70968-92-2

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 89682-62-2 1-Diazo-trideca-4,7-diyn-2-one 
• 89682-65-5 (2Z,4E)-Heptadeca-2,4-diene-8,11-diyne-1,6-diol 
• 89682-66-6 (2Z,4E,8Z,11Z)-6-(tert-Butyl-diphenyl-silanyloxy)-heptadeca-2,4,8,11-tetraen-1-ol 
• 89682-67-7 [(3Z,6Z)-1-((1E,3Z)-5-Bromo-penta-1,3-dienyl)-dodeca-3,6-dienyloxy]-tert-butyl-diphenyl-silane 
• 89682-64-4 (2Z,4E)-6-Oxo-heptadeca-2,4-diene-8,11-diynal 
• 65090-68-8 dodeca-3,6-diyn-1-ol 
• 70968-96-6 +/-9-HETE Me-ester 
• 89682-70-2 (5Z,7E,11Z,14Z)-9-(tert-Butyl-diphenyl-silanyloxy)-icosa-5,7,11,14-tetraenoic acid methyl ester 
• 89682-69-9 (5Z,7E,11Z,14Z)-9-(tert-Butyl-diphenyl-silanyloxy)-icosa-5,7,11,14-tetraenoic acid 
• 89702-37-4 (5Z,7E,11Z,14Z)-9-(tert-Butyl-diphenyl-silanyloxy)-icosa-5,7,11,14-tetraenal 
• 89682-68-8 (5Z,7E,11Z,14Z)-9-(tert-Butyl-diphenyl-silanyloxy)-icosa-5,7,11,14-tetraen-1-ol 

Relevant academic research and scientific papers

Repurposing Resveratrol and Fluconazole to Modulate Human Cytochrome P450-Mediated Arachidonic Acid Metabolism

Cytochrome P450 (P450) enzymes metabolize arachidonic acid (AA) to several biologically active epoxyeicosatrienoic acids (EETs) and hydroxyeicosatetraenoic acids (HETEs). Repurposing clinically-approved drugs could provide safe and readily available means

Oxidation of oxa and thia fatty acids and related compounds catalysed by 5- and 15-lipoxygenase

The modified fatty acids, (Z,Z,Z)-(octadeca-6,9,12-trienyloxy)acetic acid, (Z,Z,Z)-(octadeca-9,12,15-trienyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid, 3-[(all-Z)-(eicosa-5,8,11,14-tetraenylthio)]propionic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)succinic acid, N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]glycine and N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]aspartic acid, all react with soybean 15-lipoxygenase. The products were treated with triphenylphosphine to give alcohols, which were isolated using HPLC. Analysis of the alcohols using negative ion tandem electrospray mass spectrometry, and by comparison with compounds obtained by autoxidation of arachidonic acid, shows that each enzyme-catalysed oxidation occurs at the ω-6 position of the substrate. In a similar fashion, it has been found that (Z,Z,Z)-(octadeca-6,9,12-trienyloxy)acetic acid, (Z,Z,Z)-(octadeca-9,12,15-trienyloxy)acetic acid, (all-Z)-(eicosa-5,8,11,14-tetraenylthio)acetic acid and 3-[(all-Z)-(eicosa-5,8,11,14-tetraenylthio)]propionic acid each undergoes regioselective oxidation at the carboxyl end of the polyene moiety on treatment with potato 5-lipoxygenase. Neither (all-Z)-(eicosa-5,8,11,14-tetraenylthio)succinic acid nor N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]aspartic acid reacts in the presence of this enzyme, while N-[(all-Z)-(eicosa-5,8,11,14-tetraenoyl)]glycine affords the C11′ oxidation product. The alcohol derived from (Z,Z,Z)-(octadeca-6,9,12-trienyloxy)acetic acid using the 15-lipoxygenase reacts at the C6′ position with the 5-lipoxygenase.

SYNTHESIS OF +/- 8- and 9-HETES

We describe the first total syntheses of +/-8 and +/-9 HETEs using the addition of diazoketones to furan followed by electrocyclic ring opening to provide the necessary cis-trans diene system.