633-35-2

Usage

Uses

Used in Pharmaceutical Industry:
Androsta-1,4,6-triene-3,17-dione is used as a pharmaceutical intermediate for the synthesis of various steroidal drugs. Its unique structure allows it to be a key component in the development of medications targeting hormonal imbalances and related conditions.
Used in Hormone Research:
In the field of endocrinology, Androsta-1,4,6-triene-3,17-dione serves as a valuable research compound for studying the effects and mechanisms of action of androstanoids on the human body. This helps in understanding the role of hormones and their impact on various physiological processes.
Used in Sports Nutrition:
Androsta-1,4,6-triene-3,17-dione is utilized as a precursor in the formulation of sports supplements designed to enhance athletic performance. Its anabolic properties can contribute to muscle growth and strength, making it a popular choice among athletes seeking to improve their physical capabilities.
Used in Cosmetic Industry:
In the cosmetics sector, Androsta-1,4,6-triene-3,17-dione is employed as an ingredient in anti-aging and skin care products. Its hormone-like effects can help improve skin elasticity, reduce the appearance of wrinkles, and promote a more youthful complexion.

InChI:InChI=1/C19H22O2/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/h3-4,7,9,11,14-16H,5-6,8,10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

Synthetic route

dehydroepiandrosterone (53-43-0) → 1,4,6-androstatriene-3,17-dione (633-35-2)

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 24h; Heating;	61%
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In 1,4-dioxane for 24h; Heating;	45%

androst-4,6-diene-3,17-dione (633-34-1) → 1,4,6-androstatriene-3,17-dione (633-35-2)

Conditions	Yield
With sodium periodate

6β-bromo-androsta-1,4-diene-3,17-dione (27759-21-3) → 1,4,6-androstatriene-3,17-dione (633-35-2)

Conditions	Yield
With 2,4,6-trimethyl-pyridine

2α,6β-dibromo-androst-4-ene-3,17-dione → 1,4,6-androstatriene-3,17-dione (633-35-2)

Conditions	Yield
With 2,4,6-trimethyl-pyridine

Androsta-1,4-diene-3,17-dione (897-06-3) → 1,4,6-androstatriene-3,17-dione (633-35-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: dibenzoyl peroxide; CCl4; N-bromo-succinimide 2: 2,4,6-trimethyl-pyridine View Scheme

1,4,6-androstatriene-3,17-dione (633-35-2) + trimethylaluminum (75-24-1) → 1α-methyl-androsta-4,6-diene-3,17-dione

Conditions	Yield
copper(I) bromide In 1,4-dioxane; water; toluene	99%
With copper(I) bromide In tetrahydrofuran for 1h; Ambient temperature;	89%

1,4,6-androstatriene-3,17-dione (633-35-2) + 2-hydroxy-2-methylpropanenitrile (75-86-5) → C20H23NO2

Conditions	Yield
With sodium carbonate In methanol; water at 20 - 45℃; Reagent/catalyst; Solvent;	98.6%
With sodium carbonate In water at 20 - 45℃; Reagent/catalyst; Solvent;	98.6%
With sodium carbonate In water at 40 - 45℃; Solvent; Reagent/catalyst;	98.6%

1,4,6-androstatriene-3,17-dione (633-35-2) → 1α,2α-epoxy-4,6-androstadiene-3,17-dione (5902-32-9)

Conditions	Yield
With dihydrogen peroxide; sodium hydroxide In methanol at 20℃; for 12h;	86%
With sodium hydroxide; dihydrogen peroxide In methanol at 20℃; for 22h;	78%

1,4,6-androstatriene-3,17-dione (633-35-2) → 1,4,6-androstatrien-3β,17β-diol (34195-01-2)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 20℃; for 24h;	83%
With sodium tetrahydroborate In ethanol at 20℃;	63%

sodium metabisulfite + oxone + 1,4,6-androstatriene-3,17-dione (633-35-2) → 6,7α-epoxyandrosta-1,4-diene-3,17-dione

Conditions	Yield
With sodium hydroxide In water; acetone	73%

1,4,6-androstatriene-3,17-dione (633-35-2) → (E)-6-hydroxyiminoandrosta-1,4-diene-3,17-dione (140421-66-5)

Conditions	Yield
With triethylsilane; tert.-butylnitrite; cobalt(II) 5,10,15,20-tetraphenylporphyrin In dichloromethane; isopropyl alcohol for 48h; Ambient temperature;	68%

1,4,6-androstatriene-3,17-dione (633-35-2) → 6-dehydrotestosterone (3591-23-9, 3593-33-7, 4030-88-0, 4223-57-8, 2484-30-2) + 1,4,6-Androstatrien-17beta-ol-3-one (4075-12-1)

