| Identification | Back Directory | [Name]
(±)13(14)-EpDPA | [CAS]
895127-64-7 | [Synonyms]
(±)13(14)-EpDPA
13(14)-Epoxy-Docosapentaenoic acid
(4(Z),7(Z),10Z)-12-[3-(2(Z),5Z)-2,5-octadien-1-yl-2-oxiranyl]-4,7,10-dodecatrienoic acid | [Molecular Formula]
C22H32O3 | [MOL File]
895127-64-7.mol | [Molecular Weight]
344.49 |
| Chemical Properties | Back Directory | [Boiling point ]
462.8±33.0 °C(Predicted) | [density ]
0.994±0.06 g/cm3(Predicted) | [storage temp. ]
Store at -20°C | [solubility ]
DMF: 25 mg/mL; DMSO: 20 mg/mL; Ethanol: 50 mg/mL; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/mL | [form ]
Liquid | [pka]
4.58±0.10(Predicted) | [color ]
Colorless to light yellow |
| Hazard Information | Back Directory | [Description]
Cytochrome P450 metabolism of polyunsaturated fatty acids produces numerous bioactive epoxide regioisomers. (±)13(14)-EpDPA is a docosahexaenoic acid (DHA; ) epoxygenase metabolite, derived via epoxidation of the 13,14-double bond of DHA. It has been detected in rat brain and spinal cord and is a preferred substrate for soluble epoxide hydrolase with a Km value of 3.2 μM. (±)13(14)-EpDPA demonstrates antihyperalgesic activity in inflammatory and neuropathic pain models.1 (±)13(14)-EpDPA and other epoxy metabolites of DHA are also reported to potently inhibit angiogenesis and tumor growth in in vitro assays.2 | [References]
1. Morisseau, C., Inceoglu, B., Schmelzer, K., et al. Naturally occurring monoepoxides of eicosapentaenoic acid and docosahexaenoic acid are bioactive antihyperalgesic lipids J. Lipid Res. 51,3481-3490(2010).
2. Zhang, G., Panigrahy, D., Mahakian, L.M., et al. Epoxy metabolites of docosahexaenoic acid (DHA) inhibit angiogenesis, tumor growth, and metastasis Proc. Natl. Acad. Sci. USA 110(16),6530-6535(2013). |
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