1162-54-5

Basic information

• Product Name: 1,4-PREGNADIEN-3,20-DIONE
• Synonyms: PREGNA-1,4-DIENE-3,20-DIONE;1-DEHYDROPROGESTERONE;1,4-PREGNADIEN-3,20-DIONE;DELTA1-PROGESTERONE
• CAS NO: 1162-54-5
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.45
• Mol File: 1162-54-5.mol
• Article Data: 22

Chemical Properties

• Melting Point: 151-152 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 449.2°Cat760mmHg
• Flash Point: 167.4°C
• Appearance: /
• Density: 1.1g/cm³
• Vapor Pressure: 2.91E-08mmHg at 25°C
• Refractive Index: 1.556
• CAS DataBase Reference: 1,4-PREGNADIEN-3,20-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-PREGNADIEN-3,20-DIONE(1162-54-5)
• EPA Substance Registry System: 1,4-PREGNADIEN-3,20-DIONE(1162-54-5)

Safety Data

• Hazardous Substances Data: 1162-54-5(Hazardous Substances Data)

Usage

Uses

1,2-Dehydroprogesterone is a progesterone impurity which displays anti-flu virus effects. Also used int he preparation of cytotoxic agents with steroidal derivatives.

Definition

ChEBI: A 3-oxo Delta4-steroid that is progesterone which has been oxidised to introduce a double bond between positions 1 and 2.

InChI:InChI=1/C21H28O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h8,10,12,16-19H,4-7,9,11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1

Upstream product

• 57-83-0 Progesterone 
• 901-57-5 (20R)-pregn-5-ene-3β,20-diol 
• 566-91-6 cholesta-1,4-dien-3-one 
• 81201-82-3 (20S)-3-oxopregna-1,4-diene-20-carboxaldehyde 
• 35525-27-0 22-hydroxy-23,24-bis-norchola-1,4-diene-3-one 
• 71658-22-5 22-hydroxy-23,24-bisnor-1,4-choladien-3-one 
• 57968-14-6 Δ¹-5β-pregnen-20-one 
• 753497-21-1 17β-Δ¹-5β-pregnen-3,20-dione 
• 145-13-1 Pregnenolone 
• 57-88-5 cholesterol 
• 5062-62-4 20β_F-acetoxy-pregn-4-en-3-one 
• 50619-70-0 1β,3β-dihydroxy-pregna-5,16-dien-20-one 
• 5888-07-3 20β_F-acetoxy-5α-pregnan-3-one 
• 6003-19-6 acetic acid-(3β-hydroxy-5α-pregnanyl-(20β_F)-ester) 

Downstream Products

• 1667-98-7 3-hydroxy-19-norpregna-1,3,5⁽¹⁰⁾-trien-20-one 
• 5508-55-4 (+)-21-hydroxy-3,20-dioxo-pregna-1,4-diene 
• 57-83-0 (+/-)-progesterone 
• 601-33-2 dydrogesterone 

Relevant articles and documents

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The syntheses of the corticoid side-chain. II. A new synthesis of 17α,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetate from 21-hydroxy-20-methylpregna-1,4-dien-3-one

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Studies on A-norsteroids. I. Synthesis of A-nor-delta-3(5)-1,2-dioxo steroids.

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Synthesis of steroidal [1,2,4]triazolo[1,5-a]pyrimidines and their antiproliferative activities

— A facile strategy for the synthesis of steroidal [1,2,4]triazolo[1,5-a]pyrimidines 5a-g and 6a-g has been accomplished via a one-pot reaction of steroidal ketones, aromatic aldehydes and 3-amino-1,2,4-triazole in the presence of potassium tert-butoxide in refluxing tert-butanol. All the synthesized heterosteroids were evaluated for in vitro antiproliferative activity against human cancer cells by sulforhodamine B (SRB) assays. The preliminary results showed that compounds 6a and 6e possessed potent antiproliferative activities.

Potential insecticidal activity of steroidal U-17 pyrazolinyl derivatives

Agrochemical research, over the last two decades, has resulted in the discovery of chemically novel insecticides, of which steroids-based compounds that mimic the action of hormones have been considered as safe insecticides. In this study, eight steroidal C-17 pyrazolinyl derivatives were resynthesized through molecular hybridization and their insecticidal activities against 4th instar larvae of Mythimna separate were evaluated. These results showed that some compounds exhibited significant insecticidal activities and the susceptibility assays were expressed as the median lethal dose (LD50), of which one of the compounds exerted the most potent insecticidal activity (LD50 = 296 μg g-1), comparable to that of the natural product insecticide, celangulatin V (LD50 = 260 μg g-1). This strategy led to a promising candidate for the development of new steroidal insecticidal agents.