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
• Article Data: 18

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

Description

Pregn-4-ene-3,20-dione, also known as Pregna-4,6-diene-3,20-dione, is a naturally occurring steroidal compound derived from the pregnane family. It is characterized by its unique molecular structure, featuring a four-carbon chain at the fourth position and double bonds at the fourth and sixth positions of the steroid nucleus. Pregna-4,6-diene-3,20-dione is known for its diverse biological activities and potential applications in various fields.

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 
• 187110-83-4 7α-[4'-(aminophenyl)thio]pregna-4-ene-3,20-dione 
• 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 
• 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

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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 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.

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.