4075-07-4

Usage

Uses

Used in Pheromone Applications:
4,16-Androstadien-3-one is used as a pheromone in the fragrance industry for its ability to elicit a strong response in humans. It is believed to influence social and sexual behaviors, making it a valuable component in perfumes and colognes.
Used in Research and Development:
In the scientific community, 4,16-Androstadien-3-one is used as a research compound to study its effects on human behavior and pheromone communication. This helps in understanding the role of pheromones in various aspects of human interaction and attraction.
Used in Cosmetics and Personal Care:
4,16-Androstadien-3-one is also used in the development of cosmetics and personal care products, where it may be added to enhance the product's appeal and effectiveness in attracting attention or creating a desired effect on the user's mood or behavior.

InChI:InChI=1/C19H26O/c1-18-9-3-4-16(18)15-6-5-13-12-14(20)7-11-19(13,2)17(15)8-10-18/h3,9,12,15-17H,4-8,10-11H2,1-2H3

Synthetic route

17β-methoxycarbonyloxy-androst-4-en-3-one (19865-18-0) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
In toluene at 460℃;	90%
In acetone; toluene	90%

cesium acetate (3396-11-0) + Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (182243-71-6) → 4,16-androstadien-3-one (4075-07-4) + 3-oxoandrost-4-en-17α-yl acetate (1425-09-8)

Conditions	Yield
With 18-crown-6 ether In benzene for 72h; Heating;	A 10% B 76%

Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (182243-71-6) → 4,16-androstadien-3-one (4075-07-4) + 3-oxoandrost-4-en-17α-yl acetate (1425-09-8)

Conditions	Yield
With 18-crown-6 ether; cesium acetate In benzene for 72h; Heating;	A 10% B 76%

17β-tosyloxyandrostan-4-en-3-one (1255-57-8) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
Stage #1: 17β-tosyloxyandrostan-4-en-3-one With tetrabutylammonium acetate In 1-methyl-pyrrolidin-2-one at 160℃; for 4h; Stage #2: With potassium hydroxide In ethanol at 20℃; for 48h;	61%
With aluminum oxide In benzene for 20h; Heating;

indole (120-72-9) + 17-iodoandrosta-4,16-dien-3-one (100772-35-8) → 17-(1H-indol-1-yl)androsta-4,16-dien-3-one + 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
With copper(l) iodide; 2,2,6,6-tetramethylheptane-3,5-dione; potassium carbonate In dimethyl sulfoxide at 100℃; for 24h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	A 55% B 15 %Spectr.
With copper(l) iodide; potassium carbonate; butane-2,3-dione dioxime In dimethyl sulfoxide at 100℃; for 24h; Reagent/catalyst; Inert atmosphere;	A 8 %Spectr. B 72 %Spectr.

bis(androst-4-en-3-on)-17β-yl oxalate → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
at 600℃; under 0.00750075 Torr; for 1h; Flash vacuum pyrolysis;	29%

3-oxoandrost-4-en-17α-yl benzoate (36025-82-8) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
at 300℃; Erhitzen unter Stickstoff;
at 300℃;

HAD (1224-94-8) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
With cyclohexanone; aluminum isopropoxide; toluene

testosterone (58-22-0) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 76 percent / pyridine; various solvent(s) / 24 h / 0 °C 2: 90 percent / toluene / 460 °C View Scheme
(i) MeSO2Cl, Py, (ii) LiCl, DMF; Multistep reaction;

testosterone triflate (159949-15-2) → 17α-Azido-androst-4-en-3-on + 17-methyl-18-norandrosta-4,13(17)-dien-3-one (38978-06-2) + 4,16-androstadien-3-one (4075-07-4) + 17β-Methyl-18-norandrosta-4,13-dien-3-on

Conditions	Yield
With lithium azide In N,N-dimethyl-formamide at 25℃; for 0.5h; Substitution;

testosterone triflate (159949-15-2) → 17-methyl-18-norandrosta-4,13(17)-dien-3-one (38978-06-2) + 4,16-androstadien-3-one (4075-07-4) + 17β-Methyl-18-norandrosta-4,13-dien-3-on

