1912-63-6

Basic information

• Product Name: 3,5-androstadien-17-one
• Synonyms: 3,5-androstadien-17-one;Androsta-3,5-dien-17-one;17-Keto-3,5-androstadiene
• CAS NO: 1912-63-6
• Molecular Formula: C₁₉H₂₆O
• Molecular Weight: 0
• Mol File: 1912-63-6.mol
• Article Data: 19

Chemical Properties

• Appearance: /
• Storage Temp.: ?20°C
• CAS DataBase Reference: 3,5-androstadien-17-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-androstadien-17-one(1912-63-6)
• EPA Substance Registry System: 3,5-androstadien-17-one(1912-63-6)

Safety Data

• Hazardous Substances Data: 1912-63-6(Hazardous Substances Data)

Usage

Uses

Androsta-3,5-dien-17-one is a steroid which can inhibit aromatase in human placental microsomes. This compound is also found in the scent of reticulated giraffe which can be detected by humans. It may deter microorganisms or ectoparasitic arthropods.

InChI:InChI=1/C19H26O/c1-18-11-4-3-5-13(18)6-7-14-15-8-9-17(20)19(15,2)12-10-16(14)18/h3,5-6,14-16H,4,7-12H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1

Upstream product

• 53-43-0 dehydroepiandrosterone 
• 103232-84-4 3,3:6,6-bis(ethylenedithio)-4-androsten-17-one 
• 71-43-2 benzene 
• 7758-99-8 copper(II) sulfate 
• 63-05-8 Androstenedione 
• 2243-06-3 androst-4-ene-3,6,17-trione 
• 2719-96-2 3β-tosyloxyandrost-5-ene-17-one 
• 10534-59-5 tetrabutylammonium acetate 
• 10417-80-8 3β-acetoxy-17,17-ethanediyldimercapto-androst-5-ene 
• 28865-17-0 2β,3α-Dibrom-5α,6β-dichlor-androstan-17-on 
• 2602-86-0 (17β)-androsta-3,5-dien-17-ol 
• 2428-57-1 Δ⁴-Androsten-3β-ol-17-on-cycloaethylenketal 
• 119402-66-3 17-Oxoandrosta-3,5-dien<3,4-b>(5,6-dihydro-1,4-dithiin) 
• 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 

Downstream Products

• 963-74-6 5alpha-androstan-17-one 
• 6020-93-5 androstadien-(3.5)-one-(17)-oxime 
• 972-46-3 3-ethoxyandrosta-3,5-dien-17-one 
• 76183-43-2 5α-(m-chlorobenzoyloxy)-3α,4α-epoxyandrostan-6β-ol 
• 76183-44-3 5α-(m-chlorobenzoyloxy)androst-3-en-6β-ol 
• 76183-45-4 4β-(m-chlorobenzoyloxy)androst-5-en-3α-ol 
• 63-05-8 Androstenedione 
• 2243-06-3 androst-4-ene-3,6,17-trione 
• 76183-49-8 3-(m-chlorobenzoyloxy)androsta-3,5-dien-17-one 
• 76183-46-5 3α,4α;5β,6β-diepoxyandrostan-17-one 
• 438-22-2 (5α)-androstane 

Relevant articles and documents

Synthesis of steroidal 3,5-dieno[3,4-b](5,6-dihydro-1,4-dithiins)

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Analytical chemical studies on steroids. VII. The Zimmermann complexes derived from i-androstanolone and its related 17-oxosteroids.

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Iridium-catalysed highly selective reduction-elimination of steroidal 4-en-3-ones to 3,5-dienes in water

Steroidal 3,5-diene is an important structural motif in steroid drugs. In this report, an iridium-catalyzed reduction-elimination of readily available steroidal 4-en-3-ones is realized to prepare steroidal 3,5-dienes. At a low catalyst loading (S/C = 200), heating 4-en-3-ones in a water-mixed organic solvent with formic acid without inert atmosphere protection afforded the desired 3,5-dienes in moderate to excellent yields. In a gram-scale preparation, recrystallization is used instead of column chromatography to purify products. Excellent functionality tolerance and regioselectivity are featured. Structural moieties such as alkanols (primary, secondary and tertiary), esters (except for formate), tolylates, and ketones (endocyclic or exocyclic) are not affected. Surprisingly, the reduction-elimination only takes place at A-ring 4-en-3-ones. In addition, bicyclic 4-en-3-ones are also viable substrates. Synthetic applications of steroidal 3,5-dienes are demonstrated. Our method can also lead to steroidal 3,5-dienes-3-d (>99% d-incorporation) when DCO2D and D2O are used together.

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.