571-41-5

Basic information

• Product Name: (9β,10α)-17β-Hydroxyandrost-4-en-3-one
• Synonyms: (9β,10α)-17β-Hydroxyandrost-4-en-3-one;(9β,10α)-Testosterone;Lumitestosterone;Retrosterone;Retrotestosterone;retro-Testosterone
• CAS NO: 571-41-5
• Molecular Formula: C19H28O2
• Molecular Weight: 288.42442
• Mol File: 571-41-5.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 432.9°Cat760mmHg
• Flash Point: 184.7°C
• Appearance: /
• Density: 1.12g/cm³
• Vapor Pressure: 2.6E-09mmHg at 25°C
• Refractive Index: 1.56
• CAS DataBase Reference: (9β,10α)-17β-Hydroxyandrost-4-en-3-one(CAS DataBase Reference)
• NIST Chemistry Reference: (9β,10α)-17β-Hydroxyandrost-4-en-3-one(571-41-5)
• EPA Substance Registry System: (9β,10α)-17β-Hydroxyandrost-4-en-3-one(571-41-5)

Safety Data

• Hazardous Substances Data: 571-41-5(Hazardous Substances Data)

Usage

General Description

(9β,10α)-17β-Hydroxyandrost-4-en-3-one is a chemical compound that belongs to the class of androgens and is a derivative of testosterone. It is often used in the medical field as a prohormone for the synthesis of androgens and estrogens, and as a medication to treat conditions related to hormone imbalances, such as delayed puberty or hypogonadism. This chemical has anabolic and androgenic effects and is also sometimes used as a performance-enhancing drug in athletics and bodybuilding. However, its use for this purpose is often illegal and banned in many sports organizations due to its potential for abuse and undesirable side effects. Overall, (9β,10α)-17β-Hydroxyandrost-4-en-3-one has both medicinal and non-medicinal uses, with potential benefits and risks depending on its intended use and dosage.

InChI:InChI=1/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16+,17-,18+,19-/m0/s1

Synthetic route

4-(diethylamino)butan-2-one (3299-38-5) + 17β-hydroxy-desA-9β,10β-androstan-5-one + potassium tert-butylate (865-47-4) → 9β,10α-testosterone (571-41-5)

Conditions	Yield
With nitrogen In benzene

9β,10α-testosterone (571-41-5) + cyclohexanylcarbonyl chloride (2719-27-9) → Retrotestosteron 17-hexahydrobenzoat

Conditions	Yield
With pyridine In benzene

9β,10α-testosterone (571-41-5) + formic acid ethyl ester (109-94-4) → 2-Hydroxymethylenretrotestosteron

Conditions	Yield
With sodium hydride In benzene

9β,10α-testosterone (571-41-5) + methyl iodide (74-88-4) → 4,4-Me2-retroandrost-5-en-17β-ol-3-on

Conditions	Yield
With potassium tert-butylate In tert-butyl alcohol

9β,10α-testosterone (571-41-5) + methyl iodide (74-88-4) → 2-Me-retrotestosteron

Conditions	Yield
(i) (CO2Et)2, NaH, benzene, (ii) /BRN= 969135/, K2CO3, acetone, (iii) NaOEt, EtOH; Multistep reaction;

9β,10α-testosterone (571-41-5) + 3,5-dinitrobenoyl chloride (99-33-2) → Retro-5-androstan-3.17β-diol bis (3.5-(NO2)2-benzoat)

Conditions	Yield
(i) Li, liq. NH3, Et2O, (ii) /BRN= 990249/, Py, benzene; Multistep reaction;

9β,10α-testosterone (571-41-5) → 8,17β-Dihydroxy-Δ-9β,10α-androsten-3-on (23015-92-1)

Conditions	Yield
(microbiological transformation);

9β,10α-testosterone (571-41-5) → 9,17β-Dihydroxy-Δ4-9β,10α-androsten-3-on (23015-96-5)

Conditions	Yield
(microbiological transformation);

9β,10α-testosterone (571-41-5) → 11α.17β-Dihydroxy-9β.10α-androsten-4-3-on

Conditions	Yield
(microbiological transformation);

9β,10α-testosterone (571-41-5) → 9-Hydroxy-Δ4-9β,10α-androsten-3,17-dion (23015-99-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: (microbiological transformation) 2: aq. CrO3, H2SO4 / acetone View Scheme

Upstream product

• 63-05-8 androst-4-ene-3,17-dione 
• 63-05-8 4-androstene-3,17-dione 

Downstream Products

• 58-22-0 testosterone 
• 846-46-8 β-androstan-3,17-dion 
• 846-46-8 α-androstan-3,17-dion 
• 63-05-8 androst-3-en-3,17-dion 
• 1156-92-9 (10S,13R)-10,13-Dimethyl-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-3,17-diol 

Relevant articles and documents

Biotransformation of androst-4-ene-3,17-dione by some fungi

The incubations of androst-4-ene-3,17-dione with Aspergillus candidus MRC 200634, Aspergillus tamarii MRC 72400, Aspergillus wentii MRC 200316 and Mucor hiemalis MRC 70325 for 5 days are reported. A. candidus MRC 200634 mainly hydroxylated androst-4-ene-3,17-dione at C-11α, C-15α and C-15β whilst A. wentii MRC 200316 hydroxylated it mainly at C-6β. A. tamarii MRC 72400 showed predominately a Baeyer–Villiger monooxygenase activity. M. hiemalis MRC 70325 hydroxylated the substrate at C-14α and reduced most of it at C-17.