110187-19-4

Basic information

• Product Name: ostopanic acid
• Synonyms: ostopanic acid;(8E,10E)-7,12-Dioxo-8,10-octadecadienoic acid
• CAS NO: 110187-19-4
• Molecular Formula: C18H28 O4
• Molecular Weight: 308.41
• Mol File: 110187-19-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 493.6°Cat760mmHg
• Flash Point: 266.4°C
• Appearance: /
• Density: 1.022g/cm³
• Vapor Pressure: 4.35E-11mmHg at 25°C
• Refractive Index: 1.489
• CAS DataBase Reference: ostopanic acid(CAS DataBase Reference)
• NIST Chemistry Reference: ostopanic acid(110187-19-4)
• EPA Substance Registry System: ostopanic acid(110187-19-4)

Safety Data

• Hazardous Substances Data: 110187-19-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H28O4/c1-2-3-4-6-11-16(19)13-9-10-14-17(20)12-7-5-8-15-18(21)22/h9-10,13-14H,2-8,11-12,15H2,1H3,(H,21,22)/b13-9+,14-10+

Upstream product

• 122947-37-9 (8E,10E)-8,10-octadecadiene-1,7,12-triol 
• 243120-86-7 7,12-dihydroxy-1-tert-butyldimethylsilyloxyoctadeca-8,10-diene 
• 3761-92-0 n-hexylmagnesium bromide 
• 3588-17-8 trans,trans-muconic acid 
• 869-10-3 diethyl 2,5-dibromoadipate 
• 122947-33-5 heptanedioic acid monoethyl ester potassium salt 
• 122947-34-6 ethyl 8-diazo-7-oxooctanoate 
• 111-25-1 1-bromo-hexane 
• 2050-20-6 diethyl pimelate 
• 3777-70-6 2-hexylfuran 
• 14794-32-2 ethyl 6-(chloroformyl)hexanoate 
• 143160-05-8 7,12-Dihydroxy-octadec-8-ynoic acid ethyl ester 
• 72957-73-4 undec-1-yn-5-ol 
• 18498-59-4 4-pentyn-1-al 

Relevant articles and documents

Total Synthesis of Ostopanic Acid, a Plant Cytotoxin, via Cyclopropanation of 2-n-Hexylfuran

The cyclopropanation of 2-n-hexylfuran with ethyl 8-diazo-7-oxooctanoate catalyzed by dirhodium tetraacetate as a key step for synthesis of ostopanic acid is reported.This reaction allowed the preparation of ethyl ostopanate (5) and its unstable regioisomer (10) in 58percent yield.Exposure of the mixture to a catalytic amount of iodine in dichloromethane afforded pure ethyl ostopanate, which was converted to the target compound in two steps.

A facile and stereoselective synthesis of dienediones and 6-oxo-2,4-dienoic esters

Ostopanic acid and ethyl 6-oxodocosa-2,4-dienoate were synthesized by a short route based on the palladium catalyzed isomerization of ynone and ynoic ester, respectively, using pent-4-ynal as a starting material.

Reinvestigation on the Catalytic Isomerisation of Carbon-Carbon Triple Bonds

Based on the discovery that phosphines could catalyse the isomerisation of triple bonds, the isomerisation of acetylenic derivatives was differentiated into two types: phosphine-catalysed and transition metal-catalysed.