974-23-2

Basic information

• Product Name: 16,17-Epoxypregnenolone
• Synonyms: 16,17-Epoxy-3-hydroxypregn-5-en-20-one;16a,17a-epoxypregnenolone;EPOXYPREGNENOLONE;16,17-ALPHA EPOXY PREGNENOLONE;16,17-EPOXYPREGNENOLONE;16ALPHA,17ALPHA-EPOXYPREGNENOLONE;1-((3S,8R,9S,10R,13S,14S,16R,17S)-3-HYDROXY-10,13-DIMETHYL-1,2,3,4,7,8,9,10,11,12,13,14,15,16-TETRADECAHYDRO-20-OXA-CYCLOPROPA[16,17]CYCLOPENTA[A]PHENANTHREN-17-YL)-ETHANONE;3BETA-HYDROXY-16ALPHA,17ALPHA-EPOXY-5-PREGNEN-20-ONE
• CAS NO: 974-23-2
• Molecular Formula: C₂₁H₃₀O₃
• Molecular Weight: 330.46
• EINECS: 213-548-2
• Mol File: 974-23-2.mol
• Article Data: 22

Chemical Properties

• Melting Point: 185-188 °C
• Boiling Point: 462.3 °C at 760 mmHg
• Flash Point: 159.4 °C
• Appearance: /
• Density: 1.19 g/cm³
• Vapor Pressure: 1.73E-10mmHg at 25°C
• Refractive Index: 1.577
• Storage Temp.: −20°C
• PKA: 14.99±0.70(Predicted)
• CAS DataBase Reference: 16,17-Epoxypregnenolone(CAS DataBase Reference)
• NIST Chemistry Reference: 16,17-Epoxypregnenolone(974-23-2)
• EPA Substance Registry System: 16,17-Epoxypregnenolone(974-23-2)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 974-23-2(Hazardous Substances Data)

Usage

General Description

16,17-Epoxypregnenolone is a steroid hormone derived from pregnenolone, and it is a precursor to the production of other important hormones in the body. It is involved in the early stages of steroid biosynthesis and has been found to have anti-inflammatory and neuroprotective effects. 16,17-Epoxypregnenolone has also been studied for its potential use in treating conditions such as neurological disorders, immune-related diseases, and cancer. It is a promising compound for further research and development due to its potential therapeutic applications and beneficial effects on various physiological processes.

InChI:InChI=1/C21H30O3/c1-12(22)21-18(24-21)11-17-15-5-4-13-10-14(23)6-8-19(13,2)16(15)7-9-20(17,21)3/h4,14-18,23H,5-11H2,1-3H3

Upstream product

• 979-02-2 16-dehydropregnenolone acetate 
• 93-59-4 Perbenzoic acid 
• 78792-99-1 6β-methoxy-3α,5α-cyclo-pregn-16-en-20-one 
• 67-56-1 methanol 
• 6996-36-7 3β-(toluene-4-sulfonyloxy)-pregna-5,16-dien-20-one 
• 1162-53-4 16-dehydropregnenolone 
• 911442-53-0 3β-hydroxypregn-5-ene-16,20-dione 

Downstream Products

• 97350-93-1 3β,17β-dihydroxy-17α-methyl-16β-(phenylthio)-D-homoandrost-5-en-17a-one 
• 97374-02-2 3β,17α-dihydroxy-17β-methyl-16β-(phenylthio)-D-homoandrost-5-en-17a-one 
• 97350-87-3 3β-<(dimethyl(1,1-dimethylethyl)silyl)oxy>16β-(dimethylphenylsilyl)-20,20-(ethylenedioxy)-17α-hydroxy-5-pregnene 
• 97374-00-0 3β,17α-dihydroxy-16β-(dimethylphenylsilyl)-20,20-(ethylenedioxy)-5-pregnene 
• 97350-92-0 3β,17aβ-dihydroxy-16β-(dimethylphenylsilyl)-17aα-methyl-D-homoandrost-5-en-17-one 
• 97373-99-4 20,20-(ethylenedioxy)-3β,17α-dihydroxy-16β-phenylseleno-5-pregnene 
• 97350-89-5 3β,17α-dihydroxy-16β-(dimethylphenylsilyl)pregn-5-en-20-one 
• 97350-94-2 3β,17α-dihydroxy-16β-(dimethylphenylsilyl)-17β-methyl-D-homoandrost-5-en-17a-one 
• 97374-01-1 3β,17α-dihydroxy-16β-(phenylseleno)pregn-5-en-10-one 
• 97350-91-9 3β,17aβ-dihydroxy-17aα-methyl-16β-(phenylseleno)-D-homoandrost-5-en-17-one 
• 97374-03-3 3β,17α-dihydroxy-17β-methyl-16β-(phenylseleno)-D-homoandrost-5-en-17a-one 
• 203987-25-1 Acetic acid (3S,8R,9S,10R,13S,14S,16S,17S)-3-acetoxy-17-acetyl-10,13-dimethyl-17-methylsulfanylmethoxy-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl ester 
• 23357-24-6 3β,16β-diacetoxy-17α-hydroxypregn-5-en-20-one 
• 348119-53-9 17α-hydroxy-17β-methyl-16β-phenyl-D-homoandrosta-1,4,6-triene-3,17a-dione 