Conditions	Yield
With lithium triethylborohydride In tetrahydrofuran at 20℃; for 2h;	A 65% B 13%
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1h;	A 16% B 53%

1,4,6-androstatriene-3,17-dione (633-35-2) → 6α,7α-epoxy-4,6-androstadiene-3,17-dione (55651-50-8)

Conditions	Yield
With 3-chloro-benzenecarboperoxoic acid In chloroform at 20℃;	64%
With 3-chloro-benzenecarboperoxoic acid In chloroform at 60℃; for 6h; Inert atmosphere;	61%

1,4,6-androstatriene-3,17-dione (633-35-2) → 1,4,6-androstatrien-3α,17β-diol

Conditions	Yield
With L-Selectride In tetrahydrofuran at 20℃; for 18h;	63%

1-Naphthalenethiol (529-36-2) + 1,4,6-androstatriene-3,17-dione (633-35-2) → 7α-(1'-naphthyl)thioandrosta-1,4-diene-3,17-dione + (1S,7R,8S,9S,10R,13S,14S)-10,13-Dimethyl-1,7-bis-(naphthalen-1-ylsulfanyl)-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

Conditions	Yield
With hydrogenchloride; acetic acid for 20h; Ambient temperature;	A 20% B 45%

1,4,6-androstatriene-3,17-dione (633-35-2) + 2-Naphthalenethiol (91-60-1) → 7α-(2'-naphthyl)thioandrosta-1,4-diene-3,17-dione + (1S,8S,9S,10R,13S,14S)-10,13-Dimethyl-1-(naphthalen-2-ylsulfanyl)-1,8,9,10,11,12,13,14,15,16-decahydro-2H-cyclopenta[a]phenanthrene-3,17-dione + (1S,7R,8S,9S,10R,13S,14S)-10,13-Dimethyl-1,7-bis-(naphthalen-2-ylsulfanyl)-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione

Conditions	Yield
With sodium In 1,4-dioxane at 80℃; for 18h;	A 25% B 35% C 10%

hypofluorous acid trifluoromethyl ester (373-91-1) + 1,4,6-androstatriene-3,17-dione (633-35-2) → 6α,7α-difluoroandrosta-1,4-diene-3,17-dione (82423-37-8) + 7α-fluoro-6α-trifluoromethoxyandrosta-1,4-diene-3,17-dione (82423-38-9)

Conditions	Yield
With calcium oxide In dichloromethane at -20℃;	A 15% B 30%

1,4,6-androstatriene-3,17-dione (633-35-2) → 6α,7α-difluoroandrosta-1,4-diene-3,17-dione (82423-37-8) + 7α-fluoro-6α-trifluoromethoxyandrosta-1,4-diene-3,17-dione (82423-38-9)

Conditions	Yield
With trichlorofluoromethane; calcium oxide In dichloromethane at -20℃;	A 15% B 30%

1,4,6-androstatriene-3,17-dione (633-35-2) + 4-aminotiophenol (1193-02-8) → 7α-(4'-amino)phenylthio-1,4-androstadiene-3,17-dione (110325-37-6) + (1S,8S,9S,10R,13S,14S)-1-(4-Amino-phenylsulfanyl)-10,13-dimethyl-1,8,9,10,11,12,13,14,15,16-decahydro-2H-cyclopenta[a]phenanthrene-3,17-dione (110325-38-7)

Conditions	Yield
With hydrogenchloride; acetic acid for 24h; Ambient temperature;	A 15% B 30%

1,4,6-androstatriene-3,17-dione (633-35-2) + thiophenol (108-98-5) → 7α-phenylthioandrosta-1,4-diene-3,17-dione

Conditions	Yield
With hydrogenchloride; acetic acid for 24h; Ambient temperature;	27%

1,4,6-androstatriene-3,17-dione (633-35-2) + para-bromobenzenethiol (106-53-6) → 7α-(4'-bromo)phenylthioandrosta-1,4-diene-3,17-dione

Conditions	Yield
With hydrogenchloride; acetic acid for 15h; Ambient temperature;	15%

thioacetic acid (507-09-5) + 1,4,6-androstatriene-3,17-dione (633-35-2) → 1α-acetylsulfanyl-androsta-4,6-diene-3,17-dione (102472-23-1)

Conditions	Yield
Einwirkung von UV-Licht;
im UV-Licht;

1,4,6-androstatriene-3,17-dione (633-35-2) → 6-dehydroestrone (2208-12-0)

