566-60-9

Basic information

• Product Name: 16,(5-BETA)-PREGNEN-3-BETA-OL-20-ONE
• Synonyms: 16,(5-BETA)-PREGNEN-3-BETA-OL-20-ONE;16-DEHYDRO-5-BETA-PREGNAN-3-BETA-OL-20-ONE;16-DEHYDROPREGNANOLONE;16-DEHYDROEPIPREGNANOLONE;16-Pregnenolone;3α-Hydroxy-5β-pregn-16-en-20-one
• CAS NO: 566-60-9
• Molecular Formula: C₂₁H₃₂O₂
• Molecular Weight: 316.48
• Mol File: 566-60-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 443.7°Cat760mmHg
• Flash Point: 189.1°C
• Appearance: /
• Density: 1.077g/cm³
• Vapor Pressure: 9.72E-10mmHg at 25°C
• Refractive Index: 1.54
• CAS DataBase Reference: 16,(5-BETA)-PREGNEN-3-BETA-OL-20-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 16,(5-BETA)-PREGNEN-3-BETA-OL-20-ONE(566-60-9)
• EPA Substance Registry System: 16,(5-BETA)-PREGNEN-3-BETA-OL-20-ONE(566-60-9)

Safety Data

• Hazardous Substances Data: 566-60-9(Hazardous Substances Data)

Usage

Type

Synthetic steroid hormone, derivative of progesterone

Uses

Precursor for the production of other hormones and steroids in the pharmaceutical industry, synthesis of various pharmaceutical products (anti-inflammatory drugs, hormone replacement therapies, contraceptives), regulation of menstrual cycle, maintenance of pregnancy, and support of reproductive and physiological functions in the body

Importance

Crucial for hormonal balance and related medical treatments, used in laboratory research and studies for understanding and developing new treatments for hormonal imbalances and related medical conditions.

InChI:InChI=1/C21H32O2/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/h6,14-16,18-19,23H,4-5,7-12H2,1-3H3/t14-,15-,16+,18+,19+,20+,21-/m1/s1

Upstream product

• 128-20-1 PREGNANOLONE 
• 108-24-7 acetic anhydride 
• 106759-13-1 episarsasapogenin acetate 
• 21853-89-4 3α-acetoxy-5β-pregn-16-en-20-one 

Downstream Products

• 80-92-2 pregnanediol 
• 80-89-7 pregnadiol 

Relevant articles and documents

In vitro and in vivo activity of 16,17-dehydro-epipregnanolones: 17,20-bond torsional energy analysis and D-ring conformation

Purpose. Certain neuroactive pregnane steroids (also known as 'epalons') are allosteric modulators of the GABA, receptor and have been shown to be potent anticonvulsants, anxiolytics, sedative/hypnotics, and anesthetic agents: The purpose of this study was to calculate the structural consequences of introduction of a double bond in the 16,17-position and to determine if this modification would selectively reduce sedative activity, but maintain the potent anticonvulsant activity of neuroactive steroids. Methods. We have studied the biochemical and behavioral effects of introducing a 16,17 double bond into the naturally occurring neuroactive steroids, 3α-hydroxy-5α-pregnan-20-one (3α,5α-P) and 3α-hydroxy-5β-pregnan-20-one (3α,5α-P) and three synthetic neuroactive steroid derivatives, 3α-hydroxy-3β-methyl-5α-pregnan-20-one (3α,3βMe,5α-P), 3α-hydroxy-5α-androstane (3α,5α-A), and alphaxalone (3α,5α-11-one-P). Results. The 16-ene analogs of most of these neuroactive steroids were found to be 7- and 16-fold less potent in inhibiting [35S]TBPS binding to GABA(A) receptors and in a similar fashion, had reduced anticonvulsant and sedative potency in proportional amounts. The exception was the androstane (3α,5α-A) without a 17-acetyl group, that had virtually identical IC50 and ED50 values for the saturated and unsaturated derivatives. Calculation of the torsional energy profile for each of the 17-acetyl side chain conformations showed that the conformational energy minima found in the α,β-unsaturated keto systems, produce an orientation of the 20-keto group that is rotated by 165 degrees when compared to the non-conjugated acetyl group (determined by X-ray crystallography and its minimum energy conformation). Conclusions. The modified orientation of the 20-keto group of neuroactive steroids containing a 16-ene, provides an explanation for their decreased biological activity overall, but did not lead to an enhanced protective index.