1162-56-7

Basic information

• Product Name: Pregna-4,6-diene-3,20-dione
• Synonyms: 4,6-PREGNADIEN-3,20-DIONE;6-DEHYDROPROGESTERONE;DELTA-6-PROGESTERONE;PREGNA-4,6-DIENE-3,20-DIONE;Dehydroprogesterone;CIS-DYDROGESTERONE;6-DEHYDROPROGESTERONE HPLC 98.5+%;6,7-Didehydroprogesterone
• CAS NO: 1162-56-7
• Molecular Formula: C21H28O2
• Molecular Weight: 312.45
• EINECS: 1533716-785-6
• Mol File: 1162-56-7.mol

Chemical Properties

• Melting Point: 147-148 °C(Solv: hexane (110-54-3))
• Boiling Point: 462.8 °C at 760 mmHg
• Flash Point: 172.2 °C
• Appearance: /
• Density: 1.1 g/cm³
• Vapor Pressure: 9.55E-09mmHg at 25°C
• Refractive Index: 1.556
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Pregna-4,6-diene-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: Pregna-4,6-diene-3,20-dione(1162-56-7)
• EPA Substance Registry System: Pregna-4,6-diene-3,20-dione(1162-56-7)

Safety Data

• Hazardous Substances Data: 1162-56-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Pregn-4-ene-3,20-dione is used as an intermediate in the synthesis of various steroidal drugs for the treatment of different medical conditions. Its structural similarity to other steroidal compounds allows for its conversion into a wide range of pharmaceutically active substances.
Used in Hormone Research:
As a structural analog of progesterone, Pregn-4-ene-3,20-dione is used in research to study the effects of hormones on the human body. It can be utilized to investigate the mechanisms of hormone action, develop new drugs, and understand the role of hormones in various physiological processes.
Used in Steroid Synthesis:
Pregn-4-ene-3,20-dione serves as a key building block in the synthesis of various steroidal compounds, including hormones, corticosteroids, and anabolic agents. Its versatile structure makes it a valuable starting material for the development of new steroidal drugs with improved pharmacological properties.
Used in Quality Control and Analysis:
Pregn-4-ene-3,20-dione is used as a reference compound in the quality control and analysis of steroidal products. It helps ensure the purity, potency, and consistency of steroidal drugs by providing a standard for comparison during testing and analysis.
Used in the Production of Progesterone:
Pregn-4-ene-3,20-dione is used in the industrial production of progesterone, a vital hormone involved in the female reproductive system. As an impurity found in progesterone (P755900), it is essential to monitor and control its levels to maintain the quality and efficacy of progesterone-based medications.

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/h4-5,12,16-19H,6-11H2,1-3H3/t16-,17+,18-,19-,20-,21+/m0/s1

Upstream product

• 16484-70-1 7-Dehydro-9β,10α-progesteron 
• 10072-88-5 Des-A-17α-Δ⁹-pregnen-5,20-dion 
• 2755-10-4 (9β,10α)-pregn-4-ene-3,20-dione 
• 57-83-0 Progesterone 
• 1162-54-5 pregna-1,4-diene-3,20-dione 
• 17955-33-8 5,20-Dioxo-1,5-seco-2,3,4-trisnor-pregnan-1-saeure 
• 7093-55-2 5-pregnene-3,20-dione-3,20-bisethyleneketal 
• 74496-89-2 7α-bromo-5-pregnene-3,20-dione-3,20-bisethyleneketal 
• 32164-74-2 9α,10β-dehydroprogesterone diethylene ketal 
• 81968-78-7 3β-hydroxy-5,7-pregnadien-20-one 
• 110-86-1 pyridine 
• 24516-38-9 6β-bromo-4-pregnene-3,20-dione 
• 108-75-8 2,4,6-trimethyl-pyridine 
• 57-83-0 progesterone 