Conditions	Yield
With glass at 600℃;

1,4,6-androstatriene-3,17-dione (633-35-2) + acetic anhydride (108-24-7) → 3-acetoxy-1-methyl-estra-1,3,5(10),6-tetraen-17-one (53-55-4)

Conditions	Yield
With toluene-4-sulfonic acid
With toluene-4-sulfonic acid; acetic acid

1,4,6-androstatriene-3,17-dione (633-35-2) + acetic anhydride (108-24-7) → 1-Methyl-3-acetoxy-7-acetyl-Δ1.3.5(10).6-oestratetraen-17-on (18012-02-7)

Conditions	Yield
With toluene-4-sulfonic acid; acetic acid

1,4,6-androstatriene-3,17-dione (633-35-2) → (13S,14R)-1-Hydroxy-4,13-dimethyl-6,7,11,12,13,14,15,16-octahydro-cyclopenta[a]phenanthren-17-one

Conditions	Yield
With hydrogen fluoride; antimony pentafluoride at -50℃;

1,4,6-androstatriene-3,17-dione (633-35-2) → 2-ethoxy-1,4,6-androstatrien-3β,17β-dione

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / NaOH; H2O2 / methanol / 22 h / 20 °C 2: 73 percent / lithium / 18 h / 20 °C View Scheme

1,4,6-androstatriene-3,17-dione (633-35-2) → 1α,2α-epoxy-1,4-androstadien-3β,17β-diol

Conditions	Yield
Multi-step reaction with 2 steps 1: 78 percent / NaOH; H2O2 / methanol / 22 h / 20 °C 2: 69 percent / NaBH4 / ethanol / 20 °C View Scheme

1,4,6-androstatriene-3,17-dione (633-35-2) → 4β,5β-epoxyandrost-6-en-3β,17β-diol

Conditions	Yield
Multi-step reaction with 2 steps 1: 63 percent / NaBH4 / ethanol / 20 °C 2: 64 percent / m-chloroperoxybenzoic acid / CHCl3 / 20 °C View Scheme

Upstream product

• 633-34-1 androst-4,6-diene-3,17-dione 
• 27759-21-3 6β-bromo-androsta-1,4-diene-3,17-dione 
• 53-43-0 dehydroepiandrosterone 
• 897-06-3 Androsta-1,4-diene-3,17-dione 

Downstream Products

• 110325-37-6 7α-(4'-amino)phenylthio-1,4-androstadiene-3,17-dione 
• 110325-38-7 (1S,8S,9S,10R,13S,14S)-1-(4-Amino-phenylsulfanyl)-10,13-dimethyl-1,8,9,10,11,12,13,14,15,16-decahydro-2H-cyclopenta[a]phenanthrene-3,17-dione 
• 66212-25-7 1,4,6-triene-3,20-dione-17α-hydroxyprogesterone 
• 15262-77-8 delmadinone 
• 13698-49-2 6-chloro-17a-acetoxy-pregnane-1,4,6-,triene-3,20-dione 
• 3597-38-4 1-Methyl-estradiol 
• 116031-38-0 3-benzoyloxy-1-methyl-estra-1,3,5(10),6-tetraen-17β-ol 
• 10506-68-0 1-methyl-estra-1,3,5(10),6-tetraene-3,17β-diol 
• 3129-08-6 1-Methyl-6-dehydro-oestron 
• 152953-22-5 7α-<4'-(3'',3''-dimethylazido)phenyl>thioandrosta-1,4-diene-3,17-dione 
• 3591-23-9 6-dehydrotestosterone 
• 4075-12-1 1,4,6-Androstatrien-17beta-ol-3-one 
• 2208-12-0 6-dehydroestrone 

Relevant academic research and scientific papers

NOVEL COMPOSITION TO INCREASE LIBIDO

The present invention relates to a composition for increasing testosterone physiological levels comprising a sufficient amount of at least two ketosteroid derivatives of testosterone metabolism in association with a liposomal carrier bound to a saliva-absorbing carrier, wherein said increase in testosterone levels increases libido.

