1420-49-1

Basic information

• Product Name: Androsta-3,5-diene-7,17-dione
• Synonyms: 3,5-Androstadiene-7,17-dione;Androsta-3,5-diene-7,17-dione;Androst-3,5-diene-7,17-dione;NSC 134910;Androst-3,5-dien-7,17-dione;Arimistane;(8R,9S,10R,13S,14S)-10,13-dimethyl-2,8,9,11,12,14,15,16-octahydro-1H-cyclopenta[a]phenanthrene-7,17-dione
• CAS NO: 1420-49-1
• Molecular Formula: C₁₉H₂₄O₂
• Molecular Weight: 284.3927
• EINECS: 1806241-263-5
• Mol File: 1420-49-1.mol

Chemical Properties

• Melting Point: 167-168℃
• Boiling Point: 449.3 °C at 760 mmHg
• Flash Point: 167.5 °C
• Appearance: /
• Density: 1.14g/cm³
• Vapor Pressure: 2.88E-08mmHg at 25°C
• Refractive Index: 1.568
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Sparingly), Methanol (Slightly)
• CAS DataBase Reference: Androsta-3,5-diene-7,17-dione(CAS DataBase Reference)
• NIST Chemistry Reference: Androsta-3,5-diene-7,17-dione(1420-49-1)
• EPA Substance Registry System: Androsta-3,5-diene-7,17-dione(1420-49-1)

Safety Data

• Hazardous Substances Data: 1420-49-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Androsta-3,5-diene-7,17-dione is used as an intermediate in the synthesis of various steroidal drugs, including anabolic steroids and corticosteroids. Its unique structure allows for the development of potent and effective medications that can be used to treat a wide range of medical conditions, such as inflammation, muscle wasting, and hormonal imbalances.
Used in Aromatase Inhibition:
Androsta-3,5-diene-7,17-dione is used as an aromatase inhibitor, which helps in the reduction of estrogen production. This application is particularly useful in the treatment of conditions where estrogen levels need to be controlled, such as hormone-related cancers or gynecomastia.
Used in Synthesis of Anti-Cancer Agents:
Androsta-3,5-diene-7,17-dione serves as a potential reagent in the synthesis of anti-cancer agents, such as MGC-803. Its involvement in the development of these agents highlights its importance in the fight against cancer and its potential to contribute to the discovery of novel therapeutic approaches.

InChI:InChI=1/C19H24O2/c1-18-9-4-3-5-12(18)11-15(20)17-13-6-7-16(21)19(13,2)10-8-14(17)18/h3,5,11,13-14,17H,4,6-10H2,1-2H3/t13-,14-,17-,18-,19-/m0/s1

Synthetic route

7-keto-DHEA (1139932-08-3) → androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
With perchloric acid In methanol	86%

5-androstene-3β-ol-7,17-dione (566-19-8) → androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
With perchloric acid In methanol; water at 20℃; for 12h;	80%

3,4-dihydro-2H-pyran (110-87-2) + 5-androstene-3β-ol-7,17-dione (566-19-8) → 3β-(2-tetrahydropyranyloxy)-androst-5-ene-7,17-dione (102890-86-8) + androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
With pyridinium p-toluenesulfonate In dichloromethane at 20℃; for 3h;	A 68% B 0.150 g

3β-acetoxy-5α,6β-dibromocholestane (514-50-1) → androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
With chromium(VI) oxide; acetic acid at 28 - 45℃; ueber mehrere Reaktionsstufen;

3β-Chlor-7β-hydroxyandrost-5-en-17-on → androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
With silver nitrate; dimethyl sulfoxide

3β-acetoxy-androstene-(5)-dione-(7.17) → androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
With hydrogenchloride; methanol

3-O-acetyl-7-oxo-dehydroepiandrosterone (1449-61-2) + aqueous methanol.HCl → androsta-3,5-diene-7,17-dione (1420-49-1)

7-oxo-dehydroepiandrosterone-3β-stearate (207670-02-8) → androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
With perchloric acid In methanol at 65℃; for 0.7h;	100 % Chromat.

