71030-37-0

Usage

Uses

Used in Pharmaceutical Industry:
(+/-)12-HETE is used as a pharmaceutical agent for its potential role in modulating inflammatory responses and immune system functions. Its ability to aggregate neutrophils makes it a valuable compound for studying the mechanisms of inflammation and immune cell interactions.
Used in Research Applications:
(+/-)12-HETE is used as a research tool for investigating the biological activity and signaling pathways related to arachidonic acid metabolism. It aids in understanding the role of eicosanoids in various physiological and pathological processes, including inflammation, pain, and tissue repair.
Used in Drug Development:
(+/-)12-HETE is utilized in the development of new drugs targeting inflammatory and immune-related disorders. Its unique properties and interactions with immune cells make it a promising candidate for the creation of novel therapeutic agents to treat various diseases.

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

Upstream product

• 56630-33-2 non-3-ynoic acid 
• 197508-63-7 14,15-Epoxyeicosatrienoic acid methylester 
• 31823-43-5 (Z)-3-nonenal 
• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 20739-58-6 2-octyn-1-ol 
• 26001-58-1 (Z)-oct-2-en-1-ol 
• 74868-40-9 methyl 12-hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoate 
• 73799-10-7 (5Z,8Z,10E)-12-Hydroxy-13-(3-pentyl-oxiranyl)-trideca-5,8,10-trienoic acid 
• 200960-01-6 11,12-cis-epoxyeicosatrienoic acid 
• 95646-01-8 (6Z,10E,12Z,15Z)-19-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-nonadeca-6,10,12,15-tetraen-9-ol 
• 95645-98-0 Tributyl-[(1Z,4Z)-8-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-octa-1,4-dienyl]-stannane 
• 129030-85-9 (+/-)-(5Z)-5-undecen-1-yn-3-ol 
• 95646-00-7 (6Z,10E,12Z,15Z)-19-(4-Methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-nonadeca-6,10,12,15-tetraen-9-one 
• 95645-99-1 (Z)-Undec-5-en-1-yn-3-one 

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.

The Total Synthesis of 12-HETE and 12,20-DiHETE

The total syntheses of 12-HETE (1) in racemic form and of both enantiomers in optically pure form are reported.The synthesis of a metabolite of 12(S)-HETE, 12,20-diHETE (2), in optically pure form is also reported.

Total Synthesis of (+/-)-12-Hydroxy-5(Z),8(Z),10(E),14(Z)-eicosatetraenoic Acid (12-HETE)

A total synthesis of 12-HETE is reported which incorporates an oxidative cleavage of an appropriately substituted furan to provide a functionalized trans-allylhydroxy fragment which is subsequently elaborated in an operationally simple manner affording a practical preparation of 12-HETE.

A SHORT, THREE-COMPONENT TOTAL SYNTHESIS OF 12-HYDROXYEICOSA-5,8,14(Z),10(E)-TETRAENOIC ACID (12-HETE) VIA THE CORRESPONDING KETONE

A highly effective synthesis of (+/-)-12-HETE (1) from the componenets 2, 3, and 6 is desribed which employs a new class of cuprate reagents.