82200-87-1

Basic information

• Product Name: 5(S), 15(S)-DIHETE
• Synonyms: 5(S), 15(S)-DIHETE;5S,15S-DIHYDROXY-6E,8Z,11Z,13E-EICOSATETRAENOIC ACID;5(S),15(S)-DIHYDROXYEICOSA-6E,8Z,11Z,13E-TETRAENOIC ACID;5,15-dihydroxy-6,8,11,13-eicosatetraenoicacid;(5S,15S)-dihydroxy-(6E,8Z,11Z,13E)-*eicosatetraen;(5S,15S)-DIHYDROXY-(6E,8Z,11Z,13E)-EICOS ATETRAENOI;5(S),15(S)-DiHETE Lipid Maps MS Standard;5,15-DiHETE
• CAS NO: 82200-87-1
• Molecular Formula: C20H32O4
• Molecular Weight: 336.47
• Mol File: 82200-87-1.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 537.6 °C at 760 mmHg
• Flash Point: 293 °C
• Appearance: /
• Density: 1.04 g/cm³
• Vapor Pressure: 8.43E-14mmHg at 25°C
• Refractive Index: 1.527
• Storage Temp.: -20°C
• CAS DataBase Reference: 5(S), 15(S)-DIHETE(CAS DataBase Reference)
• NIST Chemistry Reference: 5(S), 15(S)-DIHETE(82200-87-1)
• EPA Substance Registry System: 5(S), 15(S)-DIHETE(82200-87-1)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 16-26-36
• Hazardous Substances Data: 82200-87-1(Hazardous Substances Data)

Usage

Description

5(S),15(S)-DiHETE is synthesized by 15-LO from 5(S)-HETE. It potentiates the degranulation of human PMNL in response to PAF, but not fMLP, calcium ionophore A23187, or LTB4. 5(S),15(S)-DiHETE is chemotactic for eosinophils with an ED50 value of 0.3 μM.

Uses

Different sources of media describe the Uses of 82200-87-1 differently. You can refer to the following data:
1. 5(S),15(S)-DiHETE is synthesized by 15-LO from 5(S)-HETE. It potentiates the degranulation of human PMNL in response to PAF, but not fMLP, calcium ionophore A23187, or LTB4. 5(S),15(S)-DiHETE is chemotactic for eosinophils with an ED50 value of 0.3 μM.
2. 5(S),15(S)-DiHETE is an enhancer of neutrophil degranulation and potent chemotaxin.

InChI:InChI=1/C20H32O4/c1-2-3-9-13-18(21)14-10-7-5-4-6-8-11-15-19(22)16-12-17-20(23)24/h5-8,10-11,14-15,18-19,21-22H,2-4,9,12-13,16-17H2,1H3,(H,23,24)/b7-5-,8-6-,14-10+,15-11+/t18-,19+/m0/s1

Upstream product

• 506-32-1 all cis 5,8,11,14-eicosatetraenoic acid 
• 61641-47-2 5(S)-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