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
• Article Data: 4

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

Arimistane is an aromatase inhibitor used in the reduction of estrogen production as well as a potential reagent in the synthesis of anti-cancer agent MGC-803.

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

• 1139932-08-3 7-keto-DHEA 
• 1139930-03-2 3-acetoxyandrost-5-en-7,17-dione 
• 566-19-8 5-androstene-3β-ol-7,17-dione 
• 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 
• 207670-02-8 7-oxo-dehydroepiandrosterone-3β-stearate 
• 110-87-2 3,4-dihydro-2H-pyran 
• 1449-61-2 3-O-acetyl-7-oxo-dehydroepiandrosterone 
• 514-50-1 3β-acetoxy-5α,6β-dibromocholestane 

Relevant articles and documents

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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.

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