60900-56-3

Usage

InChI:InChI=1/C19H34O4/c1-3-4-12-15-18(23-21)16-13-10-8-6-5-7-9-11-14-17-19(20)22-2/h8,10,13,16,18,21H,3-7,9,11-12,14-15,17H2,1-2H3/b10-8+,16-13+

Upstream product

• 109061-18-9 methyl <1-(14)C>13-hydroperoxy-9,11-octadecadienoate 
• 112-63-0 Methyl linoleate 
• 71-43-2 benzene 
• 186581-53-3 diazomethane 
• 60-33-3 linoleic acid 

Downstream Products

• 3777-69-3 2-pentylfuran 
• 17289-34-8 α-pyrrole ethylbenzene 
• 505-57-7 2-hexenal 
• 2548-87-0 2-octen-1-al 
• 111-11-5 methyl octanate 
• 2363-88-4 deca-2,4-dienal 
• 122-78-1 phenylacetaldehyde 
• 100-52-7 benzaldehyde 
• 66-25-1 hexanal 
• 10219-69-9 (R,S)-coriolic acid 
• 54739-30-9 13-oxo-9Z,11E-octadecadienoic acid 
• 4179-43-5 9-(-5-pentyl-2-furyl)nonanoic acid 
• 79790-32-2 13-oxo-(9Z,11E)-octadecadien-1-oic acid methyl ester 
• 5502-90-9 (9Z,11E)-13-hydroperoxyoctadeca-9,11-dienoic acid 

Relevant academic research and scientific papers

Evidence for hydroxyl radical generation during lipid (linoleate) peroxidation

The autoxidation of methyl linoleate in benzene at 37 °C by peroxyl radicals was found to generate hydroxyl radicals (?OH) from a secondary oxidation mechanism. The yield of hydroxyl radicals (～2%) was determined by trapping these reactive radicals with benzene to give phenol. We propose that αC-H hydrogen abstraction from lipid hydroperoxides, the main autoxidaion products, is the source of hydroxyl radicals. Copyright

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).

Formation of Fluorescent Substances in the Reaction of the Hydroperoxide Isomers of Metyl Linoleate and Amylamine

The formation of fluorescent substances through the reaction of degradation products of four geometrical isomers of methyl linoleate hydroperoxides with amylamine was studied.The 9- and 13-positional monohydroperoxide isomers having the cis-trans and trans-trans configurations were separated from autoxidized methyl linoleate by high performance liquid chromatography (HPLC) and their abilities to form fluorescent substances with amylamine in the presence of heme were compared.These four isomers produced the same fluorescent substances exhibiting excitation and emmision maxima at 350 and 420 nm, respectively, and also showed the same abilities for fluorescence formation and the same elution profiles of fluorescent substances (FS-I and FS-II) on HPLC.This study proved that all four geometrical isomers were involved in the production of fluorescent substances upon reaction with amino compounds. Keywords --- lipid peroxidation; methyl linoleate; 9-hydroperoxide; 13-hydroperoxide; hydroperoxide geometrical isomer; fluorescence