Conditions	Yield
With sodium azide In N,N-dimethyl-formamide at 90℃; for 0.0833333h; Substitution;

Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester (182243-71-6) → 17α-Azido-androst-4-en-3-on + 17-methyl-18-norandrosta-4,13(17)-dien-3-one (38978-06-2) + 4,16-androstadien-3-one (4075-07-4) + 17β-Methyl-18-norandrosta-4,13-dien-3-on

Conditions	Yield
With lithium azide In N,N-dimethyl-formamide at 90℃; for 9h; Substitution;

testosterone (58-22-0) + androstene-(5)-diol-(3.17) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine / 0 °C 2: LiN3 / dimethylformamide / 9 h / 90 °C View Scheme

testosterone (58-22-0) + <2,4,6-triiodo-phenoxy>-acetyl chloride → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / pyridine / 0.25 h / 0 - 20 °C 2: 10 percent / 18-crown-6 / benzene / 72 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 100 percent / pyridine / 0.25 h / 0 - 20 °C 2: 10 percent / CsOAc, 18-crow-6 / benzene / 72 h / Heating View Scheme

Estra-5(10),16-dien-3-one (161061-98-9) + ethanol (64-17-5) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
In ethyl acetate

Al(OPri)3 + 5α-5,16-Androstadien-3α-ol (30505-67-0) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
In water; cyclohexanone; toluene

C20H27IO → 17-(1H-indol-1-yl)androsta-4,16-dien-3-one + 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol; water / 2.5 h / Reflux 2: potassium carbonate; 2,2,6,6-tetramethylheptane-3,5-dione; copper(l) iodide / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

C20H27IO → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / ethanol; water / 2.5 h / Reflux 2: potassium carbonate; indole; copper(l) iodide; N,N`-dimethylethylenediamine / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

3-methoxyandrosta-3,5-dien-17-one hydrazone (1131428-48-2) → 17-(1H-indol-1-yl)androsta-4,16-dien-3-one + 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; iodine / 1,4-dioxane / 0.5 h 2: hydrogenchloride / ethanol; water / 2.5 h / Reflux 3: potassium carbonate; 2,2,6,6-tetramethylheptane-3,5-dione; copper(l) iodide / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

3-methoxyandrosta-3,5-dien-17-one hydrazone (1131428-48-2) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine; iodine / 1,4-dioxane / 0.5 h 2: hydrogenchloride / ethanol; water / 2.5 h / Reflux 3: potassium carbonate; indole; copper(l) iodide; N,N`-dimethylethylenediamine / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

3-methoxyandrosta-3,5-dien-17-one (57144-06-6) → 17-(1H-indol-1-yl)androsta-4,16-dien-3-one + 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate; triethylamine / ethanol / 2 h / Reflux 2: triethylamine; iodine / 1,4-dioxane / 0.5 h 3: hydrogenchloride / ethanol; water / 2.5 h / Reflux 4: potassium carbonate; 2,2,6,6-tetramethylheptane-3,5-dione; copper(l) iodide / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

3-methoxyandrosta-3,5-dien-17-one (57144-06-6) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrazine hydrate; triethylamine / ethanol / 2 h / Reflux 2: triethylamine; iodine / 1,4-dioxane / 0.5 h 3: hydrogenchloride / ethanol; water / 2.5 h / Reflux 4: potassium carbonate; indole; copper(l) iodide; N,N`-dimethylethylenediamine / dimethyl sulfoxide / 24 h / 100 °C / Inert atmosphere View Scheme

17-iodoandrosta-4,16-dien-3-one (100772-35-8) → 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
With indole; copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In dimethyl sulfoxide at 100℃; for 24h; Reagent/catalyst; Inert atmosphere;	60 %Spectr.

17-iodoandrosta-4,16-dien-3-one (100772-35-8) + hex-1-yne (693-02-7) → 17-(hex-1-yn-1-yl)androsta-4,16-dien-3-one + 4,16-androstadien-3-one (4075-07-4)

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; potassium carbonate; triphenylphosphine In dimethyl sulfoxide at 100℃; Reagent/catalyst; Sonogashira Cross-Coupling; Inert atmosphere;	A 22 %Spectr. B 11 %Spectr.