Relevant articles and documents

Synthesis and activity of novel 16-dehydropregnenolone acetate derivatives as inhibitors of type 1 5α-reductase and on cancer cell line SK-LU-1

Testosterone (T) plays a crucial role in prostate growth. In androgen-dependent tissues T is reduced to dihydrotestosterone (DHT) because of the presence of the 5α-reductase enzyme. This androgen is more active than T, since it has a higher affinity for the androgen receptor (AR). When this mechanism is altered, androgen-dependent diseases, including prostate cancer, could result. The aim of this study was to synthesize several 16-dehydropregnenolone acetate derivatives containing a triazole ring at C-21 and a linear or alicyclic ester moiety at C-3 of the steroidal skeleton. These steroids were designed as potential inhibitors of the activity of both types (1 and 2) of 5α-reductase. The cytotoxic activity of these compounds was also evaluated on a panel of PC-3, MCF7, and SK-LU-1 human cancer cell lines. The results from this study showed that with the exception of steroids 20-oxo-21-(1H-1,2,4-triazole-1-yl)pregna-5,16-dien-3β-yl-propionate and 20-oxo-21-(1H-1,2,4-triazole-1-yl)pregna-5,16-dien-3β-yl-pentanoate, the compounds exhibit a lower inhibitory activity for both isoenzymes of 5α-reductase than finasteride. Furthermore the 3β-hydroxy-21-(1H-1,2,4-triazole-1-yl)pregna-5,16-dien-20-one and 20-oxo-21-(1H-1,2,4-triazole-1-yl)pregna-5,16-dien-3β-yl-acetate derivatives display 80% cytotoxic activity on the SK-LU-1 cell line. These results also indicated that the triazole derivatives, which have a hydroxyl or acetoxy group at C-3, could have an anticancer effect, whereas the derivatives with a alicyclic ester group at C-3 do not show biological activity.

Synthesis of new derivatives of 21-imidazolyl-16-dehydropregnenolone as inhibitors of 5α-reductase 2 and with cytotoxic activity in cancer cells

The aim of this study was to synthesize several 16-dehydropregnenolone derivatives containing an imidazole ring at C-21 and a different ester moiety at C-3 as inhibitors of 5α-reductase 1 and 2 isoenzymes. Their binding capacity to the androgen receptor (AR) was also studied. Additionally, we evaluated their pharmacological effect in a castrated hamster model and their cytotoxic activity on a panel of cancer cells (PC-3, MCF7, SK-LU-1). The results showed that only the derivatives with an alicyclic ester at C-3 showed 5α-R2 enzyme inhibition activity, the most potent of them being 21-(1H-imidazol-1-yl)-20-oxopregna-5,16-dien-3β-yl-cyclohexanecarboxylate with an IC50of 29?nM. This is important because prostatic benign hyperplasia is directly associated with the presence of 5α-R2. However, all the derivatives failed to inhibit 5α-R1 or bind to the AR. These alicyclic ester derivatives decreased the weight and size of androgen-dependent glands in the hamster, indicating they are very active in vivo and are not toxic. In addition, the 21-(1H-imidazol-1-yl)-20-oxopregna-5,16-dien-3β-yl-acetate derivative showed the highest cytotoxic activity on the three cancer cell lines studied. It is therefore important in the synthesis of steroidal compounds to consider the size of the ester moiety at C-3 of the steroid skeleton, which is key in obtaining biological activity, as observed in this experiment.

Synthesis and transformations of 20-isoxazolylsteroids with modified D ring: I. Synthesis of 16α,17α-epoxyderivatives

Synthesis of 16α,17α-epoxy-20-isoxazolylsteroids was carried out starting with dehydropregnenolone acetate. Transformation procedures for preparation therefrom of open-chain compounds were considered. Physico-chemical characteristics of compounds synthesized were investigated.

Synthesis and cytotoxic effect of pregnenolone derivatives with one or two α,β-unsaturated carbonyls and an ester moiety at C-21 or C-3

Four series of pregnenolone derivatives having one or two α,β-unsaturated carbonyls and an ester moiety at C-21 or C-3 were synthetized to compare their cytotoxicity effect. The final compounds were evaluated on three human cancer cell lines: PC-3 (prostate cancer), MCF-7 (breast cancer), SKLU-1 (lung cancer) and a noncancerous cell line HGF (human gingival fibroblast). Two steroids with a 4-fluorinated benzoic acid ester at C-21 were the most active against lung cancer cell line with IC50 of 13.1 ± 1.2 and 12.8 ± 0.5 μM and showed a low percentage of cytotoxicity for noncancerous cells (27.63 ± 2.3 and 18.39 ± 1.2% in the screening at 50 μM).