1096-38-4

Basic information

• Product Name: 16-Dehydroprogesterone
• Synonyms: pregna-4,16-diene-3,20-dione;16-DEHYDROPROGESTERONE CRYSTALLINE;17-acetyl-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15-decahydrocyclopenta[a]phenanthren-3-one;17-Acetylandrosta-4,16-diene-3-one;NSC-11037;ZK-47520;16,17-Didehydroprogesterone;C03207
• CAS NO: 1096-38-4
• Molecular Formula: C₂₁H₂₈O₂
• Molecular Weight: 312.45
• EINECS: 214-142-8
• Product Categories: Pharmaceutical Raw Materials;Steroids
• Mol File: 1096-38-4.mol
• Article Data: 25

Chemical Properties

• Melting Point: 185-187 °C(lit.)
• Boiling Point: 460.983 °C at 760 mmHg
• Flash Point: 171.519 °C
• Appearance: /
• Density: 1.11 g/cm³
• Vapor Pressure: 1.11E-08mmHg at 25°C
• Refractive Index: 1.557
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), DMSO (Slightly, Sonicated), Methanol (Slightly)
• CAS DataBase Reference: 16-Dehydroprogesterone(CAS DataBase Reference)
• NIST Chemistry Reference: 16-Dehydroprogesterone(1096-38-4)
• EPA Substance Registry System: 16-Dehydroprogesterone(1096-38-4)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-40
• Safety Statements: 22-36
• WGK Germany: 3
• Hazardous Substances Data: 1096-38-4(Hazardous Substances Data)

Usage

Uses

16-Dehydroprogesterone is used in the direct organocatalytic stereoselective transfer hydrogenation of conjugated olefins of steroids. 16-Dehydroprogesterone is a form of Progesterone (P755900), a steroid hormone produced by the corpus luteum that induces maturation and secretory activity of the uterine endothelium; suppresses ovulation. Progesterone is implicated in the etiology of breast cancer.

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 
• 13609-89-7 3-Acetato 20-dimetilacetale di Δ⁵-pregnen-3β-ol-20-one 
• 57-83-0 Progesterone 
• 83914-32-3 5α-Chloro-3β-hydroxypregn-17(20)-ene-20-carboxaldehyde 
• 139563-86-3 (E)-17-<(Diethylphosphono)formamidomethylene>-3-methoxyandrosta-3,5-diene 
• 57144-06-6 3-methoxyandrosta-3,5-dien-17-one 
• 71136-48-6 N-[(R)-2-Methyl-4-((4aR,4bS,6aS,6bS,9aS,10aS,10bS)-4a,6a,7-trimethyl-2-oxo-3,4,4a,4b,5,6,6a,6b,9a,10,10a,10b,11,12-tetradecahydro-2H-9-oxa-pentaleno[2,1-a]phenanthren-8-yl)-butyl]-acetamide 
• 17094-86-9 (25R)-22αN-spirosol-4-en-3-one 
• 20952-02-7 28-acetyl-22R,25R-spirosolan-4-en-3-one 
• 138742-89-9 (E)-17--3-methoxyandrosta-3,5-diene 
• 145842-81-5 (E)-17-(isocyanotosylmethylene)androst-4-en-3-one 
• 138742-95-7 (E)-17--3-methoxyandrosta-3,5-diene 

Downstream Products

• 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 articles and documents

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 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.

Chemistry of N,P-acetals: Application to the synthesis of 20-ketosteroids

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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.

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.

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.