638163-36-7

Basic information

• Product Name: [1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one
• CAS NO: 638163-36-7
• Molecular Weight: 292.398
• Mol File: 638163-36-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: [1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: [1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one(638163-36-7)
• EPA Substance Registry System: [1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one(638163-36-7)

Safety Data

• Hazardous Substances Data: 638163-36-7(Hazardous Substances Data)

Usage

Description

[1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one is a deuterated derivative of the hormone testosterone, which is a synthetic androgen and anabolic steroid. It is labeled with deuterium, a stable isotope of hydrogen, at specific positions in its structure, making it a valuable tool for scientific research and as a tracer in studies of steroid metabolism.

Uses

Used in Scientific Research:
[1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one is used as a research compound for understanding the mechanisms of testosterone action and metabolism in the body. Its deuterated nature allows researchers to track the fate and metabolism of the compound in biological systems.
Used in Steroid Metabolism Studies:
[1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one is used as a tracer in studies of steroid metabolism, providing insights into the pharmacokinetics and pharmacodynamics of androgenic and anabolic steroid drugs.
Used in Pharmaceutical Development:
[1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one can be used as a starting material or a reference compound in the development of new pharmaceuticals targeting androgen receptors or related metabolic pathways.
Used in Analytical Chemistry:
[1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one can be employed as a reference standard in analytical chemistry for the development and validation of methods for the detection and quantification of testosterone and its metabolites in biological samples.
Used in Endocrinology:
In the field of endocrinology, [1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one can be used to study the effects of androgens on various physiological processes, such as growth, development, and reproductive functions.
Used in Sports Medicine:
[1α,16,16,17α-2H4]androst-4-en-17β-ol-3-one may also be used in sports medicine to investigate the effects of androgens and anabolic steroids on athletic performance and muscle growth, as well as to develop strategies for detecting and preventing the misuse of these substances in sports.

Upstream product

• 4273-45-4 [1α,2,2,4,6,6,16,16-2H8]androst-4-ene-3,17-dione 
• 79037-28-8 [1α,2α-2H2]androst-4-ene-3,17-dione 
• 638163-35-6 [1α,2,2,4,6,6,16,16,17α-2H9]androst-4-en-17β-ol-3-one 
• 897-06-3 Androsta-1,4-diene-3,17-dione 

Downstream Products

• 638163-38-9 [1α,16,16,17α-2H4]androst-4-en-6β,17β-diol-3-one 

Relevant articles and documents

Syntheses of stable isotope-labeled 6β-hydroxycortisol, 6β-hydroxycortisone, and 6β-hydroxytestosterone

A method is described for the preparation of two types of multi-labeled 6β-hydroxycortisol containing either five deuterium atoms at C-19 methyl and C-1 methylene or four 13C atoms at C-1, C-2, C-4, and C-19 in addition to the five deuterium atoms for use as analytical internal standards for gas chromatography-mass spectrometry (GC-MS). BMD derivatives of [1,1,19,19,19-2H5]cortisone and [1,2,4,19- 13C4,1,1,19,19,19-2H5]cortisone (cortisone-2H5-BMD and cortisone-13C 4,2H5-BMD) were first synthesized via indan synthon method starting from optical active 11-oxoindanylpropionic acid and labeled isopropenyl anion ([1,1,3,3,3-2H5]- or [1,3- 13C2,1,1,3,3,3-2H5]isopropenyl anion). The labeled isopropenyl anion was prepared from commercially available [1,1,1,3,3,3-2H6]- or [1,3-13C 2,1,1,1,3,3,3-2H6]acetone. Ultraviolet (UV) irradiated autoxidation at C-6 position of 3-ethyl-3,5-dienol ether derivatives of the labeled cortisone-BMDs gave 6β-hydroxy-[1,1,19,19,19- 2H5]cortisone-BMD and 6β-hydroxy-[1,2,4,19- 13C4,1,1,19,19,19-2H5]cortisone-BMD, respectively, as a mixture of 6β- and 6α-epimers in a ratio of 4:1. Separation of 6β- and 6α-epimers by thin-layer chromatography (TLC) and subsequent hydrolysis of the BMD group at C-17 gave pure labeled 6β-hydroxycortisone. After protecting the keto group at C-3 of the labeled 6β-hydroxycortisone-BMD as semicarbazone, reduction of 11-keto group with NaBH4 and subsequent removal of the C-3 and C-17 protecting groups gave 6β-hydroxy-[1,1,19,19,19-2H5]cortisol (6β-hydroxycortisol-2H5) and 6β -hydroxy-[1,2,4,19-13C4,1,1,19,19,19-2H 5]cortisol (6β-hydroxycortisol-13C4, 2H5), respectively, as a mixture of 6β- and 6α-epimers (6β:6α=4.4:1). The isotopic compositions of 6β-hydroxycortisol-2H5 and 6β -hydroxycortisol-13C4,2H5 were 90.9 and 92.1 at.%, respectively. Furthermore, 6β-hydroxy-[1α ,16,16,17α-2H4]testosterone was synthesized by the UV irradiated autoxidation at C-6 position of 3-ethyl-3,5-dienol ether derivative of deuterium-labeled testosterone ([1α,16,16,17α- 2H4]testosterone) obtained by using catalytic deuteration and hydrogen-deuterium exchange reactions.