.

Upstream product

• 57-83-0 Progesterone 

Downstream Products

• 57-83-0 progesterone 

Relevant articles and documents

Peroxide oxidation of Δ4-3-ketosteroids

Treatment of Δ4-3-ketosteroids with tert-butyl hydroperoxide in the presence of lithium hydroxide leads to the formation of the corresponding 4β,5β epoxides stereospecifically and in good yield.The stereospecificity of this reaction is explicable in terms of the accepted mechanism for the hydrogen peroxide epoxidation of Δ4-3-ketosteroids.The use of aqueous sodium peroxide as oxidant leads to the production of the corresponding Δ4-3,6-diones.A mechanism for this reaction is proposed in which the key step is autooxidation of the corresponding deconjugated Δ5-3-ketone, produced from the starting material in situ by the action of the reagents.Lithium peroxide does not oxidize androst-4-ene-3,17-dione at C-6, but produces the 4,5-epoxides in low yield together with an A-nor-3,5-secoacid.

RUTHENIUM COMPLEX AND PRODUCTION METHOD THEREOF, CATALYST, AND PRODUCTION METHOD OF OXYGEN-CONTAINING COMPOUND

PROBLEM TO BE SOLVED: To provide a ruthenium complex that is particularly useful as a catalyst for oxidizing a substrate having a carbon-hydrogen bond. SOLUTION: The ruthenium complex represented by the general formula (i) or a cis conformer thereof is provided. In the general formula (i), R1 represents H, a phenyl group or a substituted phenyl group; R2 represents H, a phenyl group or an alkyl group; L1 represents halogen or water molecule; L2 represents triphenylphosphine, pyridine, imidazole or dimethylsulfoxide; X represents halogen; and n represents 1 or 2. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPO&INPIT

Synthesis and cytotoxic activity of some novel steroidal C-17 pyrazolinyl derivatives

Fourteen novel steroidal C-17 pyrazolinyl derivatives 9a-g and 10a-g were synthesized from commercially available progesterone and tested for their cytotoxic activity against brine shrimp (Artemia salina) and three human cancer cell lines (NCI-H460, HeLa, and HepG2). Some of these synthetic compounds exhibited significant cytotoxic activity, and treatment of HeLa cells with compound 10b resulted in the cell population arrest in the S phase. A structure-activity relationship was discussed.

Highly efficient epoxidation of unsaturated steroids using magnesium bis(monoperoxyphthalate) hexahydrate

Fast generation of epoxides from the corresponding homoallylic and allylic steroidal olefins was developed by using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) as oxidant suspended in acetonitrile (CH3CN) at reflux temperature. The protocol involves the use of a safe readily available oxidant along with an easy work-up, which renders the process very efficient. Selective 4,5- and 5,6-epoxidations of steroids are reported. Among them, highly stereoselective epoxidation of Δ5-B-nor-cholestanes was achieved. Moreover, the method is chemoselective for the 5,6-position and can be applied to the epoxidation of ring-A enones.