| Identification | Back Directory | [Name]
(5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid | [CAS]
578008-43-2 | [Synonyms]
Resolvin D5
7(S),17(S)-Resolvin D5
(5Z,7S,8E,10Z,13Z,15E,17S,19Z)-7,17-dihydroxydocosa-5,8,10,13,15,19-hexaenoic acid | [Molecular Formula]
C22H32O4 | [MOL File]
578008-43-2.mol | [Molecular Weight]
360.49 |
| Chemical Properties | Back Directory | [Boiling point ]
559.4±50.0 °C(Predicted) | [density ]
1.048±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -80°C,protect from light | [solubility ]
DMF: 50 mg/ml; Ethanol: 50 mg/ml; PBS (pH 7.2): 0.5 mg/ml | [pka]
4.58±0.10(Predicted) |
| Hazard Information | Back Directory | [Description]
Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid (EPA; ) and docosahexaenoic acid (DHA; ). In addition to being anti-inflammatory, resolvins promote the resolution of the inflammatory response back to a non-inflamed state. Resolvins are a family of potent lipid mediators derived from both eicosapentaenoic acid (EPA; ) and docosahexaenoic acid (DHA; ). In addition to being anti-inflammatory, resolvins promote the resolution of the inflammatory response back to a non-inflamed state. Resolvin D5 (RvD5) is a DHA-derived resolvin generated by a double dioxygenation mechanism. RvD5 has been identified in media from ionophore-stimulated trout brain cells, in human synovial fluid from patients with rheumatoid arthritis, and in exudates of bacterial infections in mice. RvD5 stimulates the phagocytosis of E. coli by human macrophages, and RvD5 methyl ester enhances bacterial killing in mice inoculated with E. coli. Analytical and biological comparisons of synthetic RvD5 with endogenously derived RvD5 have confirmed its identity as matching the natural product. | [Uses]
7(S),17(S)-Resolvin D5 is a docosahexaenoic acid (D494500), which is a ω-3 fatty acid that is found in the brain, synapses, and retina. It also exhibits anti-inflammatory activity. | [storage]
Store at -80°C,protect from light | [References]
[1] SONG HONG. Novel docosatrienes and 17S-resolvins generated from docosahexaenoic acid in murine brain, human blood, and glial cells. Autacoids in anti-inflammation.[J]. The Journal of Biological Chemistry, 2003, 278 17: 14677-14687. DOI: 10.1074/jbc.m300218200
[2] AMIRAM ARIEL Charles N S. Resolvins and protectins in the termination program of acute inflammation.[J]. Trends in Immunology, 2007, 28 4: 176-183. DOI: 10.1016/j.it.2007.02.007
[3] C. SERHAN. Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: assignments of dihydroxy-containing docosatrienes.[J]. The Journal of Immunology, 2006, 62 1: 3843-3843. DOI: 10.4049/jimmunol.176.6.3843-a
[4] SONG HONG . Rainbow trout (Oncorhynchus mykiss) brain cells biosynthesize novel docosahexaenoic acid-derived resolvins and protectins—Mediator lipidomic analysis[J]. Prostaglandins & other lipid mediators, 2005, 78 1: Pages 107-116. DOI: 10.1016/j.prostaglandins.2005.04.004
[5] MARTIN GIERA . Lipid and lipid mediator profiling of human synovial fluid in rheumatoid arthritis patients by means of LC–MS/MS[J]. Biochimica et biophysica acta. Molecular and cell biology of lipids, 2012, 1821 11: Pages 1415-1424. DOI: 10.1016/j.bbalip.2012.07.011
[6] NAN CHIANG. Infection regulates pro-resolving mediators that lower antibiotic requirements[J]. Nature, 2012, 484 7395: 524-528. DOI: 10.1038/nature11042
[7] ANNE-SOPHIE ARCHAMBAULT. Human and Mouse Eosinophils Differ in Their Ability to Biosynthesize Eicosanoids, Docosanoids, the Endocannabinoid 2-Arachidonoyl-glycerol and Its Congeners.[J]. Cells, 2022. DOI: 10.3390/cells11010141
[8] ANNE-SOPHIE ARCHAMBAULT. High levels of eicosanoids and docosanoids in the lungs of intubated COVID-19 patients[J]. FASEB Journal, 2021, 35 6. DOI: 10.1096/fj.202100540r
[9] LYDIA M. ROBERTS . Pulmonary infection induces persistent, pathogen-specific lipidomic changes influencing trained immunity[J]. iScience, 2021, 24 9: Article 103025. DOI: 10.1016/j.isci.2021.103025
[10] IVAN HARTLING. Quantitative profiling of inflammatory and pro-resolving lipid mediators in human adolescents and mouse plasma using UHPLC-MS/MS.[J]. Clinical chemistry and laboratory medicine, 2021, 59 11: 1811-1823. DOI: 10.1515/cclm-2021-0644
[11] ANNE-SOPHIE ARCHAMBAULT. Lipid storm within the lungs of severe COVID-19 patients: Extensive levels of cyclooxygenase and lipoxygenase-derived inflammatory metabolites.[J]. medRxiv?: the preprint server for health sciences, 2020, 249 1. DOI: 10.1101/2020.12.04.20242115
[12] LAURA KUTZNER. Development of an Optimized LC-MS Method for the Detection of Specialized Pro-Resolving Mediators in Biological Samples.[J]. Frontiers in Pharmacology, 2019: 169. DOI: 10.3389/fphar.2019.00169
[13] DAVID MERIWETHER. Apolipoprotein A-I mimetics mitigate intestinal inflammation in COX2-dependent inflammatory bowel disease model.[J]. Journal of Clinical Investigation, 2019, 129 9: 3670-3685. DOI: 10.1172/jci123700
[14] JESMOND DALLI. Lipid Mediator Metabolomics Via LC-MS/MS Profiling and Analysis.[J]. Methods in molecular biology, 2018, 1730: 59-72. DOI: 10.1007/978-1-4939-7592-1_4 |
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