108180-16-1

Basic information

• Product Name: 10-thiirane-4-estrene-3,17-dione
• Synonyms: 10-thiirane-4-estrene-3,17-dione
• CAS NO: 108180-16-1
• Molecular Formula: C20H26O2S
• Molecular Weight: 330.48424
• Mol File: 108180-16-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 503.5°Cat760mmHg
• Flash Point: 215.1°C
• Appearance: /
• Density: 1.23g/cm³
• Vapor Pressure: 2.9E-10mmHg at 25°C
• Refractive Index: 1.605
• CAS DataBase Reference: 10-thiirane-4-estrene-3,17-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 10-thiirane-4-estrene-3,17-dione(108180-16-1)
• EPA Substance Registry System: 10-thiirane-4-estrene-3,17-dione(108180-16-1)

Safety Data

• Hazardous Substances Data: 108180-16-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C20H26O2S/c1-19-8-7-16-14(15(19)4-5-17(19)22)3-2-12-10-13(21)6-9-20(12,16)18-11-23-18/h10,14-16,18H,2-9,11H2,1H3/t14-,15-,16-,18-,19-,20?/m0/s1

Upstream product

• 38309-06-7 19-oxoandrost-5-ene-3β,17β-diol bis(tetrahydropyranyl ether) 
• 108180-14-9 (19R)-10β-oxiranyl-4-estrene-3,17-dione 
• 108180-15-0 (19S)-10β-oxiranylestr-4-ene-3β,17β-dione 
• 116865-19-1 (19S)-10β-oxiranylestr-5-ene-3β,17β-diol 

Relevant articles and documents

Novel 10β-thiiranyl steroids as aromatase inhibitors

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Stereoselective inhibition of human placental aromatase

We have synthesized the (19R)- and (19S)-isomers (2 and 3 respectively) of 10β-oxiranylestr-4-ene-3,17-dione.The configurations and conformations of these compounds were established by X-ray crystallographic analysis.Each of these compounds is a powerful competitive inhibitor of human placental microsomal aromatase, and stereoselectivity of inhibition was observed (Ki values for 2 and 3 were 7 and 75 nanomolar, respectively).Spectroscopic studies with purified aromatase indicate that the inhibition process involves reversible binding of oxirane oxygen to the heme iron of the enzyme.The (19R)- and (19S)-10β-thiiranes ( 6 and 7) corresponding to 2 and 3 have been synthesized from the oxiranes by a stereospecific process.The thiiranes are very effective competitive inhibitors of placental aromatase, and show even greater stereoselectivity in binding than the oxiranes (Ki values for 6 and 7 were 1 and 75 nanomolar, respectively).Spectroscopic studies with purified aromatase indicate that the inhibition process involves reversible binding of thiirane sulfur to heme iron.