91097-63-1

Upstream product

• 91173-04-5 methyl (5Z)-8-iodooct-5-enoate 
• 603-35-0 triphenylphosphine 
• 6026-86-4 methyl 4-formylbutanoate 
• 1072-59-9 1-methoxycyclopentene 
• 83606-22-8 (Z)-8-hydroxyoct-5-enoic acid methyl ester 
• 116099-25-3 methyl (Z)-8-((tetrahydro-2H-pyran-2-yl)oxy)oct-5-enoate 

Downstream Products

• 128860-97-9 (5Z,8Z,10E)-(S)-12-(tert-Butyl-diphenyl-silanyloxy)-heptadeca-5,8,10-trienoic acid methyl ester 
• 128860-96-8 (5Z,8Z,10E)-(R)-12-(tert-Butyl-diphenyl-silanyloxy)-heptadeca-5,8,10-trienoic acid methyl ester 
• 109296-17-5 7-carbomethoxy hepta-3-(Z)-en-1-ylidenetriphenylphosphorane 
• 128860-99-1 Benzoic acid (2E,4E,7Z)-(S)-11-methoxycarbonyl-1-pentyl-undeca-2,4,7-trienyl ester 
• 128860-98-0 Benzoic acid (2E,4Z,7Z)-(R)-11-methoxycarbonyl-1-pentyl-undeca-2,4,7-trienyl ester 
• 108437-64-5 12-oxo-5Z,8Z,10E,14Z-eicosatetraenoic acid 
• 82337-46-0 (R)-12-HETE 
• 54397-83-0 12-hydroxyeicosatetraenoic acid 

Relevant academic research and scientific papers

First Total Syntheses of Novel Non-Enzymatic Polyunsaturated Fatty Acid Metabolites and Their Identification in Edible Oils

Oxidative stress (OS) is an in vivo process leading to free radical overproduction, which triggers polyunsaturated fatty acid (PUFA) peroxidation resulting in the formation of racemic non-enzymatic oxygenated metabolites. As potential biomarkers of OS, their in vivo quantification is of great interest. However, since a large number of isomeric metabolites is formed in parallel, their quantification remains difficult without primary standards. Three new PUFA-metabolites, namely 18-F3t-isoprostane (IsoP) from eicosapentaenoic acid (EPA), 20-F4t-neuroprostane (NeuroP) from docosahexaenoic acid (DHA) and 20-F3t-NeuroP from docosapentaenoic acid (DPAn-3) were synthesized by two complementary synthetic strategies. The first one relied on a racemic approach to 18(RS)-18-F3t-IsoP using an oxidative radical anion cyclization as a key step, whereas the second used an enzymatic deracemization of a bicyclo[3.3.0]octene intermediate obtained from cyclooctadiene to pursue an asymmetric synthesis. The synthesized metabolites were applied in targeted lipidomics to prove lipid peroxidation in edible oils of commercial nutraceuticals.

A short catalytic enantioselective synthesis of the vascular antiinflammatory eicosanoid (11R,12S)-oxidoarachidonic acid

(Equation presented) An effective pathway is described for the synthesis of (11R,12S)-oxidoarachidonic acid (1) from the achiral precursors shown.

Synthesis of 12-KETE and its 8,9-trans-isomer

The first total synthesis of the highly unstable biological mediator 12-ketoeicosatetraenoic acid (12-KETE) 3 and its 8,9-trans-isomer 20 is presented. The strategy focusses on the stable precursor dithiane 13 and its conversion to 3 and 20. Biochemical e

SYNTHESIS OF 12-HYDROPEROXYEICOSATETRAENOIC ACID (12-HPETE). ON THE STEROCHEMISTRY IN THE CONVERSION OF 12(S)-HETE TO 12-HPETE

12(S)-hydroxyeicosatetraenoic acid methyl ester 1 was synthesized. 1 was converted to phosphite 17 which upon treatment with hydrogen peroxide afforded the corresponding hydroperoxide 18 (12-HPETE methyl ester) with partially retained configuration.

Inhibitors of SRS-synthesis

Methyl derivatives of arachidonic acid and intermediates thereto have been synthesized. These derivatives are inhibitors of SRS-A synthesis and are useful for treating and preventing allergic reactions.