4,16-androstadien-3-one (4075-07-4) → 4α,5α-epoxyandrost-16-en-3-one (63015-31-6) + 4β,5β-epoxyandrost-16-en-3-one

Conditions	Yield
With sodium hydroxide; dihydrogen peroxide In methanol at 0℃; for 24h;	A 13% B 76%

4,16-androstadien-3-one (4075-07-4) → 16β-hydroxyandrost-4-en-3-one (22614-28-4)

Conditions	Yield
Stage #1: 4,16-androstadien-3-one With mercury(II) diacetate In tetrahydrofuran; water at 20℃; for 72h; Stage #2: With sodium hydroxide; sodium tetrahydroborate In tetrahydrofuran; water for 0.0333333h;	45%

4,16-androstadien-3-one (4075-07-4) → androsta-1,4,16-trien-3-one (63015-08-7)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In toluene at 80℃; for 15h;	43%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane

4,16-androstadien-3-one (4075-07-4) → Androstene oxide (51067-43-7)

Conditions	Yield
With Perbenzoic acid; chloroform

4,16-androstadien-3-one (4075-07-4) → androsta-4,6,16-trien-3-one (63014-91-5)

Conditions	Yield
With sodium hydroxide; chloranil; acetic acid In methanol; n-heptane; water; toluene; tert-butyl alcohol; benzene
With chloranil; acetic acid In tert-butyl alcohol

4,16-androstadien-3-one (4075-07-4) + orthoformic acid triethyl ester (122-51-0) → 3-ethoxy-androsta-3,5,16-triene (63015-17-8)

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane

4,16-androstadien-3-one (4075-07-4) → 4-androsten-3-one (2872-90-4)

Conditions	Yield
With hydrogen; Wilkinson's catalyst In ethanol for 4h; Ambient temperature;	1.0 g

4,16-androstadien-3-one (4075-07-4) → androsta-4,16-dien-3α-ol + androsta-4,16-dien-3β-ol

Conditions	Yield
With ethanol; water; lithium tri-sec-butyl(hydrido)borate 1.) THF, r.t., 3 h; 2.) -55 deg C; Yield given. Multistep reaction. Yields of byproduct given;

4,16-androstadien-3-one (4075-07-4) → 16β-trichloroacetoxyandrost-4-en-3-one (406919-61-7)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: mercuric acetate / H2O; tetrahydrofuran / 72 h / 20 °C 1.2: 45 percent / 3.0 M NaOH; NaBH4 / H2O; tetrahydrofuran / 0.03 h 2.1: 83 percent / Et3N; N,N-dimethylaminopyridine / CH2Cl2 / 2.5 h / 0 - 20 °C View Scheme

4,16-androstadien-3-one (4075-07-4) → 5α-androstan-5-ol (20311-30-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.0 g / hydrogen / chloro-tris(triphenylphosphine)rhodium / ethanol / 4 h / Ambient temperature 2: 1.) 1,2-ethanedithiol, boron trifluoride etherate; 2.) methanol / 2.) Raney-Ni / 1.) acetic acid, r.t., 2 d; 2.) 20 h 3: 1.) m-chloroperbenzoic acid; 2.) lithium aluminium hydride / 1.) CHCl3, r.t., 1 h; 2.) dioxane, reflux, 4 h View Scheme

4,16-androstadien-3-one (4075-07-4) → 3H-androst-4-ene (38544-66-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.0 g / hydrogen / chloro-tris(triphenylphosphine)rhodium / ethanol / 4 h / Ambient temperature 2: 1.) 1,2-ethanedithiol, boron trifluoride etherate; 2.) methanol / 2.) Raney-Ni / 1.) acetic acid, r.t., 2 d; 2.) 20 h View Scheme

