1096-38-4

Usage

Uses

Used in Organic Chemistry:
16-Dehydroprogesterone is utilized as a direct organocatalytic stereoselective transfer hydrogenation agent for the conjugated olefins of steroids. This application is significant in the synthesis of various steroidal compounds with specific stereochemistry, which is essential for their biological activity and potential pharmaceutical applications.
Used in Pharmaceutical Industry:
As a form of progesterone, 16-Dehydroprogesterone is used in the development of hormonal medications, particularly for conditions related to the menstrual cycle, pregnancy, and menopause. Its role in the etiology of breast cancer also makes it a subject of interest for the development of targeted therapies and potential treatments for this type of cancer.
Used in Research and Development:
16-Dehydroprogesterone serves as an important compound in the study of steroidal hormones and their effects on the human body. It is used in research to better understand the mechanisms of action of progesterone and its role in various physiological processes, as well as to develop new drugs and therapies for hormone-related conditions and diseases.

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/h6,12,16,18-19H,4-5,7-11H2,1-3H3

Upstream product

• 64-17-5 ethanol 
• 434-03-7 levonorgestrel 
• 24586-65-0 mercury(II) acetamide 
• 438-07-3 16α-hydroxyprogesterone 
• 1162-53-4 16-dehydropregnenolone 
• 108-94-1 cyclohexanone 
• 555-31-7 aluminum isopropoxide 
• 108-88-3 toluene 
• 34081-68-0 Δ⁵-pregnene-3β,16β,20(R)-triol 
• 556-91-2 aluminum tri-tert-butoxide 
• 67-64-1 acetone 
• 6870-79-7 (25R)-spirost-4-ene-3-one 
• 21933-96-0 17-Nitrooxy-4-pregnen-3,20-dion 
• 83914-34-5 5α-Chloro-3β-hydroxypregn-16-en-20-one 

Downstream Products

• 23738-15-0 16α-nitromethyl-pregn-4-ene-3,20-dione 
• 57-83-0 Progesterone 
• 566-56-3 5α-pregnan-3β,20α-diol 
• 595-77-7 R-16α,17-dihydroxy-pregn-4-ene-3,20-dione 
• 26359-00-2 11α-hydroxy-17βH-pregn-4-ene-3,20-dione 
• 1097-51-4 16α,17α-epoxyprogesterone 
• 14413-05-9 ((8S,9S,10R,13S,14S,17S)-17-Acetyl-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl)-phosphonic acid diethyl ester 
• 68-96-2 17-hydroxyprogesterone 

Related news

Characteristics of 16-Dehydroprogesterone (cas 1096-38-4) reductase in cell extracts of the intestinal anaerobe, Eubacterium sp. strain 14408/15/2019

16-Dehydroprogesterone reductase (16-DHPR) activity was present in cell extracts of Eubacterium sp. strain 144 only when the organism was grown in the presence of steroids containing a Δ16–17 double bond and C-20-ketone. Cells grown with 16-dehydropregnenolone contained 16-DHPR activity but la...detailed

Biotransformation of 16-Dehydroprogesterone (cas 1096-38-4) by the intestinal anaerobic bacterium, Eubacterium sp. 144☆08/14/2019

Eubacterium sp. 144 biotransformed 16-dehydroprogesterone by initially hydrating approx 50% to 16α-hydroxyprogesterone. The detection of this reaction was dependent, in part, on the solubility state of 16-dehydroprogesterone and was less extensive when the concentration of methanol was insuffic...detailed

Synthesis and evaluation of the antiproliferative activity of benzylidenes of 16-Dehydroprogesterone (cas 1096-38-4) series08/12/2019

Novel benzylidenes (chalcones) of the 16-dehydroprogesterone series have been characterized and their antitumor activity against two breast cancer cell lines was evaluated. Benzylidenes exhibit significant antiproliferative effect on cells and inhibit cell growth in hormone-dependent MCF-7 and h...detailed

Relevant academic research and scientific papers

Synthesis of 16-dehydro-20-oxopregnanes from 17α,20-epoxy-23,24-dinorcholan-22-oic acids. Highly stereospecific oxirane → allyl alcohol isomerization of an epoxycarboxylic acid

A microbial degradation product of natural sterols was converted into traditional precursor of steroid syntheses by a simple sequence. The title isomerization, the key step, was investigated to demonstrate a concerted mechanism, in which a cyclic transition state, involving the oxirane oxygen, the β- and γ-carbon, the γ-proton to be removed and the catalyst coordinated by the carboxylate group, is postulated.

Synthesis of fluorinated 3beta-hydroxypregn-5-en-20-one derivatives.

Treatment of the unstable 3beta-hydroxy-20, 20-dimethoxypregn-5-ene 3-acetate with acetic anhydride at reflux temperature gave a mixture of 3beta-hydroxy-20-methoxypregna-5, 17(20)-diene and 3beta-hydroxy-20-methoxypregna-5, 20-diene 3-acetates. Fluorination of this mixture with perchloryl fluoride afforded after fractionated crystallization 3beta-hydroxy-17-fluoro-20-methoxypregna-5, 20-diene 3-acetate. Acid hydrolysis of the reaction mixture and subsequent chromatographic separation led to 3beta-hydroxy-17-fluoropregn-5-en-20-one 3-acetate and 3beta-hydroxy-21-fluoropregn-5-en-20-one 3-acetate. 3beta-Hydroxy-17-fluoro-20-methoxy-pregna-5, 20-diene 3-acetate did not react further with perchloryl fluoride even under forcing conditions. Fluorination of 3beta-hydroxy-20-(N-ethyl benzylamino)-pregna-5, 17(20)-diene gave 3beta-hydroxy-17, 21-difluoro-pregn-5-en-20-one, exclusively.