Downstream Products

• 21063-87-6 11α-hydroxypregna-4,6-diene-3,20-dione 
• 57-83-0 Progesterone 
• 600-99-7 11β,17,21-trihydroxy-pregna-4,6-diene-3,20-dione 
• 40845-01-0 3-(pregn-4-ene-3,20-dione-7α-yl)thiopropanoic acid 
• 565-96-8 11α-hydroxy-5β-pregnane-3,20-dione 
• 565-94-6 11α-hydroxy-5β-pregnane-3,20-dione 
• 21940-45-4 6,7-dehydrocortisol 21-acetate 
• 187110-83-4 7α-[4'-(aminophenyl)thio]pregna-4-ene-3,20-dione 
• 23035-53-2 9β,10α-Pregna-4,6,8(14)-trien-3,20-dion 

Relevant articles and documents

Synthesis of novel 7α-thiol-bridged progesterone derivatives

Novel synthetic routes to the formation of progesterone derivatives are of interest due to their potential role in the treatment of breast cancer. This multi-step synthesis proceeds via the dehydrogenation of the endocyclic ketone moiety of the steroid, a

Manganese mediated oxidation of progesterone in alkaline medium: Mechanism study and quantitative determination

We report here a non-immunosensing approach for the electrocatalytic oxidation of progesterone (P4) in alkaline medium using a salen-type manganese Schiff base complex (Mn(III)-SB) as a suitable electrocatalyst. We explored the role of carbon surface at glassy carbon electrode (GCE) and gold surface at glassy carbon/gold nanoparticles modified electrode (GCE/AuNPs) on immobilization of the Mn(III)-SB complex using cyclic voltammetry (CV) and density functional theory (DFT) calculations. The GCE/Mn(III)-SB displayed a pair of small redox peaks attributed to Mn(II)???Mn(III) with a small peak-to-peak separation (ΔEp), while GCE/AuNP/Mn(III)-SB displayed redox peaks with larger densities, but with a wider ΔEp. A combined molecular mechanics (MM) and quantum mechanics (QM) study were carried out to investigate the variation of surface configuration and energy barrier, when the Mn(III)-SB immobilization was modeled on GCE and GCE/Au surface. Cyclic voltammetry and hydrodynamic amperometry were used for the quantitative determination of P4. A limit of detection (LOD) of 11.4?nM was obtained using amperometry. The sensor retained 91% of its original response after 3 months, which is improved compared to previously reported P4 immunosensors. For the first time, a detailed mechanism for oxidation of P4 in alkaline medium was suggested. The proposed sensor was utilized to determine progesterone in milk samples.

Synthesis of 21-diazoprogesterone-6,7-3H2

The preparation of 21-diazoprogesterone-6,7-3H2 is described. Progesterone was dehydrogenated with chloranil to give Δ6-dehydroprogesterone. Degradation of the pregnane side-chain with sodium hypobromite gave the corresponding carboxylic acid. Catalytic reduction with carrier-free tritium followed by treatment with oxalyl chloride and then diazomethane afforded 21-diazoprogesterone-6,7-3H2 with a specific activity of 42 Ci/mmol.

Method and compound for synthetizing reprogestin

To the synthesis method, dehydropregnenolone is taken as a starting material, carbonyl-protected dehydropregnenolone is prepared, and then a methyl configuration overturning compound is obtained through photo-catalytic reaction and further subjected to deprotection. Hydroxylation and double bond rearrangement reaction yield progestin. The method has the advantages of easily available raw materials, high yield and simple and mild reaction conditions, and is suitable for industrial production of progestin.