4,16-androstadien-3-one (4075-07-4) → 5β-androstan-5-ol

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.0 g / hydrogen / chloro-tris(triphenylphosphine)rhodium / ethanol / 4 h / Ambient temperature 2: 1.) 1,2-ethanedithiol, boron trifluoride etherate; 2.) methanol / 2.) Raney-Ni / 1.) acetic acid, r.t., 2 d; 2.) 20 h 3: 1.) m-chloroperbenzoic acid; 2.) lithium aluminium hydride / 1.) CHCl3, r.t., 1 h; 2.) dioxane, reflux, 4 h View Scheme

4,16-androstadien-3-one (4075-07-4) → androsta-1,4,6,16-tetraen-3-one

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / 1,4-dioxane 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,4-dioxane View Scheme

4,16-androstadien-3-one (4075-07-4) → 6β-Iodandrosta-4,16-dien-3-on

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid / 1,4-dioxane 2: (i) N-iodo-succinimide, (ii) (hydrolysis) View Scheme

4,16-androstadien-3-one (4075-07-4) → 3-ethoxy-6-chloro-androsta-3,5,16-triene (63015-22-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / 1,4-dioxane 2: (i) N-chloro-succinimide, acetone, H2O, (ii) (hydrolysis) 3: toluene-4-sulfonic acid View Scheme

Upstream product

• 36025-82-8 3-oxoandrost-4-en-17α-yl benzoate 
• 1224-94-8 HAD 
• 58-22-0 testosterone 
• 19865-18-0 17β-methoxycarbonyloxy-androst-4-en-3-one 
• 1255-57-8 17β-tosyloxyandrostan-4-en-3-one 
• 3396-11-0 cesium acetate 
• 182243-71-6 Chloro-methanesulfonic acid (8R,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl ester 
• 159949-15-2 testosterone triflate 
• 161061-98-9 Estra-5⁽¹⁰⁾,16-dien-3-one 
• 64-17-5 ethanol 
• 30505-67-0 5α-5,16-Androstadien-3α-ol 
• 1131428-48-2 3-methoxyandrosta-3,5-dien-17-one hydrazone 
• 120-72-9 indole 
• 100772-35-8 17-iodoandrosta-4,16-dien-3-one 

Downstream Products

• 51067-43-7 Androstene oxide 
• 2872-90-4 4-androsten-3-one 
• 20311-30-2 5α-androstan-5-ol 

Relevant academic research and scientific papers

Merging Halogen-Atom Transfer (XAT) and Cobalt Catalysis to Override E2-Selectivity in the Elimination of Alkyl Halides: A Mild Route towardcontra-Thermodynamic Olefins

We report here a mechanistically distinct tactic to carry E2-type eliminations on alkyl halides. This strategy exploits the interplay of α-aminoalkyl radical-mediated halogen-atom transfer (XAT) with desaturative cobalt catalysis. The methodology is high-yielding, tolerates many functionalities, and was used to access industrially relevant materials. In contrast to thermal E2 eliminations where unsymmetrical substrates give regioisomeric mixtures, this approach enables, by fine-tuning of the electronic and steric properties of the cobalt catalyst, to obtain high olefin positional selectivity. This unprecedented mechanistic feature has allowed access tocontra-thermodynamic olefins, elusive by E2 eliminations.

Alkynylation of steroids via Pd-free Sonogashira coupling

Cu-catalyzed Pd-free Sonogashira coupling has been proposed as a straightforward and convenient route to valuable steroidal enynes. A biligand catalyst system based on Ph3P and TMEDA has been designed. The protocol was utilized for the efficient coupling of iodosteroids with diverse terminal alkynes and 1-trimethylsilylalkynes. A possible role of an auxiliary ligand as a phase-transfer catalyst for a sparingly soluble inorganic base (K2CO3) was revealed.