Synthesis and anti-cancer activity of chiral tetrahydropyrazolo[1,5-a]pyridine-fused steroids

Regio- and stereoselective synthesis of novel chiral 4,5,6,7-tetrahydropyrazolo[1,5-a]pyridine–fused steroids via [8π?+?2π] cycloaddition of diazafulvenium methides with steroidal scaffolds is reported. The biological evaluation of the new family of hexacyclic steroids as anti-cancer agents was also carried out. Hexacyclic steroids bearing a benzyl group at C-22, derived from 16-dehydropregnenolone and 16-dehydroprogesterone, show considerable cytotoxicity against EL4 (murine T-lymphoma) in contrast with the corresponding C-22-unsubstituted derivatives showing low cytotoxicity. Thus, results indicate that the presence of the benzyl group is important to ensure cytotoxicity.

Steroids 48. Synthesis of 16α-ethyl-21-hydroxy-19-norpregn-4-ene-3,20-dione from 17-substituted 3-methoxyestradiols

A new synthesis of 16α-ethyl-21-hydroxy-19-norpregn-4-ene-3,20-dione is described, starting from 17-cyano- and 17α-ethynyl-3-methoxyestra-1,3,5-(10)-trien-17-ols.Keywords: steroids; synthesis; 19-norpregnenes; A-aromatic pregnenes

Introduction of 20-Keto Side Chains in 17-Oxosteroids: Wittig-Horner-Emmons Reactions of (E)-17--3-methoxyandrosta-3,5-diene

The synthesis is described of a series of polyfunctional unsaturated Δ16,20-20-isocyanosteroids 5a-f by the Wittig-Horner-Emmons reaction of (E)-17 steroid 4 with several aldehydes and with acetone.Hydrolysis of the isocyanosteroids 5a-f with dilute sulfuric acid gave Δ16-20-ketosteroids 6a-f in high yield.Hydrolysis of 5a was also possible under neutral conditions, via the intermediate Δ16,20-20-isocyanatosteroid 7a, leading to A-ring protected 16-dehydroprogesterone 8a.The Wittig-Horner-Emmons reaction, together with the described hydrolyses, provides a new method for the introduction of steroid side chains.The method is particularly suited for side chains of different size, structure, and functionality.

Preparation method of 16-dehydroprogesterone

The invention provides a preparation method of 16-dehydroprogesterone, and belongs to the technical field of organic synthesis. The preparation method of the 16-dehydroprogesterone provided by the invention comprises the following steps: mixing 17 alpha-hydroxyprogesterone, methylbenzene, water, acetic acid and semicarbazide hydrochloride, and carrying out elimination reaction to obtain the 16-dehydroprogesterone. The method provided by the invention is low in cost, high in product yield and purity and suitable for industrial large-scale production. Specifically, 17alpha-hydroxyprogesterone is taken as a raw material, and the raw material is low in price; toluene and water are used as solvents, semicarbazide hydrochloride is used as an elimination reagent, acetic acid is used as a catalyst, a reaction system is divided into a toluene layer and a water layer, the elimination reaction is specifically carried out in the water layer, and a product generated by the reaction is extracted to the toluene layer, so that the product yield and purity are prevented from being influenced by impurities generated by excessive reaction of the product.

Sensitized Aliphatic Fluorination Directed by Terpenoidal Enones: A "visible Light" Approach

In our continued effort to address the challenges of selective sp3 C-H fluorination on complex molecules, we report a sensitized aliphatic fluorination directed by terpenoidal enones using catalytic benzil and visible light (white LEDs). This sensitized approach is mild, simple to set up, and an economical alternative to our previous protocol based on direct excitation using UV light in a specialized apparatus. Additionally, the amenability of this protocol to photochemical flow conditions and preliminary evidence for electron-transfer processes are highlighted.

On a pregnane - 16 - ene - 3, 20 - dione steroid derivatives preparation method

The invention relates to a preparation method for a pregna-16-ene-3, 20-dione steroid derivative (II). The method is characterized by: reacting 17alpha-ethynyl-17beta-hydroxysteroid derivative I with a reagent A or an organic solvent containing the reagent A to obtaining the derivative (II). The reaction temperature ranges from 25DEG C to a solvent reflux temperature, and the reagent A is a solution formed by dissolving 5%-15% of phosphorus pentoxide in methanesulfonic acid.

New process for synthesizing steroid 3-one-4-ene

The invention discloses a new process for synthesizing steroid 3-one-4-ene. The method comprises the steps: with steroid 3-hydroxy-5-ene as a starting material, in a nonprotic organic solvent, with air or oxygen as an oxidant and with a transition metal nitrate and a 2,2,6,6-tetramethylpiperidine-1-oxyl free radical or an analogue thereof as catalysts, oxidizing to obtain the steroid 3-one-4-ene. The method has the advantages of high yield, mild reaction conditions, easily controlled operation, low energy consumption, low cost, and safety; and the whole process is friendly to the environment, and is suitable for industrialization.

Novel rhenium(i) catalysts for the isomerization of propargylic alcohols into α,β-unsaturated carbonyl compounds: An unprecedented recyclable catalytic system in ionic liquids

Carbonyl rhenium(i) complexes are efficient catalysts for the regioselective isomerization of terminal propargylic alcohols into α,β-unsaturated aldehydes or ketones which can be used as an unprecedented recyclable catalytic system (up to 10 consecutive runs) in the ionic liquid [BMIM][PF6].