Method for synthesizing dydrogesterone

The invention relates to a method for synthesizing a steroid drug dydrogesterone (CAS: 152-62-5). The method comprises the following steps: starting from pregnenolone, carrying out allylic halogenation and elimination to obtain a Pregna-5, 7-dien-3-ol-20-one intermediate; carrying out illumination isomerization to obtain a key intermediate 9 beta, 10 alpha-Pregna-5, 7-dien-3-ol-20-one; then carrying out Oppenauer oxidation (Oppenauer oxidation) to obtain 7-Dehydro-9beta, 10 alpha-progesterone, and finally, carrying out olefin shift isomerization under the action of acid to obtain the final product 6-Dehydro-9beta, 10 alpha-progesterone (a crude drug of dydrogesterone). The method is economical in steps and comprises four conversion steps; the total yield is as high as 16.4%; the raw materials are cheap and easy to obtain, the whole process route is green and safe, the bulk drugs are high in quality, the purity can reach 99.5% or above, and the method is suitable for industrial production.

Production process capable of industrially synthesizing dydrogesterone

The invention discloses a production process capable of industrially synthesizing dydrogesterone. Easily available progesterone is used as a raw material, and dydrogesterone is prepared through the steps of carbonyl protection, bromination, debromination, photochemical ring-opening reaction, photochemical ring-closing reaction, deprotection and double bond isomerization. The production process hasthe advantages of easily available initial raw materials, and easiness in implementation of each step and higher yield; the production process is simple and convenient to operate, is green and environment-friendly, and can be easily amplified to industrial production.

Preparation method for 5,7-pregnadien-3,20-dion-diethylene glycol ketal

The invention provides a preparation method for 5,7-pregnadien-3,20-dion-diethylene glycol ketal. The method comprises the following steps: performing an etherification reaction on progesterone and anetherification agent under the action of a catalyst to generate an ether; performing a dehydrogenation reaction on the ether and a dehydrogenation reagent to generate 6-dehydroprogesterone; and performing ketalation on the 6-dehydroprogesterone and ethylene glycol under the action of a catalyst and a dehydrating agent to generate the 5,7-pregnadien-3,20-dion-diethylene glycol ketal. The 5,7-pregnadien-3,20-dion-diethylene glycol ketal with less impurities can be obtained through the etherification, dehydrogenation reaction and ketalation, and the method has the advantages of a short route, ahigh yield, low raw material costs, simple operation and environmental protection, and is suitable for industrial production.

PROCESS FOR PREPARATION OF DYDROGESTERONE

The present invention relates to process for the preparation of dydrogesterone.

A pregnane -16 - ene - 3, 20 - dione steroid derivatives preparation method (by machine translation)

The invention relates to a pregnane - 16 - ene - 3, 20 - dione steroid derivatives (II) of the preparation method, is characterized in that the 17 preparation ethynyl - 17 hydroxy steroid derivatives I prepares the side with the reagent A or containing reagent A organic solvent reaction, reaction temperature: 25 °C - solvent reflux temperature, said reagent A is 7 - 15 weight percent of the phosphorus pentoxide dissolved in methanesulfonic acid solution that is formed 17 preparation ethynyl - 17 prepares the side hydroxy steroid derivatives (I) obtained in the reaction with the reagent A, reaction temperature: 25 °C - solvent reflux temperature, said reagent A is 7 - 15% weight percent of phosphorus pentoxide is dissolved in methanesulfonic acid solution that is formed. (by machine translation)

Effective and mild method for converting 3β-hydroxysteroids to 3-keto steroids via DDQ/TEMPO

A mild and efficient oxidation of 3β-hydroxysteroids to the corresponding 3-keto steroids can be carried out at room temperature, using DDQ in the presence of catalytic TEMPO. Oxidation of saturated 3β-hydroxysteroids gave the corresponding ketones in excellent yield. The 5-unsaturated 3β-hydroxysteroids are oxidized selectively to 4-en-3-one or 4,6-diene-3-one derivatives according to the amount of DDQ in reaction. This is a good method for the synthesis of 4,6-diene-3-one from the corresponding 3β-hydroxy-5-ene steroids. Meanwhile, configurations of the oxidation compounds 2a, 2b, 3b, 2c, 2f and 2g were identified by X-ray diffraction. A possible mechanism is presented and discussed.