Chemoselective reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by various hydride reagents

The chemoselectivity of rigid cyclic α,β-unsaturated carbonyl group on the reducing agents was influenced by the ring size and steric factor. Cholesterol (cholest-5-en-3β-ol) and dehydroepiandrosterone (DHEA) were oxidized with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone to form 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione. They were reduced with NaBH4, lithium tri-sec-butylborohydride (l-Selectride), LiAlH4, 9-borabicyclo[3.3.1]nonane (9-BBN), lithium triethylborohydride (Super-hydride), and BH3·(CH3)2S in various conditions, respectively. Reduction of 1,4,6-cholestatrien-3-one and 1,4,6-androstatriene-3,17-dione by NaBH4 (4 equiv.) produced 4,6-cholestadien-3β-ol and 4,6-androstadiene-3β,17β-diol, respectively. Reduction by l-Selectride (12 equiv.) afforded 4,6-cholestadien-3α-ol and 4,6-androstadiene-3α,17β-diol, chemoselectively. Reaction with Super-hydride (12 equiv.) produced 4,6-cholestadien-3-one and 3-oxo-4,6-androstadien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by 9-BBN (14 equiv.) produced 1,4,6-cholestatrien-3α-ol, but 1,4,6-androstatriene-3,17-dione was not reacted with 9-BBN in the reaction conditions. Reaction of LiAlH4 (6 equiv.) formed 4,6-cholestadien-3β-ol and 3-oxo-1,4,6-androstatrien-17β-ol. Reduction of 1,4,6-cholestatrien-3-one by BH3·(CH3)2S (11 equiv.) gave cholestane as major compound and unlike reactivity of cholesterol, 1,4,6-androstatriene-3,17-dione by 8 equiv. of BH3·(CH3)2S formed 3-oxo-1,4,6-androstatrien-17β-ol. LiAlH4 and BH3·(CH3)2S showed relatively low chemoselectivity.

Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol

Dehydroepiandrosterone (DHEA) reacted with m-chloroperoxybenzoic acid (m-CPBA) to form 3β-hydroxy-5α,6α-epoxyandrostan-17-one (1), but it did not react with 30 percent H2O2. 1,4,6-Androstatrien-3,17-dione (2) was obtained from DHEA and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in dioxane. Compound 2 was reacted with 30 percent H2O2 and 5 percent NaOH in methanol to give 1α,2α-epoxy-4,6-androstadien-3,17-dione (3), which was stereoselectively reduced with NaBH4 to form 1α,2α-epoxy-4,6-androstadien-3β,17β-diol (7) and reacted with Li metal in absolute ethanol-tetrahydrofuran mixture to give 2-ethoxy-1,4,6-androstatrien-3,17-dione (8). Compound 2 was also epoxidized with m-CPBA in dichloromethane to afford 6α,7α-epoxy-1,4- androstadien-3,17-dione (4), which was reacted with NaBH4 to synthesize 6α,7α-epoxy-4-androsten-3β,17β-diol (9). Compound 4 was reduced with Li metal in absolute ethanol-tetrahydrofuran mixture to form 7β-ethoxy-6α-hydroxy-1,4-androstadien-3,17-dione (10). Compound 2 was reduced with NaBH4 in absolute ethanol to form 4,6-androstadien-3β,17β-diol (5), which was reacted with 30 percent H2O2 to give the original compound, but which reacted with m-CPBA to give 4β,5β-epoxy-6-androsten-3β,17β-diol (6).

Use of aromatase-inhibitors for prophylaxis and/or treatment of benign prostatic hyperplasia

Aromatase-inhibitors are used in a method of prophylaxis and/or treatment by therapy of prostatic hyperplasia. Pharmaceutical preparations suitable for such a use comprise an aromatase-inhibitor. A particularly preferred aromatase-inhibitor is, for example, testolactone.

Electrophilic Fluorination of Some Steroidal α,β-Unsaturated Ketones

3β-Acetoxy-5α,6β-dichloropregn-16-en-20-one (1), on treatment with elemental fluorine at low temperature, gave the 16α,17α-difluoro-adduct (2) and, by rearrangement, the 13α,16α-difluoro-17β-methyl derivative (3).The adduct (2) was subsequently converted via a short, efficient synthetic sequence into 16α,17α-difluoroprogesterone (5).In contrast, fluorination of 21-acetoxypregna-1,4,16-triene-3,11,20-trione (6) afforded the corresponding 16α,17α-difluoro-adduct (8) in low yield.Similarly, androsta-1,4,6-triene-3,17-dione (9) was converted into the 6α,7α-difluoro-adduct (11).Fluorination with CF3OF led to an increased yield of the adduct (11) and also afforded the 6α-trifluoromethoxy-7α-fluoro-adduct (12).Dehydrofluorination of the latter gave 6-trifluoromethoxyandrosta-1,4,6-triene-3,17-dione (13). 21-Acetoxy-11β,17α-dihydroxypregna-1,4,6-triene-3,20-dione (5) was prepared by stepwise dehydrogenation of cortisol acetate (14).Subsequent low temperature treatment with CF3OF resulted in two major products, formulated as the adducts (17) and (18).