111990-31-9

Basic information

• Product Name: (5R,15S)-Dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoic Acid
• Synonyms: 6,8,11,13-Eicosatetraenoicacid, 5,15-dihydroxy-, [S-[R*,S*-(E,E,Z,Z)]]-
• CAS NO: 111990-31-9
• Molecular Formula: C20H32 O4
• Molecular Weight: 336.47
• Mol File: 111990-31-9.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 537.6±50.0 °C(Predicted)
• Appearance: /
• Density: 1.040±0.06 g/cm3(Predicted)
• PKA: 4.67±0.10(Predicted)
• CAS DataBase Reference: (5R,15S)-Dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: (5R,15S)-Dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoic Acid(111990-31-9)
• EPA Substance Registry System: (5R,15S)-Dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoic Acid(111990-31-9)

Safety Data

• Hazardous Substances Data: 111990-31-9(Hazardous Substances Data)

Usage

General Description

The chemical (5R,15S)-Dihydroxy-(6E,8Z,11Z,13E)-eicosatetraenoic acid, also known as 5,15-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid or 15(S)-HETE, is a metabolite of arachidonic acid and is generated by the enzymatic action of 15-lipoxygenase. It is a potent bioactive lipid mediator that plays a role in inflammation, immune response, and regulation of vascular tone. It has been implicated in various physiological and pathological processes, including asthma, atherosclerosis, and cancer. Its actions are mediated through binding to specific receptors and activation of downstream signaling pathways, and it is a potential target for the development of therapeutics for various inflammatory diseases.

Upstream product

• 61641-47-2 (5R)-HETE 

Relevant articles and documents

Identification and absolute configuration of dihydroxy-arachidonic acids formed by oxygenation of 5 S-HETE by native and aspirin-acetylated COX-2

Biosynthesis of the prostaglandin endoperoxide by the cyclooxygenase (COX) enzymes is accompanied by formation of a small amount of 11 R- hydroxyeicosatetraenoic acid (HETE), 15 R-HETE, and 15 S-HETE as by-products. Acetylation of COX-2 by aspirin abrogates prostaglandin synthesis and triggers formation of 15 R-HETE as the sole product of oxygenation of arachidonic acid. Here, we investigated the formation of by-products of the transformation of 5 S-HETE by native COX-2 and by aspirin-acetylated COX-2 using HPLC-ultraviolet, GC-MS, and LC-MS analysis. 5 S,15 S-dihydroxy (di)HETE, 5 S,15 R-diHETE, and 5 S,11 R-diHETE were identified as by-products of native COX-2, in addition to the previously described di-endoperoxide (5 S,15 S-dihydroxy-9 S,11 R,8 S,12 S-diperoxy-6 E,13 E-eicosadienoic acid) as the major oxygenation product. 5 S,15 R-diHETE was the only product formed by aspirinacetylated COX-2. Both 5,15-diHETE and 5,11-diHETE were detected in CT26 mouse colon carcinoma cells as well as in lipopolysaccharide-activated RAW264.7 cells incubated with 5 S-HETE, and their formation was attenuated in the presence of the COX-2 specific inhibitor, NS-398. Aspirintreated CT26 cells gave 5,15-diHETE as the most prominent product formed from 5 S-HETE. 5 S,15 S-diHETE has been described as a product of the cross-over of 5-lipoxygenase (5-LOX) and 15-LOX activities in elicited rat mononuclear cells and human leukocytes, and our studies implicate crossover of the 5-LOX and COX-2 pathways as an additional biosynthetic route. Copyright