7-oxo-dehydroepiandrosterone-3β-sulfate → androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
With perchloric acid In methanol at 65℃; for 1h;	99.8 % Chromat.

(3S,8R,9S,10R,13S,14S)-3-Chloro-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one (897-01-8) → androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: (microbiological transformation) 2: AgNO3, DMSO View Scheme

3-acetoxyandrost-5-en-7,17-dione (1139930-03-2) → androsta-3,5-diene-7,17-dione (1420-49-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol; water 2: perchloric acid / methanol View Scheme

androsta-3,5-diene-7,17-dione (1420-49-1) → C19H17(2)H7O2

Conditions	Yield
Stage #1: androsta-3,5-diene-7,17-dione With deuteriated sodium hydroxide In d(4)-methanol; water-d2 for 24h; Reflux; Stage #2: With hydrogen chloride In water-d2	50%

p-toluene sulfinic acid (536-57-2) + androsta-3,5-diene-7,17-dione (1420-49-1) → (8R,9S,10R,13S,14S)-4-hydroxy-10,13-dimethyl-3-tosyl-1,8,9,10,11,12,13,14,15,16-decahydro-7H-cyclopenta[a]phenanthrene-7,17(2H)-dione

Conditions	Yield
With hydrogenchloride; C52H52ClFeN24O2 In water; acetonitrile at 20℃; for 12h; Schlenk technique; Irradiation;	45%

androsta-3,5-diene-7,17-dione (1420-49-1) → 3α,4α-epoxyandrost-5-ene-7,17-dione (204270-50-8) + 3α,4α-dihydroxy-5β,6β-epoxyandrostane-7,17-dione

Conditions	Yield
With potassium permanganate; copper(I) sulfate In dichloromethane; water; tert-butyl alcohol at 20℃; Oxidation;	A 30% B 20%

p-toluene sulfinic acid (536-57-2) + androsta-3,5-diene-7,17-dione (1420-49-1) → (8R,9S,10R,13S,14S)-4-hydroxy-10,13-dimethyl-3-tosyl-1,8,9,10,11,12,13,14,15,16-decahydro-7H-cyclopenta[a]phenanthrene-7,17(2H)-dione

Conditions	Yield
With 2-(2-(1,3-dioxo-6-(piperidin-1-yl)-1H-benzo[de]isoquinolin-2(3H)-yl)ethoxy)ethyl acetate In acetonitrile at 20℃; for 36h; Schlenk technique; Irradiation;	30%

androsta-3,5-diene-7,17-dione (1420-49-1) → androstadiene-(3.5)-dione-(7.17)-17-semicarbazone

androsta-3,5-diene-7,17-dione (1420-49-1) → 3α,4α-epoxyandrost-5-ene-7,17-dione (204270-50-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform	850 mg

androsta-3,5-diene-7,17-dione (1420-49-1) → 4-chloroandrosta-3,5-diene-7,17-dione

Conditions	Yield
Multi-step reaction with 4 steps 1: 850 mg / m-chloroperbenzoic acid / CHCl3 2: 590 mg / aq. HCl / CHCl3 / Ambient temperature 3: pyridine 4: 150 mg / collidine / 4 h / Heating View Scheme

androsta-3,5-diene-7,17-dione (1420-49-1) → 4β-chloro-3α-hydroxyandrost-5-ene-7,17-dione (204270-52-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 850 mg / m-chloroperbenzoic acid / CHCl3 2: 590 mg / aq. HCl / CHCl3 / Ambient temperature View Scheme

androsta-3,5-diene-7,17-dione (1420-49-1) → 4β-chloro-3α-methylsulfonyloxyandrost-5-ene-7,17-dione

Conditions	Yield
Multi-step reaction with 3 steps 1: 850 mg / m-chloroperbenzoic acid / CHCl3 2: 590 mg / aq. HCl / CHCl3 / Ambient temperature 3: pyridine View Scheme

androsta-3,5-diene-7,17-dione (1420-49-1) → Methyl 2,3,4-tri-O-acetyl-O-(7,17-dioxoandrost-5-ene-3β-yl)-β-D-glucopyranosiduronate

chloro-trimethyl-silane (75-77-4) + androsta-3,5-diene-7,17-dione (1420-49-1) + trimethylaluminum (75-24-1) → C23H36O2Si + C23H36O2Si

