150585-14-1

Basic information

• Product Name: 4-(3-hydroxyestra-1,3,5(10)-tetraen-16-yl)-2-methylene-4-butanolide
• Synonyms: 4-(3-hydroxyestra-1,3,5(10)-tetraen-16-yl)-2-methylene-4-butanolide
• CAS NO: 150585-14-1
• Molecular Formula: C23H26 O3
• Molecular Weight: 350.45
• Mol File: 150585-14-1.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-(3-hydroxyestra-1,3,5(10)-tetraen-16-yl)-2-methylene-4-butanolide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(3-hydroxyestra-1,3,5(10)-tetraen-16-yl)-2-methylene-4-butanolide(150585-14-1)
• EPA Substance Registry System: 4-(3-hydroxyestra-1,3,5(10)-tetraen-16-yl)-2-methylene-4-butanolide(150585-14-1)

Safety Data

• Hazardous Substances Data: 150585-14-1(Hazardous Substances Data)

Upstream product

• 150585-07-2 16-formylestra-1,3,5⁽¹⁰⁾,16-tetraen-3-ol 
• 17435-72-2 ethyl 2-bromomethyl-2-propenoate 
• 150585-12-9 16-butylthiomethylene-3-hydroxyestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 150585-13-0 16-butylthiomethylene-3,17β-dihydroxyestra-1,3,5(10)-triene 
• 3460-92-2 3-hydroxy-16-hydroxymethylideneestra-1,3,5⁽¹⁰⁾-trien-17-one 
• 53-16-7 Estrone 

Relevant articles and documents

Preparation of 16-formylestradiol and the 16-(α-methylenebutanolide) derivative

Route tot he preparation of 16-formylestradiol are described. Estronen was converted to (E)-16-methoxy-methylene estrone via the 16-hydroxymethylene estrone. Reduction of themethoxymethylene estrone with NaBH4 in the presence of CeCl3 gave 16-methoxymethylene estradiol. Deprotection by acid afforded the desired 16-formylestradiol. Attempts to prepare the 16-formylestradiol via the 16-butythio-methylene derivative gave only 16-formylestra-1,3,5(10),16-tetraen-3-ol, and a route through the 16-dimethoxymethyl derivative gave a mixture of the 16-formyltetraen-3-ol and the 16-formlestradiol in low yield. The 16-formylestradiol was subsequently converted tot he α-methylene lactone conjugate, 4-(3,17β-dihydroxyestra-1,3,5(10)trien-16-yl)-2-methylene-4-butanolide by reaction with methyl α-(bromomethyl) acrylate and zinc. (Steroids 58: 234-238, 1993).