2944-87-8

Basic information

• Product Name: 6alpha-Hydroxytestosterone
• Synonyms: 4-ANDROSTEN-6-ALPHA, 17-BETA-DIOL-3-ONE;4-ANDROSTENE-6ALPHA,17BETA-DIOL-3-ONE;6-ALPHA-HYDROXYTESTOSTERONE;6ALPHA,17BETA-DIHYDROXY-4-ANDROSTEN-3-ONE;6A-hydroxytestosterone--dea*schedule iii item;6A-HYDROXYTESTOSTERONE--DEA SCHEDULE III;6,17-Dihydroxy-617b-androst-4-en-3-on;6-Hydroxy Testosterone
• CAS NO: 2944-87-8
• Molecular Formula: C₁₉H₂₈O₃
• Molecular Weight: 304.42
• Product Categories: Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Steroids;Steroid and Hormone
• Mol File: 2944-87-8.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 479.8 °C at 760 mmHg
• Flash Point: 258.1 °C
• Appearance: /
• Density: 1.19g/cm³
• Vapor Pressure: 3.19E-11mmHg at 25°C
• Refractive Index: 1.578
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 6alpha-Hydroxytestosterone(CAS DataBase Reference)
• NIST Chemistry Reference: 6alpha-Hydroxytestosterone(2944-87-8)
• EPA Substance Registry System: 6alpha-Hydroxytestosterone(2944-87-8)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-40-63
• Safety Statements: 22-36
• WGK Germany: 3
• Hazardous Substances Data: 2944-87-8(Hazardous Substances Data)

Usage

Description

6alpha-Hydroxytestosterone, also known as a metabolite of testosterone, is an off-white solid with unique chemical properties. It is derived from the metabolism of testosterone and is classified as a controlled substance due to its potential applications and regulatory status.

Uses

Used in Pharmaceutical Industry:
6alpha-Hydroxytestosterone is used as an intermediate in the synthesis of various pharmaceutical compounds for [application reason]. Its role as a metabolite of testosterone makes it a valuable component in the development of drugs targeting hormonal imbalances or conditions related to androgen levels.
Used in Research and Development:
6alpha-Hydroxytestosterone is used as a research compound for [application reason], such as studying the effects of testosterone metabolism, understanding the role of androgens in various physiological processes, and developing new therapies for conditions influenced by hormonal balance.
Used in Sports Medicine:
6alpha-Hydroxytestosterone is used as a diagnostic marker for [application reason], helping to identify the use of performance-enhancing drugs in sports. Its status as a controlled substance makes it a critical component in anti-doping efforts and ensuring fair competition.
Used in Hormone Replacement Therapy:
6alpha-Hydroxytestosterone is used as a potential therapeutic agent for [application reason], such as treating conditions related to androgen deficiency or imbalance. Its role in testosterone metabolism makes it a candidate for hormone replacement therapies, although further research is needed to determine its efficacy and safety in this context.

InChI:InChI=1/C19H28O3/c1-18-7-5-11(20)9-15(18)16(21)10-12-13-3-4-17(22)19(13,2)8-6-14(12)18/h9,12-14,16-17,21-22H,3-8,10H2,1-2H3/t12-,13-,14-,16-,17-,18+,19-/m0/s1

Upstream product

• 63-05-8 Androstenedione 
• 58-22-0 testosterone 
• 315-37-7 testosterone heptanoate 
• 521-17-5 5-androstenediol 
• 53-43-0 dehydroepiandrosterone 
• 481-29-8 Epiandrosterone 

Downstream Products

• 899-39-8 17β-hydroxy-5α-androstane-3,6-dione 
• 2243-06-3 androst-4-ene-3,6,17-trione 

Relevant articles and documents

Preparative-Scale Production of Testosterone Metabolites by Human Liver Cytochrome P450 Enzyme 3A4

Just like the drugs themselves, their metabolites have to be evaluated to succeed in a drug development and approval process. It is therefore essential to be able to predict drug metabolism and to synthesise sufficient metabolite quantities for further pharmacological testing. This study evaluates the possibility of using in vitro biotransformations to solve both these challenges in the case of testosterone as a representative component for steroids. The application of cells of Pichia pastoris with expressed membrane-associated human liver cytochrome P450 enzyme (P450) 3A4 in two cycles of a preparative-scale bioreactor experiment enabled the isolation of the common metabolites 6β-hydroxytestosterone and 6β-hydroxyandrostenedione on a 100 mg scale. Side-product formation caused by enzymes intrinsic to P. pastoris was reduced. In addition more polar testosterone metabolites formed by a P450 3A4-catalysed bioconversion, than the known mono-hydroxylated ones, are reported and 6-dehydro-15β-hydroxytestosterone as well as the di-hydroxylated steroids 6β,16β-dihydroxytestosterone, 6β,17β-dihydroxy-4-androstene-3,16-dione and 6β,12β-dihydroxyandrostenedione were isolated and verified by NMR analysis. Their respective biological significance remains to be investigated. Whole-cell P450 catalysts expressed in P. pastoris qualify as a tool for the preparative-scale synthesis of human metabolites. Biotransformation processes in combination with standard chemical procedures allow the isolation and characterisation even of minor drug metabolite products. (Figure presented.).

Biotransformation of testosterone by Cladosporium sphaerospermum

Incubation of testosterone 1 with Cladosporium sphaerospermum MRC 70266 afforded six metabolites and two of these metabolites, 6β,16β,17β-trihydroxyandrost-4-en-3-one 6 and 6β,12β,17β-trihydroxyandrost-4-en-3-one 7, were determined as new compounds. The fungus mainly hydroxylated testosterone 1 at C-6β, accompanied by some minor hydroxylations at C-7β, C-12β, C-15α and C-16β. A minor oxidation at C-17 and a minor 5α-reduction were also observed.

Microbial transformation of epiandrosterone by Aspergillus sydowii

Incubation of epiandrosterone with Aspergillus sydowii MRC 200653 afforded ten metabolites. The fungal dehydrogenation of epiandrosterone is reported for the first time. The formation of the major metabolite, 6?-hydroxyandrost-4-ene-3,17-dione, involved first dehydrogenation to give a 4-ene and then hydroxylation at C-6?. Small amounts of the substrate were hydroxylated at C-1α, C-7α, C-7β and C-11α.