Synthesis and characterization of long-chain 1,2-dioxo compounds.

Abstract:

:A series of long-chain methyl esters with vicinal oxo groups (1,2-diones; 1,2-diketones) were synthesized by potassium permanganate-based oxidation of methyl esters of mono-unsaturated fatty acids. The presence of two additional carbonyl groups may facilitate the synthesis of other derivatives. The starting materials were selected in such a fashion to give the 1,2-dioxo moiety in consecutive positions from the methyl ester group. The compounds were characterized by mass spectrometry and nuclear magnetic resonance spectroscopy. In mass spectrometry, both electron and chemical ionization (methane as reagent gas) were investigated. The position of the dioxo moiety can be determined in both ionization modes, however, in electron ionization mode the corresponding fragment ions are considerably stronger. In electron ionization mode, a fragmentation mechanism depending on the position of the 1,2-dioxo moiety occurs while the spectra derived from chemical ionization mode are mainly characterized by peaks around the molecular ion with both ionization modes appearing suitable.

journal_name

Chem Phys Lipids

authors

Knothe G

doi

10.1016/s0009-3084(02)00014-2

subject

Has Abstract

pub_date

2002-05-01 00:00:00

pages

85-91

issue

1-2

eissn

0009-3084

issn

1873-2941

pii

S0009308402000142

journal_volume

115

pub_type

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