302-97-6

Basic information

• Product Name: 4-Androsten-3-one-5-ene-17-carboxylic acid
• Synonyms: (17-beta)-androst-4-ene-17-carboxylicaci;3-oxo-androst-4-ene-17-beta-carboxylicaci;l552.803;4-ANDROSTEN-3-ONE-17-BETA-CARBOXYLIC ACID;4-Androsten-3-one-5-ene-17-carboxylic acid;4-ANDROSTEN-17BETA-CARBOXYLIC ACID-3-ONE;3-OXO-4-ANDROSTENE-17BETA-CARBOXYLIC ACID;3-OXO-ANDROST-4-ENE-17BETA-CARBOXYLIC ACID
• CAS NO: 302-97-6
• Molecular Formula: C₂₀H₂₈O₃
• Molecular Weight: 316.44
• EINECS: 414-990-0
• Product Categories: Organic acids
• Mol File: 302-97-6.mol
• Article Data: 32

Chemical Properties

• Melting Point: 260 °C(Solv: acetone (67-64-1); hexane (110-54-3))
• Boiling Point: 483.9 °C at 760 mmHg
• Flash Point: 260.6 °C
• Appearance: /
• Density: 1.17 g/cm³
• Vapor Pressure: 1.08E-10mmHg at 25°C
• Refractive Index: 1.564
• PKA: 4.81±0.60(Predicted)
• CAS DataBase Reference: 4-Androsten-3-one-5-ene-17-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Androsten-3-one-5-ene-17-carboxylic acid(302-97-6)
• EPA Substance Registry System: 4-Androsten-3-one-5-ene-17-carboxylic acid(302-97-6)

Safety Data

• Hazardous Substances Data: 302-97-6(Hazardous Substances Data)

Usage

General Description

4-Androsten-3-one-5-ene-17-carboxylic acid, also known as androstenedione, is a steroid hormone that is produced in the adrenal glands and gonads. It is a precursor to both male and female sex hormones, including testosterone and estrogen. Androstenedione is also known as a prohormone, meaning it can be converted into active hormones within the body. It has been used as a supplement by athletes and bodybuilders to enhance muscle mass and performance, although its use for this purpose has been banned in many sports organizations due to its potential to increase levels of testosterone and other androgens in the body. Additionally, androstenedione has been studied for its potential role in hormone replacement therapy for individuals with low levels of sex hormones.

InChI:InChI=1/C20H28O3/c1-19-9-7-13(21)11-12(19)3-4-14-15-5-6-17(18(22)23)20(15,2)10-8-16(14)19/h11,14-17H,3-10H2,1-2H3,(H,22,23)

Upstream product

• 853-27-0 3,20-dioxo-4-pregnen-21-al 
• 64-85-7 21-Hydroxyprogesterone 
• 67-66-3 chloroform 
• 15173-68-9 etienic acid 
• 7726-95-6 bromine 
• 64-19-7 acetic acid 
• 601-57-0 Cholest-4-en-3-one 
• 54668-68-7 21-nor-5-pregnene-3β,20-diol 
• 145-13-1 Pregnenolone 
• 1778-02-5 Pregnenolone acetate 
• 5716-95-0 21-hydroxy-17βH-pregnene-(4)-dione-(3.20) 
• 6424-28-8 20β_F,21-diacetoxy-17-hydroxy-pregn-4-en-3-one 
• 67-56-1 methanol 
• 1236-09-5 pregn-5-ene-3,20-dione 

Downstream Products

• 57-83-0 Progesterone 
• 10002-85-4 methyl 3β-hydroxy-5α-androstane-17β-carboxylate 
• 92472-22-5 3-oxoandrost-4-ene-17β-carboxamide 
• 53892-00-5 21-Diazoprogesterone 
• 92472-20-3 N-octyl-3-oxo-4-androstene-17β-carboxamide 
• 139116-00-0 C₆₁H₁₀₄NO₁₀P 
• 139136-49-5 C₆₃H₁₀₈NO₁₁P 
• 139116-01-1 C₆₅H₁₁₂NO₁₂P 
• 139116-02-2 C₆₇H₁₁₆NO₁₃P 
• 74352-89-9 N,N-diisopropyl-3-oxo-4-androstene-17β-carboxamide 
• 15173-54-3 3β-hydroxy-5α-etianic acid 
• 119169-84-5 3-Bromo-N-(1,1-dimethylethyl)androsta-3,5-diene-17β-carboxamide 
• 146175-29-3 S-(2-pyridyl)-androst-4-ene-3-one-17β-thiocarboxylate 
• 98653-71-5 N-hydroxysuccinimide ester of 4-androsten-3-one-17β-carboxylic acid 

Relevant articles and documents

Syntheses of [21-11C] and (21-13C)progesterone

[21-11C]Progesterone was synthesised via the cross-coupling 17β-carboxylic acid chloride-4-androsten-3-one with lithium [11C]methyl(2-thienyl)cuprate (LiCN). The title compound was obtained in 30-35% decay corrected radiochemical yield, based on [11C]methyl iodide, within 35 minutes after end of radionuclide production. The specific radioactivity was 14 GBq/μmole. (21-13C)Progesterone was synthesised using the same procedure for determination of the position of the label.

Steroid compound as well as preparation method and application thereof (by machine translation)

The compounds have the structure shown in the general formula (I) or the general formula (II); and experiments prove that the compounds can treat three-negative breast cancer by promoting apoptosis. (by machine translation)

Design, synthesis, and biological evaluation of novel androst-17β-amide structurally related compounds as dual 5α-reductase inhibitors and androgen receptor antagonists

Prostate cancer (PCa) is the second leading cause of death in men. Apart from androgen receptor, 5α-reductase has also been recognized as a potential target. In this study, a series of androst-17β-amide compounds have been designed and synthesized targeting both AR and 5α-reductase. Their anti-proliferation activities were evaluated in AR + cell line 22RV1 and AR ? cell line PC-3. The results indicated that most of the synthesized compounds inhibited the testosterone-stimulated cell proliferation with good selectivity and safety. Among all the compounds, androst[3,2-c]pyrazole derivatives (9a–9d) displayed the best inhibition activity comparable with flutamide. Moreover, most of the synthesized compounds displayed good 5α-reductase inhibitory activities with IC50 lower than 1 μM. The docking result of 9d-AR indicated that AR was forced to expands its binding cavity and maintain an antagonistic conformation since the steric hindrance of 9d impeded H12 transposition. Overall, compound 9d can be identified as a potential dual 5α-reductase inhibitor and AR antagonist, which might be of therapeutic importance for PCa treatment.