125559-74-2

Usage

Uses

9-OxoOTrE is an oxidation product of 9-HpOTrE with antimicrobial properties.

Upstream product

• 89886-42-0 (9S,10E,12Z,15Z)-9-hydroxyoctadeca-10,12,15-trienoic acid 
• 463-40-1 (9Z,12Z,15Z)-octadeca-9-12,15-trienoic acid 
• 111004-08-1 (9S,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoic acid 
• 51197-09-2 9-hydroxy-trans-10,cis-12,cis-15-octadecatrienoic acid 

Relevant academic research and scientific papers

Physcomitrella patens has lipoxygenases for both eicosanoid and octadecanoid pathways

Mosses have substantial amounts of long chain C20 polyunsaturated fatty acids, such as arachidonic and eicosapentaenoic acid, in addition to the shorter chain C18 α-linolenic and linoleic acids, which are typical substrates of lipoxygenases in flowering p

Easy access to various natural keto polyunsaturated fatty acids and their corresponding racemic alcohols

Various optically active hydroxy derivatives of polyunsaturated fatty acids were easily oxidised to their corresponding keto derivatives using Dess-Martin periodinane. The reaction was run on the millimolar scale with good yields and without appreciable isomerisation of the surrounding double bonds. Reduction of these keto compounds to yield back the starting alcohols, but now as racemic mixtures, was also conducted using CeCl3-NaBH 4, once again without noticeable modification of the stereochemistry of the double bonds. These reactions proved the usefulness of the chemoenzymatic access to oxylipins through the use of lipoxygenases with various regiospecificity, combined with chemical transformations of the formed hydro(pero)xides.

Efficient syntheses of (10E,12Z,15Z)-9-oxo- and (9Z,11E,15E)-13-oxo-octadecatrienoic acids; two stress metabolites of wounded plants

Configurationally pure 9-oxo-10E,12Z,15Z- and 13-oxo-9Z,11E,15E-octadecatrienoic acid are available from linolenic acid via regioselective functionalisation using lipoxygenases from soybean or tomato at specific pH conditions. Reduction of the resulting hydroperoxides followed by oxidation of the resulting allylic alcohols with Bobbitt's reagent yields the configurationally pure but labile ketotrienoic acids 4 and 5 without concomitant isomerisation.