107656-14-4

Basic information

• Product Name: 9(R)-HETE
• Synonyms: 9(R)-HETE;9R-HYDROXY-5Z,7E,11Z,14Z-EICOSATETRAENOIC ACID;9(R)-hydroxy-(5Z,7E,11Z,14Z)-*eicosatetraenoic ac;KATOYYZUTNAWSA-AZFZJQGOSA-N
• CAS NO: 107656-14-4
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• Mol File: 107656-14-4.mol

Chemical Properties

• Boiling Point: 487.7±33.0 °C(Predicted)
• Appearance: /
• Density: 0.984±0.06 g/cm3(Predicted)
• PKA: 4.73±0.10(Predicted)
• CAS DataBase Reference: 9(R)-HETE(CAS DataBase Reference)
• NIST Chemistry Reference: 9(R)-HETE(107656-14-4)
• EPA Substance Registry System: 9(R)-HETE(107656-14-4)

Safety Data

• Hazardous Substances Data: 107656-14-4(Hazardous Substances Data)

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 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 
• 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 
• 89682-65-5 (2Z,4E)-Heptadeca-2,4-diene-8,11-diyne-1,6-diol 
• 89682-62-2 1-Diazo-trideca-4,7-diyn-2-one 
• 65090-68-8 dodeca-3,6-diyn-1-ol 
• 70968-96-6 +/-9-HETE Me-ester 

Relevant articles and documents

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

ω-alkynyl lipid surrogates for polyunsaturated fatty acids: Free radical and enzymatic oxidations

Lipid and lipid metabolite profiling are important parameters in understanding the pathogenesis of many diseases. Alkynylated polyunsaturated fatty acids are potentially useful probes for tracking the fate of fatty acid metabolites. The nonenzymatic and enzymatic oxidations of ω-alkynyl linoleic acid and ω-alkynyl arachidonic acid were compared to that of linoleic and arachidonic acid. There was no detectable difference in the primary products of nonenzymatic oxidation, which comprised cis,trans-hydroxy fatty acids. Similar hydroxy fatty acid products were formed when ω-alkynyl linoleic acid and ω-alkynyl arachidonic acid were reacted with lipoxygenase enzymes that introduce oxygen at different positions in the carbon chains. The rates of oxidation of ω-alkynylated fatty acids were reduced compared to those of the natural fatty acids. Cyclooxygenase-1 and -2 did not oxidize alkynyl linoleic but efficiently oxidized alkynyl arachidonic acid. The products were identified as alkynyl 11-hydroxy-eicosatetraenoic acid, alkynyl 11-hydroxy-8,9-epoxy-eicosatrienoic acid, and alkynyl prostaglandins. This deviation from the metabolic profile of arachidonic acid may limit the utility of alkynyl arachidonic acid in the tracking of cyclooxygenase-based lipid oxidation. The formation of alkynyl 11-hydroxy-8,9-epoxy-eicosatrienoic acid compared to alkynyl prostaglandins suggests that the ω-alkyne group causes a conformational change in the fatty acid bound to the enzyme, which reduces the efficiency of cyclization of dioxalanyl intermediates to endoperoxide intermediates. Overall, ω-alkynyl linoleic acid and ω-alkynyl arachidonic acid appear to be metabolically competent surrogates for tracking the fate of polyunsaturated fatty acids when looking at models involving autoxidation and oxidation by lipoxygenases.

Identification of an amino acid determinant of pH regiospecificity in a seed lipoxygenase from Momordica charantia

Lipoxygenases (LOX) form a heterogeneous family of lipid peroxidizing enzymes, which catalyze specific dioxygenation of polyunsaturated fatty acids. According to their positional specificity of linoleic acid oxygenation plant LOX have been classified into linoleate 9- and linoleate 13-LOX and recent reports identified a critical valine at the active site of 9-LOX. In contrast, more bulky phenylalanine or histidine residues were found at this position in 13-LOX. We have recently cloned a LOX-isoform from Momordica charantia and multiple amino acid alignments indicated the existence of a glutamine (Gln599) at the position were 13-LOX usually carry histidine or phenylalanine residues. Analyzing the pH-dependence of the positional specificity of linoleic acid oxygenation we observed that at pH-values higher than 7.5 this enzyme constitutes a linoleate 13-LOX whereas at lower pH, 9-H(P)ODE was the major reaction product. Site-directed mutagenesis of glutamine 599 to histidine (Gln599His) converted the enzyme to a pure 13-LOX. These data confirm previous observation suggesting that reaction specificity of certain LOX-isoforms is not an absolute enzyme property but may be impacted by reaction conditions such as pH of the reaction mixture. We extended this concept by identifying glutamine 599 as sequence determinant for such pH-dependence of the reaction specificity. Although the biological relevance for this alteration switch remains to be investigated it is of particular interest that it occurs at near physiological conditions in the pH-range between 7 and 8.

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.

Biosynthesis of dictyopterene A: Stereoselectivity of a lipoxygenase/hydroperoxide lyase from Gomphonema parvulum (Bacillariophyceae)

(9S)-Hydroperoxyicosatetraenoic (9S-HPETE) acid is shown to be an intermediate in the biosynthesis of dictyopterene A in the freshwater diatom Gomphonema parvulum; the stereochemistry of (9S)-HPETE and the position of the hydrogen atom at C(16) lost during fatty acid cyclisation and oxidative cleavage of the hydroperoxide were investigated using trapping experiments and chirally deuterium labelled fatty acids.

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.