An efficient approach to azolyl-substituted steroids through copper-catalyzed Ullmann C-N coupling

Ullmann-type C-N coupling of vinyliodides and nitrogen heterocycles has been shown to be a straightforward and highly efficient approach to azolyl-substituted steroids. The amination reaction proved sensitive to steric effects exerted by the substituents in both iodide and heterocycle. The influence of reaction conditions (catalyst, base, solvent, and temperature) on conversion of the iodosteroid and the selectivity was investigated. The catalytic system comprising 10 mol-% CuI and 20 mol-% dipivaloylmethane with K2CO3 in dimethyl sulfoxide at 100 °C delivered the best result. The elaborated protocol has permitted iodosteroids with various substituted indoles, imidazoles, carbazole, indazole, and sec-amides to be coupled, affording the corresponding azolyl-substituted steroids in good to excellent yields. A facile synthetic route to azolyl-substituted steroids has been developed on the basis of Cu-catalyzed cross-coupling of steroidal vinyliodides and aromatic NH-heterocycles. The protocol has been shown to be convenient and highly efficient, affording coupling products in good to excellent yields. Copyright

Convenient synthesis of monomeric steroids from steroidal oxalate dimers using flash vacuum pyrolysis (FVP)

Flash vacuum pyrolysis (FVP) or thermolysis (FVT), an environmentally friendly method for studying organic reaction mechanisms as well as synthesis, was applied to a series of oxalate dimers (1, 3, 5, 7, 9, 11, 13, and 15) to synthesise monomeric enes, dienes, and a triene (2, 4, 6, 8, 10, 12, 14, and 16). All steroidal monomers were identified by spectroscopic means. TUBITAK.

Androstane steroids as neurochemical initiators of change in human hypothalamic function and related pharmaceutical compositions and methods

The invention relates to a method of altering hypothalamic function in an individual. The method comprises nasally administering a human semiochemical, e.g. an Androstane steroid, or a pharmaceutical composition containing a semiochemical, such that the ligand semiochemical binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers. Other embodiments of the invention include pharmaceutical compositions containing the steroids.

Steroids as neurochemical stimulators of the VNO to alleviate pain

The invention relates to a method of alleviating pain. The method comprises nasally administering a steroid which is a human vomeropherin, such that the vomeropherin binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers.

Synthesis of trichiliasterones A and B - 16-ketosteroids isolated from Trichilia hirta and Trichilia americana

The syntheses of trichiliasterone A (3b-hydroxypregnan-2,16-dione) and trichiliasterone B (2-hydroxyandrost-1,4-diene-3,16-dione) have been carried out starting from isoandrosterone and testosterone acetate, respectively. In each synthesis the functionality in the D ring was installed prior to working on ring A. In the case of trichiliasterone A, the D ring chemistry involved a Wittig reaction to generate the 17-methylene group, followed by SeO2 oxidation to give an a,b-unsaturated ketone. Reaction with lithium dimethyl cuprate gave the required 17-ethyl-16-keto functionality. A 2,3-epoxy enol acetate served as the key intermediate for the generation of the 2-keto-3-hydroxy functions in ring A. The transposition of the keto function from C-16 to C-17 in the synthesis of trichiliasterone B was accomplished via oxymercuration-demercuration of the D16-17 double bond followed by oxidation. The hydroxyl group at C-2 and the additional ring A unsaturation were introduced by lead tetra-acetate treatment of the 3-keto-4-enone function and subsequent air oxidation.

Steroids as neurochemical stimulators of the VNO to treat paroxistic tachycardia

The invention relates to a method of alleviating the symptoms of PMS and anxiety. The method comprises nasally administering a steroid which is a human vomeropherin, such that the vomeropherin binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers.

Steroids as neurochemical stimulators of the VNO to alleviate symptoms of PMS and anxiety

The invention relates to a method of alleviating the symptoms of PMS and anxiety. The method comprises nasally administering a steroid which is a human vomeropherin, such that the vomeropherin binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers.

Steroids as neurochemical initiators of change in human blood levels of LH

The invention relates to a method of altering the blood levels of LH or FSH in an individual. The method comprises nasally administering a steroid which is a human vomeropherin, such that the vomeropherin binds to a specific neuroepithelial receptor. The steroid or steroids is/are preferably administered in the form of a pharmaceutical composition containing one or more pharmaceutically acceptable carriers.