14279-42-6

Basic information

• Product Name: 20-Oxo-5α,6α-epoxypregna-16-ene-3β-ol acetate
• Synonyms: 20-Oxo-5α,6α-epoxypregna-16-ene-3β-ol acetate;5,6α-Epoxy-3β-(acetyloxy)-5α-pregn-16-en-20-one
• CAS NO: 14279-42-6
• Molecular Formula: C₂₃H₃₂O₄
• Molecular Weight: 372.49778
• Mol File: 14279-42-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 20-Oxo-5α,6α-epoxypregna-16-ene-3β-ol acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 20-Oxo-5α,6α-epoxypregna-16-ene-3β-ol acetate(14279-42-6)
• EPA Substance Registry System: 20-Oxo-5α,6α-epoxypregna-16-ene-3β-ol acetate(14279-42-6)

Safety Data

• Hazardous Substances Data: 14279-42-6(Hazardous Substances Data)

Usage

Chemical compound

20-Oxo-5α,6α-epoxypregna-16-ene-3β-ol acetate

Group

Steroids

Derivative

Synthetic derivative of pregnenolone

Usage

Used for research purposes in medicine and biochemistry

Applications

Potential development of pharmaceutical drugs

Study

Physiological effects and interactions with other compounds

Acetate group

Provides stability and aids in storage and handling

Importance

Important in the study of steroids and potential therapeutic uses

Upstream product

• 979-02-2 16-dehydropregnenolone acetate 

Downstream Products

• 55530-52-4 6β,16α-Dimethyl-pregnan-3β,5α-diol-20-on-3-acetat 
• 1616932-83-2 3β-p-iodophenylcarbamoiloxypregn-4,16-diene-6,20-dione 
• 1616932-82-1 3β-p-bromophenylcarbamoiloxypregn-4,16-diene-6,20-dione 
• 1616932-81-0 3β-p-chlorophenylcarbamoiloxypregn-4,16-diene-6,20-dione 
• 1616932-80-9 3β-p-fluorophenylcarbamoiloxypregn-4,16-diene-6,20-dione 
• 1616932-79-6 3β-phenylcarbamoiloxypregn-4,16-diene-6,20-dione 
• 1616932-78-5 3β-p-iodobenzoyloxypregn-4,16-diene-6,20-dione 
• 886223-56-9 3β-p-bromobenzoyloxypregn-4,16-diene-6,20-dione 
• 886223-57-0 3β-p-chlorobenzoyloxypregn-4,16-diene-6,20-dione 
• 5244-58-6 17α-hydroxy-6,16α-dimethylpregna-4,6-diene-3,20-dione 
• 2497-80-5 6,16α-Dimethyl-6-dehydro-17α-hydroxy-progesteron-17-acetat 

Relevant articles and documents

Effect of new hybrids based on 5,16-pregnadiene scaffold linked to an anti-inflammatory drug on the growth of a human astrocytoma cell line (U373)

In spite of the fact that anaplastic astrocytoma is an uncommon disease, very often the pathology of this disease is associated with lethal effects due to the late diagnosis and unspecific treatments. This paper reports the synthesis and the biological effect on the growth of U373 cell line (human anaplastic astrocytoma) of new hybrid compounds based on 5,16-pregnadiene scaffold linked to an anti-inflammatory drug (6a-e). Moreover, we also determined the cell growth effect of five non-steroidal anti-inflammatory drugs (naproxen, ibuprofen, ketoprofen, indomethacin and sulindac) as well as the free steroidal alcohol 5. The results from this study indicated that sulindac as well as compound 5 decreased the number of U373 cells at different concentrations. However, when an anti-inflammatory drug was bound to the steroidal structure (5), the resulting compounds (6a-e) showed an enhanced biological effect with exception of hybrid 6c. Furthermore, derivative 6e (sulindac hybrid) did not allow cell growth during six days of experiment at a concentration of 10 μM. The overall data indicated that these molecules showed an anti-proliferative activity on anaplastic astrocytoma cell line.

Microbial transformation of 5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one by Trichoderma viride

Fermentation of 5α,6α-epoxy-3β-hydroxy-16-pregnen-20-one (4) with Trichoderma viride under aerobic condition yielded 3β,5α,6β-trihydroxy-16-pregnen-20-one (5) and 3β,5α,6β,15β-tetrahydroxy-16-pregnen-20-one (6). Each microbial metabolite was characterized by spectroscopic methods. Compounds 6 and 3β,5α,15β-trihydroxy-16-pregnen-6,20-dione (7) are reported for the first time.

New 5α-reductase inhibitors: In vitro and in vivo effects

The enzyme 5α-reductase is responsible for the conversion of testosterone (T) to its more potent androgen dihydrotestosterone (DHT). This steroid had been implicated in androgen-dependent diseases such as: benign prostatic hyperplasia, prostate cancer, ac

Synthesis and cytotoxic effect on cancer cell lines and macrophages of novel progesterone derivatives having an ester or a carbamate function at C-3 and C-17

In this study we report the cytotoxic effect on human cancer cells of two series of novel progesterone derivatives; the first containing an aromatic ester (8a-e) or a carbamate functions both linked to C-3 (9a-e) on the pregn-4,16-diene-6,20-dione skeleto

Studies on the reaction of 16-dehydropregnenolone acetate (16-DPA) with m-chloroperbenzoic acid

Reaction of 16-DPA (1) with m-chloroperbenzoic acid (MCPBA) on activated silica gives selectively the 5,6-epoxy derivative 2 of 1 with an excellent yield of 91.75% whereas no selectivity was observed in solution phase reaction and a diepoxy (5,6 and 16,17) derivative 3 (as an isomeric mixture) is obtained.

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.

Ring A aromatic steroids in the pregnane series

4-Methylpregna-1,3,5(10)-trien-20-one and 4-methylpregna-1,3,5(10),16- tetraen-20-one have been obtained by a dienol: benzene type of rearrangement of 5α,6α-epoxypregnanes possessing a further double bond equivalent on ring A. The crystal structure of 4-methyl-19-norpregna-1,3,5(10)-trien-20-one is reported.