156733-09-4

Basic information

• Product Name: methyl 3-(2-octadecylcyclopropen-1-yl)propanoate
• Synonyms: methyl 3-(2-octadecylcyclopropen-1-yl)propanoate
• CAS NO: 156733-09-4
• Molecular Formula: C25H46 O2
• Molecular Weight: 378.63
• Mol File: 156733-09-4.mol

Chemical Properties

• Boiling Point: 462.2°Cat760mmHg
• Flash Point: 95.7°C
• Appearance: /
• Density: 0.905g/cm³
• Vapor Pressure: 1E-08mmHg at 25°C
• Refractive Index: 1.472
• CAS DataBase Reference: methyl 3-(2-octadecylcyclopropen-1-yl)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-(2-octadecylcyclopropen-1-yl)propanoate(156733-09-4)
• EPA Substance Registry System: methyl 3-(2-octadecylcyclopropen-1-yl)propanoate(156733-09-4)

Safety Data

• Hazardous Substances Data: 156733-09-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C25H46O2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23-22-24(23)20-21-25(26)27-2/h3-22H2,1-2H3

Upstream product

• 156733-06-1 3-(1,2-Diiodo-2-octadecyl-cyclopropyl)-propionic acid 
• 156733-03-8 3-(2-octadecylcyclopopen-1-yl)tetrahydropyranyloxypropane 
• 156733-04-9 3-(1,2-diiodo-2-octadecylcyclopropyl)tetrahydropyranyloxypropane 
• 156733-05-0 3-(1,2-diiodo-2-octadecylcyclopropyl)propanol 
• 156732-95-5 C₂₁H₃₉Li 
• 153499-79-7 1,1,2-tribromo-2-octadecylcyclopropane 
• 156733-07-2 methyl 3-(1,2-diiodo-2-octadecylcyclopropyl)propanoate 

Relevant articles and documents

Synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate and methyl 3-(2-octadecylcyclopropen-1-yl)pentanoate and cyclopropane fatty acids as possible inhibitors of mycolic acid biosynthesis

(Z)-Tetracos-5-enoic acid is a key intermediate in the biosynthesis of mycobacterial mycolic acids. Recently the methyl ester of its cyclopropene analogue, methyl 4-(2-octadecylcyclopropen-1-yl)butanoate, was shown to act as an inhibitor of mycolic acid biosynthesis. The related analogues methyl 5-(2-octadecylcyclopropen-1-yl)pentanoate and methyl 3-(2-octadecylcyclopropen-1-yl)propanoate have been synthesised, as well as the related cyclopropane esters methyl (Z)-4-(2-octadecylcyclopropan-1-yl)butanoate and methyl (Z)-5-(2-octadecylcyclopropan-1-yl)pentanoate. The synthesis of methyl 3-(2-octadecylcyclopropen-1-yl)propanoate involved protection of the cyclopropene ring by iodination to allow oxidation of an alcohol to a carboxylic acid; the diiodocyclopropane was deprotected by a new mild procedure using activated zinc.