6585-70-2

Basic information

• Product Name: 5beta,6beta-epoxy-3beta-hydroxypregnan-20-one
• Synonyms: 5beta,6beta-epoxy-3beta-hydroxypregnan-20-one;pregnenolone 5,6 beta-epoxide;5,6β-Epoxy-3β-hydroxy-5β-pregnan-20-one
• CAS NO: 6585-70-2
• Molecular Formula: C₂₁H₃₂O₃
• Molecular Weight: 332.47698
• EINECS: 229-515-0
• Mol File: 6585-70-2.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5beta,6beta-epoxy-3beta-hydroxypregnan-20-one(CAS DataBase Reference)
• NIST Chemistry Reference: 5beta,6beta-epoxy-3beta-hydroxypregnan-20-one(6585-70-2)
• EPA Substance Registry System: 5beta,6beta-epoxy-3beta-hydroxypregnan-20-one(6585-70-2)

Safety Data

• Hazardous Substances Data: 6585-70-2(Hazardous Substances Data)

Upstream product

• 145-13-1 Pregnenolone 
• 108-05-4 vinyl acetate 

Downstream Products

• 14148-09-5 5α,6α-epoxy-20-oxopregnan-3β-yl acetate 
• 1868-98-0 6β-fluoro-3β,5-dihydroxy-5α-pregnan-20-one 
• 604-20-6 6alpha-Hydroxyprogesterone 
• 2300-03-0 6α-Fluoro-4-pregnene-3,20-dione 
• 903-71-9 6α-methyl-pregn-4-ene-3,20-dione 
• 4660-45-1 6β-fluoro-5-hydroxy-5α-pregnane-3,20-dione 

Relevant articles and documents

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 biological evaluation of heterocyclic analogues of pregnenolone as novel anti-osteoporotic agents

The structural modifications of pregnenolone have been described via the introduction of heterocyclic moieties at C-17 position by limiting the acyl group. Novel heterocyclic analogues of pregnenolone have been synthesized by using Friedlander and Claisen-Schmidt reactions, and the synthesized compounds were evaluated for their osteogenic activity. Among the synthesized derivatives, four compounds showed significantly increased ALP activity. Among all four active compounds, the novel compound 3a has shown significant bone matrix mineralization and mRNA expressions of osteogenic marker genes, BMP2, RUNX-2 and OCN at 1 pM concentration.

Synthesis of pregnane derivatives, their cytotoxicity on LNCaP and PC-3 cells, and screening on 5α-reductase inhibitory activity

A series of epoxy-and/or 20-oxime pregnanes were synthesized from commercially available pregnenolone. Compounds 1, 3, 7, 8 and 11-13 were evaluated for cytotoxicity activity towards LNCaP (androgen-dependent) and PC-3 (androgenindependent) prostate cancer cells. Compound 13 showed the highest activity on both LNCaP (IC50 15.17 μM) and PC-3 (IC50 11.83 μM) cell lines. Compound 11 showed weak activity on LNCaP cells (IC50 71.85 μM) and 8 showed the weak activity on PC-3 cells (IC50 68.95 μM), respectively. The 5α-reductase II (5AR2) inhibitory effects of compounds 1-3, 5 and 7-13 were investigated in a convenient screening model, in which compounds 5, 8, 11 and 12 were observed to be potential inhibitors of 5α-reductase, in particular, the 4-azasteroid 11, that also inhibited cell proliferation of androgen-dependent cells and 8, that in addition inhibited PC-3 cells more potently than LNCaP cells.