107656-13-3

Basic information

• Product Name: 9(S)-HETE
• Synonyms: 9(S)-HYDROXYEICOSA-5Z,7E,11Z,14Z-TETRAENOIC ACID;9S-HYDROXY-5Z,7E,11Z,14Z-EICOSATETRAENOIC ACID;9(S)-HETE;9(S)-hydroxy-(5Z,7E,11Z,14Z)-*eicosatetraenoic ac;KATOYYZUTNAWSA-VBLHFSPLSA-N
• CAS NO: 107656-13-3
• Molecular Formula: C20H32O3
• Molecular Weight: 320.47
• Mol File: 107656-13-3.mol

Chemical Properties

• Boiling Point: 487.7°C at 760 mmHg
• Flash Point: 262.8°C
• Appearance: /
• Density: 0.984g/cm³
• Vapor Pressure: 1.48E-11mmHg at 25°C
• Refractive Index: 1.513
• PKA: 4.73±0.10(Predicted)
• CAS DataBase Reference: 9(S)-HETE(CAS DataBase Reference)
• NIST Chemistry Reference: 9(S)-HETE(107656-13-3)
• EPA Substance Registry System: 9(S)-HETE(107656-13-3)

Safety Data

• Hazardous Substances Data: 107656-13-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
9(S)-HETE is used as a bioactive molecule for its potential role in modulating various cellular processes and signaling pathways. It has been found to be involved in the regulation of inflammation, cell proliferation, and immune responses, making it a promising candidate for the development of new drugs targeting these processes.
Used in Research and Development:
In the field of scientific research, 9(S)-HETE is used as a research tool to study the mechanisms of arachidonic acid metabolism and the role of eicosanoids in various physiological and pathological conditions. It can help researchers understand the complex interactions between different signaling pathways and identify potential therapeutic targets for the treatment of various diseases.
Used in Drug Delivery Systems:
Similar to gallotannin, 9(S)-HETE can also be incorporated into novel drug delivery systems to enhance its bioavailability and therapeutic efficacy. By using carriers such as organic and metallic nanoparticles, the delivery, solubility, and stability of 9(S)-HETE can be improved, allowing for more effective treatment of conditions where it has demonstrated potential benefits.

InChI:InChI=1/C20H32O3/c1-2-3-4-5-6-7-8-10-13-16-19(21)17-14-11-9-12-15-18-20(22)23/h6-7,9-11,13-14,17,19,21H,2-5,8,12,15-16,18H2,1H3,(H,22,23)/b7-6-,11-9-,13-10-,17-14+/t19-/m0/s1

Upstream product

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

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.

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.

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

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.