81834-84-6

Basic information

• Product Name: 15-deoxy-16-methyl-16-hydroxy-3,4-didehydroprostaglandin E2 methyl ester
• Synonyms: 15-deoxy-16-methyl-16-hydroxy-3,4-didehydroprostaglandin E2 methyl ester
• CAS NO: 81834-84-6
• Molecular Formula: C22H34O5
• Molecular Weight: 378.50236
• Mol File: 81834-84-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 509.9°Cat760mmHg
• Flash Point: 167.4°C
• Appearance: /
• Density: 1.106g/cm³
• Vapor Pressure: 1.56E-12mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: 15-deoxy-16-methyl-16-hydroxy-3,4-didehydroprostaglandin E2 methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 15-deoxy-16-methyl-16-hydroxy-3,4-didehydroprostaglandin E2 methyl ester(81834-84-6)
• EPA Substance Registry System: 15-deoxy-16-methyl-16-hydroxy-3,4-didehydroprostaglandin E2 methyl ester(81834-84-6)

Safety Data

• Hazardous Substances Data: 81834-84-6(Hazardous Substances Data)

Usage

InChI:InChI=1/C22H34O5/c1-4-5-14-22(2,26)15-10-12-18-17(19(23)16-20(18)24)11-8-6-7-9-13-21(25)27-3/h6-10,12,17-18,20,24,26H,4-5,11,13-16H2,1-3H3/b8-6-,9-7+,12-10+/t17-,18-,20-,22-/m1/s1

Upstream product

• 105430-91-9 (+/-)-methyl 11α,16-dihydroxy-16-methyl-9-oxoprosta-3(E),13(E)-dien-5-yn-1-oate 
• 54594-85-3 methyl 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-5(Z)-heptenoate 
• 102494-28-0 (+/-)-methyl 7-<3-<(triethylsilyl)oxy>-5-oxo-1-cyclopenten-1-yl>-5(Z)-heptenoate 
• 32804-66-3 methyl 3-butynoate 
• 105430-89-5 methyl (E)-4-iodobut-3-en-1-oate 
• 105430-90-8 (+/-)-methyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-16-methyl-11α-<(triethylsilyl)oxy>-16-<(trimethylsilyl)oxy>prosta-3(E),8,13(E)-trien-5-yn-1-oate 

Relevant articles and documents

Synthesis and Gastrointestinal Pharmacology of a 3E,5Z Diene Analogue of Misoprostol

A stereospecific synthesis and the gastric antisecretory and diarrheal activity of a 3E,5Z diene analogue of misoprostol are described.The key intermediate in the synthesis was an α chain truncated acetylene that was obtained by a cuprate/enolate capture procedure on the corresponding cyclopentenone.Palladium-catalyzed coupling of the acetylene with methyl 4-iodo-3(E)-butenoate provided the conjugated enyne.Although selected hydrogenation of the enyne with Lindlar catalyst failed, the desired 3E,5Z diene was obtained with P-2 nickel as a catalyst.The diene was about 3 times more potent than misoprostol in inhibiting gastric acid secretion in dogs and also in producing diarrhea in rats.