14072-39-0

Basic information

• Product Name: 16-bromo-3,17-dihydroxypregn-5-en-20-one
• CAS NO: 14072-39-0
• Molecular Formula: C₂₁H₃₁BrO₃
• Molecular Weight: 411.373
• Mol File: 14072-39-0.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 519.1°C at 760 mmHg
• Flash Point: 267.7°C
• Density: 1.36g/cm³
• Vapor Pressure: 6.03E-13mmHg at 25°C
• Refractive Index: 1.59
• CAS DataBase Reference: 16-bromo-3,17-dihydroxypregn-5-en-20-one(CAS DataBase Reference)
• NIST Chemistry Reference: 16-bromo-3,17-dihydroxypregn-5-en-20-one(14072-39-0)
• EPA Substance Registry System: 16-bromo-3,17-dihydroxypregn-5-en-20-one(14072-39-0)

Safety Data

• Hazardous Substances Data: 14072-39-0(Hazardous Substances Data)

Usage

General Description

16-bromo-3,17-dihydroxypregn-5-en-20-one, also known as 16-bromo-3,17-dihydroxyprogesterone, is a synthetic chemical compound that is structurally similar to the hormone progesterone. It contains a bromine atom at the 16th position and hydroxyl groups at the 3rd and 17th positions of the steroid ring. 16-bromo-3,17-dihydroxypregn-5-en-20-one has been studied for its potential as a progestin, as well as its antiestrogenic and antiproliferative effects. It has also been investigated for its potential as a treatment for hormone-related cancers and other reproductive disorders. Additionally, 16-bromo-3,17-dihydroxypregn-5-en-20-one may have uses in research and as a tool for studying hormone receptors and signaling pathways.

Upstream product

• 979-02-2 16-dehydropregnenolone acetate 
• 10035-10-6 hydrogen bromide 
• 64-19-7 acetic acid 
• 974-23-2 3β-hydroxy-16α,17α-epoxypregn-5-en-20-one 

Downstream Products

• 387-79-1 17-Hydroxypregnenolone 
• 83984-86-5 17-acetoxy-3β-formyloxy-pregn-5-en-20-one 
• 20867-15-6 3β-formyloxy-17-hydroxy-pregn-5-en-20-one 
• 1249-67-8 17α,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetate 
• 1807-14-3 17α,21-dihydroxypregna-1,4-diene-3,20-dione 
• 4134-58-1 hydroxyprogesterone acetate 
• 68-96-2 17-hydroxyprogesterone 

Relevant articles and documents

5 Alpha-reductase inhibitory and antiandrogenic activities of novel steroids in hamster seminal vesicles.

The pharmacological activity of several 16-bromosubstituted trienediones 4 and 5, 16-methyl substituted dienediones 6 and 7 and the 16-methyl substituted trienedione 8 was determined on gonadectomized hamster seminal vesicles by measuring the in vitro conversion of testosterone (T) to dihydrotestosterone (DHT) as 5alpha-reductase inhibitors and also the ability of these steroids to bind to the androgen receptor. Steroids 6 and 7 when injected together with T decreased the weight of the seminal vesicles thus showing an antiandrogenic effect. Compounds 5 and 6 reduced substantially the conversion of T to DHT and therefore can be considered good inhibitors for the enzyme 5alpha-reductase; however both steroids failed to form a complex with the androgen receptor. On the other hand compound 7 which showed a very small inhibitory activity for the enzyme 5alpha-reductase, exhibited a very high affinity for the androgen receptor and thus can be considered an effective antiandrogen. This compound also reduced substantially the weight of the seminal vesicles. Steroids 4 and 8 did not reduce the weight of the seminal vesicles and exhibited a low affinity for the androgen receptor; 8 showed a weak 5alpha-reductase inhibitory activity, whereas 4 exhibited a weak androgenic effect.

Practical synthesis of 16α-bromo-17α-hydroxysteroids via a Raney Ni-catalyzed bromide exchange reaction

D-ring modified glucocorticoids are attractive synthetic targets owing to their broad application in medicinal chemistry. Herein, we reported a practical synthesis of 16α-bromo-17α-hydroxysteroids from easily available 16β-bromo isomers via a Raney Ni-catalyzed bromide exchange reaction. The catalytic Finkelstein-type reaction features high yield, mild reaction condition, short reaction time and simple operation. The method provided an efficient approach to prepare 17α-hydroxy-15-pregnen-20-ones.