64265-96-9

Upstream product

• 186581-53-3 diazomethane 
• 60-33-3 linoleic acid 
• 112-63-0 Methyl linoleate 

Downstream Products

• 5204-87-5 Octadeca-8t,10t,12c-triensaeure 

Relevant academic research and scientific papers

Allylic oxidation: Easy synthesis of alkenones from activated alkenes with TEMPO

Activated alkenes and dienes are converted into the corresponding alkenone in excellent yields (>90%). In aqueous acetonitrile, the transformations are catalyzed by 2,2,6,6-tetramethyl-1-oxopiperidinium (TEMPO+) in the presence of water and 2,6-lutidine. TEMPO+ cations were regenerated electrochemically from the radical parent (TEMPO.) at a vitreous carbon anode.

New geometric isomers of oxooctadecadienoate in copper-catalyzed decomposition products of linoleate hydroperoxide

Methyl linoleate hydroperoxide produced by autoxidation was refluxed with 10-4 M Cu-naphthenate in benzene. Two new geometrical isomers of oxooctadecadienoate (compounds I and II) were found in addition to the four known isomers. They were isolated by a Sephadex LH-20 column chromatography with chloroform-hexane (2:1) and purified by HPLC on Nucleosil 100-5 and Zorbax ODS columns. UV, IR, MS, and 1H-NMR spectra were measured. The geometry of conjugated dienes were assigned from the coupling constants of the olefinic protons. Compounds I and II were identified as 13-oxo-trans-9, cis-11- and 9-oxo-cis-10, trans-12-octadecadienoate, respectively. Each of them had a cis double bond adjacent to the oxo group. The hydroperoxides of the same geometry as compounds I and II were also detected in autoxidation products.

Synthesis of keto- and hydroxydienoic compounds from linoleic acid

A convenient preparative method has been developed for the synthesis of hydroxydienoic (9-HODE and 13-HODE) and ketodienoic compounds (9-KODE and 13-KODE) from natural linoleic acid. Methyl linoleate was treated with 1.25 eq. of m-chloroperbenzoic acid in alcoholic solution, giving a mixture of mono-epoxides (yield 60%), that was treated with a solution of HBr in MeOH to yield a mixture of the bromohydrins (yield 92%). The last was oxidized by Jones reagent to a mixture of bromoketones (yield 64%) and the mixture obtained was dehydrobrominated by DBU to produce a mixture of ketodienoic compounds (yield 94%). Reduction of the ketodienoic compounds by KBH4 in MeOH led to the corresponding hydroxydienoic (9-HODE and 13-HODE) methyl esters (yield 83%). The synthetic approach described is simple and gives reliable results. The keto- and hydroxy fatty acids obtained were characterized thoroughly by TLC, HPLC, UV, FT-IR, 1H-, 1H1H- and 13C-NMR.

IRON-PEPLOMYCIN CATALYZED OXYGENATION OF LINOLEIC ACID

Incubation of linoleic acid with Fe(III)-peplomycin under aerobic conditions produced a mixture of hydroperoxides 1a-d as primary products which then gave rise to the formation of the corresponding dienones (2a-d), alcohols (3a-d) and epoxyenones (4a,b).