Conditions	Yield
With copper(I) bromide In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; optical yield given as %de; stereoselective reaction;

Upstream product

• 514-50-1 3β-acetoxy-5α,6β-dibromocholestane 
• 1449-61-2 3-O-acetyl-7-oxo-dehydroepiandrosterone 
• 110-87-2 3,4-dihydro-2H-pyran 
• 566-19-8 5-androstene-3β-ol-7,17-dione 
• 207670-02-8 7-oxo-dehydroepiandrosterone-3β-stearate 
• 897-01-8 (3S,8R,9S,10R,13S,14S)-3-Chloro-10,13-dimethyl-1,2,3,4,7,8,9,10,11,12,13,14,15,16-tetradecahydro-cyclopenta[a]phenanthren-17-one 
• 1139930-03-2 3-acetoxyandrost-5-en-7,17-dione 
• 1139932-08-3 7-keto-DHEA 

Relevant articles and documents

Ergosteroids VII: perchloric acid-induced transformations of 7-oxygenated steroids and their bio-analytical applications--a liquid chromatographic-mass spectrometric study.

Sulfate esters of 7-oxo-delta(5)-steroids can be selectively and quantitatively hydrolyzed to the corresponding free steroids in the presence of carboxylic acid esters by solvolysis with perchloric acid in ethyl acetate at room temperature. Sulfates as well as carboxylic acid esters, methyl ethers, and ketals can be quantitatively converted to the corresponding 3,5-diene-7-one derivatives by heating with perchloric acid in methanol at 65 degrees C. The dienes have a strong UV absorption with maximum centered around 284 nm. These reactions have been used for the characterization and structural elucidation of 7-oxygenated-delta(5)-steroids that are present in complex biomatrices and can also be used for the quantitative estimation of total 7-oxo-delta(5)-steroids (free as well as conjugated) in biological matrices.

Stereoselective synthesis of some methyl-substituted steroid hormones and their in vitro cytotoxic activity against human gastric cancer cell line MGC-803

A series of 3-, 7-, 15-, and 16-methyl-substituted steroid analogs were synthesized via a highly stereoselective 1,6-conjugate addition. Under the catalysis of CuBr, AlMe3 reacted with four steroid dienone precursors to afford either the corresponding α-epimer of C-3 and C-7 methyl-substituted steroids as the major products, and the ratio of α/β was up to 10/1. No β-epimer has been detected for methyl addition at C-16. However, under the same reaction conditions, enantioselective methyl addition at C-15 afforded the 15β-epimer as the major product. The preliminary SAR analysis showed that the methyl substituents at C-7α and C-15β positions lead to a dramatical increase in potency against human gastric cancer cell line MGC-803.

Synthesis and Elucidation of Structure of Deuterated Androsta-3,5-diene-7,17-dione

The title compound was synthesized as an internal standard for the quantitative determination of Arimistane in biological samples. [2H7] Arimistane was obtained from Arimistane-d0 by alkaline H/2H exchange of th

Ergosteroids IV: Synthesis and biological activity of steroid glucuronosides, ethers, and alkylcarbonates

The 7-oxo derivative of dehydroepiandrosterone is more active than the parent steroid and is devoid of adverse side effects in rats, monkeys and humans. In anticipation of possible therapeutic use we have sought more active, longer lasting forms of 7-oxo- and 7β-hydroxydehydroepiandrosterones. The 7-oxo- and 7-hydroxy steroids have been converted to glucuronides, ethers and carbonate esters. The syntheses of these compounds are described and their ability to induce the formation of liver thermogenic enzymes when fed to rats is reported. Some of the new derivatives were found to be somewhat more effective than the equimolar amounts of 7-oxo-DHEA with which they were compared in each experiment. Copyright